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$1,300,000 - 205 Surprise Drive, WINTER GARDEN

3
Bedrooms
3
Baths
2,171
SQ. Feet
0.75
Acres

Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four-lot parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. Two of the four lots are currently vacant, offering potential to subdivide, expand, or build. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.

Essential Information

  • MLS® #:
    O6365188
  • Price:
    $1,300,000
  • Bedrooms:
    3
  • Bathrooms:
    3.00
  • Full Baths:
    2
  • Half Baths:
    1
  • Square Footage:
    2,171
  • Acres:
    0.75
  • Year Built:
    1950
  • Type:
    Residential
  • Sub-Type:
    Single Family Residence
  • Style:
    Custom
  • Status:
    Active

Community Information

  • Address:
    205 Surprise Drive
  • Area:
    Winter Garden/Oakland
  • Subdivision:
    WINTER GARDEN SHORES REP
  • City:
    WINTER GARDEN
  • County:
    Orange
  • State:
    FL
  • Zip Code:
    34787

Amenities

  • # of Garages:
    2
  • Has Pool:
    Yes

Interior

  • Interior Features:
    Built-in Features, High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Thermostat, Window Treatments
  • Appliances:
    Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Heating:
    Central, Electric
  • Cooling:
    Central Air
  • Fireplace:
    Yes
  • Fireplaces:
    Family Room, Wood Burning
  • # of Stories:
    1

Exterior

  • Exterior Features:
    Fire Pit, Garden, Private Mailbox, Storage
  • Lot Description:
    Corner Lot, City Limits, Landscaped, Oversized Lot, Paved
  • Roof:
    Shingle
  • Foundation:
    Block, Crawlspace

School Information

  • Elementary:
    Dillard Street Elem
  • Middle:
    Lakeview Middle
  • High:
    West Orange High

Additional Information

  • Days on Market:
    47
  • Zoning:
    R-1

Listing Details

  • Listing Office:
    Re/max Prime Properties

Listing information courtesy of Re/max Prime Properties.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on January 20th, 2026 at 3:19am EST.