Winter Park

Winter Park is well known for its numerous lakes and unique blend of natural beauty and vibrant, urban lifestyle. Park Avenue is the epicenter of the city showcasing incredible boutique and local shopping opportunities paired with great dining options. Discover some of the finest real estate central Florida has to offer. With real estate ranging from luxury properties, waterfront properties, residential neighborhoods, to condos in the downtown core, there is something for everyone in Winter Park.

Waterfront real estate in Winter Park, Florida Sunset over a lake in Winter Park, Florida

Winter Park Homes For Sale

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1220 North Park Avenue, WINTER PARK


↑ $1,500,000

1220 North Park Avenue, WINTER PARK

7 Beds 7 Baths 12,475 SqFt Residential MLS® # O6012672


4 Isle Of Sicily, WINTER PARK


4 Isle Of Sicily, WINTER PARK

5 Beds 8 Baths 9,522 SqFt Residential MLS® # O6095179


1190 North Park Avenue, WINTER PARK


↓ $1,150,000

1190 North Park Avenue, WINTER PARK

8 Beds 10 Baths 19,619 SqFt Residential MLS® # O6039038


1245 West Fairbanks Avenue, WINTER PARK


1245 West Fairbanks Avenue, WINTER PARK

0 Beds 0 Baths 20,384 SqFt Commercial MLS® # O6077278


1311 Via Tuscany, WINTER PARK


↓ $1,050,000

1311 Via Tuscany, WINTER PARK

7 Beds 8 Baths 10,997 SqFt Residential MLS® # O6011692





4 Beds 5 Baths 5,377 SqFt Residential MLS® # O6090620


1001 Anchorage Court, WINTER PARK


1001 Anchorage Court, WINTER PARK

5 Beds 7 Baths 9,233 SqFt Residential MLS® # O6029320


1750 Via Tuscany, WINTER PARK


1750 Via Tuscany, WINTER PARK

6 Beds 8 Baths 7,644 SqFt Residential MLS® # O6069450


785 Via Lombardy, WINTER PARK


785 Via Lombardy, WINTER PARK

5 Beds 7 Baths 6,736 SqFt Residential MLS® # O6071285


231 Chelton Circle, WINTER PARK


↓ $300,000

231 Chelton Circle, WINTER PARK

5 Beds 7 Baths 5,754 SqFt Residential MLS® # O5999333


466 Henkel Circle, WINTER PARK


↓ $2,000

466 Henkel Circle, WINTER PARK

4 Beds 5 Baths 4,416 SqFt Residential MLS® # O6094004


227 Genius Drive, WINTER PARK


↓ $349,000

227 Genius Drive, WINTER PARK

5 Beds 7 Baths 7,568 SqFt Residential MLS® # O6041348


About Winter Park, FL

In 1881 two New England businessmen Oliver Chapman and Loring A Chase purchased 600 acres bordering four large lakes - Maitland, Osceola, Virginia, and Killarney. This property was commonly referred to as a "necklace" of lakes surrounding the lush landscape that surrounded these lakes. Chapman and Chase planned to create a "planned community" for wealthy Northerners to live in during the winter months. This was the first "planned" community in Florida, and was aptly named "Winter Park". They designed the town around a central park and its main street - Parke Avenue. Soon, homes, churches, schools, markets, and more parks are constructed to make the Northerners feel more comfortable as they fled south from the harsh winter. Soon, pamphlets are sent North with the following verbiage 

“Winter Park is a beautiful winter resort for well-to-do people who wish to escape from the cold and blustering weather (which is) so helpful to colds, coughs, diphtheria, consumption, etc; a collection of beautiful villas in the midst of orange-groves upon acre-lots running to the shores of crystal lakes; a dozen or more large first-class hotels scattered along the 2 miles of lake-frontage — a resort that shall be for the winter what Saratoga, Long Branch, etc., are for the summer. SOCIETY is first-class. A social gathering in Winter Park Town Hall will bring together as refined and cultivated a company as can be found anywhere, representing nearly every State. “

Today, Winter Park offers some of the best dining, shopping, living, and entertainment experiences in all of Florida.  Park Avenue is still the "Main Street" and can be explored by foot, bike, car, or even by train. Dozens of shops, restaurants, and museums line the street making it one of the most enchanting walks in all of Central Florida

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Winter Park Attractions

Winter Park is well known for its many lakes and unique blend of natural beauty and vibrant, urban lifestyle. With so many different places to eat, drink, explore, or even boat - you will never feel like you don't have anything to do! If you would like to explore by foot, by car, by train, or even on one of their famous Canoe tours, you have the ability to explore the beautiful city and all of its history.

Winter Park also loves its art, but the epicenter of this city is definitely Park Avenue, a busy cobblestone street that truly has something for everyone. Some incredible boutique and local shopping can be found here, including some of the best dining experiences you’ll find in Florida. 

Award-winning chefs and restaurants create and cook delicious dishes at restaurants like The Ravenous Pig, a James Beard-nominated establishment.

There are nearly 70 parks in Winter Park and even more in neighboring Maitland, great recreational opportunities are plentiful supply. Winter Park and Maitland also host a variety of annual food, culture, and music festivals.

Winter Park Real Estate

Winter Park real estate offers some of the very best that Florida has to offer. Discover are luxury properties, waterfront properties, residential neighborhoods, or choose to be at the center of it all in the downtown core.

Winter Park homes for sale tend to be more expensive, luxury estates with massive yards listed at over a million dollars. The real estate market in Winter Park showcases several architectural styles, including classic Georgian, Florida, Mediterranean, modern, and more. There’s also vacant land available here with plenty of acres to build on and direct beach access.

Incredible features are found in all of the custom-built homes here in Winter Park, Florida. Every property is unique, but many of these features can include coffered ceilings, gas fireplaces, magnificent double staircases made of iron and wood, and sliding glass doors that extend to a private backyard with beach access and a pool area.

Interior features in these impressive estates with open concept layouts can include crown molding, high ceilings, impressive foyers, stone counters, wood cabinetry, and more. Three and four-bedroom options are the most common floor plans in these single-family homes but can reach as many as eight.

Families are delighted to have access to numerous top-rated schools in Winter Park as well as neighboring Maitland.


What is Winter Park known for?

Winter Park, Florida is known for its picturesque downtown area, which features a variety of shops, restaurants, and art galleries. The city is also known for its historic homes and buildings, numerous parks and lakes, and cultural offerings. Additionally, the city is known for its excellent schools and its proximity to major attractions in the Orlando area, such as Disney World and Universal Studios.

How far is Winter Park from Orlando?

Winter Park is approximately 18 miles northwest of Orlando. The drive typically takes around 30-40 minutes, depending on traffic conditions.

Is Winter Park a good place to live?

Winter Park, Florida is generally considered to be a desirable place to live. It is a well-established and affluent community with a strong sense of community, great schools, and a variety of recreational activities. The city is home to many parks and recreational areas, including the Winter Park Chain of Lakes, which offers boating, fishing, and other water-based activities. Additionally, Winter Park is known for its vibrant downtown area, which features a variety of shops, restaurants, and cultural venues. Overall, many people find Winter Park to be a great place to live, work, and raise a family.

Are there good schools in Winter Park?

Families will find a number of great schools in the Winter Park area. Some of the top-rated schools include:

  • Winter Park High School

  • Trinity Preparatory School

  • Lakemont Elementary School

  • Glenridge Middle School

  • Aloma Elementary School

  • Brookshire Elementary School

  • Lake Howell High School

What is the housing market like in Winter Park?

The housing market in Winter Park, Florida is currently strong and stable. Home prices have been steadily increasing over the past few years. The demand for housing in Winter Park is high, with many buyers looking to move to the area for its excellent schools, charming downtown, and proximity to Orlando. The market is competitive, with many homes receiving multiple offers. Overall, the housing market in Winter Park is considered to be a good investment opportunity for both buyers and sellers.

Winter Park Real Estate Stats

Average Home Price $527K
Lowest Listing Price $0
Highest Listing Price $218M
Total Property Listings 394,244
Avg. Days On Market 181
Avg. Price/SQFT $314

Property Types (active listings)

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