364 total properties
Did you mean the neighborhood Winter Park?
View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$244,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Virtual Tour
1 of 46
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 4053 COOL WATER COURT Winter Park, FL MLS# O6419831
$549,000
3

Beds

2.0

Baths

1,930

Sq.Ft.

4053 COOL WATER COURT

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

Winter Park, FL

View 321 SYLVAN BOULEVARD Winter Park, FL MLS# O6417674
$1,395,000
3

Beds

2.1

Baths

2,821

Sq.Ft.

321 SYLVAN BOULEVARD

Winter Park, FL

View 140 E MORSE BOULEVARD J Winter Park, FL MLS# O6414891
$2,350,000
3

Beds

3.0

Baths

2,143

Sq.Ft.

140 E MORSE BOULEVARD J

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,849,900
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

Winter Park, FL

View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6418198
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 7/25 12:00 PM - 4:00 PM
$1,262,500
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

View 4756 TANGERINE AVENUE 4756 Winter Park, FL MLS# R4911483
$185,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4756 TANGERINE AVENUE 4756

Winter Park, FL

View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
$899,000
3

Beds

3.1

Baths

1,824

Sq.Ft.

1411 MILLER AVENUE

Winter Park, FL

View 1600 LEGION DRIVE Winter Park, FL MLS# O6415591
  • Virtual Tour
1 of 70
$3,795,000
5

Beds

5.1

Baths

4,483

Sq.Ft.

1600 LEGION DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 200 SAINT ANDREWS BLVD 3206 Winter Park, FL MLS# O6416143
$230,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BLVD 3206

Winter Park, FL

View 1836 WHITEHALL DRIVE Winter Park, FL MLS# O6416158
  • New Construction with Virtual Tour
1 of 70
$3,500,000
5

Beds

6.1

Baths

4,168

Sq.Ft.

1836 WHITEHALL DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Virtual Tour
1 of 49
OPEN HOUSE: Sunday 7/26 2:00 PM - 4:00 PM
$1,450,000
4

Beds

3.1

Baths

3,578

Sq.Ft.

1421 CHAPMAN CIRCLE

Winter Park, FL

View 2323 DEVON COURT Winter Park, FL MLS# O6418530
  • Recently Listed with Virtual Tour
1 of 35
$429,000
4

Beds

2.0

Baths

2,403

Sq.Ft.

2323 DEVON COURT

Winter Park, FL

View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 39
OPEN HOUSE: Saturday 7/25 12:00 PM - 2:00 PM
$2,250,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Virtual Tour
1 of 38
$849,900
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

Winter Park, FL

View 1113 VIA DEL MAR Winter Park, FL MLS# O6416144
  • Virtual Tour
1 of 9
$1,595,000
Studio

Beds

0.0

Baths

1113 VIA DEL MAR

Winter Park, FL

View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
  • Virtual Tour
1 of 36
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

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

375

Estimated median home price

$759,000
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 8
$100K - 200K 43
$200K - 300K 24
$300K - 400K 18
$400K - 500K 31
$500K - 600K 24
$600K - 700K 31
$700K - 800K 15
$800K - 900K 14
$900K - 1M 10
$1M - Max 157

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 229
Townhouse 19
Condo 83
Commercial 11
Rental 66
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 7/25/2026)

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 7/25/2026.

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 7/25/2026.