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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

1150 Via Salerno, Winter Park image
1150 Via Salerno, Winter Park $739,000

Prime Winter Park lot situated in the prestigious Winter Park Via's. Nestled in the landscape of the oak tree lined brick street. Short walk to Kraft Azalea Gardens and L...

  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
240 N Phelps Ave, Winter Park image
240 N Phelps Ave, Winter Park $499,000

This is a great opportunity to build your dream home on in the heart of Winter Park surrounded by multi million-dollar homes. This beautiful lot measures 62x144 (8928 tot...

  • Sylvan Heights SubDv.
  • 32789 Zip Code
3003 Ash Park Point, Winter Park image
3003 Ash Park Point, Winter Park $379,000

You will fall in love with this absolutely adorable 3 bed 2 bath pool home located in the Hyde Park community of Seminole County. This highly sought after Winter Park ho...

  • 3 Beds
  • 2 Baths
  • Hyde Park SubDv.
  • 32792 Zip Code
7143 Grove Avenue, Winter Park image
7143 Grove Avenue, Winter Park $399,900

Move in ready, 3 bedrooms, 2 bathrooms completely renovated home in great location. This beautiful house features an open concept kitchen with stainless steel appliances ...

  • 3 Beds
  • 2 Baths
  • Brookside Subdivision SubDv.
  • 32792 Zip Code
656 Worthington Drive, Winter Park image
656 Worthington Drive, Winter Park $850,000

Spacious, updated and immaculate 4/3.5 POOL Executive home with almost 3000 sq ft, is awaiting it’s new owner. Full of delightful entertaining space, office and an overs...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
315 E New England Avenue Unit 11, Winter Park image
315 E New England Avenue Unit 11, Winter Park — 315 $1,380,000

Centrally located 2-blocks from Park Avenue with easy access to shops, restaurants and Central Park. This stylish condo offers 3-bedrooms with an open floor plan full of ...

  • 3 Beds
  • 2 Baths
  • Villa Siena SubDv.
  • 32789 Zip Code
911 Osceola Avenue, Winter Park image
911 Osceola Avenue, Winter Park $949,000

One of a kind lot in walking distance to Park Avenue, Alfond Inn and Rollins Collège. Come build the home of your dreams on this oversized lot, current home is immaculate...

  • Osceola Shores Sec 01 SubDv.
  • 32789 Zip Code
1485 Westchester Avenue, Winter Park image
1485 Westchester Avenue, Winter Park $634,900

Only steps from the upscale shops and restaurants of Orlando Avenue, Park Avenue, and Downtown Orlando. This prime location is highly coveted, offering everything you see...

  • 3 Beds
  • 2 Baths
  • Westminster SubDv.
  • 32789 Zip Code
861 Mayfield Avenue, Winter Park image
861 Mayfield Avenue, Winter Park $999,900

Modern and spacious, this RARE Mid-Century Modern home, designed by Frank Sheehy is nestled amongst Alabama Oaks subdivision and just steps away from LAKE MAITLAND. Locat...

  • 4 Beds
  • 3 Baths
  • Alabama Oaks SubDv.
  • 32789 Zip Code
3127 Heartleaf Pl, Winter Park image
3127 Heartleaf Pl, Winter Park $375,000

Check out this beautiful move-in-ready 3 bedroom with office/den, 2 bath home located in the highly sought out subdivision of Lost Creek in Winter Park, Seminole County. ...

  • 3 Beds
  • 2 Baths
  • Lost Creek SubDv.
  • 32792 Zip Code
2724 Lion Heart Road, Winter Park image
2724 Lion Heart Road, Winter Park $400,000

Welcome to the Winter Park Pines, with tree-lined streets and the mailman that delivers to your door! This beautiful 4 bedroom, 2 bathroom home in the Winter Park Pines i...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines Rep SubDv.
  • 32792 Zip Code
164 Brewer Avenue, Winter Park image
164 Brewer Avenue, Winter Park $1,100,000

Nestled in the heart of Winter Park, this fully renovated Colonial Revival home with 1/1 guest house offers a welcoming place of retreat for the entire family. Step insid...

  • 5 Beds
  • 4 Baths
  • Cortland Park SubDv.
  • 32789 Zip Code
393 Sylvan Drive, Winter Park image
393 Sylvan Drive, Winter Park $629,000

Mid-Century, LAKEFRONT home located in the “heart of Winter Park!” This 3 Bedroom, 2.5 Bath home is situated on a ½ acre lot with mature landscaping and a magnificent Liv...

  • 3 Beds
  • 2 Baths
  • Sylvan Park SubDv.
  • 32789 Zip Code
1551 Harris Circle, Winter Park image
1551 Harris Circle, Winter Park $1,275,000

This stunning 4 bed 2.5 bath home situated in the heart of Winter Park on over 60' of Lake Sylvan frontage has been recently renovated and perfect for family living or en...

  • 4 Beds
  • 2 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
1503 Michigan Avenue, Winter Park image
1503 Michigan Avenue, Winter Park $399,000

Great Duplex in Winter Park. One side leased and the other vacant. This Duplex is close to the interstate and to Winter Park Village . Private off street parking. Laundr...

  • Lawndale SubDv.
  • 32789 Zip Code
1316 Monte Lane, Winter Park image
1316 Monte Lane, Winter Park $329,000

Beautiful charming, cul-de sac, 3 Bedrooms/ 2 Bath home in Winter Park! NO HOA! This home offers a lovely floorplan, and many updates, 2017 kitchen with granite count...

  • 3 Beds
  • 2 Baths
  • Casa Aloma SubDv.
  • 32792 Zip Code
1987 Biscayne Drive, Winter Park image
1987 Biscayne Drive, Winter Park $330,000

Beautiful Winter Park Home! Fully renovated just a few years ago! This home features an Open Floor plan as you enter the front door with a Living Room/Kitchen combo, Newe...

  • 3 Beds
  • 3 Baths
  • Karolina On Killarney SubDv.
  • 32789 Zip Code
3130 Heartwood Avenue, Winter Park image
3130 Heartwood Avenue, Winter Park $330,000

Superb home in a great location with wonderful schools. This well priced home is on a tree shaded street in a well established area. This wonderful three Bedroom home is ...

  • 3 Beds
  • 2 Baths
  • Bel Aire Pines SubDv.
  • 32792 Zip Code
780 Pinetree Road, Winter Park image
780 Pinetree Road, Winter Park $1,995,000

New Listing in The Vias. Custom built, this 4 bedroom, 5 full bath pool home sits within Winter Park’s most sought-after neighborhood. Surrounded by multi-million dollar ...

  • 4 Beds
  • 5 Baths
  • Sicilian Shores Rep 02 SubDv.
  • 32789 Zip Code
1945 Albert Lee Parkway, Winter Park image
1945 Albert Lee Parkway, Winter Park $325,900

COME QUICK, BEAUTIFUL WINTER PARK HOME! THIS GEM HAS THE ORIGINAL WOOD FLOORS, BEAUTIFUL OPEN FLOOR PLAN WITH MANY GREAT REMODEL POTENTIALS...HOME ALREADY HAS NEWER WIND...

  • 3 Beds
  • 2 Baths
  • Albert Lee Ridge Subdivision SubDv.
  • 32789 Zip Code
429 S Ranger Boulevard, Winter Park image
429 S Ranger Boulevard, Winter Park $434,000

This is the Home Sweet Home your family has been searching for. With solid bones, the home was recently refreshed for the things that matter. Winter Park neighborhood a...

  • 4 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
1550 Grand Road, Winter Park image
1550 Grand Road, Winter Park $870,000

This last of a kind opportunity property is located at the corner of Lake Howell Road and Grand Rd. in southern unincorporated Seminole County, Winter Park, FL. 3.48 Acre...

  • N/A SubDv.
  • 32792 Zip Code
1550 Grand Road, Winter Park image
1550 Grand Road, Winter Park $870,000

This last of a kind opportunity property is located at the corner of Lake Howell Road and Grand Rd. in southern unincorporated Seminole County, Winter Park, FL. 3.48 Acre...

  • N/A SubDv.
  • 32792 Zip Code
1550 Grand Road, Winter Park image
1550 Grand Road, Winter Park $870,000

This last of a kind opportunity property is located at the corner of Lake Howell Road and Grand Rd. in southern unincorporated Seminole County, Winter Park, FL. 3.48 Acre...

  • 4 Beds
  • 2 Baths
  • N/A SubDv.
  • 32792 Zip Code
338 Blue Heron Drive, Winter Park image
338 Blue Heron Drive, Winter Park $760,000

This 3 Bedroom, 3 bath, amazing mid-century modern home has some very unique features. A dramatic open, wood-burning fireplace that separates the living room and family ...

  • 3 Beds
  • 3 Baths
  • Flamingo Shores SubDv.
  • 32789 Zip Code

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