241 N DILLARD STREET, Winter Garden, FL 34787

• 3 beds |
• 3 baths |
• 3,507 sqft

Property Description

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. 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. 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.

Listing Status:

Active

Date Added:

October 20, 2025 at 05:00AM

Listing Office:

HOMEVEST REALTY : 407-897-5400

Listing Agent:

Erica Diaz : 407-897-5400

MLS ID:

O6353975

Interior

• General: Ceiling Fans(s)Crown MoldingEat-in KitchenHigh CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanStone Counters
• Rooms: Bonus RoomInside Utility
• Appliances: Built-In OvenCooktopDishwasherDisposalDryerGas Water HeaterMicrowaveRange HoodRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: CarpetWood
• A/C: Central Air
• Heating: CentralElectric
• Fireplace: OtherWood BurningFireplace

Exterior

• General: CourtyardFrench DoorsGardenLightingSidewalkStorage
• Style: Traditional
• Other Structures: PorchRear PorchPatio
• Parking: CoveredDrivewayGarage Faces Side

Construction

• Roofing: Shingle
• General: BlockConcreteOneSlab

Location

• Road/Access: Paved
• Originating MLS: mfrmls
• County: Orange

Lot

• Zoning: R-2J L DILLARD SUB NO 3 R/36 LOTS 1 & 227-22-14-2088-00-010

Utilities

• Utilities: BB/HS Internet AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedPhone AvailableSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: mfrmls
• Ownership: Fee Simple

This listing courtesy of Erica Diaz, HOMEVEST REALTY