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Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys"”this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator"”truly a chef's dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you'll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available"”and this one checks every box. Bring your golf cart and don't miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let's make it yours.
| DAYS ON MARKET | 25 | LAST UPDATED | 5/6/2026 |
|---|---|---|---|
| TRACT | OAKLAND TOWN | YEAR BUILT | 2000 |
| COMMUNITY | 34760 - Oakland | GARAGE SPACES | 3.0 |
| COUNTY | Orange | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Tildenville Elem |
|---|---|
| Jr. High School | Lakeview Middle |
| High School | West Orange High |
| PRICE HISTORY | |
| Prior to May 6, '26 | $1,295,000 |
|---|---|
| May 6, '26 - Today | $1,195,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Disposal, Microwave, Range, Refrigerator |
| AREA | 34760 - Oakland |
| CONSTRUCTION | Block |
| EXTERIOR | Lighting |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central |
| LOT | 0.39 acre(s) |
| LOT DESCRIPTION | Cleared |
| PARKING | Boat, Garage Door Opener, Guest, Off Street, Attached |
| POOL | Yes |
| POOL DESCRIPTION | In Ground, Salt Water, Screen Enclosure, Private |
| SEWER | Septic Tank |
| STORIES | 2 |
| SUBDIVISION | OAKLAND TOWN |
| TAXES | 10744.77 |
| UTILITIES | Cable Available |
| VIEW | Yes |
| VIEW DESCRIPTION | Trees/Woods |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Alaina Dimare, COAST TO COAST REAL ESTATE PRO, 352-296-8930
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 5/8/26 6:14 PM PDT.
This IDX solution is (c) Diverse Solutions 2026.