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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

215 Blossom Lane, Winter Park image
215 Blossom Lane, Winter Park $450,000

Renovated in 2018 and move-in ready. In a great Winter Park location with deeded access to Lake Killarney. Situated on a large 0.35 acre lot in a quiet neighborhood with ...

  • 3 Beds
  • 2 Baths
  • Shores Lake Killarney SubDv.
  • 32789 Zip Code
5541 Howell Branch Road, Winter Park image
5541 Howell Branch Road, Winter Park $899,000

2 parcels located at Dodd Rd. and Howell Branch Rd. in Winter Park, Fl. Over 1 acre of redevelopment land with a future land use of OFFICE! Great location, high daily tra...

  • 32792 Zip Code
1607 Miller Avenue, Winter Park image
1607 Miller Avenue, Winter Park $389,000

Duplex For sale with second 2/1 structure less than 1000 sq. ft. , needs complete renovation , all units on month to month rent , property being sold in "as is" condit...

  • 6 Beds
  • 3 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
1814 Walker Avenue, Winter Park image
1814 Walker Avenue, Winter Park $494,000

Beautifully remodeled property in the heart of Winter Park. This home features several upgrades that include fresh Interior and exterior paint, custom wood cabinets, quar...

  • 3 Beds
  • 2.5 Baths
  • Osceola Heights SubDv.
  • 32789 Zip Code
2172 Marsh Sedge Lane, Winter Park image
2172 Marsh Sedge Lane, Winter Park $425,640

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January-February 2020! The Valencia features an open floorplan providing flexibility and i...

  • 4 Beds
  • 2 Baths
  • Hawk's Crest SubDv.
  • 32792 Zip Code
Winter Park image
Winter Park $485,148

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January-February 2020! Use this Florentine's first-floor flex room as a formal living or d...

  • 4 Beds
  • 2.5 Baths
  • 32792 Zip Code
1080 Wading Waters Circle, Winter Park image
1080 Wading Waters Circle, Winter Park $612,665

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January-February 2020! The one-story Shore home features a split floorplan. Gourmet kitche...

  • 4 Beds
  • 3 Baths
  • Hawk's Crest SubDv.
  • 32792 Zip Code
2214 Marsh Sedge Lane, Winter Park image
2214 Marsh Sedge Lane, Winter Park $553,613

Under Construction. "Under Construction". Brand NEW energy-efficient home ready February 2020! Relax and unwind in the Chislett's private master suite featuring tray ceil...

  • 5 Beds
  • 4 Baths
  • Hawk's Crest SubDv.
  • 32792 Zip Code
1177 Wading Waters Circle, Winter Park image
1177 Wading Waters Circle, Winter Park $627,914

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January-February 2020! The Palermo II is a one-story home featuring tile roofing, 3 car ga...

  • 4 Beds
  • 3 Baths
  • Hawk's Crest SubDv.
  • 32792 Zip Code
751 Pansy Avenue, Winter Park image
751 Pansy Avenue, Winter Park $425,000

Winter Park - Off Park Avenue in million dollar neighborhood!! Spacious 3 bdrm 2 bath bungalow on brick street with custom lamp posts. Home features living, dining & fa...

  • 3 Beds
  • 2 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
7839 University Garden Drive, Winter Park image
7839 University Garden Drive, Winter Park $450,000

GREAT OPPORTUNITY! MOBILE HOME AND SEPERATE BLOCK HOME ON 4.93 LEVEL ACRES. LAND IS PERFECT FOR BUILDING DREAM HOME OR POSSIBLE MULTI FAMILY HOMES.CLOSE TO UCF, SHOPPING,...

  • 3 Beds
  • 2.5 Baths
  • Lost Lake Village SubDv.
  • 32792 Zip Code
1721 Westchester Avenue, Winter Park image
1721 Westchester Avenue, Winter Park $799,000

This stunning Winter Park home, situated in the desirable Orwin Manor neighborhood, combines style and elegance with the most convenient location in all of Central Florid...

  • 4 Beds
  • 3 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
1470 Glencoe Road, Winter Park image
1470 Glencoe Road, Winter Park $935,000

In the heart of Olde Winter Park, this 1920s home with historical designation, boasts modern finishes and updates keeping true to the original charm. Located in the highl...

  • 5 Beds
  • 3.5 Baths
  • Virginia Heights SubDv.
  • 32789 Zip Code
1772 Pine Avenue, Winter Park image
1772 Pine Avenue, Winter Park $450,000

Builder's dream lot! This very large lot, 77x151.42, is located on one of the very desirable "tree streets" of Winter Park. Extremely convenient location, walking dista...

  • 2 Beds
  • 1 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
1941 Legion Drive, Winter Park image
1941 Legion Drive, Winter Park $4,699,000

Stately custom Winter Park estate on Lake Maitland spans over 10,000 sq ft, offers 6-bed,7-baths,2-half for gracious living and refined comfortable entertaining.Two-story...

  • 7 Beds
  • 8.5 Baths
  • Green Oaks Rep 02 SubDv.
  • 32789 Zip Code
440 Clarendon Avenue, Winter Park image
440 Clarendon Avenue, Winter Park $869,000

Modernized gourmet kitchen with eat in area, featuring French doors opening to a private enclosed large outdoor brick paved yard, perfect for year round Florida en...

  • 4 Beds
  • 3.5 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
2340 Lafayette Avenue, Winter Park image
2340 Lafayette Avenue, Winter Park $1,375,000

Under Construction. Unique ONE-STORY build on oversized lot. Brand new construction offered by Rex-Tibbs Construction, one of Winter Park's premier custom home builders f...

  • 4 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
5632 Pats Point, Winter Park image
5632 Pats Point, Winter Park $360,000

Stunning Spacious 5 Bedroom 3.5 Bath POOL HOME with 1ST FLOOR MASTER now available with a Winter Park address. This Beautiful 2 Story is ready for your extended family an...

  • 5 Beds
  • 3.5 Baths
  • Bear Gully Forest SubDv.
  • 32792 Zip Code
1051 Aloma Avenue, Winter Park image
1051 Aloma Avenue, Winter Park $720,000

This beautiful Spanish Casita style home is located in highly desirable Winter Park. It is a short distance to Park Avenue, Hannibal Square, and Winter Park Village. Ente...

  • 3 Beds
  • 4 Baths
  • Osceola Summit SubDv.
  • 32789 Zip Code
1881 Windsor Drive, Winter Park image
1881 Windsor Drive, Winter Park $435,000

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

  • 4 Beds
  • 3 Baths
  • V H Musselwhites Sub SubDv.
  • 32789 Zip Code
1861 Windsor Drive, Winter Park image
1861 Windsor Drive, Winter Park $450,000

INVESTOR ALERT! Great tenants in place and occupied until 5/15/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

  • 4 Beds
  • 3 Baths
  • V H Musselwhites Sub SubDv.
  • 32789 Zip Code
261 Spring Lane, Winter Park image
261 Spring Lane, Winter Park $829,000

This beautiful 7 bedroom pool home features a traditional layout with formal living and dining rooms, an open kitchen and family room, and downstairs guest bedroom. From ...

  • 7 Beds
  • 5 Baths
  • The Ripples Add SubDv.
  • 32789 Zip Code
2141 Winter Park Road, Winter Park image
2141 Winter Park Road, Winter Park $435,000

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

  • 4 Beds
  • 3 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1791 Goodrich Avenue, Winter Park image
1791 Goodrich Avenue, Winter Park $445,000

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

  • 4 Beds
  • 3 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
3232 Young Street, Winter Park image
3232 Young Street, Winter Park $345,000

This beautiful 3 bedroom home, features a comfortable floor plan, and a fenced backyard with a large salt water pool great for family activities and entertaining guest. C...

  • 3 Beds
  • 2 Baths
  • Winter Park Forest SubDv.
  • 32792 Zip Code

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