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 April 20, 2021
101
Listed
72
Avg. DOM
$403.11
Avg. $ / Sq.Ft.
$895,000
Med. List Price
101 Properties
Page 1 of 9
$2,050,000
Subdivision: Windsong - Lakeside Sec 2
5
Beds
5
Baths
4,622
Sq.Ft.
2002
Year Built
1
Day on Site
O5936822
MLS
This beautiful 5 bedroom, 5 full bath Mediterranean Cahill pool home in the prestigious community of Windsong has been meticulously maintained with an open floor plan perfect for family living &...
$3,850,000
Subdivision: The Greens At Park
4
Beds
4F11/2
Baths
4,901
Sq.Ft.
2021
Year Built
1
Day on Site
O5935400
MLS
Pre-Construction. To be built. Greens at Park. This address says it all 690 N. New York Avenue, where unparalleled luxury meets quintessential Winter Park lifestyle. Iconic English cottage...
$599,000
Subdivision: Fairbanks Park
3
Beds
2F11/2
Baths
1,803
Sq.Ft.
2002
Year Built
1
Day on Site
O5938669
MLS
Granite counter tops/Stainless steel appliances with natural gas burners.
Living area features gas fireplace,bamboo hardwood floors and surround sound speakers.
Private court yard/Great for...
$3,495,000
Subdivision: Osceola Summit
4
Beds
5F11/2
Baths
5,449
Sq.Ft.
1991
Year Built
2
Days on Site
O5936507
MLS
An exquisite European retreat on nearly an acre with lake frontage featuring a private dock across the street, on Lake Osceola on the Winter Park Chain of Lakes. This location is unmatched in...
$795,000
Subdivision: Temple Heights
5
Beds
2F11/2
Baths
2,347
Sq.Ft.
1976
Year Built
2
Days on Site
O5938229
MLS
Sought after and desirable Winter Park. Minutes from Park Ave. This gorgeous 5 bedroom with den/home office, pool home floor plan offers the master suite down stairs. Updated flooring on the first...
$799,000
Subdivision: Charmont
4
Beds
3
Baths
2,605
Sq.Ft.
1945
Year Built
2
Days on Site
O5938372
MLS
Charming updated pool home situated on brick street on a beautiful corner lot in highly desirable Winter Park location. Great curb appeal with rocking chair front porch & swing. Separate formal...
$419,000
Subdivision: Townhomes/Harper Place
3
Beds
2F11/2
Baths
1,661
Sq.Ft.
2005
Year Built
2
Days on Site
O5937162
MLS
Winter Park 3 bed/2.5 bath 1661sf townhome with private rear terrace and 2 stall garage. Well lit living spaces complimented by plantation shutters, wood or tile flooring on first level, updated...
$429,900
Subdivision: Golfside Sec 03
4
Beds
2
Baths
2,155
Sq.Ft.
1973
Year Built
4
Days on Site
O5926812
MLS
One or more photo(s) has been virtually staged. This beautiful 2,155 sq ft pool home with 4 beds and 2 baths sits in a lovely quiet neighborhood that is close to schools and shopping. Recent updates...
Open 4/24
433 Lakeview Ave Winter Park, FL 32789
$625,000
Subdivision: Killarney Estates
3
Beds
2
Baths
1,925
Sq.Ft.
1949
Year Built
5
Days on Site
O5937703
MLS
CHARMING WINTER PARK BUNGALOW! SPECTACULAR LAKE VIEWS! NO HOA! This is a rare
opportunity to live in a serene residential enclave overlooking pristine Lake Killarney with brick streets
and...
$425,000
Subdivision: Townhomes/Harper Place
3
Beds
2F11/2
Baths
1,626
Sq.Ft.
2006
Year Built
6
Days on Site
O5935168
MLS
This gorgeous townhome is centrally located in Winter Park close to Park Avenue, Winter Park Village, Advent Health, Rollins and I-4. Walking distance to shops, restaurants, coffee shops, banks and...
$799,900
Subdivision: Charmont
3
Beds
3
Baths
2,112
Sq.Ft.
1947
Year Built
6
Days on Site
S5049320
MLS
Catch this cozy 3/3 situated on over 1/4 of an acre before the market does! Home features tile floors throughout, open kitchen, classically styled bedrooms/bath with an expansive front and backyard...
$2,250,000
Subdivision: South Interlachen Place
3
Beds
3F21/2
Baths
3,244
Sq.Ft.
2020
Year Built
7
Days on Site
O5930516
MLS
Welcome to South Interlachen Place, an exquisite townhome community, boasting turn-key living at its finest. Showcasing the perfect blend of privacy and accessibility, with high-end finishes in all...

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.