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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

926 Bungalow Avenue, Winter Park image
926 Bungalow Avenue, Winter Park $475,000

Location! Location! Location!. This well appointed home is in the heart of Winter Park and perfectly situated on a classic brick street. You can walk or bike to Park Ave...

  • 3 Beds
  • 3.5 Baths
  • Bungalow Park SubDv.
  • 32789 Zip Code
363 N Phelps Avenue, Winter Park image
363 N Phelps Avenue, Winter Park $699,000

Prepared to be amazed by this 4-bedroom, 3-full-bath custom pool home boasting over 2800sqft of living space and located in desirable Winter Park! Upon entering the home,...

  • 4 Beds
  • 3 Baths
  • Sylvan Park SubDv.
  • 32789 Zip Code
3313 Olde Wharf Run, Winter Park image
3313 Olde Wharf Run, Winter Park $514,000

This completely remodeled and updated home located in Winter Park, Florida looks and feels like brand new construction! Completely renovated by Collective Property Invest...

  • 4 Beds
  • 2.5 Baths
  • Pelican Bay SubDv.
  • 32792 Zip Code
2400 Venetian Way, Winter Park image
2400 Venetian Way, Winter Park $2,195,000

Elegant waterfront residence in Winter Park! This impeccable Mediterranean home features 5 bedrooms and 4 bathrooms and is located on Howell Creek canal off Lake Maitland...

  • 5 Beds
  • 4.5 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
716 Roughbeard Road, Winter Park image
716 Roughbeard Road, Winter Park $415,000

*First time on the market in over 34 years* Located on a perfectly landscaped lot in Winter Park, you will love this warm and spacious one-story POOL home in the Winter...

  • 4 Beds
  • 3 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
Winter Park image
Winter Park $2,150,000

Entertain! Entertain! Entertain! Beautiful 2018 Custom built Winter Park lake front home on one of the most desired lakes in the area. This home features all the amenitie...

  • 5 Beds
  • 4.5 Baths
  • 32792 Zip Code
1764 Mondrian Circle, Winter Park image
1764 Mondrian Circle, Winter Park — Lot 7 $660,750

Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer pr...

  • 3 Beds
  • 3.5 Baths
  • Lake Killarney Townhomes SubDv.
  • 32789 Zip Code
5123 Goldenrod Place Road, Winter Park image
5123 Goldenrod Place Road, Winter Park $315,000

Don’t miss this beautiful and spacious 3 BR/2 BA family home centrally located in Winter Park, with no HOA and zoned for the highly sought-after Seminole County Schools! ...

  • 3 Beds
  • 2 Baths
  • Goldenrod Place SubDv.
  • 32792 Zip Code
1762 Mondrian Circle, Winter Park image
1762 Mondrian Circle, Winter Park — Building 1 $660,750

Pre-Construction. To be built. Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. La...

  • 3 Beds
  • 3.5 Baths
  • Lake Killarney Townhomes SubDv.
  • 32789 Zip Code
1252 Valley Creek Run, Winter Park image
1252 Valley Creek Run, Winter Park $439,900

Come take a look at this incredible modern Fontana Signature Home! This property is fully renovated and redesigned from top to bottom! It features 4 large bedrooms, 3 ful...

  • 4 Beds
  • 3 Baths
  • Lost Creek SubDv.
  • 32792 Zip Code
1760 Mondrian Circle, Winter Park image
1760 Mondrian Circle, Winter Park — Lot 5 $660,750

Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer pr...

  • 3 Beds
  • 3.5 Baths
  • Lake Killarney Townhomes SubDv.
  • 32789 Zip Code
56211 Winterbrook Way, Winter Park image
56211 Winterbrook Way, Winter Park $477,930

Pre-Construction. To be built. BRAND NEW HOME WITH WINTER PARK ADDRESS! PRIVATE GATED COMMUNITY! Spacious 2-story home with 5 bedrooms, 4 bathrooms plus a game room. Loca...

  • 5 Beds
  • 4 Baths
  • Winterbrook SubDv.
  • 32792 Zip Code
5625 Winterbrook Way, Winter Park image
5625 Winterbrook Way, Winter Park $447,170

Under Construction. MUST SEE BRAND NEW CONSTRUCTION WITH WINTER PARK ADDRESS! Spacious 4 Bedrooms, 2.5 Baths, 2 car garage with 2162 sq.ft. This stunning single story hom...

  • 4 Beds
  • 2.5 Baths
  • Winterbrook SubDv.
  • 32792 Zip Code
311 E Morse Boulevard Unit 2-4, Winter Park image
311 E Morse Boulevard Unit 2-4, Winter Park — 2 $899,000

WINTER PARK LAKEFRONT CONDO! Breathtaking views of Lake Osceola, part of the Chain-of-Lakes await you from this charming 2-bedroom & 2-bath remodeled condominium in Winte...

  • 2 Beds
  • 2 Baths
  • Phillips Circle Rep SubDv.
  • 32789 Zip Code
650 Williams Drive, Winter Park image
650 Williams Drive, Winter Park $1,195,000

Welcome to Park Grove - one of the premier neighborhoods that Winter Park has to offer. Situated on a sprawling corner lot, this traditional chic masterpiece is just min...

  • 5 Beds
  • 4 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
1315 Devon Road, Winter Park image
1315 Devon Road, Winter Park $419,000 ▼

One or more photo(s) has been virtually staged. Nestled on a quiet street in one Orlando's most sought-after neighborhoods, this bright, open and updated four bedroom hom...

  • 4 Beds
  • 2 Baths
  • Orwin Manor (Westminster) SubDv.
  • 32789 Zip Code
1773 Grinnell Terrace, Winter Park image
1773 Grinnell Terrace, Winter Park $569,000

Custom Winter Park home meticulously cared for with one owner is move in ready! The covered front porch welcomes friends and family into this 3/2 split plan with an abund...

  • 3 Beds
  • 2 Baths
  • Fremar SubDv.
  • 32789 Zip Code
1540 Ibis Court, Winter Park image
1540 Ibis Court, Winter Park $824,900

<p>Welcome to one of Winter Park’s most desired neighborhoods – just a short walk to Park Avenue’s shops and restaurants and zoned for the area’s best schools. This home ...

  • 3 Beds
  • 2.5 Baths
  • Winflor Court Pt Rep SubDv.
  • 32789 Zip Code
1631 Meadowgold Court, Winter Park image
1631 Meadowgold Court, Winter Park $305,000

Move right in to this Charming up to date home with a brand new roof on a spacious culdesac lot. Features include a brand new LVT flooring throughout the home, sleek whit...

  • 3 Beds
  • 2 Baths
  • Autumn Glen Ph 3 SubDv.
  • 32792 Zip Code
1001 Manchester Circle, Winter Park image
1001 Manchester Circle, Winter Park $324,900

BEAUTIFUL RENOVATED WINTER PARK HOME! Split bedroom 3/2 on a large fenced corner lot. Updated with new kitchen, baths, flooring, A/C system, plumbing, interior & exterior...

  • 3 Beds
  • 2 Baths
  • Howell Estates SubDv.
  • 32792 Zip Code
2031 Temple Drive, Winter Park image
2031 Temple Drive, Winter Park $434,200

This home "As-is" requires a heavy renovation, or you can build new to create your dream home on this 8,543 sq ft Winter Park lot. Home will need a new kitchen and baths...

  • 3 Beds
  • 2 Baths
  • Tuscania SubDv.
  • 32789 Zip Code
2180 N Park Avenue Unit Suite 220, Winter Park image
2180 N Park Avenue Unit Suite 220, Winter Park $350,000

Rare opportunity for Park Avenue office suite. Mediterranean office condominium built in 1984 just minutes from downtown Winter Park. Newly updated second floor office ...

  • Park Ave North SubDv.
  • 32789 Zip Code
843 English Court, Winter Park image
843 English Court, Winter Park $625,000

JUST COMPLETED! This BEAUTIFUL MODERN / TRANSITIONAL MASTERPIECE has a CLEAN design that offers an OPEN CONCEPT FLOOR PLAN with WONDERFUL NATURAL LIGHT!!! Entering the ho...

  • 3 Beds
  • 2.5 Baths
  • Tax Equities Inc Rep SubDv.
  • 32789 Zip Code
810 English Court, Winter Park image
810 English Court, Winter Park $615,000

NEW CONSTRUCTION!! This STUNNING TRANSITIONAL / FARMHOUSE American Home has ALL the BELLS and WHISTLES!!! Located in the HEART of WINTER PARK and within walking distance ...

  • 3 Beds
  • 2.5 Baths
  • Tax Equities Inc Rep SubDv.
  • 32789 Zip Code
250 Carolina Avenue Unit 205, Winter Park image
250 Carolina Avenue Unit 205, Winter Park — 250 $379,000

Amazing opportunity to walk to beautiful Park Ave, Gated for your security and pleasure. Park West amenities includes beautiful pool. Tennis Courts. Clubhouse. Beautiful...

  • 2 Beds
  • 2 Baths
  • Park West Condo SubDv.
  • 32789 Zip Code

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