Welcome to the Winthrop Lakes Region, prized for its aesthetic beauty, fisheries, wildlife, recreational and cultural resources. Sited on the Eastern shore of Lake Annabessacook, in a rural and largely undeveloped area, you'll find 273 pristine and recently conserved acres and 3,600 feet of shore frontage formerly farmland in the Woolworth Estate. Included is a contemporary home built in 2010. The carefully designed home and its setting offer the finest combination of quiet and convenience, modernity and co-existence with a vibrant landscape of unmatched beauty in all seasons. With fields to roam, woods to explore, gardens to plant, boating, swimming, and trails to hike or snowshoe, the options for outdoor enjoyment from this scenic spot are abundant! Comfort and energy efficiency are hallmarks of the 3 bed open floor plan custom home boasting one-floor living, solar power, on-demand, propane furnace, whole-house generator, wood stove for ambiance, security system and more. The warmth of radiant heat, sunlight and the Douglas Fir wood trim of the first floor invite you to linger in the sun-filled living room overlooking the peaceful landscape. The owners' suite, with an updated bath, adjoins a convenient office. The large mud room with laundry connects to the two-car garage and root cellar. The 3-season sun porch and large patio, offering verdant pasture and forest views, provide plenty of space for gatherings. Upstairs, two bedrooms, a full bath and a spacious loft will appeal to guests. There's more to be found in the nearby 30x42 barn for housing all your equipment and recreational gear. There is also the option to build a waterfront cottage up to 1,800 sqft. Managed in partnership with Kennebec Land Trust under the terms of a conservation easement, 39 Macomber invites you to explore the possibilities at this jewel of the Lakes Region!

Enjoy end of the road privacy on this 1.95-acre waterfront lot in the small and well-kept Western Ledge subdivision. Comprising a peninsula, the property features 900'+ of protected frontage with a deep water dock and outstanding Damariscotta River views. The 1998 home offers three floors of living space, including two ensuite bedrooms, open concept kitchen/living/dining, and unique spaces that include a sun room with vaulted ceiling, hot tub room, expansive decking, and a finished basement. A short drive to downtown Boothbay Harbor, the Boothbay Harbor Country Club, and other area attractions.

540 feet of water frontage on Long Lake! Set on 2 private acres, this brand-new, custom-built contemporary home offers an exceptional lakeside lifestyle. Spanning three levels with soaring 25-foot ceilings, the home features a spacious main floor great room, where a custom kitchen seamlessly flows into the living and dining areas, all framed by expansive commercial grade triple-pane windows with aluminum screens showcasing stunning lake views. High speed internet access is available through Starlink. Step out onto the oversized 16' x 40' deck, perfect for entertaining or relaxing, located just off the great room and adjacent to the luxurious primary suite, complete with walk-in-closet and a steam shower. Upstairs, you'll find two generous bedrooms sharing a full bath. The walkout lower level includes two large versatile rooms ideal for a family room, game room, office, bunk room—whatever suits your needs—along with a full bath and mechanical room. Comfort is ensured year-round with nine high-efficiency heat pumps as well as a whole house water filtration system. Enjoy panoramic lake views and direct access via a large private dock. Located on secluded Zakelo Island, this rare retreat is part of an exclusive enclave of only six homes, just a quick 2-minute boat ride from the mainland dock and parking area.

Welcome to 26 West, one of Maine's most spectacular private mountain estates. The property gets its name because you look out over 26 mountain peaks to the west. Set on 168± acres in the heart of Bethel, Maine. This extraordinary 5,300± sq ft chalet offers rustic elegance, modern comfort, and the ultimate in privacy, making it the perfect vacation home or legacy family compound. Crafted with natural wood and stone, 26 West offers five spacious bedrooms, and five baths provide room for gathering and quiet retreat. The great room features a dramatic 28-foot-high wall of windows that floods the space with light and showcases the view of as many as 26 mountain peaks. A large west-facing wraparound deck offers amazing outdoor space for entertaining, as well as a full bar, billiards, a 12-seat home theater, and a sauna and a hot tub for year-round relaxation. The 168± acres offer a mixed forest and meadows. There are also two stocked ponds, a small orchard, five ski and sledding runs cleared starting at the ridgeline with an elevation of 1860'. Located minutes from the vibrant village of Bethel known for its rich history, welcoming community, and easy access to Sunday River. Enjoy skiing, hiking, mountain biking, golf, and some of New England's best fall foliage right from your doorstep. 26 West is being offered furnished.

Overlooking highly coveted Rockport Harbor, 11 Mechanic St. is Maine coastal living at its finest. This architect-designed contemporary residence has westerly views of the harbor from nearly every room. Step from your backyard onto your private dock, ready to explore the sailor's paradise of Penobscot Bay. Multiple decks and elegantly designed grounds create the perfect setting for entertaining or taking in sunsets over the water. The four to five-bedroom layout offers ample space for family and guests. Unwind in the inviting theater room, soak in the sun in the solarium, or read a book by the fire in the living room with the ever-changing harbor in full view. Situated in one of Maine's most prestigious neighborhoods, you'll find yourself a stone's throw from the restaurants and galleries of Rockport village and the peaceful and scenic trails of Beauchamp Point. Walk down the street for a morning workout at the YMCA or for a tee time at the private Megunticook Golf Club, both less than a mile away. Property to be split at close. Acreage to convey is roughly .48 acres and includes house, pier, generator and all improvements.

Live, Work, Invest — Premium 8-Unit + Heated Warehouse in Biddeford, Maine. A rare opportunity to own a high-performing, mixed-use property in one of Southern Maine's fastest-growing and most desirable cities. This exceptional two-building compound offers eight well-maintained residential units, including a beautifully updated owner's suite with a fireplace—ideal for executive rental, owner-occupancy, or maximizing rental income. What truly distinguishes this offering is the heated warehouse—a premium feature seldom found in today's market. With four oversized overhead bay doors, it's tailor-made for contractors, tradespeople, collectors, or entrepreneurs needing secure, high-end space. Whether you envision a luxury car vault, artisan workshop, small business HQ, or a sophisticated live/work lifestyle, the flexibility is unmatched. Professionally landscaped with ample paved parking, the property presents a clean, polished curb appeal that reflects pride of ownership. With a strong rental history, recent upgrades, and low-maintenance systems, this is a strategic asset for investors or business owners who value versatility, quality, and location. For the discerning buyer ready to combine lifestyle, income, and long-term value—this is where it all comes together.

This captivating waterfront property at 31 Viking Trail, Surry, is ideally situated between the Blue Hill Peninsula and Mount Desert Island. A year-round retreat, it offers breathtaking water views, stunning vistas of Acadia National Park's mountains, a beach with deep-water access, and serene pastoral surroundings. Enjoy spectacular sunrises and sunsets from a variety of outdoor spaces, including a screened porch, a spacious front porch, a patio, multiple decks, and the primary suite's sunroom. Thoughtfully designed landscaping enhances the natural beauty, creating a tranquil and inviting setting. Inside, the open-concept living area is designed to maximize the dramatic views. The upper level features a grand foyer, a custom gourmet kitchen with a large pantry, a separate wet bar for entertaining, and a great room with vaulted ceilings, a wood-burning fireplace, and access to the upper deck. This level also includes a laundry room with built-in cabinetry, a luxurious primary suite with a gas fireplace, a walk-in closet, a soaking tub, and a separate shower, as well as an office and a guest bedroom with an en-suite bath. The lower level offers a spacious great room with a wood stove and walkout access to the lower patio, four additional water-view bedrooms, three full baths, a utility room, and a generous storage area. This six-bedroom, five-and-a-half-bath custom-built residence showcases exceptional craftsmanship and attention to detail, all while embracing its spectacular location on the shores of Patten and Union River Bays.

1588 Turtle Head Road is a premier waterfront retreat with stunning western views across Turtle Head Cove and Penobscot Bay, back towards Belfast and the Camden Hills. The property includes a beautifully renovated mid-century modern home with two bedrooms and a spacious, open floor plan designed to capture natural light and maximize the water views. There is also a versatile garage/barn with a fully redone one-bedroom guest apartment above, perfect for hosting extended family and friends. Recent improvements can be found throughout the property, including a new sauna, and it has been very well-landscaped with lawn and gardens, professional stonework, and 328± feet of shorefront with a sand and pebble beach area. An all-new, granite deep-water pier with three moorings - a two ton, a four ton, and a six ton appropriate for a 100-foot sailboat - make this an ideal island retreat with convenient access to the mainland and the excellent boating in Penobscot Bay.

85 Provost Road is an excellent lakefront property with 3.02± acres on a point of land and offering exceptional panoramic views over Damariscotta Lake. The property includes a contemporary-style house with comfortable living spaces and eight spacious bedrooms, ideal for hosting summer gatherings with extended family and friends. The year-round home has been expanded over time and the heart of the home is an open living room with a vaulted ceiling, a two-story stone fireplace, and several doors open to a wraparound deck and a lovely screened porch. Recently renovated, the kitchen seamlessly opens to living areas on two sides, and was thoughtfully designed for entertaining with multiple appliances and an expansive kitchen island. The formal dining room offers an elegant setting for large family meals and a cozy sitting area is centered around a charming stone fireplace. The property includes a detached, two-bay garage and the landscape is mostly wooded with wonderful outdoor living areas and 769± feet of shorefront. Two dock systems, one for boats and swimming, and the other designed for convenient kayaking, ensure maximum enjoyment of the lake and Maine's quintessential summer activities. Additional, adjacent parcel of undeveloped land is available with 2± acres and 304± feet of shorefront.