39 total properties
Did you mean the neighborhood Winter Springs?
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 600 NORTHERN WAY 302 Winter Springs, FL MLS# O6396912
$269,900
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 302

Winter Springs, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 702 GLASGOW COURT Winter Springs, FL MLS# O6394959
  • Virtual Tour
1 of 33
$313,700
4

Beds

2.1

Baths

1,878

Sq.Ft.

702 GLASGOW COURT

Winter Springs, FL

Courtesy of SHAWFIELD REALTY GROUP
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 476 CLUB DRIVE Winter Springs, FL MLS# O6392856
  • Virtual Tour
1 of 37
$275,000
3

Beds

2.0

Baths

1,460

Sq.Ft.

476 CLUB DRIVE

Winter Springs, FL

Courtesy of KELLER WILLIAMS HERITAGE REALTY
View 576 PINEBRANCH CIRCLE Winter Springs, FL MLS# O6401477
$340,000
3

Beds

2.1

Baths

1,602

Sq.Ft.

576 PINEBRANCH CIRCLE

Winter Springs, FL

Courtesy of COMPASS FLORIDA LLC
View 712 LINDEN DRIVE Winter Springs, FL MLS# O6388467
  • Virtual Tour
1 of 24
$300,000
3

Beds

2.0

Baths

1,366

Sq.Ft.

712 LINDEN DRIVE

Winter Springs, FL

Courtesy of SHAW SIGNATURE RE
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 421 HORIZON DRIVE Winter Springs, FL MLS# O6384932
  • Virtual Tour
1 of 29
$294,900
3

Beds

2.0

Baths

1,069

Sq.Ft.

421 HORIZON DRIVE

Winter Springs, FL

Courtesy of REAL BROKER, LLC
View 600 NORTHERN WAY 1608 Winter Springs, FL MLS# G5108558
$272,000
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 1608

Winter Springs, FL

View 446 CLUB DRIVE Winter Springs, FL MLS# O6380694
  • Virtual Tour
1 of 40
$269,000
3

Beds

2.0

Baths

1,460

Sq.Ft.

446 CLUB DRIVE

Winter Springs, FL

Courtesy of COLDWELL BANKER REALTY
View 600 NORTHERN WAY 201 Winter Springs, FL MLS# O6381688
$289,900
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 201

Winter Springs, FL

Courtesy of EXP REALTY LLC
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 600 NORTHERN WAY 906 Winter Springs, FL MLS# O6375918
$290,000
3

Beds

3.0

Baths

1,609

Sq.Ft.

600 NORTHERN WAY 906

Winter Springs, FL

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 140 N. FAIRFAX Winter Springs, FL MLS# O6364352
  • Virtual Tour
1 of 42
$325,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

140 N. FAIRFAX

Winter Springs, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 314 SAN GABRIEL STREET Winter Springs, FL MLS# O6350799
$279,990
3

Beds

2.0

Baths

1,091

Sq.Ft.

314 SAN GABRIEL STREET

Winter Springs, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 1053 W PEBBLE BEACH CIRCLE Winter Springs, FL MLS# O6314126
$309,777
3

Beds

2.0

Baths

1,574

Sq.Ft.

1053 W PEBBLE BEACH CIRCLE

Winter Springs, FL

Courtesy of INT'L PROFESSIONAL REALTY INC

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

229

Estimated median home price

$430,000
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 54
$500K - 600K 22
$600K - 700K 16
$700K - 800K 19
$800K - 900K 9
$900K - 1M 3
$1M - Max 10

Homes for Sale by Type in Winter Springs, FL

Property Type Count
Single Family 150
Townhouse 54
Condo 17
Commercial 4
Rental 40
Lots and Land 2
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 7/6/2026)

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 7/6/2026.