$2,000,0000.22 mi
20 W Crest AvenueWinter Garden, FL, 34787Sold Sep 17, 20265 beds5 baths4,668 sqft
1 / 32
205 Surprise DriveWinter Garden, FL, 34787
4beds
3baths
2,171sqft
Single Family Residence
Built in 1950
$1,200,000
For sale
$1,300,000−$100,000 (8%)Reduced Feb 25, 2026
- Price per sqft
- $553
- Days on market
- 308
- Listed Dec 4, 2025
MLS #O6365188Updated Sep 16, 2026
About this property
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.
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Property details
- Property type
- Single Family Residence
- Street address
- 205 Surprise Drive
- City
- Winter Garden
- State
- FL
- ZIP code
- 34787
- Year built
- 1950
- New construction
- No
- Faces
- Northwest
- Rooms
- 8
- Building stories
- 1
- Living area
- 2,171 sqft
- Total building area
- 2,819 sqft
- Levels
- One
The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDTPrice & sale history
Asking price reduced by $100,000 (7.7%) since first listed.
| Date | Event | Price | Change from previous recorded asking price |
|---|---|---|---|
| Price reducedMLS #O6365188 | $1,200,000Change: −7.7%−$100,000 | −7.7%−$100,000 | |
| Listed for saleMLS #O6365188 | $1,300,000 | Not applicable | |
| SoldMLS #O5400501 | $290,000 | Not applicable | |
| Listed for saleMLS #O5400501 | $290,000 | Not applicable |
History may be incomplete.
Location
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