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

5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park

$490,900

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

Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward. Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location and a home that is ready to be enjoyed from day one while maintaining long term upside.

525 Ololu Drive, Winter Park

$1,595,000

4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

$995,000

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

HUGE PRICE IMPROVEMENT!!Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — every step of this rennovation was completed with quality and permanence in mind. With elevated finishes, like designer tile and quartz countertops, beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.

1611 Chestnut Avenue, Winter Park

$1,185,999

6 Beds ⋅ 4 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.

726/720 N Pennsylvania Avenue, Winter Park

$1,795,000

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

Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

106 S Interlachen Avenue Unit 518, Winter Park

$589,000

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

Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

1319 Bessmor Road, Winter Park

$540,000

3 Beds ⋅ 3 Baths ⋅ Townhomes/Harper Place SubDv. ⋅ 32789 Zip Code

Welcome to easy living in the heart of Winter Park. This beautifully bright end unit townhome offers 1,660 square feet of comfortable, move-in-ready living space with no carpet throughout. New luxury vinyl plank flooring was installed in August 2026 and includes a one-year transferable workmanship warranty. The main level offers a versatile layout with two distinct living areas, including a spacious living and dining combination and a separate family room. The well-appointed kitchen features a natural gas cooktop and range, granite countertops, center island, breakfast nook, and built-in cabinetry with a convenient desk area. French doors open to a private, fully fenced patio, creating an inviting outdoor space ideal for grilling, entertaining, or gardening. An interior laundry room provides added convenience and leads directly to the two-car garage. Upstairs, the spacious primary suite features a walk-in closet and walk-in shower. Two additional bedrooms provide comfortable accommodations and flexible space for guests, a home office, or other needs.Recent major updates include the roof and gutters (2022), exterior paint (2023), water heater (2023), and AC (2024), which also includes a transferable service agreement. The HOA provides added peace of mind by covering exterior building insurance, grounds and road maintenance, and reserve funding. Ideally located near I-4, Winter Park’s renowned restaurants and shops, hospitals, museums, and everyday conveniences, this townhome combines thoughtful updates, functional living spaces, and an exceptional location.

1261 Indiana Avenue, Winter Park

$349,000

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

Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those looking to build their dream home in a prime location. Situated in the sought-after Dubsdread Heights neighborhood, this home is just minutes from downtown Winter Park, College Park, and Orlando’s vibrant dining, shopping, and entertainment districts. The property’s spacious lot offers room for expansion, renovation, or new construction, making it a rare opportunity in one of Central Florida’s most desirable zip codes. Whether you’re a first-time buyer, an investor seeking value-add potential, or someone looking to customize a home in a premium location, this property delivers both charm and opportunity. With strong surrounding home values and continued growth in the area, 811 Overspin Drive is an excellent chance to invest in the future of Winter Park living. Don’t miss your opportunity to own in one of Central Florida’s most sought-after communities!

811 Overspin Drive, Winter Park

$529,000

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

In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park

$3,995,000

4 Beds ⋅ 6 Baths ⋅ Winflor Court Pt Rep SubDv. ⋅ 32789 Zip Code

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

1441 Cardinal Court, Winter Park

$439,000

3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge 1st Add SubDv. ⋅ 32789 Zip Code

Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful retreat located in the highly desirable and vibrant community of Winter Park. Preferred lender credit available.

950 Hanover Avenue, Winter Park

$1,049,000

5 Beds ⋅ 3 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

2702 Parkland Drive, Winter Park

$2,689,000

Sicilian Shores SubDv. ⋅ 32789 Zip Code

Valuable architectural and interior design plans (being offered with the list price!) are available to provide a jump start on your stunning new custom home. Click the VIRTUAL TOUR LINK for a short video showing this lot's true potential, and see photos for a proposed site plan & renderings! One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Via’s, this .48-acre homesite is cleared and ready to build, offering a fantastic combination of a prime location and a spacious lot, surrounded by gorgeous homes on a lakefront street. The current owners have thoughtfully commissioned architectural plans by renowned Winter Park architect Gary Hancock, in which every detail and luxurious finish was meticulously designed with impeccable taste. While plans are being offered, buyers also have the flexibility to bring their own vision to life. Ideally located just minutes from Park Avenue and surrounded by some of Winter Park’s most beautiful lakefront homes, this homesite also enjoys close proximity to the Winter Park Racquet Club, Kraft Azalea Garden, Phelps Park, and the Winter Park YMCA. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High, this is truly a special opportunity to create a custom residence in one of Winter Park’s most coveted settings.

620 Pinetree Road, Winter Park

$1,350,000

South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Lakefront home on over 1 acre in Winter Park with approximately 95 feet of frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot widens toward the water, creating an exceptional setting for outdoor living, privacy, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly special. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park

$1,350,000

3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy, nature, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly exceptional. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park

$108,000

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

Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area of Winter Park close to tons of and amenities.

1695 Lee Road Unit D211, Winter Park

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

1870 Staunton Avenue, Winter Park

$1,770,000

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

Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!

621 Huntington Avenue, Winter Park

$1,640,000

4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functionality. Freshly painted throughout and move-in ready, the home features an open and inviting floor plan filled with natural light and high-end finishes. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, gas range, center island with breakfast bar, and 42” cabinetry with crown molding, all overlooking the spacious family room with gas fireplace and French doors leading to the pool and outdoor living area. The first-floor primary suite offers private French door access to the pool, a generous walk-in closet, and a luxurious bath featuring dual vanities, jetted soaking tub, and a large walk-in shower. Upstairs you will find three additional bedrooms, a large bonus room (easily convertible to a fifth bedroom), two balconies, and a convenient wet bar, creating a perfect space for guests, family living, or entertainment. Additional interior highlights include travertine flooring on the main level, tray ceilings, solid wood doors, extensive crown molding, built-in closet shelving, updated lighting, and dual tankless energy-efficient gas water heaters. The private outdoor area is designed for Florida living with a heated saltwater pool and spa, outdoor shower, summer kitchen hookups, and spacious green yard ideal for relaxing or entertaining. This exceptional property offers a rare opportunity to enjoy luxury living in one of Winter Park’s most desirable locations.

1570 Palmer Avenue, Winter Park

$2,650,000

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

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.

541 W Canton Avenue, Winter Park

$1,780,000

4 Beds ⋅ 4 Baths ⋅ Green Terrace V/140 Lot 3 Blk B SubDv. ⋅ 32789 Zip Code

Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

1750 Carollee Lane, Winter Park

$1,675,000

4 Beds ⋅ 4 Baths ⋅ Twin Acres SubDv. ⋅ 32789 Zip Code

Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home features floor-to-ceiling glass, a wraparound terrace, and a bold two-story façade. The quartz river rock and concrete drive leads to dual frosted glass garage doors, pre-wired for an EV charger. Inside, a dramatic floating staircase is framed by a 17’ window, anchoring the open-concept living space with views of the private backyard. The modern kitchen includes light gray touch-open cabinetry, soft-close drawers, black stainless appliances, and a Calacatta quartz waterfall island. The outdoor space is designed for entertaining, with a covered lanai, expansive marble terrace, and a mini-pebble pool with sun shelf and water features. Lush podocarpus hedging and a masonry wall provide privacy. The first floor offers a dedicated office and full pool bath. Upstairs features four bedrooms with Italian frameless doors and three European-inspired bathrooms. The primary suite includes a custom walk-in closet and private access to the wraparound terrace overlooking the pool. Surrounded by beautiful tree-lined streets ideal for strolling and golf-cart rides to nearby shops, restaurants, and friends’ homes, this property offers the best of the Winter Park lifestyle. The home is also zoned for top-rated Winter Park schools. A rare modern home in one of Winter Park’s most desirable locations. Call today for your private showing.

1903 N Park Avenue, Winter Park

$918,000

4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.

Lot #21 Karolina Ave, Winter Park

$3,275,000

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

Virtually Staged. This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

1581 Forest Avenue, Winter Park

$574,900

3 Beds ⋅ 2 Baths ⋅ Metzingers Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

1354 Indiana Avenue, Winter Park

$6,900,000

6 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

1260 Alabama Drive, Winter Park

$820,000

5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park

$7,250,000

5 Beds ⋅ 6 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code

Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

40 Palmer Avenue, 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

$1,380,000

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

Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

1751 Goodrich Avenue, Winter Park

$695,000

4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code

A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

432 W Swoope Avenue, 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

$1,400,000

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

BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

1523 Miller Avenue, Winter Park

$184,900

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

Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

2500 Lee Rd. Unit 222, Winter Park

$459,900

Golfview SubDv. ⋅ 32789 Zip Code

Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a top-rated school district, including Princeton Elementary. A rare opportunity in Winter Park—don’t wait to make this exceptional property yours.

3601 Midiron Drive, Winter Park

$899,000

Fairbanks Park SubDv. ⋅ 32789 Zip Code

Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and entertainment. Lots like this are seldom available. Whether you’re envisioning a custom residence or an investment in one of Central Florida’s most desirable neighborhoods, this is a truly rare opportunity in the heart of Winter Park.

731 Midget Drive, Winter Park

$629,900

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

RENT TO OWN OPTION AVAILABLE!!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$899,000

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$285,000

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit #115, Winter Park

$2,195,000

5 Beds ⋅ 4 Baths ⋅ Lugano Terrace SubDv. ⋅ 32789 Zip Code

Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

1885 Temple Drive, Winter Park

$629,900

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

RENT TO OWN OPTION AVAILABLE!!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$3,650,000

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

Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

207 E Kings Way, Winter Park

$3,075,000

5 Beds ⋅ 6 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

1821 Englewood Road, Winter Park

$279,000

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park

$4,500,000

Winter Park SubDv. ⋅ 32789 Zip Code

RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses. Future residents will enjoy picturesque walks along Winter Park's famous brick streets just off the shores of the chain of lakes. Nearby attractions like the Winter Park Farmer's Market, the Winter Park Golf Course, a highly rated 9-hole gem in the center of town, Casa Feliz, Central Park, and more are all within just a few minutes stroll.

503 N Interlachen Avenue, Winter Park

$299,999

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

151 N Orlando Avenue Unit 118, Winter Park

$205,000

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

1695 Lee Road Unit C202, Winter Park

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