Homes For Sale In Winter Park FL

Winter Park is home to traditional yet sustainable living.  Winter Park real estateFind homes for sale in Winter Park FL and research local real estate market trends. Search new listings, scheduled open houses, recent solds, and price reductions in Winter Park. To adjust how your search is displayed, click the gray arrows next to "Sort" to display Winter Park homes in Orlando by price, number of bedrooms, or days on market.

If you would like to know more about any of these Winter Park listings, just click the "Ask A Question" button when viewing the details of the property. We can provide you with past sales history, dates and prices of Winter Park homes recently sold nearby, and more. If you'd like to take a tour, click "Schedule A Showing."

Set up and save your own custom home search by clicking the starred "Save" button to register for a free account so that you can receive email alerts whenever new Winter Park properties come on the market.

Winter Park Homes July 28, 2021
129
Listed
55
Avg. DOM
$375.71
Avg. $ / Sq.Ft.
$849,900
Med. List Price
129 Properties
Page 1 of 11
$1,475,000
Subdivision: Virginia Heights Rep
3
Beds
2F21/2
Baths
3,613
Sq.Ft.
1986
Year Built
1
Day on Site
O5919292
MLS
The work of a local award-winning designer, this transitional Winter Park classic features a modern exterior elevation, with ornate compliments of very familiar and local nature. Masterfully crafted...
$1,240,000
Subdivision: Via Merano
4
Beds
3
Baths
3,227
Sq.Ft.
2016
Year Built
1
Day on Site
O5940017
MLS
Gorgeous, immaculate, well appointed Winter Park Home. This modern floor plan with an open concept and spacious layout is conveniently located in the heart of Winter Park. This home has an oversized...
$425,000
Subdivision: Kenilworth Estates 1St Add
3
Beds
2
Baths
1,764
Sq.Ft.
1960
Year Built
1
Day on Site
O5961537
MLS
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 large living/dining area. The...
Open 8/1
1071 Aragon Ave Winter Park, FL 32789
$449,000
Subdivision: Seville Park
2
Beds
2F11/2
Baths
1,851
Sq.Ft.
2008
Year Built
2
Days on Site
O5936084
MLS
Conveniently located between downtown Winter Park and College Park with easy access to shopping, restaurants and highways. Zoned for Audubon Park K-8 for elementary and middle school. All the...
$599,990
Subdivision: Winter Park Heights
4
Beds
2F11/2
Baths
2,087
Sq.Ft.
1972
Year Built
3
Days on Site
O5961244
MLS
This is a FANTASTIC opportunity to own a **POOL HOME** home on a HUGE LOT with STONG BONES in one of the most HIGHLY DESIRABLE locations in Winter Park. NO HOA. This home is located just a short bike...
$600,000
Subdivision: H Vanwies Sub
3
Beds
1
Baths
1,036
Sq.Ft.
1952
Year Built
3
Days on Site
O5956436
MLS
LOCATION, LOCATION, LOCATION! Fantastic investment or development opportunity to build either your dream home or a multifamily home properties on this incredible street. Within a very close distance...
$1,599,000
Subdivision: Virginia Heights
5
Beds
4
Baths
4,545
Sq.Ft.
1986
Year Built
3
Days on Site
O5944753
MLS
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 Winter Park. This newly...
$520,000
Subdivision: Jenkins Second Add
3
Beds
2F11/2
Baths
2,020
Sq.Ft.
1956
Year Built
3
Days on Site
O5959172
MLS
DO NOT MISS OUT ON THIS ONE!! This charming 3-bedroom/2.5 bathroom home is located in a beautiful area of Winter Park. The home features a NEW ROOF as of 2017, a spacious kitchen with plenty of...
$1,950,000
Subdivision: Perle Du Lac Condo Or 5843/4848
3
Beds
3F11/2
Baths
2,290
Sq.Ft.
2003
Year Built
5
Days on Site
O5961025
MLS
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 slip, this property provides...
$450,000
Subdivision: Dixie Terrace
2
Beds
1
Baths
1,627
Sq.Ft.
1956
Year Built
5
Days on Site
O5960940
MLS
This is a CASH only sale. Ideal Park Avenue location, this block home is less than 2 miles to the shops of Park Ave and Winter Park Village. This home will need some renovations and is in a great...
$1,175,000
Subdivision: Kenilworth Shores Section Seven
5
Beds
4F11/2
Baths
3,269
Sq.Ft.
2021
Year Built
6
Days on Site
O5960404
MLS
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 style home brings so much...
$875,000
Subdivision: Conwill Estates
4
Beds
3F11/2
Baths
3,125
Sq.Ft.
1954
Year Built
6
Days on Site
O5960728
MLS
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 a horseshoe driveway...

Winter Park is one of Orlando’s finest cities, it is famous for spectacular homes, abundant parks, world class museums, beautiful lakes, and fine shopping. Winter Park is a city of about $37,000 residents just north of Orlando. With some of the cities best dining experiences, most luxurious homes, and serene nature parks, Winter Park is one of the most desirable places to live in Central Florida.

Winter Park is a small city full of rich history. Starting out as an eight-acre parcel of land purchased in 1858, Winter Park was originally called Lakeview. By 1883, the city expanded by 600 acres and was renamed Winter Park. The city was originally intended to be a winter haven for wealthy northerners seeking refuge from the harsh winters, ergo the new name, a park for the winter. In 1883, Winter Park’s first school opened and quickly following the public library which is still the library today. However, come Spring of 2021, a new public library facility is set to open with world-class, future ready technology. 

 

Ever expanding and changing with the times, Winter Park’s combination of established roots and new construction homes provides the area’s unique charm and pull to live here. There is plenty of tradition in Winter Park but the city also treasures new, eclectic architecture as well. Spanish-roofed architecture is prevalent in the area, but you will also see traditional American styled homes, Mediterranean features, and contemporary styles with playful colors and bright greenery. 

 

Winter park is a Mecca for world-class art and rich cultural experiences. A city filled with art and culture, Winter Park cherishes its traditional charm while building a sustainable future for the generations to come. Considered by many to be a premier urban village in the sunshine state, Winter Park is coined one of the finest cities in the United States. 

 

Winter Park is home to the one and only “Park Ave.” A destination for dining and shopping like none other. With more than 140 upscale boutiques and restaurants, on Park Ave you can find almost anything your heart desires. One night enjoy more laid back traditional Turkish cuisine from Bosphorous and then tomorrow you can treat yourself to a fine dining experience in a five-star environment at Luma on Park. 

 

Winter Park is also home to A-rated elementary, middle and high schools, outstanding and always happening community events, and one of the most amazing college campuses in the US, Rollins College. Whether you are seeking refuge from the cold north and retiring in Winter Park or coming to this unique city to start your family, Winter Park is a city like none other. The demand to live in this traditional, eclectic city is always high.