44 total properties
Did you mean the neighborhood Winter Springs?
View 538 CRIMSON LANE Winter Springs, FL MLS# O6409571
$369,900
3

Beds

3.1

Baths

1,854

Sq.Ft.

538 CRIMSON LANE

Winter Springs, FL

View 1018 WEATHERED WOOD CIRCLE Winter Springs, FL MLS# O6408847
$369,000
3

Beds

2.0

Baths

1,718

Sq.Ft.

1018 WEATHERED WOOD CIRCLE

Winter Springs, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 1385 PONCE DE LEON BOULEVARD Winter Springs, FL MLS# W7887141
$367,000
3

Beds

2.0

Baths

1,460

Sq.Ft.

1385 PONCE DE LEON BOULEVARD

Winter Springs, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 101 S FLAMINGO AVENUE Winter Springs, FL MLS# S5150918
  • Recently Listed
1 of 14
$365,500
3

Beds

2.0

Baths

1,368

Sq.Ft.

101 S FLAMINGO AVENUE

Winter Springs, FL

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 830 DUNBAR TERRACE Winter Springs, FL MLS# O6418603
  • Recently Listed with Virtual Tour
1 of 26
$361,000
3

Beds

2.1

Baths

1,792

Sq.Ft.

830 DUNBAR TERRACE

Winter Springs, FL

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 221 SHERRY AVE Winter Springs, FL MLS# O6404854
  • Virtual Tour
1 of 18
$359,900
4

Beds

2.0

Baths

1,700

Sq.Ft.

221 SHERRY AVE

Winter Springs, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 339 INGLENOOK CIRCLE Winter Springs, FL MLS# O6411718
$359,900
3

Beds

2.0

Baths

1,437

Sq.Ft.

339 INGLENOOK CIRCLE

Winter Springs, FL

View 451 HARBOR WINDS COURT Winter Springs, FL MLS# O6406257
$357,500
3

Beds

2.1

Baths

1,914

Sq.Ft.

451 HARBOR WINDS COURT

Winter Springs, FL

Courtesy of KELLER WILLIAMS HERITAGE 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 108 SUNDANCE COURT Winter Springs, FL MLS# O6409784
$349,900
3

Beds

2.0

Baths

1,161

Sq.Ft.

108 SUNDANCE COURT

Winter Springs, FL

Courtesy of JEMINI REALTY CORP
View 717 WILSON ROAD Winter Springs, FL MLS# O6372938
  • Virtual Tour
1 of 59
$340,000
3

Beds

2.0

Baths

1,368

Sq.Ft.

717 WILSON ROAD

Winter Springs, FL

Courtesy of FLORIDA USA REALTY
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 335 LANSBROOK LANE Winter Springs, FL MLS# O6407329
$335,000
2

Beds

2.0

Baths

1,129

Sq.Ft.

335 LANSBROOK LANE

Winter Springs, FL

View 572 PINEBRANCH CIRCLE Winter Springs, FL MLS# O6397068
  • Virtual Tour
1 of 40
OPEN HOUSE: Sunday 7/12 1:00 PM - 4:00 PM
$330,000
3

Beds

2.1

Baths

1,564

Sq.Ft.

572 PINEBRANCH CIRCLE

Winter Springs, FL

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 116 PHILADELPHIA WAY Winter Springs, FL MLS# O6379053
$325,000
3

Beds

2.1

Baths

1,468

Sq.Ft.

116 PHILADELPHIA WAY

Winter Springs, FL

Courtesy of SUNNY 365 REALTY GROUP
View 471 HARBOR WINDS COURT Winter Springs, FL MLS# O6387316
  • Virtual Tour
1 of 29
OPEN HOUSE: Saturday 7/11 11:00 AM - 1:00 PM
$325,000
3

Beds

2.1

Baths

1,680

Sq.Ft.

471 HARBOR WINDS COURT

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

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

225

Estimated median home price

$425,000
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 10
$200K - 300K 42
$300K - 400K 44
$400K - 500K 52
$500K - 600K 21
$600K - 700K 16
$700K - 800K 18
$800K - 900K 9
$900K - 1M 3
$1M - Max 10

Homes for Sale by Type in Winter Springs, FL

Property Type Count
Single Family 147
Townhouse 53
Condo 17
Commercial 4
Rental 41
Lots and Land 2
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 7/8/2026)

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 7/8/2026.