205 SURPRISE DRIVE WINTER GARDEN FL 34787 MLS #O6365188

205 SURPRISE DRIVE
WINTER GARDEN, FL, 34787
$1,200,000
4 Beds
2.5 Baths
2,171 SqFt
0.75 Acres
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MLS #O6365188 image #0
Under contract-accepting backup offers. PRICE ADJUSTED to reflect recent appraisal, this four-lot parcel presents immediate value- with two vacant lots ready for expansion, additional income potential, or future development. 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.

Property Details

Price:
$1,200,000
MLS #:
O6365188
Status:
Pending
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINTER GARDEN SHORES REP
Neighborhood:
34787wintergardenoakland
Listed Date:
Dec 4, 2025
Finished Sq Ft:
2,171
Total Sq Ft:
2,819
Lot Size:
32,697 sqft / 0.75 acres (approx)
Year Built:
1950
CustomPoolPrimary Bedroom Main Floor34787 – Winter Garden/oakland34787wintergardenoaklandWinter Garden Shores RepDillard Street ElemLakeview MiddleWest Orange HighNo Minimum

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Schools

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

Interior

Appliances
Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Thermostat, Window Treatments
Laundry Features
Electric Dryer Hookup, In Garage, Washer Hookup
Levels
One

Exterior

Architectural Style
Custom
Attached Garage YN
1
Construction Materials
Block
Covered Spaces
2
Direction Faces
Northwest
Exterior Features
Fire Pit, Garden, Irrigation System, Private Mailbox, Storage
Fencing
Fenced
Garage Spaces
2
Lot Features
Corner Lot, City Lot, Landscaped, Oversized Lot
Other Structures
Shed(s)
Patio And Porch Features
Covered, Front Porch, Patio
Roof
Shingle
Window Features
Blinds

Financial

Tax Year
2024
Taxes
$3,406

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Apr 29, 2026
789
Single Family Listed
108
Avg DOM
280
Avg $ / SqFt
$744,443
Avg List Price

Property Summary

    Located in the WINTER GARDEN SHORES REP subdivision, 205 SURPRISE DRIVE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $1,200,000 and features 4 beds, 3 baths, and has approximately 2,171 square feet of living space, and was originally constructed in 1950. The current price per square foot is $553. The average price per square foot for Single Family listings in WINTER GARDEN is $280. The average listing price for Single Family in WINTER GARDEN is $744,443. To schedule a showing of MLS#o6365188 at 205 SURPRISE DRIVE in WINTER GARDEN, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.

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205 SURPRISE DRIVE
WINTER GARDEN, FL
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