28 total properties
Did you mean the neighborhood Winter Springs?
View 201 BENNETT STREET Winter Springs, FL MLS# R4909500
$299,000
4

Beds

2.1

Baths

1,405

Sq.Ft.

201 BENNETT STREET

Winter Springs, FL

Courtesy of NORTHAM REALTY, LLC
View Address not provided Winter Springs, FL MLS# O6345021
$299,000
3

Beds

2.0

Baths

1,192

Sq.Ft.

Address not provided

Winter Springs, FL

Courtesy of CORCORAN PREMIER REALTY
View 421 TRADITION LANE Winter Springs, FL MLS# S5132445
$294,900
2

Beds

2.1

Baths

1,275

Sq.Ft.

421 TRADITION LANE

Winter Springs, FL

Courtesy of THE REALTY COLLECTION
The time to sell is now! THE TIME TO SELL IS NOW!
View 718 LAKESIDE DRIVE Winter Springs, FL MLS# O6329734
$289,000
2

Beds

2.0

Baths

1,166

Sq.Ft.

718 LAKESIDE DRIVE

Winter Springs, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 314 SAN GABRIEL STREET Winter Springs, FL MLS# O6350799
  • Virtual Tour
1 of 30
OPEN HOUSE: Sunday 12/14 1:00 PM - 4:00 PM
$285,990
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 4004 GARDEN OAK COURT Winter Springs, FL MLS# O6351613
$285,000
2

Beds

2.1

Baths

1,306

Sq.Ft.

4004 GARDEN OAK COURT

Winter Springs, FL

Courtesy of RE/MAX INNOVATION
View 600 NORTHERN WAY #502 Winter Springs, FL MLS# O6286935
$284,900
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY #502

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 270 SAN GABRIEL STREET Winter Springs, FL MLS# O6359666
$279,900
3

Beds

2.0

Baths

1,089

Sq.Ft.

270 SAN GABRIEL STREET

Winter Springs, FL

Courtesy of MAINFRAME REAL ESTATE
View 1340 DELANEY DRIVE Winter Springs, FL MLS# O6346776
$272,500
3

Beds

2.0

Baths

1,422

Sq.Ft.

1340 DELANEY DRIVE

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 498 CLUB DRIVE Winter Springs, FL MLS# O6332792
$250,000
2

Beds

2.0

Baths

1,224

Sq.Ft.

498 CLUB DRIVE

Winter Springs, FL

Courtesy of PAINE-ANDERSON PROPERTIES, INC
View 294 SAN GABRIEL STREET Winter Springs, FL MLS# O6293769
$245,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

294 SAN GABRIEL STREET

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 429 SHEOAH BOULEVARD #8 Winter Springs, FL MLS# S5139927
  • Recently Listed with Virtual Tour
1 of 17
$245,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

429 SHEOAH BOULEVARD #8

Winter Springs, FL

Courtesy of UPZEL REALTY LLC
View 1355 CASA PARK CIRCLE Winter Springs, FL MLS# O6356067
$239,000
2

Beds

2.1

Baths

1,156

Sq.Ft.

1355 CASA PARK CIRCLE

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 506 CLUB DRIVE Winter Springs, FL MLS# O6362326
  • Recently Listed with Virtual Tour
1 of 33
$239,000
2

Beds

2.0

Baths

1,002

Sq.Ft.

506 CLUB DRIVE

Winter Springs, FL

Courtesy of CALL IT CLOSED INTL REALTY
View 326 SAN MIGUEL STREET Winter Springs, FL MLS# O6352626
$234,000
3

Beds

2.0

Baths

1,032

Sq.Ft.

326 SAN MIGUEL STREET

Winter Springs, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 411 GREEN SPRING CIRCLE Winter Springs, FL MLS# O6339004
$232,000
3

Beds

1.1

Baths

1,130

Sq.Ft.

411 GREEN SPRING CIRCLE

Winter Springs, FL

Courtesy of WATSON REALTY CORP
View 434TH Winter Springs, FL MLS# S5100991
$229,000
Studio

Beds

0.0

Baths

434TH

Winter Springs, FL

Courtesy of EMPIRE REALTY & MANAGEMENT SERVICES
View 505 MOREE LOOP Winter Springs, FL MLS# V4944893
$225,000
2

Beds

2.1

Baths

1,434

Sq.Ft.

505 MOREE LOOP

Winter Springs, FL

Courtesy of LPT REALTY LLC
View 30 MOREE LOOP #39 Winter Springs, FL MLS# O6333905
$210,000
3

Beds

2.1

Baths

1,400

Sq.Ft.

30 MOREE LOOP #39

Winter Springs, FL

Courtesy of PARK VIEW REALTY INC
View 90 MOREE LOOP #15 Winter Springs, FL MLS# O6336580
$199,900
3

Beds

2.0

Baths

1,187

Sq.Ft.

90 MOREE LOOP #15

Winter Springs, FL

Courtesy of FLORIDA REALTY INVESTMENTS

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

177

Estimated median home price

$430,990
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 - 100K2
$100K - 200K7
$200K - 300K19
$300K - 400K49
$400K - 500K42
$500K - 600K16
$600K - 700K14
$700K - 800K16
$800K - 900K2
$900K - 1M2
$1M - Max8

Homes for Sale by Type in Winter Springs, FL

Property TypeCount
Single Family116
Townhouse38
Condo10
Commercial2
Rental54
Lots and Land7
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home2
Farms0

(Data as of 12/9/2025)

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 12/9/2025.