PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive 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.
This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. 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.
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.
This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. 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:
Active
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
See this Listing
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
- Address205 SURPRISE DRIVE WINTER GARDEN FL
- SubdivisionWINTER GARDEN SHORES REP
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Aug 29, 2026
829
Single Family Listed
112
Avg DOM
279
Avg $ / SqFt
$759,523
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 $279. The average listing price for Single Family in WINTER GARDEN is $759,523. To schedule a showing of MLS#o6365188 at 205 SURPRISE DRIVE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
Similar Listings Nearby
Courtesy of RE/MAX PRIME PROPERTIES. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 205 SURPRISE DRIVE
WINTER GARDEN, FL