luxury real estate for sale Dukes County, United States

Welcome to your dream retreat in Oak Bluffs—a magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home; it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

Gorgeous post-and-beam home built by a respected contractor. This spacious house plus detached guest quarters is on the outskirts of the village conveniently located on the way to South Beach. The property is at the end of a long driveway off Katama Road and is private and quiet. Upon arrival, you are greeted by beautiful landscaping with large beds of hydrangeas. There are 3 bedrooms in the main house, including on the first floor a large Great Room and a spacious primary bedroom suite. The living area spills out naturally onto a large fir deck. Upstairs is a secondary sitting area plus two bedrooms and a bath. There is a 2-bay garage with guest quarters upstairs. There is plenty of room for a swimming pool should the future owner want one. This is a comfortable home in the Katama Country style with lots of space for your family to make their own memories.

Welcome to Oak Bluffs! This classic colonial style 4-bedroom, 2.5-bathroom house has just undergone a complete interior renovation, promising contemporary comfort and style. As you step inside, you'll be greeted by a spacious living room adorned with a cozy gas fireplace. The open layout seamlessly connects the living room to the dining area, creating an ideal space for entertaining. The newly updated kitchen features modern appliances, sleek countertops, and ample storage space. An office, half-bath and laundry room complete the first floor. Upstairs, the primary bedroom suite awaits with plenty of natural light and a luxurious en-suite bathroom. The second-floor features 3 additional bedrooms and a guest bathroom. Outside, the newly landscaped fenced-in yard boasts a stone patio and plenty of outdoor entertaining space. An oversized screened porch completes this welcoming outdoor oasis. Located on the bike path, this location is convenient to Downtown Oak Bluffs, and nearby beaches.

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westmister Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Adding to the allure of this home is the expansive basement, spanning 890 sq. ft. and providing endless possibilities for storage, recreation, or future expansion. Don't miss out on the opportunity to make this exceptional Edgartown property your own.

Presenting one of the most outstanding real estate assets on Martha’s Vineyard. 1005 Main Street was built in 1891 and purchased in 1948 by the Singer family who have owned it since. The setting is front and center in West Chop and includes a large private beach and 210-degree views so expansive that you can enjoy sunrises and sunsets from the same chaise lounge on the deck. The views are extremely active with ferries and fishing boats passing in the distance, sailboat races, and at closer range smaller craft including perhaps your own children in a laser or kayak. There are 8 large bedrooms, 7 full baths, and a 2-bedroom apartment in the lower level. The home still exudes olde worlde charm despite all 5,050 sq ft having been completely renovated between 1995 and 2005 with new insulation, HVAC system, and updated plumbing and electric. The 400 ft of private beach is a rare asset, and the walkway down to it has been trod by many who have come to love this home and incomparable setting. Of course, with its multiple decks and spectacular views, the home has always been a prime location for entertaining friends and family and so it is helpful to have so much parking - eight spaces plus a two-car garage. The sea wall assures that this property will be here for future generations. Owners may apply separately for membership at the West Chop Club would confer a host of privileges including use of nearby middle pier for loading and unloading.

Welcome to this exquisite waterfront sanctuary boasting breathtaking views and serene surroundings on Katama Bay. This enchanting 4.40-acres waterfront property features a charming two-story home comprised of four bedrooms and three bathrooms with the addition of a private waterfront vacant land parcel. The home offers ample space for comfortable living both indoors and outdoors. As you step through the front door, you are greeted by an airy and light-filled interior, flanked with windows, that seamlessly blend with the beauty of the outdoors. The spacious living area is perfect for hosting gatherings. The highlight of this home is the expansive porch where you can enjoy your morning coffee while taking in the picturesque views of the waterfront. Imagine relaxing here as you watch the sunset over the tranquil waters. Upstairs, you will find the inviting bedrooms, each offering a peaceful retreat at the end of the day. The primary suite is a true oasis with its own private balcony overlooking the water, creating the perfect spot for relaxation. It is located in a highly desirable waterfront community on Chappy and just a short distance to Edgartown Village. Don't miss this rare opportunity to own a waterfront gem that offers a lifestyle of comfort, beauty and a unique opportunity to build your Chappy compound. You can have up to nine bedrooms with town approval on the vacant land parcel!—sold as is.

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.

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.

Edgartown building lot - almost 3/4 of an acre! Septic design for 2 bedrooms with permit in hand. Enter either off Edg. VH Road or Shady Oak Lane. Enjoy over 130 acres of conservation land right across the street with scenic walking trails to Sengekontacket Pond. The setting is barely a mile and a half from the heart of Edgartown village. Setbacks for this lot are 10 feet from sides and back and 30 feet from front and so there is ample room for a house and garage. All information should be verified by Edgartown Building Dept. and BOH.

A dramatic home with water views and over 6000 sq ft of living space. So much thought has gone into this stunning property. Immediately upon entering the visitor is awestruck by the Great Room with 32 ft high ceilings and a stunning fieldstone fireplace. Could there be a more dramatic spot on Chappaquiddick to host a dinner party? All four of the bedrooms have bathrooms ensuite, and three of the bedrooms have water views. The details of the house are too many and varied to mention, and include the iron chandelier and sconces handmade by Vineyard artisan Barney Zeitz, glass prism set in the skylight roof, large reclaimed antique heart pine flooring throughout, atrium balcony, and two story screen porch. The landscape is equally captivating, with the softness of the many blooming flowers juxtaposed against the fieldstone walls. A lily pond allows visitors to visit and reflect. The property is virtually surrounded by conservation land and the abutting Pocha Pond Preserve offers 150 acres of trails and waterfront to enjoy. Views of Nantucket Sound are visible from the first and second floors and on a particularly clear day it is possible to see Nantucket itself. In addition to the 6500 sq ft of living space, there is a 2-car garage and large basement that includes an entertainment room, laundry room, a half bath, and large amounts of storage space

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 landscaped grounds with beautiful perennial gardens, 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. Excellent rental history.

Enjoy your entire summer poolside or at the beach. Welcome to this charming property near Long Point Wildlife Refuge and explore all it has to offer. You can walk, bike, or drive from the house to the beach, and spend the day body surfing in the ocean, splashing with the little ones in the ponds, or walking the grassland habitat. Afterward, take a refreshing dip in your 16 x 32 ft. in-ground swimming pool surrounded by a private, lush 1.7 acre sanctuary of gardens, grassy lawn, a wide variety of trees and perennials, and acres of conservation land beyond. Inside, three levels of living space provide you a versatile floor plan and room to spread out. Recent interior updates include a new library/office, kitchen appliances, quartz counters with tile backsplash, a vanity and tile in the bathrooms, and a full bedroom/bathroom/rec room suite in the basement. Updated electric. Also worth noting - a completely rebuilt brick chimney, flue, and propane fireplace, new entry doors and several windows, a new furnace, hot water heater, and a water softening system. Recent exterior updates include low-maintenance Hardie Board siding and Azek trim, asphalt roofing, a beautiful mahogany deck overlooking the lawn and pool, an outdoor shower, a built-in propane fire-pit for gathering on cool evenings, pool fence and filter, and an updated 6-bedroom septic system. Enjoy this home year-round or seasonally, or take advantage of the weekly income that 5 bedrooms and a pool bring. This is truly a superb value not to be missed!

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.

Never ending views, true relaxation, fishing, boating, beach life and nature are what this property has to offer. The panoramic views cover more than 180 degrees from Buzzard's Bay to Elizabeth Islands, and Vineyard Sound all the way to Martha's Vineyard. This year-round home has been expanded, updated, and lovingly cared for. All you need are your clothes, as the house is being sold fully furnished and thoroughly equipped. The living spaces are generous but comfortable. The house can live large or be very cozy. The deck provides incredible living area w/ample deck furniture. Look thru hydraulic binoculars and see birds on the beach, what fishermen are catching, and who is coming into the harbor. The galley kitchen is very efficient w/a expanded butler's pantry. 3 bedrooms upstairs have private decks and the primary bedroom has a designer bath. A wonderful wine cellar enhances the basement. A gem of a house waiting for its next steward.

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.

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and custom cabinetry. The five spacious bedrooms are thoughtfully positioned throughout the home, providing unparalleled privacy and comfort. The main house features four private bedrooms with three full bathrooms and private balconies. The fifth bedroom is housed over the detached two-car garage. The detached two-car garage not only provides ample storage for vehicles but also features a private one-bedroom suite above, perfect for accommodating guests or serving as a tranquil home office space. The meticulously landscaped grounds are a true masterpiece, featuring a sparkling pool surrounded by a flagstone patio complete with an outdoor dining area and fire pit, making indoor and outdoor living seamless. This property offers both tranquility and convenience. Just moments away from the charming shops and restaurants of downtown Edgartown, and a short distance from the island's pristine beaches. A well rounded offering that should not be overlooked!

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.

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The french doors open to a deck overlooking the manicured lawn. A state-of-the-art media room, complete with comfortable seating, a large screen, and high-quality audio visual equipment. It's the perfect spot for movie nights, game days, or simply relaxing with friends and family along with a wine cellar just steps away. The carriage house features a three-car garage, providing ample space for your vehicles and storage needs including a large one bedroom and bath upstairs. Katama Bay View Road is located adjacent to Sheriffs Meadow Conservation land and public access to Katama Bay. Conveniently located near South Beach, one of Martha's Vineyard's most beautiful and sought-after beaches.