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 October 25, 2021
102
Listed
69
Avg. DOM
$406.33
Avg. $ / Sq.Ft.
$875,000
Med. List Price
102 Properties
Page 1 of 9
$430,000
Subdivision: Lake Forest Park
3
Beds
1
Baths
1,549
Sq.Ft.
1952
Year Built
1
Day on Site
O5982002
MLS
Investors this is the one you've been looking for. Home sits on .23 acre lot, one of the largest lots in the neighborhood, perfect for your next project.
$600,000
Subdivision: Kenilworth Estates 1St Add
4
Beds
2
Baths
1,681
Sq.Ft.
1963
Year Built
4
Days on Site
O5981269
MLS
New windows providing abundant light and added efficiency. Beautiful, fully renovated Winter Park home. Easy walk to Winter Park High School and close to both downtown Winter Park and Baldwin Park...
$535,000
Subdivision: Park West Condo
2
Beds
2
Baths
1,488
Sq.Ft.
1982
Year Built
4
Days on Site
O5981079
MLS
Gorgeous Winter Park condo with a NYC loft feeling and million-dollar views, and just steps from Park Avenue! Rare opportunity to own a large TOP floor unit in the perfect downtown Winter Park...
$1,850,000
Subdivision: Forest Hills
4
Beds
4
Baths
4,225
Sq.Ft.
1951
Year Built
4
Days on Site
O5981110
MLS
This quintessential Winter Park home was built up on a 0.44-acre corner lot hill, surrounded by brick streets, overlooking Lake Chelton. Built in 1951, it has been expanded and updated over time,...
$415,000
Subdivision: Las Casas De Indiana Condo
3
Beds
2F11/2
Baths
1,616
Sq.Ft.
2008
Year Built
5
Days on Site
O5980870
MLS
This Mediterranean two story townhome feels welcoming and cozy and is full of high end finishes. When you enter the stately double arched wood entry doors, you will discover the bright and spacious...
$750,000
Subdivision: Cortland Park
4
Beds
3F11/2
Baths
2,273
Sq.Ft.
1925
Year Built
5
Days on Site
O5981252
MLS
A must see beautiful 4 bedroom 3 bathroom home in the heart of Winter Park. Minutes away from the renowned strip, Park Ave. Once you enter you are greeted by a welcoming foyer with double doors that...
$1,250,000
Subdivision: Pennsylvania Place Rep
4
Beds
3F11/2
Baths
3,356
Sq.Ft.
2001
Year Built
5
Days on Site
O5973018
MLS
European charmer is located in the highly desired community of Pennsylvania Place (a total of 28 homes) and is walking distance from Park Avenues restaurants, shops, and the favorite Winter Park 9...
$520,000
Subdivision: Acreage & Unrec
3
Beds
3
Baths
2,428
Sq.Ft.
1953
Year Built
6
Days on Site
O5980208
MLS
Amazing Location. Don't miss this Winter Park property before it is gone. Brand new interior paint. Why rent, when you can own this perfectly, located property. FREESTANDING MIXED USE BUILDING in...
$549,000
Subdivision: Killarney Estates
3
Beds
2
Baths
1,925
Sq.Ft.
1949
Year Built
6
Days on Site
O5980574
MLS
Enjoy views of Lake Killarney from this charming late 1940's 3/2 bungalow in Winter Park on a bricked street. Enter into a large living room that is light and spacious opening into a large bonus room....
$732,000
Subdivision: Capens Add
3
Beds
2
Baths
1,930
Sq.Ft.
2021
Year Built
7
Days on Site
O5978961
MLS
Step inside this one of kind, mid-century inspired beauty located in desirable Winter Park. This incredible BRAND NEW home features vaulted ceilings galore. Entering the front door, you immediately...
$469,000
Subdivision: Brookshire Heights 1St Add
3
Beds
2
Baths
1,340
Sq.Ft.
1959
Year Built
11
Days on Site
O5979665
MLS
Come and see this move in ready, fully updated 3 bedroom, 2 full bath, corner lot home in a coveted Winter Park neighborhood! The interior is completely renovated throughout, including a brand new...
$1,607,700
Subdivision: Killarney Circle
3
Beds
2F11/2
Baths
2,812
Sq.Ft.
2001
Year Built
11
Days on Site
O5976053
MLS
Luxury Lifestyle on Beautiful Lake Killarney. Enjoy the serenity of lakeside living on the largest private lake in Winter Park located in the heart of Central Florida. Lake Killarney is the hidden...

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.