133 total properties
Did you mean the neighborhood Winter Park?
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 119 OAK GROVE ROAD Winter Park, FL MLS# O6397460
  • Virtual Tour
1 of 13
$285,000
3

Beds

2.0

Baths

1,134

Sq.Ft.

119 OAK GROVE ROAD

Winter Park, FL

Courtesy of INT'L PROFESSIONAL REALTY INC
View 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
$279,990
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1500 GAY ROAD 8D Winter Park, FL MLS# O6392693
$267,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 8D

Winter Park, FL

Courtesy of SOLID OAK REAL ESTATE 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 1500 GAY ROAD 24B Winter Park, FL MLS# O6348568
  • Virtual Tour
1 of 21
$261,500
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 24B

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 3580 WILDE AVENUE Winter Park, FL MLS# O6296776
  • Virtual Tour
1 of 8
$260,000
Studio

Beds

0.0

Baths

3580 WILDE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View Address not provided Winter Park, FL MLS# O6393932
  • Virtual Tour
1 of 30
$257,000
2

Beds

2.1

Baths

959

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of DERENTHAL REALTY
View 7117 SWALLOW RUN G1 Winter Park, FL MLS# O6385942
$249,800
3

Beds

2.1

Baths

1,565

Sq.Ft.

7117 SWALLOW RUN G1

Winter Park, FL

Courtesy of COMPLETE FLORIDA REALTY LLC
View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
  • Virtual Tour
1 of 41
$245,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 229

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 2500 LEE ROAD 202 Winter Park, FL MLS# O6277579
  • Virtual Tour
1 of 39
$234,999
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 202

Winter Park, FL

Courtesy of THE ANDERSON GROUP & CO PL
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Recently Listed with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6381596
$225,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

3371 RIVER VIEW WAY 46

Winter Park, FL

Courtesy of ROBERT SLACK LLC
View 200 SAINT ANDREWS BOULEVARD 2901 Winter Park, FL MLS# O6395720
  • Recently Listed with Virtual Tour
1 of 29
$225,000
2

Beds

1.1

Baths

1,266

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2901

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 200 Saint Andrews 3001 Winter Park, FL MLS# A11924851
$218,000
2

Beds

1.1

Baths

1,085

Sq.Ft.

200 Saint Andrews 3001

Winter Park, FL

Courtesy of KLEROS REALTY
View 1695 LEE ROAD C202 Winter Park, FL MLS# O6285607
$210,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD C202

Winter Park, FL

Courtesy of PRIMESTATE REALTY, INC.
View 851 MILES AVENUE 13 Winter Park, FL MLS# O6368234
  • Virtual Tour
1 of 24
OPEN HOUSE: Saturday 4/18 1:00 PM - 3:00 PM
$209,999
2

Beds

1.0

Baths

808

Sq.Ft.

851 MILES AVENUE 13

Winter Park, FL

Courtesy of LPT 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 3038 ANTIQUE OAKS CIRCLE 166 Winter Park, FL MLS# O6156853
$205,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

3038 ANTIQUE OAKS CIRCLE 166

Winter Park, FL

Courtesy of YOUNG REAL ESTATE
View 4864 TANGERINE AVENUE 4864 Winter Park, FL MLS# O6383320
$200,000
2

Beds

2.0

Baths

1,059

Sq.Ft.

4864 TANGERINE AVENUE 4864

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY

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

355

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 22
$300K - 400K 18
$400K - 500K 29
$500K - 600K 19
$600K - 700K 23
$700K - 800K 14
$800K - 900K 13
$900K - 1M 10
$1M - Max 153

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 215
Townhouse 14
Condo 89
Commercial 3
Rental 91
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 4/16/2026)

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 4/16/2026.

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 4/16/2026.

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 4/16/2026.