138 total properties
Did you mean the neighborhood Winter Park?
View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
  • Virtual Tour
1 of 45
$455,000
3

Beds

2.0

Baths

1,491

Sq.Ft.

405 LAKE FAIR LANE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
$500,000
3

Beds

2.0

Baths

1,413

Sq.Ft.

512 N LAKEMONT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 7300 DANIEL WEBSTER DRIVE M7 Winter Park, FL MLS# O6388668
$159,000
2

Beds

2.1

Baths

1,108

Sq.Ft.

7300 DANIEL WEBSTER DRIVE M7

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
The time to sell is now! THE TIME TO SELL IS NOW!
View 3027 AARON BURR AVENUE L1 Winter Park, FL MLS# O6390662
$159,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BURR AVENUE L1

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
$525,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1807 HAMMERLIN AVENUE G

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 2779 SANBINA STREET Winter Park, FL MLS# O6388746
$429,000
3

Beds

2.0

Baths

1,405

Sq.Ft.

2779 SANBINA STREET

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$479,900
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 3217 OAK LAWN PLACE 211 Winter Park, FL MLS# O6390713
$175,000
3

Beds

2.0

Baths

1,117

Sq.Ft.

3217 OAK LAWN PLACE 211

Winter Park, FL

Courtesy of SHORES REAL ESTATE
View 200 SAINT ANDREWS BOULEVARD 312 Winter Park, FL MLS# S5145794
$170,000
1

Beds

1.0

Baths

793

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 312

Winter Park, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 2918 ANTIQUE OAKS CIRCLE 25 Winter Park, FL MLS# O6389113
$189,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIRCLE 25

Winter Park, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View Address not provided Winter Park, FL MLS# S5145631
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1 of 11
$430,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View 4858 TANGERINE AVENUE 4858 Winter Park, FL MLS# O6388649
$209,900
2

Beds

2.0

Baths

1,058

Sq.Ft.

4858 TANGERINE AVENUE 4858

Winter Park, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7336 FOREST HILL COURT 240 Winter Park, FL MLS# O6386461
$169,900
2

Beds

1.1

Baths

990

Sq.Ft.

7336 FOREST HILL COURT 240

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2500 LEE ROAD 122 Winter Park, FL MLS# O6384082
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1 of 25
$179,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 122

Winter Park, FL

Courtesy of PINEAPPLE PLACE REALTY, LLC
View 7117 SWALLOW RUN G1 Winter Park, FL MLS# O6385942
$236,800
3

Beds

2.1

Baths

1,565

Sq.Ft.

7117 SWALLOW RUN G1

Winter Park, FL

Courtesy of COMPLETE FLORIDA REALTY LLC
View 1500 GAY ROAD 20D Winter Park, FL MLS# O6385626
  • Virtual Tour
1 of 22
$262,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 20D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 4768 TANGERINE AVENUE 4768 Winter Park, FL MLS# S5144503
$179,000
1

Beds

1.0

Baths

753

Sq.Ft.

4768 TANGERINE AVENUE 4768

Winter Park, FL

Courtesy of PROPERTY OUTLET INTERNATIONAL
View 1000 S SEMORAN BOULEVARD 715 Winter Park, FL MLS# S5144243
$122,990
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 715

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2924 ANTIQUE OAKS CIRCLE 46 Winter Park, FL MLS# S5144196
$195,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2924 ANTIQUE OAKS CIRCLE 46

Winter Park, FL

Courtesy of CENTURY 21 EDGE
View 1695 LEE ROAD E215 Winter Park, FL MLS# O6383089
  • Virtual Tour
1 of 82
$149,990
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E215

Winter Park, FL

Courtesy of FOWLKES REALTY CO

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

399

Estimated median home price

$775,000
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 3
$100K - 200K 41
$200K - 300K 25
$300K - 400K 26
$400K - 500K 29
$500K - 600K 26
$600K - 700K 31
$700K - 800K 22
$800K - 900K 15
$900K - 1M 9
$1M - Max 172

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 262
Townhouse 16
Condo 84
Commercial 7
Rental 71
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/4/2026)

Information deemed reliable but not guaranteed.

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 6/4/2026.

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 6/4/2026.