181 total properties
Did you mean the neighborhood Winter Park?
View 675 OVERSPIN DRIVE Winter Park, FL MLS# O6378975
$800,000
4

Beds

3.1

Baths

3,062

Sq.Ft.

675 OVERSPIN DRIVE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
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1 of 17
$195,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

Courtesy of TRANSCEND REALTY
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
$644,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2748 LION HEART ROAD Winter Park, FL MLS# O6379237
$500,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

2748 LION HEART ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 4872 ORANGE AVENUE Winter Park, FL MLS# O6380333
$375,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

4872 ORANGE AVENUE

Winter Park, FL

Courtesy of ALFA REAL ESTATE LLC
View 1000 S SEMORAN BOULEVARD 512 Winter Park, FL MLS# O6379459
$128,500
2

Beds

2.0

Baths

1,072

Sq.Ft.

1000 S SEMORAN BOULEVARD 512

Winter Park, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 1564 CAVENDISH ROAD Winter Park, FL MLS# O6380505
$470,000
2

Beds

1.0

Baths

1,140

Sq.Ft.

1564 CAVENDISH ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2600 EUSTON ROAD Winter Park, FL MLS# O6380534
$650,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

Courtesy of YOUNG REAL ESTATE
View 630 SAINT DUNSTAN WAY Winter Park, FL MLS# O6376860
$675,000
5

Beds

2.0

Baths

2,240

Sq.Ft.

630 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
$255,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 229

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378461
$630,000
Studio

Beds

0.0

Baths

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$549,900
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 620 DARCEY DRIVE Winter Park, FL MLS# O6378148
$739,000
4

Beds

2.0

Baths

2,075

Sq.Ft.

620 DARCEY DRIVE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1702 GLENRIDGE WAY Winter Park, FL MLS# A11954444
$789,000
2

Beds

2.0

Baths

1,832

Sq.Ft.

1702 GLENRIDGE WAY

Winter Park, FL

Courtesy of BHHS EWM REALTY
View 841 W SWOOPE AVENUE Winter Park, FL MLS# O6373287
$740,000
2

Beds

1.0

Baths

1,396

Sq.Ft.

841 W SWOOPE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2249 MINNESOTA AVENUE Winter Park, FL MLS# O6377279
$419,990
4

Beds

2.0

Baths

1,536

Sq.Ft.

2249 MINNESOTA AVENUE

Winter Park, FL

Courtesy of MARKET CONNECT REALTY LLC
View 3315 AMBER WOOD WAY 104 Winter Park, FL MLS# O6376997
$165,000
2

Beds

1.1

Baths

990

Sq.Ft.

3315 AMBER WOOD WAY 104

Winter Park, FL

Courtesy of 100% REAL ESTATE, INC
View 2609 SUMMERFIELD ROAD Winter Park, FL MLS# O6377302
$899,000
5

Beds

2.0

Baths

2,554

Sq.Ft.

2609 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
$579,999
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
$499,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

3207 LOWNDES DRIVE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY

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

307

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

PriceCount
$0 - 100K5
$100K - 200K38
$200K - 300K30
$300K - 400K20
$400K - 500K24
$500K - 600K15
$600K - 700K18
$700K - 800K21
$800K - 900K6
$900K - 1M8
$1M - Max122

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family173
Townhouse16
Condo83
Commercial4
Rental75
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 3/4/2026)

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 3/5/2026.

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 3/5/2026.

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 3/5/2026.