$1,300,000
3 Bed
3 Bath
2,171 Sqft
0.75 Acre Lot

205 Surprise Dr, Winter Garden, Florida 34787

  • Residential Property Type
  • 2,171 Sqft Square Footage
  • 1950 Year Built
Property Description

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.

Basic Details
Residential
For Sale
O6365188
$1,300,000
3
3
1
2,171 Sqft
1950
0.75 Acre
Active
2
Single Family Residence
: Shingle
Features
: Heated, In Ground, Pool Sweep, Salt Water
: Central, Electric
: Central Air
: Fenced
: Wood Burning, Family Room
: Covered, Front Porch, Patio
: Garden, Private Mailbox, Storage, Fire Pit
: Ceramic Tile, Wood
: High Ceilings, Primary Bedroom Main Floor, Thermostat, Window Treatments, Living Room/Dining Room Combo, Solid Wood Cabinets, Built-in Features
: Washer Hookup, Electric Dryer Hookup, In Garage
1
: Public Sewer
: Public, Cable Available, Electricity Connected, BB/HS Internet Available, Water Connected
: Blinds
: Custom
Appliances
: Dishwasher, Microwave, Dryer, Refrigerator, Washer, Cooktop
Address Map
US
FL
Orange
Winter Garden
WINTER GARDEN SHORES REP
34787
SURPRISE
205
DRIVE
W82° 25' 1.8''
N28° 34' 27.7''
Northwest
From HWY 50 and Dillard St in Winter Garden. Head North on Dillard St to Right on Surprise Dr. House is on the corner.
34787 - Winter Garden/Oakland
R-1
Neighborhood
Dillard Street Elem
West Orange High
Lakeview Middle
Additional Info
RE/MAX PRIME PROPERTIES
Alison Scorsone
$0
$0
Additional Information
: Block
: Crawlspace, Block
2
: One
: Paved, Corner Lot, Landscaped, Oversized Lot, City Limits
2025-12-04
1
https://www.propertypanorama.com/instaview/stellar/O6365188
: None
1
2819
Financial
3406.12
Listing Information
261082000
261012018
Cash,Conventional
Active
2025-12-05T14:25:10Z
Stellar
: None
2025-12-04T23:19:50Z
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Contact Agent
Contact Us
407-615-0866