Primary on Main
Address
205 Surprise Drive, WINTER GARDEN, FL
Price
$ 1,200,000
Property Attributes
- MLS#O6365188
- TypeSingle Family
- Listing Status Active
- CountyOrange
- CityWINTER GARDEN
- AreaWinter Garden/Oakland
- NeighborhoodWINTER GARDEN SHORES REP
- Zip34787
- StyleCustom
- Year Built1950
- Taxes$ 3406
- Price$ 1,200,000
- Bedrooms4
- Full Bathrooms2
- Half Bathrooms1
- Sqr Footage2171
- Lot Size0.75 Acres
Data Source:
Stellar MLS
Property Description
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 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. The 3/4 acre property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. SELLER WILL CONSIDER SUB-DIVIDINGTHE LOTS. 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.
| Elementary School | Middle School | High School |
|---|---|---|
| Dillard Street Elem Elementary School | Lakeview Middle Middle School | West Orange High High School |
| Price History | |
|---|---|
| 12/19/2025 | Listed $1,300,000 |
| 2/25/2026 | 8$1,200,000 |
General Features
| Sewer | Public Sewer |
|---|---|
| Heating | Central,Electric |
| Cooling | Central Air |
| Utilities | BB/HS Internet Available,Cable Available,Electricity Connected,Public,Water Connected |
| Possession | Close Of Escrow |
| Roof | Shingle |
| Appliances | Cooktop,Dishwasher,Dryer,Microwave,Refrigerator,Washer |
| Zoning | R-1 |
| Garage Spaces | 2 |
| Patio/Porch Features | Covered,Front Porch,Patio |
| Architectural Style | Custom |
| Pool Features | Heated,In Ground,Pool Sweep,Salt Water |
| Construction Materials | Block |
| Year Built | 1950 |
| Levels | One |
| Property Subtype | Single Family Residence |
| Tax Year | 2024 |
| Ownership | Fee Simple |
| County | Orange |
| New Construction | false |
| Property Type | Residential |
| Attached Garage | true |
| Subdivision Name | WINTER GARDEN SHORES REP |
| Facing Direction | Northwest |
| Garage Y/N | true |
| Other Structures | Shed(s) |
| Total Rooms | 8 |
| Full Baths | 2 |
| Status | Active |
| 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. |
| High School | West Orange High |
| City | WINTER GARDEN |
| Senior Community Y/N | false |
| MLS Area | 34787 - Winter Garden/Oakland |
| Lot Size Units | Square Feet |
| Lot Size Square Feet | 32697 |
| Carport Y/N | false |
| Listing Terms | Cash,Conventional |
| Elementary School | Dillard Street Elem |
| Land Lease Y/N | false |
| Tax Annual Amount | 3406.12 |
| Middle/Junior High School | Lakeview Middle |
| Additional Parcels Y/N | false |
| Lease Considered Y/N | true |
| Virtual Tour | https://www.propertypanorama.com/instaview/stellar/O6365188 |
| Building Area Units | Square Feet |
| Living Area Units | Square Feet |
| Standard Status | Active |
| Occupancy Type | Vacant |
| Tax Lot | 131 |
| Legal Description | REPLAT OF WINTER GARDEN SHORES M/76 LOTS131 THRU 134 |
| Minimum Lease | No Minimum |
| Water Access Y/N | false |
| Additional Rooms | Attic,Den/Library/Office |
| Water View Y/N | false |
| Flood Zone Code | X |
| In Law Suite YN | false |
| Flood Zone Code X | Yes |
Interior Features
| Interior Amenities | Built-in Features,High Ceilings,Living Room/Dining Room Combo,Primary Bedroom Main Floor,Solid Wood Cabinets,Thermostat,Window Treatments |
|---|---|
| Flooring | Ceramic Tile,Hardwood |
| Furnished Y/N | Unfurnished |
| Fireplace Features | Family Room,Wood Burning |
| Total Stories | 1 |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Window Features | Blinds |
| Fireplace Y/N | true |
| Half Baths | 1 |
| Laundry Features | Electric Dryer Hookup,In Garage,Washer Hookup |
| Total Bedrooms | 4 |
| LivingAreaSource | Public Records |
| Total Baths | 3 |
Exterior Features
| Exterior Amenities | Fire Pit,Garden,Irrigation System,Private Mailbox,Storage |
|---|---|
| Vegetation | Fruit Trees,Mature Landscaping,Oak Trees,Trees/Landscaped |
| Fencing | Fenced |
| Lot Features | Corner Lot,City Lot,Landscaped,Oversized Lot |
| Water Source | None |
| Lot Size Area | 32697 |
| Foundation Details | Block,Crawlspace |
| Building Area Total | 2819 |
| Lot Size Acres | 0.75 |
| Road Surface Type | Paved |
| Private Pool | true |
| Waterfront Y/N | false |
| Covered Spaces | 2 |
| Road Frontage Type | Street Paved |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 34787
Price
Taxes
Year Built
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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Updated on September 19, 2026 6:31 AM UTC
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Data Last Updated: September 19, 2026 7:36 AM UTC
