241 Dillard Street, WINTER GARDEN, FL 34787
Request More Information
  • All fields are required.
  • MLS#: O6353975 ( Residential )
  • Street Address: 241 Dillard Street
  • Viewed: 80
  • Price: $1,800,000
  • Price sqft: $385
  • Waterfront: No
  • Year Built: 1953
  • Bldg sqft: 4671
  • Bedrooms: 3
  • Total Baths: 3
  • Full Baths: 2
  • 1/2 Baths: 1
  • Garage / Parking Spaces: 3
  • Days On Market: 48
  • Additional Information
  • Geolocation: 28.569 / -81.5833
  • County: ORANGE
  • City: WINTER GARDEN
  • Zipcode: 34787
  • Subdivision: J L Dillard Sub 3
  • Elementary School: Dillard Street Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High
  • Provided by: HOMEVEST REALTY
  • Contact: Erica Diaz
  • 407-897-5400
  • mfrmls
  • DMCA Notice
  • 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 Floridas 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 youll 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 youll always be reminded that youre 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 propertys 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 youre 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 Floridas most beloved communities. Opportunities like this simply dont come around twice. Come see for yourself why this remarkable downtown retreat isnt just a home its a legacy waiting to be continued.
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-

  •   Monthly -
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Courtyard, French Doors, Garden, Lighting, Sidewalk, Storage
  • Flooring: Carpet, Wood
  • Living Area: 3507.00
  • Roof: Shingle
Land Information
  • Lot Features: Corner Lot, City Limits, In County, Landscaped, Level, Oversized Lot, Sidewalk, Paved
School Information
  • High School: West Orange High
  • Middle School: Lakeview Middle
  • School Elementary: Dillard Street Elem
Garage and Parking
  • Garage Spaces: 0.00
  • Open Parking Spaces: 0.00
  • Parking Features: Covered, Driveway, Garage Faces Side
Eco-Communities
  • Water Source: Public
Utilities
  • Carport Spaces: 3.00
  • Cooling: Central Air
  • Heating: Central, Electric
  • Pets Allowed: Yes
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Water Connected
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2024
Other Features
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer
  • Country: US
  • 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
  • Legal Description: J L DILLARD SUB NO 3 R/36 LOTS 1 & 2
  • Levels: One
  • Area Major: 34787 - Winter Garden/Oakland
  • Occupant Type: Owner
  • Parcel Number: 27-22-14-2088-00-010
  • Style: Traditional
  • Views: 80
  • Zoning Code: R-2
Similar Properties

Details for 16548 Raven Rock Place, WINTER GARDEN, FL 34787
$1,699,900.00 ($202.32 / sqft )

16548 Raven Rock Place Virtual Tour More Like This

Please note that property visits will only be confirmed upon receipt of proof of funds or a pre qualification letter. All visits will be guided by the listing agent and must be requested at least 24 h

  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 8402 sqft
  1. MLSID: S5134920
  2. Provided by AGENT TRUST REALTY CORPORATION
  3. Contact Norca Serrano Mendoza
  4. mfrmls
  5. DMCA Notice
Details for 15680 Panther Lake Drive, WINTER GARDEN, FL 34787
$2,000,000.00 ($310.56 / sqft )

15680 Panther Lake Drive Virtual Tour Green Listing More Like This

Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an enviro

  1. Bedrooms: 5
  2. Baths: 6
  3. Approx. 6440 sqft
  1. MLSID: O6210445
  2. Provided by KELLER WILLIAMS CLASSIC
  3. Contact Christina Cannon
  4. mfrmls
  5. DMCA Notice
Details for 1149 Prado Lane Drive, OAKLAND, FL 34787
$1,975,000.00 ($334.12 / sqft )

1149 Prado Lane Drive Virtual Tour New Construction More Like This

Pre Construction. To be built. Welcome to the Clementine Floorplan by Element Home Builders A Stunning New Home in Oakland's Premier Community! Discover your dream home with the Clementine Floorpl

  1. Bedrooms: 5
  2. Baths: 6
  3. Approx. 5911 sqft
  1. MLSID: O6295799
  2. Provided by REGENCY REAL ESTATE LLC
  3. Contact Blaine Dooley
  4. mfrmls
  5. DMCA Notice
Details for 166 Hammock Preserve Loop, WINTER GARDEN, FL 34787
$1,675,000.00 ($317.06 / sqft )

166 Hammock Preserve Loop Virtual Tour New Construction More Like This

Under Construction. UPDATE: Ahead of schedule with an estimated completion is FEB 2026. Please see attached package for full renderings and finishes. 166 Hammock Preserve Loop offers one of the finest

  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 5283 sqft
  1. MLSID: O6283425
  2. Provided by CORCORAN PREMIER REALTY
  3. Contact A.J. Lash
  4. mfrmls
  5. DMCA Notice
Details for 1238 Water Maple Drive, OAKLAND, FL 34787
$2,150,000.00 ($394.79 / sqft )

1238 Water Maple Drive Virtual Tour New Construction More Like This

Pre Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12 f

  1. Bedrooms: 5
  2. Baths: 6
  3. Approx. 5446 sqft
  1. MLSID: O6296225
  2. Provided by REGENCY REAL ESTATE LLC
  3. Contact Heather Spirazza
  4. mfrmls
  5. DMCA Notice
Details for 1146 Prado Lane, OAKLAND, FL 34787
$2,130,760.00 ($432.73 / sqft )

1146 Prado Lane New Construction More Like This

Pre Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992 sq

  1. Bedrooms: 5
  2. Baths: 6
  3. Approx. 4924 sqft
  1. MLSID: O6359354
  2. Provided by REGENCY REAL ESTATE LLC
  3. Contact Heather Spirazza
  4. mfrmls
  5. DMCA Notice
Details for 9940 Black Bear Lane, WINTER GARDEN, FL 34787
$2,050,000.00 ($433.95 / sqft )

9940 Black Bear Lane Virtual Tour New Construction More Like This

Pre Construction. To be built. This Custom Single Story Modern Farmhouse by Lionshead Homes is a showstopper! Set on a serene 5 acre private oasis. Plenty of space for farm animals or just enjoy the o

  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 4724 sqft
  4. Approx. 5.00 acres
  1. MLSID: O6309917
  2. Provided by HAMLIN REALTY
  3. Contact Edward Guerrette LLC
  4. mfrmls
  5. DMCA Notice
Details for 7766 Minutemen Loop, WINTER GARDEN, FL 34787
$1,824,888.00 ($315.89 / sqft )

7766 Minutemen Loop Virtual Tour More Like This

Experience the Best of Florida Living! Enjoy Floridas natural beauty from the comfort of your own home with breathtaking sunset views over a serene lake. Whether you're watching the full moon rise or

  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 5777 sqft
  4. Approx. 2.41 acres
  1. MLSID: O6328707
  2. Provided by FL SUNSHINE STATE REALTY
  3. Contact Mae Wang
  4. mfrmls
  5. DMCA Notice
Details for 9072 Bradleigh Drive, WINTER GARDEN, FL 34787
$1,795,000.00 ($314.47 / sqft )

9072 Bradleigh Drive Virtual Tour More Like This

Experience the very best in true lakefront living where every detail has been carefully designed for comfort, style, and enjoyment. Located in the heart of Winter Garden within the highly desirable La

  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 5708 sqft
  4. Approx. 1.25 acres
  1. MLSID: O6354407
  2. Provided by RE/MAX PRIME PROPERTIES
  3. Contact Ronald Ziolkowski
  4. mfrmls
  5. DMCA Notice
Details for 15783 Tangerine Dream Court, WINTER GARDEN, FL 34787
$2,150,000.00 ($325.71 / sqft )

15783 Tangerine Dream Court Virtual Tour More Like This

LUXURY ISLAND HOME IN POPULAR GATED COMMUNITY. Experience modern lakefront luxury in Emerald Point, an exclusive gated island of only 28 homes within the desirable Hickory Hammock community, offering

  1. Bedrooms: 5
  2. Baths: 6
  3. Approx. 6601 sqft
  1. MLSID: O6360410
  2. Provided by CLOCK TOWER REALTY
  3. Contact Denise Gregorie
  4. mfrmls
  5. DMCA Notice