Dukes County MA Homes for Sale

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  /26

  $1,597,500

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  190 Longview Rd, Vineyard Haven, MA 02568

  Ask listing office. This property is in West Tisbury, 02575 NOT Tisbury 02568

  Kathleen Kendrick Kathleen Kendrick

  190 Longview Rd, Vineyard Haven, MA 02568
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  /39

  $5,325,000

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

  Katherine Donahue Sandpiper Realty Inc

  4 Canonicus Ave, Oak Bluffs, MA 02557
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  /42

  $1,895,000

  • 3 Beds
  • 4 Baths
  • 2,558 Sq Ft

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

  Katherine Donahue Sandpiper Realty Inc

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
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  /20

  $910,000

  • 2 Beds
  • 1 Bath
  • 834 Sq Ft

  21 Clay Pit Rd, Edgartown, MA 02539

  EDGARTOWN COTTAGE ON A COUNTRY LANE - Nestled on a spacious .56-acre lot in the Lily Pond District, this charming 2-bedroom, 1-bath cottage offers a rare opportunity to create your own Island haven. Renovate or build to suit just a short distance from all that Edgartown village has to offer — shops, restaurants, harbor, and beaches — you’ll enjoy both privacy and convenience in one of the

  Leslie C. Floyd Portfolio Real Estate, Inc.

  21 Clay Pit Rd, Edgartown, MA 02539
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  /14

  $3,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  160 Katama Rd, Edgartown, MA 02539

  Gorgeous post-and-beam home built by a respected contractor. This spacious house plus detached guest quarters is on the outskirts of the village conveniently located on the way to South Beach. The property is at the end of a long driveway off Katama Road and is private and quiet. Upon arrival, you are greeted by beautiful landscaping with large beds of hydrangeas. There are 3 bedrooms in the main

  Bonnie Pierce Wallace & Co. Sotheby's

  160 Katama Rd, Edgartown, MA 02539
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  /33

  $8,995,000

  • 11 Beds
  • 8.5 Baths
  • 9,678 Sq Ft

  5 Louis Field Rd, Edgartown, MA 02539

  SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of an extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

  Wendy Harman Compass | Point B

  5 Louis Field Rd, Edgartown, MA 02539
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  /35

  $1,690,000

  • 3 Beds
  • 4 Baths
  • 3,027 Sq Ft

  110 Clover Hill Dr, Vineyard Haven, MA 02568

  Perfect Location just minutes from Downtown and the ferry terminal this updated year round home offers flexible living with three bedrooms four bathrooms plus additional interior/exterior living areas to enjoy. It has a private lower level apartment large fenced in yard and a detached garage for boat/car storage. Many renovations have been completed. Seven new mini-splits (7), bathrooms

  Janna O'Loughlin Portfolio Real Estate, Inc.

  110 Clover Hill Dr, Vineyard Haven, MA 02568
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  /29

  $33,000,000

  • 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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  /41

  $1,850,000

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  4 Hye Ln, Edgartown, MA 02539

  Pristine and superbly maintained, this two bedroom home and two bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. Two additional bedrooms in the main house are possible within the existing footprint with appropriate town approvals.There is an additional 668 sq. ft.of finished space in the

  Lynn Buder Sandpiper Realty Inc

  4 Hye Ln, Edgartown, MA 02539
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  /4

  $425,000

  • Land
  • 0.23 Acre
  • $1,845,419 per Acre

  0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568

  Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with Dukes

  Rosemary Byrd Ocean Park Realty Inc

  0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
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  /21

  $650,000

  • 2 Beds
  • 1 Bath
  • 725 Sq Ft

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

  Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

  Stephanie Roache Donnelly + Co.

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
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  /37

  $6,250,000

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /7

  $10,850,000

  • 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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  /36

  $4,950,000

  • 5 Beds
  • 4 Baths
  • 3,413 Sq Ft

  122 Old Farm Rd, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

  Mark Jenkins Wallace & Co. Sotheby's

  122 Old Farm Rd, Chilmark, MA 02535
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  /34

  $4,950,000

  • 5 Beds
  • 4.5 Baths
  • 3,413 Sq Ft

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
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  /18

  $899,000

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft

  1 Onondaga Ave, Oak Bluffs, MA 02557

  Charming Single Story Cottage on a Beautiful Oak Bluffs Lot - Perfect for Your Vineyard Retreat! Discover the timeless appeal of this cozy 1-bedroom, 1-bath home nestled on a spacious 0.31-acre lot in the heart of Oak Bluffs. Built in 2000 and lovingly owned by the same family since its inception, this property offers a fantastic opportunity for both comfortable living and future expansion.

  Leslie Floyd Portfolio Real Estate Inc.

  1 Onondaga Ave, Oak Bluffs, MA 02557
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  /11

  $4,250,000

  • 5 Beds
  • 5.5 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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  /43

  $1,850,000

  • 3 Beds
  • 3.5 Baths
  • 2,986 Sq Ft

  1 Harpoon Hollow, Aquinnah, MA 02535

  Beautiful, solidly custom built home featuring red oak Post and Beam work throughout. The many unique and attractive features are sure to delight the most discerning buyer. Abuts 5.9 acres of forever protected Landbank property extending the 2 private acres of this property for extraordinary privacy. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home.

  Elaine Vanderhoop Beachcombers of MV

  1 Harpoon Hollow, Aquinnah, MA 02535
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  /36

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  40 Scotchmans Ln, Vineyard Haven, MA 02568

  A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

  Jim Osmundsen Donnelly + Co.

  40 Scotchmans Ln, Vineyard Haven, MA 02568
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  /13

  $5,300,000

  • 5 Beds
  • 5.5 Baths
  • 5,394 Sq Ft

  23 Pinehurst Rd, Edgartown, MA 02539

  New Construction with POOL, GUEST HOUSE and PRIMARY HOME, all within close proximity to Main Street, Edgartown. This gorgeous four bedroom gambrel home offers comfort and ease of coastal luxurious living. The primary home welcomes you with a two story foyer which opens to a large great room with a gourmet kitchen, with a bar area and a central island offering seating for at least four. The

  Michele Casavant Vineyard Village Realty

  23 Pinehurst Rd, Edgartown, MA 02539
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  /46

  $2,395,000

  • 5 Beds
  • 3.5 Baths
  • 3,873 Sq Ft

  50 Hidden Cove Rd, Edgartown, MA 02539

  Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

  Sean Federowicz Landmarks at TODAY Real Estate

  50 Hidden Cove Rd, Edgartown, MA 02539
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  /46

  $6,750,000

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

  44 Cencelle St, Chilmark, MA 02535

  This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

  Meg Bodnar Tea Lane Associates

  44 Cencelle St, Chilmark, MA 02535
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  /20

  $895,000

  • Land
  • 0 Acre

  0 Jeffers Way Unit 73387831, Aquinnah, MA 02535

  This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed archeological

  Brenda Galligan Karen M. Overtoom R.E.

  0 Jeffers Way Unit 73387831, Aquinnah, MA 02535
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  /8

  $1,695,000

  • Land
  • 0 Acre

  19A Locust Ln, Aquinnah, MA 02535

  This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

  Brenda Galligan Karen M. Overtoom R.E.

  19A Locust Ln, Aquinnah, MA 02535
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  /23

  $1,090,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  54 Towanticut Ave, Oak Bluffs, MA 02568

  Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace and lovely built-ins, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room

  JoJo Lambert Island Home Realty Inc.

  54 Towanticut Ave, Oak Bluffs, MA 02568
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  /62

  $1,895,000

  • 3 Beds
  • 2 Baths
  • 2,462 Sq Ft

  129 Beach Rd, Tisbury, MA 02568

  Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private access, is

  Michele Moore Island Real Estate

  129 Beach Rd, Tisbury, MA 02568
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  /39

  $1,399,000

  • 2 Beds
  • 3 Baths
  • 1,632 Sq Ft

  35 Stevens Ave, Oak Bluffs, MA 02557

  Nestled in a quiet Oak Bluffs neighborhood, this colonial-style home and its surrounding area gives the feel of being up-Island. The well-kept home was built in 2008 and is move-in ready. Located 1 mile to Circuit Avenue, and less than a mile to both the Oak Bluffs School and the Oak Bluffs Library, the property is also conveniently close to a bus stop and the bike path. Its many features include

  Paul Thoutsis Dockside Real Estate

  35 Stevens Ave, Oak Bluffs, MA 02557
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  /41

  $9,900,000

  • 8 Beds
  • 9 Baths
  • 8,560 Sq Ft

  150 E Chop Dr, Oak Bluffs, MA 02557

  Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

  Moira Lown Coldwell Banker Realty - Wellesley

  150 E Chop Dr, Oak Bluffs, MA 02557
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  /52

  $1,399,200 Open House 10/11

  • 4 Beds
  • 3 Baths
  • 2,961 Sq Ft

  208 Irenes Way, Tisbury, MA 02568

  Welcome to this 4 bedroom 3 bathroom 2,961 square foot home! Enjoy the open, first floor layout, finished walk out basement, beautiful hardwood flooring and a quality kitchen with new granite countertops. Just off of the kitchen there is a convenient first floor bedroom, bathroom and laundry room, as well as a lovely bonus space currently enjoyed as a sunroom with a sliding door to the large

  Emma Bryant Landmarks at TODAY Real Estate

  208 Irenes Way, Tisbury, MA 02568
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  /51

  $9,499,000

  • 4 Beds
  • 7 Baths
  • 5,458 Sq Ft

  43 Peases Point Way S, Edgartown, MA 02539

  Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

  Katherine Donahue Sandpiper Realty Inc

  43 Peases Point Way S, Edgartown, MA 02539
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  /26

  $2,000,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  12 Lobsterville Rd, Aquinnah, MA 02535

  12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

  Tina Palmer Conroy & Company R.E., Inc.

  12 Lobsterville Rd, Aquinnah, MA 02535
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  /49

  $6,490,000

  • 6 Beds
  • 8 Baths
  • 5,660 Sq Ft

  60 Meetinghouse Rd, Chilmark, MA 02535

  This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

  Jim Feiner Feiner Real Estate

  60 Meetinghouse Rd, Chilmark, MA 02535
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  /33

  $1,985,000

  • Land
  • 3.58 Acres
  • $554,469 per Acre

  4 Cedar Ln Unit 2.2, Chilmark, MA 02535

  Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with

  Jill Napior Tea Lane Associates

  4 Cedar Ln Unit 2.2, Chilmark, MA 02535
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  /12

  $1,325,000

  • Land
  • 4.12 Acres
  • $321,602 per Acre

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

  This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property

  Abby Rabinovitz Tea Lane Associates

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
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  /39

  $3,745,000

  • 5 Beds
  • 3 Baths
  • 2,791 Sq Ft

  20 James Pond Way, Vineyard Haven, MA 02568

  Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

  Sheila Morse Island Real Estate

  20 James Pond Way, Vineyard Haven, MA 02568
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  /21

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 2,312 Sq Ft

  7 Candlemaker Cir, Edgartown, MA 02539

  3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

  Roy Cutrer Jr Laer Realty Partners

  7 Candlemaker Cir, Edgartown, MA 02539
• 

  

  /3

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 2,311 Sq Ft

  7 Candle Maker Cir, Edgartown, MA 02539

  3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

  Roy Cutrer LAER Realty Partners

  7 Candle Maker Cir, Edgartown, MA 02539
• 

  

  /29

  $6,795,000

  • 3 Beds
  • 2.5 Baths
  • 2,589 Sq Ft

  57 Hines Point Rd, Vineyard Haven, MA 02568

  Lily Hill - a rare Hines Point offering that includes a waterfront home with exquisite views, a deep water mooring and dock, and 130 feet of private fine-sand beach. Poised on a knoll on the western shore of the Lagoon, Lily Hill evokes a more peaceful time with sweeping views of the sky and water. Enjoy a swim at your private beach morning, noon or night. Watch the play of light across the water

  Elissa Lash Tea Lane Associates

  57 Hines Point Rd, Vineyard Haven, MA 02568
• 

  

  /52

  $3,975,000

  • 4 Beds
  • 3 Baths
  • 2,704 Sq Ft

  370 Lighthouse Rd, Aquinnah, MA 02535

  Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes with year-round living amenities. Step inside to find an open-concept living space filled with natural

  Jill Napior Tea Lane Associates

  370 Lighthouse Rd, Aquinnah, MA 02535
• 

  

  /21

  $895,000

  • Land
  • 3.8 Acres
  • $235,526 per Acre

  0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535

  This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed

  Brenda Galligan Karen M. Overtoom R.E.

  0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535

Showing Results 121 - 160, Page 4 of 9