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$1,300,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,171 Sq. Ft.
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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.

Full Property Details for 205 Surprise Dr

General

  • Price: $1,300,000
  • Taxes: $3,406 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6365188
  • Updated: 12/5/2025
  • Added to Site: 43 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 8
  • Interior Features: Built-in Features, High Ceilings, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Thermostat, Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Family Room, Wood Burning
  • Appliances: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Electric Dryer Hookup, In Garage, Washer Hookup

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground, Pool Sweep, Salt Water

Exterior

  • Exterior Features: Fire Pit, Garden, Irrigation System, Private Mailbox, Storage
  • Deck/Patio: Covered, Front Porch, Patio
  • Porch/Patio/Deck: Covered, Front Porch, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WINTER GARDEN SHORES REP
  • Driving 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.
  • Direction Faces: Northwest

School Information

  • Elementary School: Dillard Street Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: None
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Public, Water Connected

Structural Information

  • Architectural Info: Custom
  • Architectural Style: Custom
  • Exterior Const.: Block
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: One
  • Square Feet: 2,171
  • Sq. Ft. Source: Public Records
  • Year Built: 1950

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Lot Size (Acres): 0.75
  • Lot Size (Sq. Ft.): 32,697
  • Lot Size: 32697
  • Frontage: Street Paved
  • Street/Road Desc.: Paved
  • Fencing (Description): Fenced

Financial Considerations

  • Tax Amount: $3,406.12
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: REPLAT OF WINTER GARDEN SHORES M/76 LOTS131 THRU 134
  • Flood Zone Info: X
  • APN: 142227939201330
  • Property ID: 142227939201330
  • Block/Lot/Section: 1

Listed by Re/Max Prime Properties

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— 205 Surprise Dr —

  • Re/Max Prime Properties

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 205 Surprise Dr

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.2 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81.4 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 205 Surprise Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/04/2025
Listed
$1,300,000
348.28%
MLS
11/30/2015
Sold
$290,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 205 Surprise Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$3,406
—
$260,730
3%
2024
$3,406
4%
$253,382
3%
2023
$3,279
6%
$246,002
7%
2021
$3,096
-2%
$229,995
-3%
2022
$3,146
2%
$236,895
7%
2021
$3,096
5%
$220,863
2%
2019
$2,942
1%
$215,897
2%
2018
$2,912
14%
$211,871
11%
2017
$2,554
-35%
$190,863
-17%
2016
$3,954
99%
$230,410
52%
2015
$1,989
-1%
$151,453
1%
2014
$2,001
3%
$150,251
1%
2013
$1,949
—
$148,031
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Re/Max Prime Properties

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205 Surprise Drive, Winter Garden, FL 34787 (MLS# O6365188) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 205 Surprise Drive is currently listed for $1,300,000 and was received on December 04, 2025. Want to learn more about 205 Surprise Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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