$1,499,999
241 Dillard Street
Winter Garden, FL 34787
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history224 days on market
- Status: ActiveOct 20, 2025
- Listed$1,800,000Oct 20, 2025
- Price reduced$1,499,999
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 224
- Subdivision
- J L Dillard Sub 3
- County
- Orange
- Year built
- 1953
- Living area
- 3,507 sq ft
- Price/sq ft
- $428
- Building area
- 4,671 sq ft (Public Records)
- Lot size
- 27,988 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X (12095C0205H)
- Annual taxes
- $2,959 (2024)
- Parcel #
- 27-22-14-2088-00-010
- Zoning
- R-2
- MLS #
- O6353975
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Carpet, Wood
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Stone Counters
- Laundry
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- West
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Parking features
- Covered, Driveway, Garage Faces Side
- Carport
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer to verify with the city
- Approval process
- Buyer to verify with the city
Exterior & Construction
- Exterior features
- Courtyard, French Doors, Garden, Lighting, Sidewalk, Storage
- Construction materials
- Block, Concrete
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Family Room | First | |
| Dining Room | First | |
| Living Room | First | |
| Kitchen | First | |
| Primary Bedroom | First | |
| Bedroom 2 | First | |
| Bedroom 3 | First |
Listing Details
- Listing date
- 2025-10-20
- On market date
- 2025-10-20
- Original list price
- $1,800,000
- Occupant type
- Owner
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2025-10-20
- Tax legal description
- J L DILLARD SUB NO 3 R/36 LOTS 1 & 2
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of June 1, 2026 at 4:23 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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