38 total properties
Did you mean the neighborhood Winter Springs?
View 221 SHERRY AVE Winter Springs, FL MLS# O6404854
  • Virtual Tour
1 of 18
$354,900
4

Beds

2.0

Baths

1,700

Sq.Ft.

221 SHERRY AVE

Winter Springs, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 335 KIRKCALDY DRIVE Winter Springs, FL MLS# O6400818
$329,900
3

Beds

2.0

Baths

1,178

Sq.Ft.

335 KIRKCALDY DRIVE

Winter Springs, FL

View 1024 DINERO DRIVE Winter Springs, FL MLS# O6404240
  • Virtual Tour
1 of 36
$419,000
3

Beds

2.0

Baths

1,463

Sq.Ft.

1024 DINERO DRIVE

Winter Springs, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1384 MILL STREAM LANE Winter Springs, FL MLS# TB8504740
$382,400
3

Beds

3.1

Baths

1,932

Sq.Ft.

1384 MILL STREAM LANE

Winter Springs, FL

Courtesy of TAH FLORIDA LLC
View 807 BUCKIE DRIVE Winter Springs, FL MLS# O6386108
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1 of 25
$375,000
3

Beds

2.0

Baths

1,574

Sq.Ft.

807 BUCKIE DRIVE

Winter Springs, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
View 572 PINEBRANCH CIRCLE Winter Springs, FL MLS# O6397068
$330,000
3

Beds

2.1

Baths

1,564

Sq.Ft.

572 PINEBRANCH CIRCLE

Winter Springs, FL

View 239 PANORAMA DRIVE Winter Springs, FL MLS# O6397776
$340,000
3

Beds

2.0

Baths

1,349

Sq.Ft.

239 PANORAMA DRIVE

Winter Springs, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 171 CONSTITUTION WAY Winter Springs, FL MLS# O6396871
$315,000
3

Beds

2.1

Baths

1,468

Sq.Ft.

171 CONSTITUTION WAY

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 448 MACGREGOR ROAD Winter Springs, FL MLS# O6397231
$350,000
2

Beds

2.0

Baths

1,477

Sq.Ft.

448 MACGREGOR ROAD

Winter Springs, FL

View 1385 SAN DIEGO COURT Winter Springs, FL MLS# O6397680
$320,000
2

Beds

2.0

Baths

1,518

Sq.Ft.

1385 SAN DIEGO COURT

Winter Springs, FL

Courtesy of COLDWELL BANKER REALTY
View 710 BRIARWOOD DRIVE Winter Springs, FL MLS# O6396343
$360,000
4

Beds

2.0

Baths

1,769

Sq.Ft.

710 BRIARWOOD DRIVE

Winter Springs, FL

View 130 DEER SONG DRIVE Winter Springs, FL MLS# O6395309
$310,000
3

Beds

2.0

Baths

1,105

Sq.Ft.

130 DEER SONG DRIVE

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 1411 BORG LANE Winter Springs, FL MLS# O6378665
$385,000
3

Beds

2.0

Baths

1,368

Sq.Ft.

1411 BORG LANE

Winter Springs, FL

View 622 ANHINGA ROAD Winter Springs, FL MLS# O6369225
  • Virtual Tour
1 of 73
$374,900
3

Beds

2.1

Baths

1,721

Sq.Ft.

622 ANHINGA ROAD

Winter Springs, FL

View 709 SAILFISH ROAD Winter Springs, FL MLS# O6364715
  • Virtual Tour
1 of 28
$402,500
3

Beds

2.0

Baths

1,737

Sq.Ft.

709 SAILFISH ROAD

Winter Springs, FL

View 140 N. FAIRFAX Winter Springs, FL MLS# O6364352
  • Virtual Tour
1 of 42
$315,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

140 N. FAIRFAX

Winter Springs, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 113 LIDO ROAD Winter Springs, FL MLS# O6326611
  • Virtual Tour
1 of 18
$365,000
4

Beds

2.0

Baths

1,312

Sq.Ft.

113 LIDO ROAD

Winter Springs, FL

Courtesy of HD REALTY LLC
View 724 BARRINGTON CIRCLE Winter Springs, FL MLS# O6312092
$399,900
3

Beds

2.0

Baths

1,450

Sq.Ft.

724 BARRINGTON CIRCLE

Winter Springs, FL

About Winter Springs

Distinguished as one of the county's newer communities, Winter Springs is also the largest in terms of land area.  The community once called the Village of North Orlando has seen phenomenal growth over recent decades, experiencing an 800 percent increase in population from 1970 to 2000.  The influx of new businesses, commercial activity, and industrial development is heralding another milestone in the evolution of Winter Springs. The area is quickly transforming from a bedroom community into a highly integrated and well-balanced city.  Winter Springs serves as the host municipality for the country club community of Tuscawilla, recognized as one of the most expansive residential villages northeast of Orlando.  With approximately 12,000 residents, Tuscawilla represents nearly one-third of the total population of Winter Springs.  The community had its genesis in the early 1970s, steadily adding one subdivision after another.  More than 20 of these subdivisions now provide an attractive selection of housing in every price range and architectural style, each one managed by its own homeowners' association.

Listings in Winter Springs, FL

169

Estimated median home price

$424,997
Winter Springs FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Springs, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Springs, FL.

Homes for Sale by Price in Winter Springs, FL

Price Count
$0 - 100K 0
$100K - 200K 8
$200K - 300K 31
$300K - 400K 36
$400K - 500K 46
$500K - 600K 12
$600K - 700K 8
$700K - 800K 13
$800K - 900K 4
$900K - 1M 2
$1M - Max 9

Homes for Sale by Type in Winter Springs, FL

Property Type Count
Single Family 107
Townhouse 42
Condo 14
Commercial 3
Rental 38
Lots and Land 2
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 7/16/2026)

Information deemed reliable but not guaranteed.

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 7/17/2026.