27 total properties
Did you mean the neighborhood Winter Springs?
View 116 PHILADELPHIA WAY Winter Springs, FL MLS# O6379053
$304,900
3

Beds

2.1

Baths

1,468

Sq.Ft.

116 PHILADELPHIA WAY

Winter Springs, FL

View 702 GLASGOW COURT Winter Springs, FL MLS# O6394959
$301,000
4

Beds

2.1

Baths

1,878

Sq.Ft.

702 GLASGOW COURT

Winter Springs, FL

View 65 S DEVON AVENUE Winter Springs, FL MLS# O6404319
$300,000
3

Beds

2.0

Baths

1,075

Sq.Ft.

65 S DEVON AVENUE

Winter Springs, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 600 NORTHERN WAY 1804 Winter Springs, FL MLS# O6402233
$299,900
4

Beds

2.1

Baths

1,726

Sq.Ft.

600 NORTHERN WAY 1804

Winter Springs, FL

Courtesy of BHHS FLORIDA REALTY
View 162 CONSTITUTION WAY Winter Springs, FL MLS# O6424530
  • Recently Listed with Virtual Tour
1 of 75
$299,900
3

Beds

2.1

Baths

1,468

Sq.Ft.

162 CONSTITUTION WAY

Winter Springs, FL

View 207 BIRCH TERRACE Winter Springs, FL MLS# O6411799
$297,000
3

Beds

2.0

Baths

1,318

Sq.Ft.

207 BIRCH TERRACE

Winter Springs, FL

View 1393 SAN DIEGO COURT Winter Springs, FL MLS# O6425967
  • Recently Listed with Virtual Tour
1 of 17
$296,000
2

Beds

2.0

Baths

987

Sq.Ft.

1393 SAN DIEGO COURT

Winter Springs, FL

View 421 HORIZON DRIVE Winter Springs, FL MLS# O6384932
$294,900
3

Beds

2.0

Baths

1,069

Sq.Ft.

421 HORIZON DRIVE

Winter Springs, FL

Courtesy of REAL BROKER, LLC
View 299 WOODGREEN LANE Winter Springs, FL MLS# O6401276
$283,500
3

Beds

2.1

Baths

1,326

Sq.Ft.

299 WOODGREEN LANE

Winter Springs, FL

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 600 NORTHERN WAY 201 Winter Springs, FL MLS# O6381688
$279,900
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 201

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 276 SAN GABRIEL STREET Winter Springs, FL MLS# O6399623
$279,000
3

Beds

2.0

Baths

1,089

Sq.Ft.

276 SAN GABRIEL STREET

Winter Springs, FL

View 476 CLUB DRIVE Winter Springs, FL MLS# O6392856
$275,000
3

Beds

2.0

Baths

1,460

Sq.Ft.

476 CLUB DRIVE

Winter Springs, FL

Courtesy of KELLER WILLIAMS HERITAGE REALTY
View 4113 HEDGE MAPLE PLACE Winter Springs, FL MLS# O6396927
$274,200
2

Beds

2.1

Baths

1,330

Sq.Ft.

4113 HEDGE MAPLE PLACE

Winter Springs, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
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
$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 502 Winter Springs, FL MLS# O6286935
$249,900
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 502

Winter Springs, FL

View 270 SAN GABRIEL STREET Winter Springs, FL MLS# O6359666
$249,900
3

Beds

2.0

Baths

1,089

Sq.Ft.

270 SAN GABRIEL STREET

Winter Springs, FL

View 498 GREEN SPRING CIR Winter Springs, FL MLS# O6418425
$249,000
2

Beds

1.1

Baths

1,363

Sq.Ft.

498 GREEN SPRING CIR

Winter Springs, FL

View 605 CASA PARK COURT H Winter Springs, FL MLS# O6390474
  • Recently Listed with Virtual Tour
1 of 24
$245,000
2

Beds

2.1

Baths

1,156

Sq.Ft.

605 CASA PARK COURT H

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

166

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

PriceCount
$0 - 100K0
$100K - 200K7
$200K - 300K30
$300K - 400K34
$400K - 500K47
$500K - 600K13
$600K - 700K6
$700K - 800K13
$800K - 900K6
$900K - 1M2
$1M - Max8

Homes for Sale by Type in Winter Springs, FL

Property TypeCount
Single Family113
Townhouse35
Condo12
Commercial3
Rental40
Lots and Land2
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 7/19/2026)

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 7/19/2026.