Home in 241 N Dillard St Winter Garden for sale with MLS# O6353975
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 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.
241 N Dillard St, Winter Garden, FL 34787
- Price:
- $1,499,999.00
- Previous Asking Price:
- $1,600,000.00
- Original List Price:
- $1,800,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $427.72
- Listing Type:
- For Sale
- Status:
- Active
- Previous Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6353975
- Bedrooms:
- 3
- Bathrooms Total:
- 3
- Full Bath:
- 3
- Additional Rooms:
- Inside Utility, Bonus Room
- Living Area:
- 3,507 Sqft
- Built-Up Area:
- 4,671 Sqft
- Lot Area:
- 27,988 Sqft
- Building Area Source:
- Public Records
- Living Area Source:
- Owner
- Lot Features:
- Corner Lot, Oversized Lot, Paved, Level, City Limits, In County, Sidewalk, Landscaped
- Lot Size Acres:
- 0.64
- Waterfront:
- No
- Appliances:
- Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Cooktop, Built-in Oven, Gas Water Heater, Range Hood
- Interior:
- Eat-in Kitchen, High Ceilings, Ceiling Fans(s), Kitchen/family Room Combo, Living Room/dining Room Combo, Open Floorplan, Stone Counters, Crown Molding
- Exterior:
- Lighting, Courtyard, Sidewalk, French Doors, Storage, Garden
- Patio and Porch:
- Patio, Porch, Rear Porch
- Laundry:
- Inside, Laundry Room
- Fireplace
- Fireplace:
- Wood Burning, Other
- Air Conditioning System:
- Central Air
- Heating System:
- Central, Electric
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping, Oak Trees
- Property Entrance Faces:
- West
- Other Equipment:
- Irrigation Equipment
- Year Built:
- 1953
- Roof:
- Shingle
- Architectural Style:
- Traditional
- Levels:
- One
- Construction Materials:
- Block, Concrete
- Flooring:
- Carpet, Wood
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Homestead Property
- Tax Annual Amount:
- $2,959.00
- Tax Year:
- 2024
- Carport Spaces:
- 6
- Parking Features:
- Driveway, Covered, Garage Faces Side
- Carport
- Sewer:
- Public Sewer
- Utilities Available:
- Phone Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected, Cable Connected, Broadband/High Speed Internet Available
- Water Source:
- Public
- Minimum Lease Term:
- 8-12 Months
- Pets Allowed?
- Subdivision Name:
- J L DILLARD SUB 3
- Senior Community:
- No
- Number of Ownership Years Prior To Lease:
- 0
- Listing Terms Considered by Seller:
- Cash, Conventional, VA Loan
- Occupant Type:
- Owner
- Lease Considered:
- Yes
- Tax Legal Description:
- J L DILLARD SUB NO 3 R/36 LOTS 1 & 2
- Real Estate Folio Number (Parcel Number):
- 27-22-14-2088-00-010
- Zoning:
- R-2
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Cooper City
- High School:
- West Orange High
- Middle Or Junior School:
- Lakeview Middle
- Originally published on:
- October 20, 2025 4:00 am
- Active on the market since:
- October 20, 2025
- Listing Agreement executed on:
- October 20, 2025
- Price change occurred on:
- April 13, 2026 3:50 pm
- Listing Status Last Changed On:
- October 20, 2025 7:45 pm
- Photos updated on:
- March 31, 2026 4:36 pm
- Last Modified:
- April 13, 2026 3:51 pm
- Courtesy of:
- HOMEVEST REALTY
- Attribution:
- 407-897-5400
- Road Surface Type:
- Paved
- Street Name:
- DILLARD
- Street Number:
- 241
- City:
- WINTER GARDEN
- State:
- Florida
- Zip Code:
- 34787
- County:
- Orange
- Latitude:
- N28° 34' 8.4''
- Longitude:
- W82° 25' 0.2''
Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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