About 205 Surprise Drive
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.
Features of 205 Surprise Drive
| MLS® # | O6365188 |
|---|---|
| Price | $1,200,000 |
| Bedrooms | 4 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,171 |
| Acres | 0.75 |
| Year Built | 1950 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Custom |
| Status | Active |
Community Information
| Address | 205 Surprise Drive |
|---|---|
| Area | Winter Garden/Oakland |
| Subdivision | WINTER GARDEN SHORES REP |
| City | WINTER GARDEN |
| County | Orange |
| State | FL |
| Zip Code | 34787-2334 |
Amenities
| # of Garages | 2 |
|---|---|
| Is Waterfront | No |
| Has Pool | Yes |
Interior
| Interior Features | Built-in Features, High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Thermostat, Window Treatments |
|---|---|
| Appliances | Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer |
| Heating | Central, Electric |
| Cooling | Central Air |
| Fireplace | Yes |
| Fireplaces | Family Room, Wood Burning |
| # of Stories | 1 |
Exterior
| Exterior Features | Fire Pit, Garden, Irrigation System, Private Mailbox, Storage |
|---|---|
| Lot Description | Corner Lot, City Lot, Landscaped, Oversized Lot |
| Roof | Shingle |
| Foundation | Block, Crawlspace |
School Information
| Elementary | Dillard Street Elem |
|---|---|
| Middle | Lakeview Middle |
| High | West Orange High |
Additional Information
| Date Listed | December 4th, 2025 |
|---|---|
| Days on Market | 250 |
| Zoning | R-1 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | RE/MAX PRIME PROPERTIES |
|---|