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 September 24, 2022
181
Listed
67
Avg. DOM
$421.55
Avg. $ / Sq.Ft.
$695,000
Med. List Price
181 Properties
Page 1 of 16
$1,650,000
Neighborhood: Northwood Terrace
4
Beds
3F11/2
Baths
3,444
Sq.Ft.
2021
Year Built
1
Day on Site
O6061821
MLS
Welcome home to this two-story contemporary pool home FULL OF UPGRADES featuring four bedrooms plus a large sun-filled office, three and half bathrooms and a two car garage. Welcoming you inside this...
$479,000
Neighborhood: Winter Park Pines
3
Beds
2
Baths
1,656
Sq.Ft.
1966
Year Built
2
Days on Site
O6059983
MLS
WINTER PARK PINES! A highly desirable community within Winter Park, Florida. This home is located on an extremely quiet and private, dead-end street in the neighborhood with easy access to Cady Way...
$695,000
Neighborhood: Meadows At Hawks Crest
4
Beds
2F11/2
Baths
2,196
Sq.Ft.
2019
Year Built
2
Days on Site
O6060477
MLS
Simply Breathtaking! BRAND NEW MODEL HOME WITH POOL! Look no further than this stunning 4 bedroom, 2.5 bathroom, 2 story home that is just waiting to be moved in. This home was the model so the...
Open 9/25
1552 Golfside Dr Winter Park, FL 32792
$559,500
Neighborhood: Greenview At Winter Pines
3
Beds
2
Baths
1,749
Sq.Ft.
1981
Year Built
2
Days on Site
O6062180
MLS
The BEST of both worlds...Water and Golf! Situated on a beautiful pond overlooking the 3rd fairway of the 18-hole Winter Park Pines Golf Course, this three-bedroom, two-bath home offers a nice open...
$1,050,000
Neighborhood: Quail Hollow
5
Beds
3F11/2
Baths
3,400
Sq.Ft.
1974
Year Built
2
Days on Site
O6062202
MLS
This wonderful five-bedroom pool home is located on a quiet cul-de-sac in the lovely Quail Hollow. This waterfront split-level home has been updated throughout the years and features a newer and very...
Open 9/25
1791 Grinnell TERRACE Winter Park, FL 32789
$1,950,000
Neighborhood: Fremar
4
Beds
4
Baths
3,338
Sq.Ft.
2002
Year Built
3
Days on Site
O6059682
MLS
Stunning Winter Park home freshly remodeled in 2021-2022. This home missed no details when it comes to finishes and using the highest quality products. All around the home, you will see beautifully...
$750,000
Neighborhood: Orwin Manor Westminster Sec
3
Beds
2
Baths
2,472
Sq.Ft.
1947
Year Built
3
Days on Site
O6061818
MLS
Orwin Manor STUNNER. This spacious 3 bed, 2 bath * Welcome Home * Live and Entertain in Comfort * This home features a wonderfully open and flowing floor plan that was tastefully and substantially...
$596,000
Neighborhood: Garden Lake Estates Unit 3
3
Beds
2
Baths
1,644
Sq.Ft.
1983
Year Built
4
Days on Site
O6043905
MLS
Tropical paradise with amazing lake views and screened pool. Perfect place to relax on the covered patio at the end of the day or around the fire pit in the backyard. There is an assortment of fruit...
$625,000
Neighborhood: Golfside Sec 03
4
Beds
2
Baths
2,294
Sq.Ft.
1977
Year Built
4
Days on Site
O6060692
MLS
Welcome to this WINTER PARK split floorplan beauty! The home, located near the Winter Park Pines Golf Club with tree lined streets, has so much character. Walking up to home, you will notice the...
$429,900
Neighborhood: Eastbrook Sub Unit 8
3
Beds
2
Baths
1,649
Sq.Ft.
1967
Year Built
4
Days on Site
GC508391
MLS
NEAT & CLEAN 3Bd @ 2Ba in Desirable Winter Park Florida (USA) This home has had many newer renovations in the past couple of years such as but not limited to the remodeled kitchen with granite...
$795,000
Neighborhood: Charmont
3
Beds
2
Baths
1,935
Sq.Ft.
1949
Year Built
4
Days on Site
O6057476
MLS
Located in Historic Winter Park, on a corner lot with brick-paved street you will find this beautifully renovated home full of character.
New Roof in Sept. 2022, Hot Water Heater (2021), New...
Open 9/25
5122 N Woodcrest Dr Winter Park, FL 32792
$425,000
Neighborhood: Woodcrest Unit 01
4
Beds
2
Baths
1,499
Sq.Ft.
1969
Year Built
4
Days on Site
O6061368
MLS
Fully renovated pool home ! Near UCF make it a 4 bedroom or bonus room. Brand new kitchen,bathroom and no carpet with engineered laminate flooring throughout ! 42 inch cabinets with quartz...

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.