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$975,000
3 Beds 2 Baths 1667304 MLS
An extraordinary private compound on Boyd Pond in Bristol, where 15 of 18.5 acres are held in permanent conservation easement--ensuring this sanctuary remains protected in perpetuity. Over 800 feet of undisturbed shoreline. Two thoughtfully designed buildings. Complete privacy. This is legacy real estate. The main residence contemporary design is oriented to maximize pond views and natural light. The first-floor primary suite features a private ensuite bath, walk-in closet, and adjoining wellness room with a resistance swimming pool. Two additional bedrooms on the upper level share a full bath. Open-concept kitchen, dining, and living space flows onto a screened porch overlooking Boyd Pond. Lower-level family room with kitchenette offers flexible space for guests or extended family. Two-car attached garage with direct entry to mudroom and laundry. ''Tree Top'' is a detached two-story structure with first-floor office and two rooms and full bath on the second floor. A second-floor deck overlooks the surrounding forest. Ground-level single-car garage accommodates kayaks, canoes, and outdoor equipment. Ideal as guest quarters, creative studio, or private home office. Bristol offers quintessential midcoast Maine: working harbors, conservation lands, and a tight-knit community without tourist congestion. Pemaquid Point, Colonial Pemaquid, and the Damariscotta River are minutes away. Portland International Jetport is approximately one hour. This property represents an increasingly rare opportunity: significant private acreage with water frontage and permanent conservation protection. For buyers seeking a retreat that will endure unchanged, this Boyd Pond sanctuary delivers.

227 Quail Run Rd, Bristol

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,299,000
2 Beds 3 Baths 1666968 MLS
Waterfront property on Damariscotta Lake set on 2.19 private acres with 210 feet of deep-water frontage PLUS an additional buildable adjacent lot. This property enjoys unobstructed lake views and a premium dock system providing easy access for boating, swimming, and recreation. Included with this listing is a buildable lot with 150' of owned water frontage. The 1984 home offers a 3 season room with deck below to capture the beauty of the lake from multiple vantage points. A spacious 30' x 40' garage offers abundant storage for vehicles, boats, and lake toys. Whether you're seeking a year-round residence or a seasonal retreat, this property combines privacy, expansive waterfront, deep-water access, and stunning views in one of Midcoast Maine's most desirable lakefront settings. Flexibility abounds with the additional lot!

74 Lincoln Ln, Newcastle

Listing courtesy of Blue Lobster Real Estate.

$2,800,000
6 Beds 4 Baths 1666629 MLS
Built in 1917 by John Aspinwall, this extraordinary retreat is among Mid-Coast Maine's most exceptional private island properties. Set on a secluded 95-acre peninsula with 3,809 feet of waterfront, the estate enjoys sweeping views of Flying Passage and Muscongus Bay, offering remarkable privacy, natural beauty, and maritime charm. A haven for boaters and sailors, the property features a deep-water dock, granite pier, and new mooring with outstanding access to surrounding waters and islands. Thoughtfully renovated, the historic main residence preserves its architectural character while incorporating modern comforts. At its heart is a magnificent living room with an oak-truss cathedral ceiling and a dramatic 12-foot stone fireplace. A glass-enclosed sun porch captures panoramic water views, while expansive decks overlook the private beach and rugged shoreline. The home offers four bedrooms, including a serene primary suite with a double-sided fireplace, sitting room, and spacious en-suite bath. A well-appointed country kitchen with a butler's pantry is ideal for both everyday living and entertaining. A substantial barn, built in 2007, includes a beautifully finished year-round guest apartment with private deck overlooking the cove. Two charming shorefront cottages nestled among the evergreens further enhance the compound - a cozy sleeping cottage with a stone fireplace, the other a game room with potential for additional guest accommodations. Exceptionally self-sufficient, the property is supported by an artesian well and professionally installed solar, electrical, and generator systems, providing the reliability of a mainland residence. Satellite television and internet service ensure modern connectivity. Offered fully furnished and equipped, including a 2019 18-foot Parker center console with a 115-hp Yamaha engine, Aspinwall presents a rare opportunity to own a legacy Maine island retreat designed for gathering, recreation, and generations of unforgettable summers.

16 Bremen Long Is, Bremen

Listing courtesy of Legacy Properties Sotheby's International Realty.

$3,950,000
3 Beds 3 Baths 1666204 MLS
Available for the first time in a quarter century, this rare coastal retreat encompasses 51 private acres with nearly a mile of frontage along the Sheepscot River. Step back in time as the meandering dirt drive, lined with mature oak trees and vintage stone walls, draws you to the meadow's edge and sweeping views of the river. Over 40 acres of your own private, magical wooded trails wander down the peninsula to a rocky point where seals frolic offshore and bald eagles perch above the water. Heading toward the water, you will pass the writing cottage, saltwater pool, and pool house. Next is the 3-bedroom, 3-bath antique Cape house from the 1800s, thoughtfully updated to honor its heritage while providing modern amenities. Exercising judicious design restraint, the owners added a new kitchen, upgraded the pantry, and refreshed all three bathrooms. The new heated saltwater pool and its pine-scented pool house offer hours of entertainment for all ages. The second writing studio, designed by Snyder and Cheng, sits at the water's edge, offering a quiet space for music, writing, storage, or creative retreat. The deepwater dock, a coveted feature for boaters, offers 8 to 9 feet of depth at mean low water and will welcome most boats. Vessels requiring more depth can swing on the mooring at 28 feet. The protected waterfront also invites quieter days on the water, offering easy access for kayaking, canoeing, and exploring the Sheepscot River at your own pace. Boaters can enjoy a remarkable network of rivers, coves, and island passages, with easy access to open water and the sea beyond. A true legacy offering with thoughtful conservation easements to ensure its quality for generations. The current owners chose understated simplicity, allowing the natural setting to remain the defining luxury: woods, wildlife, salt air, and the ever changing tides of the saltwater river. This coastal sanctuary is just an hour from the Portland, Maine airport and 2.5 hours from B

45 Bradley Rd, Westport Island

Listing courtesy of Vitalius Real Estate Group.

$689,000
3 Beds 2 Baths 1666196 MLS
Are you ready to enjoy the summer at the lake? Light, bright, spacious & updated ranch with dock on peaceful Dyer Long Pond, one of the best kept secrets in Lincoln County. With the acreage across the lake in conservation, the property will remain surrounded by beautiful unspoiled nature. Listen to the loons in the morning while you sip your morning coffee on the dock bench. Later, grab your suit and towel for a refreshing swim in the lake, or jump in your kayak or boat to explore the 3 mile long lake. Inside the house, the open plan kitchen & large island, dining area, and living room is the perfect spot for hosting friends and family. The wood burning stove makes it cozy on cool evenings. The primary bedroom has a large window looking out to the lake and an attached bathroom with shower and built ins. 2 other bedrooms share another bathroom with a tub/shower combo. Downstairs, a finished space could be a great family room, gym, or home office. There is also a 2 car detached garage with a built in workbench. Decks and porches on 3 sides of the house give lots of options for enjoying the natural surroundings. On Dyer Long Pond and close to Damariscotta Lake & Clary Lake, as well as shops & restaurants in Damariscotta & Newcastle, this property has everything needed to enjoy the scenic Mid-Coast area.

102 Trask Ln, Jefferson

Listing courtesy of Peninsula Properties.

$665,000
2 Beds 1 Baths 1666149 MLS
Seize this rare opportunity to own a year-round retreat on the shores of highly sought-after Damariscotta Lake. Tucked away at the end of a private road, the year round two-bedroom cottage offers a peaceful sanctuary where you can relax to the gentle sounds of nature. This home features an open floor plan in the main living area, complemented by a functional mudroom, two bedrooms, and a full bathroom. You can enjoy direct lake views from the living room or step out onto the back deck, which runs the entire length of the cottage and offers an ideal spot for watching sunsets over the water. The property is well-equipped for waterfront living, featuring a private dock and a handy ''gear'' hut located right at the water's edge. For storage, an additional outbuilding is available for gardening supplies or other items. After spending a day on the lake, the lakeside firepit provides a perfect setting for relaxing during cool summer evenings. Enjoy complete structural peace of mind with extensive recent capital improvements, including a new roof (2017), a modern septic system (2023), a brand-new radon mitigation system (2026), and newly buried power lines (2026) that protect your utility access while preserving unobstructed natural views. While offering total privacy, this lakeside gem perfectly positions you to enjoy the very best of Mid-Coast Maine. You are just minutes from the historic twin villages of Damariscotta and Newcastle, renowned for their vibrant local shops, fresh oyster bars, and charming restaurants. Beyond the lake, you are a short drive from coastal harbors, scenic hiking trails, and the rugged Atlantic coastline, making this the ultimate basecamp for year-round Maine adventures.No DRIVE-BYS! Appointment only.

58 Roberts Rd, Nobleboro

Listing courtesy of Camden Real Estate Company. info@camdenre.com

$1,420,000
3 Beds 4 Baths 1665269 MLS
Delightful end-of-the road privacy along the shores of Knubble Bay, mid-coast Maine's sought-after saltwater getaway, boasting protected deep water, unrivaled privacy, and mesmerizing sunsets. Enjoy your favorite drinks as the sun paints the sky each evening, the perfect backdrop to the boats that wait patiently on your moorings. A contemporary home anchors this legacy property from atop an island-like hilltop and boasts first floor primary suite, solarium, greenhouse, and a great room whose ceiling vaults up above a grand fireplace and soaring fenestration. Relax your gaze into the fireside after a voyage out to Damariscove Island and back. Experience the endless adventures of the Sheepscot, Kennebec, and Damariscotta rivers from this central boating outpost with numerous restaurants within a short boat ride! A proper pier and dock system provide an oversized, piling-protected float and three very stout moorings just serviced. Your solitude is assured with over 15 acres of forest, an undeveloped waterfront lot, nearby guest cottage, three-bay garage/workshop, and more. Buyer will need to install new septic field to replace the existing overboard discharge system. Call now for a private showing.

119 Knubble Bay Rd, Westport Island

Listing courtesy of Sharon Drake Real Estate, Inc.. 207-443-4444

$124,900
1665323 MLS
Discover the perfect blend of privacy, nature, and waterfront living with this exceptional 22± acre wooded parcel featuring 165 feet of frontage on Turner Pond. Tucked away on a private road, this property offers a rare opportunity to create your dream homestead, seasonal retreat, or recreational getaway. Surrounded by mature trees and abundant wildlife, the land provides a peaceful setting with plenty of room to explore, hike, hunt, garden, or simply enjoy the beauty of Maine's outdoors. The waterfront offers direct access to Turner Pond for fishing, kayaking, canoeing, and year-round enjoyment. Whether you're seeking complete seclusion, a future homesite, or an investment in a unique waterfront property, this expansive parcel offers endless possibilities. Experience the tranquility of country living while remaining within convenient reach of nearby amenities.

109 Colomy Ln, Somerville

Listing courtesy of Black Duck Realty.

$399,999
1664403 MLS
A beautiful waterfront setting along the Sheepscot River in Midcoast Maine, with a distinct sense of privacy and natural beauty. This land is situated within Rum Cove on Westport Island. The property includes 3.3 acres with 300' of pristine river frontage. It captures expansive views over the Sheepscot River leading to Boothbay Harbor and the Atlantic Ocean. Bordering conservation land, it provides a quiet sense of escape, with native wildlife including eagles, osprey, and deer. Build your own private dock or owners enjoy access to a shared deepwater dock and float in Rum Cove, providing access to boating, kayaking, fishing, and exploration along the Sheepscot River. Well suited for a custom waterfront home or coastal retreat, this property balances seclusion and accessibility. Though peacefully tucked away, it is just minutes from the town of Wiscasset for groceries, dining, and everyday needs, with convenient access to Bath, Brunswick, Portland, Augusta, and the greater Midcoast region. A place where it's easy to imagine making this your own.

16 Otter Ln, Westport Island

Listing courtesy of LAER.

$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.

$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.

$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.

$550,000
3 Beds 1 Baths 1654804 MLS
Escape to your own lakeside retreat with this inviting three-bedroom cottage, designed for relaxation and outdoor enjoyment. From spring through fall, you'll love spending your days on the water--swimming, fishing, kayaking, or paddleboarding--and your evenings gathered with family and friends. Enjoy peaceful nights on the screened porch, where you can listen to the call of the loons and take in the soft evening breeze off the lake. When it's time to unwind, the firepit area offers the perfect spot to share stories and make s'mores under the stars. Inside, the cottage offers a cozy and comfortable layout ideal for lakeside living. The open living area creates a welcoming space to relax, dine, and enjoy the view, while the three bedrooms provide plenty of space for guests or family. Step outside to a large, gently sloping lawn that leads right down to the waterfront--perfect for picnics, games, or launching a canoe. Whether you're sipping your morning coffee as the sun rises over the lake or watching the reflections of autumn colors dance on the water, this property captures the beauty and tranquility of Maine's lake life. This cottage is move-in ready and waiting for you to start making memories. Don't miss the opportunity to make your dream of life by the water a reality!

3 Tackle, Jefferson

Listing courtesy of Black Duck Realty.

$310,000
1662777 MLS
Tucked away in the natural beauty of the Boothbay Region, this new subdivision offers a rare opportunity to own one of four thoughtfully positioned wooded homesites, each designed for those who value privacy, space, and refined coastal living. Set among mature trees and gently rolling terrain, these expansive lots provide the perfect canvas for a custom-built residence. Each parcel offers generous acreage, allowing for secluded home placement, curated landscaping, and the freedom to create a truly personal retreat. Whether you envision a modern architectural statement or a timeless Maine cottage, the setting supports both elegance and tranquility. Located a short drive from Boothbay Harbor's restaurants and shopping, yet removed enough to ensure peace and quiet, this enclave strikes a balance between accessibility and retreat. A part of the sought after Bel Acres neighborhood off Annable Road, along with the formation of the Midden Ridge homeowner's association. A beautiful private road and underground utilities to each carefully planned lot preserve the natural surroundings while offering building convenience. Soil testing has been completed at each site.

Lot 2-B Midden Ridge, Boothbay

Listing courtesy of Legacy Properties Sotheby's International Realty.

$219,000
1 Beds 1 Baths 1652929 MLS
Waterfront Studio -- Fully Furnished, Ground Level Convenience Enjoy effortless waterfront living in this beautifully updated ground-level studio at The Lodge at Sheepscot Harbour Village Resort. Being sold fully furnished, this turnkey unit offers the perfect opportunity for a personal retreat, investment property, or low-maintenance coastal getaway. Thoughtfully refreshed with new furnishings, a new PTAC heating and cooling unit, and top-down/bottom-up blackout shades, the space blends comfort, efficiency, and modern convenience. Large windows frame peaceful water views, bringing natural light and the beauty of the harbor right into your living space. Step outside your door to a walk-out patio area with direct access to the resort's shared waterfront amenities, including the common dock and waterfront fire pit -- ideal for relaxing, entertaining, or enjoying Maine's coastal lifestyle with potential for a dock slip or mooring. Located within a sought-after community, this unit offers easy, carefree ownership with strong rental potential and year-round enjoyment with convenient access to Wiscasset, Boothbay Harbor and the Twin Villages of Damariscotta- Newcastle. (Some personal items shown in photos are not included)

304 Eddy Rd Unit 202, Edgecomb

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.

$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.

$750,000
2 Beds 3 Baths 1653423 MLS
Stunning Kennebec River waterfront in Dresden. Enjoy exceptional Kennebec River frontage in the charming town of Dresden. This contemporary-style home built in 2006, with on demand generator and attached two car heated garage offers two spacious bedrooms, two full bathrooms and a convenient half bath. Inside, you will find vaulted ceilings, radiant heat, and beautiful custom woodwork throughout. The Kitchen features maple cabinetry, tile floors, and quality finishes that blend warmth and functionality. Expansive windows bring the river views indoors, creating a peaceful, light filled living space. Step outside to your private dock and float, perfect for boating, fishing, or simply relaxing by the water. A separate heated two-story barn with finished space on the second floor located across the street provides excellent additional storage or potential for future expansion. A rare opportunity to own premium Kennebec River frontage located on the Western Shore to enjoy the sunsets, with comfort, style, and space in picturesque Dresden.

381 Cedar Grove Rd, Dresden

Listing courtesy of McAllister Real Estate.

$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.

$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.

$1,550,000
3 Beds 3 Baths 1656253 MLS
Surveyed and possible for one to take through the subdivision process!! Set on an extraordinary 41+/- acres lot with approximately 1700 feet of frontage on the Eastern River, this Dresden property offers a rare blend of privacy , waterfront living and versatility. The 3-bedroom , 2.5 bathroom single-family home spans 1796 square feet and is thoughtfully designed to take advantage of its natural surroundings. There is also a walkout basement which may be finished for more living area. Included is a new floating dock with aluminum ramp ready to place on the river for summer time enjoyment. A standout feature of the property is the four-bay outbuilding , perfect for equipment storage , hobbies , boats or a home-based business operation. With acres of woods and extensive water frontage the land invites endless possibilities. An additional 5.8 acre lot to the North with 384' of water frontage is also available if entire deeded land of owner is desired.

886 Middle Rd, Dresden

Listing courtesy of Cromwell Coastal Properties. (207)208-9311

$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.

$649,000
3 Beds 3 Baths 1662713 MLS
This custom ranch offers refined one-floor living with three bedrooms and two and a half bathrooms, blending comfort, privacy, and understated elegance. Thoughtfully designed, the layout places the owners' suite on one end of the home, creating a peaceful retreat, while separate accommodations on the opposite side welcome family and guests with ease. Wood floors extend throughout, and a cathedral ceiling paired with an open-concept design fill the home with natural light and a wonderful sense of warmth and openness. Designed for effortless living, the property also features an attached two-car garage, a dedicated workshop in the basement, and a serene 1.19-acre setting that invites both relaxation and quiet enjoyment. Just minutes away, a public boat launch makes it easy to spend the day boating or kayaking, while the Trevett Store offers the simple pleasure of a classic coastal Maine lobster roll. With Coastal Maine Botanical Gardens and Boothbay Land Trust nearby, this home places you close to the natural beauty, charm, and coastal lifestyle that make the Boothbay Region so special.

23 Sunny Acres Ln, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$849,900
2 Beds 2 Baths 1656076 MLS
Your private waterfront retreat awaits. Nestled on 14± acres with 513 feet of owned frontage on the Eastern River in the desirable town of Dresden, this rare property offers unmatched privacy and natural beauty. The home sits on a peninsula with breathtaking 180-degree views up and down the river. The land offers multiple potential building sites--ideal for a private compound or development--or simply enjoy it all to yourself as your own peaceful escape. Additional features include a farm pond, attached 2-car garage, separate barn, and a long driveway set nearly 1,000 feet off the road. Inside, you'll find a first-floor bedroom, soaring cathedral ceilings, and a second-floor bedroom with a private bath. Enjoy the outdoors from the gorgeous patio and hot tub and rest easy with the automatic generator. Potential for a deep-water dock adds even more value. A truly special property--schedule your showing today!

691 Middle Rd, Dresden

Listing courtesy of Rizzo Mattson. 207-622-9000

$995,000
2 Beds 1 Baths 1655570 MLS
Henry David Thoreau viewed transcendence as... a lived, daily experience achieved by immersing oneself in nature, practicing deliberate living, and fostering solitary reflection to connect with a higher divine unity. Thoreau advocated for ''living awake'' by stripping away societal materialism to ''suck out all the marrow of life,'' finding spiritual significance in natural beauty. If this resonates with the way you would like to live, then you will fall in love with 59 Greenland Cove: set in a natural sanctuary dotted with the clarion call of birds, marine life and the deep tradition of Maine's lobster fishermen just feet from the ocean-facing deck. Like a bride on her wedding day, this property includes something old, something new, something borrowed and something blue... Traditional, old, and unspoiled Maine remains the focal point of this beautiful coastal Bremen home. Newly reimagined and rebuilt upon the borrowed (and rock-solid!) foundation of its original structure, now boasts of a beautifully designed and energy-efficient interior that thoughtfully incorporates natural building elements like wood, steel and stone throughout. Wide, sunny windows wrap around the home maximizing views of a vast blue Maine ocean and all the wildlife that abounds. Only the brilliant canopy of stars breaks the silence, their light like a quiet conversation. A residence defined by its gentle charm and complete seclusion; equal parts sweetness and solitude.

59 Greenland Cove Rd, Bremen

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,199,000
4 Beds 4 Baths 1643400 MLS
Tucked into idyllic Butter Point in Waldoboro, this waterfront retreat feels like a secret you've been let in on. The original 1997 cottage is all Maine charm - a stone fireplace, warm knotty pine, and cozy gathering spaces that frame the water just beyond the windows. In 2020, a thoughtful addition was crafted to mirror the classic lines of the original structure while quietly elevating everything with modern, luxury finishes. The result is a seamless blend of old and new: expansive glass that floods the home with natural light, elevated materials throughout, and sightlines that pull your eye straight out to the Medomak River where the Narrows open toward Broad Cove. Massive windows run the length of the waterside elevation, making the tide, sky, and ever-changing light part of the daily rhythm of the home. Whether you're curled up by the fire, gathered around the table, or stepping out with your morning coffee, the connection to the cove is constant and effortless. Outside, the property lives just as large. A substantial barn offers storage for up to four vehicles or boats, gear, and workshop space, which could also be converted to a large apartment for your Airbnb visions. The space is further complemented by ample parking below the house and an additional small garage tucked out back. It's the ideal setup for someone who wants a refined coastal home without sacrificing room for projects, toys, or hobbies. From the handcrafted feel of the original camp to the elevated comforts of the 2020 expansion, this Butter Point property is that rare combination of character, privacy, and truly unforgettable water views—ready to be enjoyed in every season.

101 Butter Pt, Waldoboro

Listing courtesy of Pooley Realty Group. jessicapooleyrealtor@gmail.com

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