Nestled in the historic enclave of Oakland, 100 Mather Smith Drive is a premier retreat balancing modern convenience with small-town Florida charm. This meticulously maintained 3-bedroom, 2-bathroom residence sits on a generous quarter-acre corner lot, offering rare privacy with the massive benefit of no annual association fees or HOA oversight. The true crown jewel is the location—you are literally steps away from private backyard access to the world-renowned West Orange Trail. Imagine daily strolls or bike rides through scenic oak canopies, starting directly from your own back gate. Inside, the 1,571 sqft floor plan is bathed in natural light, flowing seamlessly to an oversized covered patio—perfect for morning coffee or weekend gatherings. Minutes from downtown Winter Garden’s dining and top-rated schools, this home features a brand-new shingle roof and a clean slate for personalization. It’s a unique opportunity for outdoor enthusiasts seeking a lifestyle of activity and tranquility.
- Built in 1997
- 2 garage spaces
- $380.65/sqft
- Lot size: 12,405 sqft
- 2 days on market
- Directions: Head west on West Colonial Drive (State Road 50) and turn north onto Tubb Street. Follow Tubb Street to East Gulley Avenue and turn right. Take the next left onto North Arlington Street, then turn right onto Mather Smith Drive. The home will be on your right at the corner.
- County: Orange
- Geo subdivision: OAKLAND SHORES
Nearby Schools
Tildenville 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!

José Freitas

- Source: Stellar MLS
- MLS #: O6402692
Listing updated: April 28, 2026 at 7:48PM
Listing provided by: Danny Laniado, MARK SPAIN REAL ESTATE
Last checked 1 day ago
Listing provided by: Danny Laniado, MARK SPAIN REAL ESTATE
Last checked 1 day ago
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