$3M - $5M

MLS Number 41843

• Residential
• Mls Status Active
• Bedrooms 8
• Bathroom 6.5
• Acreage 4.6

Picturesquely sited on a spacious 4.6-acre parcel, this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach, hiking trails, Up-Island Cronig’s, and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels, each area provides spacious yet private surroundings. The main living area features a dramatic great room with a vaulted ceiling. The chef’s kitchen with an adjoining pantry opens to the spacious dining room with access to a side deck. An ensuite bedroom, half bath, and laundry/mudroom complete this floor. The upper level is dedicated to the primary ensuite with a walk-in closet and a three-bedroom guest wing with a private den and full bath. You will be pleasantly surprised with the additional 2100 sf lower level, designed for fun and recreation. The spacious game room is perfect for entertaining, watching sports on TV, playing billiards or ping pong, or simply relaxing at the delightfully designed bar with oak barrel barstools. Two additional bedrooms on the lower level provide a more private space for guests and visitors with two exquisitely appointed bathrooms and six custom-built adult-size bunk beds. The library is truly one-of-a-kind with built-in floor-to-ceiling bookshelves and a moveable ladder for easy access to all your literary treasures. The library also boasts an 81” TV that can be hidden away behind custom cabinets when entertainment calls for a more formal ambiance. A Sonos Sound System was installed throughout the house, ensuring you can always listen to your favorite tunes. There is so much to enjoy here, indoors and out, and creating this stunning Vineyard Farmhouse Estate has truly been a passion of love. The two-story guest house with a new deck that overlooks the Egyptian Lotus Pond, has an unfinished interior awaiting your vision. Completing this fabulous unique offering is a large two-story post and beam barn built in 2014. In the words of the owners: “It is as if your body can breathe here, and you can pause and simply be. What a gift. It is just the right balance of being and doing.” With the appropriate special permitting, there is a potential to run a business out of the barn or the guest house.

Listed by Donnelly + Co

MLS Number 42160

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 4.56

NEW BRIGHT & AIRY CONTEMPORARY OFF SOUTH ROAD! The house newly completed in 2023 & the one car garage in 2024 are nicely situated on a 4.56 acre lot. The 4 bedroom residence offers 3500 sf of finished living on two levels. On the first level are 2 primary bedrooms, each with en suite bathrooms, and a spacious open floor plan for living, dining and kitchen. An office off the kitchen allows you to work from home. Step out from the living room to a covered porch, deck and outdoor shower. Off the main floor an open stairway leads to the lower level with 2 large bedrooms with full size windows and access to a partially covered patio. A large double section bath is shared by both bedrooms. Perfectly located a short distance off South Road the property offers easy access to both down island and up island.

Listed by Kendall & Kendall

MLS Number 40933

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 5.5
• Acreage 1.0102

EDGARTOWN - NEW CONSTRUCTION with POOL - 6 Bedrooms...in Two Structures.....Plus a 31'6" x 14' heated saltwater pool! 5 Bedroom Main House with 4.5 Bathrooms. Detached 1 bedroom w/Full Bathroom over a Two (2) car garage. Main house has a lovely open floor plan with a large kitchen w/Bosch® Stainless Steel Appliances, beautiful Soapstone Island and Carrara Marble counters, a dining room, additional breakfast area and a living room w/fireplace flanked by built in shelves. Living area leads through French Doors to a large mahogany deck, that continues the length of the rear of the house and incorporates a private deck outside the ground floor private suite! Step off the deck directly onto the patio surrounding the saltwater pool and custom outdoor wood burning Fireplace! Lovely hardscape and dramatic landscaping. Back inside, Four more bedrooms upstairs, two (2) are private suites, plus two (2) guest rooms that share a full bathroom. DETACHED BEDROOM: 368 sq.ft. One bedroom with a FULL PRIVATE BATH, which is the Sixth (6th) Bedroom and Fourth (4th) Suite, a 'getaway space', over a two car Garage. Garage has potential for future expansion into a self contained guest house with approvals from the ZBA. Minutes to Farm Neck Sanctuary, short distance to Sengekontacket Pond and Downtown Edgartown, quick trip to Farm Neck Golf or Edgartown Golf. DAYS ON MARKET INCLUDE BUILDING PERIOD.

Listed by Alisan Lohan-Conway Properties

MLS Number 42053

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 3.5
• Acreage 1.23

Located in picturesque Sweetened Water Farm on a 1.2-acre lot, lies this 3,400 square foot 5-bedroom, 3.5-bath traditional styled home. The primary entrance leads through a large eat-in kitchen to a dramatic 2-story cathedral ceiling Great room with a large stone fireplace at each end. There is a first-floor master suite and 4-bedrooms upstairs sharing 2 baths. The entrance road leads past rolling pastures and a beautiful horse barn and winds up through a wildflower filled field to the house. There is a large lawn and the property has mature landscaping creating a wonderful setting. A unique opportunity which offers a English country feeling while located less than a mile to Edgartown’s village center.

Listed by Landvest MV

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 Wallace & Co. Sotheby's

MLS Number 41412

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 2.5
• Acreage 0.25

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

Listed by Landvest MV

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 Wallace & Co. Sotheby's

MLS Number 41970

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.53

Welcome to this oversized cape style home that offers numerous gathering spaces for multi-generational living. The first floor offers an open kitchen/dining floor plan that flows seamlessly into the cathedral ceiling family room which showcases a fireplace surrounded by stone. An additional first floor living room offers two separate seating areas running from the front to the rear of the home. Both first floor living rooms sport french doors that lead to an inviting outdoor living space of decking, patio, garden views and an outdoor shower. There is a first floor and second floor primary suite. The home also features two additional guest bedrooms, with the capacity to expand with up to seven bedrooms because the property is on town sewer. The first floor primary en suite has a soaring cathedral ceiling and french doors doors that lead to the expansive outdoor lounge area. A lower level partially finished basement area offers two finished lounge areas, a laundry room and a large unfinished area for extra storage. Careful attention has been paid to the exterior plantings with texture, color and blooming times all taken into consideration. This home has thoughtful details both inside and out. It is a “must see” to appreciate all it offers. Last, but not least is it’s key location. The property is in close proximity to Morning Glory Farm, Edgartown Village and South Beach.

Listed by Vineyard Village Realty

MLS Number 42020

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3.5
• Acreage 0.55

Fairy tale setting in the quaint seaside village of Vineyard Haven, aka Holmes Hole in the day, 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. 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.

Listed by Viewpoints

MLS Number 42026

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 3
• Acreage 0.13

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.

Listed by Wallace & Co. Sotheby's