5-Bedroom Homes for Sale in Marthas Vineyard, MA

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  /45

  $19,500,000

  • 7 Beds
  • 6 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
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  /39

  $3,649,000

  • 5 Beds
  • 4.5 Baths
  • 4,218 Sq Ft

  7 Whistling Swan Cir, Edgartown, MA 02539

  Located in the sought-after Island Grove neighborhood, this Edgartown home is near Morning Glory Farm, Downtown, and South Beach. Designed for entertaining, the first floor features a custom kitchen, dining and living rooms, den, screened porch, half bath, and a seamless flow to outdoor living and a new heated pool. A spacious first-floor primary suite includes a walk-in closet and full bath.

  Jarrett Hurwitz Keller Williams Realty

  7 Whistling Swan Cir, Edgartown, MA 02539
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  /44

  $2,748,000

  • 6 Beds
  • 4 Baths
  • 2,400 Sq Ft

  111 Eastville Ave, Oak Bluffs, MA 02557

  JUST REDUCED!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

  Ed Charter Arrowhead Homes

  111 Eastville Ave, Oak Bluffs, MA 02557
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  /51

  $4,950,000

  • 5 Beds
  • 4 Baths
  • 4,044 Sq Ft

  49 Gosnold's Way, Chilmark, MA 02535

  Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

  Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
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  /37

  $2,725,000 Open Thu 10:30AM - 12:30PM

  • 5 Beds
  • 4.5 Baths
  • 4,982 Sq Ft

  79 David Ave, Vineyard Haven, MA 02568

  BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

  Tina Miller Compass

  79 David Ave, Vineyard Haven, MA 02568
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  /42

  $7,450,000

  • 5 Beds
  • 3 Baths
  • 2,269 Sq Ft

  34 Edys Island Way, Chilmark, MA 02535

  Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

  Jill Napior Tea Lane Associates

  34 Edys Island Way, Chilmark, MA 02535
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  /37

  $4,850,000

  • 5 Beds
  • 3 Baths
  • 3,440 Sq Ft

  146 Quansoo Rd, Chilmark, MA 02535

  Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

  Meg Bodnar Tea Lane Associates

  146 Quansoo Rd, Chilmark, MA 02535
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  /60

  $14,000,000

  • 6 Beds
  • 7 Baths
  • 6,967 Sq Ft

  8 Snail Rd, Chilmark, MA 02535

  This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

  Alyssa Halisky Wallace & Co. Sotheby's

  8 Snail Rd, Chilmark, MA 02535
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  /75

  $19,900,000

  • 5 Beds
  • 7 Baths
  • 6,577 Sq Ft

  33 Boldwater Rd, Edgartown, MA 02539

  Exquisite Waterfront Retreat - A rare opportunity to purchase a meticulously crafted 5,600 square-foot stone main house and 900 square-foot stone guesthouse with pool in a naturalized wooded setting. This extraordinary compound redefines the conventions of traditional Vineyard architecture in the most charming and sophisticated of ways. The house was sited to offer views of Edgartown Great Pond

  Deb Hancock Hancock Real Estate

  33 Boldwater Rd, Edgartown, MA 02539
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  /39

  $10,500,000

  • 8 Beds
  • 6 Baths
  • 3,888 Sq Ft

  47 E Chop Dr, Oak Bluffs, MA 02568

  East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr, Oak Bluffs, MA 02568
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  /46

  $14,500,000

  • 8 Beds
  • 8 Baths
  • 8,912 Sq Ft

  30 Crackatuxet Cove Rd, Edgartown, MA 02539

  This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive

  Gerrett Conover Landvest MV

  30 Crackatuxet Cove Rd, Edgartown, MA 02539
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  /30

  $7,450,000

  • 5 Beds
  • 7 Baths
  • 5,454 Sq Ft

  54 Fuller St, Edgartown, MA 02539

  This stately Greek Revival home lies on beautiful Fuller Street and a short walk to the beach. This 5-bedroom / 5.5-bath home features a beautiful foyer with arches and paneling leading past a grand staircase to a beautiful family room, kitchen and screened porch overlooking the backyard. There is an ensuite ground first floor bedroom and office off the hall as well as a side mudroom entry and

  Gerrett Conover Landvest MV

  54 Fuller St, Edgartown, MA 02539
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  /37

  $3,300,000

  • 5 Beds
  • 4.5 Baths
  • 4,115 Sq Ft

  357 W Tisbury Rd, Edgartown, MA 02539

  Here is the Edgartown compound you've been waiting for - a 5-bedroom main house, 2-bedroom guest house, and elevated swimming pool area located on 1.5 acres. Next door there is 25 acres of conservation land. The property is barely 2/10s of a mile to Morning Glory Farm, and just a mile and a half to the village on the bike path. The house combines island country charm with modern amenities - honey

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  357 W Tisbury Rd, Edgartown, MA 02539
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  /40

  $7,500,000

  • 6 Beds
  • 7 Baths
  • 5,166 Sq Ft

  74 Turkeyland Cove Rd, Edgartown, MA 02539

  This distinguished Edgartown Great Pond compound presents an exceptional collection of features and amenities. Situated within a highly desirable, secluded enclave on Turkeyland Cove, the 4.8-acre property includes two residences, a bespoke private in-ground swimming pool, approximately 400 feet of waterfront, outstanding water views, and a private beach lot on the Atlantic Ocean. The principal

  Peyton Wallace Studio Realty

  74 Turkeyland Cove Rd, Edgartown, MA 02539
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  /42

  $3,195,000

  • 5 Beds
  • 4 Baths
  • 2,300 Sq Ft

  27 Spring St, Vineyard Haven, MA 02568

  Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features five fireplaces, (one currently hidden behind a plastered wall), a gracious living room, dining room,

  Alexis Holden Tea Lane Associates

  27 Spring St, Vineyard Haven, MA 02568
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  /41

  $1,650,000

  • 5 Beds
  • 3.5 Baths
  • 4,032 Sq Ft

  36 Ferro Way, Tisbury, MA 02568

  36 Ferro Way, Vineyard Haven – A Stunning Colonial on Martha’s VineyardWelcome to 36 Ferro Way, a beautifully crafted Colonial-style home nestled in the heart of world-famous Martha’s Vineyard. This exceptional five-bedroom, three-and-a-half-bathroom residence boasts an expansive floor plan, abundant natural light, and a charming farmer’s porch that warmly invites you inside.Step into the heart

  Michael Harney Sotheby's International Realty

  36 Ferro Way, Tisbury, MA 02568
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  /47

  $9,995,000

  • 8 Beds
  • 12 Baths
  • 7,585 Sq Ft

  12 Boldwater Rd, Edgartown, MA 02539

  Uncover unparalleled Martha’s Vineyard opulence within a sprawling 9.8-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

  Jarrett Hurwitz Keller Williams Realty

  12 Boldwater Rd, Edgartown, MA 02539
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  /32

  $2,495,000

  • 5 Beds
  • 3.5 Baths
  • 2,685 Sq Ft

  35 Woody Bottom Rd, West Tisbury, MA 02575

  This Cape style 5 bed/ 3.5 bath home is located in a nice area privately sited on 3 acres. This home features a nice floor plan thatincludes a fully equipped kitchen with center island, custom cabinetry and granite counters. Just off the kitchen is a sunny breakfastroom, a separate dining room, a spacious living room with fireplace and 2 sets of sliders to a backyard deck. There is a cozy

  Brenda Galligan Karen M. Overtoom R.E.

  35 Woody Bottom Rd, West Tisbury, MA 02575
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  /39

  $1,895,000

  • 5 Beds
  • 3 Baths
  • 2,432 Sq Ft

  32 Flamingo Dr, Edgartown, MA 02539

  This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

  Skip Dostal, Jr Martha's Vineyard Real Estate

  32 Flamingo Dr, Edgartown, MA 02539
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  /44

  $8,995,000

  • 5 Beds
  • 7 Baths
  • 3,762 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /32

  $2,999,000

  • 8 Beds
  • 7.5 Baths
  • 3,770 Sq Ft

  72 Chappaquiddick Ave, Edgartown, MA 02539

  WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS COURT that doubles into TWO PICKLE BALL COURTS, and a BASKETBALL

  Michele Casavant Vineyard Village Realty

  72 Chappaquiddick Ave, Edgartown, MA 02539
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  /42

  $19,900,000

  • 8 Beds
  • 7.5 Baths
  • 6,041 Sq Ft

  114 N Water St, Edgartown, MA 02539

  The property is currently rented; showings require a minimum of 48 hours’ notice. Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living

  Erin Hegarty Compass

  114 N Water St, Edgartown, MA 02539
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  /29

  $2,700,000

  • 6 Beds
  • 4 Baths
  • 1,616 Sq Ft

  34 Massasoit Ave, Oak Bluffs, MA 02568

  Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to

  Carleen Cordwell Anchor Realty of Martha's Vineyard

  34 Massasoit Ave, Oak Bluffs, MA 02568
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  /46

  $7,795,000

  • 7 Beds
  • 6 Baths
  • 6,921 Sq Ft

  19 Locust Ln, Aquinnah, MA 02535

  This beautifully designed and built home is privately sited on 12.23 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone fireplace and concrete floors heated by radiant heat. French doors

  Brenda Galligan Karen M. Overtoom R.E.

  19 Locust Ln, Aquinnah, MA 02535
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  /39

  $7,775,000

  • 6 Beds
  • 34.5 Baths
  • 5,982 Sq Ft

  19 Locust Ln, Aquinnah, MA 02535

  This beautifully designed and built home is privately sited on 12.23 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone fireplace and concrete floors heated by radiant heat. French doors

  Brenda Galligan Karen M. Overtoom R.E.

  19 Locust Ln, Aquinnah, MA 02535
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  /23

  $1,625,000

  • 5 Beds
  • 5 Baths
  • 2,316 Sq Ft

  345 North Rd, Chilmark, MA 02535

  Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  345 North Rd, Chilmark, MA 02535
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  /52

  $16,500,000

  • 6 Beds
  • 9 Baths
  • 4,820 Sq Ft

  68 N Water St, Edgartown, MA 02539

  This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon

  Thomas Wallace Wallace & Co. Sotheby's

  68 N Water St, Edgartown, MA 02539
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  /6

  $1,850,000

  • Land
  • 1.86 Acres
  • $994,624 per Acre

  22 Paddock Rd, Oak Bluffs, MA 02568

  THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground

  Marilyn Moses Ocean Park Realty Inc

  22 Paddock Rd, Oak Bluffs, MA 02568
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  /26

  $9,750,000

  • 5 Beds
  • 5 Baths
  • 3,550 Sq Ft

  1 Field Club Dr, Edgartown, MA 02539

  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

  Thomas Wallace Wallace & Co. Sotheby's International Realty

  1 Field Club Dr, Edgartown, MA 02539
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  /49

  $3,850,000

  • 6 Beds
  • 4 Baths
  • 3,665 Sq Ft

  25 Beetle Swamp Rd, Edgartown, MA 02539

  Located at the end of Sweetened Water Farm and surrounded by conservation land, lies this beautiful nearly 5-acre property with incredible and expansive views back across the open fields to the horse pastures and barn. There is a 5-bedroom / 3-bath main house featuring an open floor plan, a screened porch and spacious decks. Additionally, there is a 6-stall horse barn with a one-bedroom apartment

  Gerrett Conover Landvest MV

  25 Beetle Swamp Rd, Edgartown, MA 02539
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  /28

  $10,500,000

  • 7 Beds
  • 6 Baths
  • 3,888 Sq Ft

  47 E Chop Dr, Oak Bluffs, MA 02568

  East Chop direct waterfront – Enjoy the ultimate. in waterfront living experiences. Features 6 bedrooms, spectacular water views, dock with 9 slips, and just steps from beaches, tennis club, downtown and ferries to mainland! Property has been extensively renovated recently. Uses include -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion,2.) Currently

  Perry Patterson MV Luxury Homes LLC

  47 E Chop Dr, Oak Bluffs, MA 02568
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  /65

  $2,799,000

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style . 4 bedrooms & 3 bathrooms in main house & 2 bedrooms & 1 bath guest cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  $6,995,000 New Construction

  • 6 Beds
  • 7 Baths
  • 5,466 Sq Ft

  9 Duarte Cir, Edgartown, MA 02539

  NEW CONSTRUCTION: Coastal inspired Katama Gambrel with swimming pool and pool house conveniently located to both downtown and beaches. Exquisite design and finish with generous proportions throughout the home. Designed as a hub for all Martha's Vineyard activities in summer or year-round, this is an exceptional retreat to be cherished by multiple generations. The layout centers on an expansive

  Peyton Wallace Studio Realty

  9 Duarte Cir, Edgartown, MA 02539
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  /29

  $33,000,000 New Construction

  • 9 Beds
  • 11 Baths
  • 7,190 Sq Ft

  61 Butlers Cove Rd, Edgartown, MA 02539

  Beach Farm is a breathtaking 18.6 acre waterfront estate on Martha’s Vineyard featuring unrivaled privacy, serenity, awe-inspiring views, private beaches, water sports and a rare walking path to the pristine beaches of the south shore. This truly one-of-a-kind estate borders Edgartown Great Pond, the famed South Shore, and is part of the storied Herring Creek Farm, an exclusive 200+ acre enclave

  Brian Dougherty Corcoran Property Advisors

  61 Butlers Cove Rd, Edgartown, MA 02539
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  /7

  $10,850,000 New Construction

  • 7 Beds
  • 8 Baths
  • 12,051 Sq Ft

  14 Trapps Pond Rd, Edgartown, MA 02539

  Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized

  Gerrett Conover Landvest MV

  14 Trapps Pond Rd, Edgartown, MA 02539
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  /11

  $4,250,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,200 Sq Ft

  11 Bernard Way, Edgartown, MA 02539

  To be built by a luxury home builder! Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, this Coastal Contemporary-styled home can be completed by July of 2026. Please review the digital renderings which show the vision for this high-end 5-bedroom home, swimming pool and guest house/pool house. High-end details include all ensuite bedrooms in the main house,

  Mark Jenkins Wallace & Co. Sotheby's

  11 Bernard Way, Edgartown, MA 02539
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  /10

  $4,995,000 New Construction

  • 5 Beds
  • 5 Baths
  • 4,185 Sq Ft

  41 Crowell Ln, Tisbury, MA 02568

  Slated for summer 2025 occupancy and nestled in the picturesque landscape of West Chop, this luxurious new development by Novo Builds offers an exquisite blend of modern design and coastal charm. Known for their innovative designs and high-quality craftsmanship, Novo Builds is transforming this iconic island with their latest project, providing an ideal sanctuary for families or those who love to

  Joe & Nicole Holland Vineyard Dream Realty LLC

  41 Crowell Ln, Tisbury, MA 02568
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  /32

  $22,950,000 New Construction

  • 7 Beds
  • 9 Baths
  • 8,200 Sq Ft

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

  This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

  Gerrett Conover Landvest MV

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568
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  /73

  $13,995,000 New Construction

  • 7 Beds
  • 9 Baths
  • 6,343 Sq Ft

  5 Briggs Rd, Edgartown, MA 02539

  NEW CONSTRUCTION - COMPLETED. POND FRONT on WINTUCKET COVE. The epitome of Luxury Living, yet understated. 6,343 sq.ft., 7 Bed, 9 Bath home, w/16ft x 42ft saltwater heated pool, 2 car garage & a dramatic over sized screened porch w/11ft high ceilings. Discover a beautiful Vineyard oasis on 9.2 acres of land on the South Shore w/376ft of frontage on Wintucket Cove. An expansive property, merging

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  5 Briggs Rd, Edgartown, MA 02539

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