Winter Park Real Estate

Winter Park is a charming subdivision nestled in the heart of Orange County, Florida. Known for its picturesque tree-lined streets, historic architecture, and vibrant community, Winter Park offers a unique blend of small-town charm and modern amenities. This sought-after neighborhood is perfect for those looking to enjoy a high quality of life in a beautiful setting.

Residents of Winter Park have access to top-rated schools, upscale shopping and dining options, and a variety of cultural attractions, including the Charles Hosmer Morse Museum of American Art and the Albin Polasek Museum & Sculpture Gardens. The area also boasts numerous parks, lakes, and green spaces, providing plenty of opportunities for outdoor recreation.

With its convenient location just a short drive from downtown Orlando, Winter Park offers the perfect balance of tranquility and urban convenience. Whether you're strolling along Park Avenue, exploring the scenic Mead Botanical Garden, or enjoying a boat ride on Lake Virginia, Winter Park truly has something for everyone. Come discover the beauty and charm of Winter Park living!

Newest Listings in Winter Park

540 N Pennsylvania Avenue, Winter Park image

540 N Pennsylvania Avenue, Winter Park $3,950,000

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 R...

4 Beds
2 Baths
Winter Park SubDv.
32789 Zip Code

471 Holt Avenue, Winter Park $975,000 ▼

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirabl...

4 Beds
3 Baths
Winter Park SubDv.
32789 Zip Code

540 N Pennsylvania Avenue, Winter Park $3,950,000 ▼

MAJOR PRICE IMPROVEMENT—NOW OFFERED BELOW $4 MILLION! Rare Winter Park redevelopment opportunity on a nearly half-acre corner parcel just minutes from Park Avenue. Newly ...

Winter Park SubDv.
32789 Zip Code

669 W Comstock Avenue, Winter Park image

669 W Comstock Avenue, Winter Park $210,000 ▼

A rare piece of land in the heart of Winter Park. Short distance to Park Ave. Approved permits for 2000 sqft under AC housing project.

Winter Park SubDv.
32789 Zip Code

462 W Lyman Avenue, Winter Park $1,495,000 ▼

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, ref...

3 Beds
3 Baths
Winter Park SubDv.
32789 Zip Code

541 W Canton Avenue, Winter Park $2,495,000 ▼

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 Orl...

4 Beds
4 Baths
Winter Park SubDv.
32789 Zip Code

503 N Interlachen Avenue, Winter Park image

503 N Interlachen Avenue, Winter Park $4,500,000 ▼

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...