WINTER GARDEN, FL 34787 241 N DILLARD STREET

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Presented By: HOMEVEST REALTY with 407-897-5400. - 407-897-5400
  • MLS# O6353975
  • 10/20/2025
  • Request Tour
  • Request Info
Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 3
  • Full/Half Baths • 2 / 1
  • SQFT • 3,507
  • Garage • 1

Home Details

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.
Presented By: HOMEVEST REALTY with 407-897-5400. - 407-897-5400

Interior Features for 241 N DILLARD STREET

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths1
Total Baths3

Other Interior Features

LivingAreaSourceowner
Air Conditioning Y/NYes
Fireplace Featuresother room, wood burning
Fireplace Y/NYes
Flooringcarpet, hardwood
Heating Y/NYes
Interior Amenitiesceiling fan(s), crown molding, eating space in kitchen, high ceilings, kitchen/family room combo, living room/dining room combo, open floorplan, stone counters
Laundry Featuresinside, laundry room

General for 241 N DILLARD STREET

Additional Parcels Y/NNo
Additional Roomsbonus room, inside utility
Appliancesbuilt-in oven, cooktop, dishwasher, disposal, dryer, gas water heater, microwave, range hood, refrigerator, washer
Architectural Styletraditional
Building Area Unitssquare feet
Carport Spaces3
Carport Y/NYes
Citywinter garden
Construction Materialsblock, concrete
Coolingcentral air
Countyorange
Directionshead west on state rte 50 w. turn right onto s dillard st. in 1.2 mi. property will be on the right.
Elementary Schooldillard street elem
Facing Directionwest
Flood Zone Codex
Flood Zone Code XY
Full Baths2
Garage Y/NNo
HOANo
Heatingcentral, electric
High Schoolwest orange high
Land Lease Y/NNo
Lease Considered Y/NYes
Legal Descriptionj l dillard sub no 3 r/36 lots 1 & 2
Levelsone
Listing Termscash, conventional, va loan
Living Area Unitssquare feet
Lot Size Square Feet27988
Lot Size Unitssquare feet
MLS Area34787 - winter garden/oakland
Middle/Junior High Schoollakeview middle
Minimum Lease8-12 months
ModificationTimestamp2025-11-03t16:29:06.050z
New ConstructionNo
Occupancy Typeowner
Ownershipfee simple
Patio/Porch Featurespatio, porch, rear porch
Pets Allowedyes
Property Subtypesingle family residence
Property Typeresidential
Roofshingle
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
Sewerpublic sewer
Standard Statusactive
Statusactive
Subdivision Namej l dillard sub 3
Tax Annual Amount2959
Tax Lot1
Tax Year2024
Total Rooms7
Utilitiesbb/hs internet available, cable connected, electricity connected, natural gas connected, phone available, sewer connected, water connected
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1953
Zoningr-2

Exterior for 241 N DILLARD STREET

Building Area Total4671
Covered Spaces3
Exterior Amenitiescourtyard, french doors, garden, irrigation system, lighting, sidewalk, storage
Foundation Detailsslab
Lot Featurescorner lot, city lot, in county, landscaped, level, oversized lot, sidewalk
Lot Size Acres0.64
Lot Size Area27988
Parking Featurescovered, driveway, garage faces side
Private PoolNo
Road Frontage Typestreet paved
Road Surface Typepaved
Vegetationmature landscaping, oak trees, trees/landscaped
Water Sourcepublic
Waterfront Y/NNo

Additional Details

Price History

Schools

High School West Orange High
Elementary School Dillard Street Elem
Middle School Lakeview Middle

Steven Pugh

Broker Associate | Team Leader
Price $1,800,000
MLS#O6353975
List Date 10/20/2025
Property Type Single Family
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