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.

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Winter Park Homes January 18, 2021
134
Listed
99
Avg. DOM
$368.66
Avg. $ / Sq.Ft.
$809,500
Med. List Price
134 Properties
Page 1 of 12
$995,000
Subdivision: Windsong Elizabeths Walk 43/81
4
Beds
4
Baths
3,237
Sq.Ft.
2003
Year Built
1
Day on Site
O5916958
MLS
Gorgeous two-story Windsong POOL home! You will love this four-bedroom, four full bathroom PLUS OFFICE Winter Park home with 3,237 square feet of perfectly planned space. Special highlights in this...
$1,025,000
Subdivision: Orwin Manor Westminster Sec
4
Beds
4F11/2
Baths
4,077
Sq.Ft.
1946
Year Built
1
Day on Site
O5917575
MLS
Exquisitely designed, expanded & renovated with timeless custom architectural elements throughout. This warm & inviting home is overflowing with charm creating an ambience with high end features that...
$810,000
Subdivision: Lake Killarney Townhomes
3
Beds
3F11/2
Baths
2,341
Sq.Ft.
2020
Year Built
1
Day on Site
O5866966
MLS
Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $798k! Eight exclusive lakefront units offer breathtaking views...
$825,000
Subdivision: Lake Killarney Townhomes
3
Beds
3F11/2
Baths
2,310
Sq.Ft.
2020
Year Built
1
Day on Site
O5912242
MLS
Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $798k! Eight exclusive lakefront units offer breathtaking views...
$854,000
Subdivision: Lake Killarney Townhomes
3
Beds
3F11/2
Baths
2,341
Sq.Ft.
2020
Year Built
1
Day on Site
O5890792
MLS
Completed Model Unit!!! Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $798k! Eight exclusive lakefront units...
$798,000
Subdivision: Lake Killarney Townhomes
3
Beds
3F11/2
Baths
2,310
Sq.Ft.
2020
Year Built
1
Day on Site
O5850903
MLS
Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $798k! Eight exclusive lakefront units offer breathtaking views...
$854,000
Subdivision: Lake Killarney Townhomes
3
Beds
3F11/2
Baths
2,341
Sq.Ft.
2020
Year Built
1
Day on Site
O5911994
MLS
Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $798k! Eight exclusive lakefront units offer breathtaking views...
$639,000
Subdivision: Lake Killarney Homeowners' Association, Inc.
4
Beds
4
Baths
2,631
Sq.Ft.
1960
Year Built
2
Days on Site
O5914885
MLS
DESIREABLE LAKE KILLARNEY CLASSIC HOME WITH MODERN UPDATES JUST BEGINS TO DESCRIBE THIS 4 BEDROOM 4 BATH POOL HOME SEATED ON A CORNER LOT IN THE VERY PRIVATE NEIGHBORHOOD! UNIQUE HOMEOFFERING A LARGE...
$449,000
Subdivision: Osceola Summit
2
Beds
2
Baths
1,454
Sq.Ft.
1946
Year Built
2
Days on Site
O5917389
MLS
Welcome Home to this charming single story 2 bedroom 2 bath home located in desirable Winter Park. Built in 1946, this home exudes charm, boasting original bathrooms and floors. The home offers a...
$925,000
Subdivision: Quail Run
5
Beds
2F11/2
Baths
3,284
Sq.Ft.
1986
Year Built
3
Days on Site
O5888332
MLS
Back on the market!! Owners wanted one more holiday season of memories before parting with their home of 35 years. This home provides a popular 5/2.5 three way split pool home with almost an acre of...
$1,425,000
Subdivision: Campo Bello
5
Beds
4F11/2
Baths
4,108
Sq.Ft.
2021
Year Built
3
Days on Site
O5916753
MLS
Discover an exceptional opportunity in the heart of Winter Park. This beautiful custom-built two-story modern home is very bright with southern exposure on the rear of the home and was developed on a...
$809,000
Subdivision: Timberlane Shores
3
Beds
2F11/2
Baths
2,444
Sq.Ft.
1959
Year Built
4
Days on Site
O5916325
MLS
Absolutely lovely 3-bedroom, 2.5-bath renovated home in highly desirable Timberlane Shores. Split level floor plan with walk out basement to patio and large private fully fenced backyard and...

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.