Property
ActiveResidential
1/52
$1,499,999

241 N DILLARD STREET

Winter Garden, FL 34787
4
Beds
3
Baths
3,507
SqFt
0.64
Acres
STELLAR
#O6353975
Updated: Jun 5, 2026, 12:53pm

Property Description

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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Included Appliances
Built-In OvenCooktopDishwasherDisposalDryerGas Water HeaterMicrowaveRange HoodRefrigeratorWasher

Property Details

Interior
Additional Rooms
Bonus RoomInside Utility
Appliances
Built-In OvenCooktopDishwasherDisposalDryerGas Water HeaterMicrowaveRange HoodRefrigeratorWasher
Bathrooms Total Decimal
3
Building Area Total
4671
Cooling
Central Air
Fireplace Features
Other RoomWood Burning
Flooring
CarpetHardwood
Heating
CentralElectric
Interior Features
Ceiling Fan(s)Crown MoldingEating Space In KitchenHigh CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanStone Counters
Laundry Features
InsideLaundry Room
Living Area
3507
Rooms Total
7
Construction
Architectural Style
Traditional
Building Area Source
Public Records
Building Area Units
Square Feet
Construction Materials
BlockConcrete
Direction Faces
West
Foundation Details
Slab
Levels
One
Living Area Source
Owner
Living Area Units
Square Feet
Roof
Shingle
Year Built
1953
Site & Exterior
Carport Spaces
6
Covered Spaces
6
Exterior Features
CourtyardFrench DoorsGardenIrrigation SystemLightingSidewalkStorage
Flood Zone Code
X
I D X Participation
Yes
Lot Features
Corner LotCity LotIn CountyLandscapedLevelOversized LotSidewalk
Lot Size Acres
0.64
Lot Size Area
27988
Lot Size Square Feet
27988
Lot Size Units
Square Feet
Open Parking
Yes
Parking Features
CoveredDrivewayGarage Faces Side
Patio And Porch Features
PatioPorchRear Porch
Public Survey Range
27
Public Survey Section
14
Road Frontage Type
Street Paved
Road Surface Type
Paved
Sewer
Public Sewer
Total Acreage
1/2 to less than 1
Utilities
BB/HS Internet AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedPhone AvailableSewer ConnectedWater Connected
Vegetation
Mature LandscapingOak TreesTrees/Landscaped
Water Source
Public
Zoning
R-2
Financials
Calculated List Price By Calculated Sq Ft
427.72
Contract Status Change Date
2025-10-20
Current Price
1499999
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
8-12 Months
Ownership
Fee Simple
Parcel Number
272214208800010
Public Survey Township
22
Tax Annual Amount
2959
Tax Block
-
Tax Book Number
R-36
Tax Legal Description
J L DILLARD SUB NO 3 R/36 LOTS 1 & 2
Tax Lot
Yes
Tax Year
2024

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
Buyer to verify with the city
Lease Restrictions
Yes
M L S Area Major
34787 - Winter Garden/Oakland
Pet Restrictions
Buyer to verify with the city
Pets Allowed
Yes
Subdivision Name
J L DILLARD SUB 3
Schools
Ratings
Elementary
Dillard Street Elem
Middle
Lakeview Middle
High
West Orange High
Listing provided courtesy of STELLAR via IDX. Updated: Jun 5, 2026, 12:53pm.
Erica Diaz

Listing Agent

HOMEVEST REALTY

Call Agent