4 Bedroom homes for sale & real estate in Dukes County, MA

4 Bedroom Homes for Sale in Dukes County, MA

Find yourself at home in Chilmark with this inviting multi-unit property! Set conveniently on a quiet lot just moments from Chilmark General Store, Squibnocket, Menemsha, and Lucy Vincent Beach, this property has been thoughtfully upgraded for year round use by the current owners with new metal roof, shingles/siding, solar, mini-split AC, and more. The layout of the home includes a three bedroom dwelling on the main level that opens out to a sunny and private backyard. The walkout apartment was recently gut-renovated, features one bedroom plus office/den, and is accessed privately on the opposite side of the house. Both dwellings feature full kitchens and their own laundry. With a superb Ch

4 Bedroom Homes for Sale in Dukes County, MA

Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors lead to a large deck, perfect for outdoor entertaining. The open kitchen and dining room are at the back of the house and enjoy direct deck access. There is a half bath off the living room. The primary suite with a full bath, and 2 additional bedrooms that share a full bath, complete the second floor.

4 Bedroom Homes for Sale in Dukes County, MA

Welcome to a modern oasis nestled in the lovely community of Tower Ridge. This exquisite residence offers generous living space, perfectly designed for comfort and style. Step inside to discover a beautifully renovated kitchen, featuring sleek finishes and modern appliances, ideal for culinary enthusiasts. The open floor plan seamlessly connects indoor and outdoor living, providing ample space for both relaxation and entertainment. The home boasts a huge primary bedroom, offering a serene retreat with ample natural light and luxurious finishes. The additional bedrooms are spacious, providing versatility for guests or a home office. 5 bedroom septic system offers expansion possibilities. Sit

4 Bedroom Homes for Sale in Dukes County, MA

With easy access to the West Tisbury Village, this lovely 4 bedroom, 3.5 bath home is privately sited on 1.4 acres overlooking a protected pasture. Many nice features include open living spaces, a well equipped kitchen with stainless steel appliances, a center island and granite. The sun-filled great room with oversized windows offer peaceful views of the meadow, a cathedral ceiling and sliders to a wrap around deck for outdoor entertaining and enjoyment. The dining room features a butlers pantry, comfortable living room with many custom built-in shelving, fireplace and sliders to another spacious deck There is a first floor primary with en-suite bathroom and walk-in closet. Some of the man

4 Bedroom Homes for Sale in Dukes County, MA

These twin houses built in 1909 in the historic subdivision of East Chop Highlands offer most of the modern conveniences of today with the old world charm and decorative craftmanship style. Both houses are separately deeded so that they could be owned separately or together. These houses are fully winterized and have been occupied for the past 30 years. Each house has 2 bedrooms with bathrooms en suite. An open floor plan with a kitchen, dining area, and living room #12 has a bonus room presently used as an office. Both houses have 2 heating systems, both forced hot-air central heat, and air pump heating and air conditioning for energy efficiency. One is heated with oil and the other with p

4 Bedroom Homes for Sale in Dukes County, MA

Experience the serene beauty of this 4-bedroom, 3.5-bathroom pond-front home in the Sengekontacket Community. Nestled on a hillside overlooking a freshwater pond, this home offers the perfect island retreat. Lush garden beds and wildflowers greet you as you make your way to the pond, where you can enjoy swimming or paddling. The well-appointed kitchen seamlessly connects to the dining room and deck, all with stunning pond views. The first-floor primary bedroom features a private bath and a spacious closet, with sliding doors to the back deck. Upstairs, another ensuite bedroom awaits, along with an open loft ideal for an office or a game room. The finished lower level opens to a bluestone pa

4 Bedroom Homes for Sale in Dukes County, MA

Rare Opportunity: Water View Retreat In Down Harbor With Private Beach, Dock And Mooring Access – Seize the opportunity to own one of the few water view properties in the prestigious Down Harbor neighborhood -- a true gem for boaters and beach enthusiasts as residents enjoy exclusive deeded access to a sandy association beach, plus the opportunity to keep a boat or dinghy on the association dock or in the mooring field on Katama Bay. This unique distinction makes Down Harbor one of the most coveted neighborhoods on the island and one that is undergoing significant change. The home has been beautifully updated in 2022and features an open-designed and sunny Living/Dining Room and Kitche

4 Bedroom Homes for Sale in Dukes County, MA

Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf range, and wine cooler. There is a casual dining area off the kitchen and a formal dining room. The spacious first floor primary bedroom has a large walk-in closet, soaking tub, and bay window looking to the backyard. The other bedroom is currently being used as a TV room. The second level has two

4 Bedroom Homes for Sale in Dukes County, MA

Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This main house and guest house are perfectly sited on just over 2 acres and are ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. Guest house needs finishing and presents a number of possibilities. Both structures are sited with the potential to expand, and according to the West Tisbury Board of Health, the property can support up to 8 bedrooms. This property is being sold "as-is".

4 Bedroom Homes for Sale in Dukes County, MA

This 4-bedroom home is located within the desirable Hidden Cove Association, a 65-acre community of well-tended homes with direct water access to Sengekontacket Pond, State Beach, and Nantucket Sound. The property has conservation land behind and beside it. You truly feel like you are on the Vineyard when you make your way down the boardwalk through the marsh to the secluded area with private boat dockage and a place to keep your kayaks and other watercraft. There are also walking trails and tennis. All this is within the outskirts of Oak Bluffs with easy access to other towns. Hidden Cove is a well-maintained community of active neighbors as evidenced by their website at https://hiddencove

4 Bedroom Homes for Sale in Dukes County, MA

Long Point Beach Retreat - Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both levels of the home, creating unique spaces for outdoor relaxation and enjoyment. The property showcases an abundance of recent upgrades, including a newly renovated gourmet Cook's Kitchen with stunning quartz countertops and brand new GE® stainless appliances throughout. Additionally, all bathrooms h

4 Bedroom Homes for Sale in Dukes County, MA

A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and a kitchen with doors leading out to a welcoming screened porch. This home features a primary bedroom suite and a guest bedroom suite on the first level. Two additional guest bedrooms complete second floor. The exclusive Boldwater Association offers tennis courts, a boat landing on the Edgartown Grea

4 Bedroom Homes for Sale in Dukes County, MA

Discover Edgartown's Best Kept Secret - Bold Meadow. Move right in and enjoy the Vineyard lifestyle in a spacious 3 bedroom, 2 and a half bath home with a beautiful first floor primary suite with walk-in closet and spa bath, a spacious open floor plan and extensive deck designed for outdoor living. All just minutes to West Tisbury and Edgartown Village centers, the MV airport with convenient shopping, island-wide bike paths and South Shore beaches. Oak floors, cathedral ceilings, and extensive skylights create a sun filled interior, the second floor features a guest bedroom and a two-room bedroom suite with shared tile bath. Set on a beautifully landscaped . 8-acre property with curving pea

4 Bedroom Homes for Sale in Dukes County, MA

CHARMING VINTAGE HOME IN THE HEART OF EDGARTOWN VILLAGE. Nestled within lush perennial gardens and surrounded by hedges and a classic picket fence, the Charles W. Crowell House is a delightful antique home that captures the essence of a bygone era. With its origins dating back to 1760, the home boasts beams crafted from trees that once grew on the property. These timeless timbers are prominently showcased throughout the home, adorning the ceilings and walls with their enduring presence. Renovated in 2010 to incorporate modern conveniences such as updated electrical, central air conditioning and refreshed kitchen and baths, the residence has seamlessly blended contemporary comfort with its o

4 Bedroom Homes for Sale in Dukes County, MA

This meticulously renovated 1920s gem is nestled in the desirable West Chop area of Vineyard Haven, offering a perfect blend of historical charm and modern luxury. With access to a pristine beach on Vineyard Sound, this exquisite residence is a seaside haven. Step inside to discover a spacious layout. The heart of the home is the gourmet kitchen, boasting custom cabinetry and high-end appliances. Entertain with ease in the open-concept living and dining areas, where upgraded systems and central A/C ensure year-round comfort. The second floor features a primary bedroom suite with a luxurious tile bath and soaking tub in addition to 2 guest bedrooms and an elegantly appointed guest bath with

4 Bedroom Homes for Sale in Dukes County, MA

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

4 Bedroom Homes for Sale in Dukes County, MA

WHAT'S SPECIAL - A MOVE-IN READY, FULLY RENOVATED COMPOUND IN KATAMA WITH AN INDOOR POOL AND HIGH-TECH ENTERTAINMENT: Do you want to hone your swimming skills and train in an indoor Endless Pool, like the ones used to train athletes at Harvard University, USC and many other universities? Do you want your kids or grandchildren to be able to play and swim in an in-door pool on rainy or foggy days in the summer, on colder days in June and September or at family gatherings for Thanksgiving or Christmas? Do you want to tour world cities, hike the Alps, train for a Marathon or simply walk down any street in the world on Google Maps on a Nordictrack Commercial 32i treadmill, with its 32'' screen a

4 Bedroom Homes for Sale in Dukes County, MA

Enjoy the convenience of Dark Woods, a quiet neighborhood in an ideal location close to the Village, bike path, beaches, and 27 acres of Sheriff’s Meadow conservation land. Tucked in the woods of the pleasant Dark Woods community, this property has been meticulously maintained and is ready for your enjoyment. The first floor features a fabulous living room with a gas fireplace and a formal dining room. Overlooking a private backyard is the open eat-in kitchen with direct access to a 2-tiered deck. A bar/pantry is conveniently located between the dining room and kitchen, and bonus space above the 2-car garage. The primary ensuite with a renovated bathroom is on the right and 2 large gu

4 Bedroom Homes for Sale in Dukes County, MA

EDGARTOWN - NEW BUILD - Exceptionally stylish, wonderful curb appeal! Luxurious 4 bed, 6 bath home, timeless features, black windows, complimented by elegant neutral decor, peppered w/ lovely details throughout. Abuts 32 acres Common land & 5,300 acres State Forest. Numerous entertaining areas, indoors & out. An entertainer's dream. Open floor plan - Living room, w/ fireplace, breakfast area, custom kitchen, huge island. Mahogany deck, w/ pergola overlooking yard & pool. Ground Floor Bed w/ private bath. 1st floor laundry. Powder room. UP: 2 more suites w/ private baths. 2nd laundry. 4th bedroom. 4th full bath. Large loft. Breezeway connects house to garage, leads to pool

4 Bedroom Homes for Sale in Dukes County, MA

Located in Lower Makonikey Association, a serene enclave on Martha's Vineyard. This meticulously crafted 3,284 square-foot residence with a 3-car garage is a masterpiece of design and comfort, set on 3.21 acres of lush, tree-lined grounds accented by historic stone walls. Offering 4 spacious bedrooms and 4 elegantly appointed bathrooms, this home embraces the charm of island living. The main level features a flowing floor plan with a gourmet kitchen with a sun-filled breakfast nook, and butler's pantry, dining room, and a spacious living room with a brick fireplace. A home office and laundry room finish the first floor which has beautiful hardwood floors throughout. Upstairs, the primary be

4 Bedroom Homes for Sale in Dukes County, MA

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 f

4 Bedroom Homes for Sale in Dukes County, MA

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 Westminster 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, comp

4 Bedroom Homes for Sale in Dukes County, MA

Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space. The main level boasts a thoughtfully designed floor plan featuring a gourmet kitchen, a spacious living area, and a dining space ideal for entertaining. The primary bedroom suite offers a private retreat with a luxurious en-suite bathroom. With a 6-bedroom septic in place, the possibilities for expansion are endless. The generous lot size allows for the pote

4 Bedroom Homes for Sale in Dukes County, MA

Welcome to this beautiful in-town oasis! With a brand new gunite pool with integrated spa, this charming four bedroom home shines in downtown Edgartown. Perfect for a variety of buyers with an established rental history (summertime rate consistently at $20,000/week), this home is a fabulous gathering place and a true gem. The first floor is exceptionally sunny and open, with a high-ceilinged foyer and bright wood floors. There is a primary suite on the first floor and two large bedroom suites on the second floor. The lower level is also finished with a fourth bedroom and bathroom. The pool was completed in 2022 by Easton Pools, with elegant bluestone and landscape creating the perfect summe

4 Bedroom Homes for Sale in Dukes County, MA

Located in the Dodger's Hole subdivision is this inviting four-bedroom two-bathroom cape style home. The property has been well-cared for and is a delight to view. Sited on . 5 acres of land with a pea stone driveway, wraparound deck and outdoor shower with new enclosure. The antique garage is great for storage or a small vehicle. The living room is open to the tiled eat-in kitchen area and hallway leads to a pantry, full bathroom and two first floor bedrooms. Second floor offers a full bathroom and two generous sized bedrooms. Entire interior of the home was painted in October 2024 including; windows, doors, walls, ceilings, baseboard electric, and all interior trim. Vacant and easy to sho

4 Bedroom Homes for Sale in Dukes County, MA

Imagine enjoying your morning routine on the oversized porch, overlooking Seth's Pond. The layout is designed for both privacy and togetherness, with a welcoming living room and dining area. Immerse yourself in the beauty of the outdoors. The spacious yard offers room for play and relaxation, and the pond beckons with opportunities for swimming, kayaking, and more. The location, off of Lambert's Cove Road affords access to Lambert's Cove beach and Long Point Beach - with a beach pass. The property has been in the same family since 1968. Embrace the chance to breathe new life into a cherished family treasure and turn it into your ultimate Martha's Vineyard escape. Changes to the footprint of

4 Bedroom Homes for Sale in Dukes County, MA

Seize the chance to possess a truly extraordinary, highly esteemed, and unparalleled property on the East Coast! Edgartown, known for its rich history, nautical charm, and scenic beauty is home to this remarkable property being offered for the first time in over 30 years! Sited at the center of the harbor sits this rare offering featuring a beautifully appointed three-story residence with fabulous views, a two-story clubhouse on the harbor and more than 500 feet of deep-water dockage, capable of accommodating up to ten vessels, including superyachts. The waterfront clubhouse is ideal for entertaining guests at the harbor’s edge. Utilize the docks for your own private fleet of boats, p

4 Bedroom Homes for Sale in Dukes County, MA

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

4 Bedroom Homes for Sale in Dukes County, MA

43 Peases Point Way South is where warmth and style meet sophistication, creating a truly one-of-a-kind living experience in the heart of Edgartown Village. Once you step through the gated arbor, you are welcomed by a lovely courtyard, creating the first of many unexpected and special moments carefully planned to provide the utmost privacy and tranquility, whether indoors or out. The Patrick Ahearn-designed home, just a short stroll away from Main Street shops, restaurants and the scenic Edgartown harbor, is elevated by its exceptional interior finishes and distinctive floor plan. Unparalleled luxury is carried through all levels of living, including an awe-inspiring outdoor space anchored

4 Bedroom Homes for Sale in Dukes County, MA

A gorgeous oversized in-town . 6-acre lot with a picturesque view of the gardens, pine woods, and wetlands that extend to Sunset Lake and Oak Bluffs harbor. This excellent location is served by town water and the town sewer system. A short distance to Oak Bluffs harbor, ferries, and all that Oak Bluffs has to offer including restaurants, entertainment, and sandy beaches - yet a quiet oasis apart from the activity. Down the street from the new Oak Bluffs Town Hall and the Library. The original house is still on the property, but demolition approval is in place (see Documents). The listing includes all approvals and plans for a stunning 2,500 square foot home designed by Breese Architects. Th