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.
Property Details
Price:
$598,000
MLS #:
O6402692
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKLAND SHORES
Neighborhood:
34760oakland
Listed Date:
Apr 28, 2026
Finished Sq Ft:
1,571
Total Sq Ft:
2,118
Lot Size:
12,405 sqft / 0.28 acres (approx)
Year Built:
1997
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Electric
Interior Features
Thermostat
Laundry Features
Other
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Block, Concrete, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Other
Garage Spaces
2
Roof
Shingle
Financial
Tax Year
2025
Taxes
$3,603
Map
Community
- Address100 MATHER SMITH DRIVE OAKLAND FL
- SubdivisionOAKLAND SHORES
- CityOAKLAND
- CountyOrange
- Zip Code34760
Subdivisions in OAKLAND
- BRILEY FARM
- GROVE AT THE HARVEST DISTRICT
- HULL ISLAND ESTATES FIRST ADD
- JOHNS LANDING
- JOHNS LANDING PH 01 44/47
- JOHNS LANDING PH 02 48 138
- JOHNS LANDING PHASE 1
- LONGLEAF
- LONGLEAF AT OAKLAND
- LONGLEAF/OAKLAND
- LONGLEAF/OAKLAND REP
- OAKLAND PARK
- OAKLAND PK UN 7 NORTH
- OAKLAND TOWN
- OAKLAND TRAILS
- OAKLAND TRAILS PH 1
- OAKLAND TRLS PH 1
- OAKLAND TRLS PH 2
- RYAN COURT
- THE GROVE AT OAKLAND
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in OAKLAND as of Apr 29, 2026
29
Single Family Listed
71
Avg DOM
346
Avg $ / SqFt
$1,094,585
Avg List Price
Property Summary
- Located in the OAKLAND SHORES subdivision, 100 MATHER SMITH DRIVE OAKLAND FL is a Single Family for sale in OAKLAND, FL, 34760. It is listed for $598,000 and features 3 beds, 2 baths, and has approximately 1,571 square feet of living space, and was originally constructed in 1997. The current price per square foot is $381. The average price per square foot for Single Family listings in OAKLAND is $346. The average listing price for Single Family in OAKLAND is $1,094,585. To schedule a showing of MLS#o6402692 at 100 MATHER SMITH DRIVE in OAKLAND, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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Courtesy of MARK SPAIN REAL ESTATE. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 100 MATHER SMITH DRIVE
OAKLAND, FL