MLS Number 42077

• Residential
• Mls Status Active
• Bedrooms 9
• Bathroom 7
• Acreage 0.833

The price above reflects the Reserve Price for the property, which is being marketed for sale by luxury private auction. Bidding is open through November 13. Seller reserves the right to accept or reject bids. 5% Buyer's Premium. Additional terms apply. Please visit Paramount Realty USA's website for more details. A landmark property located on the very northernmost tip of Martha's Vineyard. 1005 Main Street is one of the "Four Sisters" - the four grandest and most historic homes in the distinguished West Chop neighborhood. The setting is unparalleled with a large private beach and 210-degree views so expansive that you can enjoy both sunrises and sunsets from the same deck. The views are extremely dynamic with ferries and fishing boats passing in the distance, and at night, the twinkling of lights from the mainland. There are 9 bedrooms and 6 1/2 baths, which includes a 2-bedroom apartment in the lower level. The home still exudes olde worlde charm despite all 5,050 sq ft having been renovated between 1995 and 2022 with new insulation, roof, and HVAC system, and updated plumbing and electric. The 400 ft of private beach is a rare asset, and the boardwalk down to it has been trod by many who have come to love this home and incomparable setting. With its multiple decks and spectacular views, the home has always been a prime location for entertaining friends and family. Owners may inquire about membership at the nearby West Chop Club, which offers a wide range of amenities.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

MLS Number 42462

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 6.5
• Acreage 1.2

Welcome to your Vineyard Dream in the heart of West Chop! Built by Novo Builds, a renowned construction company that is recognized for their innovative designs and high-quality craftsmanship. Novo Builds is set to enhance the landscape of this iconic island with their latest development. This stunning new build offers the perfect blend of modern luxury and coastal charm, making it an ideal sanctuary for families or those looking to entertain in style. The home has 5 bedrooms, 6.5 bathrooms and 4,216 sqft. With a six bedroom septic in place, the new owner has the option of adding a bedroom. The open-concept design of the main living area ensures a seamless flow between the living room, dining area, and kitchen. High ceilings and large windows allow natural light to flood the space, creating a bright and airy atmosphere. The state-of-the-art kitchen is a chef's dream, featuring top-of-the-line appliances, custom cabinetry, and a large island perfect for meal prep and casual dining. Each of the five bedrooms is a private retreat, complete with en-suite bathrooms and ample closet space. The first floor master suite is particularly impressive, walk-in shower, dual vanities and master dressing room. The beautifully landscaped yard offers plenty of space for relaxation and recreation. Enjoy al fresco dining on the expansive patio or take a dip in the sparkling 18X40 pool. Complete with a cabana the yard is your personal retreat for relaxation and entertainment. Situated in West Chop, this home provides easy access to all that Martha's Vineyard has to offer, from pristine beaches, charming shops and fine dining. The estate is nestled near the prestigious West Chop Club, Vineyard Haven Yacht Club and Mink Meadows Golf Club. This new build in West Chop, to be completed summer 2025, is more than just a house; it's a lifestyle. Don't miss the chance to make this exquisite property your own and experience the best of Martha's Vineyard living. *Renderings are for illustrative purposes only. Architect plans and finish details available on request.

Listed by Joe Holland of Vineyard Dream Realty LLC

MLS Number 41504

• MultiFamily
• Mls Status Active
• Bedrooms 15
• Bathroom 12.5
• Acreage 0.84

A unique opportunity to own a one of a kind property with capacity for twenty people complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first level. The potential opportunity to subdivide this parcel only adds value to this well-rounded offering. The property is being offered turn key with the opportunity to own a very profitable business. This offering is for both the current business and the real estate. Just a short distance to downtown Vineyard Haven, the harbor and the ferry, look no further for your future investment!

Listed by Madelyn Silvia of Wallace & Co. Sotheby's

MLS Number 41384

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 4
• Acreage 8.21

A combination of luxury, comfort, and natural beauty, this expansive custom, five bedroom, post and beam home is sited on more than eight acres of land, surrounded by acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow from one room to the next, perfect for entertaining or simply enjoying daily living. The great room features a beautiful custom Johnny Hoy stone fireplace, cypress ceiling, white ash flooring, and custom cabinetry. High end chef's kitchen with breakfast bar opens into the dining area. Home has state of the art technology, solar panels, and an elevator. From the screened porch, with a second custom fireplace by Johnny Hoy, to the expansive finished basement with media room, this home invites you to enjoy many amazing spaces. Main floor offers the open living concept as well as a separate den, two offices, and two bedrooms, including the primary bedroom suite with office and bathroom. Single story living as well as handicapped accessibility and generational living is possible with this floor plan. In addition to the media and rec room, the lower level has ground floor living space as well as two additional bedrooms, one full baths and a 1/2 bath in the theater room. The beautiful, professionally landscaped yard leads you to a two story post and beam 48x52 barn. Every detail of this home has been carefully designed to exceed your expectations. Impeccable craftsmanship elevate this home to a level of luxury that is unmatched. Don't miss out on the opportunity to make this dream home your home.

Listed by Sheila Morse of Island Real Estate

MLS Number 42618

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.8948

NOW INCLUDING RARE 12,527 S.F. TOWN APPROVED BUILDING LOT ON WILLIAM STREET! Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House*, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District, just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. For 35 years, home of Susan Branch, the illustrious self-taught artist and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,300 s.f. of living space on .92 acre in-town with wood floors throughout and cheerful morning and afternoon sunlight. With period paneling, crown molding, and 9' ceilings, the floor plan includes a welcoming front hall entry with lovely curved staircase, front parlor, formal living room with fireplace and bay window, spacious dining room, second side entrance vestibule used as a dry bar, cozy wood paneled study/tv room, eat-in kitchen with wainscotting, east-facing side porch, laundry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor includes additional spacious rooms: A large primary bedroom with fireplace, double closets and ensuite bath, sitting room, three additional bedrooms, two with double closets, one with bay window, plus two additional full baths. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has plans for potential renovation of the barn to include a studio apartment - see Documents. Mature plantings including privet, flowering trees and bushes, perennials, historic Linden trees, and herb garden. Six (6) bedroom approved Title 5 septic. A rare opportunity for those who appreciate the history and value of historic homes in a sailing port which as been described as "the sweetest little harbor on the east coast." Extensive list of furnishings and household items available for purchase by separate bill of sale. Property is also available for purchase at $2,850,000 without the approved 12,526 s.f. buildable lot

Listed by June Flake c. 508.294.8098 of Viewpoints

MLS Number 42030

• CommercialSale
• Mls Status Active
• Bathroom 1.5
• Half Baths 1
• Acreage 0.2734

7500 sq ft+ commercial office building in the Waterfront/Commercial District of Vineyard Haven. There are currently 10 rented office spaces with several long-term tenants in place who enjoy the building's excellent condition and waterfront location with stunning views over both the Harbor and Lagoon. Located less than half a mile to the ferry and downtown Vineyard Haven. Financials are available with a signed NDA. Note: Monthly fees for each unit are calculated based on the square footage of that unit. Showings on Sunday only and with minimum 48 hour notice.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

MLS Number 42136

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 0.2183

This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven’s most quiet and quaint neighborhoods. With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also features a renovated garage with a finished second level, perfect for a creative studio. Inside, the home exudes warmth and elegance, with wide pine flooring, custom craftsmanship, and intricate wood detailing on the ceilings. The spacious living room, centered around a gas fireplace, is both inviting and stylish. The sunlit kitchen, equipped with top-of-the-line appliances and refined finishes, includes a cozy window seat that adds to its charm. The primary bedroom suite offers a serene retreat, complete with a private tile bath and access to a 2nd-floor deck. The three additional bedrooms are equally comfortable and well-appointed, providing ample space for guests. The finished lower level expands your living space further, ideal for a home theater, gym, or playroom. Spend your days soaking in this privacy that this tranquil abode provides, or take advantage of its ideal location to access the hustle and bustle of downtown Vineyard Haven where you can enjoy various galleries, shops, and fine dining. This location is also convenient to Owen Park Beach, West Chop and Mink Meadows Golf Club.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

MLS Number 41839

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 4.5
• Acreage 0.38

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.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

MLS Number 42076

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 4
• Acreage 3.21

Welcome to your dream home in the exclusive 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, ideal for both entertaining and everyday living, 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 bedroom suite is beautifully appointed and features a spacious bathroom with double sinks, spa tub and shower. The bedrooms are generously sized, with ample natural light and stunning views of the surrounding landscape. The third level holds tremendous potential, offering the possibility to add 2 additional bedrooms, further enhancing the home's versatility. Outside, the back deck and expansive grounds provide a peaceful sanctuary, perfect for outdoor activities, gardening, or simply relaxing in nature's embrace. As a resident of the Lower Makonikey Association, you'll enjoy access to a private association beach on Vineyard Sound. This exceptional property is more than just a home; it's a lifestyle. Experience the perfect blend of privacy, elegance, and community in one of Martha's Vineyard's most sought-after neighborhoods.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

MLS Number 42020

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.6072

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable lot. For 35 years, home of Susan Branch, the illustrious self-taught artist and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,300 s.f. of living space on more than a half acre in town with wood floors throughout and day long, east to west sunlight. With period paneling, crown molding, and 9' ceilings, the floor plan includes front hall entry with lovely curved staircase, front parlor-studio, formal living room with fireplace and bay window, spacious dining room, second side entrance vestibule used as a dry bar, cozy wood paneled study/tv room, eat-in kitchen with wainscotting, east-facing side porch, laundry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor includes additional spacious rooms: A large primary bedroom with fireplace and ensuite bath, sitting room, three additional bedrooms, one with bay window, plus two additional full baths. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining. Seller has plans for potential renovation of the barn to include a studio apartment - see Documents. Mature plantings including privet, flowering trees and bushes, perennials, historic Linden trees, and herb garden. Six bedroom approved Title 5 septic. A rare opportunity for those who appreciate the history and value of historic homes in a sailing port which as been described as "the sweetest little harbor on the east coast." *Extensive list of furnishings and household items available for purchase by separate bill of sale. This property and the owners abutting Town Approved Building Lot comprised of 12,527 s.f on William Street is available for purchase together for $3,800,000.

Listed by June Flake c. 508.294.8098 of Viewpoints

MLS Number 42345

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 0.179

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 laundry. Every detail of this home has been thoughtfully considered, including a charming compass rose stained glass window, adding a touch of nautical flair. The finished lower level includes additional living space and a spacious bedroom. Step outside to the stunning mahogany rear deck overlooking a newly landscaped yard, ideal for entertaining and an outdoor shower. With easy access to Downtown Vineyard Haven and Vineyard Sound beaches, don’t miss the opportunity to own this exceptional property where timeless beauty meets contemporary living.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's