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Winter Park Homes for Sale

Winter Park, Florida, is a suburban city found in Orange County and part of the Orlando-Kissimmee-Sanford metro area. With a rich historic history, Winter Park was founded as a resort community in the early 20th century. Winter Park has grown and is now known for its vibrant main street, luxury communities, museums, galleries, parks and an incredible chain of lakes popular for skiing, boating, fishing and general recreation.

One of the most popular and renowned areas of the City is Park Avenue, a traditional bricked street which provides an amazing variety of fine and casual dining, boutique shopping, entertainment, a central park and museums. The City is home to a public golf club, historic cemetery, train station, art galleries and a famous boating tour. Additional popular activities include visiting the Winter Park Village mall, Annie Russell Theatre, Rollins College, Charles Hosmer Morse Museum of American Art, Cornell Fine Arts Museum, Hannibal Square, Mead Botanical Gardens, Kraft Azalea Park and the Winter Park Historical Museum. The scenic boat tours also provide a great way to see the beautiful luxury homes and natural beauty found throughout the City. Winter Park is also host to the world-famous Winter Park Sidewalk Art Festival, which is the largest and oldest of the art festivals found in the country today.

Winter Park is part of the Orange County Public School system and also boasts great schools from public elementary schools to well-known colleges. Some of the top-ranked schools in Winter Park include: Aloma Elementary School, The Geneva School, The Parke House Academy, Full Sail University, Lakemont Elementary, St. Margaret Mary Catholic School, Trinity Preparatory, Winter Park High, Rollins College, Valencia Community College and the Crealde School of Art.

Winter Park offers many forms of housing including luxury, waterfront, golf front, single-family homes, townhomes, condos, and villas. However, most are single-family homes and tend to be larger with four or more bedrooms. A significant number of the single-family homes have been custom built and target buyers looking for luxurious amenities. A significant number of large estate homes are waterfront and located on the Winter Park Chain of Lakes. The average home listed on the market in Winter Park is about $856K; however, prices can easily range into the multi-millions for some of the larger estate homes.

Some of the most desirable communities in Central Florida are located in Winter Park including Bear Gully Bay, Bear Gully Pointe, Bengerts Bend, Brookshire Heights, Camwood, Charmont, Comstock Park, Conwill Estates, Dixie Terrace, Dubsdread Heights, Ellno Willo, Forest Hills, Fountainhead, Glencoe, Golfview Terrace, Green Oaks, Green Terrace, J Kronenberger, Kenilworth Shores, Killarney Circle, Lake Howell, Lake Howell Lane, Lake Knowles Terrace, Lake Virginia, Maitland Shores, Osceola Place, Park Grove, Sevilla, Shores Lake Killarney, Sicilian Shores, Sylvan Lake Shores, Sylvan Park, Timberlane Shores, Tuscany Place, Tuscany Terrace, Twelve Oaks, Virginia Heights, Windsong and many more.

Looking to sell your home in Winter Park? Follow this link to get an "Instant" Home Value Report

Newest Winter Park Homes for Sale

567 Osceola Avenue, Winter Park $932,000

Award Winning, Winter Park Historic 4 Bed, 3-1/2 Bath Home meticulously restored to Perfection. With Features and Finishes that rival new homes in the area, it will not ...

4 Beds
3 Baths
Osceola Court SubDv.
32789 Zip Code

2425 Whitehall Circle, Winter Park image

2425 Whitehall Circle, Winter Park $745,000

Elegant Craftsman style home situated on quiet tree-lined street. This wonderful home offers over 3100 SF with 4 BDS - 3.5 BA PLUS BONUS RM. First floor open layout boa...

4 Beds
3 Baths
Brookshire Heights 3rd Add SubDv.
32792 Zip Code

3600 Hawthorne Lane, Winter Park $315,000

This Winter Park one-story home offers granite countertops, and a two-car garage. This home is vacant and cleaned regularly.

3 Beds
2 Baths
Garden Lake Estates Unit 1 SubDv.
32792 Zip Code

2844 Will O Th Green, Winter Park $439,900

Style, comfort, and space come together in this open-concept floor plan. Whether it’s home-schooling, telecommuting, or needing that extra living area for the kids, this...

4 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

672 Osceola Avenue Unit 672, Winter Park image

672 Osceola Avenue Unit 672, Winter Park — B $449,000

Just a few blocks from Park Avenue and Rollins college sits a small cluster of luxury condos on a piece of property that is part of a larger piece on Lake Virginia. You e...

2 Beds
2 Baths
Villa Del Seis Condo SubDv.
32789 Zip Code

1637 Magnolia Avenue, Winter Park $1,489,000

Welcome to the home of your dreams!! Your brand new 2020 Custom built French Provincial style estate is ready and waiting for your family. The quality craftsmanship and p...

4 Beds
4 Baths
Flora Park 2nd Add SubDv.
32789 Zip Code

1228 Mayfield Avenue, Winter Park $1,740,000

This spectacular Spanish Colonial style home is situated on an oversized lot on a quiet brick street in one of Winter Park’s most sought after neighborhoods. Painstaking...

4 Beds
3 Baths
Temple Heights SubDv.
32789 Zip Code

929 Grover Avenue, Winter Park $725,000

STUNNING mid-century modern home that is steps away from MEAD Gardens!!! LOVINGLY updated and restored, the home has GORGEOUS Terrazzo floors throughout! 3 bedroom/3 ba...

3 Beds
3 Baths
Garden Acres SubDv.
32789 Zip Code

331 Cortland Ave, Winter Park $449,000

Welcome Home to this charming single story 2 bedroom 2 bath home located in desirable Winter Park. Built in 1946, this home exudes charm, boasting original bathrooms and...

2 Beds
2 Baths
Osceola Summit SubDv.
32789 Zip Code

2041 Lake Drive, Winter Park $639,000

DESIREABLE LAKE KILLARNEY CLASSIC HOME WITH MODERN UPDATES JUST BEGINS TO DESCRIBE THIS 4 BEDROOM 4 BATH POOL HOME SEATED ON A CORNER LOT IN THE VERY PRIVATE NEIGHBORHOOD...

4 Beds
4 Baths
Lake Killarney Homeowners' Association, Inc. SubDv.
32789 Zip Code

1750 Edwin Boulevard, Winter Park $1,425,000

Discover an exceptional opportunity in the heart of Winter Park. This beautiful custom-built two-story modern home is very bright with southern exposure on the rear of th...

5 Beds
4 Baths
Campo Bello SubDv.
32789 Zip Code

820 N Lakemont Avenue, Winter Park image

820 N Lakemont Avenue, Winter Park $790,000

An exceptional opportunity awaits in the heart of Winter Park. This transitional-style custom home is comprised of four bedrooms and three baths over 3,113 square feet of...

4 Beds
3 Baths
Acreage SubDv.
32792 Zip Code

55 Trismen Terrace, Winter Park $6,595,000

Presenting to the market for the first time in 54 years and the first time ever as three properties combined over the years all within footsteps of Park Avenue and situat...

4 Beds
6 Baths
Osceola Shores Sec 01 SubDv.
32789 Zip Code

1641 Winchester Drive, Winter Park image

1641 Winchester Drive, Winter Park $809,000

Absolutely lovely 3-bedroom, 2.5-bath renovated home in highly desirable Timberlane Shores. Split level floor plan with walk out basement to patio and large private fully...

3 Beds
2 Baths
Timberlane Shores SubDv.
32789 Zip Code

2837 Scarlet Road, Winter Park $379,900

Opportunity knocks - ACT FAST!!! This beautiful fully remodeled 3 bedroom, 2 bath home is not going to last! Wood plank tile flooring throughout with rugs in the bedrooms...

3 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

467 Carolina Avenue, Winter Park $1,195,000

Brand new home. 10 foot ceilings. Front and back porches. Engineered wood floors. Thermidor appliances. Upgraded windows. Huge attic storage. Surrounded by 6 foot block w...

4 Beds
3 Baths
Winter Park SubDv.
32789 Zip Code

1721 Shasta Court, Winter Park $329,900

***GREAT SOLID BLOCK CORNER LOT HOUSE***3 BEDROOMS*** 2 FULL BATHS***FORMAL LIVING ROOM***DINING ROOM***FULL KITCHEN***FAMILY ROOM***INGROUND POOL***FENCED IN YARD***OVER...

3 Beds
2 Baths
Garden Lake Estates Unit 1 SubDv.
32792 Zip Code

7789 Fox Knoll Place, Winter Park $309,000

This charming house is located in heart of Seminole County and located in very quite neighborhood. The neighborhood is zoned in best of Seminole County School District a...

4 Beds
2 Baths
Bridgewater SubDv.
32792 Zip Code

1601 Legion Drive, Winter Park $1,295,000

Presenting an exquisite new listing in the Heart of Winter Park. Completely remodeled in 2019 from floor to ceiling, this casually elegant, single-story residence feature...

3 Beds
2 Baths
Green Oaks Rep 02 SubDv.
32789 Zip Code

1055 Aragon Avenue, Winter Park — 1055 $385,000 ▼

Welcome to your hidden oasis in the heart of highly desirable Winter Park! This updated townhome is located on one of Winter Park's famous brick street just minutes from ...

3 Beds
2 Baths
Villas Aragon Condo SubDv.
32789 Zip Code

3681 Midiron Drive, Winter Park $432,900

Don't miss your chance to own this spacious 4 bedroom 3 bath beautifully remodeled home located on the 4th fairway of the historic Dubstread Golf Course! This move-in rea...

4 Beds
3 Baths
Golfview SubDv.
32789 Zip Code

1965 Poinciana Road, Winter Park $389,000

Renovated home in Winter Park in Winter Woods backs up to a wooded backdrop with no neighbors in the back providing tremendous privacy. This 3-bedroom, 2-bath split plan ...

3 Beds
2 Baths
Winter Woods Unit 02 SubDv.
32792 Zip Code

1136 Oaks Boulevard, Winter Park $695,000

Remodel existing home or it is a perfect location to build your custom home on this oversized lot off Park Avenue in Winter Park. The property measures 15,836 square feet...

3 Beds
2 Baths
Dixie Terrace SubDv.
32789 Zip Code

1230 Wading Waters Circle, Winter Park image

1230 Wading Waters Circle, Winter Park — Meritage Homes $808,849 ▲

Brand NEW energy-efficient home ready NOW! This Wimberley II home sits on a pond lot and features a gourmet kitchen, dual owner's suite, game room, and more! Located alon...

6 Beds
5 Baths
Hawks Crest SubDv.
32792 Zip Code

100 W Reading Way, Winter Park $675,000

This is a wonderful opportunity to purchase in one of the most sought after neighborhoods in Winter Park. Beautiful oak tree lined brick streets make this one of the pret...

Forrest Hills SubDv.
32789 Zip Code

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