205 SURPRISE DRIVE WINTER GARDEN, FL 34787

update time: 02/25/2026 18:01:38

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.

From HWY 50 and Dillard St in Winter Garden. Head North on Dillard St to Right on Surprise Dr. House is on the corner.

Property Details

Nearby Properties

Single Family Residence Active

660 OLD BARTOW LAKE WALES ROAD BARTOW, FL 33830

3 Beds0/2Baths3,244sqft2019 built

$889,000.00

Townhouse Active

648 ORANGE BELT LOOP WINTER GARDEN, FL 34787

3 Beds1/2Baths2,359sqft2018 built

$499,990.00

Condominium Active

6311 NEWTOWN CIRCLE UNIT 11B2 TAMPA, FL 33615

2 Beds1/2Baths1,260sqft1979 built

$155,000.00

Single Family Residence Active

241 N DILLARD STREET WINTER GARDEN, FL 34787

3 Beds0/3Baths4,671sqft1953 built

$1,499,999.00

Condominium Active

3711 W IOWA AVENUE UNIT 214 TAMPA, FL 33611

2 Beds0/2Baths910sqft1990 built

$199,000.00

Single Family Residence Active

146 4TH AVENUE NE UNIT 600 ST PETERSBURG, FL 33701

5 Beds1/6Baths7,457sqft2015 built

$7,950,000.00

Single Family Residence Active

312 SILVERDALE AVENUE WINTER GARDEN, FL 34787

3 Beds0/2Baths2,562sqft2007 built

$559,900.00

Single Family Residence Active

125 BURNS ROAD TERRA CEIA, FL 34250

4 Beds0/4Baths4,750sqft2020 built

$1,750,000.00

Townhouse Active

4911 N NEBRASKA AVENUE TAMPA, FL 33603

3 Beds1/3Baths2,663sqft2021 built

$575,000.00

Single Family Residence Active

238 N MAIN STREET WINTER GARDEN, FL 34787

3 Beds0/2Baths1,087sqft1950 built

$600,000.00

Single Family Residence Active

441 COURTLEA OAKS BOULEVARD WINTER GARDEN, FL 34787

5 Beds1/4Baths4,870sqft2000 built

$1,199,900.00

Single Family Residence Active

652 N JACKSON STREET EAGLE LAKE, FL 33839

2 Beds0/1Baths648sqft1957 built

$165,000.00

Single Family Residence Active

328 BAYSIDE AVENUE WINTER GARDEN, FL 34787

3 Beds0/2Baths1,731sqft1986 built

$445,000.00

Condominium Active

6323 NEWTOWN CIRCLE UNIT 23A1 TAMPA, FL 33615

3 Beds1/2Baths2,012sqft1979 built

$159,000.00

Single Family Residence Active

107 TRADITIONS DRIVE WINTER GARDEN, FL 34787

3 Beds0/2Baths2,314sqft1999 built

$474,975.00

Single Family Residence Active

5811 MARINER STREET TAMPA, FL 33609

5 Beds1/4Baths6,672sqft2017 built

$3,990,000.00

Single Family Residence Active

512 GARDEN HEIGHTS DRIVE WINTER GARDEN, FL 34787

4 Beds0/2Baths2,399sqft1974 built

$585,000.00

Single Family Residence Active

1005 CHASE DRIVE WINTER GARDEN, FL 34787

4 Beds0/3Baths2,971sqft2005 built

$644,000.00

Single Family Residence Active

123 S WIGGINS ROAD PLANT CITY, FL 33566

4 Beds1/2Baths2,816sqft2007 built

$950,000.00

Single Family Residence Active

1075 CHASE DRIVE WINTER GARDEN, FL 34787

4 Beds0/2Baths2,125sqft2015 built

$625,000.00