luxury seaside house for rent Kennebunkport, United States

Welcome to 25 Algonquin Road, a newly constructed masterpiece in Cape Elizabeth. Thoughtfully designed and meticulously crafted, this modern coastal retreat offers an exquisite blend of contemporary luxury and classic New England charm. Available for monthly stays, this home promises an exceptional escape for discerning guests seeking comfort, style, and serenity in an unmatched coastal setting. Property Highlights: New Construction : Every detail of this home reflects modern design and craftsmanship, from pristine finishes to state-of-the-art systems. Be the first to experience this immaculate property. Elegant Bedrooms : Spacious and beautifully appointed bedrooms with premium bedding offer a restful haven for up to 12 guests. Oceanfront-facing bedrooms feature balconies, allowing you to enjoy the soothing ocean breeze and stunning views right from your room. Open-Concept Living : The airy, open floor plan features soaring ceilings, hardwood floors, and oversized windows that flood the home with natural light and coastal views. Gourmet Kitchen : A chef’s dream, the kitchen boasts top-of-the-line appliances, sleek quartz countertops, and a generous island, making it perfect for entertaining or intimate family meals. Outdoor Oasis : Step outside to a private deck and professionally landscaped yard designed for relaxation and gatherings. Enjoy the sparkling heated pool, a BBQ for alfresco dining, and a cozy firepit perfect for evening conversations under the stars. For added convenience, a cabana room offers a shaded retreat to dry off, enjoy lunch, or take a break from the sun. An outdoor shower provides the perfect way to rinse off after a day by the pool or beach. Surfside Walking Path : Direct access to a picturesque coastal path invites you to explore the beauty of Maine’s shoreline right from the property. Modern Amenities : High-speed Wi-Fi, smart home technology, and energy-efficient systems enhance the comfort and convenience of your stay. Located on a quiet private road in Cape Elizabeth, this home is minutes from Crescent Beach State Park, Fort Williams Park, Kettle Cove State Park, and iconic lighthouses. Take a peaceful stroll to the stunning Trundy Beach, just a quick 10-minute walk from the property. Its proximity to award-winning dining, boutique shopping, and Portland’s vibrant cultural scene offers a perfect balance of seclusion and accessibility. With brand-new construction, luxurious finishes, and thoughtful amenities, 25 Algonquin Road delivers the ultimate coastal living experience. Whether relaxing poolside, strolling the surfside walking path, or enjoying the area's attractions, this retreat promises unforgettable memories. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby’s International Realty is pleased to this luxury coastal retreat at 4 Keyes Lane in Cape Elizabeth, Maine. Welcome to your dream coastal getaway. Nestled in the heart of one of Maine’s most coveted seaside communities, 4 Keyes Lane offers the perfect blend of privacy, luxury, and proximity to iconic destinations. Located right next to Fort Williams Park and the world-renowned Portland Head Light, this home puts you within easy walking distance to some of Maine’s most breathtaking coastal scenery. Stroll through the park’s oceanfront trails, explore historic ruins, or simply relax and take in the crashing waves and iconic lighthouse views. This thoughtfully and unique designed home features three well-sized bedrooms, offering comfortable accommodations for families, couples, or small groups looking to unwind by the sea. Relax and recharge in your private sanctuary, where modern coastal elegance meets classic Maine charm. Whether you’re sipping coffee on the porch, preparing a quiet meal with fresh local ingredients, or cozying up in the airy living room after a beach day, every detail has been curated for comfort and style. Steps from the sand, you’ll be within easy reach of Casino Beach, a local favorite for sunbathing, paddleboarding, or simply watching the waves roll in. For dining, shopping, and arts, Portland’s Old Port district is less than 15 minutes away, offering award-winning restaurants, boutique shopping, and a vibrant waterfront scene. This property is available on a 30-day minimum basis, making it ideal for extended vacations, remote work stays, or seasonal living in one of Maine’s most scenic coastal settings. Perched in a prime location, the home offers gorgeous, gleaming views of the Atlantic, providing a stunning backdrop from sunrise to sunset. Available on a 30-day minimum basis, this exceptional retreat is perfect for extended vacations, remote work getaways, or seasonal living in one of Maine’s most scenic coastal settings. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby’s International Realty is pleased to present 65 Eben Hill Road – A Summer Coastal Escape on Cousins Island in Yarmouth, Maine Spend your summer soaking up the sunshine, sea breeze, and coastal charm of Southern Maine at this beautifully updated Cape-style home, located just over the bridge on scenic Cousins Island. 65 Eben Hill Road offers the perfect setting for a relaxing and memorable summer getaway—complete with ocean access directly across the street and a bright, open layout designed for unwinding and reconnecting. Inside, the home welcomes you with vaulted ceilings and sun-filled spaces that include a connected living room, dining area, and a cozy sunroom featuring a daybed, perfect for afternoon reading, morning coffee, or a quiet nap after a day in the sun. Large southern-facing windows let in soft natural light all day, creating a warm and airy atmosphere that embraces the ease of summer living. With three spacious bedrooms—one on the first floor and two on the second floor—this home offers a flexible layout ideal for families, couples, or multi-generational guests. Each bedroom is thoughtfully appointed for comfort and privacy, making it easy to settle in and feel at home. Step outside and enjoy the best of summer living in the large fenced-in backyard, perfect for lawn games, grilling, or lounging after a beach day. Just a short walk or drive from the home, you can launch your kayak or paddleboard and explore the peaceful coves around Cousins and Littlejohn Islands. Access to Casco Bay is directly across the street and considered a “right of way” for putting in watercraft. Please note that the area is a bit rocky, and the tides—ranging up to 8 feet on the island—can impact accessibility. For more traditional beach days, Sandy Point Beach is just one mile away, located directly under the bridge. You'll also find several other beautiful beaches within a 30-minute drive from the property. Head into downtown Yarmouth to enjoy waterfront dining at Royal River Grill House, or treat yourself to a night out at local gems like The Garrison or Otto’s. For a truly special summer outing, hop on the Chebeague Island Ferry just 2 miles from the house. Spend the day biking around the island, exploring quiet beaches, or grabbing lunch with a view of Casco Bay. Nearby, you’ll also find Freeport’s famed outlet shops and L.L. Bean (15 minutes away), and the vibrant city of Portland just under 30 minutes away, offering everything from food trucks to fine dining, craft breweries, and harbor cruises. Whether you're planning a week of family fun or a peaceful escape by the sea, 65 Eben Hill Road is your ideal summer home base for exploring the magic of coastal Maine. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby’s International Realty is proud to present a Private Coastal Estate on Cousins Island in Yarmouth, Maine. Perched on the stunning coastline of Southern Maine, this private oceanfront estate offers a rare opportunity to experience the perfect blend of seclusion and luxury. Located at the end of a quiet drive on sought-after Cousins Island, this exceptional property is a true coastal retreat—offering expansive living space, high-end amenities, and breathtaking panoramic views of the Atlantic Ocean. The home features six well-appointed bedrooms, including a serene primary suite with sweeping ocean vistas. Five of the bedrooms offer water views, and two provide direct deck access, including the primary suite. The main living area also opens seamlessly to a spacious patio and covered porch, perfect for enjoying the sea breeze and unforgettable coastal sunsets. Thoughtfully designed for both comfort and entertaining, the estate offers ample room for guests, along with a large, sunlit home office and multiple workspaces—ideal for remote professionals or extended stays. Outside, embrace the best of coastal Maine living with access to a private beach, a deep water dock, and a mooring—a rare amenity for boating and water enthusiasts. After a day on the water or in the sun, gather around the oceanfront fire pit or unwind on the deck, surrounded by the sounds of the surf and the sparkle of the stars. Additional features include a two-car garage, EV charger, and beautifully maintained outdoor spaces designed for both relaxation and recreation. Whether you’re seeking a peaceful seasonal sanctuary or a luxurious work-from-home haven, this exclusive estate on Maine’s coast delivers privacy, elegance, and the unmatched beauty of oceanfront living. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby’s International Realty for more information on this exclusive offer.

Experience the perfect blend of comfort, elegance, and coastal beauty at this charming waterfront retreat on Mere Point in Brunswick, Maine. Nestled along the shores of Middle Bay, this stunning property offers a quintessential Maine experience—where refined interiors meet rugged natural scenery and the rhythm of the tides sets the pace for your stay. Surrounded by sweeping ocean views and mature pines, this coastal haven provides the ultimate private escape. Spend your days exploring the shoreline, launching a kayak from your private waterfront, or simply relaxing with a glass of wine as the sun sets over the bay. Just minutes from downtown Brunswick and the vibrant village of Harpswell, this home offers both seclusion and convenience in one of Midcoast Maine’s most desirable locations. The main house welcomes you with light-filled living spaces that capture the tranquil essence of coastal living. Large windows frame stunning views of the water, while warm wood accents and thoughtfully curated furnishings create an inviting atmosphere. The gourmet kitchen is a highlight, featuring high-end appliances and ample counter space for preparing fresh seafood dinners or morning coffee with a view. In addition to the main residence, the property includes separate guest quarters offering a private and comfortable living space. This thoughtfully designed area features its own full kitchen, bathroom, and bedroom, making it ideal for guests, extended family, or use as an independent suite. Whether used for hosting visitors or as a serene retreat, the guest house adds both versatility and value to this coastal property. Mini-split air conditioning units have been added to the upstairs bedroom, living room, and guest house, providing cooling to the home’s main areas and enhancing summer comfort. The outdoor spaces are equally captivating. Enjoy morning coffee on the deck as the lobster boats head out to sea, dine al fresco while watching the tide roll in, or gather around the fire pit for coastal evenings under the stars. With plenty of open lawn and shoreline access, the property invites you to enjoy Maine’s coastal lifestyle to its fullest. Please note: This home is located on an authentic, working waterfront, offering a true taste of coastal Maine life. During low tide, local clammers can often be heard heading out by boat—sometimes early in the morning or late at night. While their activity is part of the genuine charm of Mere Point and its heritage, guests should be aware of this lively rhythm of the coast before booking. Just minutes from Brunswick’s boutique shopping, renowned restaurants, and cultural attractions, 735 Mere Point Road combines the serenity of a seaside escape with the convenience of nearby amenities. Whether you’re seeking quiet relaxation, outdoor adventure, or a front-row seat to the daily life of Maine’s waterfront, this home provides an exceptional experience in an unforgettable setting. This property is available for select summer and offseason rentals. Please inquire for more information and availability. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby’s International Realty for more information on this exclusive offer.

Legacy Properties Sotheby’s International Realty is proud to present this serene, private waterfront estate at 27 Old Wharf Road, Boothbay, Maine—a luxurious coastal retreat that beautifully blends comfort, elegance, and the quintessential Maine experience. Set on eight acres of rolling lawns, wooded walking trails, and peaceful shoreline, this casual yet refined farm-style home offers exceptional privacy at the end of a long gravel drive. With expansive water views from nearly every room, this is an ideal setting for families, multi-generational gatherings, or anyone seeking a tranquil place to unwind and enjoy the best of the Boothbay region. The Home Designed for both relaxation and convenience, the property offers generous living space and accommodates up to 10 guests. Four beautifully appointed bedrooms, including: Two with queens, 1 cal-king & bath ensuite, & 1 with 2 twin beds & bath ensuite. Multiple living and entertainment spaces, including a cozy sitting room, entertainment room, and a dramatic open-concept great room with soaring ceilings, a piano, and walls of windows framing sweeping water views. . The great room dining table has wonderful water views to see lobster boats, seals, and birds. Enjoy the convenience of a washer/dryer. Outdoor Living Step outside to immerse yourself in the peace and natural beauty of Barters Island: An expansive waterside deck perfect for alfresco dining, morning coffee, and evening cocktails by the water. A deep-water dock and mooring (accommodating vessels up to 50 ft)—a rare and prized amenity for boaters exploring Maine’s iconic coastline. Easy on-site launching for kayaks, paddleboards, and small motorboats. Rolling lawns suitable for badminton, lawn games, or evenings by the fire pit overlooking the water. A stunning hundred-year-old cedar grove leading to the dock, adding a magical sense of place. Access to private walking paths on the property, leading to a point with panoramic views of the sparkling Sheepscot River—often visited by seals, seabirds, and passing lobster boats. Additional Glamping Quarters: A rustic bunkhouse (king bed + three single cots) and a charming over-the-water boathouse (sitting area + twin loft beds) provide unique retreat spaces for adventurous guests. These structures do not have plumbing; the main house’s ground-level bathroom is conveniently nearby. The Surroundings 27 Old Wharf Road places guests close to Boothbay’s most cherished attractions: The renowned Coastal Maine Botanical Gardens Boothbay Harbor’s charming shops, cafés, and dining Electric bikes and kayaks are available to rent in town, expanding your opportunities for exploration. Boothbay Harbor Yacht Club and Boothbay Harbor Country Club Camp Knickerbocker (excellent for families) Scenic open-space walking trails including Porter Point Preserve, Oak Point Farm, nearby BRLT trails, and the iconic Ocean Point coastal walk Easy day trips to Damariscotta, Wiscasset, or Rockland’s Farnsworth Museum featuring Wyeth family works Local schooner sails and island boat tours A Perfect Maine Coastal Escape Whether you’re launching kayaks from the dock, savoring peaceful mornings watching wildlife from the great room, or sailing directly from your private mooring, this property offers an unforgettable blend of luxury, privacy, and natural beauty. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby’s International Realty for more information on this exclusive offer.

Stunning Oceanfront Condo with Sweeping Water Views! Enjoy coastal living at its finest in this spacious and inviting residence, where breathtaking ocean views take center stage. The expansive open-concept living and dining area features a dramatic cathedral ceiling, beautiful chandelier, fireplace and walls of windows overlooking the sea. Relax in the sitting area, entertain in the dining room or enjoy a game of pool—all while taking in the spectacular waterfront setting. The well-appointed kitchen features marble countertops, counter seating and a newer Bosch dishwasher. Two generously sized bedrooms each offer a private full marble bath, while the primary suite is enhanced by its own fireplace and beautiful ocean views. Step outside onto one of two decks to enjoy the sea breeze, watch the changing tides, or unwind beneath the moonlight. Additional conveniences include an in-unit laundry room, newer storage room, elevator access to the residence and private parking located just across the way. A welcoming, flower-filled entrance completes this special coastal setting. A wonderful opportunity to enjoy the beauty and tranquility of oceanfront living every day.

Legacy Properties Sotheby’s International Realty is proud to present an Oceanfront Luxury Retreat in Rockport, Maine. Experience the ultimate in coastal luxury at 18 Eastward, a stunning 4-bedroom, 4.5-bath residence nestled in one of Rockport’s most prestigious oceanfront communities. Overlooking the breathtaking Penobscot Bay, this exceptional contemporary home offers unparalleled elegance, privacy, and a perfect balance of relaxation and recreation in the heart of Maine's Midcoast region. Set within 60 acres of pristine, manicured grounds, the home features expansive windows that frame spectacular water views and the surrounding natural beauty. Thoughtfully designed for both comfort and style, 18 Eastward offers a seamless indoor-outdoor flow, with sun-drenched living spaces, custom finishes, and inviting furnishings—ideal for hosting guests or enjoying quiet moments by the water. The spacious layout comfortably accommodates up to 8 guests with luxurious bedrooms. The home’s exceptional amenities include a heated seaside pool, tennis courts, and scenic walking trails. Perfectly positioned for watercraft enthusiasts, 18 Eastward offers easy access to Penobscot Bay, where you can launch your own boat or explore by kayak. The property’s location is ideal for those who love to spend time on the water, with proximity to Rockport, Camden, Lincolnville, and convenient access to ferries to the islands. Golf lovers will appreciate being just minutes away from oceanfront golfing at the Samoset Resort, and those looking for the vibrant charm of coastal Maine will find themselves close to fine dining, shopping, and cultural experiences in the charming towns of Rockland, Camden, and Lincolnville. Whether you're drawn to outdoor adventures or simply seeking a serene retreat, 18 Eastward offers the ultimate luxury experience for those who want to immerse themselves in the natural beauty and dynamic lifestyle of Maine’s Midcoast. This property is available on a monthly basis, 30-day minimum. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby’s International Realty for more information on this exclusive offer.

Situated prominently overlooking the harbor in the heart of enchanting Rockport Village is the luxurious and refined architectural masterpiece, 19 Sea Street. The home’s sprawling accommodations, exceptional amenities, and beautiful grounds are replete with your own private sandy beach, deep-water dock, expansive decks, and stunning terraces that weave seamlessly into the landscape, creating a place where leisure and entertainment harmoniously converge, for a vacation experience you’ll never forget. This spectacular home, a rare gem among the coastal treasures of Maine, offers unparalleled views that stretch far and wide, providing a truly memorable vacation for those seeking the pinnacle of elegance and comfort. View our Matterport 3D virtual tour for an immerse experience of this property and to explore the floor plan and layout in great detail. The sprawling accommodations are comprised of the spacious primary living quarters which include four bedrooms with ensuite bathrooms and two attached one bedroom, one bath, apartment-style living quarters with their own entrances and kitchens. The primary living quarters boast a custom designed kitchen has high ceilings adorned with antique ceiling beams, stone floors, and a gas fireplace. A chef's dream come true, this culinary haven features a generously sized island, walk-in pantry, two refrigerators, two dishwashers, and warming lamps. There are French doors leading to an expansive terrace, perfect for alfresco dining under the starlit Maine sky. An exquisite dining room graced with floor-to-ceiling windows frame the ever-changing views of Rockport Harbor. There is a sitting room with a gas fireplace and French doors leading to the spacious terrace, a large living room gas fireplace, and sitting alcove with views into Rockport Village. There is also a yoga/meditation space and exercise room. A speaker system provides music and ambiance throughout the majority of primary home. The two apartment style living quarters are immediately connected to the primary home, yet separate. 19 Sea Street is a sanctuary of luxury and style, a home where modern living meets the timeless allure of coastal Maine. Indeed, this magnificent property stands as a singular testament to the art of living well in MidCoast Maine. The home is located in a quiet neighborhood with a nearby park and the center of historic Rockport Village and harbor and its summer concerts and activities, restaurants, and new library, are just a stroll away. Camden and Rockland are mere minutes by car from the home. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby’s International Realty is pleased to present 3 Dillingham Point in Camden, Maine — a premier luxury retreat where refined coastal living meets relaxed Maine charm. Located just one block from the peaceful shores of Laite Beach, this recently renovated four-bedroom, five-bathroom home offers a perfect blend of modern elegance and thoughtful comfort. With water glimpses, fresh sea breezes, and high-end amenities throughout, 3 Dillingham Point is an ideal getaway for families or groups seeking an exceptional Mid-Coast Maine experience. The home has been fully remodeled with a bright, open layout, premium finishes, and timeless coastal décor. Designed for comfort and privacy, it features four spacious en-suite bedrooms. On the first floor, the primary suite offers a king bed and a private bath. Upstairs, the second bedroom includes a queen bed and en-suite bathroom. The third bedroom is a charming loft-style bunk room with a full bed—ideal for kids or extra guests. The fourth bedroom, a second large upstairs suite, features a king bed along with two twin mattresses, making it perfect for families or groups needing flexible sleeping arrangements. Additional highlights include a cozy children’s nook and a dedicated exercise room to help you stay active during your stay. Step outside to enjoy the private backyard oasis featuring a soaking pool, hot tub, and firepit—ideal for both relaxation and recreation. Guests will also appreciate the ample lawn space for games, lounging, or simply taking in the peaceful surroundings. Beyond the property, you’re just minutes from everything Camden has to offer. Hike or drive up Mount Battie for panoramic views of Penobscot Bay, stroll through the charming downtown village filled with boutique shops, art galleries, and award-winning restaurants, or explore scenic biking and walking trails that wind through the coastal landscape. Whether you're sipping morning coffee on the porch, strolling to the beach, or enjoying an evening under the stars, 3 Dillingham Point offers an unparalleled coastal escape in one of Maine’s most treasured seaside towns. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby's International Realty is proud to present 81 Point Road in Brooksville, Maine. A completely renovated luxury estate offering unparalleled coastal living set on 7 acres of breathtaking waterfront property. This remarkable residence features two wings seamlessly connected by a breathtaking glass-enclosed bridge, creating a sense of openness and light. The high-end chef’s kitchen is a culinary dream, fully appointed and complemented by a spacious recreation room and an elevator for effortless access throughout the home. Each bedroom is designed with spaciousness and comfort in mind, while the master suite serves as a private sanctuary, complete with a luxurious en-suite bathroom that offers a spa-like atmosphere with modern fixtures and elegant finishes. Step outside to discover your own slice of paradise. The expansive deck overlooks the tranquil waters, ideal for alfresco dining or simply unwinding while enjoying the gentle ocean breeze. With panoramic views of the water and lush surroundings, this property is a serene retreat for those seeking tranquility and sophistication. Explore scenic walking trails that are easily accessible from the back deck, where you can fully appreciate the breathtaking views. As part of a private beach association, you will have exclusive access to a secluded shoreline. Set on Cape Rosier, a historic and picturesque peninsula celebrated for its natural beauty and maritime legacy, this remarkable property enjoys a privileged position in a locale that has long inspired artists and nature enthusiasts alike. Cape Rosier is part of the Blue Hill Peninsula, known for its lush landscapes, quiet charm, and historic significance dating back to early American settlement. Brooksville is a hidden gem on the Maine coastline, celebrated for its peaceful, unspoiled landscapes and rich maritime heritage. This estate is ideally positioned for exploring nearby charming villages and natural attractions. Just a short drive away, Blue Hill boasts art galleries, boutique shops, and fine dining options. For outdoor enthusiasts, Holbrook Island Sanctuary is a mere 15-minute drive, while Acadia National Park is just over an hour away, making it an ideal destination for a day trip. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby’s International Realty is pleased to present 35 Old Fields Way in Castine, Maine. Set on 22.4 private acres with an extraordinary 1,300 feet of owned shoreline along the tranquil Bagaduce River, this rare offering delivers a compelling blend of privacy, scale, and authentic Maine coastal living. The calm, protected waters and sweeping, ever-changing views create a timeless setting for both refined relaxation and memorable gatherings. Ideally located, the property is just over an hour from Bar Harbor, Acadia National Park, and Camden, offering access to some of Maine’s most celebrated destinations while maintaining a quiet, residential feel. The main residence is thoughtfully designed to capture water views from nearly every room. Grand yet welcoming, the home features six bedrooms, six full bathrooms, and one half bath, including a spacious primary suite. Additional highlights include formal living and dining rooms ideal for entertaining, a chef’s kitchen, a private office with custom built-ins, and a comfortable family room centered around a wood stove. Architectural detail and fine craftsmanship are evident throughout, striking a balance between elegance and livability. Recreational amenities include a pool table, large movie screen, and flexible spaces. Outdoors, the estate unfolds into rolling lawns, gardens, and meandering shoreline paths—perfect for lobster bakes, lawn games, summer barbecues, and intimate celebrations. Evenings are best enjoyed on the porch beside the stone fireplace, cocktail in hand, as boats drift along the river and the sun sets over the water. Water access is a defining feature of this property. The shoreline offers steps leading down to the water with a small beach area. Kayaking, paddleboarding, and swimming can be enjoyed directly from the shore, and boat rentals and guided kayaking excursions are readily available in Castine. For boating and sailing enthusiasts, this estate is unmatched, a protected deep-water frontage (approximately 100 ft depth) and a private mooring. Despite its privacy, the estate is only moments from the historic village of Castine, known for its charming shops, waterfront dining, cultural landmarks, and its iconic Fourth of July parade—offering small-town coastal charm without the crowds. A discount is offered for payment made via check or wire transfer instead of via credit card. Please contact Legacy Properties Sotheby's International Realty directly for more details.

236B Smoke Valley is serene and surrounded by nature, offering peaceful mornings, beautiful sunsets, and water access right outside your door. A deep-water pier and float can accommodate a boat up to 35 feet with a 3.5-foot draft. Enjoy use of the heated pool (seasonal), tennis court, and a detached second-floor pool house office with sweeping views of the salt marsh and tall pines. Outdoor living areas include a hilltop stone terrace with firepit, outdoor shower, hammock, and propane grill. Two kayaks, two paddleboards, and a canoe are available for use. Inside, guests will find central air conditioning, Wi-Fi, television, and laundry. Sleeps up to five adults. Three bedrooms: two king beds and one queen. Monthly rates: $28,000 July and August; $10,000 May, June, September, and October; $4,000 November through April. Rental Terms: Other / Short Term - May June September October: $10,000 Summer Monthly: $28,000 Per Month

Escape to a relaxing, fun-filled vacation at this charming rental home located at 97 Sixth Ave, West Hyannisport. This well-appointed retreat is equipped with everything needed for a comfortable and memorable stay. Enjoy central air conditioning, provided linens and towels, high-speed internet, and cable TV. Refresh yourself in the outdoor shower after a day at the beach, and unwind on the spacious deck, perfect for outdoor dining and lounging. Beach chairs and beach towels are provided for your convenience. A Barnstable beach pass is included, offering easy access to beautiful local beaches. The home sleeps up to six guests with two cozy queen beds and two comfortable full beds. Please note that the rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $3,400 Per Week

A Cape Cod Quintessential summer retreat with spectacular views of the Ocean and saltmarsh. A wonderful home to create those Cape Cod Memories. This home is located in the Sippewissett area in desirable West Falmouth. The private association beach is steps away where you can swim, sun, kayak and paddle board. With west facing views you will be mesmerized by the amazing sunsets of West Falmouth. This home has a terrific floor plan for large families with numerous gathering areas, and private sitting areas There are views from nearly every room of the home. With close proximity to downtown Falmouth and Woods Hole, you will be able to enjoy the shopping, restaurants, and access the ferry boat to Martha’s Vineyard. No Availability left for 2021. Rental Terms: Summer Weekly: $3,900 Per Week

Vacation in this Spectacular Oceanfront Estate in Falmouth with a private beach on Vineyard Sound. Walls of over-sized windows and sliders provide beautiful ocean views from nearly every room in the home. This custom built contemporary is impeccable, has over 6,000 sqft of living space, and offers 3 floors of living with 2 extraordinary Master Bedroom ensuites with private sitting areas. The home is equipped with an elevator to access second and third floor bedrooms. There are numerous gathering areas for relaxing and entertaining inside the home, and there are tiers of private exterior balconies and decks that wrap around the home to relax in the sun or shade and take in the beautiful vistas. Swim, paddle board, and kayak off of the sandy white beach at your back door. Both Master bedrooms have king size beds, bedrooms 3 and 4 have Queen sized beds, and the 5th bedroom has 2 twin beds. There is a terrific BBQ grill and large yard for cookouts. This home is located in close proximity to downtown Falmouth for shopping, restaurants, and ferry to Martha's Vineyard. Rental Terms: Other / Short Term - Two weeks: $40,000

Exclusive oceanfront on Penzance Point - A Classic Cape Cod Summer Awaits. Nestled in the private enclave of Penzance Point, this nostalgic Cape offers a rare blend of seclusion, charm, and sweeping water views. This spacious oceanfront haven hosts 5 bedrooms and 3.5 baths, with stunning vistas from every room and an expansive deck that wraps the home, drawing you into the natural beauty of Buzzards Bay and Woods Hole Harbor. Watch the steady rhythm of boat traffic by day and toast unforgettable sunsets by night. The sun-drenched living room opens effortlessly onto the deck, creating the perfect flow for summer entertaining and relaxed coastal living. A well-equipped kitchen and pantry make dining easy, whether you're whipping up a simple lunch or a seafood feast. Let the sound of rolling waves lull you to sleep, and wake to sea breezes and salt air. Just minutes away, discover the charm of Woods Hole Village and downtown Falmouth with its laid-back eateries, boutique shopping, and maritime allure. Your Cape Cod summer starts here. Rental Terms: Summer Weekly: $7,000 Per Week

Chip Chop is the legendary 20-acre beach compound set on Vineyard Sound. The property has lived large in Martha's Vineyard lore since the 1940s when it was built for celebrated Broadway star Katharine Cornell. For many decades it has hosted a broad spectrum of well-known figures from the worlds of literature, theater, cinema, and politics. A mile of private shoreline surrounds the property, including 2000 feet of sandy beach on the exquisite swimming waters of Vineyard Sound, and a large swath of sandy beach on Lake Tashmoo. Features include a two bedroom main house, outside of which sit the Pond Cottage and the Ocean Cottage, two separate, detached bedroom suites. There are also two elegant guest houses, "Naushon" and "Cuttyhunk", which offer astonishing water views on Martha's Vineyard. The swimming pool overlooking Vineyard Sound with views of the mainland beyond is simply stunning. A Har-Tru tennis court is discretely nestled in a private corner of the property. Additional sleeping space is available in the Rose Cottage, featuring two bedrooms and one bath, full kitchen, and a gorgeous laundry facility. Supremely stylish and yet consummately casual, this famed Martha's Vineyard compound is the perfect setting for your dream Martha's Vineyard getaway.

Legacy Properties Sotheby's International Realty is proud to present Rising Sun, located at 99 Sols Cliff Road in Bar Harbor. This is the perfect home to host multi-generational family gatherings. Enjoy perfect privacy right on Frenchman's Bay, with magnificent vistas of the open ocean and panoramic views from inside that include Bald Porcupine, Ironbound, Egg Rock, and the Thrumcap Islands. You'll not find such ocean views and intimacy with the water anywhere else on Mount Desert Island (MDI). Located at the very end of a series of private roads off Main Street, Rising Sun offers unmatched privacy while being only minutes from the center of Bar Harbor. This unique combination provides great privacy with proximity to the center of Bar Harbor (a five to eight-minute drive), the nearest Park Trails (a pleasant ten-minute walk), Ocean Drive (seven minutes), and the nearest Island Explorer bus stop (a fifteen-minute walk). The very private road is as safe and beautiful as Acadia's Carriage Roads and bounds the National Park. Walk ten minutes to Schooner Head Trail, which leads north to Compass Harbor and south to Schooner Head, Anemone Cave, Sand Beach, and the Ocean Path. Your early morning walk with your dogs will be a highlight of any day. Families with kids will especially enjoy the resident wildlife—deer, turkeys, a red fox family, marmots, weasels, cormorants, eagles, osprey, and seals all visit frequently. Despite the private location, the home is only a five-minute drive or ten-minute bike ride to the center of Bar Harbor. The ocean frontage at Rising Sun is significantly different from many other homes. At low tide, other locations may have mud flats, but at Rising Sun, the granite rocks extend into deep water, providing stunning views at all times. Sit on the rocks and dip your toes in the ocean. The home is designed for comfort, with central air conditioning and a whole house air filtration system that circulates and replaces the inside air with outside air four times a day. The natural cooling from the ocean breeze is complemented by strong cross-ventilation. For those looking to exercise, a variety of options exist, including dumbbells ranging from 5 to 75 pounds, a stationary exercise bike, a yoga wall with mats and straps, and outdoor activities like walking, jogging, biking, or playing games on the lawn. Nearby, you'll find a facility with an Olympic-sized pool, running track, weight and exercise room, basketball court, tennis courts, and a baseball field. The hot tub, nestled in a rock outcropping, offers beautiful views of Frenchman's Bay. Cooking enthusiasts will love the well-equipped kitchen, complete with herbs, spices, and professional-grade tools, all with breathtaking ocean views. Enjoy peaceful, star-filled evening strolls along the private road, as beautiful as Acadia's carriage roads. Early risers can delight in morning walks, possibly accompanied by wildlife, to Compass Harbor for stunning island views. In blueberry season (late July to mid-August), pick wild blueberries from the trail. Whether you seek relaxation or adventure, Rising Sun offers the perfect balance. Enjoy a week or two of paradise, and bring your dogs—they’ll love it too! The weekly rental rate for up to six guests is $13,000.00. Each additional guest, up to the maximum of 12, will be charged $805.00. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Legacy Properties Sotheby's International Realty is proud to present Sound of the Sea, located at 100 Sols Cliff Road in Bar Harbor, Maine. Sound of the Sea is the perfect oceanfront luxury vacation rental home for families and their furry friends. Nestled in the trees at the end of a private road, this unique retreat offers breathtaking views and unforgettable experiences for everyone. Sound of the Sea boasts a secluded oceanfront setting with large rocky outcroppings leading directly into Frenchman's Bay. Unlike many other rentals near Acadia, low tide reveals more beautiful rock formations and tide pools instead of mud flats. Despite its private location, it’s only a five-minute drive to Bar Harbor’s restaurants, shops, and attractions. Amenities and Features Private Oceanfront: Enjoy deep waters at both high and low tides, with stunning granite rock formations. Screened Porch: Perfect for family dining with sea views, whether for morning coffee, afternoon tea, evening cocktails, or dinner. Michelin-Star Kitchen: Modeled after Manhattan restaurants, featuring sharp knives, a well-stocked pantry, and professional-grade tools. Modern Connectivity: High-speed cable internet, free Wi-Fi, land-line telephone service, excellent cell service, and TVs in each bedroom plus a large screen TV in the Turret Room. Comfortable Living Spaces: Cozy couches and chairs, perfect for reading, chatting, snoozing, or watching the surf. Enjoy puzzles and board games in the living room. Outdoor Activities: Half-court pickleball, nearby golf, tennis courts, and surf-casting equipment provided. Scenic Walks: Private road as beautiful as Acadia’s carriage roads, ideal for morning and evening strolls under the stars. Wildlife: Frequent sightings of deer, turkeys, foxes, eagles, osprey, cormorants, seals, marmots, and more. Bird Watching: The third-floor outdoor deck, "Eagle Watch," offers a magnificent spot for bird enthusiasts. Top-Notch Comfort and Convenience Central Air Conditioning: Keeps the house comfortable even during heat waves. Air Filtration System: Ensures pure, delightful ocean air throughout the house. Plenty of Hot Water: Unlimited hot water for all your needs. Whole House Emergency Generator: Powers the entire house, including air conditioning, during power outages. Proximity to Bar Harbor: Just a five-minute drive to the village, providing privacy without the long drive required by other locations. Benefit from a special discount when choosing payment via check or wire transfer instead of credit card. Contact Legacy Properties Sotheby's International Realty for more information on this exclusive offer.

Stunning post-and-beam waterfront retreat with sweeping views of Sengekontacket Pond, a private sandy beach, four bedrooms plus two bonus sleeping areas, three full baths, two half baths, and an outdoor shower. Guests enjoy direct pond access along with kayaks and paddleboards included in the rental, perfect for easy Vineyard summer days on the water. Designed for effortless one-floor living, the home features soaring exposed beam ceilings and expansive walls of windows that seamlessly connect indoor and outdoor spaces. The great room is the heart of the home, offering panoramic water views and comfortable gathering space. A chef’s kitchen with premium appliances and generous counter space flows beautifully into the dining and living areas, making entertaining relaxed and enjoyable. The primary suite is privately situated in its own wing, creating a peaceful retreat. Three additional bedrooms are anchored by a shared living area and screened porch, offering ideal separation for families or guests. Flexible sleeping arrangements continue with a pull-out sofa in the office, as well as a separate cottage featuring a TV lounge, pull-out sofa, and half bath perfect for teens, extended family, or overflow guests. Tucked within a quiet waterfront enclave yet conveniently close to all down-island towns, this exceptional vacation rental offers the perfect balance of privacy, comfort, and easy access to everything Martha’s Vineyard has to offer.

Pond Front Luxury Retreat Discover this stunning 7-bedroom, 9-bathroom estate set on 9 private acres along Martha’s Vineyard’s picturesque South Shore. This newly constructed property masterfully blends elegance, comfort, and breathtaking water views. Property Highlights: Heated saltwater pool & spa (16' x 42') for ultimate relaxation Expansive screened porch with a wood-burning fireplace & soaring 11-ft ceilings Gourmet chef’s kitchen featuring Thermador appliances, quartz countertops & a spacious island Butler's pantry complete with additional refrigerator and dishwasher Outdoor kitchen perfect for al fresco dining Outdoor kitchen perfect for al fresco dining Multiple suites & private decks, offering stunning views & tranquil privacy Primary suite on the main floor with a spa-like ensuite & private outdoor shower Five bedroom suites with king beds and private baths, 2 additional guest bedrooms share a hall bath Media room, reading nook & lounge areas designed for both entertainment & retreat Two-car garage with an electric vehicle charger Step into the grand living room, where floor-to-ceiling glass doors lead to a mahogany deck, heated pool, and a private boardwalk to the water. Whether you're kayaking, paddle boarding, or simply soaking in the scenery, this home offers unparalleled waterfront living. Located just minutes from Morning Glory Farm, Edgartown Village, Vineyard Golf Club, and the airport, this secluded haven provides effortless access to the island’s finest offerings. Your dream Vineyard escape awaits! *2 week minimum preferred

Tucked away at the end of a private cul-de-sac in Katama, this expansive property offers the perfect blend of privacy, comfort, and style. The sun-filled first floor boasts an open-concept layout featuring a chef’s kitchen, dining area, and a spacious main living room, ideal for entertaining or relaxing with family and friends. Two additional sitting rooms on the main level provide ample space for guests to unwind. The luxurious primary suite with an en suite bath is also located on the first floor, along with a convenient powder room and one of two laundry areas. The second floor features three beautifully appointed guest suites and a second laundry room for added convenience. The finished lower level is a standout feature, offering an additional king bedroom, full bath, large living area, game room, sauna, home gym, and additional sleeping accommodations, perfect for larger groups or families. Step outside to your own private oasis, a meticulously landscaped, fenced-in yard with a heated pool and hot tub, perfect for enjoying warm summer days and starry Vineyard nights. Located just minutes from South Beach and downtown Edgartown, this Katama retreat offers the ideal Vineyard vacation experience. *Available for 2 consecutive weeks only summer 2027

Experience the pinnacle of Vineyard living at this extraordinarily updated 9-acre estate, nestled within the exclusive Herring Creek Farm Association. Set along the tranquil shores of Edgartown Great Pond, this 10,000+ square foot residence offers unmatched privacy, refined elegance, and direct access to pristine beaches. The main level showcases timeless design with a grand foyer, sweeping staircase, sunlit formal dining room, gourmet chef’s kitchen, and multiple living areas designed for both relaxation and entertaining. A separate guest wing ensures comfort and privacy for visitors. French doors open to a resort-style outdoor oasis with a heated pool, expansive bluestone patio, and a covered porch with fireplace for elegant al fresco dining. Upstairs, five spacious bedrooms include an expansive primary suite featuring a private balcony with water views, a large walk-in closet, private office, and spa-like bath. Spend your days lounging poolside, enjoying sunset views over the Pond, or following a short private path to your own sandy beach. The Association’s exclusive Atlantic beach is a short golf cart ride away. Framed by beautifully landscaped grounds and open farm fields, this exceptional property offers total seclusion just minutes from downtown Edgartown.