241 N DILLARD STREET
WINTER GARDEN, FL, 34787
Price$1,750,000
Beds3
Baths3
SqFt3,507
Baths3
SqFt3,507
Status:Active
Property Type:Residential
School:
Property Type:Residential
School:
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden
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 two-and-a-half baths, 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.
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 two-and-a-half baths, 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.
| Price | $1,750,000 | |
| Bedrooms | 3 | |
| Full Baths | 2 | |
| Half Baths | 1 | |
| Total Baths | 3 | |
| Property Style | Traditional | |
| Lot Size Area | 27988 | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.64 | |
| Property Type | Residential | |
| Sub type | Single Family Residence | |
| MLS Sub type | Single Family Residence | |
| Features | Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Stone Counters | |
| Exterior Features | Courtyard, French Doors, Garden, Irrigation System, Lighting, Sidewalk, Storage | |
| Year Built | 1953 | |
| Subdivision | J L DILLARD SUB 3 | |
| Roof | Shingle | |
| Heating | Central, Electric | |
| Foundation | Slab | |
| Lot Description | Corner Lot, City Lot, In County, Landscaped, Level, Oversized Lot, Sidewalk | |
| Laundry Features | Inside, Laundry Room | |
| Parking Description | Covered, Driveway, Garage Faces Side | |
| Directions | Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right. | |
| County | Orange | |
| Latitude | 28.568996 | |
| Longitude | -81.583285 | |
| Market Area | 34787 – Winter Garden/Oakland | |
| Address | 241 N DILLARD STREET, WINTER GARDEN, FL 34787 | |
| Postal Code | 34787 | |
| City | WINTER GARDEN | |
| State | FL | |
| Country | United States | |
| Listing Office | HOMEVEST REALTY | |
| Listing Office Phone | 407-897-5400 | |
| Listing Agent | Erica Diaz | |
| Listing Agent Phone | 407-897-5400 | |
| Virtual Tour U R L Unbranded2 | https://www.youtube.com/watch?v=oGiAAzEyzPkPlay VideoZapier is unable to process your request. | |
| Compensation Disclaimer | The offer of compensation is made only to participants of the MLS where the listing is filed. | |
| Special listing conditions | None | |
| Ownership | Fee Simple | |
| Terms | Cash, Conventional, VA Loan | |
| Virtual Tour URL | https://www.zillow.com/view-imx/37f39412-fc82-4833-8cd6-c4ee120d5e6a?wl=true&setAttribution=mls&initialViewType=pano | |
| Elementary School | Dillard Street Elem | |
| Middle School | Lakeview Middle | |
| High School | West Orange High | |
| Days on market | 122 | |
| MLS Status | Active | |
| Listing Date | Oct 20, 2025 | |
| Listing Last Modified | Feb 19, 2026 | |
| Tax ID | 272214208800010 | |
| Tax Year | 2024 | |
| Tax Annual Amount | 2959 | |
| MLS Area | 34787 – Winter Garden/Oakland | |
| MLS # | O6353975 | |
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