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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

830 Juanita Rael, Winter Park image
830 Juanita Rael, Winter Park $1,114,877

This amazing 4 bedroom, 3-1/2 bath light bright pool home is meticulously maintained on a large corner lot in the highly desirable oak-lined streets just north of Park Av...

  • 4 Beds
  • 3 Baths
  • Green Oaks Rep 03 SubDv.
  • 32789 Zip Code
104 Longbranch Road, Winter Park image
104 Longbranch Road, Winter Park $580,000

A RARE chance to own a custom built, one of a kind home situated on .69 of an acre in WINTER PARK with brand new roof in 2021! Enter through the front doors, and you wi...

  • 4 Beds
  • 2 Baths
  • Lake Ann Estates Unit 2 SubDv.
  • 32792 Zip Code
1256 Formosa Avenue Unit 6, Winter Park image
1256 Formosa Avenue Unit 6, Winter Park — 1 $459,900 ▲

Under Construction. New Construction - Winter Parks Newest Address - UrbanGreen12 is an exciting new townhome community just steps from everything Winter Park and College...

  • 3 Beds
  • 3 Baths
  • Urban Green 12 SubDv.
  • 32789 Zip Code
1741 Glencoe Road, Winter Park image
1741 Glencoe Road, Winter Park $2,250,000

Magnificent custom home offers Luxury, Location & Lifestyle! (4) Bedrooms + Office/Den + Bonus Room. (4) Full baths + (1/2) Bath. Professional Designer has made signific...

  • 4 Beds
  • 4 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
3176 Ash Park Loop, Winter Park image
3176 Ash Park Loop, Winter Park $369,000

Fabulous Curb Appeal! You will fall in love with this absolutely adorable meticulously landscaped 3 bed 2 bath home located in the Hyde Park community of Seminole County....

  • 3 Beds
  • 2 Baths
  • Hyde Park SubDv.
  • 32792 Zip Code
3084 Coral Vine Lane, Winter Park image
3084 Coral Vine Lane, Winter Park $569,000

WATERFRONT, LAKE ACCESS, HUGE CORNER LOT! This exquisite property is located in beautiful Winter Park. This nearly 1 acre estate is situated on a beautifully landscaped c...

  • 4 Beds
  • 3 Baths
  • Lost Creek SubDv.
  • 32792 Zip Code
1785 Hollywood Avenue, Winter Park image
1785 Hollywood Avenue, Winter Park $450,000

Welcome home! Located in an incredible area, you’ll be just minutes away from the restaurants and boutiques of downtown Winter Park, Baldwin Park, and downtown Orlando. L...

  • 3 Beds
  • 2 Baths
  • Golfview Heights SubDv.
  • 32789 Zip Code
2924 Scarlet Road, Winter Park image
2924 Scarlet Road, Winter Park $425,000

BRAND NEW ROOF JULY 2021!! FRESHLY PAINTED EXTERIOR JULY 2021! Here in Winter Park Pines, where the mailman still delivers to your door and sidewalks line both sides of t...

  • 4 Beds
  • 3 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
2125 Linden Road, Winter Park image
2125 Linden Road, Winter Park $385,000

You'll love this newly remodeled 1950's mission-style home in beautiful Winter Park with a Modern Farmhouse flare. This home is situated on a large corner lot in a quiet,...

  • 4 Beds
  • 2 Baths
  • Ridge High Sub SubDv.
  • 32792 Zip Code
5039 Ferncrest Drive, Winter Park image
5039 Ferncrest Drive, Winter Park $319,990

**YOUR SEARCH STOPS HERE** **NO HOA** **POOL HOME** **NEW ROOF & A/C** This IMMACULATE 3/2 POOL home is sure to impress even the pickiest buyer. Equipped with a NEW ROOF ...

  • 3 Beds
  • 2 Baths
  • Woodcrest Unit 01 SubDv.
  • 32792 Zip Code
1331 College Point, Winter Park image
1331 College Point, Winter Park $2,800,000

Vacant lot! House on the lot is in the process of being demolished.Build your dream home on this beautiful lot on the shores of lake Virginia in the heart of Winter Park....

  • Virginia Heights SubDv.
  • 32789 Zip Code
2344 Woodcrest Drive, Winter Park image
2344 Woodcrest Drive, Winter Park $425,000

This beautiful 3 bedroom 2 bath home is located in the heart of Kenilworth Shores in desirable Winter Park. Great open floor-plan with an office/den space along with a la...

  • 3 Beds
  • 2 Baths
  • Kenilworth Estates 1st Add SubDv.
  • 32792 Zip Code
1364 Tierra Circle, Winter Park image
1364 Tierra Circle, Winter Park $345,000

THESE FOUR BEDROOMS, TWO BATHS HOME, WITH A LARGE FENCE YARD LOCATED IN A HIGHLY DESIRABLE AREA WITH HIGH RATING SCHOOLS IS IDEAL FOR A LARGE FAMILY. THE LARGE SIZE BEDRO...

  • 3 Beds
  • 2 Baths
  • Casa Aloma SubDv.
  • 32792 Zip Code
1540 Glencoe Road, Winter Park image
1540 Glencoe Road, Winter Park $1,750,000 ▲

Private deeded lake access (see pics) to Lake Virginia on the Winter Park chain of lakes, this home is located on one of the most sought after tree-lined brick streets in...

  • 5 Beds
  • 4 Baths
  • Virginia Heights SubDv.
  • 32789 Zip Code
1380 Michigan Avenue, Winter Park image
1380 Michigan Avenue, Winter Park $600,000

LOCATION, LOCATION, LOCATION! Fantastic investment or development opportunity to build either your dream home or a multifamily home properties on this incredible street. ...

  • 3 Beds
  • 1 Baths
  • H Vanwies Sub SubDv.
  • 32789 Zip Code
346 S Ranger Boulevard, Winter Park image
346 S Ranger Boulevard, Winter Park $399,000

This gorgeous three bedroom home on a corner lot is located in sought after Winter Park Pines. Extremely well kept home with engineered wood floors and crown molding. The...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
662 Osceola Avenue Unit 201, Winter Park image
662 Osceola Avenue Unit 201, Winter Park — Perle Du Lac $1,950,000

Welcome Home to PERLE DU LAC, One of Winter Parks most desirable luxury lake front communities. Located on the pristine Lake Virginia with its own private deeded boat sl...

  • 3 Beds
  • 3 Baths
  • Perle Du Lac Condo Or 5843/4848 SubDv.
  • 32789 Zip Code
640 Osceola Avenue, Winter Park image
640 Osceola Avenue, Winter Park — 6 $1,195,000

(*NOTE: There are currently 2 bedrooms, with the 3rd bedroom having been converted to an elegant library/Office.) Welcome to Milano Villas, your turnkey, lakefront commun...

  • 3 Beds
  • 2 Baths
  • Milano At Winter Park SubDv.
  • 32789 Zip Code
2715 Prince John Road, Winter Park image
2715 Prince John Road, Winter Park $430,000

One or more photo(s) has been virtually staged. This Winter Park one-story home offers granite countertops, and a two-car garage.

  • 3 Beds
  • 2 Baths
  • Winter Park Pines Rep SubDv.
  • 32792 Zip Code
1725 Pine Avenue, Winter Park image
1725 Pine Avenue, Winter Park $875,000

Welcome to your charming, traditional Winter Park home! This home boasts 4 bedrooms, 3.5 bathrooms, plus an office with just over 3100 square feet. You will be greeted by...

  • 4 Beds
  • 3 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
1918 Summerfield Road, Winter Park image
1918 Summerfield Road, Winter Park $1,175,000

One or more photo(s) has been virtually staged. Welcome home! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this custom Craftsman s...

  • 5 Beds
  • 4 Baths
  • Kenilworth Shores Section Seven SubDv.
  • 32792 Zip Code
1886 Demetree Drive, Winter Park image
1886 Demetree Drive, Winter Park — 1886 $465,000

The lovely 1-story patio home, located in the community of Waterbridge, combines the ease of living with the convenience of location to create the perfect place to call h...

  • 2 Beds
  • 2 Baths
  • Waterbridge SubDv.
  • 32789 Zip Code
612 Balfour Drive, Winter Park image
612 Balfour Drive, Winter Park $324,900

One or more photo(s) has been virtually staged. FRESHLY PAINTED INTERIOR! Situated in a great Winter Park neighborhood, this property has a fantastic floor plan featuring...

  • 3 Beds
  • 2 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
1021 Fairway Drive, Winter Park image
1021 Fairway Drive, Winter Park $649,000 ▼

GOLF FRONT! Welcome home to this charming estate home on the 9th fairway of Winter Park Pines! All the rooms flow easily throughout this sprawling home! Enter through a ...

  • 4 Beds
  • 3 Baths
  • Golfside Sec 03 SubDv.
  • 32792 Zip Code
1837 Willow Lane, Winter Park image
1837 Willow Lane, Winter Park $478,000

Welcome to your very own tropical oasis! As you walk up to your FRESHLY PAINTED (2021) Winter Park home you are consistently greeted by many Florida native birds and will...

  • 3 Beds
  • 2 Baths
  • Tanglewood Sec 3 Rep SubDv.
  • 32792 Zip Code

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