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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

1751 Goodrich Avenue, Winter Park image
1751 Goodrich Avenue, Winter Park $859,900

This almost-new light and bright home with top of the line finishes was fully renovated in 2019. 2,172 sq ft under air, 4 Beds, 3.5 bathrooms and 2 car garage, this home ...

  • 4 Beds
  • 3.5 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
2216 Fairglenn Way, Winter Park image
2216 Fairglenn Way, Winter Park $379,900

Beautiful 4-bedroom 2-bathroom pool home in Quail Run SUBD. As you walk in the door you will be greeted by an amazing open concept floor plan tile and wood floor through...

  • 4 Beds
  • 2 Baths
  • Quail Run SubDv.
  • 32792 Zip Code
340 Alberta Drive, Winter Park image
340 Alberta Drive, Winter Park $899,000

*PRICED 100K BELOW APPRAISIAL!* Feast your eyes on this gorgeously renovated 4 bedroom 4 bathroom home nested in beautiful Winter Park. All four bedrooms of the home are ...

  • 4 Beds
  • 4 Baths
  • Osceola Summit SubDv.
  • 32789 Zip Code
2251 Coventry Drive, Winter Park image
2251 Coventry Drive, Winter Park $349,000

Nestled in the heart of Winter Park, this modernized home presents with five bedrooms, three bathrooms and flexible floor plan for the entire family to enjoy. Step inside...

  • 5 Beds
  • 3 Baths
  • Winter Woods SubDv.
  • 32792 Zip Code
2779 Prince John Road Unit 1, Winter Park image
2779 Prince John Road Unit 1, Winter Park $384,900

One story charmer located on a quiet street in Winter Park Pines. This 3 bedroom 2 bathroom home features 1,579 square feet of living space with beautiful tile floors thr...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines Rep SubDv.
  • 32792 Zip Code
1919 Stonehurst Road, Winter Park image
1919 Stonehurst Road, Winter Park $2,000,000

Beautifully custom built single story home offers 5 bedrooms, 4 and a half baths, two car attached garage, a two car detached garage/studio, and an amazing outdoor living...

  • 5 Beds
  • 4.5 Baths
  • Stonehurst Estates SubDv.
  • 32789 Zip Code
2726 Lake Howell Lane, Winter Park image
2726 Lake Howell Lane, Winter Park $1,450,000

Vacant Land Easy to Show! Located on the shores of Lake Howell, this Lakefront property offers the potential buyer over 4 acres of High and Dry Land in a serene natural s...

  • 32792 Zip Code
251 Glenridge Way, Winter Park image
251 Glenridge Way, Winter Park $425,000

This spacious yet quaint bungalow sits on a large lot in beautiful Winter Park Charmont area. The home is perfect as is but the lot is large and complete plans to build ...

  • 3 Beds
  • 3 Baths
  • Charmont SubDv.
  • 32789 Zip Code
436 Darcey Drive, Winter Park image
436 Darcey Drive, Winter Park $389,000

Newly remodeled Kitchen, CHECK! New stainless steel appliances, CHECK! Granite counter tops, CHECK! Sparkling Pool, CHECK! Amazing indoor Laundry/Mudroom, CHECK! New Pain...

  • 3 Beds
  • 2 Baths
  • Brookshire Heights SubDv.
  • 32792 Zip Code
1210 Oaks Blvd, Winter Park image
1210 Oaks Blvd, Winter Park $1,225,000

New home located just a block from Park Ave! Drive up to this beauty and fall in love. This 3 bedroom, 3.5 bath home boasts open spaces and clean lines inside and out. H...

  • 3 Beds
  • 3.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
530 N Lakemont Avenue, Winter Park image
530 N Lakemont Avenue, Winter Park $368,000

You can't beat this location! This recently renovated fenced-in 3 bed/ 2 bath Winter Park home offers the convenience you have been waiting for. Major updates in 2019 inc...

  • 3 Beds
  • 2 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
2443 Forfarshire Drive, Winter Park image
2443 Forfarshire Drive, Winter Park $399,000

Gorgeous 3 bedroom, 2 bath pool home, located on a quiet low traffic street. Home features a split bedroom plan, vaulted ceilings in the family room, built in book shelv...

  • 3 Beds
  • 2 Baths
  • Brookshire Heights 2nd Add SubDv.
  • 32792 Zip Code
1791 Magnolia Avenue, Winter Park image
1791 Magnolia Avenue, Winter Park $379,000

Incredible Opportunity to Build your Custom Home in this distinguished location of the sought after "Tree Streets' of Winter Park 32789 zip! The alluring location is clo...

  • Flora Park 2nd Add SubDv.
  • 32789 Zip Code
2271 Nairn Drive, Winter Park image
2271 Nairn Drive, Winter Park $409,900

LOCATION, LOCATION, LOCATION! Live in, renovate, rent out or build new! This 17,241 square foot lot is over-sized for the area. Home needs some updating as seller was in ...

  • 3 Beds
  • 2 Baths
  • Aloma Section 1 SubDv.
  • 32792 Zip Code
1757 Pine Avenue, Winter Park image
1757 Pine Avenue, Winter Park $479,900

Fantastic Updated Mid-Century Home Located In One of Central Florida's Most Sought after Areas. Situated on almost 1/4 Acre Lot, this home was Lovingly Renovated in 2014...

  • 3 Beds
  • 2 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
2906 Banchory Road, Winter Park image
2906 Banchory Road, Winter Park $434,900

Beautiful updated Winter Park home. This four bedroom two bathroom pool home has been almost completely renovated. The kitchen features granite counters, an island, bui...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
345 W Welbourne Avenue Unit 104, Winter Park image
345 W Welbourne Avenue Unit 104, Winter Park — Douglas Grand $799,000 ▲

Enjoy the pleasure of living an urban, care-free lifestyle in beautiful downtown Winter Park – just one block away from chic Park Avenue with all its lovely boutique sho...

  • 3 Beds
  • 3.5 Baths
  • Winter Park Residential SubDv.
  • 32789 Zip Code
1476 Grove Terrace, Winter Park image
1476 Grove Terrace, Winter Park $1,895,000

Stunning Mediterranean Estate in the Heart of Winter Park. Custom built and crafted in 2008 this home leaves no detail left out and is exquisite throughout. Offering an ...

  • 5 Beds
  • 5.5 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
2685 Bongart Road, Winter Park image
2685 Bongart Road, Winter Park $314,995

* THE BEST VALUE IN THE NEIGHBORHOOD * WHAT A GREAT OPPORTUNITY THIS RANCH HOME PRESENTS. 3 BEDROOMS / 2 BATH HOME IN SOUGHT-AFTER WINTER PARK NEIGHBORHOOD. THIS HOUSE HA...

  • 3 Beds
  • 2 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
2423 Brookshire Avenue, Winter Park image
2423 Brookshire Avenue, Winter Park $525,000

Completely renovated mid-century ranch home located in Brookshire Heights in the heart of Winter Park; walking distance to Brookshire Elementary, a biking trail, Cady Way...

  • 4 Beds
  • 2 Baths
  • Brookshire Heights 1st Add SubDv.
  • 32792 Zip Code
1852 Barker Drive, Winter Park image
1852 Barker Drive, Winter Park $369,000 ▼

Excellent Winter Park location within easy walking distance to Baldwin Park restaurants, shopping, and large parks. This 4 bedroom 2 bathroom single story home with 2074 ...

  • 4 Beds
  • 2 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
1937 Kimbrace Place, Winter Park image
1937 Kimbrace Place, Winter Park $515,000

Quarantined? See virtual tour! One of a kind, immaculate pool home in the glorious City of Winter Park. Magnificent kitchen awaits the home chef: stepped shaker wood cabi...

  • 3 Beds
  • 2.5 Baths
  • Kenilworth Shores Sec 01 SubDv.
  • 32792 Zip Code
2077 Poinciana Road, Winter Park image
2077 Poinciana Road, Winter Park $384,999

Want to live in Winter Park? Come see this updated midcentury ranch home with an open floor plan. Walk into the foyer and see the living room, dining, kitchen combo. T...

  • 3 Beds
  • 2 Baths
  • Winter Woods Unit 04 SubDv.
  • 32792 Zip Code
1550 Palmer Avenue, Winter Park image
1550 Palmer Avenue, Winter Park $385,000

Charming 3 bedroom 3 bathroom Winter Park Bungalow. Home features an in-law suite with large bathroom and walk in closet. Dining room, master bedroom and 2nd bedroom has ...

  • 3 Beds
  • 3 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
2170 Blossom Lane, Winter Park image
2170 Blossom Lane, Winter Park $425,000

Lovely, Winter Park, single-access Lake Kilarney neighborhood. Largest lot on the street at .62 acres!! Charming three-bedroom home on a quiet street, light and airy rema...

  • 3 Beds
  • 2 Baths
  • N/A SubDv.
  • 32789 Zip Code

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