263 total properties
Did you mean the neighborhood Winter Park?
View 714 DENTON ROAD Winter Park, FL MLS# O6362464
  • Virtual Tour
1 of 27
$449,500
3

Beds

3.0

Baths

1,786

Sq.Ft.

714 DENTON ROAD

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 1695 LEE ROAD E211 Winter Park, FL MLS# L4957574
  • Virtual Tour
1 of 28
$124,990
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD E211

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY SMART 1
View 3021 AARON BURR AVENUE 3 Winter Park, FL MLS# S5138926
$145,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3021 AARON BURR AVENUE 3

Winter Park, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1624 BARCELONA WAY Winter Park, FL MLS# O6362124
  • Virtual Tour
1 of 62
$2,315,000
3

Beds

3.0

Baths

3,828

Sq.Ft.

1624 BARCELONA WAY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361377
  • Virtual Tour
1 of 41
$2,249,900
5

Beds

4.0

Baths

3,948

Sq.Ft.

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1205 MAYFIELD AVENUE Winter Park, FL MLS# O6361935
$2,249,900
Studio

Beds

0.0

Baths

1205 MAYFIELD AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2722 EASTERN PARKWAY Winter Park, FL MLS# O6360734
  • New Construction with Virtual Tour
1 of 14
$2,289,000
5

Beds

4.1

Baths

3,334

Sq.Ft.

2722 EASTERN PARKWAY

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1630 CHESTNUT AVENUE Winter Park, FL MLS# O6360357
  • Virtual Tour
1 of 58
$1,725,000
3

Beds

4.1

Baths

3,164

Sq.Ft.

1630 CHESTNUT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1213 LINDENWOOD LANE Winter Park, FL MLS# O6362048
  • Virtual Tour
1 of 29
$739,900
4

Beds

2.0

Baths

2,505

Sq.Ft.

1213 LINDENWOOD LANE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 870 CARVER STREET Winter Park, FL MLS# O6360210
  • New Construction with Virtual Tour
1 of 53
$949,900
3

Beds

3.0

Baths

1,875

Sq.Ft.

870 CARVER STREET

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1885 TEMPLE DRIVE Winter Park, FL MLS# O6359471
  • Virtual Tour
1 of 65
$2,295,000
5

Beds

3.1

Baths

3,691

Sq.Ft.

1885 TEMPLE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 763 Overspin Drive Winter Park, FL MLS# 256173
$699,000
Studio

Beds

0.0

Baths

763 Overspin Drive

Winter Park, FL

View 102 BELL PLACE Winter Park, FL MLS# O6354345
  • New Construction with Virtual Tour
1 of 78
$1,479,000
4

Beds

3.1

Baths

2,459

Sq.Ft.

102 BELL PLACE

Winter Park, FL

Courtesy of INVESTOR'S REAL ESTATE LLC
View 660 OSCEOLA AVENUE 101 Winter Park, FL MLS# O6353495
$2,295,000
3

Beds

3.1

Baths

2,714

Sq.Ft.

660 OSCEOLA AVENUE 101

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6357615
  • New Construction with Virtual Tour
1 of 50
OPEN HOUSE: Saturday 3/7 12:00 PM - 4:00 PM
$1,375,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 2299 VIA TUSCANY Winter Park, FL MLS# O6355858
  • Virtual Tour
1 of 60
$2,295,000
4

Beds

3.1

Baths

3,986

Sq.Ft.

2299 VIA TUSCANY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
  • Virtual Tour
1 of 30
$645,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1408 CHAPMAN CIRCLE Winter Park, FL MLS# O6357486
  • Virtual Tour
1 of 46
$1,495,000
4

Beds

4.0

Baths

3,237

Sq.Ft.

1408 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2009 CORNELL AVENUE Winter Park, FL MLS# O6353956
  • Virtual Tour
1 of 35
$259,000
2

Beds

1.0

Baths

762

Sq.Ft.

2009 CORNELL AVENUE

Winter Park, FL

Courtesy of ORLANDO HOME DEALER LLC
View 1770 BRYAN AVENUE Winter Park, FL MLS# O6348521
  • Virtual Tour
1 of 7
$800,000
Studio

Beds

0.0

Baths

1770 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

306

Estimated median home price

$725,000
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 5
$100K - 200K 38
$200K - 300K 30
$300K - 400K 19
$400K - 500K 23
$500K - 600K 16
$600K - 700K 17
$700K - 800K 21
$800K - 900K 6
$900K - 1M 8
$1M - Max 123

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 174
Townhouse 14
Condo 83
Commercial 4
Rental 77
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 3/5/2026)

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.

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 3/6/2026.

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 3/6/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 3/6/2026.

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 3/6/2026.