Dukes County MA Homes for Sale

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  /52

  $12,500,000

  • 5 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  18 Spruce Gate Rd, Chilmark, MA 02535

  Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

  Alyssa Halisky Wallace & Co. Sotheby's

  18 Spruce Gate Rd, Chilmark, MA 02535
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  /51

  $7,350,000

  • 4 Beds
  • 5 Baths
  • 3,490 Sq Ft

  308 South Rd, Chilmark, MA 02535

  Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets.

  Rose Ryley Sandpiper Realty Inc

  308 South Rd, Chilmark, MA 02535
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  /44

  $2,699,000

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

  111 Eastville Ave, Oak Bluffs, MA 02557

  Motivated Seller!! 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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  /15

  $5,100,000

  • Land
  • 2.34 Acres
  • $2,182,285 per Acre

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557

  A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy

  Alyssa Halisky Wallace & Co. Sotheby's

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557
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  /29

  $1,725,000

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  654 Lighthouse Rd, Aquinnah, MA 02535

  Waterview beach house in Aquinnah. Just a short deeded walking path to the calm and sandy shores of the North Shore. The traditional layout features the kitchen, living room, dining room, and a full bath on the first floor. The living room offers water views, a cozy fireplace, and multiple sliding doors leading out to the wrap-around porch. Upstairs, the views are even more stunning!

  Heidi Vanderhoop Tea Lane Associates

  654 Lighthouse Rd, Aquinnah, MA 02535
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  /33

  $2,199,000

  • 3 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  6 Church St, Aquinnah, MA 02535

  This beautifully renovated contemporary home is perched on a hillside, offering views of the Atlantic Ocean. Upon entering the home has a light and airy atmosphere with cathedral ceilings and a wall of windows connecting you with the outdoors. The main level consists of an open-concept kitchen, living, and dining area with soaring ceilings and sliding glass doors that overlook the treetops of

  Heidi Vanderhoop Tea Lane Associates

  6 Church St, Aquinnah, MA 02535
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  /16

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

  East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, 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 kitchen with Bosch appliances, living

  Perry Patterson MV Luxury Homes, LLC

  47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
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  /12

  $1,995,000

  • 2 Beds
  • 1 Bath
  • 879 Sq Ft

  47 E Chop Dr Unit 4, Oak Bluffs, MA 02568

  East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the ''Tivoli'', features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
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  /37

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  /19

  $2,295,000

  • 4 Beds
  • 5 Baths
  • 2,820 Sq Ft

  71 Netock Ave, Oak Bluffs, MA 02557

  On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

  Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
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  /43

  $7,450,000

  • 5 Beds
  • 2.5 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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  /17

  $1,995,000

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft

  47 E Chop Dr Unit 3, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
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  /13

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft

  47 E Chop Dr Unit 2, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
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  /10

  $549,000

  • Land
  • 1.08 Acres
  • $508,333 per Acre

  519 Edgartown Rd Unit 8.1, Tisbury, MA 02568

  Nestled in a high, gently rolling landscape, this beautiful parcel is ready for your vision. With town water and power already at the site, it's an ideal setting for a dream home. Surrounded by conservation land on two sides, and just steps from the trailhead to the Land Bank's Beech Tree Preserve, you'll enjoy direct access to serene paths that lead to the Lagoon—perfect for kayaking,

  Meg Bodnar Tea Lane Associates

  519 Edgartown Rd Unit 8.1, Tisbury, MA 02568
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  /4

  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  9 Hagerty Dr, Tisbury, MA 02568

  West Chop Dream Home in the Making!Experience the charm of this brand-new Shingle Style Colonial, currently under construction—where modern luxury meets timeless elegance. Featuring 4 spacious bedrooms, 4 full baths, and a half bath, this inviting home offers ample space for relaxing, entertaining, and everything in between. You will be wired for sound both inside and poolside so step

  Lisa Gilberto C McManus Realty Group

  9 Hagerty Dr, Tisbury, MA 02568
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  /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

  $1,095,000

  • 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
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  /37

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Discover this stunning newly contructed single-family home in the heart of downtown Vineyard Haven. This beautifully crafted 3-bedroom, 3-bathroom residence offers high-end finishes and thoughtful design throughout.The modern kitchen and bathrooms feature elegant quartz countertops, while tile showers with custom glass enclosures add a touch of luxury. Each bedroom includes spacious

  Mike Sawyer Sawyer Realty Group

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /4

  $1,950,000

  • Land
  • 1.1 Acres
  • $1,771,278 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
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  /5

  $1,950,000

  • Land
  • 1.1 Acres
  • $1,772,727 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

  $1,625,000

  • 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

  $1,550,000

  • 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

  $1,649,000

  • 3 Beds
  • 2.5 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

  $1,295,000

  • Land
  • 4.4 Acres
  • $294,318 per Acre

  37 Bijah's Way Unit 96, 101, 102, 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 Unit 96, 101, 102, Chilmark, MA 02535
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  /5

  $1,300,000

  • Land
  • 0.5 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

  $2,195,000

  • 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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  /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
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  /5

  $1,300,000

  • Land
  • 0.5 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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  /61

  $8,900,000

  • 4 Beds
  • 8 Baths
  • 7,767 Sq Ft

  4 Jacobs Neck Rd, Edgartown, MA 02539

  This one of a kind property is extremely private, yet only 12 minutes to the airport or Edgartown Village. The 10+ acre parcel is bordered on two sides by Sheriff's Meadow Conservation land and miles of walking trails nearby. The dwellings and other structures are meticulously crafted and offer a range of possibilities. The "guest house" is 2300 sq ft with finished basement and loft space. The

  Deb Hancock Hancock Real Estate

  4 Jacobs Neck Rd, Edgartown, MA 02539
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  /48

  $1,795,000

  • 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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  /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
• 

  

  /37

  $2,240,000

  • 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
• 

  

  /46

  $14,500,000

  • 8 Beds
  • 7.5 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
• 

  

  /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

Showing Results 201 - 240, Page 6 of 9