Single Family Residence at 20 E DIVISION ST, WINTER GARDEN
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$995,000

20 E DIVISION ST
WINTER GARDEN, FL 34787
Listed by Liz Boyce · CHARLES RUTENBERG REALTY ORLANDO
Bedrooms
4
Bathrooms
3
Living area
2,729 sqft
Year built
1959

About this home

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!!!

Highlights

Private poolFireplace

Property details

MLS #
MFRO6413659
Property type
Single Family Residence
Subdivision
WINTER GARDEN SHORES FIRST ADD
Status
Active
Days on market
103
On market date
June 5, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
1
Parking spaces
N/A
Lot size
0.3 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
DILLARD STREET ELEMENTARY
0.19 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
528
Student:teacher ratio
16.0:1
District
ORANGE
Middle
LAKEVIEW MIDDLE
1.23 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
828
Student:teacher ratio
18.8:1
District
ORANGE
High
ORANGE TECHNICAL COLLEGE WESTSIDE CAMPUS
1.22 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
0
Student:teacher ratio
0.0:1
District
ORANGE

Walkability

Blended score for WINTER GARDEN's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

34
Car-dependent
out of 100
EPA National Walkability Index
7.2 / 20 -- Below average walkable
Google Places amenity density
30 / 100
Restaurants & cafes0
Grocery stores0
Parks3
Schools3
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in WINTER GARDEN, from live MLS data.

On the market 103 days -- 28 more days than WINTER GARDEN's current average of 75 days.
For reference, the median list price across 1,032 active listings in WINTER GARDEN right now is $489,070.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$6,142/mo
$199,000 down
$796,000 loan
Principal & interest$5,163
Property tax (est.)$829
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 19 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.