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 May 24, 2022
102
Listed
56
Avg. DOM
$462.55
Avg. $ / Sq.Ft.
$777,500
Med. List Price
102 Properties
Page 1 of 9
$470,000
Neighborhood: Winter Woods Unit 02
4
Beds
2
Baths
1,754
Sq.Ft.
1970
Year Built
2
Days on Site
O6027822
MLS
LUSH TROPICAL 4 bedroom, 2 bath block constructed and well cared for SCREEN-ENCLOSED POOL HOME in WINTER WOODS SUBDIVISION located in the Seminole County side of Winter Park. The landscaping is very...
$415,000
Neighborhood: Karolina On Killarney
2
Beds
2
Baths
1,219
Sq.Ft.
1958
Year Built
2
Days on Site
O6027892
MLS
Excellent opportunity to own this beautifully renovated, 2 bedroom/2bath home in Winter Park! Truly a must see, this home boasts New interior and exterior paint, New vinyl flooring throughout, tiled...
$439,900
Neighborhood: Oakcrest-516
3
Beds
2
Baths
1,305
Sq.Ft.
1982
Year Built
2
Days on Site
D6125710
MLS
MUST SEE!! Do not miss out on this updated and charming 3 bedroom 2 bath pool home located in Winter Park, Florida! Beautiful curb appeal will strike your eye as you enter this freshly updated home....
$4,400,000
Neighborhood: Golfview Terrace
4
Beds
4F11/2
Baths
4,617
Sq.Ft.
2013
Year Built
3
Days on Site
O6027718
MLS
Magnificent-Custom Mediterranean Master Piece in prime location of Winter Park.Carefully designed and built by using European influences, this gorgeous estate was planned to meet the needs of the...
$450,000
Neighborhood: Eastbrook Sub Unit 1
4
Beds
2F11/2
Baths
1,919
Sq.Ft.
1959
Year Built
4
Days on Site
O6027637
MLS
Tastefully remodeled Home in Fantastic Location with Excellent rated Schools. Home was just freshly painted inside and out. New Luxury waterproof vinyl plank flooring throughout the entire home,...
$449,900
Neighborhood: Flamingo Shores
4
Beds
2
Baths
1,345
Sq.Ft.
1953
Year Built
4
Days on Site
O6026710
MLS
LOCATION, LOCATION, LOCATION!! Trendy Winter Park location within minutes to Park Ave. and having deeded access to Lake Killarney! Freshly updated, including a NEW ROOF!!! Modern style blends...
$1,500,000
Neighborhood: Sylvan Park
3
Beds
3
Baths
2,525
Sq.Ft.
1915
Year Built
5
Days on Site
O6026771
MLS
An absolute FIND! Over 1/2 acre on private Lake Sylvan, a spring-fed jewel that is teaming with bass and catfish! In the middle of Old Winter Park, sited on a charming brick street, this property...
$650,000
Neighborhood: Golfside Sec 02
4
Beds
2
Baths
2,118
Sq.Ft.
1969
Year Built
5
Days on Site
O6027384
MLS
Welcome home to 921 Golfside! This beautiful split plan house is waiting for you to make it your home! From the canopied street, you'll enter through the foyer and find a formal living room, which...
$400,000
Neighborhood: Eastbrook Sub Unit 05
3
Beds
2
Baths
1,255
Sq.Ft.
1963
Year Built
5
Days on Site
O6027387
MLS
Beautifully updated and move in ready! This lovely one story range home offers 3 bedrooms 2 baths and a stunning backyard oasis with a large swimming pool. The gorgeous backyard is very private...
$534,999
Neighborhood: Sylvan Heights
2
Beds
1
Baths
974
Sq.Ft.
1954
Year Built
5
Days on Site
O6025883
MLS
Live in the epicenter of where EVERYONE wants to live in Central Florida in the Heart of GORGEOUS & EXCLUSIVE Winter Park 32789! The home is nestled in one of the most scenic areas of all of...
$1,295,000
Neighborhood: Winter Park Village
4
Beds
3F11/2
Baths
3,102
Sq.Ft.
2018
Year Built
5
Days on Site
O6027212
MLS
Sleek like-new construction modern-style home with clean lines and simply elegant architecture. This gallery-styled home is in near-perfect, impeccable condition, with everything meticulously...
$805,000
Neighborhood: Golfview
5
Beds
3
Baths
2,327
Sq.Ft.
2022
Year Built
6
Days on Site
O6023632
MLS
Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Walking distance to the historic Dubsdread Golf Course as well as dining 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.