Designed for luxurious living, these versatile estates and grand retreats offer ample space for everyone to gather, relax, and enjoy the beauty of Maine. Whether it’s a sprawling estate with multiple homes, a beautiful main property with a guest cottage, or a combined residence with exclusive entrances and amenities, these properties provide the perfect setting for creating lasting memories with friends and family. Explore some of our luxurious retreats and compounds for sale below!
857-861 Kings Highway, Kennebunkport, ME 04046
Offered at $8,850,000
Represented by Heather Shields
Nestled on Goose Rocks Beach in Kennebunkport, this luxurious family compound is perfect for multi-generational living. The property includes a main residence with 3 bedrooms and 4 bathrooms, and an award-winning beach pavilion with 2 bedrooms and 3 bathrooms. Designed by Carol A Wilson and built by Bowley Builders, both homes feature bespoke finishes and panoramic ocean views. Ideal for family gatherings, the compound offers ample space and privacy, with world-class appliances and a Crestron intelligent home management system ensuring convenience and comfort.
402 Baker Hill Road, Freeman Twp, ME 04983
Offered at $5,200,000
Represented by Glenn Jonsson and Marika Clark
Windledge Farm in Western Maine is a breathtaking 308-acre estate with panoramic views of the High Peaks. The 4,500 sqft contemporary main house, designed by Frank Robinson, blends state-of-the-art amenities with serene, artistic design. The property also features a premier equestrian facility, including a 60’x48′ stable with eight stalls, a tack room, heated wash bay, medical room, and a one-bedroom living quarter. With 10 paddocks, 4 large pastures, 7 acres of hay fields, and extensive trails, the estate is a haven for equestrian enthusiasts.
394 Hathorne Point Road, Cushing, ME 04563
Offered at $3,750,000
Represented by Leslie Tranchell and Valerie Foster
Privately situated, spacious and light-filled 3 bedroom, 3.5 bath Main House with attached 2 car garage with full staircase to unfinished space above plus a 2 bedroom, 2 bath guest house and deep water dock make this the perfect Maine family compound. Walls of windows take advantage of the water views and peaceful woodland setting. Spacious decks stretch the length of the houses and are perfect for relaxing or entertaining. Wood burning fireplaces in both houses to enjoy on the foggy days. Beautifully landscaped and fully furnished. This property is also a very successful, income-producing Summer rental.
282 King Phillips Trail, Boothbay, ME 04544
Offered at $3,600,000
Represented by David Hagan
Reeds Island is a spectacular historic island combining a 1960 converted 4655 +/- square foot restaurant and 2006 1,330 square foot cottage into a wonderful family compound retreat. This property on an 8-acre peninsula offers a cottage and a main house with stunning ocean views. The cottage has 2-3 bedrooms, 2 baths, and an open living area with a deck. The main house features 4 bedrooms, 2 full and 2 half baths, a loft, and a large open space with a fireplace and game room. Accessible by a private causeway, the homes provide privacy and breathtaking views of the Damariscotta River, Christmas Cove, and more. The island, once visited by President John F. Kennedy, is perfect for family gatherings and peaceful retreats, with a rustic cabin feel and proximity to Boothbay Harbor amenities.
3 Flye Point Road, Brooklin, ME 04616
Offered at $3,500,000
Represented by Laura Farr
This exceptional waterfront family compound in Brooklin features a 4,500 sq. ft. fully furnished main house and a 3,000 sq. ft. renovated former boat-building barn. Set on 2.4 acres with 1,200 feet of frontage on Herrick Bay, both buildings offer breathtaking views. The main house, renovated in 2020/21, includes 4 bedrooms, 2.5 baths, and a luxurious penthouse suite with a private deck. The barn includes a 2-bedroom, 2.5-bath apartment and expansive space for gatherings or hobbies. Both buildings are designed with vaulted ceilings, large windows, and elegant, neutral interiors.
78 & 98 Hussey Hill Road, Oakland, ME 04963
Offered at $3,500,000
Represented by Lois Lengyel and Michael Lynch
A unique opportunity awaits in Central Maine with this versatile 30-acre property, ideal for both residential and commercial uses. Just 10 minutes from Interstate 95, it includes a ~7000SF residence with a flexible layout, a barn venue for 400 people, an outdoor arena, multiple barns, a 5-car garage, a lighted parking lot for 200 cars, a pond, and open fields. The main house offers multi-generational living options with 3 levels and 2 full kitchens. The modern, stylish barn, converted in 2016, is perfect for weddings and events.
2620 Sennebec Road, Appleton, ME 04862
Offered at $2,950,000
Represented by Brian Wickenden
This renovated farmhouse on a 42.5-acre waterfront lot features 7 bedrooms, a heated barn for entertaining, and a second barn that can be converted into a guest cottage. Owned by the same family for over 90 years, it was moved and fully renovated in 2003. The property includes hay fields, orchards, and a heated garage. Inside, enjoy a custom kitchen, three fireplaces, and radiant heating. With stunning sunset views over Appleton Ridge, it’s perfect for multi-generational living.
2 Town Landing Road, Falmouth, ME 04105
Offered at $2,250,000
Represented by Lois Lengyel
This contemporary coastal home in Falmouth offers ocean views and is just a block from Town Landing beach. It consists of two combined homes with separate entrances, totaling 7 bedrooms, 2 living rooms, and 2 kitchens, ideal for multigenerational living or rental potential. Designed with a nautical theme, it features high ceilings, exposed beams, and abundant natural light. Highlights include a 4th-floor reading nook, rooftop terrace, two large porches, and a patio with a fire-pit. Located 10 minutes from Portland, it’s close to gourmet restaurants, shops, and the Town Landing Market.
18 Salamander Road, Lincolnville, ME 04849
Offered at $2,175,000
Represented by Maria Weymouth and Brian Wickenden
This Lincolnville, Maine property features a restored historic cape and a separate carriage house on 81 acres of fields and woods. The main house has four bedrooms and charming architectural details, while the carriage house offers two bedrooms and a detached garage. The estate includes fields, forests, quarries, ponds, and extensive stonework. With 43.21 acres dedicated to conservation, this property blends impeccable design with natural beauty, perfect for those seeking comfort and privacy.
4 & 5 Anchorage Lane, Owls Head, ME 04854
Offered at $1,850,000
Represented by Michael Lynch
Anchorage Lane is perfect for a family compound, featuring a year-round home with a guest apartment and a seasonal seaside cottage. The main home offers an eat-in kitchen, living room with water views, two bedrooms, and a private primary suite upstairs. The lower level includes a one-bedroom apartment. Enjoy stunning island and bay views, an expansive deck, and a well-tended garden. The property also has a heated two-car garage and a detached one-car garage. Close to Crockets Beach and Birch Point State Park, this versatile property spans approximately 1.4 acres.
99 Main Street, Kennebunk, ME 04043
Offered at $1,775,000
Represented by Andi Robinson and Elaine Prendergast
This historic Federal Style colonial residence, built in 1799 by Nathaniel Frost, is located on Main Street. Hidden up a winding drive, it features meticulously maintained grounds with sweeping lawns, apple orchards, and organic gardens. The property includes a 3-bay barn, a main house with 20 rooms, 7 bedrooms, 5.5 baths, and 8 woodburning fireplaces. Modern amenities blend with historic charm, including a central kitchen with custom appliances and an octagonal sunroom. The home also offers two private apartments, each with 2 bedrooms and 1 bath, ideal for guests or rental income.
119 Derby Road, Islesboro, ME 04848
Offered at $1,150,000
Represented by Michael Lynch
This charming Islesboro property combines historic elegance with modern practicality, perfect for a family compound. Built circa 1895, it features 5 bedrooms, 4.5 baths, living and dining rooms with fireplaces, an eat-in kitchen with pantry, and a laundry room. Modern amenities include air conditioning, a generator, and high-speed internet. The property also boasts a freestanding barn and garage, transformed into a luxury guest space with a mini-kitchen and two-car garage. Surrounded by trees, a white picket fence, and perennial gardens, this home is ideal for family gatherings and year-round living.
