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Overview

2 bd1 ba1,034 sqftSingle Family
TypeSingle Family
HOANone listed
Built1955
Lot8,442 sqft
Living area1,034 sqft
Price / sqft$387

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

About this home

Ceiling Fans(s)Private MailboxPrivate Yard

721 S Woodland St is a 1955-built home in Borders & Woosley Sub, Winter Garden. Inside you'll find 2 bedrooms, 1 bathrooms, and 1,034 square feet of living space. Listed at $400,000 (about $387/sqft), 115 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.

The essentials

Built
1955
Price / sqft
$387
On market
115 days
Annual tax
$508
Flood zone
X · Low risk
Lot
8,442 sqft
Type
Single Family Residence

At a glance

Single family
Built 1955
8,442 sqft lot
Lot size
1,034 sqft
Living area

Payment

Est. monthly payment
$2,328/mo
Down payment (20%)
$80,000
Property taxes
$42/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1955
Lot
8,442 sqft
Cooling
Central Air
Heating
Electric
Parking
Driveway
Days on Market
115
Ceiling Fans(s)
Private Mailbox
Private Yard
Elementary
Dillard Street Elem
Middle
Lakeview Middle
High
West Orange High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2025)
$508
Parcel #
23-22-27-0832-01-090

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
Borders & Woosley Sub
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
8,442 sqft

Price history

Date
Event
Price
10/7/2026
Price change
Source: Stellar MLS #O6419636
$400,000-9.1%
$387/sqft
-
Price change
Source: Stellar MLS #O6419636
$440,000-2.2%
$426/sqft
6/22/2026
Listed for sale
Source: Stellar MLS #O6419636
$450,000
$435/sqft

Neighborhood

721 S Woodland St
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $400,000
$397,500 – $400,000
99.5% – 100% of listTops out right at the list price
80% of listList price
222 of the last 442 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 115 after a $50,000 cut.

Sample: 442 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
$2,329/mo
Principal & interest$2,086
Property taxes$42
Insurance$200
Down payment20% · $80,000
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

$400,000

$387 per sq ft

Beds and baths

2 beds, 1 baths

Size

1,034 sq ft

Time on market

115 days

Year built

1955

Monthly payment

About $2,328/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $508 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

What should I offer?

Have another question?

Brokered byKELLER WILLIAMS CLASSICListing agent: Christopher BessetteListing data from Stellar MLS, MLS# O6419636.

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