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$799,999
5 Beds ⋅ 3 Baths ⋅ TB8513260 MLS
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

16 Oakland Pointe Circle, Oakland

Listing courtesy of JACK KELLER INC. 727-586-1497
$594,900
4 Beds ⋅ 3 Baths ⋅ 1663280 MLS
Skip the construction loan and step into a beautifully designed new construction Colonial offering approximately 1,870± square feet of thoughtfully crafted living space. This 4-bedroom, 2.5-bath home blends timeless style with modern functionality, creating the perfect space for everyday living and entertaining. The first floor features a spacious open-concept kitchen and living area centered around a large island, along with a dedicated dining room, convenient utility/laundry room, and half bath. Upstairs, you'll find four generously sized bedrooms including a private primary suite complete with a walk-in closet and full bath with double vanities and a custom shower. This home features quartz countertops, painted cabinetry, and durable click-lock flooring throughout the main living spaces, creating a clean and modern feel from top to bottom. Please note: garage is not included in the offering price. Want to experience the layout in person? This model is available to walk through at our sales center in Chelsea. Reach out today to learn more about the process and timeline to completion.

Lot 15 Autumn, Oakland

Listing courtesy of Summit Real Estate.

$299,900
3 Baths ⋅ 1653128 MLS
Don't miss this in-town **2-unit multi-family property in Oakland** offering strong income potential and added flexibility. Each unit features separate utilities, allowing tenants to pay their own heat and electricity. The property also includes additional office space with potential to be converted into expanded living space for the first-floor unit (buyer to verify permitted uses with local officials). Recent improvements include sewer lines replaced approximately four years ago and Rinnai heaters installed approximately two years ago, providing added efficiency and peace of mind. Conveniently located just minutes from Waterville and close to local amenities, shopping, dining, and services. Whether you are looking to owner-occupy or invest, this property offers opportunity and versatility. Schedule your showing today!

11 Church St, Oakland

Listing courtesy of Keller Williams Realty.

$1,249,000
2 Beds ⋅ 3 Baths ⋅ 1656684 MLS
If you've been searching for a property where you can live comfortably and run your own business right next door, this one of a kind setup in Oakland is worth a look. This offering includes two properties at 113 and 121 High Street and is ideal for contractors, mechanics, tradespeople, or anyone needing both residential space and commercial functionality. At 113 High Street, you'll find a beautifully updated home with over 2900 sqft of finished living space. The kitchen features sleek black granite countertops, the bathrooms are modern with tile finishes, and the layout includes a spacious family room and a cozy den with a built in bar. The floor plan offers flexibility with space to add bedrooms or set up home offices. The basement adds usable square footage, and the attached garage includes a rear office. Outside, enjoy a stamped concrete patio and a well kept backyard perfect for relaxing or entertaining. Next door at 121 High Street is a large commercial space ready for your business. The 57x53 foot heated garage is fully equipped with a lift, tools, and a half bath. This would be perfect for automotive work, construction, trades, or equipment storage. There is also a second 29x25 garage, multiple outbuildings, and a detached office space that gives you even more flexibility. The 4.18 acre lot includes three RV hookups, a fenced garden, and fruit trees including plum, apple, and blueberry. There is plenty of open space to expand or explore future development options such as a mobile home park or tiny home community. A never used junkyard permit is also available to transfer with the property. Located minutes from downtown Oakland and the public boat launch at Messalonskee Lake and less than ten minutes to Waterville's colleges, hospital, and airport, this property offers convenience, space, and endless potential. Whether you are an entrepreneur, Investor or someone ready to run a business from home, this property gives you the best of both worlds!

113 & 121 High St, Oakland

Listing courtesy of Real Broker.

$1,049,000
4 Beds ⋅ 3 Baths ⋅ G5110973 MLS
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.

250 N Walker Street, Oakland

Listing courtesy of COAST TO COAST REAL ESTATE PRO. 352-296-8930
$619,999
4 Beds ⋅ 3 Baths ⋅ O6394442 MLS
NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

38 S Pollard Street, Oakland

Listing courtesy of MS LAND & BUILDING LLC. 407-466-7000

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