20 E Division St, photo 1
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Overview

4 bd3 ba2,729 sqft1 car garageSingle Family
TypeSingle Family
HOANone listed
Built1959
Lot12,982 sqft
Living area2,729 sqft
Price / sqft$365
Garage1 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Eat-in KitchenKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSaunaWalk-in Closet(s)GardenPrivate Yard

20 E Division St is a 1959-built home in Winter Garden Shores First Add, Winter Garden. Inside you'll find 4 bedrooms, 3 bathrooms, and 2,729 square feet of living space. Listed at $995,000 (about $365/sqft), 130 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

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!!!

The essentials

Built
1959
Price / sqft
$365
On market
130 days
Annual tax
$7,197
Flood zone
X · Low risk
Lot
12,982 sqft
Type
Single Family Residence

At a glance

Single family
Built 1959
Private pool
In Ground
1 car garage
0.30 acres
Lot size
2,729 sqft
Living area

Payment

Est. monthly payment
$6,286/mo
Down payment (20%)
$199,000
Property taxes
$600/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1959
Lot
12,982 sqft
Cooling
Central Air
Heating
Central
Parking
-
Pool
In Ground
Days on Market
130
Eat-in Kitchen
Kitchen/Family Room Combo
Open Floorplan
Primary Bedroom Main Floor
Sauna
Walk-in Closet(s)
Garden
Private Yard
Rain Gutters
Bar Fridge
Convection Oven
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
Wine Refrigerator
Flood Zone X
Annual Tax (2025)
$7,197
Parcel #
14-22-27-9388-01-010

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Winter Garden Shores First Add
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
12,982 sqft

Price history

Date
Event
Price
9/16/2026
Price change
Source: Stellar MLS #O6413659
$995,000-2.5%
$365/sqft
-
Price change
Source: Stellar MLS #O6413659
$1,020,000-11.2%
$374/sqft
6/3/2026
Listed for sale
Source: Stellar MLS #O6413659
$1,149,000
$421/sqft

Neighborhood

20 E Division St
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $995,000
$990,000 – $995,000
99.5% – 100% of listTops out right at the list price
80% of listList price
222 of the last 443 home closings in 34787 landed at this number or higher (50%). The median one sat 22 days before it went under contract, and this one is on day 130 after a $154,000 cut.

Sample: 443 closed home sales in 34787 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$6,287/mo
Principal & interest$5,189
Property taxes$600
Insurance$498
Down payment20% · $199,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$995,000

$365 per sq ft

Beds and baths

4 beds, 3 baths

Size

2,729 sq ft

Time on market

130 days

Year built

1959

Monthly payment

About $6,286/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $7,197 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

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Have another question?

Brokered byCHARLES RUTENBERG REALTY ORLANDOListing agent: Liz BoyceListing data from Stellar MLS, MLS# O6413659.

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