Winter Park, FL Real Estate | Winter Park, FL Properties between $1,500,000 and $2,000,000 for Sale

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

$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

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code

Virtually Staged. Pre-Construction. To be built. POOL + SAUNA • DOUBLE PRIMARY SUITES • 3-CAR GARAGE • CUSTOM NEW CONSTRUCTION IN WINTER PARK Pool, sauna, double primary suites and a 3-car garage set the tone for this custom pre-construction residence planned for 2007 Edwin Blvd in Winter Park. Designed for elevated indoor-outdoor living, this 4-bedroom, 3.5-bath home brings together a flexible floor plan, distinctive amenities and carefully selected finishes in a new custom build. The double primary-suite configuration creates two dedicated primary retreats, adding versatility to the home’s layout. Interior specifications include 10-foot ceilings, Level 5 drywall finish, porcelain tile flooring, 5-inch baseboards, granite countertops and wood cabinetry. A dedicated butler pantry extends the kitchen with additional preparation, serving and storage space. Outdoor living is an integral part of the design, with a private pool and sauna incorporated into the planned residence. The 3-car garage provides generous vehicle and storage capacity, while the exterior architecture combines stucco and Hardie siding. The residence is planned with approximately 3,314 square feet under A/C and 4,111 total gross square feet, providing substantial interior and covered space while maintaining the functionality of the 4-bedroom layout. Located in Winter Park, the property offers convenient access to the Aloma Avenue corridor and surrounding restaurants, coffee shops, grocery stores, retail, parks and everyday services. Downtown Winter Park, Park Avenue, Central Park and Rollins College are also within the greater Winter Park area. For buyers searching for a new construction home in Winter Park with a pool, sauna, double primary suites, 3-car garage, butler pantry and custom finishes, 2007 Edwin Blvd brings these sought-after features together in one thoughtfully planned residence. Architectural plans, site plan and exterior elevations illustrate the proposed home, pool and garage configuration. Property is offered pre-construction. Final square footage, dimensions, materials, finishes and specifications are subject to final plans, builder selections and modifications. Schedule a private consultation to review the plans, proposed finishes and design details and explore the opportunity to make this custom Winter Park residence your next home.

2007 Edwin Boulevard, Winter Park

$1,950,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code

Under Construction. Set in Winter Park’s desirable Kenilworth Shores, this exceptional new residence blends timeless architecture, elevated finishes and thoughtfully designed interiors tailored to the modern Florida lifestyle, with anticipated completion by end of the year. Offering five bedrooms and four and a half baths, this property features a highly versatile floor plan with a first-floor primary suite and beautifully connected indoor and outdoor living. The main level is centered around an expansive open-concept kitchen and living area, complemented by a dedicated dining room that provides an elegant setting for more formal gatherings. The chef’s kitchen is appointed with a premium Thermador appliance package, generous central island and walk-in pantry, creating a highly functional setting for everyday living and entertaining. A nearby mudroom adds valuable storage and convenience. The spacious living room opens directly to the covered lanai, creating a seamless transition between interior and exterior. The first-floor primary suite offers a private retreat with a spacious bedroom, luxurious en-suite bath and expansive walk-in closet. A second bedroom and full bath are also on the main level, providing flexibility for guests, a private office or additional living space. Upstairs, three additional bedrooms are complemented by two full baths and a generous loft. The versatile loft can be tailored to a variety of needs, whether used as a media room, playroom, second lounge or workspace. A dedicated laundry room completes the upper level. Designed to embrace the Florida lifestyle, the covered lanai overlooks a private saltwater pool and spa, while the summer kitchen creates an inviting setting for outdoor dining and entertaining. The seamless connection between the main living areas and outdoor spaces makes the home equally suited to relaxed everyday living and effortless entertaining. Ideally in Winter Park, this residence is within the sought-after Brookshire Elementary, Glenridge Middle and Winter Park High School zones. Park Avenue’s renowned restaurants, boutique shopping, galleries and charming streetscape, along with AdventHealth Winter Park, are conveniently nearby. Cady Way Park is also nearby, offering a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and biking trails. With its combination of new construction, timeless design, premium appliances, flexible living spaces and exceptional indoor-outdoor flow, 513 Dunraven Drive presents a distinctive opportunity to experience Winter Park living. Private showings are being scheduled now.

513 Dunraven 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

$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

$1,550,000

6 Beds ⋅ 5 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most coveted premium lots, featuring a larger lot line, wooded HOA land behind the property, and serene views toward Lake Howell. The thoughtfully designed floor plan offers two primary suites, one on each level, plus a dedicated office, a theater room, a loft, and a three-car tandem garage with built-in shelving and a workbench. Designer finishes include Restoration Hardware and Pottery Barn chandeliers, plantation shutters, crown molding, motorized blinds, app-controlled LED trim lighting, and custom built-ins throughout the home. The resort-style backyard features a saltwater, solar-heated pool, expansive pool deck, motorized Sunpro awnings, landscape lighting, and lanai market lights—perfect for entertaining or relaxing in complete privacy. Additional upgrades include a custom entertainment center with an electric fireplace, a Sony theater system and projector in the media room, a water softener, gutters, and extensive custom storage solutions by Inspired Closets throughout the home. The hot tub, Paradise Grill, and custom workout equipment are also available for negotiation, offering the opportunity to make this already exceptional home truly turnkey for your lifestyle. Hawks Crest residents enjoy an impressive collection of community amenities, including a resort-style pool, splash pad, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. With highly regarded private schools nearby—including Park Maitland School, The Geneva School, Trinity Preparatory School, and The Master’s Academy—along with the exceptional shopping and dining of Park Avenue, this coveted Winter Park location truly offers the best of convenience, lifestyle, and luxury. Every box has been checked. From the premium homesite to the designer finishes, custom upgrades, resort-style pool, and thoughtful details throughout, this is a home where everything has already been done—just move in and enjoy.

1257 Wading Waters Circle, Winter Park

$1,550,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impressive curb appeal and graceful archways to the carefully selected finishes throughout, every part of this home was designed with purpose. The result is a residence that feels sophisticated and distinctive while remaining remarkably comfortable for everyday living. Striking from the moment you arrive, the home features beautiful archways, balanced architectural lines, and a timeless exterior that immediately sets it apart. Step inside to an open, light-filled floor plan with 10-foot ceilings, expansive windows, level 5 drywall, and designer lighting throughout.An open floor plan creates an easy flow between the main living spaces, with a fireplace anchoring the living room and the adjoining dining area opening directly to the outdoor entertaining space. At the center of the home is a Italian-inspired chef’s kitchen featuring custom cabinetry, designer countertops, a paneled refrigerator, and premium induction range.The primary suite offers a private retreat with a spacious bath complete with a freestanding soaking tub, oversized walk-in shower, and a large walk-in closet. Each secondary bedroom is generously sized and includes its own en-suite bath, providing privacy and convenience for family and guests, while the bonus room and additional storage provide added flexibility. The outdoor spaces are an extension of the home, with a covered patio, fully equipped summer kitchen, sparkling pool, and expansive backyard offering plenty of room for both entertaining and relaxing. Perfectly positioned in Winter Park, this home offers easy access to Park Avenue, exceptional dining and shopping, top-rated schools, and virtually everything you need just minutes from your front door. A rare opportunity to own a custom-designed home with exceptional architecture, quality construction, and a prime Winter Park location—all at an exceptional value.

2430 Chantilly Avenue, Winter Park

$1,600,000

3 Beds ⋅ 3 Baths ⋅ Albert Lee Ridge Annex SubDv. ⋅ 32789 Zip Code

WELCOME TO LAKEFRONT LUXURY ON LAKE BELL. This exceptional custom residence brings together refined craftsmanship and design, and an extraordinary waterfront setting in the heart of Winter Park. Built in 2025 by Accent Homes & Development, this beautifully appointed home offers 2,733 square feet of living space, with 3 bedrooms and 2.5 baths. From the moment you enter, expansive windows draw you toward the water, filling the home with natural light and creating a seamless connection between the elegant interiors and the lake beyond. Warm wood flooring flows throughout the main living areas, while a dramatic floor-to-ceiling fluted electric fireplace serves as a stunning architectural centerpiece, beautifully separating the living room from the formal dining area. At the heart of the home is a spectacular gourmet kitchen designed for both everyday living and effortless entertaining. Overlooking the lake, it features custom cabinetry, an oversized island, and an exceptional suite of premium appliances, including a 48-inch SUB-ZERO Classic French-door refrigerator, WOLF induction cooktop, WOLF wall oven and microwave, ELICA stainless steel under-cabinet hood, and BRISAS under-counter French-door wine cooler. Every detail reflects a thoughtful blend of luxury, functionality, and timeless style. Upstairs, the serene primary suite captures beautiful lake views and offers a spacious walk-in closet. Two additional bedrooms share a beautifully appointed Jack-and-Jill bath, with both bedrooms opening to a private balcony overlooking the tranquil surroundings. The true centerpiece of this property is its extraordinary waterfront lifestyle. Step outside to your own private covered dock on Lake Bell and enjoy direct access to a beautiful 36-acre, spring-fed ski lake. Lake Bell offers an exceptional setting for boating, water skiing, jet skiing, paddleboarding, kayaking, fishing, and swimming. Whether you're heading out on the water or simply relaxing dockside at sunset, every day feels like a getaway. With no neighbors directly across the lake, the property enjoys an uncommon sense of privacy, peacefulness, and expansive water views. Ideally located just 2 miles from I-4, this residence offers the best of Winter Park at your doorstep. Enjoy the boutiques, acclaimed restaurants, and timeless charm of Park Avenue, along with Winter Park Village, Rollins College, the Winter Park Farmers’ Market, Mead Botanical Garden, Kraft Azalea Garden, the Winter Park Chain of Lakes, museums, galleries, and historic neighborhoods—all just minutes away. A rare opportunity to own a newer built, custom lakefront residence with a private covered dock on one of Winter Park’s beautiful spring-fed lakes. Beautiful, serene, and designed for the way you want to live—this is Lakefront living at its finest.

2207 Kindel Avenue, Winter Park

$1,875,000

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

Set along one of Winter Park’s charming brick streets just steps from Park Avenue, this beautifully maintained home pairs refined design with an exceptional location. Impressive curb appeal sets the tone, while thoughtfully curated interiors create a home that feels both elevated and inviting. Inside, the main living space centers around a custom entertainment wall with built-in shelving and an electric fireplace. The adjoining kitchen is equally impressive, featuring quartz countertops, a statement La Cornue range, paneled refrigerator, and a cleverly hidden walk-in pantry. A sun-filled breakfast nook provides a casual dining space, while sliding glass doors create a seamless connection to the outdoor living areas. For larger gatherings, the spacious formal dining room offers an elegant setting for entertaining, and a well-designed mudroom and laundry combination adds everyday functionality. The primary suite is a private retreat with generous proportions and a beautifully appointed spa-inspired bath. A custom trough-style sink, separate makeup vanity, oversized walk-in shower, freestanding soaking tub, and expansive walk-in closet create a space that feels luxurious yet highly functional. Two additional bedrooms are both ensuite, offering privacy and comfort for family and guests. Outdoors, the home truly impresses. A lush wall of mature bamboo surrounds the backyard, creating an unexpected sense of privacy just moments from the heart of Winter Park. The resort-style pool features a sun shelf and built-in seating, while a pergola provides the perfect setting for al fresco dining and relaxed evenings outdoors. For the car enthusiast there is a car lift in the garage allowing for storage of up to 3 vehicles. The location is difficult to match, just steps from the shops, restaurants, and energy of Park Avenue and minutes from Hannibal Square, Winter Park Village, Park Maitland School, and the Enzian Theater. Beautifully maintained, thoughtfully designed, and positioned in one of Winter Park’s most desirable locations, this is a rare opportunity to enjoy an exceptional lifestyle in the heart of it all.

751 Pansy Avenue, Winter Park

$1,999,900

32792 Zip Code

A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park

$1,699,000

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

This modern and sleek Winter Park residence, with over $130K of improvements, is tucked along a quiet dead-end street, offering a functional, open floorplan in an exceptional location. Recent upgrades make this home feel wonderfully fresh and new, including a Mosquito Nix misting system, Culligan whole-home water filtration system, fresh paint throughout the entire home, a beautifully remodeled spa-inspired Primary bathroom, renovated powder room, Lutron smart dimmer switches with upgraded LED lighting, a custom-built marble fireplace wall…and the list goes on! Offering 4 bedrooms and 3.5 bathrooms, with a dedicated office, upstairs loft area, and the potential for two laundry rooms (upstairs is a converted kitchenette), this home masterfully pairs modern design with comfortable everyday living. A soaring 20-foot foyer makes for an impressive introduction, with a private home office just off the entry. The open-concept living spaces center around a sleek chef’s kitchen with an oversized 8.5-foot island, quartz countertops, Thermador appliances, a 6-burner gas range with stainless steel hood, wine refrigerator, and deep corner pantry. The adjoining dining and living areas enjoy views of the pool and spacious backyard, while a newly added electric fireplace with a custom marble wall creates a stunning focal point. The enormous 1st floor Primary Suite has undergone an extensive remodel, including custom walk-in closets with a built-in wall safe, a new floating dual vanity with an anti-fog LED mirror, and an upgraded walk-in shower with a new privacy/glass combination wall, multiple shower heads, and a new freestanding soaking tub. Upstairs, a loft area offers tremendous versatility and connects 3 additional bedrooms, all with new modern LVP flooring (NO carpet) and walk-in closets. Two bedrooms share an updated hall bath with new marble flooring and a fabulous mirror. The 4th bedroom is privately positioned on the opposite side of the home with an en-suite bath and French doors leading to a private balcony. The former upstairs utility space has been thoughtfully transformed into a kitchenette with custom cabinetry, new countertops, a utility sink, and a built-in microwave. This area is especially valuable for extended stays or a secondary living arrangement. A custom work/study area was also added to the rear bedroom, but easy to remove! Outside, the fully fenced backyard is lined with a lush bamboo wall and majestic palms, creating a private retreat with a saltwater pool, covered lanai, and ample remaining space for pets or outdoor entertaining. The covered lanai and pool area provide convenient access to the powder bath, recently renovated with gorgeous, marbled floor-to-ceiling tile. The 2-car garage features wall-mounted shelving, multiple overhead storage racks, and durable flooring, plus the frosted glass garage doors add natural light. The sellers partnered with Terra Energy to install solar panels on the roof, providing significant savings on their electric bill. (This fantastic subscription service is $186/month with the solar panel company, and additional information will be provided!) With its contemporary architecture, flexible floorplan, substantial recent investments, and highly coveted location, 2343 Versailles Avenue offers the rare combination of newer construction and extensive upgrades in the heart of Winter Park.

2343 Versailles Avenue, Winter Park

$1,699,000

4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet of open-concept living space, the home features four bedrooms and three-and-a-half lavish bathrooms. Framed by hand-selected architectural stone, the elegant entryway reveals a luminous interior anchored by wide-plank light oak flooring that flows seamlessly across both levels. At the heart of the home, the chef’s kitchen boasts a premium Thermador appliance suite, custom Fabuwood shaker cabinetry, vein-matched quartz countertops, a custom pot-filler, and a wine refrigerator. The main-level primary suite offers a true private sanctuary, highlighted by a spa-inspired bath with a freestanding soaking tub, gold-brushed hardware, and a frameless glass walk-in shower. Dissolving the boundaries between indoors and out, the main living area opens to an expansive covered lanai complete with a summer kitchen and a built-in grill. This alfresco retreat overlooks a private, resort-style backyard centered around a saltwater pool, perfectly designed for relaxation or grand-scale entertaining. Zoned for Audubon K-8 and Winter Park High School, and located just minutes from Park Avenue, Trinity Prep, and Lake Highland, this residence presents an unparalleled opportunity for elevated luxury in one of Central Florida’s most exclusive locations.

2308 Mulbry Drive, Winter Park

$1,625,000

5 Beds ⋅ 5 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and stunning hardwood floors that flow throughout the main level and continue upstairs into the loft and primary suite. The thoughtfully designed floor plan includes a downstairs bedroom and full bath, ideal for guests, in-laws, or a private home office. Designed with the entertainer in mind, the gourmet kitchen is a true showstopper—featuring quartz countertops, an oversized island, Jenn Air appliances including a double oven, and generous cabinet space. A large butler’s pantry with an additional sink offers even more storage and prep space. Seamlessly transition from indoor to outdoor living with the sliding glass doors that open to a covered lanai, private pool, and expansive fenced in backyard—perfect for relaxing or hosting gatherings year-round. Upstairs, the luxurious primary suite includes a walk-in closet and a spa-like bathroom with dual sinks, a soaking tub, and a separate walk-in shower. Three additional bedrooms, two full bathrooms, and a spacious laundry room with more storage complete the upper level. Additional features include a dedicated mudroom with built-in bench seating and storage, and an air-conditioned two-car garage with insulated doors and epoxy floors. All of this, just minutes from the Winter Park Racquet Club, Park Avenue’s boutique shopping and dining, and top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. Don’t miss this rare opportunity to own a one-of-a-kind home in one of Winter Park's premier neighborhoods.

2407 Lafayette Avenue, Winter Park

$1,725,000

4 Beds ⋅ 4 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community. Offering nearly 3,800 sq. ft. of sophisticated yet comfortable living space, this 4-bedroom, 3.5-bath residence combines timeless architectural details—including soaring vaulted ceilings, crown molding, and dark hardwood floors—with the ultimate layout for functional living. An inviting foyer with volume ceilings and a large transom window fills the home with natural light, leading into a spacious family room anchored by a marble-wrapped electric fireplace with custom lighting and a media niche. The chef’s kitchen is open, bright, and ideal for entertaining, featuring 42-inch shaker double-stacked cabinetry, premium Bosch stainless steel appliances, granite countertops, a designer backsplash, a large pantry, and peninsula bar seating alongside an eat-in breakfast nook. Seamlessly connected, the formal dining room shines with a tray ceiling, custom wallpaper, and designer fixtures. Convenience continues in the oversized laundry room, equipped with a second refrigerator and secondary pantry. Designed for total flexibility, the main level features a dedicated executive office, a media room, a secondary guest suite, and a lavish primary retreat. The primary suite boasts custom built-ins, a massive walk-in closet, direct outdoor access, and a spa-inspired bath with double vanities, a soaking tub, and a large dual-head shower. Upstairs, you’ll find two additional spacious bedrooms, a full bath, and a versatile bonus loft. Outside, a private resort oasis awaits with an open-air lanai and covered porch for alfresco dining, surrounded by lush mature landscaping, pathways trimmed with turf grass, and professional landscape lighting. The heated pool and spa feature a sun shelf with a fountain feature and linear fire elements along the edge that transform the backyard at night. Completing the estate is a 3-car total garage layout, featuring an attached 2-car garage plus a separate detached structure with guest house, studio, or private office potential. Located just one mile from historic Park Avenue, zoned for top-rated schools (Lakemont Elementary, Glenridge Middle, Winter Park High), and walkable to Phelps Park, the YMCA, and local dining.

1840 Bryan Avenue, Winter Park

$1,800,000

5 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 02 SubDv. ⋅ 32789 Zip Code

Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.

281 Brewer Avenue, Winter Park

$1,999,900

3 Beds ⋅ 2 Baths ⋅ 32792 Zip Code

Price improvement. A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park

$1,600,000

4 Beds ⋅ 4 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, stainless steel appliances, ample amount of cabinetry and counter space, and a breakfast bar, great for entertaining family and friends. Open floor plan. Home features a separate dining area off the kitchen. Spacious living space and bedrooms. Spend your evenings and weekends relaxing on the beautiful lakefront of Lake Killarney, enjoying the incredible sunsets under the shade of huge cypress trees OR poolside in the private fenced in backyard.

250 Killarney, Winter Park

$1,795,000

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

$1,995,000

Lake Sylvan Shores SubDv. ⋅ 32789 Zip Code

Exceptional opportunity to build your dream home in one of Winter Park’s most sought-after neighborhoods! This cleared, vacant homesite is ready for construction and offers the perfect canvas to create a custom residence tailored to your vision. Nestled on a quiet street, the property is surrounded by beautiful homes while providing convenient access to Park Avenue’s renowned shopping and dining, Rollins College, top-rated schools, parks, golf courses, and major roadways. Whether you’re a builder, investor, or future homeowner, this is a rare chance to secure a prime piece of land in an established community where new construction opportunities are increasingly limited. Don’t miss the chance to bring your vision to life in the heart of Winter Park!

1415 Grove Terrace, Winter Park

101 S New York Avenue Unit 311, Winter Park

$1,775,000

3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park

$1,595,000

Tuscany Terrace SubDv. ⋅ 32789 Zip Code

Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue's renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted "Vias" of Winter Park, a collection of streets long regarded as one of the city's most established and desirable residential enclaves. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end users alike - a rare chance to secure one of winter Park's most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$1,999,900

5 Beds ⋅ 5 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

240 N Phelps Avenue, Winter Park

$1,599,000

5 Beds ⋅ 4 Baths ⋅ Fremar SubDv. ⋅ 32789 Zip Code

Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.

1864 Grinnell Terrace, Winter Park

$1,550,000

4 Beds ⋅ 4 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code

Under Construction. Under Construction Buyer Incentive Limited time - Choose from $30,000.00 cash credit or $40,000 credit towards upgrades. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. Design book is available upon request. Please inquire for details and customization options.

901 Enclave Place, Winter Park

$1,550,000

4 Beds ⋅ 4 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code

Under Construction. Under Construction Buyer Incentive Limited time - Choose from $30,000.00 cash credit or $40,000 credit towards upgrades.The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located, walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.

905 Enclave Place, Winter Park

$1,595,000

3 Beds ⋅ 2 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$1,750,000

4 Beds ⋅ 3 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops, custom cabinetry, and stainless steel appliances, perfect for both everyday living and entertaining. Step outside to the private lanai, where you can enjoy a summer kitchen, pool, and lushly landscaped backyard, creating an ideal indoor-outdoor lifestyle. From the moment you enter, the home is filled with warm natural light and high-quality finishes throughout, creating a welcoming atmosphere. The primary bedroom is conveniently located on the first floor, offering privacy and comfort along with an inviting, functional layout. The second floor features three additional bedrooms, two bathrooms, and two expansive terraces, perfect for relaxation or entertaining. Located just minutes ( 1.25 Miles ) from Park Avenue Restaurants and shopping district, 15 min from Downtown Orlando, and an array of fine dining, boutique shopping, museums, and local cafés, this exceptional home offers modern luxury in an unbeatable location.

1840 Anzle Avenue, Winter Park

Winter Park, FL Properties between $1,500,000 and $2,000,000 for Sale

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