Winter Park, Orlando, FL Real Estate | Winter Park, Orlando, FL Just Listed Properties for Sale

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome home to this charming 1940's bungalow in Orwin Manor, one of Winter Park’s most sought-after neighborhoods. The single-story home has 3 bedrooms, 2 full baths and 1,594 square feet of living space. It keeps its original character, with wood floors throughout and graceful curved entryways. In the living room, a wood-burning fireplace sets a warm, inviting tone, and the open layout flows into the formal dining room, making the home easy to entertain in and comfortable for everyday living. The kitchen has been updated with shaker cabinetry, granite countertops and stainless steel appliances, while keeping the home’s vintage charm. A split bedroom plan gives the primary suite added privacy, with an en suite bath featuring a walk-in shower and a walk-in closet. Outside, the home sits on an oversized 0.31-acre lot (100 x 135), leaving plenty of room for gardening, play, outdoor living or future expansion, and a detached one-car garage adds storage and parking. Orwin Manor is a well-established, walkable community close to Winter Park’s restaurants and shopping, with easy access to major roadways. This home has great bones and a prime location, with plenty of potential to make it your own. Opportunities like this in Orwin Manor don’t come along often, so schedule your private showing today!

1401 Pelham Road, Winter Park

$5,995,000

5 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live in every day and will feel just as right decades from now. Set on nearly half an acre in the highly desirable Vias of Winter Park, this fully renovated, turnkey home is modern European design at its most elegant and understated, with bespoke cabinetry & built-ins in every room and rare natural stone throughout. It offers five bedrooms, five full baths, a half bath, and has been curated with the care of a private collection. A sculptural curved staircase greets you in the foyer, and wood floors carry through the main level. The living room rises beneath vaulted ceilings, centered on a gas fireplace wrapped in Sequoia quartzite, with a wall of sliding glass doors opening to the pool so gatherings drift outdoors without a second thought. In the kitchen, rare leathered Naica quartzite forms the waterfall island, countertops, & backsplash, and custom cabinetry rises floor to ceiling. Appliances include a Wolf gas range with pot filler, Sub-Zero refrigerator, & two Miele dishwashers, plus a prep sink, concealed outlets, & push-to-open, soft-close drawers. To one side, a pantry/butler’s passage with matching cabinetry also houses the laundry. At the front of the home, a bright formal dining room & eat-in area complete the space. Just off the eat-in area, a large turf side courtyard offers a low-maintenance space where kids & pets can play within view of the kitchen. The main-level primary suite features two walk-in closets & a double-sided wood-burning fireplace shared with the private office. The spa-inspired bath showcases leathered Taj Mahal quartzite with integrated dual sinks, an extra-large soaking tub for two, & a walk-in shower, all with Graff fixtures. The office opens to the pool and is outfitted with floor-to-ceiling shelving, cabinetry, & file drawers, versatile enough to become a dressing room. The whiskey lounge with custom wet bar is sized for a game room or second office. A powder room completes the main floor. Upstairs, custom cabinetry lines the loft & hallway, offering storage at every turn. To the left, two bedrooms share an elegant bath with dual sinks and a separate tub & shower, and a single door closes them off creating an optional, private two-bedroom suite. To the right, two additional bedrooms each enjoy an en suite bath. Every bedroom is finished with built-in closets. A separate upstairs wing houses the generously sized media room, with state-of-the-art surround sound & extensive hidden storage. Outdoors, a weathered marble pool deck surrounds the saltwater pool, framed by grounds created by Signature Landscape. The garden pavilion with its own fireplace is one of the home’s most special spaces, joined by a summer kitchen with stone counters & wall, a natural gas grill, & a sink, plus a pool bath. Additional features include a three-car side-entry garage with epoxy floors, EV charger capability, & ample storage, along with Lutron lighting on the main level, Toto toilets throughout, water filtration, natural gas, a whole-home generator, & three Trane HVAC systems. The Winter Park Racquet Club, Interlachen Country Club, the shops & dining of Park Avenue, and the Winter Park 9 golf course are all within walking distance. Refined, move-in ready, and crafted without compromise, 1200 Via Salerno awaits its next owner.

1200 Via Salerno, Winter Park

$1,050,000

4 Beds ⋅ 3 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

1735 Demetree Drive, Winter Park

$985,000

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

2330 Westminster Ct., Winter Park

$1,100,000

Comstock Park SubDv. ⋅ 32789 Zip Code

Exceptional opportunity to build on beautiful Bonita Drive, one of Winter Park’s most picturesque brick-lined streets, with this 0.18-acre (approximately 8,014-square-foot) homesite. Already cleared and ready for new construction, the property offers an ideal setting to create a custom residence tailored to your vision. Ideally positioned just minutes from Park Avenue’s shops and restaurants, Rollins College, the Winter Park Farmers’ Market, leading hospitals and top-rated schools, with convenient access to downtown Orlando, major roadways and area airports. Create your dream home in one of Winter Park’s most desirable residential settings.

1030 Bonita Drive, Winter Park

$699,900

3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natural light, and plantation shutters. The spacious family room features laminate flooring and a wood-burning fireplace, creating a welcoming place to gather. The updated kitchen offers stainless steel appliances, ample drawer storage, a pullout pantry, and a sunny dinette with sliding doors to the outdoor living area. Multiple access points throughout the home connect to the screened pool enclosure, where a recently resurfaced pool and covered patio provide space for relaxing and entertaining. The primary suite features a walk-in closet and an en-suite bath with dual sinks and a separate shower. Two additional bedrooms offer flexibility for guests or a home office, while the second full bath includes a bathtub. An attached two-car garage provides laundry space, extensive cabinetry, and pull-down attic access. All appliances are included, adding convenience to this inviting Winter Park home.

1884 Jessica Court, Winter Park

$4,500,000

5 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, abundant natural light, and premium finishes throughout. Every bedroom features its own en-suite bath. Resort-style pool and putting green anchor the outdoor living space, perfect for Florida's year-round lifestyle. Detached garage offers flexible storage, workshop space, plus room for a private home gym. Minutes from Park Avenue's shops, dining, and top-rated schools. Top quality construction and unbeatable location. Schedule your private showing today.

1631 Hillcrest Avenue, Winter Park

$3,195,000

4 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms, rich in architectural elegance. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom walnut cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Viking gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

1825 Whitehall Drive, Winter Park

$450,000

4 Beds ⋅ 3 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code

Welcome to 239 Orange Terrace Drive! This charming 4 bedroom, 2.5 bath home offers 1,866 square feet of living space in a convenient Winter Park location. Situated on a spacious lot of approximately 0.21 acres with NO HOA. Step inside to discover an expansive living room filled with natural light, offering ample room for relaxing or entertaining. The adjoining formal dining room offers an inviting space for gatherings, while the kitchen features light wood cabinetry with a warm maple finish, sleek brushed nickel hardware, endless counterspace, ample storage, and a convenient pass through connecting the two spaces. Just beyond the kitchen, a separate breakfast nook offers additional dining space, along with an indoor laundry area. The home also features a distinctive brick fireplace and additional living space that can accommodate a variety of uses. With four bedrooms and two full bathrooms plus a half bath, the layout provides flexibility for guests, a home office, or everyday living. Step outside to enjoy the large backyard, offering plenty of room for outdoor activities, entertaining, or simply relaxing. A dedicated outdoor sitting area presents the perfect opportunity to create your own backyard retreat with the addition of a pergola or gazebo. Multiple storage sheds provide convenient space for tools, lawn equipment, and other outdoor essentials. With no HOA restrictions or fees, you'll enjoy added flexibility in making this property your own. Conveniently located near Lake Killarney, Park Avenue, shopping, dining, and major roadways, this property offers easy access to everything Winter Park and the surrounding Orlando area have to offer. Whether you're looking for a place to call home or an opportunity to add your personal touches, 239 Orange Terrace Drive offers space, character, and location!

239 Orange Terrace Drive, Winter Park

$695,000

2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code

Some homes stand out because of their finishes. Others because of their location. Rarely do you find one that brings both together so beautifully. Nestled alongside an 81-acre nature preserve, this reimagined two-story, fee-simple, end-unit townhouse offers contemporary living surrounded by nature. With approximately 1,800 square feet, 2 bedrooms, 2.5 bathrooms, and no HOA, this exceptional property feels more like a personal retreat than a traditional townhome. Designed with a modern, contemporary point of view, the home features bamboo hardwood floors and 14-foot vaulted ceilings that give the main living space an open, light-filled atmosphere, while a sleek gas fireplace brings warmth and character to the room. The kitchen includes an eat-in breakfast nook. Granite countertops, custom soft-close cabinetry, high-end stainless steel appliances, gas cooking, and a wine refrigerator combine style with everyday functionality. Additional built-ins provide attractive storage while maintaining the home's clean, cohesive aesthetic. A spacious interior laundry and utility room with an additional refrigerator provides added storage. Upstairs, the primary suite takes full advantage of the home's exceptional setting, offering peaceful views across the surrounding greenery. The primary bath features dual sinks, vanity, stone countertops, and a spacious walk-in shower with three shower heads, including a rain shower. A spacious walk-in closet completes the suite. A second bedroom and full bath provide comfortable accommodations for guests or the flexibility to create a home office or personal retreat. Parking is also a standout feature, with a one-car garage plus two designated parking spaces. Outside is where the personality of this property really comes to life. The oversized upper and lower decks create an exceptional outdoor living experience. The upper deck features a gas grill for cooking and entertaining, along with spectacular views of rocket launches from Cape Canaveral. An area provides space for relaxing, while an outdoor shower, potting station, plenty of exterior storage, and a private backyard with access to Howell Branch Creek for kayaking add to the property's distinctive appeal. Lush tropical landscaping creates a garden-like setting with citrus trees, including lemon, avocado, papaya, and a unique cocktail tree, complemented by fragrant jasmine and colorful seasonal blooms. An outdoor fire pit adds warmth and ambiance on cooler evenings. Whether you're having coffee before the day begins, sharing dinner with friends, or just enjoying the quiet after sunset, the natural surroundings make these spaces feel remarkably removed from city life. Key updates include a new tile roof replacement, HVAC installation, and water heater in 2018. Located in Winter Park's 32789 ZIP code, the home is near the Winter Park Racquet Club, Winter Park Chain of Lakes, iconic Park Avenue, fine dining, upscale boutiques, Rollins College, and highly regarded schools, including Dommerich Elementary and Winter Park High School. SunRail is also nearby, with Maitland just minutes away. Modern interiors, exceptional outdoor space with spectacular views, and the convenience of Winter Park, all in one place. For the buyer who has been waiting for something genuinely special, this may be the one.

2887 Temple Trail, Winter Park

$4,695,000

11 Beds ⋅ 8 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision. From the moment you arrive, the classic Spanish Revival influence and established setting offer a sense of history and individuality rarely found in newer construction. The multiple buildings create exciting possibilities for guest accommodations, private home offices, studios, hobby spaces, entertaining areas, or other uses permitted by applicable zoning and regulations. The residence offers an opportunity to preserve its distinctive architectural character while updating and personalizing the interiors and amenities for today's lifestyle. For buyers who appreciate homes with a story, architectural distinction, and the potential to make a property uniquely their own, this estate stands apart from the typical Winter Park offering. Even more compelling is the location. The property is within walking distance of Winter Park's famous Park Avenue, renowned for its restaurants, boutiques, cafes, galleries, cultural attractions, and unmistakable charm. Enjoy the rare opportunity to leave the car at home and stroll to one of Central Florida's most celebrated dining, shopping, and entertainment destinations. Rollins College is also nearby, while convenient access to downtown Orlando combines the charm and sophistication of Winter Park with easy connectivity to the greater Orlando area. The property is not individually listed on the Winter Park Register of Historic Places and is not located within a locally designated historic district, an important consideration for buyers exploring future renovation and personalization plans. Buyers should independently verify applicable zoning, permitting, building, and preservation requirements for any intended improvements or uses. With its James Gamble Rogers II design, 1929 origins, Spanish Revival character, approximately half-acre setting, substantial combined square footage, three accessory buildings, and an outstanding location within walking distance of famous Park Avenue, 617 N Interlachen Ave is far more than a conventional home purchase. It is an opportunity to take a distinctive piece of Winter Park architecture and shape its next chapter. Bring your vision and discover the possibilities where history, architecture, location, and potential come together in a truly one-of-a-kind Winter Park estate.

617 N Interlachen Avenue, Winter Park

$3,495,000

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

$2,629,000

5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, this stunning residence pairs a distinctive façade with interiors that feel both richly detailed and effortlessly livable. From the marble mosaic foyer to the private poolside retreat, each space offers its own expression of luxury, creating a home with character, warmth, and a beautiful sense of arrival. Beyond the entry, the spacious living area unfolds beneath shiplap ceiling details that lend texture and architectural depth. A statement wall with an electric fireplace anchors the room, establishing an inviting setting for quiet evenings and lively gatherings alike. The kitchen takes center stage with Taj Mahal countertops and a full suite of Thermador appliances. A built-in paneled refrigerator preserves the cabinetry’s seamless appearance, while a spacious walk-in pantry provides ample storage beyond the main kitchen. Positioned downstairs, the primary suite offers a peaceful retreat with a spacious closet and a beautifully composed spa bath featuring dual vanities, a freestanding soaking tub, and a separate shower with a rain showerhead and marble mosaic tile. A second downstairs guest suite adds exceptional versatility, a rare feature for the area, providing comfortable accommodations for visitors or a space for a private office. Providing comfortable accommodations for visitors or an inspiring space for a private office. Upstairs, three additional bedrooms, each with a walk-in closet, offer room for family and guests. A spacious loft introduces another place to gather, unwind, or create a dedicated media or recreation space, while the upstairs laundry room brings convenience to daily routine. Outdoors, a covered lanai with a summer kitchen sets the scene for alfresco dining and entertaining space. Lush landscaping surrounds the pool and spa, creating a beautiful backdrop for entertaining or simply enjoying the Florida lifestyle. Energy efficient doors and windows complete the home’s thoughtful collection of features. The location places neighborhood favorites within easy reach, with Phelps Park and the YMCA just a walk away and Park Avenue’s shops, restaurants, and cafés a short golf cart ride from home. Distinctive in its architecture and generous in its design, this residence offers a compelling opportunity to enjoy brand-new construction amid the established charm of Winter Park.

1681 Woodland Avenue, Winter Park

$305,000

3 Beds ⋅ 1 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A clean shell for a fix-and-flip or a hold-and-rent strategy, with detached ADU potential under Orange County rules. 3 bed, 1 bath, approx. 1,216 sq ft of living area on approx. 0.17 acre, FEMA Zone X (minimal flood hazard). Straightforward single-story footprint with room to improve, not expanded. Out back, a canopy of mature trees creates a shaded, private backyard sanctuary. Already handled: brand-new roof (October 2026) and a replaced water heater. Kitchen cabinets are in very good shape; if you choose to update the countertops, keep the cabinets and simply resurface and repaint. The deck is in good condition today (plan on rebuilding down the road). Still to do: central HVAC is not operational (home is cooled by window units), the shower needs a light spruce-up, and a cosmetic refresh throughout. Strong bones and a good shell for a focused remodel. Location: Lake Killarney, a 234-acre spring-fed lake, is just blocks away, where seaplanes drop in for lunch at Hillstone. Centrally located to I-4 at Fairbanks Avenue, with downtown Orlando about 15 minutes away. Less than 2 miles to the newly renovated Winter Park Village with its Regal cinema, restaurants, boutiques and patio dining, and minutes to Park Avenue, Rollins College, the Morse Museum, the Saturday Farmers Market, Trader Joe's, Whole Foods, AdventHealth Winter Park and the Winter Park SunRail station. ADU snapshot: under Orange County R-1A (Sec. 38-1426), a detached one-story ADU is typically limited to 50 percent of the primary living area or 1,000 sq ft, whichever is less, about 608 sq ft here. The lot appears to meet the 7,500 sq ft minimum. Homestead and owner-occupancy rules apply. Buyer to verify all zoning, setback, ADU eligibility, homestead and permitting items directly with Orange County Zoning. Figures are informational only and not a guarantee of approval. Renovate the primary and add a rental ADU for a two-income setup, or flip it. New roof and water heater done, interior ready for a focused remodel.

2640 Beverly Avenue, Winter Park

$1,550,000

Killarney Estates SubDv. ⋅ 32789 Zip Code

Rare hospitality-yield opportunity in Winter Park's Class A core, directly in the Hillstone trade area on South Orlando Avenue. The offering consists of 12 short-term rental units — 8 studios and 4 one-bedroom/one-bath — plus a street-facing office suite fronting S. Orlando Ave. The thesis is straightforward: Winter Park generates year-round, non-theme-park demand — Rollins, Park Avenue, AdventHealth Winter Park, and the corporate and event traffic that fills the surrounding hotels at rates a 12-unit boutique operation can match without a hotel's cost structure.

271 S Orlando Avenue, Winter Park

$320,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Oaks SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, without the Winter Park price tag! This 3 bed, 2 bath block home has already done the big stuff for you: 2020 roof, 2020 HVAC, 2023 water heater, and updated plumbing. That means your weekends are for enjoying life where you call home. Fresh paint inside and out sets the tone the moment you pull up. Step inside to a bright, open floor plan where the kitchen, dining, and living spaces flow together for easy weeknight dinners and lazy Saturday mornings. The kitchen and bathrooms have been updated with a clean, modern feel, so all that’s left is to unpack. Out back, a fully fenced vinyl yard gives you privacy and room to play, garden, or host the cookout. A one-car garage adds plenty of storage. And the location? It’s hard to beat. You’re minutes from everything Winter Park has to offer, tucked right behind the new LifeTime fitness club, with exciting new development planned for the area. Homes this updated in this location don’t come around often. Schedule your showing today!

148 Oak Grove Rd, Winter Park

$6,000,000

5 Beds ⋅ 7 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabinets, vanities, lighting, appliances, wallpaper to be CUSTOM SELECTED by Buyer. Also, layout of the rooms in in the photos may differ from the home to be built here.) The home is located on McKean Circle, one of the most sought-after, quiet, NO TRAFFIC streets in Winter Park… Very close walk to Park Avenue restaurants and shopping and Winter Park Golf Course. Presented by an established, award winning luxury home builder, this bespoke home will include premium features, appliances, fixtures and finishes as follows: ELEVATOR, NATURAL GAS WHOLE HOUSE GENERATOR, WOLF/SUB ZERO appliances and wine cooler tower, built-in coffee maker, LUTRON RA3 SMART LIGHTING AND WIRING FOR BLINDS AND DRAPES, AUDIO/VIDEO, SMART HOME and SECURITY UPGRADES, WALLPAPER, special carpentry and architectural details, CEILING DETAILS with LED recessed/cove LIGHTING. FIRST FLOOR PRIMARY SUITE WITH WASHER/DRYER and two-person shower, additional GUEST SUITE FIRST FLOOR, OFFICE FIRST FLOOR, 12' FIRST FLOOR CEILINGS with 10’ DOORS. UPSTAIRS THERE EN SUITES plus large LOFT with wet bar and laundry room. Store-front window and door system with SMART GLASS (on demand opaque or clear), large 18’x10’ full-view garage door, circular driveway, heated swimmable pool with spa, plenty of pool deck space, and exquisite landscaping. A 6’ masonry-stucco wall with gates will encompasses the property. Outdoor living includes a large rear covered lanai with retractable screens and a large summer kitchen, pool-bath and outdoor shower. Enjoy two fireplaces: a linear fireplace (choose natural gas or electric) in living room and optional natural gas fireplace on the pool deck. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself. Call now to schedule your meeting with the Builder to get started on your new home today!

1011 Mckean Circle, Winter Park

$575,000

Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

$575,000

3 Beds ⋅ 2 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

$3,390,000

5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rarely found in such a desirable location. Positioned on an expansive homesite with an impressive architectural façade and meticulously curated landscaping, the home makes an unforgettable first impression before revealing an interior designed for both elevated entertaining and everyday living. A dramatic foyer with soaring 22-foot ceilings introduces an exceptional floor plan. To one side, a color-drenched private office is enveloped in custom trim work, while the formal dining room opposite features floor-to-ceiling windows and an elegant coffered ceiling. Beyond, the expansive living room is anchored by a stone-wrapped fireplace and framed by arched built-in shelving with integrated LED lighting. Natural wood beams add warmth and architectural character, creating a space that feels equally refined and inviting. The chef’s kitchen is a statement in both beauty and performance, showcasing custom cabinetry, quartz countertops, a professional Wolf gas range, and an oversized paneled Sub-Zero refrigerator. Overhead beams bring dimension to the space, while the adjoining breakfast nook, with custom built-in bench seating offers a charming setting for casual dining. A generously sized butler’s pantry and laundry room provide exceptional storage and functionality. Privately positioned on the main level, the primary suite opens directly to the covered lanai. Its spa-inspired bath is finished in beautiful marble and features dual vanities with floating mirrors, an expansive wet room with a freestanding soaking tub, and a fully customized wardrobe by award-winning Idelli Closets. Upstairs, a spacious loft creates an additional living area surrounded by four generously proportioned bedroom suites, each complete with a private bath and walk-in closet. A second laundry room adds convenience to the upper level. The outdoor setting rivals a private resort. A magazine-worthy summer kitchen anchors the expansive covered lanai, while retractable screens allow for comfortable year-round entertaining. Beyond, a heated pool and spillover spa are complemented by marble decking and additional green space. Just moments from Lake Sue, Park Avenue, Rollins College, East End Market, and zoned for highly sought-after Audubon Park School, this remarkable residence presents an exceptional opportunity to experience one of Winter Park’s most compelling homes.

1751 Glencoe Road, Winter Park

$985,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.

1611 Chestnut Avenue, Winter Park

$950,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless character, sophisticated interiors and exceptional outdoor living in one of the area’s most desirable settings. Nestled along a tree-lined street and surrounded by mature landscaping, this 1,947-square-foot home offers two bedrooms, two baths and a versatile floor plan that can be easily converted back to its original three-bedroom configuration, providing flexibility for a home office, guest room or additional bedroom. Inside, rich hardwood flooring, crown molding, plantation shutters and a wood-burning fireplace lend warmth and character to the home, while French doors and abundant windows invite natural light throughout. The kitchen serves as an elegant centerpiece with custom cabinetry, Carrara marble countertops, a gas range and oven, stainless steel appliances, a breakfast bar and generous workspace. A tankless water heater adds modern efficiency and convenience. Multiple living and dining areas create an effortless flow for entertaining, while the expansive primary suite offers a private retreat with ample space for a sitting area. Beyond the interiors, the backyard creates a private resort-style setting rarely found so close to the heart of Winter Park. Fresh landscaping surrounds a saltwater pool, putting green, and expansive paver patio. A covered outdoor living and dining area provides an inviting backdrop for year-round entertaining. Mature trees, manicured hedges and multiple seating areas enhance the sense of privacy, creating a serene escape equally suited for quiet mornings, afternoons by the pool and evenings with guests. A paver driveway and charming covered entry complement the home’s classic architecture, while a Tesla charger adds the convenience of at-home EV charging. Ideally positioned in Orwin Manor, the residence is just minutes from I-4 access and AdventHealth, with convenient proximity to Park Avenue’s renowned boutiques, dining and cafés, as well as College Park and Downtown Orlando. Zoned for Killarney Elementary School, College Park Middle School and Edgewater High School, this distinctive residence presents an exceptional opportunity to enjoy the best of the Winter Park lifestyle.

1411 Devon Road, Winter Park

$1,399,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an impressive two-story foyer and bright, open floor plan designed for comfortable living and effortless entertaining. A private fourth bedroom with a full bath is located near the entry, offering flexibility as a guest suite, home office, study, or secluded retreat. ***KITCHEN & MAIN LIVING AREAS: The gourmet kitchen serves as the heart of the home, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package with a 36-inch electric cooktop. Open to the spacious living and dining areas, it creates a seamless setting for everyday living and entertaining. ***PRIMARY SUITE & UPSTAIRS SPACES: The first-floor primary suite provides a peaceful retreat with a spa-inspired bath, dual vanities, a freestanding soaking tub, and a generous walk-in closet with custom shelving. A nearby laundry area adds convenience and efficiency. Upstairs, a spacious bonus room with a closet can function as a fifth bedroom, media room, game room, home office, creative studio. Two additional bedrooms feature walk-in closets and share a beautifully appointed bathroom with dual sinks. A second laundry room with a sink and abundant natural light adds further convenience. ***OUTDOOR LIVING: The covered lanai overlooks a sparkling pool and beautifully landscaped backyard, creating for the outdoor relaxation and entertaining. The entire covered porch features a motorized retractable screening system, allowing the space to be fully screened in. Low-maintenance artificial turf keeps the backyard looking lush and green year-round without the need for mowing, while an additional mosquito repellent system enhances outdoor enjoyment. ***LOCATION: Perfectly positioned near Winter Park's acclaimed shopping, fine dining, beautiful parks, and vibrant cultural attractions, this exceptional location also offers effortless access to I-4 and Downtown Orlando, Winter Park Village, Publix, Trader Joe's, and much more, making it easy to enjoy everything Central Florida Lifestyle. Make an appointment today before this beautiful, amazing home is gone!!!

1737 Indiana Avenue, Winter Park

$2,100,000

Tuscania SubDv. ⋅ 32789 Zip Code

**A rare jewel in Winter Park's coveted Vias!** This oversized 0.36-acre lot (112' x 140') has been cleared and is ready for your custom estate home. Set on a charming brick street, it sits among multi-million dollar residences and lakefront estates, just steps from the Winter Park Racquet Club and close to Interlachen Country Club. Enjoy a quick drive to Park Avenue's boutiques and dining and the Winter Park 9 golf course. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. Opportunities to build in this sought-after neighborhood are few and far between, so bring your architect and your vision!

2036 Via Tuscany, Winter Park

700 Melrose Avenue Unit M23, Winter Park

$354,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park

$255,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park

330 W Morse Boulevard Unit 104, Winter Park

$1,379,000

Winter Park Comm SubDv. ⋅ 32789 Zip Code

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The interior space is professionally decorated with high end finishes and highly aesthetic. The turnkey floorplan offers open reception/waiting, full kitchen, bathroom, operating and pre-op rooms plus up to five private office spaces. Adjacent Unit 105 (separately listed in MLS) can also be purchased. Reserved parking spaces plus a wealth of street and public parking available nearby.

330 W Morse Boulevard Unit 104, Winter Park

328 W Morse Boulevard Unit 105, Winter Park

$1,420,000

Winter Park Comm SubDv. ⋅ 32789 Zip Code

An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The turnkey space is professionally decorated with high end finishes and highly aesthetic.Floorplan offers five multi-purpose office, three patient rooms, open reception/waiting, lounge/kitchen area and common restrooms (secure lobby). The adjoining/adjacent unit 104 can be combined with this unit (see separate listing for Unit 104 in MLS) for a total of 3652 hsf. Reserved parking spaces plus a wealth of street and public parking available nearby.

328 W Morse Boulevard Unit 105, Winter Park

$1,699,900

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Under Construction. Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringing warm contemporary design and effortless living to Winter Park. Offering 2,661 square feet, four bedrooms, three-and-a-half baths and a two-car garage, the home pairs a refined architectural presence with light-filled interiors and a highly considered floor plan. At the heart of the home, an expansive open-concept living space brings together the kitchen, dining and family areas for an easy sense of connection. The designer kitchen makes a statement with an oversized island, extensive cabinetry, integrated appliances and sophisticated finishes, while large windows and glass doors invite natural light throughout the main living areas. A first-floor guest suite offers added flexibility for visitors, a private office or multigenerational living. Upstairs, the primary suite is joined by two additional bedrooms, creating a comfortable separation between everyday living and private spaces. The primary retreat features a generous walk-in closet and a spa-inspired bath designed with a soaking tub, dual vanities and an oversized shower. Outside, the covered lanai extends the living space into the backyard, overlooking a private pool and landscaped surroundings, an inviting setting for relaxed afternoons, entertaining and year-round Florida living. With its soft neutral palette, natural textures, modern detailing and thoughtfully connected spaces, 2613 Lafayette Avenue offers a fresh take on new construction in Winter Park, sophisticated without feeling overly formal and designed for the way people live today. Ideally situated near the area’s dining, shopping, parks and everyday conveniences, the residence pairs the ease of new construction with the lifestyle and sense of place that make Winter Park so desirable.

2613 Lafayette Avenue, Winter Park

$325,000

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Welcome to 310 Granada Drive, an excellent opportunity to own a single-family home in the highly desirable Winter Park 32789 area. Situated in the established Fairview Heights community, this 3-bedroom, 2-bath concrete-block home offers 1,344 square feet of living space with a functional single-story floor plan and plenty of potential for a buyer looking to make a home their own. Inside, the home features tile flooring throughout the main living and dining areas, vaulted ceilings, ceiling fans, and a split-bedroom layout that provides added separation and flexibility. The kitchen is equipped with a convection oven, dishwasher, microwave, and refrigerator, while indoor washer and dryer hookups add everyday convenience. Step outside through the covered rear entry to a brick-paver patio overlooking the fully fenced backyard. Mature trees provide natural shade, while the outdoor space offers plenty of room for entertaining, gardening, pets, or simply enjoying the Florida lifestyle. A one-car carport provides covered parking, and the property is connected to public water and sewer. One of the property's biggest advantages is its Winter Park location. Enjoy convenient access to shopping, restaurants, parks, major roadways, downtown Winter Park, Park Avenue, College Park, and surrounding Orlando destinations while still coming home to an established residential neighborhood. With NO HOA, solid concrete-block construction, a fenced yard, and a sought-after 32789 address, 310 Granada Drive presents an exciting opportunity for an owner-occupant, investor, or buyer looking to renovate and add their personal style. Schedule your private showing and discover the possibilities this Winter Park property has to offer!

310 Granada Drive, Winter Park

100 S Interlachen Avenue Unit 401, Winter Park

$850,000

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

$169,900

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

LIVE THE WINTER PARK LAKEFRONT LIFESTYLE WITHOUT THE LAKEFRONT PRICE TAG! This UPDATED, GROUND-FLOOR 1-bedroom, 1-bath condo offers 645 SF of move-in-ready living in desirable Lakeside Manor on beautiful Lake Killarney. Enjoy easy first-floor access, peaceful park-like grounds, a sparkling lakefront pool, clubhouse, community boat access and docks—all just steps from your door. The location is exceptional—minutes from Winter Park Village, Park Avenue, Rollins College, shopping, dining and entertainment, with quick access to I-4 and Downtown Orlando. Perfect as a primary residence, second home or low-maintenance getaway. UPDATED. GROUND FLOOR. LAKEFRONT COMMUNITY. PRIME WINTER PARK LOCATION. Come see why Lakeside Manor remains one of Winter Park’s best-kept secrets!

2500 Lee Road Unit 123, Winter Park

$290,000

2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo SubDv. ⋅ 32789 Zip Code

Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park

$419,900

3 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Welcome to 712 Baffie Avenue, a charming and thoughtfully updated bungalow in one of Winter Park’s most sought-after areas. This home blends classic character with modern improvements, featuring beautiful hardwood floors, crown molding, a fireplace, and plenty of natural light throughout. The bright enclosed Florida room provides flexible space for a home office, sitting area, playroom, or additional entertaining space. The updated kitchen offers dark cabinetry, stone countertops, stainless steel appliances, and contemporary finishes. Major improvements include a brand-new roof installed in 2026, along with updated electrical, plumbing, and HVAC systems completed in 2025. These recent improvements provide added value and peace of mind for the next owner. The interior laundry room adds everyday convenience, while the covered rear porch creates a comfortable place to relax and enjoy the outdoors. The fenced backyard offers room for entertaining, gardening, pets, or creating a private outdoor retreat. Enjoy a prime location near A-rated schools, Dubsdread Golf Course, College Park, downtown Winter Park, AdventHealth, shopping, dining, and major roadways. With no HOA and easy access to some of Central Florida’s most popular neighborhoods, this home delivers the character, location, and major updates that make it stand out.

712 Baffie Avenue, Winter Park

$3,250,000

5 Beds ⋅ 6 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, this nearly 4,500 square-foot home pairs thoughtful design with exceptional indoor-outdoor living. An impressive entry foyer sets the tone for a residence filled with designer details and and a floor plan featuring five en-suite bedrooms, six full baths, and the convenience of two laundry rooms to serve each floor. At the heart of the home, the chef's kitchen is appointed with Thermador appliances and designed for every day living and entertaining. Expansive living spaces are anchored by an indoor fireplace, and flow seamlessly to the covered lanai, where a second fireplace, fully equipped outdoor kitchen and private pool create an exceptional setting for year-round Florida living. Outdoor lush tropical landscaping and striking gas lanterns give the home a distinctive sense of arrival and timeless curb appeal. An oversized garage provides generous space for vehicles and storage, while integrated smart-home features including cameras, alarm, smart switches, and speakers with Sonos, bring modern convenience throughout. Zoned for sought-after Audubon Park School and Winter Park High School.

2823 Parkland Circle, Winter Park

$850,000

Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code

Bring your vision to life in Winter Park. Situated on N Phelps Avenue, this approximately .24-acre property offers a rare opportunity to build new in an area surrounded by custom homes, luxury residences, and ongoing redevelopment. Offered for its land value, this property is well suited for builders, investors, developers, or anyone ready to create a home designed around their own style and needs. The 75-foot frontage with 140-foot depth provides flexibility for a variety of architectural designs and potential for outdoor living, a pool, and backyard space. With new construction continuing to reshape the surrounding area, 870 N Phelps presents an exciting opportunity to secure a sizable homesite and build from the ground up.

870 N Phelps Avenue, Winter Park

$2,500,000

5 Beds ⋅ 5 Baths ⋅ Jenkins Second Add SubDv. ⋅ 32789 Zip Code

Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-and-a-half bathrooms, this custom residence seamlessly blends striking contemporary lines with exceptional everyday functionality. The heart of the home is a culinary dream chef's kitchen, anchored by an oversized center island and premium quartz countertops. It comes fully equipped with custom 42-inch wood cabinetry, a dedicated walk-in pantry, and high-end appliances, including a 48-inch refrigerator, a 36-inch induction cooktop with a vented hood, a built-in microwave, a dishwasher, and double convection ovens. Entertain effortlessly in the adjacent formal dining room or mix drinks at the wet bar, which features a built-in wine chiller to keep your collection perfectly preserved. Designed for ultimate privacy, the first-floor primary suite serves as a peaceful sanctuary, complete with a spa-inspired bathroom featuring a spacious walk-in shower, a standalone soaking tub, and a thoughtfully organized his-and-hers walk-in closet with abundant storage. A generous guest retreat with a private full bath is also conveniently located on the main level. Ascend to the second floor to find soaring 11-foot ceilings and three additional well-appointed bedrooms, each designed with privacy and direct full-bath access in mind. Step through oversized sliding glass doors to transition into your private outdoor oasis, effortlessly expanding your living space into the open air. This smart-home-ready masterpiece comes equipped for integrated lighting, audio, and security, alongside pre-installed exterior accent lighting, security cameras, and a full-property irrigation system. Perfectly positioned for an elevated Florida lifestyle, this home is less than five minutes from the premier Interlachen Country Club, walking distance to Phelps Park, and just ten minutes from the world-class boutique shopping and fine dining along Park Avenue.

1760 Oakhurst Avenue, Winter Park

$140,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Welcome to this bright and beautifully updated second-floor condo located in one of Winter Park's most desirable communities! This 2-bedroom, 1-bathroom residence offers the perfect blend of comfort, modern upgrades, and an unbeatable location. Updated Kitchen: Features dark wood cabinetry, light quartz counter tops, black and stainless-steel appliances, a modern commercial-style faucet, and an in-unit washer/dryer set. Spacious Living & Bedroom Areas: Enjoy durable luxury vinyl plank flooring throughout the main areas, bright natural light, and modern finishes. Renovated Bathroom: Outfitted with a updated vanity, chic black hardware, and stylish lighting fixtures. Private Balcony: Relax outdoors on your private covered balcony with peaceful views of the lush green courtyard and community grounds. Resort-style sparkling swimming pool with expansive sun deck. Well-maintained grounds with mature landscaping and tropical palm trees. Quiet, well-kept building entrance and grounds. Situated right off Lee Road, you are just minutes away from top dining, shopping, and entertainment spots. Enjoy close proximity to Park Avenue in Downtown Winter Park, Rollins College, I-4 access for an easy commute to Downtown Orlando or major attractions. Local parks, lakes, and grocery stores. Whether you are looking for a primary residence or a strong investment opportunity in the booming Central Florida market, this move-in-ready condo is a must-see! Schedule your private tour today!

1695 Lee Road Unit C206, Winter Park

1250 S Denning Drive Unit 119, Winter Park

$265,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to easy, low-maintenance living in the heart of Winter Park! This beautifully updated 2-bedroom, 2-full-bath, first-floor corner residence at Mead Garden Condominiums offers a fresh, move-in-ready interior paired with an exceptional location just minutes from some of Winter Park’s most desirable destinations. Recent updates include new luxury vinyl flooring throughout the kitchen and great room, new carpeting in both bedrooms, fresh interior paint, and a recently redone screened-in porch with a refreshed frame and new screening. The thoughtfully updated kitchen features shaker-style cabinetry, granite countertops with breakfast bar, and stainless steel appliances. Additional features include remodeled bathrooms, low-Emissivity windows and sliding glass door, crown molding, updated baseboards and light fixtures, Nest thermostat, A/C replaced in 2018, and water heater replaced in 2019. Enjoy Florida living from the screened-in porch with convenient direct access to the community pool, onsite laundry facility, and mailroom. The first-floor corner location offers added privacy, comfortable single-level living, and a designated parking space.

1250 S Denning Drive Unit 119, Winter Park

$479,900

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park

$2,089,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts, this Louisiana-inspired 4-bedroom, 4-bath home pairs classic double-gallery porches with 3,479 sq ft of open, light-filled living in Winter Park's established Charmont neighborhood. Inside, rich hardwood floors, tray ceilings, crown molding and walls of French doors set the tone. The formal living and dining rooms open to a spacious great room and a chef's kitchen with an oversized granite island seating six, statement pendant lighting, stainless steel appliances, double wall ovens, abundant cabinetry, a walk-in pantry and a separate coffee/beverage bar with wine fridge. The main-level primary suite is a true retreat with a tray ceiling, French doors to the covered lanai, a custom walk-in closet and a spa bath with a freestanding soaking tub, dual vanities and a frameless glass shower. Upstairs, a large loft offers flexible space for a media room, gym or home office, with French doors to the second-story porch, along with generously sized secondary bedrooms. Step outside to your private backyard oasis: a covered lanai with outdoor kitchen, bar seating and ceiling fans overlooks the paver pool deck, sparkling pool with raised spa and fire bowls, all framed by mature landscaping and privacy fencing. Additional highlights include a laundry room with sink and cabinetry, a two-car garage and a paver driveway. Just half a mile from Audubon Park K-8, with Lake Baldwin Park, Mead Botanical Garden, East End Market, Baldwin Park Village and downtown Winter Park's shops and restaurants all close by, and about 4 miles to downtown Orlando.

1951 Winter Park Road, Winter Park

100 S Virginia Avenue Unit 201, Winter Park

$1,450,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

100 S Virginia Avenue Unit 201, Winter Park

$2,990,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-square-foot homesite in the fast growing Kenilworth Shores neighborhood. Striking curb appeal introduces the home, while a marble mosaic foyer provides an elegant first impression and leads into the expansive great room. At the center of the living space is a dramatic custom entertainment wall featuring illuminated built-in shelving and a sleek electric fireplace. The adjoining dining room is equally impressive, complete with an oversized dry bar, wine refrigerator, and glass-front cabinetry, creating the perfect setting for hosting family and friends. The designer kitchen makes a statement with Taj Mahal countertops, a marble mosaic backsplash, custom cabinetry, and a full suite of Thermador appliances, including a paneled built-in refrigerator. A massive butler’s pantry extends the kitchen’s functionality with abundant storage and preparation space, a second microwave and oven, and an additional dishwasher, making entertaining effortless. The downstairs primary suite offers a private retreat accented by warm wood beams and separate his-and-hers closets. Its jaw-dropping spa-inspired bathroom is wrapped in 12-by-24-inch marble tile and features dual vanities, a freestanding soaking tub, and an oversized walk-in shower with LED-illuminated niches. A dedicated home office is also located on the main level, providing a quiet and refined space for working from home. Upstairs, a massive bonus room creates a flexible second living area ideal for movie nights, a game room, or a children’s retreat. Four additional spacious bedrooms offer comfort and privacy for family and guests, while an upper-level balcony provides another inviting place to unwind. The outdoor living spaces are designed to take full advantage of the oversized lot. A large covered lanai with a complete summer kitchen overlooks the resort-style pool and spa, all framed by an elegant marble deck. Beyond the pool, the expansive backyard offers valuable green space for recreation, entertaining, or relaxation. Additional highlights include a complete impact-rated window and door package for added efficiency and peace of mind. Perfectly positioned near Cady Way Park, AdventHealth Winter Park, and just a golf-cart ride from Park Avenue, this extraordinary new residence presents a rare opportunity to experience uncompromising luxury, exceptional space, and the very best of the Winter Park lifestyle.

532 Langholm Drive, Winter Park

$1,890,000

4 Beds ⋅ 4 Baths ⋅ Parklando 03 SubDv. ⋅ 32789 Zip Code

PRICED BELOW APPRAISED VALUE | FULLY REMODELED WINTER PARK POOL HOME Pre-approval or proof of funds required in advance of showing. A rare opportunity to own more than 3,300 square feet of fully remodeled living space in Winter Park’s 32789 zip code, zoned for the highly sought-after Audubon Park School K–8 and Winter Park High School; all at a price below appraised value. Welcome to 2614 Parkland Drive, a completely reimagined luxury residence where sophisticated interiors meet resort-style Florida living. Extensively remodeled in late 2022 and topped with a brand-new architectural barrel tile roof, this home combines timeless character with modern finishes and major system upgrades. Inside, solid light-oak flooring, custom railings, and an open-concept layout create a warm, elevated feel throughout. The chef’s kitchen anchors the main living space with quartz countertops, full-height designer tile, abundant cabinetry, and a layout designed equally well for entertaining and everyday living. Step outside and the home transforms into a private resort. The custom heated pool and spa are finished in striking Caribbean-blue tile and surrounded by dramatic waterfalls, dual natural-gas fire features, porcelain privacy walls, and a built-in grill—creating an exceptional setting for entertaining or unwinding at home. The first-floor primary suite opens directly to the outdoor oasis. Upstairs, three oversized bedrooms are joined by a spacious loft and private patio; offering flexible space for family, guests, an office, or additional entertaining. Additional features include a brand-new barrel tile roof, dual tankless water heaters, central vacuum, natural-gas appliances, and extensive updates throughout. With more than 3,300 SF, a luxury pool and spa, extensive renovations, highly desirable school zoning, and a 32789 address, this home represents an exceptional opportunity in the Winter Park market. Luxury. Location. Lifestyle. And priced below appraised value.

2614 Parkland Drive, Winter Park

1602 Alabama Drive Unit 107, Winter Park

$1,150,000

2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park

$1,599,000

4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park

$1,250,000

3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE UNIQUE OPPORTUNITIES: Option 1 — $1,250,000 115' x 65' property + 65' lakefront. Option 2 — $1,450,000 155' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

$2,400,000

Killarney Estates SubDv. ⋅ 32789 Zip Code

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY! .39 acres: 17,100 sq ft (approx 24,000 sq ft: .55 acres including lakefront & street easement on both corner streets: 95 ft lakefront not included in FAR) Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead-end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE Optional OPPORTUNITIES: Option 1 — $1,450,000 155' x 65' property + 65' lakefront. Option 2 — $1,250,000 115' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

$3,545,995

4 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

The Art of Living Well: A New Chapter at "Moon Haus" Winterpark From the moment the custom 10-foot glass pivot door swings open, you realize this is not just a house—it is the life you have been envisioning. Designed and built as a true ground-up architectural revival, this residence delivers the pristine caliber, modern engineering, and turn-key experience of brand-new luxury construction. You step into the light-flooded foyer, and the outside world instantly quietens. Your eyes trace the subtle, warm grain of sleek Italian wood underfoot, drawing you effortlessly into a space crafted for both quiet contemplation and grand celebrations. Standing in the main living room, anchored by a dramatic statement fireplace, you can already picture it: crisp mornings spent with espresso in hand as gentle light filters through, and vibrant evenings filled with laughter as friends gather around. Every moment here feels orchestrated for ease. With a subtle tap, the home awakens around you. Music softly fills the air, lighting shifts to set a relaxed evening mood, and the climate adjusts seamlessly through the integrated Control4 system—an invisible concierge catering to your every preference. Moving into the kitchen, the space invites you to create. Light-toned European cabinetry conceals clever storage, while striking Neolith double countertops frame professional-grade Sub-Zero and Wolf appliances. It is a masterclass in culinary sophistication, whether you are hosting an intimate multi-course dinner party or savoring a slow, sun-drenched Sunday morning. When it is time to unwind, the home transitions into a private resort. You slide open the glass doors and step out onto the rich Brazilian IPE wood deck. The French gray mini-pebble pool glimmers ahead, warmed to perfection. At dusk, you fire up the sintered-stone summer kitchen under the Florida stars, preparing a meal al-fresco while the soft exterior lighting paints the lush, manicured grounds. At the end of the day, retreat to your en suite sanctuary. Each bedroom offers a secluded escape, but the primary suite feels like an exclusive boutique hotel. You step into the spa-inspired bath, surrounded by custom vanities, Neolith surfaces, and gentle ambient lighting, feeling a profound sense of calm. Set within one of Winter Park’s most coveted enclaves, just moments from the energy of Park Avenue, the prestigious Interlachen Country Club, and Phelps Park, this residence offers the rare opportunity to own a virtually new masterpiece in an established, iconic location. Experience the art of living well—connect with us today for an exclusive private tour!

1742 Temple Drive, Winter Park

1306 S Pennsylvania Avenue Unit 5, Winter Park

$349,000

2 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code

NEW PRICE! Charming Winter Park 2BR/1BA Condo with Lake Virginia Access! Beautifully renovated and ideally located near Park Avenue, Rollins College, Hannibal Square, and Mead Botanical Garden, this spacious second-floor condo combines architectural character with an unbeatable Winter Park lifestyle. Soaring cathedral/vaulted ceilings, hardwood floors, plantation shutters, custom built-ins, and French doors create a warm, cosmopolitan feel. The renovated kitchen features granite countertops, stainless-steel appliances, an induction range, bay window, and cozy dining nook. Spacious primary bedroom offers vaulted ceilings and French doors opening to a private screened outdoor space. Flexible second bedroom is ideal as a home office or guest room. Enjoy a private community dock with Lake Virginia access for kayaking, paddleboarding, or relaxing by the water. Expansive private deck overlooks picturesque Mead Gardens. Includes storage and garage space plus convenient in-unit laundry. Walk or bike to Park Avenue shops, restaurants, Rollins College, and everything that makes Winter Park so desirable!

1306 S Pennsylvania Avenue Unit 5, Winter Park

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