Sophisticated Contemporary Living with Exceptional Indoor-Outdoor Amenities

Aquinnah, MA

Experience the beauty and tranquility of Martha’s Vineyard from this exceptional custom-built luxury post-and-beam home, nestled in the heart of the rolling Aquinnah hills. From the upstairs deck, enjoy breathtaking sunsets over Vineyard Sound and the Elizabeth Islands—a spectacular backdrop for evenings spent with family and friends.Designed with impeccable style and craftsmanship, this beautiful home combines dramatic architecture with relaxed coastal elegance. The magnificent great room features soaring cathedral ceilings, an inviting gas fireplace, and an expansive open-concept layout that creates a wonderful gathering space. Artisan stonework, rich wood details, and thoughtfully selected furnishings lend warmth and character throughout.The spacious chef’s kitchen is beautifully appointed with marble countertops and an oversized island, flowing seamlessly into an additional dining area perfect for leisurely breakfasts, family dinners, and entertaining. Tastefully decorated with upscale furnishings, the home offers the perfect balance of sophistication, comfort, and casual Vineyard living.With five bedrooms and three-and-a-half bathrooms, there is plenty of room for families and friends to vacation together. The main-level primary suite, complete with a private bathroom, occupies one end of the home, while two guest bedrooms share a Jack-and-Jill bathroom at the opposite end. A convenient half bath completes the main floor. The lower level offers two additional bedrooms, a full bathroom with a tub, and a dedicated game area for younger guests. Four queen bedrooms, along with a bunk room sleeping three and a pull-out sofa, provide flexible accommodations for your group. Laundry facilities on both floors add to the convenience.An unforgettable Aquinnah location puts some of Martha’s Vineyard’s most beautiful beaches within easy reach by bike or car. Spend the day beneath the dramatic, colorful clay cliffs, enjoy the peaceful shoreline at Lobsterville Beach, or take a sailboard out onto the water. For a memorable Island outing, catch the bike ferry to Menemsha, browse the seafood markets for fresh lobster, and enjoy the charm of this historic fishing village.After a day of beachcombing, swimming, and exploring, return home to relax on the deck and watch the sun sink into Vineyard Sound. For a special evening out, the nearby Outermost Inn offers a memorable dining experience in a spectacular setting.Whether you are planning a multigenerational family vacation, a getaway with friends, or a special celebration, this distinctive Aquinnah retreat offers the space, craftsmanship, and setting to make your Martha’s Vineyard stay truly unforgettable.Additional amenities: High-end construction and finishes, laundry facilities on both levels, and a game area. Dogs considered. Weekly transferable ferry tickets may be available during the high season; please inquire for details.A remarkable home, a spectacular setting, and sunsets you will remember long after your vacation ends.

West Tisbury, MA

Walk or bike to Lambert's Cove Beach from this private, 3500 sq. ft. Country home with SPA POOL. This property is set in an idyllic Vineyard rural setting overlooking beautiful gardens in the Longview area of Lamberts Cove Rd, West Tisbury. This is a central location that is about a half mile walk to Lamberts Cove Beach and approx. 4 miles drive from the village of Vineyard Haven. Ice House Pond is just a hop away - great for a cool evening dip. The first floor is light filled with an open family styled living design. A sunny spacious living room with glass on two sides, opens to additional sitting area, all overlooking the large front deck. There is a side door from here out to the wonderful spa pool if you want to take a few laps in the spa pool. The dining area, also on the front side of the house has an oversized round custom wood table for family meals. The big chef's kitchen is bright with spacious marble counters, double ovens and is great for family feasts. A master bedroom with a queen bed plus one & a half baths complete this floor. First floor all flows graciously out to large front deck overlooking the yard and beautiful gardens and hammock. There's a great outdoor shower that leads back into the laundry room -perfect for after beach rinse offs! The staircase leads you up to the middle of the second floor into large L-shaped study area this is a walk thru room with two twin beds and chair for reading or relaxing. This room opens to the upstairs rubber floored outdoor deck which has a beautiful new railing all around. This is a fabulous spot for sunbathing or sunset drink.To the left there are two bedrooms and a studio room. The first bedroom is an attractive king bedroom with a skylight leading to a full bath and also has a door to the deck. Another nice bedroom also has a skylight and a queen bed. There is another full bath, and there's also an extra sunroom/studio with another king bed.On the side of the study is the sun-filled, oversized master bedroom. This has a king bed with big sitting area and an exterior stairway leading to lower deck (with spa pool).The fabulous home is beautifully decorated, and the large open areas both inside and out, allow for family to be together and have their privacy also. It's perfect for outdoor family summer games or for each person to find their own quiet nook.**Staying in West Tisbury allows you to get a resident's pass to use the private West Tisbury Lambert's Cove Beach. Walk on and Parking passes are available to purchase.***Spa pool is heated & approximately 15’ X 12’. It is designed to be used as an athletic machine. A person turns on wave control & swims in place against current. Children must be accompanied by adult at all times. Dogs are considered with additional pet & cleaning fee.

Oak Bluffs, MA

Walk to Oak Bluffs Harbor, beaches & Village! Set on a quiet side road but steps from the action, this location is ideal for a summer getaway. The open living-dining room has high beamed cathedral ceilings with windows on three sides. There is a full kitchen w/snack bar, full bath, laundry and a master bedroom on the first floor. This bedroom opens to its own small deck on the front of the house. There is a great enclosed porch room with wicker furniture and extra dining, game night or a quiet summer reading area. An additional front deck overlooks the front yard.Up the spiral stairs and you have 2 delightful bedrooms on either end of the hallway and a full bath in the middle.The bedrooms have 2 twin beds with cathedral ceilings and skylights. There is AC in the bedrooms along with ceiling fans. Attractive and comfortably decorated for a carefree summer lifestyle. Availability for 2027!Baths: 2Bedrooms: 1 queen2 twins2 twins

Chilmark, MA

This exquisite contemporary home includes a key to private beach access to Black point Beach, is a short walk to Lucy Vincent beach, and is ideal for laid-back Vineyard living or elegant entertaining. With careful attention to detail, the open floor plan for the common areas brings the outdoors inside, with spectacular sunshine and sweeping views of the ocean and hillsides. Privacy in the living quarters with a den upstairs allow for downtime and quiet moments alone. The unique setup of three bedrooms and a common area on the lower floor provides a sunny place to relax while the rest can entertain on the main and upper floors with a fireplace in living room. The two master suites are on the main floor, one complete with Jacuzzi tub. There's a full gourmet kitchen, updated entertainment system. Other features include central a/c, a separate laundry/utility room, 2 decks, (one complete with screens), a private balcony, 2 outdoor showers, a large gas BBQ, and over 3 acres. This house is one that you'll never forget, and you'll want to come back to year after year. Finally, the backyard is large enough for any of your summer needs, tented parties or large gatherings or weddings. The grounds are well kept. There is a built-in fire pit, low cut brush for the view and blueberry bushes. ADA/Handicap compliantAvailability for 2027 includes June 26-July 3; July 3-July 10; August 21-August 28; August 28-September 4, 2027!

Oak Bluffs, MA

STEPS FROM THE BEACH! This enchanting Oak Bluffs Victorian will absolutely delight you and your family. You can SEE and FEEL the essence of the OCEAN from your rocking chairs. The inviting wrap around porch has beautiful views over Waban Park to the water. You'll be just steps from the beaches and simply a skip into town. The living room is fabulous for family get togethers w/ a spectacular fieldstone fireplace and charming French doors. Large dining room is great for sit-down meals for all.The modern kitchen with stone countertops is a chef's delight. The first floor also has a queen master bedroom w/ full bath with private entrance. Two separate stairways lead upstairs to three more appealing bedrooms. All w/ exciting cathedral ceilings and original white shiplap walls. One bedroom has two twin beds, and another has a queen bed. These share a full bath in hall. Enjoy the balconies with water views and ocean breezes. The 2nd master bedroom has a king bed with private bath w/ claw ft tub and handheld shower. Extra little nooks provide spots for reading or a little get-away. Availability for 2027 summer!

Chilmark, MA

Charming Contemporary near Lucy Vincent and Menemsha Beaches!Step into this light-filled contemporary home w/skylights, inviting open layout & delightful design details throughout.With three bedrooms (one on first floor) & 2 full baths (plus outdoor shower) this home offers comfort and style in a peaceful up-island setting. Enjoy indoor-outdoor living w/ multiple decks and a screened-in porch, perfect for morning coffee, grilling or relaxing after a day at the beach.Located less than 3 mi from Chilmark center, you'll have rights to coveted access to the private Lucy Vincent Beach (purchase passes) and also Menemsha Beach. Menemsha, a quintessential New England fishing village is known for its fresh seafood markets, charming boutiques, restaurants and working harbor- an ideal and popular spot for sunset, lobster, swimming and strolls. A wonderful get-away with the best of Martha's Vineyard Coastal charm.You won't want to leave!Availability for 2027!

West Tisbury, MA

Enjoy a relaxing Martha’s Vineyard vacation in this beautiful, sun-filled contemporary home, ideally located near Long Point Beach, managed by The Trustees of Reservations. Centrally situated between the Island’s towns, with convenient access to paved roads and nearby State Forest bicycle paths, this inviting retreat offers the perfect blend of beachside adventure, comfort, and convenience—just four miles from Edgartown.Spend your days enjoying the spectacular south-shore ocean beach, where you can swim in the waves, stroll for miles along the shoreline, or explore the calmer pond-side waters with younger family members. Whether you prefer a day at the beach or an afternoon biking through the Island’s scenic woodlands, this home is an ideal base for your Vineyard adventures.Built in 2008–2009 and professionally decorated, the home features an attractive, comfortable interior designed to make your vacation effortless and enjoyable. Central air conditioning and wood floors throughout add to the home’s appeal, while the inviting living room offers a gas fireplace and a 50-inch plasma TV—perfect for relaxing after a day in the sun.The well-appointed kitchen features granite countertops, a refrigerator with automatic ice maker, and a breakfast bar with seating for four. Gather for meals around the distinctive zinc-top dining table or enjoy outdoor dining on the deck at the teak table.With four bedrooms and three-and-a-half bathrooms, the home comfortably accommodates families or two families vacationing together. Two queen primary bedrooms each feature a private bath with beautiful ceramic tile finishes. An additional bedroom offers two twin beds, while the fourth bedroom features a bunk bed with a double bed below and a twin above. These bedrooms share an additional full bathroom.Outdoor living is equally inviting, with a welcoming farmer’s porch, a spacious deck, and an open yard where children can play. After a day at the beach, rinse off in the outdoor shower, fire up the gas grill for dinner, or head downstairs for a friendly game of ping-pong. Wi-Fi and a DVD player provide additional entertainment for relaxing evenings at home.With its sunny interiors, thoughtful amenities, generous bedroom accommodations, and outstanding access to Long Point Beach and the Island’s bicycle paths, this charming home offers everything you need for a memorable Martha’s Vineyard vacation.A wonderful Island retreat for families, beach lovers, and anyone looking to enjoy the very best of summer on Martha’s Vineyard.Baths: 3.5Bedrooms: 41 queen1 queen1 double; 1 twin2 twins

Oak Bluffs, MA

Step into Martha’s Vineyard history with a modern twist in this beautifully preserved gingerbread cottage nestled in the peaceful Vineyard Highlands neighborhood of Oak Bluffs. Just steps from Sunset Lake and a pleasant walk to the beaches, ferry, and downtown, this inviting retreat offers the perfect blend of timeless island charm, relaxed outdoor living, and a convenient location.Inside, vintage character meets everyday comfort. The first floor features a bright living room, a cozy sitting area perfect for reading or conversation, and a fully equipped kitchen that opens onto a side porch—an ideal spot for morning coffee or a leisurely lunch in the fresh ocean air. The farmhouse-style dining area comfortably seats six, while the spacious back deck features a large picnic table for memorable outdoor dinners under the stars.Surrounded by a generous yard, the deck overlooks a welcoming outdoor space complete with a fire pit—perfect for gathering with family and friends after a day exploring the island. A full bathroom with a tub and shower is conveniently located on the first floor, and an outdoor shower provides a refreshing way to rinse off after a day at the beach.Upstairs, the front bedroom features a queen bed and opens onto a private second-story porch, the perfect place to enjoy morning coffee or unwind with a glass of wine in the evening. Two additional bedrooms offer a full-size bed and two twin beds, comfortably accommodating families or small groups.The location makes it easy to enjoy all that Oak Bluffs has to offer. Take a stroll to Ocean Park, explore the shops and restaurants along Circuit Avenue, visit the beloved Flying Horses Carousel, or spend the day at Inkwell Beach. The ferry is also within walking distance, making arrival and departure convenient without relying on a car for every outing.After a day of beachcombing, shopping, and island adventures, return to your peaceful cottage to enjoy the ocean breeze drifting through the porches, dinner on the deck, and evenings beneath the Vineyard sky.With its historic gingerbread charm, inviting outdoor spaces, and walkable location, this delightful cottage is the perfect home base for a memorable Martha’s Vineyard getaway.Beds: 1 queen bed 1 full bed 2 twins

West Tisbury, MA

Escape to Martha’s Vineyard in this beautifully updated Farmhouse Colonial, set on two private acres along a quiet country road in Vineyard Meadow Farms. Offering a wonderful blend of privacy, comfort, and classic New England charm, this inviting home is an ideal retreat for families looking to enjoy the best of Island living.Spend your days at nearby Long Point Beach, one of Martha’s Vineyard’s most beloved coastal destinations, or enjoy access to the beautiful Lambert’s Cove Beach, a special privilege for West Tisbury residents. Whether you prefer long walks along the shore, swimming in the ocean, or simply relaxing in the peaceful surroundings, this location offers a wonderful setting for a memorable summer vacation.Inside, the home features a welcoming, open-concept layout designed for spending time together. The comfortable living room flows naturally into the dining area and fully equipped kitchen, where a convenient snack bar provides the perfect spot for casual breakfasts, afternoon treats, or gathering while meals are prepared.The home offers four bedrooms, along with a versatile media room, providing comfortable accommodations for families and friends. Upstairs, three bedrooms include a queen primary suite with a private bathroom and two additional bedrooms with twin beds that share a full hall bath. The first floor features an additional queen bedroom, a media room with a futon, and another full bathroom—an ideal arrangement for children, extended family, or guests seeking a little extra privacy.Step outside onto the expansive deck, where outdoor dining and relaxed summer evenings become part of the experience. Enjoy family meals in the fresh Island air, unwind after a day at the beach, or simply appreciate the quiet, private setting.Central air conditioning keeps the home comfortable throughout the summer, while the Bluetooth-enabled sound system lets you set the mood with your favorite music.With its spacious grounds, flexible sleeping arrangements, inviting living spaces, and convenient access to some of the Island’s most beautiful beaches, this charming West Tisbury farmhouse is a wonderful home base for a classic Martha’s Vineyard vacation.Relax, reconnect, and enjoy the simple pleasures of summer on the Vineyard.Bedrooms:1 queen1 twin1 twin1 queen