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

$1,495,000
4 Beds ⋅ 4 Baths ⋅ O6440357 MLS
FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking in the peaceful surroundings and views of the West Orange Trail just beyond your front door. Step inside to soaring spaces, abundant natural light, and architectural details that immediately make an impression. A grand staircase leads to a striking bridge-style balcony overlooking the family room, while a beautiful brick gas-burning fireplace anchors the living space and creates a warm, inviting centerpiece for gathering and entertaining. Designed with both everyday living and flexibility in mind, the spacious floor plan features a formal dining room, dedicated office, bonus room, and enclosed sunroom offering even more space to relax and enjoy the Florida lifestyle year-round. A generously sized walk-in closet provides exceptional storage, while thoughtful features such as a central vacuum system add everyday convenience. Roof Replacement in 2025 and HVAC replacement in 2022 add peace of mind for years to come. Located within Oakland's golf cart district, this home offers extra garage space for your golf cart, bikes, and moreWhether you're enjoying coffee on the porch swing, relaxing beside the fireplace, or simply taking in the peaceful small-town atmosphere, this home offers a wonderful combination of space, character, and location in sought-after Oakland. Come experience the charm and lifestyle that make this community such a special place to call home!

137 Petris Avenue, Oakland

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021
$798,000
5 Beds ⋅ 2 Baths ⋅ 1679215 MLS
East Pond is where a lifetime of memories is built, and at 20 & 21 Bass Cove, those memories begin just steps from the water. This 5-bedroom waterfront home on East Pond offers a rare, grandfathered shoreline setting, with the main home sitting less than 15 feet from the water, approximately 336 feet of private shoreline and 3.5 surveyed acres. Today's shoreland zoning would not allow a home to be built this close to the shoreline, making this setting truly special. The approximately 2,608 sq ft main home features four first-floor bedrooms and a full bath, along with a large family room and inviting living room anchored by a dramatic stone fireplace. Relaxing, playing games, enjoying time together around the fire after a day on the lake, or sharing dinner and stories on the expansive waterfront deck as the sun sets across East Pond. Upstairs, a massive 700+ sq ft open-concept room with a full bath, cathedral ceilings and skylights provides exceptional space for entertaining, recreation or guests. Here, the water becomes part of everyday life. Listen to loons at dusk, watch bald eagles and ospreys overhead, enjoy sandy-bottom swimming, or launch a kayak, paddleboard or boat right from your own shoreline. A separate approximately 600 sq ft guest cabin creates its own lakeside experience, featuring an open-concept room with cathedral ceiling, skylights, electric heat, plus a screened porch, covered porch and separate dock (currently meter removed). A standing seam metal roof adds durability to the main home. Dock, swim platform and mooring are included. Owned by the same family since 1939, the original camp was rebuilt in 1962, with the second floor added in 1994. This unique waterfront home on East Pond brings together generations of history, two buildings, substantial acreage and an extraordinary connection to the water. In the winter enjoy some of the best skiing with 1.5 hour to Sugarloaf and other ski resorts.

20 & 21 Bass Cv, Oakland

Listing courtesy of OWN REAL ESTATE. kimhawkes@ownrealestate.me
$398,000
4 Beds ⋅ 2 Baths ⋅ 1678794 MLS
Make the most of summer with a stunning outdoor retreat centered around an impressive 18' x 36' in-ground pool with a new liner and a new pool shed. Surrounded by a spacious new stamped concrete patio designed for relaxing, grilling, outdoor dining, and gathering with friends. The fenced in pool and generous patio provides plenty of room to create your own private outdoor oasis. Inside, this inviting home offers thoughtful updates and flexible living space, including an updated eat-in kitchen with newer cabinetry and granite countertops, plus a separate dining room. Both full bathrooms have been updated with stylish tile showers, updated flooring, and modern fixtures. The first-floor full bath is conveniently located off the kitchen and includes laundry for added everyday ease. When cooler weather arrives, settle into the living room, watch the snow fall over the skylights, and enjoy the warmth and ambiance of the propane stove. Upstairs, you'll find four bedrooms and a full bath, along with a flexible room featuring a vaulted ceiling and skylights that could make a wonderful family room. A separate back building offers valuable space for recreational gear, equipment, or storage, with garage doors on both ends providing convenient pull-through access. From sunny afternoons by the pool to cozy winter evenings indoors, this home offers spaces to enjoy throughout every season, with convenient access to schools, shopping, and dining.

96 Oak Hill Dr, Oakland

Listing courtesy of OWN REAL ESTATE. kimhawkes@ownrealestate.me
$438,000
3 Beds ⋅ 2 Baths ⋅ 1678162 MLS
Looking for low-maintenance, one-floor living with an incredible outdoor space for entertaining? Built in 2021 and beautifully maintained, this move-in ready 3-bedroom, 2-bath home combines a thoughtfully designed floor plan, extensive recent improvements, and a private backyard setting made for gathering, relaxing, and enjoying Maine's natural beauty. An attached two-car garage adds everyday convenience, while the home's excellent separation of space creates privacy throughout. The primary suite features a spacious bedroom, full bath, and walk-in closet, while two additional bedrooms and a second full bath with a walk-in shower are located on the opposite side of the home. A spacious walk-out basement provides endless opportunity for additional living space, whether you envision a family room, home office, fitness area, hobby space, or additional room to spread out. Since 2023, the current owner has completed numerous upgrades, including a beautiful new front deck, professional landscaping, a new storage shed, whole-house generator, gutters with leaf guard protection, and two energy-efficient heat pumps for year-round comfort. Outside, the private backyard patio and beautifully landscaped grounds create an amazing setting for entertaining, summer cookouts, quiet evenings, or simply watching the abundant local wildlife. The generous outdoor space provides plenty of room to gather with friends and enjoy the peaceful country surroundings. Set in a quiet neighborhood yet convenient to everyday amenities, this like-new home offers easy access to the Belgrade Lakes Region, nearby golf, shopping, restaurants, recreation, and downtown Waterville. With a desirable single-level layout, quality improvements, inviting outdoor living spaces, a spacious walk-out basement, and so many major upgrades already completed, this exceptional property offers an easy transition into comfortable Maine living.

12 Gleason Farm Rd, Oakland

Listing courtesy of OWN REAL ESTATE. kimhawkes@ownrealestate.me
$289,900
4 Beds ⋅ 2 Baths ⋅ 1678117 MLS
Some houses ask you to move in. This one asks you to move forward, into the life you've been imagining, on your own terms. Set on a surveyed 0.39-acre corner lot in Oakland, this classic New England farmhouse gives you 2,484± sq. ft., 4 bedrooms, 2 full baths, and something rare: 22± feet of owned frontage on Messalonskee Lake, Not shared access, yours, running the parcel to the water. This is your chance to combine a true renovation project with genuine Maine lakefront ownership, at a price point waterfront rarely offers. Step inside and you can feel what's waiting: spacious rooms, hardwood floors, tall windows, substantial trim, a traditional staircase, built-ins, a decorative mantel, a pantry, and first-floor laundry. Every detail is a starting point, not a finished thought. The attached one-car garage/barn adds storage, workspace, and even more room to make this place your own. This is not a turnkey home, offered as-is as part of an estate, it will require substantial renovation. But if you're the kind of buyer who'd rather create than compromise, who's been searching for a farmhouse fixer-upper, a restoration project, an investment opportunity, or simply an affordable way onto Messalonskee Lake, this is the one worth seeing in person. Public water and sewer. An in-town Oakland location near shopping, recreation, and the public boat landing. Restore the farmhouse. Rework the rooms. Bring back the character. Keep the lake. Make it unmistakably yours.

2 Old Belgrade Ave, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

$449,900
4 Beds ⋅ 2 Baths ⋅ 1677714 MLS
Welcome Home! This well-maintained 4 bedroom, 2 full bath Maine farmhouse, beautifully situated on 10 acres of peaceful, private land. Thoughtfully cared for and updated over the years, this home blends classic farmhouse charm with the comforts and conveniences today's buyers are looking for. The beautifully updated kitchen offers a welcoming space for everyday living and entertaining, while the first-floor laundry adds valuable convenience. A true Maine must-have, the spacious mud room provides the perfect spot to kick off boots, hang coats, and keep life organized through every season. Outside, enjoy your own private retreat with an in-ground pool, perfect for summer gatherings, relaxing, and making memories. With 10 acres to explore, there's plenty of room for gardening, recreation, animals, or simply enjoying the peace and privacy of country living. A wonderful combination of character, updates, usable acreage, and outdoor enjoyment, this farmhouse is ready to welcome its next owners home.

241 Belgrade Rd, Oakland

Listing courtesy of Portside Real Estate Group.

$389,000
3 Beds ⋅ 2 Baths ⋅ 1677699 MLS
Welcome to this charming three-bedroom, two-bathroom farmhouse set on 17 beautifully manicured acres in Oakland. Combining classic farmhouse character with comfortable living spaces and exceptional outdoor amenities, this property provides a wonderful setting to enjoy the best of Maine. A gorgeous wraparound front porch welcomes you into the home and provides the perfect place to relax and take in the peaceful surroundings. The porch flows naturally to a beautiful patio area overlooking the in-ground swimming pool which is the perfect place to entertain your guests. Inside, the home features a warm and welcoming kitchen complete with an island and fireplace. A formal dining area sits just off the kitchen and features built-in cabinets and access to the back deck. The first floor also features a spacious living room. There is also a very convenient mudroom which provides a very practical entry space from the two-car, attached garage. Only minutes from I-95, this home an easy communte to the Waterville, Skowhegan, and Augusta areas. Here you will enjoy privacy and that country feel despite being only a few minutes from all the local amenities. Call today for more information.

334 Town Farm Rd, Oakland

Listing courtesy of Whittemore's Real Estate.

$415,000
3 Beds ⋅ 2 Baths ⋅ O6430972 MLS
Virtually Staged. PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY! NOTE: to add extra storage, a (large shed) can be added onto the property within the purchase of the home. NO HOA! Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers 1,170 square feet of modern living space on a 0.09-acre homesite. The open-concept floor plan features luxury vinyl plank flooring throughout the main living areas and bedrooms, with porcelain tile flooring in both bathrooms for added durability and style. The kitchen is equipped with quartz countertops, modern cabinetry, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas, making it ideal for everyday living and entertaining. Contemporary lighting, designer fixtures, and quality finishes can be found throughout the home. The primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms offer flexibility for family, guests, or a home office. Additional features include an indoor laundry area, energy-efficient windows, modern exterior finishes, and a paver driveway. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, parks, major highways, and local attractions, this move-in-ready home offers the opportunity to enjoy low-maintenance living in the desirable Town of Oakland. Don't miss your chance to own this newly built home in one of Central Florida's most sought-after communities.

521 W Herriott Avenue, Oakland

Listing courtesy of REAL BROKER, LLC. 855-450-0442
$225,000
2 Beds ⋅ 1 Baths ⋅ 1674155 MLS
Exceptional value in a desirable neighborhood near the beautiful Belgrade Lakes! This beautifully updated 1-2 bedroom, 1,056-square- foot home sits on a quiet 0.23-acre lot. Since 2018, this property has undergone massive high-ticket infrastructure improvements, giving a future owner total peace of mind. Major updates include custom hickory cabinets in the kitchen and bathroom, modern appliances, fresh flooring, updated plumbing and electrical 2018), a leach field (2019), and a drilled well (2021). Enjoy a peaceful setting with easy access to outdoor recreation and local amenities. Please note: To respect the privacy of the occupant, initial viewings are conducted via virtual tour. In-person showings will be scheduled upon an accepted offer.

520 Smithfield Rd, Oakland

Listing courtesy of Sprague & Curtis Real Estate. lori@spragueandcurtis.com
$330,000
3 Beds ⋅ 2 Baths ⋅ 1674140 MLS
Well-maintained 3-bedroom, 2-bath ranch offering comfortable one-level living on a spacious .93-acre lot in a quiet neighborhood. Designed with accessibility in mind, the home features handicap-accessible doorways and a wide hallway for added convenience. The updated kitchen boasts beautiful hickory cabinets, Corian countertops, and ample workspace for everyday living and entertaining. The primary suite includes a recently renovated full bath with a walk-in shower. A pellet stove and heat pump provide efficient, year-round comfort. Step outside to enjoy the large composite deck overlooking the private backyard--perfect for relaxing or hosting family and friends. The expansive unfinished basement offers abundant storage and excellent potential for a workshop, home gym, etc. With modern updates, accessibility features, and a peaceful setting, this move-in-ready home is a wonderful opportunity to enjoy the best of Oakland and surrounding amenities.

32 Mayland St, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

$3,295,000
6 Beds ⋅ 7 Baths ⋅ O6429415 MLS
Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.

312 Briley Avenue, Oakland

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155
$239,000
3 Beds ⋅ 2 Baths ⋅ 1673925 MLS
Solid and well-maintained 3-bedroom, 2-bath home offering approximately 1,500 square feet of living space on a generous 0.50-acre lot in Oakland. Recent improvements include a newer septic system (2024), boiler, propane monitor heater, and a detached two-car garage with a recently replaced shingle roof. The home's metal roof adds to its long-term durability, while the functional layout provides flexibility for a variety of living arrangements. Conveniently located with easy access to local amenities and I-95, this property offers an excellent opportunity for an owner-occupant or investor alike. Whether you're looking for your next home or an income-producing property, this one is well worth a look.

132 Washington St, Oakland

Listing courtesy of Keller Williams Realty. nick@nickisgro.com
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