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189 Ten Lots Rd, Oakland
$299,000
3 Beds ⋅ 2 Baths ⋅ 1685993 MLS
Welcome to 189 Ten Lots Road! This charming 3 bedroom, 1.5 bath Cape is ready to welcome its new owners! Situated on over an acre of land in a desirable rural setting, this property offers a wonderful opportunity to build equity while enjoying the peace and privacy of country living. As you approach the home, you're greeted by a long driveway leading to two attached single bay garages, offering plenty of space for vehicle storage, hobbies or additional storage needs. The level, open lot provides room to enjoy the outdoors, garden or simply take in the surrounding setting. Inside, the first floor features a kitchen that opens to the dining area, creating a functional space for everyday living. A first floor primary bedroom, full bathroom with shower and convenient laundry area make single level living a possibility. Upstairs, you'll find two additional generously sized bedrooms and a half bath, providing flexibility for family, guests, or a home office. With its inviting rural setting, functional layout and opportunity to make it your own, this property offers plenty of potential. Conveniently located near area amenities while still tucked away in a peaceful setting, 189 Ten Lots Road is ready for its next chapter!

189 Ten Lots Rd, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

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. For all the outdoor enthusiasts you can access the Messalonskee stream hiking trails and ATV trails that are less than a mile away. 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 boat launch, 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.

48 Thomasville Rd, Oakland
$159,900
2 Beds ⋅ 1 Baths ⋅ 1683309 MLS
Private lot in Oakland, with a 2 bed 1 bath home. Full basement with a woodstove that can hold up to 3 foot logs. Fruit trees, flowers and wildlife daily. Peaceful and easy living!

48 Thomasville Rd, Oakland

Listing courtesy of Summit Real Estate.

510 Oak St, Oakland
$189,500
3 Beds ⋅ 2 Baths ⋅ 1682772 MLS
Stop paying rent and start building equity. This 1997 double-wide sits on a level, tree-lined lot in Oakland, where property taxes stay reasonable and help keep monthly costs down. The open floor plan connects the kitchen, dining room, and living room. Because the home faces east, the kitchen fills with morning light. The primary bedroom has a walk-in closet and a full bath, with a privacy door separating the shower and toilet from the vanity. A large front deck gives you outdoor space from day one. The back deck needs repair, which is an opportunity to add value with your own work. The home is set on a concrete slab with tie-downs and is within easy reach of Waterville's jobs, shopping, dining, and the arts. It's an affordable first step into ownership and it comes with a cozy woodburning fireplace to top it all off!

510 Oak St, Oakland

Listing courtesy of EXP Realty.

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.

311 Oak St, Oakland
$139,000
3 Beds ⋅ 1 Baths ⋅ 1682248 MLS
Well, maintained...Strong & sturdy. Clean from top to bottom, recently refreshed with new flooring (throughout), paint where needed and upgraded exterior doors - this home is turn-key ready and waiting for you. Earth tone colors and faux knotty pine walls add to the warmth and coziness of this home. The galley kitchen is well established with plenty of counter space, cabinetry and a separate pantry. The designated laundry area provides a convenient washer/dryer nook. A new energy efficient furnace and new hot water heater top off the utilities for efficiency! This 1974 singlewide mobile home sits perfectly on just over two acres of owned land. As the pictures show, this home is well placed on its lot to take advantage of the brilliant sunlight that flows through the entire length of the home in both the morning and the afternoon. Conversely, the back and side yards are lined with shade trees, offering shade and a breeze, for that perfect cooling balance. With the quaint country touches of a wishing well on one end and the forever fun tire swing on the other, this home will be sure to please and warm the heart!

311 Oak St, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

96 Madeline Dr, Oakland
$299,000
4 Beds ⋅ 2 Baths ⋅ 1682100 MLS
With plenty of space inside and out this property offers the opportunity to create the lifestyle you've been looking for. Spacious 4-bedroom, 2-bathroom mobile home on 1.3 acres in a quiet Oakland subdivision. The home features an updated kitchen with a center island and stainless-steel appliances, offering functional and inviting space for cooking and entertaining. A comfortable den offers a little extra space for an office or crafting area. The two-car garage with a workshop, second floor and added attached shed gives the property ample space for vehicles, hobbies and storage. Outside enjoy a large open yard with a deck, that is the perfect spot to relax and enjoy the outdoors. Located on a dead-end street, this property offers a quiet residential setting while still being conveniently located in Oakland. Just minutes from Waterville, local shopping, dining, schools, and easy access to I-95.

96 Madeline Dr, Oakland

Listing courtesy of Lakehome Group Real Estate. info@lakehomegroup.com
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.

30 Oak St Unit 43, Oakland
$95,000
2 Beds ⋅ 2 Baths ⋅ 1681491 MLS
Set at the end of a quiet, dead-end street in a mobile home park in downtown Oakland, this well-maintained double-wide offers a desirable location within the park with neighbors only to one side, and unbuildable land on the neighboring property, creating a more private back yard. Boasting updated appliances, fresh paint, and the addition of a ramp, this home has been carefully maintained by the sellers during their ownership, and reflects their pride of ownership.

30 Oak St Unit 43, Oakland

Listing courtesy of EXP Realty.

41 Mary Ln, Oakland
$325,000
3 Beds ⋅ 2 Baths ⋅ 1681370 MLS
Easy, efficient, and thoughtfully laid out, this single-level home offers comfortable living in a quiet neighborhood close to schools, recreation, and everyday amenities. Whether you're just starting out, looking to simplify, or hoping to enjoy the ease of one-floor living, this home offers a lot to appreciate. Inside, the painted kitchen features warm wood countertops, an island for added prep and gathering space, and an easy flow into the living and dining areas. A pellet stove adds extra warmth and coziness to the living room, while the back porch extends the living space and offers a great spot to relax and enjoy the surroundings. Down the hall, you'll find a dedicated utility and laundry room, a conveniently located half bath, and three bedrooms. One bedroom features its own full bath, creating a comfortable primary bedroom setup with added privacy. With everything you need on one level, an efficient footprint, and a peaceful neighborhood setting close to desirable schools and outdoor recreation, this home offers a simple and comfortable way to settle in and make it your own.

41 Mary Ln, Oakland

Listing courtesy of Portside Real Estate Group.

39 S Greenridge Hts, Oakland
$249,900
3 Beds ⋅ 2 Baths ⋅ 1681204 MLS
Welcome home to this newer-model home set on a spacious 1.56-acre lot. Offering 3 bedrooms and 2 full baths, this home features a modern design with a comfortable, functional layout. The kitchen is a standout, with plenty of workspace, a convenient layout, and a beautiful pantry closet providing ample storage for all your kitchen needs. A great opportunity for buyers looking for the comfort and modern features of a newer home with the added benefit of acreage.

39 S Greenridge Hts, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

872 Kennedy Memorial Dr, Oakland
$350,000
1680961 MLS
Excellent Investment Opportunity! This property is being offered for sale subject to an existing 5-year lease, with two additional 5-year renewal options. Located in a great location with strong visibility and accessibility, this property offers an attractive opportunity for an investor seeking long-term income and future A solid investment with an established tenant and additional lease terms providing stability and flexibility for the future.

872 Kennedy Memorial Dr, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

368 Belgrade Rd, Oakland
$315,000
3 Beds ⋅ 2 Baths ⋅ 1680882 MLS
MOTIVATED SELLER; concessions available for permanent/temporary rate buy downs, updates to make it your own, or closing fees. Bring your Offers! Well kept, with room to make it yours. This 3 bed, 2 bath raised ranch sits on 0.69 acres at the end of a long, partially paved, private driveway, minutes from I-95. The main level has a living room, kitchen with a pantry, a separate dining area, two bedrooms, and a full bath. Both main-level bedrooms are freshly painted, and the decks were just painted too. Carpet remains in a couple of rooms if you'd like to pick your own flooring. The walkout lower level adds a third bedroom and a second full bath, both freshly painted, plus two bonus rooms for an office, gym, or playroom. The floors are smooth concrete, easy to finish however you like. You can come and go through the lower-level walkout. Over 2,100 sq ft in all, with a big backyard and plenty of wildlife. Minutes from Messalonskee and a short drive to the Belgrade Lakes. Seller can provide contact info for an affordable, reliable, local snowplow service already familiar with the property, currently about fifty per plow.

368 Belgrade Rd, Oakland

Listing courtesy of The Maine Real Estate Experience.

18 Fieldstone Dr, Oakland
$439,500
3 Beds ⋅ 3 Baths ⋅ 1680788 MLS
Within Fieldstone Landing's desirable 55+ community , this well-maintained and spacious three-bedroom, two-and-a-half-bath home makes for an ideal living experience. Upon entering is the beautiful dining room and a well designed kitchen, featuring cherry cabinets that makes cooking enjoyable and efficient. This space seamlessly flows into the living room and beyond it lies the large four-season sunroom. This sunroom is a perfect retreat, offering ample natural light and easy access to the deck, making it an excellent spot for morning coffee or evening relaxation. The primary bedroom is a standout feature of the home with a well-appointed bathroom that includes double sinks and a pocket door, providing privacy for the walk-in shower and toilet area. Equipped with heat pumps in both the primary and living rooms, the home remains cozy in the winter months and refreshingly cool during the summer with minimal use of the oil furnace. Extra blown-in insulation in the attic contributes to energy efficiency, making heating and cooling both economical and effective. This property's two additional rooms can serve as bedrooms, a home office, or a hobby room. The half bath is conveniently located with a laundry area discreetly tucked behind bifold doors. The attached two-car garage includes an upstairs area for additional storage. The neighborhood is located on a dead-end private drive, making it perfect for leisurely walks and socializing with neighbors. Fieldstone Landing is not only about comfortable living but also about accessibility. The proximity to Waterville provides residents with a wealth of shopping options, restaurants, and health facilities. With easy access to I-95, commuting is a breeze, while nearby golf courses and the beautiful Belgrade Lakes chain offer recreational opportunities for outdoor enthusiasts. Generator Included.

18 Fieldstone Dr, Oakland

Listing courtesy of Lakehome Group Real Estate. info@lakehomegroup.com
126 Cottle Rd, Oakland
$209,900
2 Beds ⋅ 1 Baths ⋅ 1680679 MLS
New price alert! An affordable opportunity in a desirable Oakland location offers privacy and convenient access to I-95, Waterville/Augusta-area shopping and dining, local schools, and the region's beautiful lakes and outdoor recreation. Set on 1.24 acres, this well-maintained 2015 mobile home features two bedrooms, tasteful updates, and a newly constructed back deck. Two spacious storage sheds also convey, completing this move-in-ready package. Stop paying your landlord's mortgage and start building equity in a place of your own!

126 Cottle Rd, Oakland

Listing courtesy of Integrity Homes Real Estate Group, PC.

137 Petris Avenue, Oakland
$1,445,000
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
20 & 21 Bass Cv, Oakland
$748,000
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
35 Summer St, Oakland
$239,900
2 Baths ⋅ 1678579 MLS
Unique multifamily opportunity in Oakland! This two-family property offers two 3-bedroom, 1-bath units, providing flexibility for rental income, extended living arrangements, or a combination of both. A detached garage located alongside the building provides additional storage and parking options. Conveniently located on Summer Street, this property offers plenty of space and versatility in a desirable Oakland location. A great opportunity to own a multifamily property with the added benefit of a separate garage.

35 Summer St, Oakland

Listing courtesy of NextHome Northern Lights Realty. Office@NextHomeNLR.com
334 Town Farm Rd, Oakland
$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.

Tbd Stoneybrook Dr Unit Lot 2, Oakland
$50,000
1677616 MLS
Discover the possibilities on this 1.42-acre wooded lot located on Stoneybrook Drive in Oakland. A peaceful, natural setting with mature trees and plenty of privacy, offering an opportunity to build your Maine getaway or future home. Electricity is available along the road. The property does not currently have a well or septic system. A great opportunity to own a private piece of land in a desirable Oakland location. Lot 1 Stoneybrook Drive also available see MLS #: 1677610

Tbd Stoneybrook Dr Unit Lot 2, Oakland

Listing courtesy of NextHome Northern Lights Realty. Office@NextHomeNLR.com
Tbd Stoneybrook Dr Unit Lot 1, Oakland
$55,000
1677610 MLS
Discover the possibilities on this 1.42-acre wooded lot located on Stoneybrook Drive in Oakland. A peaceful, natural setting with mature trees and plenty of privacy, offering an opportunity to build your Maine getaway or future home. Electricity is available along the road. The property does not currently have a well or septic system. A great opportunity to own a private piece of land in a desirable Oakland location.

Tbd Stoneybrook Dr Unit Lot 1, Oakland

Listing courtesy of NextHome Northern Lights Realty. Office@NextHomeNLR.com

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