Winter Park Village Homes 

Winter Park Village, nestled in the heart of Winter Park, FL, is a charming and sought-after real estate destination offering an array of homes that blend modern comfort with timeless elegance. This upscale residential community boasts a diverse range of housing options, from cozy single-family homes to luxurious estates. Residents of Winter Park Village are treated to a unique blend of tranquility and convenience, as it is conveniently located near several attractions and amenities.

Surrounded by the allure of Winter Park's cultural scene, residents of Winter Park Village have easy access to nearby attractions such as the Charles Hosmer Morse Museum of American Art, which houses a stunning collection of Tiffany glass masterpieces, and the scenic Rollins College campus. Additionally, the community is a short drive away from Park Avenue, a bustling street lined with boutique shops, art galleries, and exquisite dining establishments. For nature enthusiasts, the serene Mead Botanical Garden provides a verdant oasis just moments away.

Complementing its attractions, Winter Park Village offers an array of nearby amenities, catering to residents' everyday needs. Essential services, supermarkets, and fitness centers are conveniently located within a stone's throw, ensuring that daily life is both comfortable and efficient. This harmonious blend of luxurious housing, cultural attractions, and practical amenities solidifies Winter Park Village's reputation as a prime destination for those seeking a sophisticated yet convenient Florida living experience.

Available Winter Park Village Homes For Sale

$1,795,000
4 Beds ⋅ 4 Baths ⋅ O6416565 MLS
Under contract-accepting backup offers. Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one. Step through the custom pivot front door into a home that immediately announces its intentions. Soaring 10-ft ceilings throughout rise to a dramatic 22-ft volume in the great room, framed by sliding glass walls that dissolve the line between interior living and the private outdoor retreat beyond. Level 5 smooth drywall finish — the standard reserved for the finest custom builds — runs throughout, while wide-plank hardwood flooring flows across every living area. Italian porcelain tile anchors all bathrooms and the laundry room with precision and permanence. Every window and exterior door is imported from Germany — Unilux® precision-engineered for thermal performance, acoustic excellence, and longevity that no domestic product can match. Grohe® plumbing fixtures, also made in Germany, carry that same philosophy through every bathroom. Countertops are Cambria or Silestone® quartz with a thickened 3cm mitered edge throughout. Custom solid wood cabinetry is built to plan in the kitchen, laundry, and all bathrooms, finished with Emtek® hardware and 8-ft solid core architectural doors with 7" baseboard throughout. The Winter Park Chain of Lakes — 12 interconnected lakes spanning 2,781 acres of pristine Florida waterways — is moments away, offering boating, paddleboarding, and the beloved Winter Park Scenic Boat Tour. Over 70 parks, Kraft Azalea Gardens, Mead Botanical Garden, and more than a dozen walkable green spaces define the outdoor lifestyle. The Winter Park Farmers' Market, held every Saturday at the historic train station, is a community institution. Rollins College, one of the South's most respected liberal arts institutions, sits lakeside just minutes away, bringing cultural programming, the Bach Festival, and vibrant intellectual energy to the neighborhood year-round. Families are served by highly rated Orange County public schools, with Winter Park High School renowned for its academic rigor and championship programs, as well as exceptional private options, including Trinity Preparatory School and St. Margaret Mary. New construction in 32789 is genuinely rare — historic preservation standards and limited land availability make it so. For international buyers, Orlando International Airport is 30 minutes south. Disney, Universal, and the theme park corridor are under 30 minutes via I-4. Atlantic beaches are under an hour away. This is not a production home dressed up with upgrades. It is a ground-up, custom-built, German-engineered, the most coveted zip code in Central Florida. Schedule your private showing today.

2501 Lafayette Avenue, Winter Park

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

$1,150,000
4 Beds ⋅ 4 Baths ⋅ O6412140 MLS
Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

1404 Border Drive, Winter Park

Courtesy of THE AGENCY FL

$1,599,000
4 Beds ⋅ 4 Baths ⋅ O6401352 MLS
Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

2430 Chantilly Avenue, Winter Park

Courtesy of ONE LUXURY INTERNATIONAL LLC

$589,000
3 Beds ⋅ 2 Baths ⋅ O6400395 MLS
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

Courtesy of GALLOWAY REAL ESTATE

$2,394,500
5 Beds ⋅ 7 Baths ⋅ O6381552 MLS
Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.

2412 Chantilly Avenue, Winter Park

Courtesy of REAL BROKER, LLC

Start Your Search

Provided courtesy of The Coastal Carolinas Association of REALTORS®. Information Deemed Reliable but Not Guaranteed. Copyright 2026 of the Coastal Carolinas Association of REALTORS® MLS. All rights reserved. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.

The Listings data contained on this website comes from various participants of The Multiple Listing Service of Greenville, SC, Inc. Internet Data Exchange. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The properties displayed may not be all the properties available. All information provided is deemed reliable but is not guaranteed. © 2026 Greater Greenville Association of REALTORS®. All Rights Reserved. Last Updated

“ Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Some IDX listings have been excluded from this website. Properties may or may not be listed by the office/agent presenting the information © 2026 Canopy MLS as distributed by MLS GRID”

Last Updated: board logo

Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.

board logoListings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work, please click here to review our DMCA policy and learn how to submit a takedown request. © 2026 FMLS. Last updated

Equal Housing Opportunity. All information contained herein deemed reliable but not guaranteed. Buyers should personally verify all information. All content Copyright 1998-2026 Great Smoky Mountains Association of Realtors. All rights reserved. Last updated .