176 total properties
Did you mean the neighborhood Winter Springs?
View 337 KIRKCALDY DRIVE Winter Springs, FL MLS# O6375532
$287,900
2

Beds

2.0

Baths

974

Sq.Ft.

337 KIRKCALDY DRIVE

Winter Springs, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 206 CHARLES STREET Winter Springs, FL MLS# O6377966
$285,000
4

Beds

1.0

Baths

1,120

Sq.Ft.

206 CHARLES STREET

Winter Springs, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 600 NORTHERN WAY 201 Winter Springs, FL MLS# O6381688
  • Recently Listed with Virtual Tour
1 of 42
$285,000
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 201

Winter Springs, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3825 BLACK SPRUCE LANE Winter Springs, FL MLS# O6372860
$280,000
2

Beds

2.1

Baths

1,306

Sq.Ft.

3825 BLACK SPRUCE LANE

Winter Springs, FL

Courtesy of ABSOLUTE REALTY GROUP, LLC
View 600 NORTHERN WAY 1608 Winter Springs, FL MLS# G5108558
  • Recently Listed with Virtual Tour
1 of 24
$280,000
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 1608

Winter Springs, FL

Courtesy of WORTH CLARK REALTY
View 600 NORTHERN WAY 502 Winter Springs, FL MLS# O6286935
$279,999
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 502

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 314 SAN GABRIEL STREET Winter Springs, FL MLS# O6350799
  • Virtual Tour
1 of 30
OPEN HOUSE: Saturday 3/7 12:00 PM - 3:00 PM
$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 446 CLUB DRIVE Winter Springs, FL MLS# O6380694
  • Recently Listed with Virtual Tour
1 of 40
$279,900
3

Beds

2.0

Baths

1,460

Sq.Ft.

446 CLUB DRIVE

Winter Springs, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 51 N CORTEZ AVENUE Winter Springs, FL MLS# V4946830
$275,000
2

Beds

1.0

Baths

912

Sq.Ft.

51 N CORTEZ AVENUE

Winter Springs, FL

Courtesy of PRIME REAL ESTATE, INC.
View 270 SAN GABRIEL STREET Winter Springs, FL MLS# O6359666
$274,900
3

Beds

2.0

Baths

1,089

Sq.Ft.

270 SAN GABRIEL STREET

Winter Springs, FL

Courtesy of MAINFRAME REAL ESTATE
View 606 CASA PARK A COURT Winter Springs, FL MLS# O6376778
$274,900
2

Beds

2.1

Baths

1,156

Sq.Ft.

606 CASA PARK A COURT

Winter Springs, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
View 552 SHADOW GLENN PLACE Winter Springs, FL MLS# O6382972
  • Recently Listed with Virtual Tour
1 of 33
$269,900
2

Beds

2.1

Baths

1,359

Sq.Ft.

552 SHADOW GLENN PLACE

Winter Springs, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 4467 BROOK HOLLOW CIRCLE Winter Springs, FL MLS# S5143752
  • Recently Listed with Virtual Tour
1 of 28
$268,990
3

Beds

2.1

Baths

1,344

Sq.Ft.

4467 BROOK HOLLOW CIRCLE

Winter Springs, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 1340 DELANEY DRIVE Winter Springs, FL MLS# O6346776
$265,000
3

Beds

2.0

Baths

1,422

Sq.Ft.

1340 DELANEY DRIVE

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 1305 PARK VILLA PLACE Winter Springs, FL MLS# O6381179
  • Recently Listed with Virtual Tour
1 of 10
$256,000
2

Beds

1.1

Baths

1,156

Sq.Ft.

1305 PARK VILLA PLACE

Winter Springs, FL

Courtesy of KELLER WILLIAMS HERITAGE REALTY
View 4431 BROOK HOLLOW CIRCLE Winter Springs, FL MLS# O6374194
$250,000
3

Beds

2.0

Baths

1,367

Sq.Ft.

4431 BROOK HOLLOW CIRCLE

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 565 GREEN SPRING CIRCLE Winter Springs, FL MLS# O6384281
  • Recently Listed with Virtual Tour
1 of 37
$249,900
2

Beds

1.1

Baths

1,363

Sq.Ft.

565 GREEN SPRING CIRCLE

Winter Springs, FL

Courtesy of COLDWELL BANKER REALTY
View 604 CASA PARK A COURT Winter Springs, FL MLS# O6381106
  • Recently Listed with Virtual Tour
1 of 26
$247,000
2

Beds

2.1

Baths

1,156

Sq.Ft.

604 CASA PARK A COURT

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 603 CASA PARK COURT C Winter Springs, FL MLS# O6380605
$246,000
2

Beds

2.1

Baths

1,156

Sq.Ft.

603 CASA PARK COURT C

Winter Springs, FL

Courtesy of CALL IT CLOSED INTL REALTY
View 429 SHEOAH BOULEVARD 8 Winter Springs, FL MLS# S5139927
$245,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

429 SHEOAH BOULEVARD 8

Winter Springs, FL

Courtesy of UPZEL REALTY LLC

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

209

Estimated median home price

$424,990
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 - 100K1
$100K - 200K5
$200K - 300K35
$300K - 400K56
$400K - 500K52
$500K - 600K16
$600K - 700K11
$700K - 800K17
$800K - 900K5
$900K - 1M5
$1M - Max6

Homes for Sale by Type in Winter Springs, FL

Property TypeCount
Single Family136
Townhouse52
Condo13
Commercial1
Rental38
Lots and Land5
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home1
Farms0

(Data as of 3/3/2026)

Information deemed reliable but not guaranteed.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

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 3/3/2026.

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 3/3/2026.