Homes are often at their best when they bring people together. Summer is no exception. Guest houses, cottages, and separate living spaces create opportunities to welcome family and friends while offering the comfort of privacy and independence. Whether hosting holiday weekends, accommodating visiting relatives, or creating space for multiple generations, these homes are designed to adapt to every stage of life.
Thoughtfully integrated guest accommodations extend the way a property can be enjoyed. From charming cottages tucked among the trees to beautifully appointed guest suites overlooking the coast, these spaces offer flexibility without compromising comfort or connection throughout the summer season.
Discover a curated collection of homes across Maine where guest houses, in-law suites, and separate living spaces create room to gather, host, and make lasting summer memories.
93 Cooksey Drive, Mount Desert, ME 04660
Represented by Bill Gaynor
Offered at $13,500,000
Nestled within the coastal village of Seal Harbor, Wanakiwin enjoys a secluded woodland setting overlooking 780 feet of dramatic Atlantic frontage. Designed for gathering across generations, the estate also includes three-room guest quarters that provide additional space for family and visitors.
402 Baker Hill Road, Freeman Twp, ME 04983
Represented by Glenn Jonsson & Marika Clark
Offered at $4,500,000
A Stunning Four-Season Retreat Just 30 Minutes from Sugarloaf USA Set in the heart of Western Maine, Windledge Farm spans 308 acres of multifaceted landscape with staggering views of the protected High Peaks of Maine. The handsome 60' x 48' stable includes eight spacious stalls, a tack room, heated wash bay, medical room, and office, with a beautifully finished one-bedroom apartment above that enjoys the same breathtaking views as the main home.
18 High Head Road, Edgecomb, ME04556
Represented by Susan Peterson
Offered at $4,250,000
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.
19 Tiger Lily Lane, Cape Elizabeth, ME04107
Represented by Anne Bosworth & Andrea Pellechia
Offered at $3,995,000
Privately situated on 1.65 acres of beautifully landscaped grounds, the home offers thoughtfully designed living spaces featuring six bedrooms, multiple gathering areas, and luxury amenities designed for both comfortable family living and sophisticated entertaining. A charming carriage house further enhances the property, offering guests a private residence complete with a full kitchen, living room, and separate bedroom.
3 Canter Lane, Cape Elizabeth, ME04107
Represented by Alexa Oestreicher
Offered at $3,900,000
A Luxury Residence inspired by Nature: Sited on 16.1 private acres in the heart of Cape Elizabeth, Great Woods Lodge at 3 Canter Lane offers a rare blend of seclusion and convenience. Thoughtfully appointed baths, multiple fireplaces, and a detached carriage house complete the estate. Outside, curated grounds feature exquisite hardscaping, fountains, and lush landscaping, along with deeded access to a peaceful pond.
562 Sound Drive, Mount Desert, ME04660
Represented by Marty Dischinger & Laura Pellerano
Offered at $3,750,000
The property features 1,262 feet of waterfront frontage across 7.44 acres.The main cottage provides convenient one-floor living with two bedrooms, two bathrooms, a fireplace, and cathedral ceilings. Additionally, the lower level includes office space with views of the Sound. The property's footprint comprises the main cottage and a small guest house both surrounded by a shared deck. Being Sold As Is.
16 Bremen Long Island, Bremen, ME04551
Represented by Linda Painter & Tom Field
Offered at $2,800,000
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 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.
27 & 31 Cottage Lane, South Thomaston, ME04854
Represented by Sandra Wendland
Offered at $2,500,000
Tucked into a serene cove just off Sprucehead Island, this exceptional waterfront property offers 207 feet of frontage and easy access to your private sandy beach. The main home, built in 2019, features 4 bedrooms and 3 full baths, including a first-floor bedroom and full bath for flexibility. Exceptional water and island views are visible from nearly every room. Also included is a renovated cottage with 3 bedrooms and 2 full baths, that includes a first-floor bedroom and full bath. Both dwellings are ideal for multi-generational living, guests, or a seasonal retreat.
169 Patrick Mountain Lane, Washington, ME04574
Represented by Kristin Heal
Offered at $2,500,000
Spanning more than 430 acres, this extraordinary off-grid estate offers unmatched privacy, breathtaking scenery, and a lifestyle defined by freedom and self-sufficiency. Privately situated in the woods with its own separate driveway, the charming post-and-beam guest cottage features an inviting first floor with an open living room, eat-in kitchenette, and half bath.
2319 Harpswell Island Road, Harpswell, ME04003
Represented by Will and Ally Fuller
Offered at $2,500,000
Privately tucked away on coveted Bailey Island, this exceptional waterfront retreat captures the essence of refined coastal living. Set on a rare parcel with its own beach and extensive ocean frontage, the property enjoys breathtaking 180-degree water views across a protected cove and out to the Atlantic beyond. Enhancing the property's appeal is the detached Sea Shed, a charming and flexible space well suited for guests, a studio, home office, recreation room, or additional sleeping quarters.
102 Musson Road, Raymond, ME04071
Represented by Heather Shields
Offered at $2,300,000
There is something truly special about this Sebago Lake property, where luxury, comfort, and unforgettable lake memories come together. This stunning waterfront compound delivers unmatched privacy, protected frontage, and exceptional craftsmanship. The main house and guesthouse sit on 1.26 acres, boasting 326 ft+/- of water frontage. The island in front serves as a picturesque landmark, while large glacial rocks protect from wind and wake, naturally deterring boat traffic and enhancing privacy and tranquility.
57 Andersen Road, Raymond, ME04071
Represented by Chessell McGee
Offered at $2,200,000
Welcome to Sebago Lake, where this state-of-the-art retreat awaits its new owners. Formed 14,000 years ago by retreating glaciers, this extraordinary setting of granite boulders and pristine shoreline frames Maine's 2nd largest lake. Completing the property is a garage with a fully equipped 579-square-foot studio apartment above, also with HVAC, along with ample electrical capacity for a true workshop.
48 Sea Street, Rockport, ME04856
Represented by Brian Wickenden
Offered at $1,995,000
In the heart of Rockport village, this beautifully renovated historic home is a just a short stroll to Walker Park, Rockport Marine Park, and the shops and restaurants in the center of town. The main residence features three bedrooms, and three-and-a-half baths. A separate and charming one-bedroom, one-bath apartment provides flexible living options for extended family, guests, or for good rental income.
47 Skillin Road, Cumberland, ME04021
Represented by Heather Shields
Offered at $1,995,000
Overlooking the Piscataqua River, this extraordinary post and beam home offers a rare opportunity to own a piece of Maine history. Originally built as a mill circa 1860+/-, the property has been thoughtfully renovated while preserving its historic character and craftsmanship. The lower-level ADU provides exceptional flexibility with a private entrance, full kitchen, living and dining areas, two bedrooms, laundry, and river views.
160 Main Street Rear, Kennebunkport, ME04046
Represented by Marika Clark
Offered at $1,895,000
Capturing coastal elegance in the heart of Cape Porpoise, this elevated modern home blends luxury, comfort, and convenience. The main residence spans 2,665 square feet and was designed for low-maintenance living with quality craftsmanship throughout. Adding versatility, a detached 800-square-foot year-round cottage provides the perfect retreat for guests or extended stays, complete with a full kitchen, bedroom, bathroom, loft, washer/dryer, and dishwasher.
4 Elm Street, Kennebunkport, ME04046
Represented by Bill Gaynor
Offered at $1,850,000
This genuinely refined residence captures the past while boasting the amenities of today. The Oliver Davis house and its nearly two century history is proudly emblematic of the early days of seafaring in Kennebunkport. Two Bedrooms ensuite in the main house are paired with two others in the Guesthouse. Exquisite landscaping and plantings make this a true oasis within all of the bustling activities of The Port.
161 North Road, Matinicus, ME04851
Represented by Kristin Heal
Offered at $1,775,000
Escape to the beauty and quiet of Matinicus Island. Situated more than 20 miles off the coast of Midcoast Maine, this private 20-acre oceanfront compound includes a year-round main house and a seasonal guest cottage, all set along 1,000 feet of bold shoreline. An outdoor shower and rolling lawn lead to the dramatic shoreline and a firepit with sweeping northwestern ocean views, ideal for taking in unforgettable sunsets.
26 Martin Road, Alna, ME04535
Represented by David Hagan
Offered at $1,675,000
Private Net-Zero Country Estate on the Sheepscot River. A rare opportunity to own an extraordinary private family compound set on 18 pristine acres with 950 feet of frontage along the historic Sheepscot River and the charming village of Sheepscot Village. Family and guests will enjoy a separate 1,000-square-foot farmhouse cottage featuring three bedrooms and comfortable private accommodations. Ideal for extended family, visitors, a caretaker, or potential rental income, the cottage adds both versatility and value.
9 Conifer Ridge Road, Cumberland, ME04110
Represented by Kristina Keaney & Carrie Martin
Offered at $1,275,000
Extraordinary post-and-beam barn home featuring a 3-bedroom, 2-bath main residence plus a 1-bedroom accessory dwelling unit above the attached two-car garage. The barn was originally constructed in 1812 as part of the Morrill Homestead. The conversion to modern living space began in the 1970s with renovations over the years, including the addition of the two-car garage and apartment in the early 2000s.
227 Quail Run Road, Bristol, ME 04539
Represented by Fred Hebert
Offered at $975,000
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. ''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.
2 Twin Oaks Lane, Sedgwick, ME04676
Represented by Marty Dischinger & Parker Allen
Offered at $695,000
From the moment you enter the main house, you see views of the Benjamin River and Eggemoggin Reach. These 2 beautifully landscaped homes provide rental opportunities and histories in both AIRBNB for the Cottage and local rental markets for the Main House.
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