Winter Park Homes for Sale

Winter Park Homes for Sale

Welcome to Winter Park, Florida—a picturesque suburban oasis nestled in Orange County, just a stone's throw from the vibrant pulse of Orlando. Known for its charming tree-lined streets and stunning lakes, Winter Park offers a unique blend of small-town warmth and big-city convenience. With its rich history, cultural attractions, and a strong sense of community, this enchanting area is a perfect place to call home.

Winter Park is renowned for its beautifully maintained parks, scenic canals, and the renowned Rollins College, which adds a youthful energy to the community. The historic Park Avenue is lined with boutique shops, gourmet restaurants, and art galleries, making it a delightful destination for both residents and visitors. Enjoy leisurely strolls along the picturesque lakes or partake in the many festivals and events that celebrate the arts and local culture throughout the year.

When it comes to homes for sale in Winter Park, the options are as diverse as the community itself. From charming bungalows and modern townhomes to luxurious estates, there’s something to suit every lifestyle and budget. Many properties boast stunning architectural details, spacious yards, and proximity to top-rated schools. Whether you're a first-time homebuyer or looking to upgrade, Winter Park's real estate market offers a wealth of opportunities.

Discover the charm and elegance of Winter Park—where community spirit thrives, and every day feels like a vacation. Let us help you find your dream home in this idyllic corner of Florida!

Newest Winter Park Homes for Sale

no property photo
$4,695,000
11 Beds ⋅ 8 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision. From the moment you arrive, the classic Spanish Revival influence and established setting offer a sense of history and individuality rarely found in newer construction. The multiple buildings create exciting possibilities for guest accommodations, private home offices, studios, hobby spaces, entertaining areas, or other uses permitted by applicable zoning and regulations. The residence offers an opportunity to preserve its distinctive architectural character while updating and personalizing the interiors and amenities for today's lifestyle. For buyers who appreciate homes with a story, architectural distinction, and the potential to make a property uniquely their own, this estate stands apart from the typical Winter Park offering. Even more compelling is the location. The property is within walking distance of Winter Park's famous Park Avenue, renowned for its restaurants, boutiques, cafes, galleries, cultural attractions, and unmistakable charm. Enjoy the rare opportunity to leave the car at home and stroll to one of Central Florida's most celebrated dining, shopping, and entertainment destinations. Rollins College is also nearby, while convenient access to downtown Orlando combines the charm and sophistication of Winter Park with easy connectivity to the greater Orlando area. The property is not individually listed on the Winter Park Register of Historic Places and is not located within a locally designated historic district, an important consideration for buyers exploring future renovation and personalization plans. Buyers should independently verify applicable zoning, permitting, building, and preservation requirements for any intended improvements or uses. With its James Gamble Rogers II design, 1929 origins, Spanish Revival character, approximately half-acre setting, substantial combined square footage, three accessory buildings, and an outstanding location within walking distance of famous Park Avenue, 617 N Interlachen Ave is far more than a conventional home purchase. It is an opportunity to take a distinctive piece of Winter Park architecture and shape its next chapter. Bring your vision and discover the possibilities where history, architecture, location, and potential come together in a truly one-of-a-kind Winter Park estate.

617 N Interlachen Avenue, Winter Park
540 N Pennsylvania Avenue, Winter Park
$3,950,000
4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS VACANT LAND WITH THE MLS #O6431538.

540 N Pennsylvania Avenue, Winter Park
471 Holt Avenue, Winter Park
$950,000
4 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Exceptional Winter Park Opportunity with In-Law Suite & Income Potential. THIS HOUSE IS AVAILABLE FOR LEASING OPTION. Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a walking distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park
462 W Lyman Avenue, Winter Park
$1,495,000
3 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Located in the downtown corridor within 2 blocks of Park Avenue, this exceptional one-story residence completed in 2022 offers the ideal blend of contemporary design, refined finishes and a walking lifestyle to downtown WP shops, events & restaurants! Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

462 W Lyman Avenue, Winter Park
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