Address
241 N Dillard Street, WINTER GARDEN, FL
Price
$ 1,499,999
Property Attributes
- MLS#O6353975
- TypeSingle Family
- Listing Status Active
- CountyOrange
- CityWINTER GARDEN
- AreaWinter Garden/Oakland
- NeighborhoodJ L DILLARD SUB 3
- Zip34787
- StyleTraditional
- Year Built1953
- Taxes$ 2959
- Price$ 1,499,999
- Bedrooms4
- Full Bathrooms3
- Half Bathrooms0
- Sqr Footage3507
- Lot Size0.64 Acres
Data Source:
Stellar MLS
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.
| Elementary School | Middle School | High School |
|---|---|---|
| Dillard Street Elem Elementary School | Lakeview Middle Middle School | West Orange High High School |
| Price History | |
|---|---|
| 12/19/2025 | Listed $1,800,000 |
| 2/19/2026 | 3$1,750,000 |
| 3/24/2026 | 9$1,600,000 |
| 4/13/2026 | 6$1,499,999 |
General Features
| Sewer | Public Sewer |
|---|---|
| Heating | Central,Electric |
| Cooling | Central Air |
| Utilities | BB/HS Internet Available,Cable Connected,Electricity Connected,Natural Gas Connected,Phone Available,Sewer Connected,Water Connected |
| Roof | Shingle |
| Appliances | Built-In Oven,Cooktop,Dishwasher,Disposal,Dryer,Gas Water Heater,Microwave,Range Hood,Refrigerator,Washer |
| Zoning | R-2 |
| Patio/Porch Features | Patio,Porch,Rear Porch |
| Architectural Style | Traditional |
| Construction Materials | Block,Concrete |
| Pets Allowed | Yes |
| Year Built | 1953 |
| Levels | One |
| Property Subtype | Single Family Residence |
| Tax Year | 2024 |
| Ownership | Fee Simple |
| County | Orange |
| New Construction | false |
| Property Type | Residential |
| Subdivision Name | J L DILLARD SUB 3 |
| Facing Direction | West |
| Garage Y/N | false |
| Total Rooms | 7 |
| Full Baths | 3 |
| Status | Active |
| Directions | Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right. |
| High School | West Orange High |
| City | WINTER GARDEN |
| Senior Community Y/N | false |
| MLS Area | 34787 - Winter Garden/Oakland |
| Lot Size Units | Square Feet |
| Lot Size Square Feet | 27988 |
| Carport Spaces | 6 |
| Carport Y/N | true |
| Listing Terms | Cash,Conventional,VA Loan |
| Elementary School | Dillard Street Elem |
| Land Lease Y/N | false |
| Tax Annual Amount | 2959 |
| Middle/Junior High School | Lakeview Middle |
| Additional Parcels Y/N | false |
| Lease Considered Y/N | true |
| Virtual Tour | https://www.zillow.com/view-imx/37f39412-fc82-4833-8cd6-c4ee120d5e6a?wl=true&setAttribution=mls&initialViewType=pano |
| Building Area Units | Square Feet |
| Living Area Units | Square Feet |
| Standard Status | Active |
| Occupancy Type | Owner |
| Tax Lot | 1 |
| Legal Description | J L DILLARD SUB NO 3 R/36 LOTS 1 & 2 |
| Minimum Lease | 8-12 Months |
| Water Access Y/N | false |
| Additional Rooms | Bonus Room,Inside Utility |
| Water View Y/N | false |
| Flood Zone Code | X |
| In Law Suite YN | false |
| Flood Zone Code X | Yes |
Interior Features
| Interior Amenities | Ceiling Fan(s),Crown Molding,Eating Space In Kitchen,High Ceilings,Kitchen/Family Room Combo,Living Room/Dining Room Combo,Open Floorplan,Stone Counters |
|---|---|
| Flooring | Carpet,Hardwood |
| Fireplace Features | Other Room,Wood Burning |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Fireplace Y/N | true |
| Laundry Features | Inside,Laundry Room |
| Total Bedrooms | 4 |
| LivingAreaSource | Owner |
| Total Baths | 3 |
Exterior Features
| Exterior Amenities | Courtyard,French Doors,Garden,Irrigation System,Lighting,Sidewalk,Storage |
|---|---|
| Vegetation | Mature Landscaping,Oak Trees,Trees/Landscaped |
| Parking Features | Covered,Driveway,Garage Faces Side |
| Lot Features | Corner Lot,City Lot,In County,Landscaped,Level,Oversized Lot,Sidewalk |
| Water Source | Public |
| Lot Size Area | 27988 |
| Foundation Details | Slab |
| Building Area Total | 4671 |
| Lot Size Acres | 0.64 |
| Road Surface Type | Paved |
| Private Pool | false |
| Waterfront Y/N | false |
| Covered Spaces | 6 |
| Road Frontage Type | Street Paved |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 34787
Price
Taxes
Year Built
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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Updated on September 19, 2026 6:31 AM UTC
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Data Last Updated: September 19, 2026 7:03 AM UTC
