View 17360 GLOSSY POMELO Winter Garden, FL MLS# O6365246
  • New Construction
1 of 33
$1,499,980
5

Beds

4.1

Baths

4,728

Sq.Ft.

17360 GLOSSY POMELO

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 16636 BROADWATER AVENUE Winter Garden, FL MLS# S5139753
$1,600,000
6

Beds

5.0

Baths

5,177

Sq.Ft.

16636 BROADWATER AVENUE

Winter Garden, FL

Courtesy of MAXIM REALTY ORLANDO
View 15047 SUNSTAR WAY Winter Garden, FL MLS# O6364934
  • Virtual Tour
1 of 47
$1,350,000
5

Beds

6.0

Baths

4,018

Sq.Ft.

15047 SUNSTAR WAY

Winter Garden, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View SEIDEL ROAD Winter Garden, FL MLS# O6364566
$1,500,000
Studio

Beds

0.0

Baths

SEIDEL ROAD

Winter Garden, FL

Courtesy of LEGACY PLUS REALTY
View 14424 ELLERBEE STREET Winter Garden, FL MLS# O6361850
$1,500,000
Studio

Beds

0.0

Baths

14424 ELLERBEE STREET

Winter Garden, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 15332 JOHNS LAKE POINTE BOULEVARD Winter Garden, FL MLS# O6359467
$1,399,000
4

Beds

4.1

Baths

4,123

Sq.Ft.

15332 JOHNS LAKE POINTE BOULEVARD

Winter Garden, FL

Courtesy of CLOCK TOWER REALTY
View 17384 GLOSSY POMELO WAY Winter Garden, FL MLS# O6358512
  • New Construction with Virtual Tour
1 of 85
$1,475,000
6

Beds

4.1

Baths

4,676

Sq.Ft.

17384 GLOSSY POMELO WAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 557 W PLANT STREET Winter Garden, FL MLS# O6356390
  • Virtual Tour
1 of 12
$1,390,033
2,564

Sq.Ft.

557 W PLANT STREET

Winter Garden, FL

Courtesy of VALSTAR REALTY LLC
View 624 CANOPY ESTATES DRIVE Winter Garden, FL MLS# O6354768
$1,350,000
4

Beds

4.1

Baths

3,627

Sq.Ft.

624 CANOPY ESTATES DRIVE

Winter Garden, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 1096 RIVERWAY DRIVE Winter Garden, FL MLS# O6357557
  • New Construction
1 of 95
$1,700,000
4

Beds

3.1

Baths

4,171

Sq.Ft.

1096 RIVERWAY DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 16548 RAVEN ROCK PLACE Winter Garden, FL MLS# S5134920
$1,525,000
5

Beds

4.1

Baths

4,263

Sq.Ft.

16548 RAVEN ROCK PLACE

Winter Garden, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 5526 TINY ROAD Winter Garden, FL MLS# O6334009
  • Virtual Tour
1 of 39
$1,675,000
3

Beds

2.2

Baths

2,474

Sq.Ft.

5526 TINY ROAD

Winter Garden, FL

Courtesy of BUYER REBATES REALTY
View 10291 ATWATER BAY DRIVE Winter Garden, FL MLS# O6326819
$1,324,950
5

Beds

3.1

Baths

3,910

Sq.Ft.

10291 ATWATER BAY DRIVE

Winter Garden, FL

Courtesy of REVEL REALTY LLC
View 15264 SHONAN GOLD DRIVE Winter Garden, FL MLS# O6323439
$1,500,000
4

Beds

3.1

Baths

4,000

Sq.Ft.

15264 SHONAN GOLD DRIVE

Winter Garden, FL

Courtesy of JULIAN PROPERTIES, INC.
View 7031 BILLIE COURT Winter Garden, FL MLS# O6294514
  • Virtual Tour
1 of 57
$1,580,000
4

Beds

4.0

Baths

3,487

Sq.Ft.

7031 BILLIE COURT

Winter Garden, FL

Courtesy of CASTRO REALTY GROUP
View 13217 TOLLCROSS WAY Winter Garden, FL MLS# O6285385
  • New Construction
1 of 78
$1,395,000
6

Beds

5.0

Baths

4,152

Sq.Ft.

13217 TOLLCROSS WAY

Winter Garden, FL

Courtesy of JR CERQUEIRA REALTY CORP
View 166 HAMMOCK PRESERVE LOOP Winter Garden, FL MLS# O6283425
  • New Construction with Virtual Tour
1 of 64
$1,675,000
4

Beds

4.0

Baths

3,186

Sq.Ft.

166 HAMMOCK PRESERVE LOOP

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY

About Winter Garden

The balance between reverence for yesterday and vibrant growth is reflected in the Winter Garden slogan, "A City with a Future…Preserving Its Past."  Walking down historic Plant Street or catching a glimpse of landmark buildings like Tanner Hall immediately creates an image of small-town life at its finest in the heart of this quaint Main Street community. At the same time, redevelopment and growth are evident at every turn.  Antique stores, ice cream shops, and charming cafés combine with dynamic new businesses and residential development.  Covering approximately 17 square miles, Winter Garden offers access to the West Orange Trail for biking or jogging in a naturally beautiful setting.  Other amenities include large parks, a public boat ramp on Lake Apopka, and recreational complexes for tennis, swimming, and sports play.  This vast area once covered by citrus groves is rapidly transforming into a suburban environment that preserves the friendly, intimate spirit of yesterday.  Residents enjoy easy access to Highway 50, the East West Expressway, and the Florida Turnpike.

Listings in Winter Garden, FL

774

Estimated median home price

$589,000
Winter Garden FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Garden, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Garden, FL.

Homes for Sale by Price in Winter Garden, FL

Price Count
$0 - 100K 6
$100K - 200K 8
$200K - 300K 64
$300K - 400K 82
$400K - 500K 132
$500K - 600K 123
$600K - 700K 85
$700K - 800K 68
$800K - 900K 63
$900K - 1M 49
$1M - Max 94

Homes for Sale by Type in Winter Garden, FL

Property Type Count
Single Family 502
Townhouse 117
Condo 110
Commercial 9
Rental 224
Lots and Land 32
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 1
Farms 0

(Data as of 1/3/2026)

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 1/3/2026.