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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

920 S Kentucky Avenue, Winter Park image
920 S Kentucky Avenue, Winter Park $750,000

This 2014 custom built home is for the lifestyle enthusiast. A perfect location combined with highly desired custom features will thrill the most discerning buyers. Shops...

  • 4 Beds
  • 3.5 Baths
  • Fairbanks Park SubDv.
  • 32789 Zip Code
1410 Mayfield Avenue, Winter Park image
1410 Mayfield Avenue, Winter Park $825,000

Welcome to the fabulous one story home in the heart of Winter Park! As you walk in the front door you will love how light and bright the home is, which is accented by the...

  • 4 Beds
  • 3 Baths
  • Temple Heights SubDv.
  • 32789 Zip Code
1244 Valley Creek Run, Winter Park image
1244 Valley Creek Run, Winter Park $339,500

Welcome home to this 3 bedroom, 2 bath pool home located in Winter Park’s established Lost Creek neighborhood. With gorgeous hardwood flooring, extensive ceramic tile, a ...

  • 3 Beds
  • 2 Baths
  • Lost Creek SubDv.
  • 32792 Zip Code
700 Dixie Parkway, Winter Park image
700 Dixie Parkway, Winter Park $650,000

Welcome to this charming pool home in a fabulous location and situated on a wonderful .25 acre lot. Lovely wood floors throughout the formal rooms and all 4 bedrooms. G...

  • 4 Beds
  • 3 Baths
  • Winflor Court Pt Rep SubDv.
  • 32789 Zip Code
2232 Fosgate Drive, Winter Park image
2232 Fosgate Drive, Winter Park $629,000

Beautiful 3 Bedroom, 2 Bathroom POOL home in Winter Park, just outside of Baldwin Park. Located on a huge 1/3 acre fenced lot. Home has new HVAC, new paint inside & out, ...

  • 3 Beds
  • 2 Baths
  • Timberlane SubDv.
  • 32789 Zip Code
440 W Swoope Avenue, Winter Park image
440 W Swoope Avenue, Winter Park — Swoope Park $475,000

One or more photo(s) has been virtually staged. PREMIUM LOCATION! This 2014 built contemporary townhome is welcoming and bright and a great find for an EXECUTIVE LIFESTYL...

  • 4 Beds
  • 3.5 Baths
  • Swoope Park SubDv.
  • 32789 Zip Code
436 Darcey Drive, Winter Park image
436 Darcey Drive, Winter Park $395,000

Beautifully renovated 3 bedroom, 2 bath pool home in Brookshire Heights! This home offers quality construction, new paint, high quality wood grain laminate flooring, an e...

  • 3 Beds
  • 2 Baths
  • Brookshire Heights SubDv.
  • 32792 Zip Code
2061 Temple Drive, Winter Park image
2061 Temple Drive, Winter Park $495,000

This mid-century modern two-bedroom and two-bathroom home could use someone with the love for renovation. You could alternatively utilize the 86’ x 116’ lot to build to s...

  • 2 Beds
  • 2 Baths
  • Tuscania SubDv.
  • 32789 Zip Code
2091 Temple Drive, Winter Park image
2091 Temple Drive, Winter Park $879,000

Remodeled designer home with great character and bright open floor plan. Master suite and 2 additional bedrooms on first level. This European style home is located on won...

  • 4 Beds
  • 3 Baths
  • Tuscania SubDv.
  • 32789 Zip Code
560 Country Club Drive, Winter Park image
560 Country Club Drive, Winter Park $1,945,000

Exceptionally stunning, brand new construction on Winter Park’s Lake Killarney. Built by Lazarus Development this modern, Spanish-inspired home features an amazing floorp...

  • 6 Beds
  • 5.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
161 Alexander Place, Winter Park image
161 Alexander Place, Winter Park $1,794,000

A timeless property in Winter Park, designed by nationally renowned architect Gamble Rogers on a street rich in history & steps away from Lake Osceola. Privacy abounds wh...

  • 5 Beds
  • 5 Baths
  • Alexander Place SubDv.
  • 32789 Zip Code
1220 Verdant Glade Place, Winter Park image
1220 Verdant Glade Place, Winter Park $450,756

Live your Florida dream in the flexible, open-concept Santa Rosa floor plan. Adapt this new Orlando home to your lifestyle and needs. Then enjoy the possibilities. Enter...

  • 4 Beds
  • 3.5 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
1231 Verdant Glade Place, Winter Park image
1231 Verdant Glade Place, Winter Park $472,730

The spacious Anastasia floor plan offers a unique layout that’s ideal for family living. The foyer of the new home in Orlando angles off the front porch, with access to t...

  • 4 Beds
  • 3.5 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
1091 N Pennsylvania Avenue, Winter Park image
1091 N Pennsylvania Avenue, Winter Park $1,295,000

Located on a corner lot in the elegant community of Penn Place, this fabulous home sits just blocks from the Winter Park 9-hole golf course, Park Avenue, and the WP Villa...

  • 4 Beds
  • 3 Baths
  • Pennsylvania Place Rep SubDv.
  • 32789 Zip Code
554 Fitzwalter Drive, Winter Park image
554 Fitzwalter Drive, Winter Park $579,990

Welcome Home! This "one of a kind" meticulously well maintained Winter Park Home is located on one of the most desirable tree lined streets in the Brookshire Heights Neig...

  • 6 Beds
  • 3 Baths
  • Brookshire Heights 1st Add SubDv.
  • 32792 Zip Code
857 Brock Street, Winter Park image
857 Brock Street, Winter Park $675,000

Great opportunity to live in Park Grove and renovate this nice home. Lovely lot and curb appeal. Best schools, walking distance to Park Ave. Easy access to Maitland a...

  • 4 Beds
  • 2.5 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
1335 Chapman Circle, Winter Park image
1335 Chapman Circle, Winter Park $1,195,000

Gorgeous two-story Mediterranean pool home located in Winter Park’s prestigious Windsong community. Special highlights include multiple indoor and outdoor entertaining sp...

  • 4 Beds
  • 3.5 Baths
  • Windsong Elizabeths Walk SubDv.
  • 32789 Zip Code
2316 Poinciana Road, Winter Park image
2316 Poinciana Road, Winter Park $325,000

Beautiful Winter Park Pool Home! This updated pool home is located on a tree-lined street of the desirable Winter Woods Community. Your new home features a large, fully r...

  • 3 Beds
  • 2 Baths
  • Winter Woods Unit 04 SubDv.
  • 32792 Zip Code
517 Country Club Drive, Winter Park image
517 Country Club Drive, Winter Park $969,900

STUNNING MODERN FARMHOUSE! Prepare to be amazed by this BRAND NEW construction by Classic Homes. Tucked away in the private community of Lake Killarney Shores, this lovel...

  • 4 Beds
  • 3.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
531 Country Club Drive, Winter Park image
531 Country Club Drive, Winter Park $969,900

Absolutely stunning, brand new, custom built 4 bed, 3.5 bath pool home, presented by Lazarus Development Group. This home features so much attention to detail, including ...

  • 4 Beds
  • 3.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
1691 Chestnut Avenue, Winter Park image
1691 Chestnut Avenue, Winter Park $550,000

Significant opportunity to own one of the largest lots in the highly desirable tree lined streets of Winter Park. Land value is $550,000. – at lot size of 18,418 square f...

  • 3 Beds
  • 1.5 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
2843 Sheriff Way Unit 5, Winter Park image
2843 Sheriff Way Unit 5, Winter Park $399,900

Does your New Home checklist include a Prime Location, Top Rated School Districts, Outdoor Fitness along the Cady Way Trail, Local Golf Course, Boutique Shopping, Local D...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
1747 Sarong Place, Winter Park image
1747 Sarong Place, Winter Park $584,999

Welcome to this lovely Winter Park pool home with a 3-car garage. This home boasts a grand foyer with a soaring 23' ceiling. When you enter the home you will see a form...

  • 5 Beds
  • 4.5 Baths
  • Annebury SubDv.
  • 32792 Zip Code
1561 Dodd Road, Winter Park image
1561 Dodd Road, Winter Park $1,300,000

8.8 Acres Residential Land Winter Park $1,300,000; 1561 Dodd Rd, Winter Park, FL 32792 - Park-like infill site in east Winter Park. Future land use is low density r...

  • 32792 Zip Code
2301 Forrest Road, Winter Park image
2301 Forrest Road, Winter Park $1,299,000

This fabulous transitional 5 bedroom home is situated on a quiet brick street just minutes to Park Avenue’s shopping & restaurants or downtown Orlando’s business district...

  • 5 Beds
  • 4.5 Baths
  • The Ripples SubDv.
  • 32789 Zip Code

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