Price Reduced Listing
$1,020,000
 $5,476 est/mo Sourced by Back At You

20 E Division St,WINTER GARDEN, FL 34787

WINTER GARDEN, FL 34787

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Description

Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip-it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!

Details

MLS #O6413659
Listing TypeFor Sale
StyleHouse
Sub-TypeFor-sale
StatusActive
Year1959
Days On Site101
Listing Provided ByCHARLES RUTENBERG REALTY ORLANDO | Liz Boyce

Features

Bed(s)4
Bath(s) 3 Total
SQ Feet2,729
Garage1
PoolYes
Story(s)1
ZoningR-1
Acreage0.30

Taxes

Property7197

Area Information

StateFL
CountyOrange
CityWINTER GARDEN
Zip Code34787
Area34787 Winter Garden | Oakland
Community NameWINTER GARDEN SHORES FIRST ADD
Listing VS Median (in WINTER GARDEN SHORES FIRST ADD)
Price:
$1,020,000
low | high
Med:
$1,020,000
50% of Average
sqft:
2,729
low | high
Med:
2,729
50% of Average
$ / sqft:
$374
low | high
Med:
$374
50% of Average
On site:
101
low | high
Med:
101
100% of Average
Sourced by Back At You

Market Activity 34787

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 Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 14, 2026 at 7:16:52 PM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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Learn More About This Property

StateFL
CountyOrange
CityWINTER GARDEN
Zip Code34787
Area34787 Winter Garden | Oakland
Community NameWINTER GARDEN SHORES FIRST ADD
Listing VS Median (in WINTER GARDEN SHORES FIRST ADD)
Price:
$1,020,000
low | high
Med:
$1,020,000
50% of Average
sqft:
2,729
low | high
Med:
2,729
50% of Average
$ / sqft:
$374
low | high
Med:
$374
50% of Average
On site:
101
low | high
Med:
101
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/4 mile)
Price: $765K - $1.275M
sqft: 2,000 - 3,000
Nearby Listings Property ImageNearby Listings Details
412 N BOYD ST Property Photo 1
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412 N Boyd St
Winter Garden, FL 34787
205 SURPRISE DR Property Photo 1
$1,200,000
205 Surprise Dr
Winter Garden, FL 34787
368 N BOYD ST Property Photo 1
$849,900
368 N Boyd St
Winter Garden, FL 34787
Listing Updated: September 3, 2026 at 11:22:28 AM PDT