luxury houses for sale Oak Bluffs, United States

Gorgeous waterview home tucked into a corner of Vineyard Haven village. This property is a landmark thanks to its distinctive red door and the stunning flowerbeds visible to passersby. The quaint exterior disguises what greets the visitor upon entering - a sophisticated combination of traditional and modern design within a completely renovated home (most recently in 2008-2010 and then in 2019). Consider the fact that the house has four large bedrooms all with modern ensuite bathrooms PLUS an office PLUS a separate den PLUS an extra full bathroom. The primary bedroom with its private deck occupies the entire third level of the home and enjoys spectacular 120-degree harbor views of the multitude of wooden sailboats on their moorings and the ferries coming and going. This is a home for entertaining friends and family thanks to its open floor plan that opens onto a large deck. The home is located at the far end of Main Street in what is a bustling part of the village, and yet when one steps inside, the hubbub disappears as the door closes behind you. The cobbled driveway fits two cars and there is also a grassy driveway that leads to a detached two-car garage. The garage is currently configured to accommodate one car in the off-season. The other half of the garage is an art studio that could be used as is or repurposed as an office or gym. Tucked between the house and garage is a peaceful area with bluestone pavers that lead to an outdoor shower - the perfect place to rinse off after a day at the beach or out kayaking or paddle-boarding.

Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury. Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen with top-of-the-line appliances and custom butcher block island. Attached to the kitchen is a welcoming dining room and wet-bar and a screened porch with garden views. The multiple spacious living areas are flooded with natural light and fireplaces perfect for both entertaining and everyday living. The second floor features 3 beautifully appointed bedrooms with 3 updated tile baths. Additionally, a serene sitting room awaits, complete with built-in bookshelves, creating the perfect place for relaxation or study. Venture to the third level and discover a hidden retreat—a charming bedroom offering privacy distant water views. Outside, there is an expansive yard, a rare find in-town, offering ample space for outdoor gatherings and gardening. The detached 2-story 1-bedroom barn-style guest house beckons, a charming retreat with its own private back deck. From the elegant facade to the meticulously landscaped grounds, every aspect of this property reflects a rich history and a timeless appeal. The perfect in-town location with easy access to Downtown Vineyard Haven restaurants, shops, beaches and ferry.

A desirable location in Vineyard Haven and just steps away from Owen Little Beach on Vineyard Sound. This home offers privacy and endless possibilities while being close to Downtown Vineyard Haven shops, restaurants, harbor and ferry. The home features an inviting porch overlooking a spacious lawn and peaks of Vineyard Sound in the distance. The first floor includes an eat-in kitchen, dining room, open living room, full bath and a convenient laundry room. The second floor includes 3 bedrooms and a bathroom featuring an antique claw-foot tub. Stairs lead to a 3rd level that can be finished for additional living space. With lots of recent updates, 26 Daggett Ave is a special setting and awaits a new owner’s vision.

Discover the charm of Old Lighthouse Road in Vineyard Haven with this recently renovated home that offers both comfort and versatility. Situated in a quiet neighborhood, this property presents an excellent opportunity for those seeking a cozy dwelling. Thoughtful updates and attention to detail shine throughout. The kitchen has been tastefully remodeled, boasting modern appliances, butcher block countertops, and plenty of storage space. The home features 2 spacious bedrooms, a second floor loft and 2 full baths. The standout feature of this property is the expansive 500 sq. ft. renovated shed, offering endless possibilities. Whether you envision it as a workshop, a home office, a hobby space, or additional storage, this versatile area is ready to adapt to your specific needs. Outside, a well-maintained yard surrounds the home along with a spacious deck. Old Lighthouse Road presents an idyllic setting, providing a peaceful retreat while still being conveniently close to the amenities of Vineyard Haven. Explore the vibrant downtown area, local dining options, and enjoy easy access to Owen Park beach.

Discover tranquility on Martha's Vineyard with this 4BR, 2.5BA Cape-style home, privately set on 1.65 acres with deeded Lake Tashmoo beach access. An open layout features a spacious kitchen with new quartz counters, flowing into living/dining areas and a deck overlooking serene landscapes. Designed by a landscaper owner, the outdoor setting is a natural oasis. The main level includes a primary suite and mudroom with laundry. Upstairs hosts 3 bedrooms and a bath. Amenities include a full basement, propane HVAC, outdoor shower, sunset-viewing front porch, nearby tennis courts and public boat launch. A unique blend of privacy, comfort, and exclusive beach access.

Welcome to this charming four-bedroom residence nestled in Smith Hollow. Situated on a .90-acre lot, this property offers a perfect blend of space, comfort, and investment potential. As you enter, you'll be greeted by an expansive open kitchen, living and dining room that leads to an inviting screened in porch and deck off the back of the house. The two bedroom wings flank the main living space, providing ample space for family and guests, ensuring everyone can enjoy their own private retreat within the home. One of the standout features of this property is the expansive backyard, which not only offers plenty of room for outdoor activities but also presents the perfect opportunity for a pool with town approval. Just over 2.5 miles to Edgartown Village, with easy access to the bike path at the end of the road making this location ideal. This property also boasts impressive rental history that adds to this well-rounded offering, look no further.

This NEWLY-CONSTRUCTED Greek Revival home on Main Street entering the historic village of Edgartown. This stately classic luxurious home has all the timeless style of a traditional home and the architectural details and upscale amenities the modern buyer desires. With over 4,600 sq ft of living space on three levels, 4 bedrooms and 4.5 baths, and a private backyard with a gunite swimming pool, the home offers plenty of room for you, your family, and houseguests. The 1700 sq ft lower level with 9 ft ceilings can also be finished off to provide additional living space, a media room, and a bedroom suite. Attention to many high-end details too numerous to list including custom Carrara marble stone bathrooms, chef's kitchen with a 3-inch thick marble kitchen island countertop, smart home system, hardwood flooring, high efficient heat and central air conditioning, on-demand hot water, central vacuum and much more. The location is extremely convenient, with the harbor front just down Main Street along with the shops, restaurants, and galleries in the village and in an area of substantial new homes that are part of the expanding village center.

Located within the heart of the highly sought-after historic district of Edgartown, this 4-bedroom residence on South Summer Street offers a unique blend of timeless elegance and historical detail. Built in 1780, this home stands as a testament to Edgartown's rich architectural heritage with its classic New England design, complete with a white picket fence. Enter through the welcoming foyer, which leads to a spacious living room with original wide plank hardwood floors and classic moldings. The living room and formal dining room feature fireplaces which create an inviting space for gatherings and entertaining. Primary bedroom suites can be found on both levels of this home. The property includes coveted off-street parking and a 1 car garage. Enjoy the convenience of living in the heart of downtown Edgartown. South Summer Street is a short distance to boutique shops, restaurants, art galleries, and the iconic Edgartown Harbor. This property represents a unique opportunity for those with a vision for restoration.

Nestled in the heart of Edgartown Village, this property, known as the Captain Ellsworth West House, boasts a rich historical legacy while showcasing exceptional craftsmanship, making it one of the most remarkable homes in the area. This renovated Captain's home seamlessly combines historic charm with modern elements, resulting in a truly captivating residence. Originally built in the 1860s, the house underwent a meticulous renovation by Hutker Architects in 2013, breathing new life into its storied past. The main house spans four floors, providing expansive living spaces. Stepping onto the private covered porch, one is greeted by the warmth of an inviting porch, wood-burning fireplace and breathtaking views of the exquisitely landscaped grounds. This exceptional property encompasses over 7,000 square feet of thoughtfully designed living space, making it an ideal in-town compound for discerning buyers seeking a spacious and comfortable home for hosting family and friends. Adjacent to the main house stands a detached two-story Carriage House, which adds another layer of luxury and functionality to the property. A pool cabana provides a convenient space for relaxation. The private outdoor living area, complete with a gunite pool, built-in whirlpool spa, and a serene bluestone terrace, is ideal for lounging poolside. This home is poised to create cherished memories for years to come.

Welcome to 106 Peases Point Way South in Edgartown. This stunning new 4-bedroom home offers the perfect blend of elegance, comfort, and convenience. Nestled in a desirable location, you'll find yourself just a short stroll away from downtown Edgartown, where you can enjoy the vibrant atmosphere, exquisite dining options, and boutique shopping. Step inside and be captivated by the sun-soaked interiors of this home. The spacious and elegant living area boasts a sunroom, complete with a charming brick fireplace, creating a cozy and inviting atmosphere. French doors open up to reveal a stone patio and a pergola, seamlessly connecting indoor and outdoor living spaces. The gourmet kitchen is a chef's delight, featuring top-of-the-line appliances and sleek countertops. Retreat to the luxurious primary suites, located on both the main and second level. Both primary bedrooms feature an en-suite bathroom featuring a soaking tub, a walk-in tile shower, and dual vanities. Two additional generously sized bedrooms provide comfort and privacy for family members or guests, and they share access to a beautifully appointed bathroom. One of the standout features of this remarkable home is the finished basement, providing additional living space, game room and full bath. The exterior of the property is equally impressive, with a meticulously landscaped yard and a stone patio, perfect for outdoor gatherings and al fresco dining. And with a permit in place for a pool, you have the opportunity to create a private oasis for cooling off during the warm summer months. The property also includes a one-car garage, ensuring convenience and ample storage space. Don't miss out on this remarkable Martha’s Vineyard home.

Welcome to this classic cape-style home nestled in downtown Edgartown. This charming residence offers a blend of timeless elegance and modern comfort, boasting four bedrooms, three and a half baths, along with a living room with fireplace, den/family room with fireplace, and attached one-car garage. Adjacent to the main house, the one-bedroom bunkhouse provides a private sanctuary for guests or can serve as a separate studio or office space. It features its own kitchenette, bedroom/sitting area, and full bathroom, offering a comfortable and flexible living arrangement. Outside, the beautifully landscaped backyard provides a serene oasis for outdoor entertaining and relaxation. The patio is perfect for enjoying a good book or lounging in the sun, while the lush green lawn and mature plantings make you want to lounge the day away. in this location, you can stroll along picturesque streets lined with historic homes, visit boutique shops, and art galleries, and experience all that Edgartown has to offer.

Uncover unparalleled Martha’s Vineyard opulence within a sprawling 22-acre estate. Immerse yourself in the timeless elegance and meticulous craftsmanship of the 7-bedroom , 10-bathroom main home , designed by the renowned architect, Robert A.M. Stern. From the grand foyer to the post & beam living room, each detail exudes sophistication. Revel in the warmth of multiple fireplaces and experience culinary delights in the superbly designed gourmet kitchen. This residence is a luminous haven, where natural light steals the spotlight. Step outside and discover a remarkable pool and pool house with a fully-equipped gym, sauna, and massage room. A newly constructed home and cottage complement the main residence, offering versatile options for guests. The pastoral landscape is adorned with a pond and Amish barn, a testament to craftsmanship and tradition. Located in the exclusive Boldwater Association, residents enjoy, tennis, pickleball, a boat landing, and a private Atlantic Ocean beach.

Uncover unparalleled Martha’s Vineyard opulence within a sprawling 22-acre estate. This includes a main residence designed by the esteemed architect Robert A.M. Stern, a charming guest house, an authentic Amish barn, a pool house with gym, sauna and massage room, and a picturesque man-made pond. Immerse yourself in the timeless elegance and meticulous craftsmanship of the 7-bedroom , 10-bathroom main home. From the grand foyer to the post & beam living room, each detail exudes sophistication. Revel in the warmth of multiple fireplaces and experience culinary delights in the superbly designed gourmet kitchen. This residence is a luminous haven, where natural light steals the spotlight through meticulously crafted windows, French doors, transoms, and skylights. This private residence is a luminous haven where natural light steals the spotlight through meticulously crafted windows, French doors, transoms, and skylights.

Private Oyster Pond waterfront residence on 3-acres with a private dock, manicured lawn, and beautiful gardens. This traditional 5 bedroom, 4.5 bath home boasts a unique design flooded with natural light. Incredible views of Oyster Pond can be enjoyed from the gourmet kitchen and the spacious living room featuring cathedral ceilings with exposed beams and a stone fireplace. The dining area offers access to the spacious mahogany sundeck overlooking the private heated pool and gardens. The first-floor primary bedroom includes a home office and views of Oyster Pond. The guest bedrooms and baths are on the lower level with private access to the pool area. The mudroom entryway provides convenient access to the two-car garage. A guest apartment located above the garage with a full kitchen, bath, laundry, a spacious living room and bedroom. This thoughtfully designed space offers guests ample privacy. The expansive lawn stretches to the edge of Oyster Pond where you can enjoy clamming, kayaking, paddle boarding, swimming, and boating from your private dock. Oyster Pond residents enjoy exclusive access to the Pond and the sandy beach on the Atlantic Ocean. A truly special Martha’s Vineyard escape in one of the Island's most coveted locations.

Unparalleled Chappaquiddick waterfront estate complete with deepwater dock, 300±-foot private beach, private 3-bedroom guest house and garage/barn, plus the unique added opportunity to acquire the private 17±-acre golf course adjacent, also suitable for horses or open space. Designed by award-winning Boston architects Albert-Righter-Tittmann and expertly crafted, this grand yet welcoming home, featured in numerous publications, is a refined modern take on traditional design. Harmonizing with the idyllic coastal scenery, the 5-bedroom main residence captures glorious wide-open views on Nantucket Sound taking in the sunset, legendary yachting regattas and July 4th fireworks. Comfortably styled and beautifully furnished, the inviting light-filled living/entertaining spaces open their doors to the breezy waterside porch. Appointed with classic shiplap paneling, the home also features a gym, sauna and high-efficiency systems. A worlds-away retreat, yet close to Edgartown village.

Unparalleled Chappaquiddick waterfront estate complete with deepwater dock, 300±-foot private beach, private 3-bedroom guest house and garage/barn, plus the unique added opportunity to acquire the private 17±-acre golf course adjacent, also suitable for horses or open space. Designed by award-winning Boston architects Albert-Righter-Tittmann and expertly crafted, this grand yet welcoming home, featured in numerous publications, is a refined modern take on traditional design. Harmonizing with the idyllic coastal scenery, the 5-bedroom main residence captures glorious wide-open views on Nantucket Sound taking in the sunset, legendary yachting regattas and July 4th fireworks. Comfortably styled and beautifully furnished, the inviting light-filled living/entertaining spaces open their doors to the breezy waterside porch. Appointed with classic shiplap paneling, the home also features a gym, sauna and high-efficiency systems. A worlds-away retreat, yet close to Edgartown village.

In an enclave of luxury homes in Katama, this 2021-built 5 bedroom, 5 bathroom property with three half-baths is being delivered turnkey with fine furnishings and artwork. The home has everything the modern buyer wants, including two primary bedroom suites (one upstairs, one downstairs), all bedrooms with ensuite bathrooms, two laundry rooms, detached guest quarters, high-end music system, a beautiful pool area, the list goes on. In addition to the 4700-sf main house with 4 ensuite bedrooms there is a Carriage House with a bedroom suite upstairs. In 3 years time this detached bedroom can be converted into full guest apartment by converting unfinished space into a living room and kitchen. The Carriage House also includes a poolhouse with half bath and a 2-car garage.

Experience the buzz of one of Katama's most desirable neighborhoods, right across from Down Harbor and next door to the Field Club and Somerset Lane. The good energy is everywhere. Here is your sanctuary amidst the hubbub, a custom-built 4700 sq ft classically styled home that feels brand new (square footage includes a finished basement). The vibe is upscale Edgartown with a coastal contemporary twist. The home is designed for entertaining an open floor plan transitions seamlessly to the stunning patio and landscaped backyard with a swimming pool and an outdoor kitchen beneath the pergola. The entryway provides a taste of things to come, with vaulted ceilings and an elegant stairway to the second floor. The chef's kitchen with top-of-the-line appliances has a large island with soapstone countertops that provides an area for casual gatherings or ample space for cooking. The substantial first-floor primary bedroom suite enjoys direct access to the deck and overlooks the backyard and pool area. Upstairs there are two large bedroom suites - plus a separate sitting area with fireplace and deck. The high ceilings provide light and openness in this elegant home. And as if all this space isn’t enough, there is a 1200 sq ft sq ft finished basement with a media room and two additional bonus rooms for overflow guests. The Carriage House is a revelation, as above the two-car garage there are spacious guest quarters with bold design choices that will appeal to your guests. At present there is a kitchenette that in 2 years zoning will allow to be expanded into a complete kitchen with a stove. A finished product home like this is not seen often in the Katama area.