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Explore Our Maine Homes for Sale with Guest Cottages

A detached space for guests that includes its own entrance, full bathroom, and kitchen or kitchenette, is a popular selling point for buyers in Maine. A separate guesthouse helps hosts offer high-end hospitality to their visitors, whether it’s extended family, friends, or other guests. This list of Maine homes for sale with inviting guest cottages, ranging from a 35-acre island estate, a historic Kennebunkport property, and an expansive Bar Harbor compound, will allow your guests to unwind in seclusion and style.

135 Mountain Arrow Drive, Camden, Maine

Offered at $8,500,000
Listed by Brian Wickenden

Set on over 18 acres of private land with gardens overlooking Camden Harbor and the islands of Penobscot Bay, this expansive estate is an ideal year-round oasis. The stunning main house offers a home theater, rec room, sauna, exercise room, wine cellar, and infinity pool, and the beautifully appointed one-bedroom guest cottage has a 2-car garage and attached greenhouse. The cottage includes a kitchen, dining and living areas, and features central air conditioning and radiant heat, as well as spectacular craftsmanship and detailing. It looks over a pond and down to the main home with distant views out toward Penobscot Bay. Learn more about this Camden estate here. 


254 Drexel Lane, Islesboro, Maine

Offered at $3,695,000
Listed by Jackie Wheelwright

This one-of-a-kind 35-acre estate on Islesboro has over 3,900 feet of shorefront and a private beach. The stunning 9,000 sq ft main house has countless amenities including eight bedrooms, a swimming pool, a wine cellar, a bright solarium with radiant floor heat and fireplace for enjoying year-round. The separate 2,200-sq-ft guest house has 3-4 bedrooms and a three-season enclosed porch and deck looking out to the sea and backyard. The property’s rustic heated barn also has an upstairs 2-bedroom apartment, offering expansive rental potential or room for large gatherings. Learn more about this island estate here.


238 Hallowell Road, Pownal, Maine

Offered at $2,695,000
Listed by Marika Clark

This extraordinary 21-acre equestrian estate in Pownal includes a 5,000 sq ft main house, a carriage house, guest house, stables, multiple paddocks, and an Olympic-level riding arena, all nestled in a bucolic setting along the east branch of the Royal River. The guest cottage, with its own garage, offers privacy and contains a beautiful open concept living area with exposed beams and hardwood floors throughout, a lovely gas-burning stove, beautiful built-ins, and a second-floor bedroom and full bathroom. Learn more about this equestrian estate here. 


10 Chestnut Street, Kennebunkport, Maine

Offered at $1,999,999
Listed by Randal Simon & Rosane Hirschy

Known as the John Bourne house, this historic property built in 1806 has been renovated over the years to create the perfect blend of antique charm and appeal. Just a two-block stroll to Dock Square in Kennebunkport, the home has a free-standing guest house, plus six fireplaces, new flooring, air conditioning, high-quality kitchen appliances, and other modern upgrades. The cottage offers a gas fireplace, kitchenette, full bath, and loft. Learn more about this historic Kennebunkport property here.


42 Thomas Bay Lane, Bar Harbor, Maine

Offered at $1,900,000
Listed by Carroll Fernald & Susan Allen

This gorgeous property in Bar Harbor features three dwellings set on 10 acres, perfect for a family compound, guests or vacation rentals: the main 3-bedroom house, a 1-bedroom guest cottage, and a 2-bedroom apartment over the detached garage. Amenities include lovely perennial gardens, a bright sunroom, a sauna, and a wine cellar. Learn more about this beautiful Mount Desert Island property here.