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.
- Built in 1950
- 2 garage spaces
- $598.80/sqft
- Lot size: 32,697 sqft
- 9 days on market
- 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.
- County: Orange
- Geo subdivision: WINTER GARDEN SHORES REP
Nearby Schools
Dillard Street Elem
Lakeview Middle
West Orange High
Features
Interior
Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Financial
Lease Information
Tax, Legal & Financing
Let's get in touch!
Let's get in touch!

Niles Harrison Pfeiffer
Central Florida REALTOR®
- Source: Stellar MLS
- MLS #: O6365188
Listing updated: December 13, 2025 at 7:09PM
Listing provided by: Alison Scorsone, RE/MAX PRIME PROPERTIES
Last checked 0 seconds ago
Listing provided by: Alison Scorsone, RE/MAX PRIME PROPERTIES
Last checked 0 seconds ago
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