View 431 SOUTHERN PECAN CIRCLE 101 Winter Garden, FL MLS# O6439215
$274,500
3

Beds

2.0

Baths

1,340

Sq.Ft.

431 SOUTHERN PECAN CIRCLE 101

Winter Garden, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 1017 PRIORY CIRCLE Winter Garden, FL MLS# O6438757
$350,000
3

Beds

2.1

Baths

1,625

Sq.Ft.

1017 PRIORY CIRCLE

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 5887 CYPRESS HILL ROAD Winter Garden, FL MLS# O6438059
$450,000
3

Beds

2.1

Baths

1,810

Sq.Ft.

5887 CYPRESS HILL ROAD

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 9467 CINZEL ALLEY Winter Garden, FL MLS# O6434302
$455,000
3

Beds

2.1

Baths

1,814

Sq.Ft.

9467 CINZEL ALLEY

Winter Garden, FL

Courtesy of ENGEL & VOELKERS LAKELAND
View 14501 GROVE RESORT AVENUE 3534 Winter Garden, FL MLS# S5156702
$199,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

14501 GROVE RESORT AVENUE 3534

Winter Garden, FL

Courtesy of FLARE PROPERTIES LLC
View 14501 GROVE RESORT AVENUE 3403 Winter Garden, FL MLS# S5156278
$170,000
2

Beds

2.0

Baths

1,265

Sq.Ft.

14501 GROVE RESORT AVENUE 3403

Winter Garden, FL

Courtesy of FLEXWAY REALTY LLC
View 1424 SCARLET OAK LOOP Winter Garden, FL MLS# O6436325
$379,000
3

Beds

2.1

Baths

1,737

Sq.Ft.

1424 SCARLET OAK LOOP

Winter Garden, FL

Courtesy of TEAMCONNECT REALTY LLC
View 14501 GROVE RESORT AVENUE 2542 Winter Garden, FL MLS# O6436045
$205,000
3

Beds

3.0

Baths

1,544

Sq.Ft.

14501 GROVE RESORT AVENUE 2542

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14501 GROVE RESORT AVENUE 1420 Winter Garden, FL MLS# S5156458
$249,000
2

Beds

2.0

Baths

1,375

Sq.Ft.

14501 GROVE RESORT AVENUE 1420

Winter Garden, FL

Courtesy of FLARE PROPERTIES LLC
View 2017 PORTCASTLE CIRCLE Winter Garden, FL MLS# O6437283
$399,900
3

Beds

2.1

Baths

1,857

Sq.Ft.

2017 PORTCASTLE CIRCLE

Winter Garden, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 15873 GEM VIEW STREET Winter Garden, FL MLS# O6435893
  • Adult Community with Virtual Tour
1 of 58
$414,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

15873 GEM VIEW STREET

Winter Garden, FL

Courtesy of RE/MAX SELECT GROUP
View 225 1ST STREET Winter Garden, FL MLS# TB8541424
$288,000
3

Beds

1.0

Baths

1,020

Sq.Ft.

225 1ST STREET

Winter Garden, FL

Courtesy of HOMERIVER GROUP
View 2628 BALFORN TOWER WAY Winter Garden, FL MLS# S5156147
$438,000
3

Beds

2.0

Baths

1,372

Sq.Ft.

2628 BALFORN TOWER WAY

Winter Garden, FL

Courtesy of LPT REALTY, LLC
View 16510 BARBOURS CREEK WAY Winter Garden, FL MLS# O6435580
  • New Construction with Virtual Tour
1 of 27
$447,500
3

Beds

2.1

Baths

1,567

Sq.Ft.

16510 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 16516 BARBOURS CREEK WAY Winter Garden, FL MLS# O6435583
  • New Construction with Virtual Tour
1 of 27
$424,990
3

Beds

2.1

Baths

1,567

Sq.Ft.

16516 BARBOURS CREEK WAY

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 1422 BASIN STREET Winter Garden, FL MLS# V4950812
$260,000
4

Beds

1.0

Baths

880

Sq.Ft.

1422 BASIN STREET

Winter Garden, FL

Courtesy of CARDINAL ROW REAL ESTATE
View 208 3RD STREET Winter Garden, FL MLS# O6435218
$435,000
0.0

Baths

1,750

Sq.Ft.

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 208 3RD STREET Winter Garden, FL MLS# O6435263
$435,000
0.0

Baths

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 208 3RD STREET Winter Garden, FL MLS# O6435284
$435,000
8

Beds

3.0

Baths

1,750

Sq.Ft.

208 3RD STREET

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 15613 ORANGE HARVEST LOOP Winter Garden, FL MLS# O6435567
$425,000
3

Beds

2.1

Baths

1,844

Sq.Ft.

15613 ORANGE HARVEST LOOP

Winter Garden, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

995

Estimated median home price

$595,000
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

PriceCount
$0 - 100K1
$100K - 200K33
$200K - 300K75
$300K - 400K79
$400K - 500K153
$500K - 600K170
$600K - 700K108
$700K - 800K115
$800K - 900K102
$900K - 1M57
$1M - Max102

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family686
Townhouse151
Condo121
Commercial6
Rental226
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 10/14/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Weichert Realtors are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. 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.

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Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Copyright © 2026 Midwest Real Estate Data LLC.

Data is updated as of 10/14/2026.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 10/14/2026.