231 total properties
Did you mean the neighborhood Winter Park?
View 1822 GREENWICH AVENUE Winter Park, FL MLS# A4669605
$1,199,900
3

Beds

2.0

Baths

1,627

Sq.Ft.

1822 GREENWICH AVENUE

Winter Park, FL

Courtesy of FLATFEE.COM
View 100 S INTERLACHEN AVENUE 415 Winter Park, FL MLS# O6354679
$1,195,000
2

Beds

2.0

Baths

1,267

Sq.Ft.

100 S INTERLACHEN AVENUE 415

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1150 KENWOOD AVENUE Winter Park, FL MLS# O6355666
  • Virtual Tour
1 of 41
$1,190,000
3

Beds

2.1

Baths

2,557

Sq.Ft.

1150 KENWOOD AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 503 W CANTON AVENUE Winter Park, FL MLS# O6367552
  • Recently Listed with Virtual Tour
1 of 37
$1,157,000
3

Beds

2.1

Baths

2,342

Sq.Ft.

503 W CANTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1611 WALNUT AVENUE Winter Park, FL MLS# O6365438
  • Virtual Tour
1 of 41
$1,150,000
4

Beds

3.0

Baths

2,635

Sq.Ft.

1611 WALNUT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 240 E Lake Sue Ave Winter Park, FL MLS# F10537698
  • Virtual Tour
1 of 15
$1,107,750
2

Beds

2.0

Baths

1,329

Sq.Ft.

240 E Lake Sue Ave

Winter Park, FL

View 2607 LAFAYETTE AVENUE Winter Park, FL MLS# O6314734
$1,095,000
4

Beds

3.1

Baths

2,770

Sq.Ft.

2607 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of FORTUNE INTERNATIONAL REALTY
View 2607 Lafayette Ave Winter Park, FL MLS# A11826269
  • Virtual Tour
1 of 71
$1,095,000
4

Beds

3.1

Baths

2,770

Sq.Ft.

2607 Lafayette Ave

Winter Park, FL

Courtesy of FORTUNE CHRISTIE'S INTERNATIONAL REAL ESTATE
View 632 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6250417
$1,050,000
3

Beds

2.0

Baths

2,342

Sq.Ft.

632 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 2260 HAWICK LANE Winter Park, FL MLS# O6343603
  • Virtual Tour
1 of 5
$995,000
Studio

Beds

0.0

Baths

2260 HAWICK LANE

Winter Park, FL

Courtesy of DAVEN REAL ESTATE INC
View 913 MOSS LANE Winter Park, FL MLS# O6307671
  • Virtual Tour
1 of 38
$975,000
3

Beds

2.0

Baths

1,887

Sq.Ft.

913 MOSS LANE

Winter Park, FL

Courtesy of VECTOR REALTY
View 870 CARVER STREET Winter Park, FL MLS# O6360210
  • New Construction with Virtual Tour
1 of 53
$975,000
3

Beds

3.0

Baths

1,875

Sq.Ft.

870 CARVER STREET

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 250 CORTLAND AVENUE Winter Park, FL MLS# O6290084
  • Virtual Tour
1 of 68
$950,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

250 CORTLAND AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 250 Cortland Avenue Winter Park, FL MLS# 1055403
  • Virtual Tour
1 of 72
$950,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

250 Cortland Avenue

Winter Park, FL

Brevard
View 668 OVERSPIN DRIVE Winter Park, FL MLS# O6351255
  • Virtual Tour
1 of 54
$950,000
4

Beds

3.0

Baths

2,509

Sq.Ft.

668 OVERSPIN DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$949,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1929 S LAKEMONT AVENUE Winter Park, FL MLS# O6364557
$949,000
3

Beds

3.1

Baths

2,160

Sq.Ft.

1929 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Recently Listed with Virtual Tour
1 of 7
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 208 BREWER AVENUE Winter Park, FL MLS# O6330008
  • Virtual Tour
1 of 47
$925,000
4

Beds

3.1

Baths

2,173

Sq.Ft.

208 BREWER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6337355
  • New Construction with Virtual Tour
1 of 11
$916,050
4

Beds

3.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC

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

280

Estimated median home price

$675,000
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 6
$100K - 200K 37
$200K - 300K 19
$300K - 400K 16
$400K - 500K 25
$500K - 600K 22
$600K - 700K 21
$700K - 800K 21
$800K - 900K 4
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 162
Townhouse 19
Condo 70
Commercial 4
Rental 107
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/2/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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.

Data is updated as of 1/2/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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.

Data is updated as of 1/2/2026.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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.

Data is updated as of 1/2/2026.

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.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective 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 1/2/2026.