241 Dillard Street, FL

$1,499,999

241 Dillard Street

Winter Garden, FL 34787

Active
4
Beds
3
Baths
3,507
Sq Ft
0.64
Acres
1953
Built
Fireplace$428/sqft
🏠Single Family Residence

Property type

🏗️1953

Year built

📐27,988 sqft

Lot size

📊$428

Price / sq ft

🏘️No HOA

HOA dues

📅224

Days on market

🌊X

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

Principal & interest$7,585
Property taxes$247
Home insurance (est.)$687

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

  1. Status: Active
    Oct 20, 2025
  2. Listed$1,800,000
    Oct 20, 2025
  3. 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

ElementaryCDillard Street ElemGreatSchools ↗
MiddleBLakeview MiddleGreatSchools ↗
High SchoolAWest Orange HighGreatSchools ↗

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

RoomLevelDimensions
Family RoomFirst
Dining RoomFirst
Living RoomFirst
KitchenFirst
Primary BedroomFirst
Bedroom 2First
Bedroom 3First

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 riskFEMA Zone XPanel 12095C0205H

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.

More homes like this

MLS GRID

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.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA