Oakland Homes for Sale

Oakland Homes for Sale

Welcome to Oakland, Maine – a charming town nestled in the heart of Kennebec County, where picturesque landscapes and a tight-knit community await you. Known for its serene lakes and lush greenery, Oakland offers an idyllic setting for those seeking a peaceful lifestyle while still enjoying the conveniences of modern living. With its rich history and vibrant local culture, this town is an inviting place to call home.

Oakland is situated near the stunning Messalonskee Lake, providing residents with ample opportunities for outdoor recreation, including fishing, boating, and hiking. The town's scenic parks and trails are perfect for family outings or quiet walks, making it an ideal location for nature enthusiasts. The community is also home to various local shops, delicious eateries, and seasonal events that foster a warm sense of belonging.

If you’re considering making Oakland your home, you’re in luck! There are a variety of homes for sale that cater to diverse tastes and budgets. From charming historic houses with character to modern family homes equipped with all the amenities, there’s something for everyone. Whether you’re a first-time homebuyer, looking to downsize, or seeking a vacation retreat, Oakland’s real estate market has options to suit your needs.

Explore the beauty and charm of Oakland, Maine, and discover the perfect home that aligns with your lifestyle. With its welcoming community and stunning natural surroundings, you’ll find that Oakland is not just a place to live, but a place to thrive.

Newest Oakland Homes for Sale

14 Axtell Dr, Oakland
$329,900
3 Beds ⋅ 2 Baths ⋅ 1685763 MLS
Welcome to Axtell Drive. This Raised-Ranch sits on a sprawling corner lot just on the outskirts of town. Close to shopping, Public boat launch on Messalonskee lake, nearby Waterville Country Club, and located conveniently in the Belgrade Lakes region. This home offers privacy in a neighborhood setting. 3 bedrooms and 1.5 baths. Home features include updated kitchen, wood fireplace, hardwood floors. The lower level has a spacious family room and wet bar. 2 Car attached garage is perfect for all of your hobbies. And it is heated for year round comfort. Come see this one today and make your home on Axtell Drive.

14 Axtell Dr, Oakland

Listing courtesy of Summit Real Estate.

25 S Alpine St, Oakland
$314,000
3 Beds ⋅ 1 Baths ⋅ 1685209 MLS
Do not miss out on this truly beautiful home! This 3-bedroom home is the perfect blend of comfort and convenience. Escape the hustle and bustle and relax on the glassed-in porch. Cozy up with your morning coffee, read a book while watching the deer and birds against a backdrop of gorgeous foliage this time of year. This well-maintained 3 bedroom raised ranch is designed for easy efficient living. Conveniently located close to schools and downtown area and within a mile of the Oakland public boat launch where you can kayak, canoe, boat, swim and enjoy a picnic at the park or enjoy the summer concert series. For all the outdoor enthusiasts you can access the Messalonskee stream hiking trails and ATV trails that are less than a mile away. After enjoying the outdoors maybe grab a coffee at the local coffee shop. Inside you will find a cozy open layout of main floor living space which has been recently renovated with new hardwood floors, barn doors, closet doors and a renovated bathroom with walk-in shower. The master bedroom is spacious and sunny with the new barn door entry. The heat pump creates efficient heat for winter and cooler months while keeping it crisp and cool in the hot summer months. The partially finished dry basement can be converted into more living space, let your imagination run wild with possibilities. Outside you have plenty of parking an oversized heated garage allowing for 2 vehicles. There is a large awning attached to garage for those sunny days where you may want to do some outdoor entertaining. The mature perennials and fruit trees border most of the property and the backyard is just big enough to enjoy the view but not require much maintenance. Do not miss the opportunity to own a move-in ready home with all the conveniences of living close to town. Easy low maintenance living close to schools, shopping, downtown coffee shop and eateries, hiking, Oakland waterfront park, and I-95 access.

25 S Alpine St, Oakland

Listing courtesy of EXP Realty.

20 W Vick Avenue Unit 2, Oakland
$1,627,000
4 Beds ⋅ 4 Baths ⋅ O6451301 MLS
Pre-Construction. To be built. Experience custom living at its finest in this beautifully crafted J&J Building home, ideally located in the heart of charming Oakland. Offering 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this home combines thoughtful design with modern appeal. The primary suite is conveniently located on the main floor, providing a private retreat. Enjoy Florida’s year-round sunshine and entertain with ease in the outdoor summer kitchen, perfect for gathering with family and friends. Situated directly across from Speer Park which features pickle ball, a tennis court and a basketball court. Located just moments from Lake Apopka, the West Orand Trail, three miles to downtown Winter Garden, and steps from the charm of downtown Oakland, this home offers a unique blend of outdoor recreation, small-town character, and custom craftsmanship. Don’t miss the opportunity to make this exceptional property your own!

20 W Vick Avenue Unit 2, Oakland

Listing courtesy of ALL REAL ESTATE & INVESTMENTS. 407-917-8206
20 W Vick Avenue Unit 1, Oakland
$1,645,000
4 Beds ⋅ 4 Baths ⋅ O6451262 MLS
Under Construction. Discover the perfect blend of custom craftsmanship, modern style, and small-town charm in this beautifully designed J&J Building home. Featuring 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this distinctive residence offers a thoughtfully designed layout with the primary suite conveniently located on the second floor. Sleek vinyl windows add a contemporary touch, while the summer kitchen creates the perfect setting for outdoor entertaining and enjoying Florida living year-round. Ideally situated across from Speer Park where you can enjoy an active lifestyle featuring pickleball, tennis, and basketball courts. Just up the street from Lake Apopka, the West Orange Trail, three miles from downtown Winter Garden, and right next to charming downtown Oakland, this home offers a wonderful opportunity to enjoy the beauty of nature and the appeal of a welcoming community, all close to home. Experience the best of custom living in a location that truly stands out!

20 W Vick Avenue Unit 1, Oakland

Listing courtesy of ALL REAL ESTATE & INVESTMENTS. 407-917-8206
23 Fieldstone Dr, Oakland
$379,900
3 Beds ⋅ 3 Baths ⋅ 1684845 MLS
Welcome to 23 Fieldstone Drive! Nestled on a peaceful dead-end street in the highly desirable Fieldstone Landing's 55+ community(there is still availability for ownership if you are under 55), this meticulously maintained three- bedroom, 2.5 bath Ranch offers the perfect blend of comfort, privacy, and convenience. Situated on a spacious lot surrounded by well-maintained homes, and bordering the woods, this property provides a quiet, private setting. Start your morning with a cup of coffee in the cozy four-season sunroom, the perfect spot to relax and enjoy the peaceful surroundings. The open- concept kitchen, dining, and living area features vaulted ceilings and radiant heat, creating a bright, inviting space ideal for both everyday living and entertaining. One of the home's standout features is the primary en-suite addition completed in 2021. This private retreat offers plenty of room to unwind, with a comfortable sitting area perfect for watching TV or enjoying a good book, a spacious walk-in closet, and a full bathroom. This thoughtfully designed space also offers excellent potential for multigenerational living or anyone seeking a little extra privacy. Two generously sized bedrooms, a full bathroom, and a convenient half bath provide plenty of room for family and guests. Two recently installed heat pumps provide efficient heating and cooling options throughout the seasons. You will also appreciate the attached garage with direct entry into the home and plenty of additional storage space. Enjoy the best of both worlds with peaceful surroundings and easy access to shopping, restaurants, hospitals, lakes, golf courses, and I-95, all just minutes away. On Demand Generator for peace of mind if you lose power. Schedule a showing today!

23 Fieldstone Dr, Oakland

Listing courtesy of Integrity Homes Real Estate Group, PC.

10 Bacon St, Oakland
$229,000
4 Beds ⋅ 2 Baths ⋅ 1684809 MLS
Intown Oakland home located at the end of a dead end street on a pretty waterfront lot right on Messalonskee Stream! THIS HOME MAY NOT QUALIFY FOR ALL TYPES OF FINANCING DUE TO ITS CONDITION. This home is a fixer upper but has so much potential. Features a modern kitchen with bar area, wood floors and a breezeway to a 2 car garage, (Garage roof does have holes in it and needs extensive repairs), four nice bedrooms up with a 1/2 bath, first floor sunroom and extra room off kitchen. Back deck overlooks beautiful Messalonskee Stream. Priced way below new Oakland tax value.

10 Bacon St, Oakland

Listing courtesy of Century 21 Nason Realty.

29 Sacha Ln, Oakland
$299,000
3 Beds ⋅ 1 Baths ⋅ 1684151 MLS
Welcome to this well-maintained 3-bedroom, 1-bath home tucked away at the end of a quiet dead-end street! Situated on over an acre of land, this property offers a wonderful combination of privacy, convenience, and outdoor space. Whether you're looking to purchase your first home, build equity, or simplify with one-level living, this property has plenty to offer. Beautiful landscaping welcomes you at the front of the home, while the spacious, private backyard provides the perfect setting for entertaining, yard games, gardening, or simply enjoying the outdoors. A freshly sealed driveway adds to the home's curb appeal, while the usable basement offers additional storage space. An on-site shed provides convenient storage for lawn equipment, tools, and seasonal items. Conveniently located just minutes from Colby College, Interstate 95, and local recreational opportunities, this home offers a peaceful setting without sacrificing accessibility. Located in a tax-friendly community, this property is a wonderful opportunity to enjoy comfortable living with room to make it your own. Schedule your private showing today!

29 Sacha Ln, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

36 Fairfield St, Oakland
$329,000
4 Beds ⋅ 1 Baths ⋅ 1684048 MLS
Beautifully situated in a residential neighborhood,this inviting 4-bedroom home offers comfort, charm, & convenience, just minutes from local shops and town amenities. Inside,you'll find a spacious living room,separate dining room,& gorgeous hardwood floors throughout. Cozy pellet fireplace insert adds warmth and ambiance,creating the perfect setting for relaxing evenings.Property also features a one-car garage and a large,fenced-in backyard offering exceptional privacy,mature landscaping,and plenty of room to enjoy the outdoors.Delight in the seasonal beauty of a wolf apple tree,fragrant lilacs,ornamental Chinese lanterns,and a stunning burning bush.A wonderful blend of classic charm,comfortable living,and a private outdoor retreat!

36 Fairfield St, Oakland

Listing courtesy of Portside Real Estate Group.

25 Gifford Pl, Oakland
$695,000
2 Beds ⋅ 2 Baths ⋅ 1684015 MLS
Experience the pinnacle of Maine living with this rare, year-round retreat on the shores of Messalonskee Lake. This isn't just a home; it's a lifestyle package that combines a masterfully renovated residence and lake living. Step into a bright, open-concept sanctuary designed for effortless one-floor living and the possibilty to finish the full basement or attic, with finished stair access. The interior radiates warmth with charming tongue-and-groove pine and expansive windows that frame breathtaking suset lake views. At the heart of the home is a newly upgraded chef's kitchen, featuring sleek stainless steel appliances & gorgeous butcher block countertops. The primary suite offers a modern en-suite bath and direct access to the outside, while new flooring, updated windows, and high-efficiency heat pumps ensure comfort in every season. With two spacious garages, you'll have plenty of room for vehicles, boats, & snowmobiles. Outside, 100 feet of private lake frontage serves as your playground. Whether you're swimming, kayaking, or fishing, the waters of Messalonskee Lake are just steps from your door. Tucked away in a peaceful setting yet located just minutes from the amenities of Oakland and Waterville and easy access to I-95, this property offers the perfect balance of secluded lake life and modern convenience. Don't miss this once-in-a-lifetime opportunity to own a piece of Maine's Belgrade Lakes region.

25 Gifford Pl, Oakland

Listing courtesy of Portside Real Estate Group.

87 Summer St, Oakland
$199,900
2 Beds ⋅ 2 Baths ⋅ 1682536 MLS
Have you been looking for an affordable, updated home with the convenience of one-level living? This Oakland home could be just what you've been waiting for! Step inside to an updated kitchen with newer appliances and plenty of cabinet space to keep everything organized. Just off the kitchen, the spacious living room offers plenty of room to get comfortable and unwind after a long day. The two good-sized bedrooms are located on opposite ends of the home for added privacy. One has an attached half bath, while the other offers generous closet space and a full bathroom right next door. Newer flooring throughout gives the home a fresh, welcoming feel, and the laundry area off the kitchen keeps everyday living convenient. An enclosed porch gives you another spot to relax, enjoy your morning coffee, or settle in with a good book. Outside, there's plenty to appreciate, too! The yard offers room for gardening, outdoor activities, or a cookout with friends. A paved driveway, large two-car garage, and separate storage shed give you plenty of space for parking, tools, and outdoor gear. Located on a quiet road in desirable Oakland, you're just a half mile from Messalonskee Lake's public boat launch and beach, with easy access to the highway and downtown Waterville. Whether you're buying your first home, looking to downsize, or simply ready for the ease of one-level living, this one is worth a look. Come see it before it's gone!

87 Summer St, Oakland

Listing courtesy of Real Broker.

100 Mather Smith Drive, Oakland
$600,000
3 Beds ⋅ 2 Baths ⋅ O6443938 MLS
A vaulted central living space carries the eye from the front dining room through an island kitchen to glass doors opening onto a garden-framed patio, giving this single-story Oakland home a natural indoor-outdoor rhythm. The kitchen serves as the everyday hub, with an expansive island, breakfast-bar seating, abundant cabinetry and clear sightlines that keep meal preparation connected to the main gathering area. Just beyond the living room, the open-air patio is arranged beneath pergola-style shade and surrounded by planted beds, creating an inviting place for morning coffee, outdoor meals or a quiet evening beneath the trees. The split-bedroom plan adds practical separation, positioning the primary suite apart from two secondary bedrooms and a full hall bath. Multiple windows and a tray ceiling shape the primary bedroom, while its en suite bath includes dual sinks, a separate tub and shower and a walk-in closet. Ceramic tile extends through the main living areas, kitchen and bathrooms, with carpet in the bedrooms and an interior laundry area supporting an easy daily routine. Set on a 0.28-acre corner lot with no HOA, the property combines open lawn, mature landscaping and room to enjoy the outdoors, while an attached two-car garage and broad driveway add useful parking and storage. Located in a golf cart-friendly community, you’ll enjoy easy access to downtown Winter Garden’s shops, restaurants and local events, along with the nearby West Orange Trail for walking and biking. This Oakland location offers a relaxed residential setting with convenient access to everything that makes the Winter Garden area so enjoyable.

100 Mather Smith Drive, Oakland

Listing courtesy of KELLER WILLIAMS CLASSIC. murraycoleman@kw.com
56 Heritage Rd, Oakland
$439,000
3 Beds ⋅ 2 Baths ⋅ 1681541 MLS
Well-cared for home in desirable Oakland neighborhood. Home comes with a beautiful common lot to Messalonskee Lake just a short walk away! Path to the water front is right across the street! Features open floor plan & lovely kitchen with center island done in 2010 and all appliances remain. Separate dining area & spacious living room with a propane stove. Updated first floor full bath with tile floors too! Lower level features a family room, 3rd bedroom and another full bath. Home has a full-house generator. The common lake front lot is an association, the street is public. All this plus a lovely private back yard & deck off the dining room to enjoy! Don't miss this special home!

56 Heritage Rd, Oakland

Listing courtesy of Century 21 Nason Realty.

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