Dukes County MA Homes for Sale

• 

  

  

  /14

  $499,000

  • Land
  • 0.60 Acre
  • $831,667 per Acre

  517 Edgartown Rd Unit 8.11, Tisbury, MA 02568

  A wonderful opportunity to build your island home on this high, level, and beautifully wooded parcel just minutes from town. With electricity and water already in place, the lot is ready for development. Mature trees provide natural privacy and a serene setting. Located next to the trailhead for the Land Bank’s Beech Tree Preserve, you’ll enjoy scenic walks that lead to the Lagoon—perfect for

  Meg Bodnar Tea Lane Associates

  517 Edgartown Rd Unit 8.11, Tisbury, MA 02568
• 

  

  

  /12

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 731 Sq Ft

  47 E Chop Dr Unit 1, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
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  /30

  $2,195,000

  • 4 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  4 Dempster Park, Oak Bluffs, MA 02568

  This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

  Perry Patterson MV Luxury Homes LLC

  4 Dempster Park, Oak Bluffs, MA 02568
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  /58

  $5,999,000

  • 4 Beds
  • 3.5 Baths
  • 2,995 Sq Ft

  135 The Blvd, Edgartown, MA 02539

  Exceptional Waterfront Living ~ Stunning, active views of Sengekontacket Pond and Nantucket Sound set the tone for this spectacular coastal retreat. Thoughtfully designed to showcase its breathtaking surroundings, the main house captures sweeping vistas from nearly every room. With over 300 feet of frontage, you'll enjoy immediate access to the water for swimming, paddleboarding, kayaking, and a

  Stephanie Roache Donnelly + Co.

  135 The Blvd, Edgartown, MA 02539
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  /39

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 2,046 Sq Ft

  9 Sampson Ave, Edgartown, MA 02539

  A home for all seasons and multiple purposes --- If you choose to have a comfortable, kick-your-shoes-off, not-fussy, beach home on the tranquil non-commercial island of Chappaquiddick, then this is your destination. The fabulous, pristine, seemingly endless miles of shoreline at East Beach, just over Dike Bridge, is only 1.3 miles distant. The gorgeous beaches at Wasque Point, where you also

  Lynn Buder Sandpiper Realty Inc

  9 Sampson Ave, Edgartown, MA 02539
• 

  

  /4

  $2,200,000

  • Land
  • 1.10 Acres
  • $2,000,000 per Acre

  5 Weaver Ln, Tisbury, MA 02568

  This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful

  Gerrett Conover Landvest MV

  5 Weaver Ln, Tisbury, MA 02568
• 

  

  /5

  $2,200,000

  • Land
  • 1.10 Acres
  • $2,000,000 per Acre

  0 Weaver Ln, Tisbury, MA 02568

  This 1.1-acre waterfront lot is located at the end of a quiet lane abutting 20+ acres of conservation land. The level and wooded lot sits high on a bluff overlooking the Lagoon. The lot has been engineered, and the bounds have been staked. A buyer would be able to connect to Town water nearby, and an enhanced septic system should allow at least four bedrooms. This quiet, beautiful neighborhood

  Gerret Conover LandVest MV

  0 Weaver Ln, Tisbury, MA 02568
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  /34

  $1,675,000

  • 2 Beds
  • 2.5 Baths
  • 1,532 Sq Ft

  26 Union St Unit 7, Tisbury, MA 02568

  Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower. Also on

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  26 Union St Unit 7, Tisbury, MA 02568
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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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  /28

  $1,650,000

  • 3 Beds
  • 2 Baths
  • 1,965 Sq Ft

  16 Majors Cove Ln, Edgartown, MA 02539

  Nestled in the prestigious Majors Cove community, this lovingly maintained home offers the perfect blend of comfort, style, and Vineyard charm. Enjoy access to exceptional amenities, including tennis courts, a boat launch ideal for kayaking to State Beach, and proximity to the bike path for easy access to Edgartown, Oak Bluffs, and Vineyard Haven. Set on a pleasantly landscaped lot, this inviting

  Stephanie Roache Donnelly + Co.

  16 Majors Cove Ln, Edgartown, MA 02539
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  /27

  $1,695,000

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  27 Chapde Ln, Tisbury, MA 02568

  CLASSIC STYLE MEETS TIMELESS CHARM. Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this meticulously maintained home provides a modern and spacious environment for comfortable island living. Upon entry, the home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen

  Wendy Harman Compass | Point B

  27 Chapde Ln, Tisbury, MA 02568
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  /16

  $1,325,000

  • Land
  • 4.40 Acres
  • $301,136 per Acre

  37 Bijah's Way, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this

  Elissa Lash Tea Lane Associates

  37 Bijah's Way, Chilmark, MA 02535
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  /18

  $989,000

  • 1 Bed
  • 2 Baths
  • 1,401 Sq Ft

  249 County Rd, Oak Bluffs, MA 02557

  This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy

  Katherine Donahue Sandpiper Realty Inc

  249 County Rd, Oak Bluffs, MA 02557
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  /5

  $1,300,000

  • Land
  • 0.50 Acre
  • $2,600,000 per Acre

  58 Marthas Rd Unit 70, Edgartown, MA 02539

  Island Grove Building Lot - A highly desirable Edgartown location near Morning Glory Farm, the Village, and South Beach. The 1/2 acre parcel is conforming in nature, allowing for maximum development. With approval for 6 bedrooms with sewer tie-in, the opportunities are endless! A great opportunity to get into this terrific community.

  Katie Donahue Sandpiper Realty

  58 Marthas Rd Unit 70, Edgartown, MA 02539
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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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  /37

  $2,275,000

  • 4 Beds
  • 3.5 Baths
  • 2,695 Sq Ft

  43C Dark Woods Rd, Edgartown, MA 02539

  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. Sited on a pleasant .77-acre lot, the property offers expansive space with a floor plan

  Stephanie Roache Donnelly + Co.

  43C Dark Woods Rd, Edgartown, MA 02539
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  /36

  $2,275,000

  • 4 Beds
  • 3.5 Baths
  • 2,695 Sq Ft

  43C Dark Woods Rd, Edgartown, MA 02539

  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

  Stephanie Roache Donnelly + Co.

  43C Dark Woods Rd, Edgartown, MA 02539
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  /25

  $1,895,000

  • 4 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  99 Old Purchase Rd, Edgartown, MA 02539

  Welcome to this charming post and beam-style home, privately located at the end of a cul-de-sac on .71 acres with proximity to over 50 acres of Land Bank and Sheriff's Meadow land with multiple trails and paths. Conveniently located to the bike path, Morning Glory Farm, the heart of Edgartown, and Meetinghouse Way, with direct access to South Beach, the location is ideal. The floor plan was

  Stephanie Roache Donnelly + Co.

  99 Old Purchase Rd, Edgartown, MA 02539
• 

  

  /5

  $1,300,000

  • Land
  • 0.50 Acre
  • $2,600,000 per Acre

  58 Marthas Rd, Edgartown, MA 02539

  Island Grove Building Lot - A highly desirable Edgartown location near Morning Glory Farm, the Village, and South Beach. The 1/2 acre parcel is conforming in nature, allowing for maximum development. With approval for 6 bedrooms with sewer tie-in, the opportunities are endless! A great opportunity to get into this terrific community.

  Katherine Donahue Sandpiper Realty Inc

  58 Marthas Rd, Edgartown, MA 02539
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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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  /48

  $1,875,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  3 Fulling Mill Rd, Chilmark, MA 02535

  Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly

  Jill Napior Tea Lane Associates

  3 Fulling Mill Rd, Chilmark, MA 02535
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  /34

  $2,895,000

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

  31 N Slope Ln, Chilmark, MA 02535

  Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working

  Bill Rossi Studio Realty

  31 N Slope Ln, Chilmark, MA 02535
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  /25

  $1,395,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  5 Pipn Rd, Edgartown, MA 02539

  Move-in ready Chappy retreat, just under a mile to swimmable Katama Bay.Tucked beside conservation land in a quiet wooded setting, this private 3 bedroom Cape offers comfort, charm, and relaxed island living— with room to gather, space to breathe, and nature at your doorstep.Designed for easy indoor-outdoor living with an open kitchen, sunny rooftop deck, stone patio, and a screened-in

  Katie Donahue Sandpiper Realty

  5 Pipn 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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  /37

  $2,290,000

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  22 Greenleaf Ave, Oak Bluffs, MA 02557

  Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

  Jennifer O'hanlon Compass

  22 Greenleaf Ave, Oak Bluffs, MA 02557
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  /44

  $9,250,000

  • 6 Beds
  • 8 Baths
  • 6,881 Sq Ft

  52 Fuller St, Edgartown, MA 02539

  Located on prestigious Fuller Street, half a block from Fuller Street Beach lies this classically styled home. The home features an amazing family room/kitchen with an abundance of retractable glass doors facing the pool area and 2 fireplaces. There is a dining room, office, den and ground floor bedroom with private bath. The second-floor features two large en suite guest rooms and a cathedral

  Gerrett Conover Landvest MV

  52 Fuller St, Edgartown, MA 02539
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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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  /26

  $1,395,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  5 Pip'N Rd, Edgartown, MA 02539

  Move-in ready Chappy retreat, just under a mile to swimmable Katama Bay.Tucked beside conservation land in a quiet wooded setting, this private 3 bedroom Cape offers comfort, charm, and relaxed island living-- with room to gather, space to breathe, and nature at your doorstep.Designed for easy indoor-outdoor living with an open kitchen, sunny rooftop deck, stone patio, and a screened-in porch

  Katherine Donahue Sandpiper Realty Inc

  5 Pip'N Rd, Edgartown, MA 02539
• 

  

  /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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  /28

  $3,250,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  311 E Chop Dr, Oak Bluffs, MA 02568

  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

  Gerrett Conover Landvest MV

  311 E Chop Dr, Oak Bluffs, MA 02568
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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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  /17

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  47 E Chop Dr Unit 5, Oak Bluffs, MA 02568

  East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new

  Perry Patterson MV Luxury Homes

  47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
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  /29

  $12,750,000

  • 4 Beds
  • 4 Baths
  • 2,050 Sq Ft

  16 Shotnaigher Ln, Chilmark, MA 02535

  New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

  Rebecca V Conroy Conroy & Company R.E., Inc.

  16 Shotnaigher Ln, Chilmark, MA 02535
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  /39

  $2,290,000

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  22 Greenleaf Ave, Oak Bluffs, MA 02539

  Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

  Jen O'Hanlon Compass | The O'Hanlon Group

  22 Greenleaf Ave, Oak Bluffs, MA 02539
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  /35

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  96 Dunham Ave, Vineyard Haven, MA 02568

  This attractive colonial style home is located in a terrific neighborhood. Just a short distance to the center of town with nearly 1/2 acre of rolling treed land. The features include a cathedral ceiling over the kitchen and dining room. A large fireplace highlights the living room. From upstairs you can look over the balcony to the dining area and kitchen below. The first floor bedroom with has

  Peter Cronig Cronigs Real Estate

  96 Dunham Ave, Vineyard Haven, MA 02568
• 

  

  /26

  $3,495,000

  • 4 Beds
  • 6 Baths
  • 3,793 Sq Ft

  28 Crocker Dr, Edgartown, MA 02539

  This beautifully renovated Katama retreat combines refined design, luxurious amenities, and thoughtfully crafted spaces. The main house features three bedrooms, including a peaceful primary suite with private deck access, a second en-suite bedroom, and a cozy bunkroom. The octagonal living room, skylit dining room with a gas fireplace, and a chef’s kitchen with quartz counters and high-end

  Jen O'Hanlon Compass | The O'Hanlon Group

  28 Crocker Dr, Edgartown, MA 02539
• 

  

  /4

  $550,000

  • Land
  • 0.33 Acre
  • $1,666,667 per Acre

  32 14th St S, Edgartown, MA 02539

  This is a fabulous opportunity to build your vineyard home. Only minutes to Edgartown Village shops, restaurants, and the Edgartown ferry. With a short 6 minute drive to Edgartown Beach for great summer fun! This lot is close to Vineyard Golf Club, as well as Edgartown Golf Club. Lot will accommodate a 2-3 bedroom home. Buyer of this lot will need to have it engineered, and seller has engaged a

  Rebecca Putnam Putnam Realty

  32 14th St S, Edgartown, MA 02539
• 

  

  /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
• 

  

  /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

Showing Results 201 - 240, Page 6 of 10