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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

2417 Lafayette Avenue, Winter Park image
2417 Lafayette Avenue, Winter Park $390,000

Endless possibilities for a buyer or builder looking for a lot in the highly desirable Winter Park zip code! Almost 3000 square feet FAR. Just minutes from I-4, Park Aven...

  • Winter Park Village SubDv.
  • 32789 Zip Code
2417 Lafayette Avenue, Winter Park image
2417 Lafayette Avenue, Winter Park $390,000

Bring your builder! Endless possibilities for a buyer looking for a lot in the highly desirable Winter Park zip code. Just minutes from I-4, Park Avenue, Winter Park Vil...

  • 2 Beds
  • 1 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
2145 Lake Drive Unit A-26, Winter Park image
2145 Lake Drive Unit A-26, Winter Park $499,900

Charming 3 bedroom 2 bathroom home in Winter Park. This lakefront community with neighboring million dollar plus homes. Prime location in Winter Park with easy access t...

  • 3 Beds
  • 2 Baths
  • Killarney Point SubDv.
  • 32789 Zip Code
1583 Orange Avenue, Winter Park image
1583 Orange Avenue, Winter Park $525,000

Charming Orwin Manor Bungalow in Winter Park - Freshly Painted Inside and Out! Beautifully updated, with vintage charm in this solid block historic 1951 home. Gorgeous or...

  • 3 Beds
  • 2 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
1409 Sunset Drive, Winter Park image
1409 Sunset Drive, Winter Park $539,900

Welcome home to your quaint 2-bedroom, 1-bathroom home nestled in the heart of Winter Park. This home includes a newer roof and decking installed in 2021. Electric panel ...

  • 2 Beds
  • 1 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
2413 Winter Park Road, Winter Park image
2413 Winter Park Road, Winter Park $3,150,000

Pre-Construction. To be built. Preparing to break ground on this newest Winter Park opportunity with F.G. Schaub Custom Homes. This Timeless Modern elevation offers a g...

  • 5 Beds
  • 5.5 Baths
  • Parklando 03 SubDv.
  • 32789 Zip Code
Winter Park image
Winter Park $315,000

Great investment, rental or starter home! Winter Park location with Seminole County Schools! Home has been freshly painted inside and out. Terrazzo floors throughout, no ...

  • 3 Beds
  • 1 Baths
  • Suburban Homes SubDv.
  • 32792 Zip Code
2019 Strathaven Road, Winter Park image
2019 Strathaven Road, Winter Park $535,000

Winter Park POOL Home! Beautiful 4 bedroom, 3 full bath Mid-Century Ranch POOL home nestled in Kenilworth Shores of Winter Park! Fantastic location and move in ready! ...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
311 E Morse Boulevard Unit 6-4, Winter Park image
311 E Morse Boulevard Unit 6-4, Winter Park — 6-4 $425,000

Prime location, first floor condo in downtown Winter Park. Whispering Waters Condos on Lake Osceola. Light and bright, enjoy the landscaped view. Updated kitchen, bath an...

  • 1 Beds
  • 1 Baths
  • Phillips Circle Rep SubDv.
  • 32789 Zip Code
2164 Turkey Run, Winter Park image
2164 Turkey Run, Winter Park $1,250,000

The first thing you will notice is how grandly this Colonial inspired home is situated on a gently arcing lot within the tree-lined streets of Quail Hollow. With nearly 4...

  • 5 Beds
  • 3.5 Baths
  • Quail Hollow SubDv.
  • 32789 Zip Code
2020 Cornell Avenue, Winter Park image
2020 Cornell Avenue, Winter Park $349,000

Duplex

  • 3 Beds
  • Stansbury Estates SubDv.
  • 32789 Zip Code
2620 Lotafun Avenue, Winter Park image
2620 Lotafun Avenue, Winter Park $520,000

Location, location, this amazing opportunity to build your DREAM HOME is here for you in prime location of Winter Park. The key and main value here is in the LAND!!!!. ...

  • 3 Beds
  • 1 Baths
  • Justamere Camp Rep SubDv.
  • 32789 Zip Code
3604/3606 Leanne Court, Winter Park image
3604/3606 Leanne Court, Winter Park $449,999

Great location for a duplex residential in Winter Park! Each side has 3 bedrooms 2 full bathrooms 1 car garage and a covered patio in back yard. Privately fenced propert...

  • 6 Beds
  • 4 Baths
  • University Garden SubDv.
  • 32792 Zip Code
630 W Swoope Avenue, Winter Park image
630 W Swoope Avenue, Winter Park $350,000

This Central Winter Park location, one mile from the Winter Park Mall provides a rare opportunity for investors.

  • 2 Beds
  • 1 Baths
  • Carver Town First Add SubDv.
  • 32789 Zip Code
1568 Little Wren Lane, Winter Park image
1568 Little Wren Lane, Winter Park — N/A $475,000

Welcome to this Luxury townhome in the highly sought after HAWKS CREST Community in Winter Park! Enter through a modern key-less entry door with RING doorbell. In the...

  • 3 Beds
  • 2.5 Baths
  • Enclave At Hawks Crest SubDv.
  • 32792 Zip Code
1700 Winter Park Road, Winter Park image
1700 Winter Park Road, Winter Park $1,089,000

Location! Location! Location! Don't miss out on this beautiful home in the heart of Winter Park! One block from Lake Virginia and just minutes from amazing shopping, dini...

  • 3 Beds
  • 3 Baths
  • Charmont SubDv.
  • 32789 Zip Code
283 N Ranger Boulevard, Winter Park image
283 N Ranger Boulevard, Winter Park $574,900

Stunning, newer renovated, contemporary Winter Park Pines pool home. Highly desirable neighborhood, with excellent Winter Park schools. Steps from popular Cady Way walkin...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
3114 Heartleaf Pl, Winter Park image
3114 Heartleaf Pl, Winter Park $679,900 ▲

It is all about LOCATION, LOCATION, LOCATION!! This beautiful spacious Winter Park home is located in the Lost Creek subdivision, a very private community with no rear ne...

  • 4 Beds
  • 3 Baths
  • Lost Creek SubDv.
  • 32792 Zip Code
3130 Lowndes Drive, Winter Park image
3130 Lowndes Drive, Winter Park $425,000

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

  • 3 Beds
  • 2 Baths
  • Georgetown Estates SubDv.
  • 32792 Zip Code
616 Worthington Drive, Winter Park image
616 Worthington Drive, Winter Park $899,000

Welcome home to this thoughtfully renovated house in a desirable Winter Park neighborhood. Built in 1958, the property has only had two owners and has been maintained and...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
472 Fletcher Place, Winter Park image
472 Fletcher Place, Winter Park $2,100,000

Winter Park custom home on a quiet street with lake access to Winter Park Chain of Lakes on Lake Osceola at end of street. This four-bedroom, four-and-a-half-bath home is...

  • 4 Beds
  • 4.5 Baths
  • Sorensen Heights SubDv.
  • 32789 Zip Code
1209 Sharon Place, Winter Park image
1209 Sharon Place, Winter Park $1,699,000

Excellent opportunity to build your dream home near The Vias in Winter Park. Oversized 108x152, 0.38 acre lot. Existing structure on the site has no value - value is in t...

  • Sharon Place SubDv.
  • 32789 Zip Code
1209 Sharon Place, Winter Park image
1209 Sharon Place, Winter Park $1,699,000

Excellent opportunity to build your dream home near The Vias in Winter Park. Oversized 108x152, 0.38 acre lot. Existing structure on the site has no value - value is in t...

  • 4 Beds
  • 3 Baths
  • Sharon Place SubDv.
  • 32789 Zip Code
2808 Amsden Road, Winter Park image
2808 Amsden Road, Winter Park $540,000

Enjoy all Winter Park has to offer! This Winter Park Estates home is ready for a new owner. This house was meticulously taken care of. Completed renovated inside and out!...

  • 3 Beds
  • 3.5 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
280 E Lake Sue Avenue, Winter Park image
280 E Lake Sue Avenue, Winter Park $1,789,900

Pre-Construction. To be built. Customize-to-suite this gorgeous Bermudan-style landmark home in the heart of Olde Winter Park! Presented by by Parade of Homes Winner, Wo...

  • 5 Beds
  • 4 Baths
  • Charmont SubDv.
  • 32789 Zip Code

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