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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

1701 Magnolia Avenue, Winter Park image
1701 Magnolia Avenue, Winter Park $474,900

This lot currently has a home on it but the ideal location is a builders dream. Can be bought with MLS O5762494 and you would have THREE LOTS in the heart of winter park!...

  • Flora Park 2nd Add SubDv.
  • 32789 Zip Code
1685 Magnolia Avenue, Winter Park image
1685 Magnolia Avenue, Winter Park $799,900

Double lot in sought after Winter Park! Please note that this lot is in the process of being expanded and public record may not reflect accurately at this time. You can b...

  • Flora Park 2nd Add SubDv.
  • 32789 Zip Code
633 Balmoral Road, Winter Park image
633 Balmoral Road, Winter Park $995,000

Wonderful opportunity to build new or renovate existing home on Beautiful Lake Berry! With a Southern Exposure your views of the Sunrise and Sunset are Spectacular! The ...

  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
633 Balmoral Road, Winter Park image
633 Balmoral Road, Winter Park $995,000

Wonderful opportunity to build new on this Half Acre Lot, or renovate existing home on Beautiful Lake Berry! With a Southern Exposure your views of the Sunrise and Sunse...

  • 4 Beds
  • 2.5 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1441 Cardinal Court, Winter Park image
1441 Cardinal Court, Winter Park $639,900

Very desirable Old Winter Park. Situated at the end of a quiet, tree-lined cul-de-sac. This custom home has an open, split floorplan includes a formal dining room, living...

  • 3 Beds
  • 2 Baths
  • Winflor Court Pt Rep SubDv.
  • 32789 Zip Code
1552 Holts Grove Circle, Winter Park image
1552 Holts Grove Circle, Winter Park $1,550,000

Designer Showcase Home custom built by Hal George/Parkland Homes. Completely re-modeled white-washed brick stunner- 4790 sq ft.- 5 Bedroom/7 bath Located on quiet cul-de-...

  • 5 Beds
  • 6.5 Baths
  • Windsong Lakeside Sec 02 43/71 SubDv.
  • 32789 Zip Code
626 S Lakemont Avenue, Winter Park image
626 S Lakemont Avenue, Winter Park $378,000

BEAUTIFUL. Functional OPEN FLOOR PLAN gem in desirable Kenilworth Shores. CIRCULAR DRIVEWAY for additional parking space. FRONT PORCH takes you inside to FOYER. LIVING AR...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 4 SubDv.
  • 32792 Zip Code
1352 Palm Avenue, Winter Park image
1352 Palm Avenue, Winter Park $1,107,750

Come see this Beautiful Transitional Style, Custom Built Home in the heart of Winter Park. With 4 Bedrooms and 4.5 Baths there is plenty of room for everyone! The Kitchen...

  • 4 Beds
  • 4.5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
451 W Comstock Avenue, Winter Park image
451 W Comstock Avenue, Winter Park $1,299,000

One or more photo(s) has been virtually staged. Amazing 4 bedroom / 4.5 bathroom modern masterpiece with soaring 12-foot custom coffered & lighted ceilings, walking dista...

  • 4 Beds
  • 4.5 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
1724 Harvest Cove, Winter Park image
1724 Harvest Cove, Winter Park $320,000

This beautiful house is totally renovated and located in Seminole County school district. If you are looking for completely finished house and great location, this house ...

  • 3 Beds
  • 2.5 Baths
  • Autumn Glen SubDv.
  • 32792 Zip Code
2025 Kimbrace Place, Winter Park image
2025 Kimbrace Place, Winter Park $324,000

Lifestyle & Charm in Winter Park! Come see this immaculately maintained Ranch style 3 Bedroom/2 Bath,1390 sf home on a large CORNER LOT! The interior has a warm & cozy ...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 03 SubDv.
  • 32792 Zip Code
1001 N Kentucky Avenue, Winter Park image
1001 N Kentucky Avenue, Winter Park $1,200,000

NEW CONSTRUCTION, MODERN HOME CLOSE TO PARK AVE. WINTER PARK! This home has plenty to offer. Fantastic lighting throughout by thoughtful use of large windows and oversi...

  • 4 Beds
  • 3.5 Baths
  • Fairbanks Park SubDv.
  • 32789 Zip Code
1939 Gunn Road, Winter Park image
1939 Gunn Road, Winter Park $369,900

Kenilworth Shores SHOW STOPPER!!!! This Immaculate and remodeled 3 bedroom 2 bathroom is a must see~ offering countless upgrades from the designer kitchen, wood flooring,...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
1771 Taylor Avenue, Winter Park image
1771 Taylor Avenue, Winter Park $1,389,000

Under Construction. The latest masterpiece from Winter Park’s premier builder FG Schaub Custom Homes. This Modern Farmhouse was designed by David Larson and is sure to ex...

  • 5 Beds
  • 5.5 Baths
  • Orange Grove Sub SubDv.
  • 32789 Zip Code
1845 Harland Park Drive, Winter Park image
1845 Harland Park Drive, Winter Park $1,395,000

Simply stunning! This like new Mediterranean Estate Home is located in the highly sought after Windsong Community and has been tastefully upgraded and meticulously mainta...

  • 4 Beds
  • 4.5 Baths
  • Windsong-Knowles Place SubDv.
  • 32789 Zip Code
147 S Interlachen Avenue Unit 202, Winter Park image
147 S Interlachen Avenue Unit 202, Winter Park — 147 $1,339,000

Enjoy the comforts of downtown Winter Park living in this spacious, luxurious condo with 3 bedrooms and 4 1/2 baths. This sophisticated Mediterranean style gem features a...

  • 3 Beds
  • 4.5 Baths
  • 147 Interlachen Place SubDv.
  • 32789 Zip Code
1000 Anchorage Court, Winter Park image
1000 Anchorage Court, Winter Park $2,275,000

This luxurious estate is a European masterpiece located in the golden triangle of Winter Park. A mature, well manicured podocarpus hedge surrounds this .59 acre property ...

  • 6 Beds
  • 5.5 Baths
  • Anchorage Estates SubDv.
  • 32789 Zip Code
1315 Sunset Drive, Winter Park image
1315 Sunset Drive, Winter Park $949,000

When pride of ownership meets your opportunity to own a beautiful traditional home in Winter Park. Updated with quality and attention to detail, this 3 bedroom 3/1 bath i...

  • 3 Beds
  • 3.5 Baths
  • Lake Knowles Terr SubDv.
  • 32789 Zip Code
2031 Venetian Way, Winter Park image
2031 Venetian Way, Winter Park $1,895,000

Tremendous character and charm throughout this stunning Santa Barbara-style Mediterranean resting on almost a 1-acre lot in the Vias. Waterfront estate size property on t...

  • 5 Beds
  • 3.5 Baths
  • Maitland Shores SubDv.
  • 32789 Zip Code
331 E Reading Way, Winter Park image
331 E Reading Way, Winter Park $915,000

Located on one of Winter Park’s charming brick-lined streets, overlooking a wonderful open green space, this lovely Mediterranean home is one to see! This home is light &...

  • 4 Beds
  • 4.5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1365 Grove Terrace, Winter Park image
1365 Grove Terrace, Winter Park $947,000

amazing double corner lot on a quiet tree lined street surrounded by lakes Mizell and Sylvan. Build your dream home, remodel the existing single level home or move into t...

  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
420 Melrose Avenue, Winter Park image
420 Melrose Avenue, Winter Park $675,000

Situated on an oversized beautiful corner lot in the heart of Olde Winter Park, this 1920s home with historical designation, boasts character and charm. Located in the hi...

  • 4 Beds
  • 2 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
2417 Summerfield Road, Winter Park image
2417 Summerfield Road, Winter Park $399,900

Large renovated and remodeled 4 bedroom Winter Park pool home. This updated and expanded home is sitting on ¼-acre lot in the heart of one of Central Florida’s top rated...

  • 5 Beds
  • 2.5 Baths
  • Williamsburg SubDv.
  • 32792 Zip Code
2418 Euston Road, Winter Park image
2418 Euston Road, Winter Park $379,900

Great location in Winter Park 32789 on an oversized 0.27-acre lot steps from beautiful Lake Killarney! Charm radiates throughout this inviting three-bedroom, two & a half...

  • 3 Beds
  • 2.5 Baths
  • Glencoe Sub SubDv.
  • 32789 Zip Code
935 Greentree Drive, Winter Park image
935 Greentree Drive, Winter Park $4,300,000

Exquisite inside and out! This magnificent Georgian-style estate home was meticulously constructed by Posada Custom Homes and is located in one of Winter Park's most desi...

  • 3 Beds
  • 3.5 Baths
  • Palmer Ave Lakeside Properties Add SubDv.
  • 32789 Zip Code

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