Oakland Homes for Sale between $1,000,000 to $1,500,000

Oakland Homes for Sale between $1,000,000 to $1,500,000

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Oakland Homes for Sale Between $1,000,000 to $1,500,000

$1,299,000
1656690 MLS
Exceptional Commercial and Residential Investment Opportunity in Prime Oakland Location! Looking for the perfect space to launch or grow your business, add to your portfolio, or live on site while you work? This rare offering includes both 113 and 121 High Street in Oakland, presenting a unique blend of commercial functionality and residential comfort. At 121 High Street, you'll find a 57x53 heated commercial garage, fully equipped with a lift, tools, and half bath, ideal for trades, storage, or auto work. A second 29x25 garage, additional outbuildings, and a separate office space provide even more versatility. There are three RV hookups, a fenced garden, and fruit bearing plum, apple, and blueberry trees. The 3.68 acre lot offers potential for future development, such as a mobile home park or tiny home community where affordable housing is much needed in the desirable Oakland area. A never used junkyard permit can also transfer with the property. All just minutes from downtown Oakland and the public boat launch at Messalonskee Lake, and under 10 minutes to Waterville's colleges, hospital, and airport. Next door, 113 High Street features an updated home with over 2,700 square feet of finished space. It includes a sleek kitchen with black granite countertops, modern bathrooms with a tiled shower, a spacious family room, and a cozy den with a built-in bar. The layout is ideal for adding bedrooms or converting part of the home into a business office. The basement offers additional space, and the attached garage includes a rear office. Outside, enjoy the stamped concrete patio and well maintained backyard on 0.50 acres. Whether you're an investor, entrepreneur, or buyer seeking a versatile live/work setup, this unique opportunity checks all the boxes!

113 & 121 High St, Oakland

Listing courtesy of Real Broker.

$1,500,000
1626329 MLS
Don't miss out on this one-of-a-kind commercial opportunity! This brand new self-storage business is an investor's dream, boasting 65 units, durable metal construction, and a web-based management system for easy operation. With excellent high occupancy rates and low running expenses, this is a venture that promises strong returns. Conveniently positioned in the heart of Oakland, this business is close to Waterville, Thomas and Colby colleges, and the picturesque Messalonskee Lake, making this facility a preferred choice for students, faculty, and lake house owners needing additional storage space. The package also includes a tastefully remodeled 3-bedroom, 1-bath ranch home that can be further utilized as an extra rental income source, an office space or simply as a convenient residence for maintaining a perfect work-life balance. Come explore the potential of this unique commercial proposition today! Prospective buyers must sign an NDA and present proof of funds to receive financials.

36-38 Summer St, Oakland

Listing courtesy of Harcourts Waterfront & Fine Properties. charlene@harcourtswfp.com
$1,299,000
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.

$1,125,000
4 Beds ⋅ 3 Baths ⋅ G5110973 MLS
SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. 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
$1,250,000
6 Beds ⋅ 8 Baths ⋅ O6362142 MLS
PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland

Listing courtesy of OAKSTRAND REALTY. 888-912-5258
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