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241 N Dillard Street

Winter Garden, FL 34787
  • $1,800,000
  • STATUS: Active
  • ON SITE: 50 Days
  • MLS #: O6353975
UPDATED: 53 min ago
$1,800,000
  • 3
    BEDS
  • 0.64
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 3,507
    SQFT
  • $513
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1953
County:

School Information

Elementary School:
Middle School:
High School:

Description

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 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 23 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.

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© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2025-12-10T14:46:06.357.
www.ashley-wallace.com/homes/169080692
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241 N Dillard Street Winter Garden, FL 34787

  • Price: $1,800,000
  • Status: Active
  • On Site: 50 Days
  • Updated: 53 min ago
  • MLS #: O6353975
3
Beds
2
Baths
1
½ Baths
0.64
Acres
3,507
SQFT
$513
$/SQFT
1953
Built
Neighborhood:
J L Dillard Sub 3
County:
Orange
Area:
Winter Garden/Oakland
Elementary School:
Dillard Street Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Property Description
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 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 23 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.
Exterior Features

Architectural Style Traditional Carport Spaces 3 Carport Yn Yes Construction Materials BlockConcrete Covered Spaces 3 Direction Faces West Exterior Features CourtyardFrench DoorsGardenIrrigation SystemLightingSidewalkStorage Foundation Details Slab Lot Features Corner LotCity LotIn CountyLandscapedLevelOversized LotSidewalk Open Parking YN Yes Parking Features CoveredDrivewayGarage Faces Side Patio And Porch Features PatioPorchRear Porch Pool Private Yn No Road Frontage Type Street Paved Road Surface Type Paved Roof Shingle Water Access Yn No Water Extras Yn No Water View Yn No Waterfront Feet Total 0 Waterfront Yn No

Interior Features

Additional Rooms Bonus RoomInside Utility Appliances Built-In OvenCooktopDishwasherDisposalDryerGas Water HeaterMicrowaveRange HoodRefrigeratorWasher Building Area Total 4671 Cooling Central Air Cooling YN Yes Fireplace Features Other RoomWood Burning Fireplace Yn Yes Flooring CarpetHardwood Heating CentralElectric Heating YN Yes Interior Features Ceiling Fan(s)Crown MoldingEating Space In KitchenHigh CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanStone Counters Laundry Features InsideLaundry Room Levels One Rooms Living Room Family Room Dining Room Primary Bedroom (Built-in Closet) Kitchen Bedroom 2 (Built-in Closet) Bedroom 3 (Built-in Closet) Sewer Public Sewer Water Source Public

Property Features

Additional Lease Restrictions Buyer to verify with the city Approval Process Buyer to verify with the city Association Approval Required Yn No Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn No Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN Yes Listing Terms CashConventionalVA Loan Minimum Lease 8-12 Months New Construction Yn No Ownership Fee Simple Pet Restrictions Buyer to verify with the city Pets Allowed Yes Property Sub Type Single Family Residence Realtor Info As-IsSign Senior Community Yn No Special Listing Conditions None Tax Annual Amount 2959 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedPhone AvailableSewer ConnectedWater Connected Yrs Of Owner Prior To Leasing Re No Zoning R-2


Listing information © 2025 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of HOMEVEST REALTY: 407-897-5400.



© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2025-12-10T14:46:06.357.
 
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