205 SURPRISE DRIVE
Winter Garden, FL 34787
$1,200,000
Welcome to Winter Garden, which has been ranked by Money Magazine "Best Places To Live In America" and is a finalist for Hallmark Channel's 2026 "Merriest Christmas Towns" Contest.
This exceptional property in the heart of the 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.
Priced to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development.
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. A large shed, rated as a detached garage, provides additional space for a workshop or equipment storage. There is ample room for all your recreational ...
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Listing Courtesy of: RE/MAX PRIME PROPERTIES
407-347-4512
| Listing Id: | O6365188 |
|---|---|
| List Price: | $1,200,000 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Active |
| Bedrooms Total: | 4 |
| Bathrooms Full: | 2 |
| Bathrooms Half: | 1 |
| Living Area: | 2,171 |
| Tax Annual Amount: | $3,406 |
| Lot Size Square Feet: | 32,697 |
| Lot Size Acres: | 0.75 |
| Architectural Style: | Custom |
| Waterfront?: | No |
| City: | Winter Garden |
| County Or Parish: | Orange |
| Subdivision Name: | Winter Garden Shores Rep |
| Postal Code: | 34787 |
| Year Built: | 1950 |
| Appliances: | Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 3 |
| Building Area Source: | Public Records |
| Building Area Total: | 2819 |
| Building Area Units: | Square Feet |
| Direction Faces: | Northwest |
| Foundation Details: | Block, Crawlspace |
| Construction Materials: | Block |
| Cooling: | Central Air |
| Fireplace Features: | Family Room, Wood Burning |
| Directions: | From HWY 50 and Dillard St in Winter Garden. Head North on Dillard St to Right on Surprise Dr. House is on the corner. |
| Elementary School: | Dillard Street Elem |
| Exterior Features: | Fire Pit, Garden, Private Mailbox, Storage |
| Fencing: | Fenced |
| Flooring: | Ceramic Tile, Wood |
| Furnished: | Unfurnished |
| Garage Spaces: | 2 |
| Garage?: | Yes |
| Heating: | Central, Electric |
| High School: | West Orange High |
| 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 |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Features: | Corner Lot, City Limits, Landscaped, Oversized Lot, Paved |
| Lot Size Acres: | 0.75 |
| Postal Code Plus4: | 2334 |
| Middle Or Junior School: | Lakeview Middle |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| Other Structures: | Shed(s) |
| Original List Price: | $1,300,000 |
| Other Equipment: | Fire Pit, Irrigation Equipment |
| Parcel Number: | 14-22-27-9392-01-330 |
| Patio And Porch Features: | Covered, Front Porch, Patio |
| Pool Features: | Heated, In Ground, Pool Sweep, Salt Water |
| Stories Total: | 1 |
| Township: | 22 |
| Road Surface Type: | Paved |
| Roof: | Shingle |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2024 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Utilities: | BB/HS Internet Available, Cable Available, Electricity Connected, Public, Water Connected |
| Water Source: | None |
| Public Survey Range: | 27 |
| Public Survey Section: | 14 |
| Zoning: | R-1 |
| Possession: | Close Of Escrow |
| Vegetation: | Fruit Trees, Mature Landscaping, Oak Trees, Trees/Landscaped |
| Window Features: | Blinds |
| Additional Rooms: | Attic, Den/Library/Office |
| Alternate Key Folio Num: | 272214939201330 |
| Available For Lease Yn: | Yes |
| Building Area Total Srch Sq M: | 261.89 |
| Calculated List Price By Calcula: | 552.74 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6365188?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6365188?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2021-09-24 |
| Flood Zone Panel: | 12095C0205H |
| Green Verification Count: | 0 |
| Homestead Yn: | Yes |
| Lease Restrictions Yn: | No |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 201.69 |
| Lot Size Square Meters: | 3038 |
| Minimum Lease: | No Minimum |
| Realtor Info: | As-Is, Sign |
| Room Count: | 8 |
| Sdeo yn: | No |
| Total Acreage: | 1/2 to less than 1 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-347-4512 |
| Originating System Name : | Stellar MLS |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2025-12-01 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
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Property Last Updated: October 21, 2026 07:42 AM - ET
