152 total properties
Did you mean the neighborhood Winter Springs?
View 161 BEAR SPRINGS DRIVE Winter Springs, FL MLS# O6386458
  • New Construction
1 of 35
OPEN HOUSE: Sunday 5/17 12:00 PM - 5:00 PM
$484,990
3

Beds

2.1

Baths

1,704

Sq.Ft.

161 BEAR SPRINGS DRIVE

Winter Springs, FL

Courtesy of MATTAMY REAL ESTATE SERVICES
View 1262 SPOTTED SANDPIPER LOOP Winter Springs, FL MLS# O6380617
  • Virtual Tour
1 of 63
OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
$479,999
4

Beds

3.1

Baths

2,353

Sq.Ft.

1262 SPOTTED SANDPIPER LOOP

Winter Springs, FL

Courtesy of ROI AVE LLC
View 1716 FOX GLEN COURT Winter Springs, FL MLS# O6362670
$479,000
3

Beds

2.0

Baths

1,889

Sq.Ft.

1716 FOX GLEN COURT

Winter Springs, FL

Courtesy of RED CARPET REALTY FLORIDA
The time to sell is now! THE TIME TO SELL IS NOW!
View 629 RYAN COURT Winter Springs, FL MLS# O6396980
  • Recently Listed with Virtual Tour
1 of 33
$479,000
3

Beds

2.0

Baths

1,857

Sq.Ft.

629 RYAN COURT

Winter Springs, FL

Courtesy of SOTERA LIVING
View 1128 SPOTTED SANDPIPER LOOP Winter Springs, FL MLS# O6395600
$478,500
4

Beds

3.1

Baths

2,344

Sq.Ft.

1128 SPOTTED SANDPIPER LOOP

Winter Springs, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1452 CONNORS LANE Winter Springs, FL MLS# O6404505
$475,000
3

Beds

2.0

Baths

1,766

Sq.Ft.

1452 CONNORS LANE

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
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 1126 TROTWOOD BOULEVARD Winter Springs, FL MLS# O6382859
$470,000
4

Beds

2.0

Baths

2,066

Sq.Ft.

1126 TROTWOOD BOULEVARD

Winter Springs, FL

Courtesy of JOY ESTATE ENTERPRISE INC
View 104 REDTAIL PLACE Winter Springs, FL MLS# O6378697
  • Virtual Tour
1 of 45
$469,900
3

Beds

2.0

Baths

1,766

Sq.Ft.

104 REDTAIL PLACE

Winter Springs, FL

Courtesy of JASON MITCHELL REAL ESTATE FLO
View 903 TORREY PINE DRIVE Winter Springs, FL MLS# O6377459
$469,900
3

Beds

2.0

Baths

1,501

Sq.Ft.

903 TORREY PINE DRIVE

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 859 BENCHWOOD DRIVE Winter Springs, FL MLS# O6397781
$454,900
4

Beds

2.0

Baths

1,632

Sq.Ft.

859 BENCHWOOD DRIVE

Winter Springs, FL

Courtesy of VALENCE REALTY GROUP
View 431 S HAWTHORN CIRCLE Winter Springs, FL MLS# O6330022
$450,000
5

Beds

2.1

Baths

2,092

Sq.Ft.

431 S HAWTHORN CIRCLE

Winter Springs, FL

Courtesy of THE SHUGAN GROUP INC
View 1059 CEDAR BAY Winter Springs, FL MLS# O6382674
  • Virtual Tour
1 of 49
$450,000
4

Beds

3.1

Baths

2,225

Sq.Ft.

1059 CEDAR BAY

Winter Springs, FL

Courtesy of WATSON REALTY CORP
View 1331 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL MLS# O6389425
$450,000
3

Beds

2.0

Baths

1,657

Sq.Ft.

1331 AUGUSTA NATIONAL BOULEVARD

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 632 TUSKAWILLA POINT LANE Winter Springs, FL MLS# O6394544
$450,000
4

Beds

2.0

Baths

1,917

Sq.Ft.

632 TUSKAWILLA POINT LANE

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY
View 758 N GRETNA COURT Winter Springs, FL MLS# O6404912
  • Recently Listed with Virtual Tour
1 of 58
$450,000
4

Beds

3.0

Baths

2,150

Sq.Ft.

758 N GRETNA COURT

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 1327 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL MLS# O6399111
$448,000
3

Beds

2.0

Baths

2,128

Sq.Ft.

1327 AUGUSTA NATIONAL BOULEVARD

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 788 ANDOVER CIRCLE Winter Springs, FL MLS# O6397299
$445,000
3

Beds

2.0

Baths

1,791

Sq.Ft.

788 ANDOVER CIRCLE

Winter Springs, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 560 PLEASANT GROVE DRIVE Winter Springs, FL MLS# O6401016
  • Recently Listed with Virtual Tour
1 of 23
OPEN HOUSE: Sunday 5/17 11:00 AM - 2:00 PM
$445,000
3

Beds

2.0

Baths

1,654

Sq.Ft.

560 PLEASANT GROVE DRIVE

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 1024 DINERO DRIVE Winter Springs, FL MLS# O6404240
  • Recently Listed with Virtual Tour
1 of 38
$444,500
3

Beds

2.0

Baths

1,463

Sq.Ft.

1024 DINERO DRIVE

Winter Springs, FL

Courtesy of CALL IT CLOSED INTL 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

224

Estimated median home price

$444,750
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 34
$300K - 400K 52
$400K - 500K 50
$500K - 600K 21
$600K - 700K 17
$700K - 800K 16
$800K - 900K 9
$900K - 1M 4
$1M - Max 11

Homes for Sale by Type in Winter Springs, FL

Property Type Count
Single Family 148
Townhouse 53
Condo 16
Commercial 3
Rental 35
Lots and Land 2
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 5/16/2026)

Information deemed reliable but not guaranteed.

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All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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 5/16/2026.

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 5/16/2026.