91 total properties
Did you mean the neighborhood Winter Park?
View 1441 ONECO AVENUE Winter Park, FL MLS# O6395705
  • Recently Listed with Virtual Tour
1 of 35
$6,000
4

Beds

3.1

Baths

2,531

Sq.Ft.

1441 ONECO AVENUE

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 220 W READING WAY Winter Park, FL MLS# O6389180
  • Virtual Tour
1 of 37
$5,900
4

Beds

3.0

Baths

2,741

Sq.Ft.

220 W READING WAY

Winter Park, FL

Courtesy of HEWITT RESIDENTIAL, LLC
View 1235 VIA ESTRELLA Winter Park, FL MLS# O6388913
  • Virtual Tour
1 of 14
$5,895
4

Beds

3.0

Baths

2,207

Sq.Ft.

1235 VIA ESTRELLA

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1130 WASHINGTON AVENUE 11C Winter Park, FL MLS# O6384586
$5,495
3

Beds

2.1

Baths

2,069

Sq.Ft.

1130 WASHINGTON AVENUE 11C

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP
View 782 S PENNSYLVANIA AVENUE 1 Winter Park, FL MLS# O6380197
$5,490
3

Beds

2.1

Baths

2,354

Sq.Ft.

782 S PENNSYLVANIA AVENUE 1

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 1640 PALM AVENUE Winter Park, FL MLS# O6393263
  • Recently Listed with Virtual Tour
1 of 37
$5,250
4

Beds

3.0

Baths

1,946

Sq.Ft.

1640 PALM AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 870 CARVER STREET Winter Park, FL MLS# O6397105
  • Recently Listed
1 of 53
$5,150
3

Beds

3.0

Baths

1,875

Sq.Ft.

870 CARVER STREET

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1580 OAKHURST AVENUE Winter Park, FL MLS# O6361638
$4,300
4

Beds

2.1

Baths

2,406

Sq.Ft.

1580 OAKHURST AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 668 OVERSPIN DRIVE Winter Park, FL MLS# O6392773
$4,200
4

Beds

3.0

Baths

2,509

Sq.Ft.

668 OVERSPIN DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1711 CHESTNUT AVENUE Winter Park, FL MLS# O6396000
  • Recently Listed
1 of 41
$4,150
4

Beds

3.0

Baths

2,288

Sq.Ft.

1711 CHESTNUT AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1815 BARKER DRIVE Winter Park, FL MLS# O6386321
  • Virtual Tour
1 of 89
$4,000
4

Beds

2.0

Baths

1,548

Sq.Ft.

1815 BARKER DRIVE

Winter Park, FL

Courtesy of SOTERA LIVING
View 438 W SWOOPE AVENUE Winter Park, FL MLS# O6368619
  • Virtual Tour
1 of 27
$3,995
3

Beds

2.1

Baths

2,317

Sq.Ft.

438 W SWOOPE AVENUE

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 1302 MICHIGAN AVENUE Winter Park, FL MLS# O6371456
  • Virtual Tour
1 of 17
$3,850
3

Beds

2.1

Baths

1,880

Sq.Ft.

1302 MICHIGAN AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 421 W FAIRBANKS AVENUE Winter Park, FL MLS# O6381970
$3,750
3

Beds

3.0

Baths

1,750

Sq.Ft.

421 W FAIRBANKS AVENUE

Winter Park, FL

Courtesy of REALTY ONE GROUP MVP
View 2115 SYCAMORE DRIVE Winter Park, FL MLS# O6398548
  • Recently Listed with Virtual Tour
1 of 23
$3,500
4

Beds

2.0

Baths

2,099

Sq.Ft.

2115 SYCAMORE DRIVE

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 1850 WHITEHALL DRIVE Winter Park, FL MLS# O6385792
  • Virtual Tour
1 of 32
$3,475
3

Beds

2.0

Baths

1,670

Sq.Ft.

1850 WHITEHALL DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 438 LAKEVIEW AVENUE Winter Park, FL MLS# O6396001
  • Recently Listed with Virtual Tour
1 of 24
$3,400
2

Beds

1.0

Baths

1,250

Sq.Ft.

438 LAKEVIEW AVENUE

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 952 FAIRWAY DRIVE Winter Park, FL MLS# G5109152
  • Virtual Tour
1 of 24
$3,300
3

Beds

2.0

Baths

2,007

Sq.Ft.

952 FAIRWAY DRIVE

Winter Park, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 4033 YACHT COURT Winter Park, FL MLS# O6396599
  • Recently Listed with Virtual Tour
1 of 35
$3,000
4

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

Courtesy of NEXTHOME NEIGHBORHOOD REALTY
View 1891 OGLESBY AVENUE Winter Park, FL MLS# O6362840
  • Virtual Tour
1 of 15
$2,970
3

Beds

2.0

Baths

1,195

Sq.Ft.

1891 OGLESBY AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

349

Estimated median home price

$795,000
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

Price Count
$0 - 100K 4
$100K - 200K 50
$200K - 300K 21
$300K - 400K 17
$400K - 500K 28
$500K - 600K 19
$600K - 700K 23
$700K - 800K 14
$800K - 900K 12
$900K - 1M 10
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 212
Townhouse 13
Condo 89
Commercial 3
Rental 91
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 4/15/2026)

Information deemed reliable but not guaranteed.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 4/15/2026.