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Overview

4 bd3 ba3,507 sqftSingle Family
TypeSingle Family
HOANone listed
Built1953
Lot27,988 sqft
Living area3,507 sqft
Price / sqft$428

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About this home

Ceiling Fans(s)Crown MoldingEat-in KitchenHigh CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanStone Counters

241 N Dillard St is a 1953-built home in J L Dillard Sub 3, Winter Garden. Inside you'll find 4 bedrooms, 3 bathrooms, and 3,507 square feet of living space. Listed at $1,499,999 (about $428/sqft), 355 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

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The essentials

Built
1953
Price / sqft
$428
On market
355 days
Annual tax
$2,959
Flood zone
X · Low risk
Lot
27,988 sqft
Type
Single Family Residence

At a glance

Single family
Built 1953
0.64 acres
Lot size
3,507 sqft
Living area

Payment

Est. monthly payment
$8,820/mo
Down payment (20%)
$300,000
Property taxes
$247/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1953
Lot
27,988 sqft
Cooling
Central Air
Heating
Central, Electric
Parking
Covered, Driveway, Garage Faces Side
Days on Market
355
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Open Floorplan
Stone Counters
Courtyard
Garden
Lighting
Sidewalk
Storage
Built-in Oven
Cooktop
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range Hood
Refrigerator
Washer
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 (2024)
$2,959
Parcel #
27-22-14-2088-00-010

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
J L Dillard Sub 3
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
27,988 sqft
Corner LotCity LimitsIn CountyLandscapedLevelOversized LotSidewalkPaved

Price history

Date
Event
Price
4/13/2026
Price change
Source: Stellar MLS #O6353975
$1,499,999-6.3%
$428/sqft
-
Price change
Source: Stellar MLS #O6353975
$1,600,000-11.1%
$456/sqft
10/20/2025
Listed for sale
Source: Stellar MLS #O6353975
$1,800,000
$513/sqft

Neighborhood

241 N Dillard St
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $1,499,999
$1.49M – $1.50M
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 355 after a $300,001 cut.

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

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Calculator

Est. monthly payment
$8,820/mo
Principal & interest$7,823
Property taxes$247
Insurance$750
Down payment20% · $300,000
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

$1,499,999

$428 per sq ft

Beds and baths

4 beds, 3 baths

Size

3,507 sq ft

Time on market

355 days

Year built

1953

Monthly payment

About $8,820/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $2,959 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 byHOMEVEST REALTYListing agent: Erica DiazListing data from Stellar MLS, MLS# O6353975.

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