Winter Park Village Real Estate

Winter Park Village Real Estate

Welcome to Winter Park Village, a vibrant and picturesque subdivision nestled in the heart of Winter Park, Florida. Known for its charming tree-lined streets and a strong sense of community, Winter Park Village offers a unique blend of suburban tranquility and urban convenience. This delightful area is situated in Orange County, just a stone's throw away from the cultural richness of downtown Winter Park.

Winter Park Village is renowned for its stunning residential options, ranging from modern townhomes to elegant single-family houses, all designed to cater to a variety of lifestyles. The architectural styles reflect the area's historical charm, with many homes featuring traditional Florida elements that seamlessly blend with contemporary finishes. Residents enjoy spacious yards, lush landscaping, and a friendly neighborhood atmosphere, making it the perfect place to call home.

Beyond the beautiful residences, Winter Park Village is a hub for leisure and recreation. The nearby parks offer ample opportunities for outdoor activities, including walking trails, playgrounds, and picnic areas, perfect for families and nature lovers alike. The area is also home to an array of shopping, dining, and entertainment options, ensuring that everything you need is just a short drive or stroll away.

With its excellent schools, community events, and welcoming spirit, Winter Park Village is not just a place to live; it’s a lifestyle. Whether you’re looking for a peaceful retreat or a vibrant community, Winter Park Village invites you to discover the charm and excitement of this extraordinary neighborhood. Come and experience the warmth and beauty of Winter Park Village—your dream home awaits!

Newest Listings in Winter Park Village

$1,598,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impressive curb appeal and graceful archways to the carefully selected finishes throughout, every part of this home was designed with purpose. The result is a residence that feels sophisticated and distinctive while remaining remarkably comfortable for everyday living. Striking from the moment you arrive, the home features beautiful archways, balanced architectural lines, and a timeless exterior that immediately sets it apart. Step inside to an open, light-filled floor plan with 10-foot ceilings, expansive windows, level 5 drywall, and designer lighting throughout.An open floor plan creates an easy flow between the main living spaces, with a fireplace anchoring the living room and the adjoining dining area opening directly to the outdoor entertaining space. At the center of the home is a Italian-inspired chef’s kitchen featuring custom cabinetry, designer countertops, a paneled refrigerator, and premium induction range.The primary suite offers a private retreat with a spacious bath complete with a freestanding soaking tub, oversized walk-in shower, and a large walk-in closet. Each secondary bedroom is generously sized and includes its own en-suite bath, providing privacy and convenience for family and guests, while the bonus room and additional storage provide added flexibility. The outdoor spaces are an extension of the home, with a covered patio, fully equipped summer kitchen, sparkling pool, and expansive backyard offering plenty of room for both entertaining and relaxing. Perfectly positioned in Winter Park, this home offers easy access to Park Avenue, exceptional dining and shopping, top-rated schools, and virtually everything you need just minutes from your front door. A rare opportunity to own a custom-designed home with exceptional architecture, quality construction, and a prime Winter Park location—all at an exceptional value.

2430 Chantilly Avenue, Winter Park
$660,000
Winter Park Village SubDv. ⋅ 32789 Zip Code
An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market and the chain of lakes are all a short drive away. Property sold as is. The buyer is to verify setbacks, utilities, impact fees, demolition requirements and permitted building dimensions with the City of Winter Park.

1416 Border Drive, Winter Park
$660,000
3 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market and the chain of lakes are all a short drive away. Property sold as is. The buyer is to verify setbacks, utilities, impact fees, demolition requirements and permitted building dimensions with the City of Winter Park.

1416 Border Drive, Winter Park
$1,749,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brings contemporary design and elevated living to one of Winter Park's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and 2,715 square feet of thoughtfully designed living space, the home blends clean architectural lines with warm, inviting interiors designed for both everyday living and effortless entertaining. The open-concept floor plan is filled with natural light and seamlessly connects the main living areas, creating a spacious and functional layout. Designer finishes, sophisticated details, and carefully selected materials elevate every space, while the chef-inspired kitchen serves as the heart of the home. Step outside to your private backyard retreat featuring a resort-style pool and spa, providing the perfect setting for relaxing or entertaining year-round. Ideally located just minutes from Park Avenue, residents will enjoy easy access to award-winning dining, boutique shopping, parks, golf courses, and Winter Park's vibrant cultural scene.

2525 Lafayette Avenue, Winter Park
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
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
$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
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