Dukes County MA Houses for Sale

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  /42

  $4,600,000

  • 3 Beds
  • 6 Baths
  • 3,171 Sq Ft

  15 Old Farm Rd, Chilmark, MA 02535

  CHILMARK BLISS- 15 Old Farm Rd, sits on over 3 beautiful acres, blends refined architecture with serene natural beauty. Reimagined in 2020 by Peter Breese and crafted by Doug Best, this timeless retreat offers open-concept living, anchored by a stunning kitchen, large pantry, screen porch, and a stone fireplace, with seamless indoor-outdoor flow. The main level includes a sunny primary suite

  Tina Miller Compass

  15 Old Farm Rd, Chilmark, MA 02535
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  /34

  $5,450,000

  • 5 Beds
  • 4.5 Baths
  • 2,913 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 original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

  Mark Jenkins Wallace & Co. Sotheby's International Realty

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

  $945,000

  • 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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  /41

  $3,400,000

  • 5 Beds
  • 4 Baths
  • 3,361 Sq Ft

  735 Franklin St, Vineyard Haven, MA 02568

  Welcome to this stunning 4-bedroom, 3-bathroom primary residence along with a 1-bedroom studio apartment over the one-car garage, ideally located in West Chop! Together, they include approximately 3,871 square feet of beautifully renovated living space (an additional 510 sqft of living space on the 3rd floor in the main house is not included on the town assessment). Situated on a .99-acre lot,

  Emily Flake Viewpoints

  735 Franklin St, Vineyard Haven, MA 02568
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  /24

  $2,150,000 Open Fri 3PM - 6PM

  • 3 Beds
  • 3 Baths
  • 2,126 Sq Ft

  17 Oakdale Dr, Edgartown, MA 02539

  17 Oakdale Drive is perfectly positioned between Edgartown Village and State Beach. This charming 3-bedroom, 3-bathroom residence offers refined Vineyard living in one of the island's most desirable locations. Sited on a beautifully landscaped 0.62-acre lot and abutting Edgartown Golf Club property on two sides, the setting offers a rare sense of privacy and open space. The 2,126 sq. ft. home is

  Andrew McElhinney Compass Massachusetts, LLC

  17 Oakdale Dr, Edgartown, MA 02539
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  /41

  $1,850,000

  • 4 Beds
  • 4 Baths
  • 2,986 Sq Ft

  1 Harpoon Hollow, Aquinnah, MA 02535

  Custom built Red Oak Post and Beam country home, in the style of an Old English cottage mansion. The many unique and attractive features are sure to delight the most discerning buyer. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home. Throughout, this intriguing, creatively designed home, you will notice the high quality and attention to detail.

  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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  /30

  $3,900,000

  • 4 Beds
  • 2 Baths
  • 2,813 Sq Ft

  179 Tisbury Ln E, West Tisbury, MA 02575

  Seven Gates Farm: This warm and convivial home in one of the island’s most desirable communities is less than 1/10th of a mile to the private association beach. The house was designed to accentuate indoor-outdoor living; there is generous decking for morning or afternoon sun, and a screened porch which is the perfect place to enjoy shade and breeze after a day spent at one of the nearby beaches.

  Mark Jenkins Wallace & Co. Sotheby's

  179 Tisbury Ln E, West Tisbury, MA 02575
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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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  /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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  /20

  $4,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,716 Sq Ft

  1 Wilsons Ln, Edgartown, MA 02539

  NEWLY CONSTRUCTED gambrel home with a heated saltwater POOL, close to SOUTH BEACH and EDGARTOWN VILLAGE! The entry foyer presents with an oversized lounge area to the right and a spectacular great room ahead. The great room offers a cathedral ceiling and rear wall of two story windows with a gas fireplace. The great room opens to the dining room which features a wall of sliding glass doors

  Michele Casavant Vineyard Village Realty

  1 Wilsons Ln, Edgartown, MA 02539
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  /41

  $2,200,000 Open Tue 11:30AM - 1:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  56 Bridle Path Rd, Vineyard Haven, MA 02568

  POOL AND LUSH GARDENS Situated on three acres, abutting nearly 25 acres of conservation land, this well-crafted home offers the ideal blend of tranquility and convenience. Step inside to discover over 2,500 square feet of thoughtfully designed living space. The bright and inviting living room, complete with a cozy fireplace, opens onto the kitchen and dining area. Head out to a comfortable

  Tina Miller Compass

  56 Bridle Path Rd, Vineyard Haven, MA 02568
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  /62

  $1,995,000

  • 4 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,

  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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  /50

  $4,495,000

  • 4 Beds
  • 5 Baths
  • 2,792 Sq Ft

  118 William St, Vineyard Haven, MA 02568

  The Captain George Harding Home sits gracefully on the westerly side of iconic William Street overlooking Vineyard Haven village with distant views of the harbor. This immaculate and re-imagined Gothic Revival offers both timeless elegance and modern luxury. Completed in 2024, the comprehensive down-to-the-studs renovation includes all new systems like central air and dehumidification. Every

  Alexis Holden Tea Lane Associates

  118 William St, Vineyard Haven, MA 02568
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  /42

  $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

  $1,460,000

  • 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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  /52

  $9,995,000

  • 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

  Katie Donahue Sandpiper Realty

  43 Peases Point Way S, Edgartown, MA 02539
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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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  /76

  $3,995,000

  • 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
  • 4 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
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  /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
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  /29

  $6,795,000

  • 3 Beds
  • 3 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
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  /101

  $4,600,000

  • 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
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  /30

  $1,950,000

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  16 Schoolhouse Rd, Edgartown, MA 02539

  Vacation Getaway in Edgartown Estates - This sunny and welcoming contemporary home could be yours this summer! With an open layout, vaulted ceilings, and lots of windows and glass doors, the home feels bright and airy. Step outside to a spacious wrap-around deck--great for relaxing or entertaining. Inside, the living, dining, and kitchen areas flow nicely and are just the right size for

  Lesley Heidt Sandpiper Realty Inc

  16 Schoolhouse Rd, Edgartown, MA 02539
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  /35

  $13,000,000

  • 5 Beds
  • 5 Baths
  • 3,758 Sq Ft

  6 Wakeman Rd, Chilmark, MA 02535

  A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

  Julianna Flanders Flanders Real Estate

  6 Wakeman Rd, Chilmark, MA 02535
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  /25

  $3,600,000

  • 3 Beds
  • 3 Baths
  • 4,382 Sq Ft

  88 & 90 Quenames Rd, Chilmark, MA 02535

  Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

  Julianna Flanders Flanders Real Estate

  88 & 90 Quenames Rd, Chilmark, MA 02535
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  /40

  $5,295,000

  • 7 Beds
  • 5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
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  /18

  $1,550,000

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

  61 Dodgers Hill Rd, Edgartown, MA 02539

  Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space. The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

  Ellen Valentgas Sotheby's International Realty

  61 Dodgers Hill Rd, Edgartown, MA 02539
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  /18

  $1,550,000

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

  61 Dodgers Hole Rd, Edgartown, MA 02539

  Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space.The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

  Ellen Valentgas Sotheby's International Realty

  61 Dodgers Hole Rd, Edgartown, MA 02539
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  /87

  $4,250,000

  • 4 Beds
  • 3 Baths
  • 3,159 Sq Ft

  3 Down Harbor Rd, Edgartown, MA 02539

  Exceptional Opportunity in Down Harbor.Here’s a rare chance to own a property in Edgartown’s exclusive Down Harbor community. Known for its serene setting and prime access to Katama Bay, this neighborhood offers more than just scenic beauty— Ownership includes deeded rights to a pristine, sandy association beach, along with coveted mooring and dock privileges on Katama Bay — a benefit

  Susan Wallo Compass | The O'Hanlon Group

  3 Down Harbor Rd, Edgartown, MA 02539
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  /30

  $6,000,000

  • 5 Beds
  • 7 Baths
  • 5,104 Sq Ft

  10 Puwal Ln, Edgartown, MA 02539

  KATAMA COMPOUND WITH POOL - TURNKEY & READY FOR USE THIS SUMMER! In an enclave of luxury homes in Katama, this 2021-built 5 bedroom, 5 bathroom property with three half-baths is being delivered turnkey with fine furnishings and most artwork. The home has everything the modern buyer wants, including two primary bedroom suites (one upstairs, one downstairs), all bedrooms with ensuite bathrooms, two

  Mark Jenkins Wallace & Co. Sotheby's

  10 Puwal Ln, Edgartown, MA 02539
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  /3

  $925,000

  • 2 Beds

  90 17th St N, Edgartown, MA 02539

  90 Seventeenth Street NorthEdgartown, MassachusettsFOR SALEHere is a chance for you to own a water view property in Edgartown. Property is located just off the Boulevard on a quiet dead end lane. This property has been in the same family for decades and is now offered for sale. It is a blank canvas for you to create your dream home. Interior has been gutted and is ready for your renovation. The

  Theodore Saulnier TAS Real Estate, LLC

  90 17th St N, Edgartown, MA 02539
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  /34

  $4,350,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  131 State Rd, Chilmark, MA 02535

  Magical waterfront Quitsa pond cottage with private dock. This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates

  Jim Feiner Feiner Real Estate

  131 State Rd, Chilmark, MA 02535
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  /46

  $2,050,000

  • 4 Beds
  • 2.5 Baths
  • 2,855 Sq Ft

  5 Bayes Hill Cir, Vineyard Haven, MA 02568

  On a quiet cul-de-sac in the Bayes Hill neighborhood is this spacious traditional Colonial-style home adorned with charm. As you enter the home from the idyllic covered porch, you are welcomed into the foyer. The home is filled with intimate spaces while offering the opportunity for larger parties to gather. The living room has built-in shelving that flank the gas fireplace and it is connected to

  Michele Moore Island Real Estate

  5 Bayes Hill Cir, Vineyard Haven, MA 02568
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  /37

  $7,975,000

  • 4 Beds
  • 5 Baths
  • 3,777 Sq Ft

  25 Osprey Ln, Chilmark, MA 02535

  Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

  Deb Hancock Hancock Real Estate

  25 Osprey Ln, Chilmark, MA 02535
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  /28

  $1,695,000

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  5 Scottys Ln, Vineyard Haven, MA 02568

  Attention Developers and Island Lovers! Take note of this rare opportunity in a prime West Tisbury Location with a new price! This mid-century home with excellent bones fronts on Seth's Pond, a beloved locale perfect for swimming, paddle-boarding, and kayaking. 5 Scotty's Lane has an existing 4-bedroom main house with the first floor and lower walk-out level equaling 2,704 of finished space. This

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  5 Scottys Ln, Vineyard Haven, MA 02568
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  /34

  $1,750,000

  • 5 Beds
  • 2 Baths
  • 1,440 Sq Ft

  393 Lighthouse Rd, Aquinnah, MA 02535

  Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

  Julianna Flanders Flanders Real Estate

  393 Lighthouse Rd, Aquinnah, MA 02535
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  /59

  $1,925,000

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

  212 Charles Neck Way, Vineyard Haven, MA 02568

  This beautifully renovated contemporary South Shore retreat, located in a tranquil setting, features three bedrooms, two and one-half bathrooms, central air, all new appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove

  Perry Patterson MV Luxury Homes

  212 Charles Neck Way, Vineyard Haven, MA 02568
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  /27

  $1,795,000

  • 3 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  71 6th St N, Edgartown, MA 02539

  Classic three-bedroom farmhouse offers the perfect blend of island charm and laid-back comfort. Located within walking distance to scenic Sengekontacket Pond, it’s an ideal retreat for nature lovers, kayakers, or anyone looking to enjoy the Vineyard lifestyle. The home features a welcoming front porch and back deck—perfect spaces to relax, dine, or entertain outdoors. Inside, you'll find a warm

  Erin Leighton Compass

  71 6th St N, Edgartown, MA 02539

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