$1,200,000
205 Surprise Drive
Winter Garden, FL 34787
Listing updated: June 7, 2026 at 2:05 PM ET
Listing courtesy of Re/Max Prime Properties · Alison Scorsone · MLS #O6365188 · Active · 407-347-4512Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Local Insight
At $553/sqft for a 1950s home on three-quarters of an acre with a private pool, you're paying a premium for the lot size and amenities in a fast-growing area—but that price is steep for a 73-year-old house that will likely need significant updates beyond cosmetics. The no-HOA designation and X flood zone are genuine pluses for this corner of Winter Garden Shores, though you'll want a thorough inspection given the age, and factor in potential foundation or structural issues common to homes built in that era on former citrus land. The location offers good schools and sits in one of Florida's fastest-growing CDPs, which could support resale value, but the true test is whether the bones justify the cost or if you're mainly buying the pool and lot.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history144 days on market
- Status: ActiveJun 2, 2026
- Listed$1,300,000Dec 4, 2025
- Price reduced$1,200,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 144
- Subdivision
- Winter Garden Shores Rep
- County
- Orange
- Year built
- 1950
- Living area
- 2,171 sq ft
- Price/sq ft
- $553
- Building area
- 2,819 sq ft (Public Records)
- Lot size
- 32,697 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X (12095C0205H)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $3,406 (2024)
- Parcel #
- 14-22-27-9392-01-330
- Zoning
- R-1
- MLS #
- O6365188
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Ceramic Tile, Wood
- Appliances
- Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer
- Interior features
- Built-in Features, High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Thermostat, Window Treatments
- Laundry
- Electric Dryer Hookup, In Garage, Washer Hookup
- Stories / Levels
- One
- Direction faces
- Northwest
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
Exterior & Construction
- Exterior features
- Fire Pit, Garden, Private Mailbox, Storage
- Construction materials
- Block
- Roof
- Shingle
- Foundation
- Block, Crawlspace
- Pool
- Private pool
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- None
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Public, Water Connected
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | 15x11 |
| Bedroom 2 | First | 15x13 |
| Bedroom 3 | First | |
| Breezeway | First | 23x15 |
| Dining Room | First | 21x12 |
| Living Room | First | 21x15 |
| Kitchen | First | |
| Office | First | 15x14 |
Listing Details
- Listing date
- 2025-12-01
- On market date
- 2025-12-04
- Original list price
- $1,300,000
- Occupant type
- Vacant
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-06-02
- Tax legal description
- REPLAT OF WINTER GARDEN SHORES M/76 LOTS131 THRU 134
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of June 7, 2026 at 2:05 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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