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$1,100,000
3 Beds ⋅ 2 Baths
Tucked among the ferns and spruce on a quiet private road off South Road, this quintessential shingle-sided seasonal cottage captures the timeless charm of Chebeague Island. Built in 1980, this well-maintained home offers a warm, comfortable cottage feel that invites you to slow down and enjoy island life. The open-concept first floor seamlessly blends the kitchen, dining, and living areas, all anchored by a cozy wood stove that naturally draws everyone together after a day on the water. A first-floor bedroom adds convenience, while the sun-filled flex room offers a space for creative pursuits, quiet reading, or additional guest accommodations. Upstairs, two comfortable bedrooms and a full bath provide ample space for family and guests. Enjoy morning coffee on the screened porch, unwind on the open deck overlooking the water, or meander down the path to your own sandy beach with more than 300 feet of privately owned frontage. Set on over 5 acres, the property offers exceptional privacy along with room for potential expansion. Whether you're looking for a peaceful summer retreat, a place to gather friends and family, or simply a classic Maine island cottage to make your own, this special property offers an opportunity to become the next stewards of a cherished Chebeague Island home. Island amenities include beaches, trails, golf, tennis, a full-service boatyard, cafe and gift shop, seasonal dining, recreation center with pool, and library. Accessible by both Casco Bay Lines and Chebeague Transportation Company, as well as water taxi service from Portland.

26 Springettes Rd, Chebeague Island

Listing courtesy of Portside Real Estate Group.

$1,495,000
5 Beds ⋅ 3 Baths
The Chimes House, believed to be a design by Gustav Stickley during the American Arts and Crafts Movement, is a distinctive Staley year-round cottage that reflects the timeless appeal of early twentieth-century craftsmanship. One of the era's celebrated homes, it embodies Stickley's philosophy of simplicity, exceptional quality, and harmony with the natural surroundings. Designed with open floor plans and family-friendly living spaces, the home features original built-in benches, cabinetry, and bookcases. Many historic details remain intact, including the original light fixtures and hardwood floors that complement this four-bedroom, two-and-one- half-bath residence. The property enjoys stunning long-water views across Townsend Gut, with seasonal winter views extending farther up the Gut. Residents enjoy access to a deeded association dock, providing convenient boating access to Boothbay Harbor and beyond. Thoughtfully updated while preserving its historic character, the home was relocated to its present site and now rests on a new foundation with steel beams. Recent improvements include updated electrical systems, a new fire and security system, a new four-bedroom septic system, new roofs on both the house and garage, a new cedar fence, fourteen new windows, and a complete exterior repaint. Additional features include an oversized basement and garage, an expansive classic wraparound porch, and a massive entertainment deck adjoining the kitchen and dining areas. Located within the Chimes Association in the highly sought-after West Boothbay Harbor area, the property offers quick access by boat to Boothbay Harbor and all that Maine's coast has to offer during the summer season.

1 Chimes Ln, Boothbay Harbor

Listing courtesy of Benchmark Real Estate.

$699,000
3 Beds ⋅ 2 Baths
Nestled on 5.3 private acres in Georgetown's coveted Bowman's Landing, this beautifully maintained, turn-key home offers 3 bedrooms, 2 full baths, and 2,150 +/- square feet of thoughtfully designed living space. Surrounded by mature woods and abundant wildlife, the property blends exceptional privacy with access to some of Midcoast Maine's most treasured outdoor amenities. Owners enjoy over 1,000 feet of shared frontage on the Kennebec's Back River, including kayak access and a private island connected by an elevated boardwalk through the salt marsh. Step directly from your backyard onto Bowman's Landing's 42-acre network of private hiking and cross-country ski trails that wind through conserved woodlands and onto the island's scenic loop paths. Just minutes from Reid State Park, Robinhood Marina, the Morse Pond Preserve, and the Schoener Robinhood Cove Preserve, this exceptional location offers some of coastal Maine's finest boating, hiking, and year round recreation. Peaceful and secluded, yet within easy reach of Brunswick, Bath and Portland, this is an ideal primary residence or the perfect Maine retreat for those seeking an authentic coastal lifestyle.

100 Bowmans Lndg, Georgetown

Listing courtesy of Legacy Properties Sotheby's International Realty.

$499,900
3 Beds ⋅ 2 Baths
Nestled in the quaint Village of Springvale, Maine, this charming 3+ bedroom, 1½ bath home has the perfect combination of small-town convenience and waterfront living. With 107 feet of privately owned frontage on the beautiful Mousam River, you'll enjoy kayaking, canoeing, fishing, or simply relaxing by the water from your own dock while taking in peaceful sunsets. The inviting open-concept kitchen with island, dining, and living area creates the perfect setting for everyday living and entertaining, complete with a cozy wood stove to gather around and keep you warm on cool Maine evenings. A first-floor bedroom provides convenience and flexibility, while a bonus room provides extra space for a family room, playroom, or hobby area. The second floor is full of possibilities, featuring a spacious primary bedroom with beautiful views overlooking the Mousam River, a great office space for working from home, a second bedroom and additional rooms that are ideal for overnight guests, a craft room, or additional living space. Step outside to enjoy the expansive deck, lush green lawn, and private dock, making it easy to spend your days on the water or entertain family and friends in your own backyard oasis. Located just a short walk from local restaurants, shopping, banking, the library, Nasson Health Care, and many other village amenities, this home offers the best of both worlds-walkable convenience and serene waterfront living. Whether you're searching for a year-round residence or a peaceful waterfront retreat, this special property is ready to welcome you home!

428 Main St, Sanford

Listing courtesy of Lakes Region Realty.

$779,000
1 Beds ⋅ 2 Baths
Experience the best of waterfront living in this beautifully designed, open-concept cottage where light, comfort, and timeless coastal style come together. The inviting first floor features a designer kitchen with custom cabinetry, a striking soapstone island, and seamless flow into the fireplaced living and dining area--perfect for entertaining or relaxing after a day on the water. A convenient laundry room and half bath complete the main level. Upstairs, the vaulted-ceiling primary bedroom suite offers a peaceful retreat with a full bath and private second-story deck, where you can enjoy morning coffee, sea breezes, and tranquil water views. Just a short walk away, a deep-water pier provides full-tide access to a secure, protected mooring field, making this an exceptional opportunity for boating enthusiasts. Whether you're seeking a year-round residence or a charming waterfront getaway, this thoughtfully designed cottage offers an ideal blend of luxury, comfort, and coastal convenience.

32 Ocean Ridge Rd, Cushing

Listing courtesy of RE/MAX JARET & COHN. rockland@jaretcohn.com
$995,000
2 Beds ⋅ 3 Baths
Along the shores of Robinhood Cove, where the tides quietly shape each day, this exceptional Cape Cod-style residence captures the enduring appeal of coastal Maine. Set on 3 private acres with 425 feet of owned waterfront and a pebble beach, the property offers an uncommon blend of privacy, craftsmanship, and connection to the water. Swim from your own shore, launch a kayak at sunrise, or spend the afternoon exploring the quiet coves that define this remarkable stretch of coastline. Built in 2005, the home is thoughtfully designed to embrace its surroundings. Sunlight fills the interior, illuminating rustic timber beams, rich hardwood flooring, and inviting living spaces that feel both elegant and comfortable. At the heart of the home, the kitchen is appointed with upgraded cabinetry, granite countertops, and an expansive walk-in pantry. A striking floor-to-ceiling stone hearth with a wood-burning fireplace anchors the living room, while French doors reveal a distinguished den with custom built-ins--an ideal library, study, or home office. A full bath completes the first level. Upstairs, the primary suite offers a peaceful sanctuary overlooking the cove, complete with a spa-inspired bath featuring a soaking tub and a private deck perched above the three-season porch, where morning coffee is best enjoyed with the sound of the water below. An upstairs laundry room adds everyday convenience. The walk-out lower level presents exceptional potential for additional finished living space, opening directly onto a brick patio and the beautifully wooded grounds beyond. Surrounded by mature trees, the setting offers premier privacy rarely found along the coast. Near the water's edge, a quintessential Maine cabin with electricity and water provides an inviting retreat for guests, a studio, or a quiet escape immersed in nature. Only minutes from Georgetown Center, Reid State Park and the public boat launch, this is a property that embodies the rhythm of Maine's coast.

77 Higgins Farm Rd, Georgetown

Listing courtesy of Portside Real Estate Group.

$575,000
1 Beds ⋅ 1 Baths
Nestled on the water's edge in a peaceful cove on beautiful Damariscotta Lake, this charming cottage offers the perfect lakeside retreat. Enjoy approximately 200 feet of waterfront with your own dock, making it easy to spend your days swimming, boating, kayaking, paddleboarding, or fishing right from your property. Inside, the cozy cottage features a kitchen, dining area, comfortable living room, and a screened porch where you can relax with your morning coffee or unwind while taking in tranquil lake views. Surrounded by abundant wildlife and the sounds of nature, this is a wonderful getaway for making lasting memories on one of Maine's most sought-after lakes.

214 Wildwood Shores Rd, Nobleboro

Listing courtesy of Black Duck Realty.

$1,599,000
2 Beds ⋅ 2 Baths
113 Perkins Cove is a classic three-level, single-family year-round oceanfront cottage with two bedrooms, two full bathrooms, and approximately 924 square feet of finished living space and located directly on the water, with an oceanfront deck and access to a pebble shoreline. The main level brings the kitchen and living area together around a gas fireplace, with sliding glass doors opening to the water-facing deck. Upstairs, the primary bedroom has its own gas fireplace, generous closet space, and open water views. The lower level includes a separate bedroom, full bathroom, laundry, and storage. The location makes it easy to enjoy Perkins Cove on foot, with restaurants, galleries, shops, and the Marginal Way nearby, while the cottage itself remains directly on the ocean. The property has an established rental history and may be purchased separately, or together with neighboring 115 Perkins Cove Road and 117 Perkins Cove Road. It can serve as a second home, continue as a lucrative rental property, or become part of the full three-property waterfront offering. Rental history and financial information are available upon request.

113 Perkins Cove Rd, Ogunquit

Listing courtesy of Compass Real Estate.

$3,499,000
3 Beds ⋅ 5 Baths
115 Perkins Cove is a versatile four-unit mixed-use waterfront property. It includes a three-bedroom, 2.5 bath penthouse spanning the upper two levels, a ground-level oceanfront studio, and two street-level commercial units. The Penthouse is entered on the lower of its two levels, which includes a primary suite with a fireplace, full bathroom and ocean views. A second bedroom, another full bathroom and a third bedroom currently configured as a living room complete this level. Upstairs, the kitchen, dining area, fireside sitting area and sprawling water views come together in an open-concept layout. This level provides dual outdoor spaces: a deck facing the ocean and a larger deck overlooking Perkins Cove, suitable for outdoor dining and entertaining. The studio has its own entrance, deck, and fireplace, allowing it to serve as private guest accommodations or separate rental. The two commercial spaces, which are currently leased, provide a predictable and additional source of income. While not historically operated as full-time rentals, the penthouse and studio have seller-projected annual gross ST revenue of 250k - 310k. Projections are provided for informational purposes only and should be independently evaluated. Located in the heart of Perkins Cove, the property is surrounded by galleries, restaurants, shops, boat excursions and the Marginal Way, with Ogunquit's beach, village center and the Playhouse nearby. The property may be purchased separately, or together with one or both neighboring properties at 113 and 117 Perkins Cove Road. An owner could continue using the residential and commercial spaces to generate income or occupy the main residence while renting the studio and two commercial spaces. The property also offers potential for a different configuration or use over time, subject to applicable approvals. Rental history & projections available upon request.

115 Perkins Cove Rd, Ogunquit

Listing courtesy of Compass Real Estate.

$735,000
4 Beds ⋅ 2 Baths
Welcome to a rare opportunity to own a cherished vintage cottage on beautiful Frye Island, offered for sale for the very first time after generations of treasured family memories. This beloved waterfront retreat has been the setting for unforgettable summers, and one remarkable family member enjoyed golfing on Frye Island well into her 102nd year--a true testament to the island's timeless charm. Set on a peaceful lot with your own private sandy beach on the crystal-clear waters of Sebago Lake, this classic 4-bedroom, 1.5-bath cottage with heat pumps, is ready for its next chapter. Large windows fill the open-concept kitchen, dining, and living area with natural light, creating a warm and inviting space for family and friends. Enjoy its vintage character as-is or bring your vision to create the lakeside getaway of your dreams. Experience the unmatched Frye Island lifestyle with a 9-hole golf course, pickleball and tennis courts, community pool, walking trails, 13 beautiful community beaches, and roads perfect for walking and biking. The island also offers a waterfront restaurant, ice cream stand, general store, community center, and children's day camp, making it an ideal destination for all ages. Just 2.5 hours from Boston and about an hour from Portland, this is your chance to own a piece of classic Maine waterfront. Whether you're looking for a peaceful retreat or a place to build lifelong family traditions, this special property offers the opportunity to experience ''Maine, the way life should be.''

160 Ridge Rd, Frye Island

Listing courtesy of Sunset Lakes Real Estate.

$795,000
3 Beds ⋅ 3 Baths
Situated on more than 13 private acres with over 300 feet of stunning frontage on the beautiful Medomak River, this exceptional antique Cape offers a rare blend of historic character, remarkable versatility, and an idyllic coastal Maine setting. Rich with warmth and timeless appeal, the home showcases beautifully patinated wide pine floors, three inviting fireplaces, three or more comfortable bedrooms, and two-and-a-half baths. Every room reflects the craftsmanship and charm of a bygone era while providing comfortable spaces. Beyond the home, the possibilities are extraordinary. A unique mini event center is perfect for celebrations, gatherings, workshops, or entertaining, while a separate artist's/writer's studio offers an inspiring retreat. The enormous barn, workshop, and garage provide indoor parking for up to five vehicles, boats, or recreational equipment, making this an ideal property for collectors, hobbyists, or anyone needing exceptional storage and workspace. The grounds are simply breathtaking, with rolling lawns stretching toward the river, mature trees, a classic flagpole, and abundant privacy. The property abuts a large 100+ acre conservation parcel. Whether you're launching a kayak, enjoying a peaceful evening by the water, or simply taking in the ever-changing views, the Medomak River becomes an extension of your backyard. Despite its peaceful, secluded feel, this remarkable property is just minutes from the village of Waldoboro, where you'll enjoy convenient grocery shopping, local restaurants, theater, and everyday amenities. A truly special Maine waterfront estate where history, beauty, and endless possibilities come together.

1793 Friendship Rd, Waldoboro

Listing courtesy of Keller Williams Realty.

$299,000
5 Beds ⋅ 1 Baths
Rich with character and brimming with potential, this property presents a rare opportunity to restore, renovate, or thoughtfully modernize a home with exceptional space and timeless appeal. Whether you're looking to preserve its historic charm or create your dream home, the possibilities here are truly endless. Inside, you'll find five generously sized bedrooms, expansive living spaces, and an abundance of original character. Beautiful wide-plank wood floors, gracefully curved walls, and large windows that flood the home with natural light create bright, inviting rooms filled with warmth and charm. Storage is plentiful throughout, while the expansive, open yard abuts Tucker Brook, creating a picturesque backdrop with space to garden, entertain, play, or simply relax and enjoy the peaceful setting. Completing the home is an untapped third floor - a remarkable space ready to become additional living space, a luxurious primary suite, home office, studio, recreation room, or whatever best suits your vision. With its generous proportions, architectural character, and incredible potential, this is a home ready for its next chapter, offering the perfect canvas to create something truly special.

39 Main St, Standish

Listing courtesy of Locations Real Estate Group LLC.

$495,000
2 Beds ⋅ 1 Baths
Spend your summer in this 2 bedroom cottage with a private dock on Appalachee Pond in Boothbay Harbor. Situated on .15 +/- of an acre with 50' of frontage on the pond. Steps away from the beach to enjoy swimming or just watching the activity. There is also a common dock on Linekin Bay for access to boating, sailing or swimming in the ocean. Appalachee is a quiet community that is located on a dead-end road. Not far from the east side of the harbor and downtown amenities.

114 Appalachee Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$475,000
2 Beds ⋅ 1 Baths
Welcome to this brand new 2-bedroom, 1-bathroom condo offering 800 square feet of modern living space. This stunning lakefront property features an impressive 240 feet of flat sandy waterfront on beautiful Sokokis Lake, creating the perfect setting for waterfront living and recreation. The home showcases maintenance-free siding and flooring throughout, ensuring years of worry-free enjoyment. Climate comfort is provided by efficient heat pumps that deliver both heating and air conditioning. A large glassed-in deck overlooks the sparkling water, providing an ideal space for relaxation and entertaining while taking in the scenic lake views. Practical amenities include garage space perfect for storing boats, recreational equipment, or toys, making this an ideal retreat for water enthusiasts. The property is connected to public water and sewer systems for convenience and reliability. Location offers the best of both worlds - peaceful lakefront tranquility while remaining close to local amenities. Limerick Supermarket and Plummer's Hardware provide convenient shopping options nearby. Dining choices include the popular Sokokis Seafood Shack and Ice cream, as well as Town Hill Grille for casual meals. This property serves as excellent overflow space for guests visiting the lake, making it perfect for entertaining friends and family. The location provides easy access to outdoor recreation while being just two hours from Boston, offering the perfect balance between peaceful retreat and urban accessibility. This turnkey lakefront condo represents an exceptional opportunity for those seeking modern amenities, stunning water views, and the convenience of new construction in a desirable lake community setting.

148 Washington St Unit B, Limerick

Listing courtesy of Real Estate 2000 ME/NH.

$630,000
4 Beds ⋅ 3 Baths
This thoughtfully updated free-standing condominium offers four bedrooms and reflects years of careful ownership and attention to detail. The original builder finishes have been enhanced with timeless design elements, including solid cherry cabinetry, custom faux-finish painting, elegant wainscoting with classic chair rail detailing, and custom dentil molding framing the marble fireplace surround. A complete list of improvements is available. The finished walkout lower level expands the home's versatility with a spacious media and recreation room, a fourth bedroom, a full bath, and direct access to a private patio complete with a gas grill hookup, creating an ideal space for relaxing or entertaining. Beyond the home, enjoy access to approximately 400 feet of association-owned frontage on the Androscoggin River. A network of trails leads to the waterfront, offering an easy way to enjoy the natural setting and river views. Move-in ready and exceptionally well maintained, this home blends quality craftsmanship, thoughtful updates, and outstanding amenities in a comfortable, functional layout. Schedule your private showing today and experience everything this property has to offer.

40 Carriage Ln Unit 4, Brunswick

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$554,900
4 Beds ⋅ 4 Baths
OPEN HOUSE - SUN. AUG. 9TH 1PM-3PM More photos coming soon! Welcome to 59 Harbor View Drive, where outstanding harbor views, spacious living, and community amenities come together in this 4 bedroom, 3 1/2 bath waterfront condominium with an attached one-car garage in the highly desirable Village of Stockton Springs Harbor. Extensive, beautifully maintained perennial gardens welcome you with vibrant color and create a lovely first impression. Cathedral ceilings and two large private decks create a bright and inviting home designed to showcase the breathtaking ocean views. The main-level deck features a retractable awning, providing shade and added comfort while enjoying the waterfront scenery. The thoughtfully separated three-level layout provides plenty of room for guests to enjoy their privacy while still offering the convenience of first-floor living with a primary suite and laundry on the main level. The home features a gas fireplace, heat pump, stainless-steel appliances, a spacious pantry, generous closets, abundant storage, two large loving rooms on the main level and basement, generator hookup, and an attached one-car garage. Association amenities include a solar-heated swimming pool, community garden, kayak storage, and oceanside walking trails. The HOA also covers exterior maintenance, including roofing, siding, exterior painting, decks, and septic maintenance. Stockton Harbor, the public beach, park, and boat launch are just one minute down the hill. Walk to The Club, a popular waterfront restaurant, or spend the day swimming, kayaking, boating, and fishing. Centrally located between Belfast and Bangor, this provides convenient access to Acadia National Park and the many attractions, festivals, and activities found throughout Maine's Midcoast region. Whether gathering with family and friends or relaxing with your morning coffee, this exceptional property truly has it all! Schedule your private tour today!

59 Harbor View Dr Unit 59, Stockton Springs

Listing courtesy of Over the Bridge & Beyond Realty.

$499,000
3 Beds ⋅ 2 Baths
Please do not drive up the private road. Showings by scheduled appointment only. Tucked away at the end of a private dirt road, this beautiful 92± acre property offers the perfect blend of privacy, recreation, and country living. Enjoy open fields, mature pine and hardwood forest, private ATV and hiking trails, and approximately 1,600' along scenic Dead Brook. The fenced pasture is ready for horses, cattle, or other livestock, making it an ideal property for a hobby farm or outdoor lifestyle. Relax on the spacious farmer's porch and take in the peaceful mountain and pasture views while watching the wildlife pass by. Inside, the living room and kitchen feature handcrafted wood floors milled from trees harvested right on the property, creating a truly one-of-a-kind touch. The heated 28' x 36' oversized two-bay garage is a standout feature, complete with an Atlas automotive lift, generous workspace, and a large unfinished second floor offering endless possibilities for a workshop, studio, home office, guest space, or additional storage The home offers a comfortable layout with opportunities for the next owner to add their own finishing touches and make it uniquely theirs. Whether you're looking for a private retreat, recreational property, or country homestead, this property offers room to roam, work, and enjoy everything Maine has to offer.

79 Bear Mountain Way, Swanville

Listing courtesy of RE/MAX JARET & COHN. belfast@jaretcohn.com
$599,000
3 Beds ⋅ 1 Baths
There's still plenty of summer left to make this lakefront retreat your own! Wake up to stunning waterfront views and spend your days enjoying the private dock, expansive deck, and all that lake life has to offer in this classic Maine cottage. This charming getaway features three bedrooms, offering plenty of space for family and friends. After a day on the water, relax in the comfort of the heat pump's air conditioning, then gather around the wood stove on those quintessential crisp Maine evenings. Being sold fully furnished, this cottage is truly move-in ready...just unpack and start making memories on the beautiful shores of Little Ossipee Lake. Imagine spending Labor Day here, enjoying one last celebration of summer before the seasons change. Showings begin Thursday, August 6th.

88 Logan Cir, Waterboro

Listing courtesy of Maine Real Estate Experts.

$514,900
3 Beds ⋅ 2 Baths
Nestled along 250 feet of frontage on Woodsum Brook in the charming town of Harrison, this lovely home offers the perfect blend of comfort, convenience and peaceful surroundings. The inviting open-concept kitchen, living and dining area features soaring cathedral ceiling, creating a spacious setting for gathering with family and friends. The well-appointed kitchen boasts granite countertops, stainless steel appliances, a center island and a large sliding glass door that fills the space with natural light and leads to an expansive deck overlooking the private backyard. Offering 3 bedrooms and 2 full bathrooms, this thoughtfully designed home provides plenty of space for everyday living and entertaining. The primary suite features a generous walk-in closet and an ensuite bathroom with tile floors and double vanity sinks, creating a comfortable and private retreat. The basement provides the potential for expansion and is already plumbed for a bathroom. Designed for easy single-level living, the home also features first-floor laundry and an attached 2-car garage. Energy-efficient mini-splits provide both heating and air conditioning for year-round comfort. Ideally located less than 5 minutes from Harrison Village, approximately 10 minutes from downtown Bridgton and just 20 minutes to Pleasant Mountain Ski Area and the Naples Causeway, this property places you close to an abundance of four-season recreation and amenities. Enjoy easy access to shopping, dining, golfing, lakes and beaches, skiing, hiking trails and many community events that make the Lakes Region such a special place to visit or call home.

499 Norway Rd, Harrison

Listing courtesy of The Lakes Real Estate.

$575,000
3 Beds ⋅ 2 Baths
Welcome to 56 Highpoint Drive on Frye Island, a beautifully furnished and thoughtfully appointed home ideally located near the Community Center and just moments from some of the island's finest beaches. Move-in ready and meticulously maintained, this property allows you to simply unpack and begin enjoying the relaxed island lifestyle. The home features two generously sized bedrooms on the first floor, while the spacious second-floor primary suite offers a private en-suite bath, creating a comfortable retreat for owners and guests alike. The open-concept kitchen and living area provides an inviting space for gathering and entertaining. The kitchen has been updated with brand-new appliances and a new sink, blending style and functionality. The true highlight of the home is the expansive screened porch, stretching the full length of the house from front to back. This exceptional outdoor living space offers endless possibilities--whether you're enjoying your morning coffee, relaxing with a good book, dining al fresco with family and friends, or accommodating additional overnight guests with a sleeper sofa or daybed. Surrounded by town-owned land on two sides, the property enjoys added privacy and a peaceful setting. A charming backyard provides the perfect spot to unwind and enjoy the natural beauty of the island. As a Frye Island homeowner, you'll have access to an outstanding array of amenities, including pickleball and tennis courts, a community pool, ballfield, 9-hole golf course, general store and ice cream shop, restaurant and lounge, and live music and entertainment throughout the season. Frye Island offers a truly unique lifestyle--more reminiscent of a private resort than a traditional island community in Maine. Whether you're looking for a seasonal getaway or a place to create lasting family memories, 56 Highpoint Drive is ready to welcome you home.

56 Highpoint Dr, Frye Island

Listing courtesy of Better Homes and Gardens Real Estate/The Masiello Group.

$700,000
3 Beds ⋅ 3 Baths
Set on 6.1+/- picturesque acres with approximately 458 feet of frontage on Meadow Pond, this 1865 farmhouse offers a rare blend of historic character, privacy, and natural beauty. The grounds gently slope toward the water, with established landscaping surrounding the home, a well-kept lawn near the residence, and a more natural landscape beyond creating a peaceful meadow setting. Located on Oregon Road, the property enjoys both convenience and quiet; the town-maintained road ends shortly beyond the property, helping to keep traffic limited. Inviting, elegant, and comfortable, the home retains the warmth and charm of its 19th-century origins while reflecting thoughtful updates and additions completed over the years. The kitchen and living room flow together in a spacious, open gathering area ideal for entertaining and everyday living. Off the living room, the sunroom provides a tranquil place to take in views of Meadow Pond. A full bath on the first floor is located near a room currently used as a library and office, offering potential flexibility for a first-floor bedroom if desired. The second floor is designed with comfort and privacy in mind. One staircase leads to a generous primary suite with an ensuite bath, convenient access to the laundry room, and lovely views over the backyard and Meadow Pond. A separate staircase leads to another spacious bedroom on the opposite side of the home, which shares a full bath with the third, centrally located bedroom. Just off the kitchen, the attached two-car garage offers convenient everyday access and welcome protection during Maine's winter months. The current owners have made carefully considered improvements, including impressive foundation work creating a dry basement, additional updates including a supplemental heating system, a 12-kW generator, five new Andersen windows, and a recently shingled roof--enhancing the home's comfort and long-term appeal, providing confidence for the next owners.

139 Oregon Rd, Islesboro

Listing courtesy of Cates Real Estate. ginnie@catesre.com
$5,195,000
3 Beds ⋅ 5 Baths
More than 380 feet of frontage on Broad Cove and nearly five private acres create an extraordinary waterfront setting in the heart of Cumberland Foreside. Beyond a winding drive, the property reveals itself gradually, where mature trees frame the shoreline and the home settles naturally into the landscape. The experience here is defined by privacy, the quiet rhythm of the tides, and ever-changing water views from nearly every principal room. The property's size and configuration also present the potential to create a separate home site with water access. Designed to celebrate the landscape, the home unfolds through a series of beautifully proportioned spaces, each taking full advantage of the surrounding water and gardens. A dramatic two-story foyer, gracious living spaces, a vaulted sunroom wrapped in glass, and a beautifully appointed primary suite are all oriented toward the water, while rich millwork, warm hardwood floors, and carefully curated details create interiors that feel enduring and quietly refined. Bluestone terraces extend naturally toward the shoreline, inviting long summer evenings, effortless entertaining, or peaceful mornings overlooking the cove. Just minutes from Cumberland Center, Falmouth, Portland, yacht clubs, golf, and some of Maine's most treasured coastal destinations, this is a home of quiet beauty, where the landscape has always been the centerpiece.

26 Lanewood Rd, Cumberland

Listing courtesy of RE/MAX By The Bay.

$1,010,000
2 Beds ⋅ 2 Baths
This beautiful waterfront end unit at Jameson Point will convey largely furnished and is ready for your immediate enjoyment. Large waterfront deck with composite decking, central air conditioning, tastefully updated kitchen and bathrooms, attached 2 car garage. The condo has been recently updated with new siding, skylights, roof shingles, and trim. There are two bedrooms and two full bathrooms on the first floor, including the first floor primary bedroom suite which includes a large and very well appointed primary bathroom. Upstairs you'll find two additional living spaces with potential as a third bedroom, or an office area. Jameson Point is a peaceful and picturesque waterfront development fronting Rockland Harbor with spectacular views of the Breakwater and out to Penobscot Bay beyond. Easy access to downtown Rockland, the Samoset Resort, and all Midcoast amenities.

71 Jameson Point Rd Unit 71, Rockland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$479,000
2 Beds ⋅ 1 Baths
Looking for your own little darling spot in Maine? Look no further than this metal roof cottage cutie near the shores of Sebago on Frye Island. Home features great deck surrounded by lovingly cared for gardens and water views. Step inside and find nice wood floors, a first floor primary and spacious loft area with plenty of sleeping. Outside you'll find a well laid out lot with area for fire pit and space to gather with friends and family. Little shed/garage with power, for storing a golf cart, water toys, tools or could be converted to a bunk house for more guests. Lot backs up to Frye Island land that will not be built on along with lot on left hand side. facing the road. Very privacy feel. Quiet sandy Beach 12 is a short walk from cottage. Enjoy an outdoor shower after a day at the beach in the fresh Maine air as a bonus. Best of all this home comes with access to all the ammenities that Frye Island has: 14 community beaches, pickleball courts, tennis courts, 9 hole public golf course and lounge, community center featuring activities for kids and adults, walking trails, and great roads for walking, biking, or running. Don't miss out this opportunity that really gives you the taste of life in the lakes region of Maine.

129 Ridge Rd, Frye Island

Listing courtesy of Sunset Lakes Real Estate.

$549,000
3 Beds ⋅ 2 Baths
Welcome to Spirit Wind, an inviting Maine retreat, ideally situated just minutes from the ocean and conveniently located close to local town amenities and the hospital. Step inside to find warm, character-filled living spaces anchored by a stunning, central brick fireplace - perfect for cozying up on cool New England evenings. The exposed wood-beamed ceilings add classic coastal-craftsman warmth throughout the main living area. Unwind in the three-season porch, offering views of the private backyard and garden area - an ideal spot for morning coffee or afternoon relaxation. Outdoors, enjoy an attached, spacious garage with ample room for vehicles, storage, and a workshop. Combining quintessential Maine character, single-level comfort, and an unbeatable location near both coastal waters and everyday necessities, this property is a must-see!

529 Bristol Rd, Bristol

Listing courtesy of Blue Lobster Real Estate.

$2,300,000
7 Beds ⋅ 3 Baths
Welcome to 144 Surf Street, where you don't simply visit the ocean, you live with it. With deeded ownership extending to the high tide line, opportunities like this are increasingly rare along the Maine coast. This multi-family can be converted into a single-family home or into condos. Make this view belong to you. We SEA possibilities here. Continue its legacy as a sought-after weekly rental. Make it the summer gathering place your family returns to for generations. Or create a home where children, grandchildren, friends, and future guests write the next chapter of their story. Share dinners on the deck, laughter under the stars, and evenings accompanied by nothing more than the sound of the surf gently stirring. Offering three separate units with 7 bedrooms, 3 full baths, and expansive decks that naturally extend everyday living outdoors, this is a property designed for gathering. The ocean breeze becomes part of every conversation, every meal, and every memory. Please note - Two units are side by side, with two floor living. Unit three is the owner's unit and does not include a full kitchen, making it ineligible for use as a rental. The property has an established history of weekly rentals. Showings will be available on Saturdays only from 10am-2:30pm.

144 Surf St, Saco

Listing courtesy of Maine Home Connection. 207.517.3100
$625,000
2 Beds ⋅ 1 Baths
A Rare Woodland Sanctuary Awaits! Properties of this scale and character seldom become available in Midcoast Maine. Encompassing nearly 100 acres of mature mixed forest, streams, wetlands, and established trail networks, this exceptional property offers the rare opportunity to own a significant woodland landscape. Approximately 30 acres are under a conservation easement held by Midcoast Conservancy, while the property borders more than 6,000 acres of intact woodland habitat, creating an extraordinary haven for wildlife and outdoor recreation. The comfortable year-round residence features an open-concept kitchen, living and dining area, two bedrooms, one bath and a multipurpose bonus room ideal for a home office, studio, or creative space. Additional features include wood and oil heat with propane backup, an enclosed all-season porch, full basement with separate entrance, spacious attic, detached two-car garage, and carport. Whether your vision includes recreation, landscaping, woodworking, an artist's studio or a wilderness homestead, the infrastructure offers you all that's needed. Waldoboro itself offers the authentic charm of a quiet small-town Maine, with its local cafés, galleries, a theater, farmers markets, maritime history and a welcoming year-round community. Though wonderfully secluded, the property lies just minutes from Friendship Harbor and Maines spectacular Atlantic coastline speckled with lobster boats, docks and lighthouses. Launch a kayak on the Medomak River, explore nearby lakes and nature preserve trails, or enjoy the restaurants, galleries, live music, and working waterfronts of Damariscotta, Rockland, and Camden. For those who value privacy, stewardship, and the enduring beauty of Maine's natural landscape, this is far more than a home--it is an opportunity to create a lasting legacy for generations to come. SHOWN BY APPOINTMENT ONLY OWNER OCCUPIED NO DRIVE BYS PLEASE

674 Friendship Rd, Waldoboro

Listing courtesy of Keller Williams Realty.

$465,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained Cape Cod home, perfectly situated on 1.3-acres tucked into a peaceful country neighborhood along the Great Works River. Offering the ideal balance of privacy, comfort and convenience this move-in ready home is just minutes from local amenities, the Seacoast, and I-95 for an easy commute. Inside, you'll find nearly 2,000 square feet of inviting living space featuring four bedrooms and two full bathrooms, including a desirable first-floor bedroom option with a flexible floor plan ideal for guests, multigenerational living or convenient one-level living. The warm and welcoming living room is centered around a cozy gas fireplace, while the spacious dining area off the kitchen opens to an expansive sun-filled deck perfect for entertaining, outdoor dining, or simply relaxing while overlooking the private backyard. The finished walk-out basement adds exceptional versatility with space for a family room, recreation area, home office, fitness room or guest suite. Outside the yard provides plenty of room to play, garden or enjoy the peaceful natural surroundings. Thoughtfully maintained with major updates already completed, including a new boiler and newer roof, this home offers peace of mind for years to come. Whether you're a first-time homebuyer, growing family or someone seeking extra space in a quiet setting without sacrificing convenience this property checks all the boxes. If you've been searching for a move-in ready home with privacy, modern updates, flexible living space and the tranquility of country living just minutes from town 152 Sand Pond Road is one you won't want to miss!

152 Sand Pond Rd, Sanford

Listing courtesy of Keller Williams Coastal and Lakes & Mountains Realty.

$799,000
3 Beds ⋅ 2 Baths
Experience riverfront living on the Crooked River, offering direct access to Sebago Lake, Brandy Pond, and Long Lake. This beautifully turnkey log home blends timeless rustic character with modern comfort, creating a peaceful vacation retreat or year-round residence. Two private docks invite effortless days on the water, while the open-concept main level impresses with soaring cathedral ceilings, exposed beams, and a dramatic floor-to-ceiling stone wood-burning fireplace--a focal point for relaxed evenings and memorable gatherings. A main-level bedroom opens to a patio offering a serene place to take in the water views. The full bath has a soaking tub, shower, and laundry area. The second floor has two additional bedrooms and a half bath complemented by a balcony overlooking the living room. This riverfront setting is ideal for watching boats pass by and embracing the best of the Lakes Region lifestyle. A whole-house generator ensures peace of mind. Just moments from the Naples Causeway, waterfront dining, entertainment, and shopping, with Pleasant Mountain skiing, hiking trails, ATV trails, and snowmobile trails all within easy reach.

31 Welch Dr, Casco

Listing courtesy of Pine Tree Realty of Maine.

$2,850,000
3 Beds ⋅ 4 Baths
Set on a private 5.1±-acre peninsula-like lot with 638'± of natural shoreline on Middle Bay, this modern contemporary residence presents an extraordinary blend of architectural interest, privacy, and connection to the water. Originally built in 1972 and extensively updated and expanded over time, the home presents over 3,800± square feet of living space designed to take advantage of its south-facing orientation, capturing a beautiful progression of natural light throughout the day. The approach along a private right of way reveals the property's seclusion, with mature trees, ledge outcroppings, and landscaped gardens framing the home. Oversized windows and clean lines define the architecture, bringing in natural light and water views from nearly every room. The main living area features an open, airy layout with vaulted ceilings, a spacious living room anchored by a fireplace, and seamless flow to the dining area and well-appointed kitchen. All daily living spaces, a media room, billiard room, laundry, and a private, light-filled primary suite with direct water views are located on the main level for the ease of single-level living. Thoughtfully positioned to allow flexibility for guests or work/hobby use, a separate space with two bedrooms, a bath, and living area provides privacy and comfort. The property is to be sold mostly furnished, and recent improvements ensure the property is move-in ready while preserving its original modernist character. Outdoors, the setting is quintessential coastal Maine; a rugged ledge, gentle slopes to the tidal shore, and ever-changing views of Middle Bay's sheltered waters. The shoreline remains completely natural, preserving an authentic maritime environment with abundant birdlife and tidal movement. Set within Brunswick's historic Pennellville area, the location blends seclusion with convenience - just minutes from downtown's vibrant arts scene, Bowdoin College, fine dining, and Amtrak service to Boston and Portland.

27 Tidal Run Ln, Brunswick

Listing courtesy of LandVest, Inc..

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