View 144 TILDENVILLE SCHOOL ROAD Winter Garden, FL MLS# O6439913
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$899,900
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144 TILDENVILLE SCHOOL ROAD

Winter Garden, FL

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

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View ARROWHEAD BOULEVARD Winter Garden, FL MLS# S5155609
$299,900
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ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of FLORIDA REALTY RESULTS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17101 ARROWHEAD BOULEVARD Winter Garden, FL MLS# O6430801
$299,000
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17101 ARROWHEAD BOULEVARD

Winter Garden, FL

Courtesy of Orlando - WEICHERT, REALTORS® - Hallmark Properties
View 9444 LAKE HICKORY NUT DRIVE Winter Garden, FL MLS# O6426404
$639,000
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9444 LAKE HICKORY NUT DRIVE

Winter Garden, FL

View AVALON ROAD UNIT 53 Winter Garden, FL MLS# O6421486
$195,000
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AVALON ROAD UNIT 53

Winter Garden, FL

Courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY
View 3421 REX DRIVE Winter Garden, FL MLS# O6410341
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$695,000
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3421 REX DRIVE

Winter Garden, FL

View 441 E CYPRESS STREET Winter Garden, FL MLS# O6407560
$305,000
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441 E CYPRESS STREET

Winter Garden, FL

View AVALON ROAD Winter Garden, FL MLS# O6404433
$200,000
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AVALON ROAD

Winter Garden, FL

View 0 9TH STREET Winter Garden, FL MLS# O6398357
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$299,000
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0 9TH STREET

Winter Garden, FL

View 1401 N FULLERS CROSS ROAD Winter Garden, FL MLS# O6385497
$395,000
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1401 N FULLERS CROSS ROAD

Winter Garden, FL

View 47 OAK STREET Winter Garden, FL MLS# O6370459
$550,000
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47 OAK STREET

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 12325 & 12303 STAGG ROAD Winter Garden, FL MLS# O6358096
$400,000
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12325 & 12303 STAGG ROAD

Winter Garden, FL

Courtesy of CENTURY 21 CARIOTI
View 188 MARY STREET Winter Garden, FL MLS# O6352643
$119,000
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188 MARY STREET

Winter Garden, FL

Courtesy of TOP ORLANDO REALTY
View 17902 SEIDNER ROAD Winter Garden, FL MLS# O6316521
$2,700,000
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17902 SEIDNER ROAD

Winter Garden, FL

Courtesy of FLORIDA REALTY EXCHANGE LLC
View 851 9TH STREET Winter Garden, FL MLS# O6306969
$1,000,000
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851 9TH STREET

Winter Garden, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 13377 LAKE BUTLER BOULEVARD Winter Garden, FL MLS# O6304334
$2,500,000
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13377 LAKE BUTLER BOULEVARD

Winter Garden, FL

Courtesy of BLUE MAGNOLIA REALTY LLC
View 17144 PHIL C PETERS ROAD Winter Garden, FL MLS# O6260547
$975,000
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17144 PHIL C PETERS ROAD

Winter Garden, FL

View 764 KLONDIKE STREET Winter Garden, FL MLS# O6255583
$59,000
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764 KLONDIKE STREET

Winter Garden, FL

View W ORANGE COUNTRY CLUB DRIVE Winter Garden, FL MLS# O6244629
$400,000
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W ORANGE COUNTRY CLUB DRIVE

Winter Garden, FL

Courtesy of KELLY RIGHT REAL ESTATE

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

998

Estimated median home price

$606,720
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 - 200K21
$200K - 300K90
$300K - 400K70
$400K - 500K148
$500K - 600K166
$600K - 700K105
$700K - 800K110
$800K - 900K111
$900K - 1M62
$1M - Max114

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family697
Townhouse137
Condo129
Commercial7
Rental183
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home1
Farms0

(Data as of 9/7/2026)

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 9/9/2026.