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$1,499,999
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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.
Full Property Details
Full Property Details for 241 N Dillard St
General
- Price: $1,499,999
- Taxes: $2,959 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6353975
- Updated: 5/4/2026
- Added to Site: 197 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Stone Counters
- Fireplace: Yes
- Fireplace(s): Other Room, Wood Burning
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer
- Flooring: Carpet, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Exterior
- Exterior Features: Courtyard, French Doors, Garden, Irrigation System, Lighting, Sidewalk, Storage
- Deck/Patio: Patio, Porch, Rear Porch
- Porch/Patio/Deck: Patio, Porch, Rear Porch
Parking
- Carports: Yes
- Carport: 6
- Carport Spaces: 6
- Covered Spaces: 6
- Parking Features: Covered, Driveway, Garage Faces Side
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: J L DILLARD SUB 3
- Driving Directions: Head west on State Rte 50 W. Turn right onto S Dillard St. In 1.2 mi. property will be on the right.
- Direction Faces: West
School Information
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Pet Restrictions: Buyer to verify with the city
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Water Connected
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Block, Concrete
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 3,507
- Sq. Ft. Source: Owner
- Year Built: 1953
Lot Features
- Lot Size (Acres): 0.64
- Lot Size (Sq. Ft.): 27,988
- Lot Size: 27988
- Frontage: Street Paved
- Street/Road Desc.: Paved
Financial Considerations
- Tax Amount: $2,959
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: J L DILLARD SUB NO 3 R/36 LOTS 1 & 2
- Flood Zone Info: X
- APN: 272214208800010
- Property ID: 272214208800010
- Block/Lot/Section: -
Listed by Homevest Realty
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Schools
Schools serving 241 N Dillard St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dillard Street Elementary School 311 North Dillard Street, Winter Garden, FL 34787 | PK-5 | 0.1 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1.3 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 2.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 241 N Dillard St
Date
Details
Price
Change
Source
4/13/2026
Price Reduced
$1,499,999
-6.25%
MLS
3/24/2026
Price Reduced
$1,600,000
-8.57%
MLS
2/19/2026
Price Reduced
$1,750,000
-2.78%
MLS
10/20/2025
Listed
$1,800,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 241 N Dillard St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,118
5%
$238,133
6%
2024
$2,959
4%
$225,337
3%
2023
$2,846
5%
$218,774
6%
2021
$2,709
-2%
$206,216
-3%
2022
$2,755
2%
$212,402
4%
2021
$2,709
2%
$203,369
2%
2019
$2,657
1%
$198,797
2%
2018
$2,629
3%
$195,090
2%
2017
$2,557
—
$191,077
2%
2016
$2,549
-2%
$187,147
1%
2015
$2,594
-1%
$185,846
1%
2014
$2,610
3%
$184,371
2%
2013
$2,546
—
$181,646
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 241 N Dillard St
241 N Dillard Street, Winter Garden, FL 34787 (MLS# O6353975) is a Single Family property with 3 bedrooms and 3 full bathrooms. 241 N Dillard Street is currently listed for $1,499,999 and was received on October 20, 2025. Want to learn more about 241 N Dillard Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

