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.
Listing updated: 2026-10-04T18:05:06.720Z
Listed by Realtor: Alaina Dimare
Listed by office: COAST TO COAST REAL ESTATE PRO
Source: Stellar MLS
Property Details
Listing Id: G5110973
Price: $999,000
Property Size:2,469 ft2
Property Lot Size:0 ft2
Rooms: 3
Bedrooms: 4
Bathrooms: 2.5
Bathrooms Full: 2
Bathrooms Half: 1
Modification Timestamp: 2026-10-06T18:03:20.988Z
Building Area Total: 3953
Construction Materials: Block
Cooling: Central Air
CoveredSpaces: 3
CumulativeDaysOnMarket: 175
DaysOnMarket: 175
DirectionFaces: West
ElementarySchool: Tildenville Elem
FireplaceFeatures: Wood Burning
Flooring: Laminate, Luxury Vinyl
FoundationDetails: Slab
Furnished: Unfurnished
GarageSpaces: 3
HighSchool: West Orange High
Laundry Features: Laundry Room
Levels: Two
List AOR: Orlando Regional
List Agent AOR: Lake and Sumter
List Agent Email: RealtorAlaina1@gmail.com
List Agent Full Name: Alaina Dimare
List Agent MlsId: 261232297
ListOfficeMlsId: 261022051
List Office Name: COAST TO COAST REAL ESTATE PRO
ListOfficePhone: 352-296-8930
Listing Terms: Cash, Conventional, FHA, Owner May Carry, VA Loan
Living Area Source: Public Records
Lot Features: Cleared
LotSizeArea: 17015
LotSizeSquareFeet: 17015
MLS Area Major: 34760 - Oakland
MiddleOrJuniorSchool: Lakeview Middle
MlsStatus: Active
ModificationTimestamp: 2026-10-04T18:05:06.720Z
OnMarketDate: 2026-04-14
Originating System Name: Stellar MLS
Other Structures: Shed(s), Workshop
Ownership: Fee Simple
Parcel Number: 202227610834000
Parking Features: Boat, Garage Door Opener, Golf Cart Parking, Guest, Off Street
Pool Features: In Ground, Salt Water, Screen Enclosure
All listings featuring of Stellar MLS are provided by Stellar MLS. This information is not verified for authenticity or accuracy and is not guaranteed. 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 MLS.