28 total properties
Did you mean the neighborhood Winter Springs?
View 429 SHEOAH BOULEVARD 12 Winter Springs, FL MLS# O6386330
  • Recently Listed with Virtual Tour
1 of 28
$229,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

429 SHEOAH BOULEVARD 12

Winter Springs, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 600 NORTHERN WAY 1608 Winter Springs, FL MLS# G5108558
$280,000
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 1608

Winter Springs, FL

Courtesy of WORTH CLARK REALTY
View 565 GREEN SPRING CIRCLE Winter Springs, FL MLS# O6384281
  • Recently Listed with Virtual Tour
1 of 38
$249,900
2

Beds

1.1

Baths

1,363

Sq.Ft.

565 GREEN SPRING CIRCLE

Winter Springs, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 604 CASA PARK A COURT Winter Springs, FL MLS# O6381106
$239,000
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 552 SHADOW GLENN PLACE Winter Springs, FL MLS# O6382972
$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
  • Virtual Tour
1 of 28
OPEN HOUSE: Sunday 3/15 12:30 PM - 4:00 PM
$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 1305 PARK VILLA PLACE Winter Springs, FL MLS# O6381179
$249,900
2

Beds

1.1

Baths

1,156

Sq.Ft.

1305 PARK VILLA PLACE

Winter Springs, FL

Courtesy of KELLER WILLIAMS HERITAGE REALTY
View 446 CLUB DRIVE Winter Springs, FL MLS# O6380694
$279,900
3

Beds

2.0

Baths

1,460

Sq.Ft.

446 CLUB DRIVE

Winter Springs, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 600 NORTHERN WAY 201 Winter Springs, FL MLS# O6381688
$285,000
3

Beds

2.0

Baths

1,425

Sq.Ft.

600 NORTHERN WAY 201

Winter Springs, FL

Courtesy of EXP REALTY LLC
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 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 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 328 SAN MIGUEL STREET 328 Winter Springs, FL MLS# O6375171
$237,000
3

Beds

2.0

Baths

1,032

Sq.Ft.

328 SAN MIGUEL STREET 328

Winter Springs, FL

Courtesy of REALTY TECH INC
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 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 4431 BROOK HOLLOW CIRCLE Winter Springs, FL MLS# O6374194
$240,000
3

Beds

2.0

Baths

1,367

Sq.Ft.

4431 BROOK HOLLOW CIRCLE

Winter Springs, FL

Courtesy of EXP REALTY LLC
View 543 GREEN SPRING CIRCLE Winter Springs, FL MLS# V4946670
$230,500
2

Beds

1.1

Baths

1,130

Sq.Ft.

543 GREEN SPRING CIRCLE

Winter Springs, FL

Courtesy of COLDWELL BANKER 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
View 506 CLUB DRIVE Winter Springs, FL MLS# O6362326
$237,000
2

Beds

2.0

Baths

1,002

Sq.Ft.

506 CLUB DRIVE

Winter Springs, FL

Courtesy of CALL IT CLOSED INTL REALTY
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

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

208

Estimated median home price

$429,950
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 - 200K6
$200K - 300K34
$300K - 400K53
$400K - 500K55
$500K - 600K15
$600K - 700K11
$700K - 800K13
$800K - 900K7
$900K - 1M4
$1M - Max9

Homes for Sale by Type in Winter Springs, FL

Property TypeCount
Single Family132
Townhouse53
Condo13
Commercial3
Rental40
Lots and Land6
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 3/13/2026)

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 3/14/2026.