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Winter Garden

A charming little city with a juicy past

Winter Garden is a “small-town” city, with a big-time history. Recent development has added to the small-town charm while preserving the heritage that has made Winter Garden what it is today. Built on the back of the citrus industry during the end of the 19th century, Winter Garden has consistently grown for over a hundred years. Walking through the city you can see the success that Winter Garden has effectuated since the very first election in 1903 transformed into a modern haven for art, community, and economy.

Located at what locals call the “high point of Florida”, Winter Garden is in close proximity to everything of note in the State. Just hours from the beaches, minutes from attractions, Orlando, and the airport, Winter Garden is truly the hub of our sunny State. At that hub you will find enough entertainment and history to keep you entertained for hours on end. The old-fashioned shops and restaurants have been remodeled to meet modern conveniences while keeping to their quaint styles.

Take a stroll down the red bricked streets and listen to live music, while you take in the history or toss a coin into the water fountain. Walk into the lobby of the Edgewater Hotel est. 1927 and run your hands across the original wood countertops or marvel at the fully operational 1926 Otis elevator. Once a popular destination for businessmen and celebrities, Winter Garden is now a popular destination for people to live and visit with a penchant for small-town charm.

The railroad runs through the heart of the city and was once the main vein that kept Winter Garden connected with the rest of the Nation. The Railroad Museum and the bright yellow caboose in front of the Heritage Museum serve to keep Winter Garden connected to the rich history that it was founded on.

The Winter Garden Theatre or “Garden Theatre” as it is known around town, was recently restored. In order to keep with the original design, the theatre refurbished the 1950’s style marquee and kept the old fashioned ticket booth. Take a walk down memory lane and see movies in the setting that your grandparents saw them, but with all the modern conveniences of our era. G If you are an outdoor person, Winter Garden is certainly right up your alley. Approximately 12 square miles make up the entirety of the city beautiful. You can walk, run, or bike those expanses on the 22 miles of converted railroad track that is known as the West Orange Trail.

Min. Price
Max. Price
Beds
Baths
13377 LAKE BUTLER BOULEVARD WINTER GARDEN, FL 34787
$5,997,000
5 Beds 4 | 1 Baths 6,210 SqFt Listing No. O6100391 Property Type: House camera Virtual Tour camera (11)
Details
14354 ELLERBEE STREET WINTER GARDEN, FL 34787
$3,700,000
5 Beds 5 | 3 Baths 5,729 SqFt Listing No. O6181280 Property Type: House camera Virtual Tour camera (18)
Details
1253 E FULLERS CROSS ROAD WINTER GARDEN, FL 34787
$3,600,000
4 Beds 4 | 1 Baths 3,495 SqFt Listing No. G5049866 Property Type: House camera Virtual Tour camera (9)
Details
900 W PLANT STREET WINTER GARDEN, FL 34787
$3,575,000
7 Beds 6 | 2 Baths 7,704 SqFt Listing No. O6174030 Property Type: House camera Virtual Tour camera (74)
Details
15522 SHOREBIRD LANE WINTER GARDEN, FL 34787
$2,999,777
7 Beds 6 | 1 Baths 6,400 SqFt Listing No. O6170435 Property Type: House camera Virtual Tour camera (43)
Details
17326 PHIL C PETERS ROAD WINTER GARDEN, FL 34787
$2,998,800
4 Beds 5 Baths 10,907 SqFt Listing No. O6159028 Property Type: House camera Virtual Tour camera (86)
Details
7352 JOHN HANCOCK DRIVE WINTER GARDEN, FL 34787
$2,600,000
5 Beds 4 | 1 Baths 5,084 SqFt Listing No. O6174304 Property Type: House camera Virtual Tour camera (86)
Details
7701 SUMMERLAKE POINTE BOULEVARD WINTER GARDEN, FL 34787
$2,400,000
5 Beds 5 Baths 4,072 SqFt Listing No. O6169382 Property Type: House camera Virtual Tour camera (63)
Details
16150 JOHNS LAKE OVERLOOK DRIVE WINTER GARDEN, FL 34787
$2,375,000
5 Beds 4 | 2 Baths 4,477 SqFt Listing No. O6187264 Property Type: House camera Virtual Tour camera (74)
Details
260 DEER ISLE DRIVE WINTER GARDEN, FL 34787
$2,300,000
4 Beds 4 | 1 Baths 4,714 SqFt Listing No. O6135342 Property Type: House camera Virtual Tour camera (54)
Details
1017 JOHNS POINT DRIVE WINTER GARDEN, FL 34787
$2,150,000
5 Beds 6 Baths 6,141 SqFt Listing No. O6182145 Property Type: House camera Virtual Tour camera (46)
Details
16641 BROADWATER AVENUE WINTER GARDEN, FL 34787
$2,100,000
6 Beds 5 | 1 Baths 5,117 SqFt Listing No. O6182925 Property Type: House camera Virtual Tour camera (75)
Details
 13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (11)
price

$5,997,000

beds

5 5 Beds

baths

4 | 1 4 | 1 Baths

lot size

6,210 SqFt 6,210 SqFt

listing no.

O6100391 Listing No. O6100391

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (11)

 14354 ELLERBEE STREET, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (18)
price

$3,700,000

beds

5 5 Beds

baths

5 | 3 5 | 3 Baths

lot size

5,729 SqFt 5,729 SqFt

listing no.

O6181280 Listing No. O6181280

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (18)

 1253 E FULLERS CROSS ROAD, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (9)
price

$3,600,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

3,495 SqFt 3,495 SqFt

listing no.

G5049866 Listing No. G5049866

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (9)

 900 W PLANT STREET, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (74)
price

$3,575,000

beds

7 7 Beds

baths

6 | 2 6 | 2 Baths

lot size

7,704 SqFt 7,704 SqFt

listing no.

O6174030 Listing No. O6174030

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (74)

 15522 SHOREBIRD LANE, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (43)
price

$2,999,777

beds

7 7 Beds

baths

6 | 1 6 | 1 Baths

lot size

6,400 SqFt 6,400 SqFt

listing no.

O6170435 Listing No. O6170435

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (43)

 17326 PHIL C PETERS ROAD, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (86)
price

$2,998,800

beds

4 4 Beds

baths

5 5 Baths

lot size

10,907 SqFt 10,907 SqFt

listing no.

O6159028 Listing No. O6159028

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (86)

 7352 JOHN HANCOCK DRIVE, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (86)
price

$2,600,000

beds

5 5 Beds

baths

4 | 1 4 | 1 Baths

lot size

5,084 SqFt 5,084 SqFt

listing no.

O6174304 Listing No. O6174304

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (86)

 7701 SUMMERLAKE POINTE BOULEVARD, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (63)
price

$2,400,000

beds

5 5 Beds

baths

5 5 Baths

lot size

4,072 SqFt 4,072 SqFt

listing no.

O6169382 Listing No. O6169382

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (63)

 16150 JOHNS LAKE OVERLOOK DRIVE, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (74)
price

$2,375,000

beds

5 5 Beds

baths

4 | 2 4 | 2 Baths

lot size

4,477 SqFt 4,477 SqFt

listing no.

O6187264 Listing No. O6187264

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (74)

 260 DEER ISLE DRIVE, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (54)
price

$2,300,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,714 SqFt 4,714 SqFt

listing no.

O6135342 Listing No. O6135342

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (54)

 1017 JOHNS POINT DRIVE, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (46)
price

$2,150,000

beds

5 5 Beds

baths

6 6 Baths

lot size

6,141 SqFt 6,141 SqFt

listing no.

O6182145 Listing No. O6182145

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (46)

 16641 BROADWATER AVENUE, WINTER GARDEN, FL 34787
camera VIRTUAL TOUR camera (75)
price

$2,100,000

beds

6 6 Beds

baths

5 | 1 5 | 1 Baths

lot size

5,117 SqFt 5,117 SqFt

listing no.

O6182925 Listing No. O6182925

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (75)

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The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of 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; the availability of any listing should always be independently verified. Listing information is provided for consumers' 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. The offer of compensation is made only to participants of the MLS where the listing is filed.
Stellar (MFR) data last updated at March 28, 2024 11:23 AM ET
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