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$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
$1,249,000
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.

$325,000
1660162 MLS
Blake Island on Messalonskee Lake offers a rare and extraordinary opportunity to own a private seven-acre wooded sanctuary equipped with modern infrastructure. Already prepared for your vision, the island features an underwater electric power cable, a dug well, and two septic systems, making it ready for a dream cottage or a refined seasonal camp. A scenic perimeter trail system provides a one-of-a-kind hiking experience with exceptional southerly views down the lake, while the expansive acreage ensures ultimate privacy. Messalonskee Lake is renowned for its high water quality and world-class sport fishing, and accessing your retreat is seamless with a private dock, carport, and parking for two vehicles on the mainland. Whether you are looking for a secluded getaway or a unique development project, this legacy property offers the perfect balance.

52 Blake Is, Oakland

Listing courtesy of Portside Real Estate Group.

$445,000
3 Beds ⋅ 2 Baths ⋅ 1650477 MLS
New construction! Build in process, get under contract in time to make some interior choices! Be the first to live in this new 3 bedroom, 2 bathroom ranch with open concept kitchen/living/dining room, radiant heat and attached heated 2 car garage! In a desirable location close to in town amenities, Waterville Country Club, lakes and I-95 for an easy commute for work and play! Taxes are for the lot only, the full amount is TBD.

Lot 1-12 Jacques, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

$395,000
1656965 MLS
Versatile commercial property currently operating as a printing and embroidery business, offering a flexible layout ideal for a variety of uses. The second floor features a 3-bedroom apartment, currently being utilized by the business. Additionally, the full basement offers additional operating space or storage. This property is perfect for an owner-operator or an investor looking to offset expenses with rental income while running their business.

82 Libby Hill Rd, Oakland

Listing courtesy of Harborview Properties, Inc..

$44,000
1655218 MLS
**Seller will have property surveyed soon!** Discover the perfect blend of privacy and convenience with this beautiful 2.63-acre parcel located on quiet Pinewoods Trail in Oakland. This property offers an ideal opportunity to build your dream home or create a relaxing weekend getaway. A small cleared building site is already in place just off the road, making it easy to start planning your vision right away. Located just under 10 minutes from Waterville and I-95, this property provides quick access to shopping, dining, and commuting routes.

Lot 45-2 Pinewoods, Oakland

Listing courtesy of Hoang Realty.

$399,000
2 Beds ⋅ 2 Baths ⋅ 1662851 MLS
A 1950's cabin has been completely transformed - taken down to the studs and rebuilt with thoughtful craftsmanship and timeless design throughout. Every major system has been replaced; all new electrical, plumbing, insulation, septic, heat pumps, kitchen, finished carpentry, and septic, offering the peace of mind of new construction while maintaining the character. Inside, the kitchen features granite countertops, a stunning stone tile floor, and the perfect ambiance of a woodstove creating a warm and inviting living space. The home offers two spacious bedrooms and two full bathrooms, with a layout ideal for dual primary suites or comfortable guest accommodations. Perfectly situated on Belgrade Road, this property offers convenient access to the highly sought-after Belgrade Lakes Region, the award winning Belgrade Lakes Golf Club, and just 15 minutes to both Waterville and Augusta. Its an ideal location for year round living or a weekend getaway!

203 Belgrade Rd, Oakland

Listing courtesy of Hearth & Key Realty. 2077133144
$1,850,000
5 Beds ⋅ 5 Baths ⋅ 1663344 MLS
This phenomenal home is sitting on over 28 acres w/ horse stalls, riding pens & a stocked trout pond. You'll always have something fun to do here. This gorgeous home offers lots of space, 5-6 bedrooms, & beautiful finishes. Lovely landscaping & white fences. Large garage for 4 cars w/radiant heat, & a pull thru overhead door to the back. Beautiful deck w/ pergola looks out to the back acreage, perfect for watching wildlife. Inside you are greeted w/ a large family room w/ lots of windows. 180x 320 ft riding arena, w/ announcer booth/ tree stand for hunters. The well-appointed kitchen features a stone island, double pantries, & a cozy sunroom off the rear to watch Sunday games or simply to enjoy the gas fireplace. First floor laundry & a beautiful formal living room w/ built in cabinets. First floor primary bedroom w/ a gorgeous en suite bath w/ tile steam shower, soaking tub, & double vanities. Upstairs there is a fantastic family room, perfect for games, a theater, office or workout space & a large bonus room. In the daylight basement is an additional kitchen, full bath w/ laundry, & 3 additional rooms. Stand by generator. This property also features modern barn venue, which could also be used for many other business & activities. Beautiful grounds include a fountain, hardscaping, & lovely gardens. This building has an upscale finish w/ rustic flair. Generous parking in the rear. High ceilings give a spacious feel to the 7,200 sq ft main floor. Next to the main floor is an additional space that includes a kitchen area w/ commercial fridges, a bar area, & multiple bathrooms including a handicap accessible bathroom. Upstairs is a room that was used for a bridal suite, but it could be used as a conference space as well. Outdoor seating under pergolas & garden lights. Beautiful setting for photographs. Separate 5 car garage & mobile home for storage. Generator on site. So many possibilities with this property.

78 98 Hussey Hill Rd, Oakland

Listing courtesy of Sprague & Curtis Real Estate. tyler@spragueandcurtis.com
$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
$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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