40 total properties
Did you mean the neighborhood Winter Park?
View 2919 BOWER ROAD Winter Park, FL MLS# O6391025
  • Recently Listed with Virtual Tour
1 of 38
OPEN HOUSE: Sunday 3/22 1:00 PM - 3:00 PM
$779,000
3

Beds

2.0

Baths

2,325

Sq.Ft.

2919 BOWER ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1760 GREENWICH AVENUE Winter Park, FL MLS# O6392001
  • Recently Listed with Virtual Tour
1 of 18
OPEN HOUSE: Sunday 3/22 12:00 PM - 2:00 PM
$650,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

1760 GREENWICH AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1034 TURNER ROAD Winter Park, FL MLS# O6390132
  • Recently Listed
1 of 5
$724,900
Studio

Beds

0.0

Baths

1034 TURNER ROAD

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 259 E CANTON AVENUE 259 Winter Park, FL MLS# O6389246
  • Recently Listed with Virtual Tour
1 of 36
$649,000
2

Beds

2.0

Baths

1,040

Sq.Ft.

259 E CANTON AVENUE 259

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 218 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6388723
  • Recently Listed with Virtual Tour
1 of 29
$635,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

218 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1926 NATALEN ROAD Winter Park, FL MLS# O6388308
  • Recently Listed with Virtual Tour
1 of 44
OPEN HOUSE: Sunday 3/22 12:00 PM - 4:00 PM
$649,900
3

Beds

2.0

Baths

1,469

Sq.Ft.

1926 NATALEN ROAD

Winter Park, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Recently Listed with Virtual Tour
1 of 39
$599,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Recently Listed with Virtual Tour
1 of 50
$635,000
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 2625 SUMMERFIELD ROAD Winter Park, FL MLS# O6384757
$724,900
5

Beds

3.0

Baths

2,199

Sq.Ft.

2625 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1108 FAIRWAY DRIVE Winter Park, FL MLS# O6386266
$725,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

1108 FAIRWAY DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 643 DUNBLANE DRIVE Winter Park, FL MLS# O6386136
$734,800
3

Beds

2.0

Baths

1,575

Sq.Ft.

643 DUNBLANE DRIVE

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 675 OVERSPIN DRIVE Winter Park, FL MLS# O6378975
$775,000
4

Beds

3.1

Baths

3,062

Sq.Ft.

675 OVERSPIN DRIVE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
$634,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
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 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 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 681 OVERSPIN DRIVE Winter Park, FL MLS# O6376464
$669,000
4

Beds

2.1

Baths

2,220

Sq.Ft.

681 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RE/MAX SELECT GROUP
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6375545
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 352 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6377540
$650,000
5

Beds

3.0

Baths

1,917

Sq.Ft.

352 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1500 BERKSHIRE AVENUE Winter Park, FL MLS# O6374856
$625,000
3

Beds

1.1

Baths

1,485

Sq.Ft.

1500 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of SOTERA LIVING

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

318

Estimated median home price

$737,350
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 - 100K6
$100K - 200K42
$200K - 300K23
$300K - 400K16
$400K - 500K28
$500K - 600K14
$600K - 700K22
$700K - 800K17
$800K - 900K8
$900K - 1M9
$1M - Max133

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family183
Townhouse17
Condo83
Commercial3
Rental87
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 3/18/2026)

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 3/22/2026.

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 3/22/2026.