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$425,000
1665804 MLS
Rarely does an opportunity arise to own nearly an acre of land on legendary Monhegan Island--one of Maine's most treasured and iconic island communities. This 0.97-acre parcel, located approximately 12 miles off the coast of Maine, offers a unique opportunity to create your own island retreat surrounded by rugged coastal beauty, tranquility, and the timeless character that has drawn artists, writers, and nature lovers for generations. Set in a peaceful setting with a sense of privacy that is increasingly difficult to find, the property provides an ideal canvas for a seasonal or year round getaway, artist's haven, or future investment. Monhegan is renowned for its dramatic ocean scenery, scenic hiking trails, working fishing village, and vibrant arts community, offering a lifestyle unlike anywhere else in New England. Adding to the appeal, certain commercial uses may be permissible on the property, creating intriguing possibilities for entrepreneurs and visionaries seeking to establish a presence within this unique island community. Buyers are encouraged to perform their own due diligence and consult directly with the State of Maine regarding zoning, permitted uses, and development requirements. Land includes an 8 x 12 Shed, Outhouse/Privy with a 1000 gallon septic tank, and a 16 x 16 insulated camp/building/studio with a propane hookup. Whether you're seeking a private escape, a creative sanctuary, or a property with future potential, this exceptional parcel offers a rare chance to own a piece of Maine island paradise. More pictures and video coming soon.

143 Blackhead Trl, Monhegan Island Plt

Listing courtesy of Tim Dunham Realty. 207-729-7297
$299,000
2 Beds ⋅ 2 Baths ⋅ 1665258 MLS
Enjoy carefree coastal living from this unique first-floor end-unit condominium overlooking Linekin Bay in picturesque East Boothbay. Set within a beautiful waterfront community, the property offers access to a shared dock, storage racks for kayaks, canoes, and paddleboards, and the potential for a private mooring (subject to town approval), making it a wonderful base for enjoying all that Maine's boating lifestyle has to offer. Originally designed as two separate units, the condo has been thoughtfully combined into one versatile space featuring a spacious bedroom with a full bath, along with a separate kitchen/living area and a second full bath. The flexible floor plan still lends itself well to lockout-style use, providing options for guests, extended family, or rental income. A standout feature exclusive to this unit is the large screened porch, where you can unwind with your morning coffee, enjoy the salty sea air, and take in spectacular sunsets over Linekin Bay. As an end unit, it benefits from natural light and easy first-floor access. Outside, residents enjoy beautifully manicured lawns and inviting common areas that create a peaceful waterfront setting and foster a warm, welcoming community of owners. Whether launching a kayak for a morning paddle, relaxing by the water's edge, or playing lawn games, you'll appreciate the charm and camaraderie this special property offers. This seasonal condominium presents an exceptional opportunity as an investment property, vacation getaway, or your own personal coastal escape in one of the Boothbay region's most desirable waterfront locations.

7a Wave Crest Dr Unit 101, Boothbay

Listing courtesy of Newcastle Realty. 207-563-1003
$2,900,000
4 Beds ⋅ 3 Baths ⋅ 1664387 MLS
On Southport Island's western shore, this private, 2.79-acre property is beautifully oriented to the west/southwest, capturing afternoon light, prevailing sea breezes, and stunning sunsets over Sheepscot Bay. The oceanfront setting is absorbed from its bold rocky shoreline, stone firepit, open decks, balconies, and screened porch. Inside, the home features open concept living, a generous primary bedroom suite, and plenty of room for guests, an office, and hobby space. Architecturally harmonious with the coastal Maine aesthetic, this home looks the part and delivers unlimited potential for daily satisfaction, alone or gathered with loved ones.

26 Miradon Ln, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$759,000
2 Beds ⋅ 2 Baths ⋅ 1664222 MLS
Presenting the charming home of Sweet Windruff Farm on East Side Road, Barters Island -- a timeless 1860s New England Cape offering warmth, character, and waterfront living on The Back River. Whether you're seeking a summer retreat or a year-round coastal home, this beautifully maintained property captures the essence of Maine living. Enter through the gate into a welcoming mudroom-style entryway featuring original brick flooring and classic built-ins. Beyond, the heart of the home opens into a warm dining and kitchen area centered around a cozy woodstove, with peaceful views stretching toward the cove and your waterfront frontage on The Back River. Rich in old-style charm and thoughtfully designed living space, the home offers two bedrooms and two baths, including a first-floor primary bedroom suite and laundry room for convenient one-level living. Upstairs provides additional privacy with flexible space ideal for guests, a sewing room, studio, or home office. The inviting living room and den feature built-in bookcases and a beautiful fireplace -- perfect for gathering with friends or simply taking the chill off a cool coastal evening. Every room reflects the care and personality of its current owners, blending comfort, craftsmanship, and timeless New England character. Outside, the property continues to impress. Set back from the road, the home enjoys a fenced yard with mature fruit and maple trees, sitting areas, a greenhouse, and a charming potter's shed. A lovely screened front porch offers the perfect place to relax and enjoy water views after a day exploring the Maine coast. The two-story barn, built in 1999 by a local craftsman along with the kitchen addition, provides exceptional versatility with garage space for vehicles or boats, a workshop, and an attached separate work area ideal for hobbies, storage, or a home-based business. This special waterfront property offers comfort, privacy, and authentic coastal charm in one of Maine's island communities.

367 East, Boothbay

Listing courtesy of Legacy Properties Sotheby's International Realty.

$918,000
3 Beds ⋅ 2 Baths ⋅ 1664144 MLS
Coastal Maine Retreat Near Pemaquid Point Lighthouse. Experience the beauty of Maine's coast from this charming 3-bedroom, 1.5-bath home with ocean views and exceptional outdoor living. Nestled on a beautifully landscaped lot within walking distance to the iconic Pemaquid Lighthouse, this property offers the perfect blend of privacy, comfort, and coastal charm. The home features a spacious and inviting layout filled with natural light and scenic views of the Atlantic. Outside, enjoy mature gardens, lush lawns, and peaceful sitting areas designed to capture the sea breeze and stunning surroundings. Property highlights include: 3 bedrooms and 1.5 baths, ocean views, beautifully landscaped grounds, detached two-car garage with loft space above, additional storage shed/outbuilding, walking distance to Pemaquid Point Lighthouse, ideal year-round residence or seasonal getaway. Located in the highly sought-after Pemaquid peninsula area, this property places you close to the beach. There is an adjacent buildable lot with unlimited potential.

23 Massasoit Dr, Bristol

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,150,000
7 Beds ⋅ 3 Baths ⋅ 1663898 MLS
With years of careful stewardship, all mechanical systems have been brought up to modern standards, and the roof has been completely replaced within the past 4 years. The flexible layout offers comfortable options for everyday living and hosting guests. The primary living space - perfect as the main residence - is on the harbor side of the building. The first floor consists of a living/dining area, a galley kitchen, a bedroom with an original tin ceiling that has recently been painted, a full bathroom, and a laundry. Behind the main residence is a large, maintenance-free deck. The second floor has 2-3 bedrooms (2 of which face the harbor). The third serves as an additional sitting room, which can easily be converted into a bedroom. There is a second large bathroom, as well as a small kitchenette and dining area. The second floor is ideal for extended family, friends, or as an extra rental income. The third floor features a bonus room with a large window that captures spectacular views of the harbor and Manana Island. Additional storage is built into the knee walls. The bonus room has a vented skylight and a ceiling fan with light. The attached income property is a remodeled three-story Guest House. On the first floor is a full kitchen with a ceiling fan with light. The kitchen opens to the living/dining area, and a large deck and privacy fence are located outside the kitchen door. The second floor of the Guest House has a large master bedroom with a ceiling fan with light. The hall bathroom is located just outside the master bedroom. The third floor has a charming loft bedroom with a vented skylight to welcome the ocean breeze. There is another ceiling fan with light in the loft. Located behind the house is a large storage shed with a freezer chest. The metal roof was replaced in 2025.

5 Wharf Hill Rd, Monhegan Island Plt

Listing courtesy of LandVest, Inc..

$1,150,000
1663900 MLS
With years of careful stewardship, all mechanical systems have been brought up to modern standards, and the roof has been completely replaced within the past 4 years. The flexible layout offers comfortable options for everyday living and hosting guests. The primary living space - perfect as the main residence - is on the harbor side of the building. The first floor consists of a living/dining area, a galley kitchen, a bedroom with an original tin ceiling that has recently been painted, a full bathroom, and a laundry. Behind the main residence is a large, maintenance-free deck. The second floor has 2-3 bedrooms (2 of which face the harbor). The third serves as an additional sitting room, which can easily be converted into a bedroom. There is a second large bathroom, as well as a small kitchenette and dining area. The second floor is ideal for extended family, friends, or as an extra rental income. The third floor features a bonus room with a large window that captures spectacular views of the harbor and Manana Island. Additional storage is built into the knee walls. The bonus room has a vented skylight and a ceiling fan with light. The attached income property is a remodeled three-story Guest House. On the first floor is a full kitchen with a ceiling fan with light. The kitchen opens to the living/dining area, and a large deck and privacy fence are located outside the kitchen door. The second floor of the Guest House has a large master bedroom with a ceiling fan with light. The hall bathroom is located just outside the master bedroom. The third floor has a charming loft bedroom with a vented skylight to welcome the ocean breeze. There is another ceiling fan with light in the loft. Located behind the house is a large storage shed with a freezer chest. The metal roof was replaced in 2025.

5 Wharf Hill Rd, Monhegan Island Plt

Listing courtesy of LandVest, Inc..

$2,450,000
3 Beds ⋅ 3 Baths ⋅ 1663865 MLS
Set between the timeless coastal communities of Waldoboro and Bremen, this remarkable 167-acre saltwater farm offers a rare and enduring connection to Maine's unspoiled past. Held and thoughtfully cared for by the one family for more than half a century, the land reflects a legacy of stewardship, enriched through traditional oxen-powered farming. At its center stands a classic antique Cape Cod farmhouse, rich in character and authenticity, featuring three bedrooms, three baths, a formal dining room, and multiple working fireplaces that evoke the warmth and simplicity of an earlier era. Supporting structures include a garage, a charming carriage house, and a substantial pole barn, offering flexibility for agricultural pursuits, livestock, or inspired new uses. The landscape is both diverse and harmonious, unfolding across open organic fields, a serene stretch of old-growth forest alive with wildlife, and a private peninsula extending into the waters of Broad Cove. Here, sweeping views, tidal access, and exceptional privacy create a setting that is breathtaking. Whether envisioned as a working farm, a private coastal retreat, or a legacy family compound, 275 Harriman represents a truly rare opportunity to own a meaningful piece of Maine's coastal heritage.

275 Harriman Rd, Waldoboro

Listing courtesy of L&S Realty.

$950,000
2 Beds ⋅ 2 Baths ⋅ 1663839 MLS
Classic Maine waterfront cottage with breathtaking sunsets and sparkling ocean views. This beautiful setting offers 2 cottages on the water! The main cottage is bright and airy with a great room and master bedroom. The guest house is perched at the edge of the pier and offers sleeping for four more guests. Both have exceptional views for the quintessential Maine waterfront getaway! This retreat features an expansive south-facing deck perched directly over the water, offering front-row seats to passing tall ships and ever-changing harbor scenery. Launch from your private dock and explore the harbor, cruise through Townsend Gut, or venture onto the Sheepscot River and beyond. Thoughtfully renovated in 2021, this turnkey property is being offered fully furnished, providing an effortless opportunity to enjoy the very best of Maine waterfront living. Come stand on the deck, soak in the salt air and the view, you won't want to leave!!

78 West St, Boothbay Harbor

Listing courtesy of Vitalius Real Estate Group.

$1,050,000
2 Beds ⋅ 2 Baths ⋅ 1663769 MLS
Experience the charm of a classic Maine waterfront cottage, where breathtaking sunsets and shimmering coastal views create an unforgettable setting. This beautifully updated two-bedroom retreat features an expansive south-facing deck perched directly over the water, offering front-row seats to passing tall ships and ever-changing harbor scenery. Launch from your private dock and explore the harbor, cruise through Townsend Gut, or venture onto the Sheepscot River and beyond. Nestled within a protected cove, enhanced by lush landscaping, vibrant gardens, and a secluded private beach that create your own peaceful coastal oasis. Thoughtfully renovated in 2021, this turnkey property is being offered fully furnished, providing an effortless opportunity to enjoy the very best of Maine waterfront living.

76 West St, Boothbay Harbor

Listing courtesy of Vitalius Real Estate Group.

$1,495,000
3 Beds ⋅ 4 Baths ⋅ 1663763 MLS
Beautiful water views fill nearly every room of this immaculate, sun-drenched home, perfectly situated on more than 2 private acres on a dead-end road. Complete with a deep-water dock, that has exceptional landscaping, well-built stairs to the shore, and parking areas, this property offers the ideal blend of comfort, privacy, and coastal living. Wrap around porches and spacious decks surround the home, providing stunning water views from every angle. The first-floor primary suite features private deck access, a full bath, and an adjacent laundry room. This versatile space could also serve as a home office, den, or guest suite with its own private entrance and easy access to the patio firepit area. The large, sun-filled kitchen offers beautiful water views, an oversized island, and a cozy dining area where you can watch boats pass by while cooking or entertaining. A half bath and attached oversized two-car garage are conveniently located just off the kitchen. The inviting living room features a striking stone fireplace and doors leading to the covered porch with more waterviews, the perfect place to relax and unwind. Upstairs, a spacious bonus room with dramatic windows overlooking the water creates endless possibilities for a game room, office, media room, or guest/in-law space. It has a private staircase coming up from the kitchen. There is an additional large room which provides even more versatility next to it. This level also includes a full bathroom and a smaller bedroom. There is impressive Primary suite featuring two walk-in closets, panoramic water views, and a great master bathroom. The large, dry basement offers tremendous additional space and is currently used as a home gym. Outside, you'll also find a separate tool and garden shed along with a large circular driveway with plenty of room for boats, trailers, and recreational vehicles. A peaceful waterfront retreat with breathtaking views, flexible living spaces, and exceptional amenities.

79 Fort Rd, Edgecomb

Listing courtesy of Legacy Properties Sotheby's International Realty.

$349,000
1658768 MLS
Here is an opportunity to own the last building lot on Yellow Head in beautiful New Harbor. The lot has a drilled well and a septic plan. Located at the end of a private road along with other improvements the driveway is in place and electricity is at the street. There is an acre of land that has been cleared for a home site. Bring your house plans and enjoy living in a beautiful coastal community.

37 Yellow Head Rd, Bristol

Listing courtesy of Drum & Drum Real Estate Inc..

$115,000
1657602 MLS

265 Friendship Rd, Waldoboro

Listing courtesy of Beacon Realty.

$265,000
1659679 MLS
Secluded Building Site on Highly Desirable Westport Island with Barn & Infrastructure Already in Place! Tucked away in the peaceful natural setting of Westport Island, this exceptional parcel offers a rare opportunity to create your ideal private retreat while already benefiting from valuable improvements. The property features a substantial existing barn, perfect for storage, workshop space, or future conversion possibilities. Whether you're envisioning a homestead, seasonal getaway, or custom-built residence, this structure provides immediate utility and long-term flexibility. A standout feature of the land is its well-developed roadway system and expansive parking area, allowing easy access throughout the property and simplifying the building process. Much of the groundwork has already been completed--saving time, expense, and effort as you bring your vision to life. A small brook, Squam Creek cuts through the middle of the property and provides a a soothing element to the whole property. Surrounded by nature, the setting offers privacy and seclusion, yet remains conveniently located just minutes from the charming coastal village of Wiscasset and within easy reach of the vibrant amenities, dining, and shopping in Brunswick and Damariscotta. If you've been searching for a ready-to-build site with character, infrastructure, and a peaceful Maine setting, this property delivers a unique and compelling opportunity. Call today for a private showing. This wonderful parcel wont last!

150 Post Office Rd, Westport Island

Listing courtesy of Keller Williams Realty.

$2,500,000
1626100 MLS
This listing is for the Resturant and Wharf only. After 30+ years Shaw's Wharf and Lobster is For Sale. This property boasts a fantastic location and excellent income producing restaurant that seats 300+ inside and outside with a fun and lively bar area, known for it's weekly bands. Included is a 13,000 sq ft (town records) Commercial Wharf that sells lobsters both to the public and wholesale. Shaw's Wharf leases space to a well known Tour Boat that does tours to Monhegan and other areas. This property also has two separate buildings that contain a lobster pound/bait shed and office.This is the location where part of the movie ''Message in a Bottle'' was filmed, Kevin Costner, Paul Newman, and Robin Wright and lots of locals were there. Most of the photos were taken after the restaurant was closed. Financials will be provided to Qualified Buyers with signed Non-Disclosure Agreement. See MLS #1610820 for more parcels included for sale

127, 129 State Route 32nd Rte, Bristol

Listing courtesy of Legacy Properties Sotheby's International Realty.

$175,000
1660553 MLS
Looking for a secluded lot on a quiet back road on the coast of Maine? This is an improved lot with a foundation, driveway, well, and power right at the street. A great start to your new home. Check out the building plans or customize it! Nicely wooded with mature trees, it blends will with the established neighborhood. Enjoy the tennis/pickleball court as part of the amenities that this lot offers. The lot has the ''best well in the neighborhood'' according the original developers at 20 gallons per minute. And there is reportedly an elevated ledge that looks over the pond on the association lot. So much to love! And with the foundation, house plan, well, and driveway already in place, you are on your way to beautiful home in a a wonderful little neighborhood. Septic design is also available. Close to everything our great peninsula has to offer: Wawenock Golf Course, Pemaquid Harbor, Beach, and Lighthouse, so much to do and see in the area, with the quaint restaurants and gift shops of Damariscotta less than 15 minutes away. Please inquire about a showing, we're happy to meet you on-site. **Keeping it real! There are no AI modifications or fishbowl or drone photos. What you see in the pictures is exactly what you will see in person!**

34 Bunchberry Ln, Bristol

Listing courtesy of Bay Watch Realty, LLC.

$1,590,000
2 Beds ⋅ 3 Baths ⋅ 1655796 MLS
NEW PRICE - Round Pond Waterfront Retreat Significant price reduction on this exceptional Midcoast Maine waterfront property. Located on a quiet dead-end road in the charming village of Round Pond, this custom-designed, move-in-ready home offers privacy, quality craftsmanship, and breathtaking ocean views. Built with Maine's four seasons in mind, the home features durable 2x6 construction and convenient single-level living throughout. Set on 3 private acres with 184' of deep-water frontage, the property enjoys sweeping easterly views of Muscongus Bay and the Atlantic Ocean, delivering spectacular sunrises year-round. Filled with natural light this thoughtfully designed home offers 2+ bedrooms, 3 full baths, spacious living areas, and room for future expansion. The welcoming living room features a striking stone fireplace and panoramic water views, while new carpeting adds a fresh touch throughout. The finished walkout lower level provides additional living space ideal for guests, entertaining, or multi-generational living. Complete with a full bath, patio access, and ample storage, it offers exceptional flexibility. An expansive wraparound deck, accessible from multiple rooms and featuring a ramped entry, creates seamless indoor-outdoor living. The gently sloping, manicured grounds lead to a private rocky shoreline, perfect for enjoying Maine's coastal beauty in every season. Additional amenities include an attached two-car garage with direct entry, whole-home generator, and a detached workshop/shed with power. Conveniently located near Pemaquid Point Lighthouse, local beaches, scenic trails, and the shops, dining, and cultural attractions of Damariscotta, this property offers the best of Midcoast living. Whether you're seeking a year-round residence, seasonal escape, or legacy waterfront property, this rare coastal sanctuary is not to be missed.

153 Back Shore Rd, Bristol

Listing courtesy of Keller Williams Realty.

$4,895,000
4 Beds ⋅ 4 Baths ⋅ 1660620 MLS
Glidden Ledge - an outstanding 13.35± acre waterfront property with panoramic views over Fitch Cove, the Damariscotta River, and out to Glidden Ledge. This landholding includes a beautifully designed main residence, three-car garage, guest cottage, and a charming shed. The four-bedroom home features a refined yet comfortable layout with high-end materials and systems, centered around a dramatic timber-frame great room with a coffered ceiling and two-story stone fireplace. Additional highlights include a main-floor primary suite and a spacious screened porch with its own stone fireplace. A winding drive leads through thoughtfully cultivated grounds with over a mile of walking paths, mature gardens, and scenic outdoor spaces, including a unique point of land with a small private island as part of this estate. The property offers 2,716± feet of varied shoreline, a dock with three floats, and a mooring. Wildlife is abundant, from bald eagles to daily seal visits on the western ledges, and the fishing is excellent. This is remarkably an entire non-public peninsula with unparalleled beauty, peace and quiet spaciousness. Private yet convenient, the property is near Wawenock Golf Club, Pemaquid Beach, and Pemaquid Point Lighthouse, with the coffee shops, dining, stores and culture of Damariscotta and Newcastle just six miles up the road.

16 Glidden Ledge Rd, South Bristol

Listing courtesy of Camden Coast Real Estate. info@camdencoast.com
$2,895,000
4 Beds ⋅ 4 Baths ⋅ 1662528 MLS
Set on Maine's bold coast, this four-bedroom, three-and-a-half-bath colonial offers sweeping ocean views with Monhegan Island on the horizon. Surrounded by tall pines, manicured gardens, and the sound of crashing surf, the property provides a private, front-row seat to Maine's dramatic shoreline. The first floor is arranged for gracious living and comfort. A vaulted living room anchored by a ceiling-height fieldstone fireplace creates a striking central gathering space. The large kitchen, with a sunny breakfast nook, opens to an inviting family room with a wood stove and wet bar. Doors from both the living room and family room lead directly to the ocean-facing deck and screened porch, creating a seamless indoor-outdoor flow. Two first-floor bedrooms, each with an en suite full bath, allow for true single-level living. The ocean-facing primary suite includes a generous walk-in closet with thoughtful built-in storage. A formal dining room, powder room, and laundry room complete the main level. An open staircase leads to the second-floor balcony overlooking the living room. The upper level includes a spacious office area with a built-in desk and shelving, two additional bedrooms, and a full bath. Outdoors, stone steps built into the ledge lead to an upper garden framed by dry-laid stone walls and mature plantings. The property has an immaculately clean, dry basement space with double-door exterior access and abundant storage, along with a three-car garage and a whole-house generator. Set on 3.6 acres, the grounds are beautifully maintained and offer privacy and sweeping coastal light. This is a rare opportunity to own an oceanfront home on Maine's bold coast.

28 Yellow Head Rd, Bristol

Listing courtesy of Drum & Drum Real Estate Inc..

$1,200,000
3 Beds ⋅ 2 Baths ⋅ 1662201 MLS
Rare opportunity to own a waterfront home on coveted Fish Point Road in New Harbor, where properties seldom come to market. Lovingly maintained by the same family for generations, this charming 3-bedroom, 1.5-bath Cape offers stunning frontage on John's Bay and sweeping water views from many of the home's primary living spaces. The spacious kitchen features abundant cabinetry and flows into an eat-in dining area perfectly positioned to take in the breathtaking scenery. A bright and inviting living room also captures the panoramic bay views, while the small covered porch provides the ideal spot to enjoy morning coffee, sea breezes, and peaceful sunrises. An attached two-car garage adds convenience and additional storage. Ideally located within easy walking distance to Little Beach, Pemaquid Beach, Fort William Henry, and Colonial Pemaquid, this special property places you in the heart of one of Maine's most beloved coastal communities. Enjoy nearby restaurants, scenic harbors, and the iconic Pemaquid Point Lighthouse just minutes away. Whether you are searching for a year-round residence or a treasured seasonal retreat, this waterfront gem offers a rare chance to create lasting memories for generations to come. Be sure to watch the video so you can fully appreciate the gorgeous surroundings and setting of this wonderful property.

1 Fish Point Rd, Bristol

Listing courtesy of Newcastle Realty. 207-563-1003
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 1639704 MLS
''Eagle's Nest''. Nestled on its ideally elevated perch above the Sheepscot, with sweeping views of the sea life, this classic 3-Bedroom, 2 1/2-Bath Coastal Home offers breathtaking elevated views, deep-water frontage, and the peaceful rhythm of the tides. Situated on a private road in historic Squam Heights, on the northern tip of Westport Island, this property delivers unmatched serenity with panoramic water vistas from nearly every room. Designed to showcase its stunning waterfront setting, the home features a bright, open layout ideal for entertaining or quiet reflection. The spectacular Great Room--with vaulted ceilings, a custom fireplace, and expansive windows--opens directly onto a spacious waterside deck, perfect for viewing boats sailing past or dining under the stars. Enjoy the ease of optional single-floor living, an attached garage, and meticulous upkeep throughout. With its elevated position above the shoreline, this unique property also offers rare potential for a deep-water dock--an exceptional opportunity for boating enthusiasts. While blissfully secluded, you are just a few minutes to Wiscasset or Bath and the many attractions of Midcoast Maine. On-island adventures include kayaking, hiking, yoga, and visits to a local farm, organic brewery with outdoor summer events, a historic inn, and a vibrant community association. Furnishings are negotiable, making this a perfect turn-key coastal escape or year-round residence. Residents also benefit from School Choice and Westport Island's low property tax rate. Don't miss your chance to own a slice of classic Maine waterfront living on sought-after Westport Island. Come for a Visit, Stay for a Lifetime...

3 Rocky Rd, Westport Island

Listing courtesy of Engel & Volkers Casco Bay.

$495,000
1662023 MLS
This uniquely elevated property is an ideal setting for boaters of all types, featuring a newly installed dock with a 40-foot float for immediate waterfront enjoyment. This lot offers dramatic easterly views of the Sheepscot River, a short drive from the village of Wiscasset and its charming downtown shops and restaurants - south of the bridge for an easy commute. Extensive clearing and site work have already been completed, creating a ready canvas. Nestled in the established neighborhood of Cushman Point, this property offers a tidal retreat to the west with deep water opportunities to the east. Midcoast Maine living at it's best!

Cushman Point Rd, Wiscasset

Listing courtesy of Legacy Properties Sotheby's International Realty.

$3,495,000
13 Beds ⋅ 14 Baths ⋅ 1630109 MLS
The Gosnold Arms is a classic Maine inn on New Harbor with a total of 5.56± acres, 218± feet of frontage on the harbor, and very good views of New Harbor and out to Muscongus Bay. The property includes the historic inn with ten private guest rooms, a three-bedroom owner's suite, charming public spaces, and potential restaurant space. There are a number of additional multi-unit guest cottages; two cottages (5 units) are located at the water's edge, the others are tucked into the hillside behind the inn in a semi-private wooded setting. The entire property would be suitable for continued commercial use, or it could be converted back to a single-family residence or family compound. The property also has a substantial pier with a ramp and float on New Harbor, a delightful summer community close to a number of desirable attractions, restaurants, and amenities.

146 State Route 32, Bristol

Listing courtesy of LandVest, Inc..

$2,995,000
5 Beds ⋅ 3 Baths ⋅ 1635433 MLS
Built on the Southport's rugged rocky shoreline, this 1920s cottage is loaded with charm and delivers breath-taking ocean views. Updated and well-maintained, the home offers a ground-floor primary bedroom, custom kitchen, an enormous deck, and abundant bedroom and gathering spaces--ideal for hosting friends and family in this quintessential coastal Maine setting. On over an acre of land, the property spans both sides of Bayberry Lane, and includes bold ocean frontage, established gardens, and a garage outbuilding. This opportunity marries classic charm with modern updates in a top tier waterfront setting--a must-see!

7 Bayberry Ln, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$624,900
3 Beds ⋅ 2 Baths ⋅ 1659296 MLS
Perfect setting! Quiet, get away from it all! Walk 10 minutes to the harbor, shopping, restaurants, boat rides and more! Come back home to water views from almost every room! Pull in to your garage and directly enter the big finished open space that can be used in multiple ways. Need and office? Want a family room? How about extra space for guests? Ready for your choices. The unit is appointed with 3 good size bedrooms with oversized closets, 2 full baths , each with double sinks and linen storage. Open concept kitchen and living room allows great space for relaxing and more than enough room for entertaining! Updated kitchen with newer stainless appliances, granite counters, hardwood flooring . Newer slider to big back deck viewing peaceful rock garden area. Plenty of room for outside furniture and plantings. The kitchen center island is perfect for putting out treats, having a little lunch or a quiet cup of coffee. Dining area allows lots of room for oversized table and extra chairs. Large living room plus a newer bow window that looks out directly at Mill Cove waterfront. Step out to the front deck and enjoy private space with even deeper ocean views. Main bedroom with private access to full bath and large closet, is tucked away just steps from the kitchen. 2 additional large bedrooms with views and a second full bath on 3rd level complete this thoughtful floor plan. Good, solid Condo Association in place. New pavement in 2025. Annual fee 4000 per unit , per year. Come for a day - stay for a lifetime!

15 Village Ct Unit 5, Boothbay Harbor

Listing courtesy of Moore-Tuttle & Co. LLC.

$329,000
3 Beds ⋅ 1 Baths ⋅ 1650674 MLS
Experience the quintessential Maine lifestyle in this beautifully renovated ranch, perfectly positioned on a spacious two-acre lot on Westport Island. This single-floor home features an expansive open-concept layout where the sun-filled living room flows seamlessly into a large dining area and kitchen, creating an ideal environment for entertaining and daily living. With three comfortable bedrooms and a full bathroom, the interior feels fresh and modern following a complete top-to-bottom renovation. Peace of mind comes standard with recent upgrades including a brand-new metal roof designed for longevity and low maintenance. Outside, the property offers two level acres with ample room for gardening, outdoor recreation, or simply enjoying the coastal air. Located just a few hundred yards from the Back River, this home provides easy access to the water for kayaking, beachcombing, and sunset strolls. Whether you are looking for a year-round residence or a peaceful island retreat, this property combines modern comfort with the natural beauty of the Midcoast region.

575 Main Rd, Westport Island

Listing courtesy of Coldwell Banker Realty.

$350,000
1657093 MLS
This building is full of possibilities and waits for its next chapter. Originally built as a teen center with a roller rink it was most recently used by a artist and an architect as their own center for creative projects as well as an open concept living space. The building sits on a 14.5 acre lot on the main thoroughfare of the Pemaquid Peninsula and is about 7 miles to the center of Damariscotta and a little over 8 miles to the lighthouse at Pemaquid Point. The main building is 50' wide and 80' and appears to have been originally a single large open space. Currently it is 3 separate spaces with the art studio on the bright south side of the building, a large gallery space in the center and the workshop on the north side with a 12' high garage door. The original building also has a bathroom with a shower.The living space was added on in 2004 and is a large open concept ''studio'' apartment with a full bath and a separate kitchen with lots of cabinets and counter space as well as a pantry area with removable shelving. The building offers all sorts of possibilities where 18' high ceilings, a 12' x 12' door and a 80' by 40' space might come in handy. The separate living space could be used separately as offices or a showroom for whatever you decide to create. Besides the 14.5 acre lot where the building is there is another 20 acre non-contiguous lot that is part of the package.

1443 Bristol & Tbd Split Rock Road, Bristol

Listing courtesy of Legacy Properties Sotheby's International Realty.

$2,495,000
3 Beds ⋅ 3 Baths ⋅ 1655844 MLS
Perched dramatically above the bold Atlantic, this striking midcentury modern architect designed home commands breathtaking views over Johns Bay and the rugged Maine coastline. Offering 3 bedrooms and 2.5 baths, the residence is designed to capture its extraordinary setting at every turn; 367 feet of dramatic, rugged Maine coastline with views that stretch to the horizon!. A soaring great room anchors the home, featuring a floor-to-ceiling stone fireplace accented with rich copper paneling. The family room invites relaxation with expansive ocean views and a cozy wood stove for crisp coastal evenings. A separate living room with a wood-burning fireplace opens to a deck--perfect for morning coffee overlooking the crashing surf below. With two kitchens and multiple gathering spaces, this home is as functional as it is captivating. From its elevated vantage point, enjoy an ever-changing seascape that is nothing short of mesmerizing. A truly enchanting property--offering one of the finest views along the Maine coast. Additionally, there is a shed that also features great views and could easily be converted for a different use, possibly a writer's or artist's studio. This lovely property is just waiting to be reimagined by new owners who will make their own dreams come true in this spectacular setting.

137 Miles Rd, South Bristol

Listing courtesy of Legacy Properties Sotheby's International Realty.

$850,000
5 Beds ⋅ 3 Baths ⋅ 1662132 MLS
VIEWS! VIEWS! VIEWS! The expansive view incorporates so many little islands and a distant harbor and small cluster of moored lobster boats. The soft sounds of the creek are interrupted only by birdsong. This quintessential Maine Coastal Cottage has just been remodeled and appointed in a style that truly brings the feel of the ocean in. The space is both roomy and cozy and is loaded with charm and character with many years of thoughtful design and additions that you just don't see in a newer home. Nearly at the end of a dead end road, you'll find the peace and quiet rarely found in the heart of Vacationland. While the owned frontage is a modest 29' (great for taxes) there is another approx. 50' owned by the Town which appears to be an old boat launch (great for personal use) - all in a perfect little cove. Currently a very successful seasonal rental, it is fully set up for year round use. There is ample space for first floor living with a huge eat-in kitchen, dining room with builtins, living room with a new gas fireplace, large mudroom with laundry, primary bedroom with en-suite bathroom, a second bedroom, a second bathroom, direct entry from the garage, and a covered porch overlooking the ocean! If that wasn't enough, there are 3 more bedrooms & a bathroom upstairs. Two of the bedrooms have adorable twin builtin single sized beds, and the third is a big bedroom with two closets and a built-in dresser. For the boater, you'll find the best places to explore. Located on Hockomock Channel, just north of Greenland Cove in Muscongus Bay, the area is known for it's fishing, Island preserves and beauty. The Town Landing is the next road over, the Lusty Lobster is a short walk or paddle away where you can grab lunch on the dock. Within a 20 min drive is the Golf Club, Pemaquid Beach & Lighthouse, and many restaurants and gift/art galleries. Home has been used seasonally since 2BR septic was installed. Whole house generator. Please read picture captions!

24 Creek Rd, Bremen

Listing courtesy of Bay Watch Realty, LLC.

$3,995,000
5 Beds ⋅ 7 Baths ⋅ 1658081 MLS
Situated on 7 private acres, 18 High Head blends expansive saltwater frontage with newly renovated contemporary comfort. Completed in 2024-25, this comprehensive reconstruction transformed the property into a modern four-season masterpiece. Every detail was considered to ensure beauty, performance and year-round comfort. This fully furnished home boasts 320 feet of pristine deep-water frontage and includes a charming new guest house. Enjoy the working lobster boats, harbor seals, dolphins, and bald eagles making the setting a favorite for yachts, kayakers and fishermen. The main house features exquisite design elements including 2 flights of custom floating stairs, a 30' natural stone fireplace, a new open kitchen, 3 bedrooms, 3.5 bathrooms and 12 heating/cooling zones. New doors and a wall of windows throughout capture natural light and water views at every turn. The first-floor primary suite offers a sitting room, gas fireplace, bath and bedroom, all with sweeping water views. The first level also includes a new 80' waterfront deck, dining area, kitchen island, laundry, mudroom and media room. An upper-level ensuite bedroom overlooks the courtyard. A lower-level suite includes a bedroom with bath, den and patio, all with water views. The fully furnished 2-bedroom, 2.5 bath guest house has private entry leading to a lower-level living area with half bath, gas fireplace, deck and a bedroom made private with barn doors. The second level features a well-appointed eat-in kitchen with island, living area with private waterside deck, gas fireplace, 2 full baths, laundry and bedroom. High Head has 1000' of new paved driveways, extensive stonewalls and patios, and scenic carriage path to a new deepwater dock. Enjoy the perfect balance of seclusion and accessibility to shopping, dining, botanical gardens, golf, and hiking all nearby, situated in the heart of Midcoast Maine, minutes from Boothbay Harbor, Damariscotta, Wiscasset, 70 minutes to Portland Jetport.

18 High Head Rd, Edgecomb

Listing courtesy of Legacy Properties Sotheby's International Realty.

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