57 total properties
Did you mean the neighborhood Winter Springs?
View 416 MACGREGOR ROAD Winter Springs, FL MLS# O6379428
$470,000
3

Beds

2.1

Baths

1,962

Sq.Ft.

416 MACGREGOR ROAD

Winter Springs, FL

Courtesy of COMPASS FLORIDA LLC
View 122 STONE GABLE CIR Winter Springs, FL MLS# O6340870
$469,900
3

Beds

2.1

Baths

2,147

Sq.Ft.

122 STONE GABLE CIR

Winter Springs, FL

View 358 BRUSHWOOD LANE Winter Springs, FL MLS# O6412915
$468,000
4

Beds

2.0

Baths

1,922

Sq.Ft.

358 BRUSHWOOD LANE

Winter Springs, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1128 SPOTTED SANDPIPER LOOP Winter Springs, FL MLS# O6395600
$464,000
4

Beds

3.1

Baths

2,344

Sq.Ft.

1128 SPOTTED SANDPIPER LOOP

Winter Springs, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 416 MICHAEL BLAKE BOULEVARD Winter Springs, FL MLS# O6424732
$460,000
3

Beds

2.1

Baths

1,868

Sq.Ft.

416 MICHAEL BLAKE BOULEVARD

Winter Springs, FL

View 877 BENCHWOOD DRIVE Winter Springs, FL MLS# O6410431
$450,000
3

Beds

2.0

Baths

1,612

Sq.Ft.

877 BENCHWOOD DRIVE

Winter Springs, FL

Courtesy of COMPASS FLORIDA LLC
View 1153 SPOTTED SANDPIPER LOOP Winter Springs, FL MLS# O6419082
  • Recently Listed with Virtual Tour
1 of 23
$450,000
3

Beds

2.1

Baths

1,768

Sq.Ft.

1153 SPOTTED SANDPIPER LOOP

Winter Springs, FL

View 930 OAK FOREST DRIVE Winter Springs, FL MLS# O6423576
  • Recently Listed with Virtual Tour
1 of 30
$450,000
4

Beds

2.0

Baths

1,764

Sq.Ft.

930 OAK FOREST DRIVE

Winter Springs, FL

Courtesy of MARK SPAIN REAL ESTATE
View 1050 NURSERY ROAD Winter Springs, FL MLS# O6376787
$449,900
13,000

Sq.Ft.

1050 NURSERY ROAD

Winter Springs, FL

View 1530 BRAEWICK STREET Winter Springs, FL MLS# TB8518340
$449,900
3

Beds

2.0

Baths

1,889

Sq.Ft.

1530 BRAEWICK STREET

Winter Springs, FL

View 161 BEAR SPRINGS DRIVE Winter Springs, FL MLS# O6386458
  • New Construction
1 of 35
$444,990
3

Beds

2.1

Baths

1,704

Sq.Ft.

161 BEAR SPRINGS DRIVE

Winter Springs, FL

View 189 BEAR SPRINGS DRIVE Winter Springs, FL MLS# O6372546
  • New Construction
1 of 33
$443,990
3

Beds

2.1

Baths

1,704

Sq.Ft.

189 BEAR SPRINGS DRIVE

Winter Springs, FL

View 173 BEAR SPRINGS DRIVE Winter Springs, FL MLS# O6386437
  • New Construction
1 of 35
$439,990
3

Beds

2.1

Baths

1,704

Sq.Ft.

173 BEAR SPRINGS DRIVE

Winter Springs, FL

View 1375 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL MLS# O6424446
$435,900
3

Beds

2.1

Baths

2,063

Sq.Ft.

1375 AUGUSTA NATIONAL BOULEVARD

Winter Springs, FL

View 661 ANDOVER CIRCLE Winter Springs, FL MLS# O6417072
$435,000
3

Beds

2.0

Baths

1,735

Sq.Ft.

661 ANDOVER CIRCLE

Winter Springs, FL

View 717 ADIDAS ROAD Winter Springs, FL MLS# V4949727
  • Virtual Tour
1 of 31
$434,900
2

Beds

2.0

Baths

1,812

Sq.Ft.

717 ADIDAS ROAD

Winter Springs, FL

Courtesy of COLDWELL BANKER REALTY
View 1307 ORTEGA STREET Winter Springs, FL MLS# O6391915
$430,000
3

Beds

2.0

Baths

1,881

Sq.Ft.

1307 ORTEGA STREET

Winter Springs, FL

Courtesy of CENTURY 21 ALTON CLARK
View 963 SEQUOIA DRIVE Winter Springs, FL MLS# O6424067
  • Recently Listed with Virtual Tour
1 of 28
$430,000
3

Beds

2.0

Baths

1,831

Sq.Ft.

963 SEQUOIA DRIVE

Winter Springs, FL

View 1422 SPALDING ROAD Winter Springs, FL MLS# O6313691
$425,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

1422 SPALDING ROAD

Winter Springs, FL

View 560 PLEASANT GROVE DRIVE Winter Springs, FL MLS# O6401016
$425,000
3

Beds

2.0

Baths

1,654

Sq.Ft.

560 PLEASANT GROVE DRIVE

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III

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 37
$400K - 500K 45
$500K - 600K 12
$600K - 700K 9
$700K - 800K 13
$800K - 900K 3
$900K - 1M 2
$1M - Max 9

Homes for Sale by Type in Winter Springs, FL

Property Type Count
Single Family 108
Townhouse 42
Condo 14
Commercial 3
Rental 39
Lots and Land 2
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 7/15/2026)

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 7/16/2026.