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$1,149,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,729 Sq. Ft.
  • Updated 1 day ago
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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!!!

Full Property Details for 20 E Division St

General

  • Price: $1,149,000
  • Taxes: $7,197 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6413659
  • Updated: 6/5/2026
  • Added to Site: 3 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 3
  • Interior Features: Eating Space In Kitchen, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Sauna, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room
  • Appliances: Bar Fridge, Convection Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Luxury Vinyl, Marble, Porcelain Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Garden, Private Yard, Rain Gutters, Sauna

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 1
  • Covered Spaces: 1

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WINTER GARDEN SHORES FIRST ADD
  • Driving Directions: Dillard street turn left onto E Division street, home is on your left.
  • Direction Faces: North

Community

  • Community Name: 34787 - Winter Garden/Oakland

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Available

Structural Information

  • Exterior Const.: Concrete
  • Roof: Shingle
  • Common Walls: Corner Unit
  • Windows: Shutters
  • Stories/Levels: One
  • Square Feet: 2,729
  • Sq. Ft. Source: Appraiser
  • Year Built: 1959

Lot Features

  • Lot Size (Acres): 0.3
  • Lot Size (Sq. Ft.): 12,982
  • Lot Size: 12982
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Tax Amount: $7,197
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINTER GARDEN SHORES FIRST ADDITION T/86LOT 1 BLK A
  • Flood Zone Info: X
  • APN: 142227938801010
  • Property ID: 142227938801010
  • Block/Lot/Section: A

Listed by Charles Rutenberg Realty Orlando

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Listing agent

— 20 E Division St —

  • Charles Rutenberg Realty Orlando

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 20 E Division St

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.2 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81.3 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20 E Division St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/05/2026
Listed
$1,149,000
53.2%
MLS
8/01/2024
Sold
$750,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 20 E Division St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,197
—
$442,510
-3%
2025
$7,197
119%
$456,670
86%
2024
$3,282
5%
$245,574
4%
2023
$3,127
79%
$236,480
61%
2021
$1,743
-71%
$146,779
-62%
2022
$6,098
250%
$381,880
164%
2021
$1,743
2%
$144,752
2%
2019
$1,702
1%
$141,498
2%
2018
$1,681
3%
$138,860
2%
2017
$1,632
1%
$136,004
2%
2016
$1,623
-2%
$133,207
1%
2015
$1,652
-1%
$132,281
1%
2014
$1,662
3%
$131,231
1%
2013
$1,616
—
$129,292
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Charles Rutenberg Realty Orlando

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20 E Division Street, Winter Garden, FL 34787 (MLS# O6413659) is a Single Family property with 4 bedrooms and 3 full bathrooms. 20 E Division Street is currently listed for $1,149,000 and was received on June 05, 2026. Want to learn more about 20 E Division Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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