187

Dukes County MA Homes for Sale

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  • /16

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 1,512 Sq Ft

    1 Dodgers Hole Rd, Edgartown, MA 02539

    This four-bedroom cape-style home offers a comfortable and convenient lifestyle, ideally located just off the bike path with easy access to town and the bus route. Designed with an open floor plan, the main living area provides a seamless flow between the kitchen, dining, and living spaces—perfect for everyday living and entertaining. The first floor features two well-sized bedrooms and a full

    Nora Jardin Island Real Estate

    1 Dodgers Hole Rd, Edgartown, MA 02539
  • /36

    $4,695,000

    • 7 Beds
    • 4.5 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
  • /26

    $1,299,000

    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft

    9 Galway Rd, Vineyard Haven, MA 02568

    Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

    Julianna Flanders Flanders Real Estate

    9 Galway Rd, Vineyard Haven, MA 02568
  • /26

    $899,900

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    67 12th St S, Edgartown, MA 02539

    Turnkey ranch in a central island location with access to all towns and beaches. The main level features a sunny living area, kitchen, full bath, and three bedrooms, plus a front deck and a side deck perfect for outdoor dining, grilling, and laid-back summer evenings. The lower level offers an additional 960 sq ft with interior and exterior access, a full bath, two spacious rooms, laundry, and

    Janna O'Loughlin Portfolio Properties

    67 12th St S, Edgartown, MA 02539
  • /20

    $2,495,000

    • 1 Bed
    • 1.5 Baths
    • 1,236 Sq Ft

    218 Upper Main St, Edgartown, MA 02539

    Located on Upper Main Street in Edgartown’s BII zoning district, this versatile property is currently home to Lucky Hank’s restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you’ll find

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    218 Upper Main St, Edgartown, MA 02539
  • /26

    $1,395,000

    • 3 Beds
    • 1 Bath
    • 1,066 Sq Ft

    17 Chapman La, Edgartown, MA 02539

    Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat,

    Agent Photo

    Wendy Harman

    Compass

    (508) 290-8074

    17 Chapman La, Edgartown, MA 02539
  • /41

    $1,800,000

    • 4 Beds
    • 3 Baths
    • 1 Sq Ft

    18 Wood Duck Way, Edgartown, MA 02539

    Turnkey modern home with 4 bedrooms and 3 full baths, filled with natural light from large windows and soaring ceilings. The first floor offers three bedrooms and a full bath with double sinks, while warm oak and maple floors are accented by cherry stairs and custom built-ins.The open-concept second level features a spacious kitchen, living, and dining area, along with a private primary en suite

    Janna O'Loughlin Portfolio Properties

    18 Wood Duck Way, Edgartown, MA 02539
  • /45

    $1,765,000

    • 2 Beds
    • 2 Baths
    • 890 Sq Ft

    2 Great Rock Rd, Oak Bluffs, MA 02568

    Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property

    Susan Lemoie-Zarba Premier Properties

    2 Great Rock Rd, Oak Bluffs, MA 02568
  • /26

    $1,395,000

    • 3 Beds
    • 1 Bath
    • 1,066 Sq Ft

    17 Chapman Ln, Edgartown, MA 02539

    OPPORTUNITY KNOCKS: Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat,

    Wendy Harman Compass | Point B

    17 Chapman Ln, Edgartown, MA 02539
  • /11

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    52 Windsor Dr, Edgartown, MA 02539

    Nestled on a wooded lot only 3.5 miles from Edgartown Village, this three-bedroom home offers a bright, open-plan main level with kitchen, dining, and living area flowing onto a private deck—ideal for outdoor dining, morning coffee, or enjoying the outdoors. A first-floor bedroom and bath add convenience, while two upstairs bedrooms and a bath provide flexible space for families or guests. The

    Emma Kennedy Sandpiper Realty, Inc.

    52 Windsor Dr, Edgartown, MA 02539
  • /40

    $2,790,000

    • 3 Beds
    • 3.5 Baths
    • 2,898 Sq Ft

    4 Pip'N Rd, Edgartown, MA 02539

    Where Chappaquiddick’s natural beauty meets Edgartown sophistication, this impeccably maintained custom home offers thoughtful design and exceptional livability. The professionally styled interior features an inviting foyer, a gracious dining room open to a living room with fireplace and glass doors to the deck, and a gourmet kitchen with island and banquette. A sun porch, wet bar, powder room,

    Lesley Heidt Sandpiper Realty, Inc.

    4 Pip'N Rd, Edgartown, MA 02539
  • /28

    $999,000

    • 3 Beds
    • 2 Baths
    • 1,294 Sq Ft

    18 Windsor Dr, Edgartown, MA 02539

    Welcome to this light-filled Vineyard Cape brimming with potential, offering an open layout and abundant natural light. Vaulted ceilings enhance the spacious living and dining area, creating an airy setting for relaxing or entertaining. The kitchen has direct access to the outdoor deck, ideal for summer gatherings and al fresco dining. Two bedrooms and a full bathroom with laundry complete the

    Stephanie Roache Donnelly + Co

    18 Windsor Dr, Edgartown, MA 02539
  • /2

    $1,125,000

    • Land
    • 0.23 Acre
    • $4,853,322 per Acre

    15 Chapman Ln Unit 111.1, Edgartown, MA 02539

    OPPORTUNITY ABOUNDS: This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer (see notes below) creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the

    Wendy Harman Compass | Point B

    15 Chapman Ln Unit 111.1, Edgartown, MA 02539
  • /27

    $1,800,000

    • 3 Beds
    • 3 Baths
    • 2,293 Sq Ft

    10 Trotters Ln, West Tisbury, MA 02575

    Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

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

    10 Trotters Ln, West Tisbury, MA 02575
  • /55

    $2,395,000

    • 4 Beds
    • 2.5 Baths
    • 2,760 Sq Ft

    69 Whalers Walk, Edgartown, MA 02539

    EDGARTOWN – Beautifully landscaped property set on a lovely open, cleared lot with exceptional curb appeal, located just minutes from Downtown Edgartown and South Beach. This inviting home features many updates including a Tesla Solar Roof, with a SEVEN (7) bedroom sewer connection and an approval for a two car garage with a detached bedroom above. Currently configured as a four-bedroom, 2.5-bath

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    69 Whalers Walk, Edgartown, MA 02539
  • /29

    $2,600,000

    • 3 Beds
    • 1 Bath
    • 1,336 Sq Ft

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views.Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound—a setting that captures the

    Rene Ben David Ocean Park Realty Inc

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
  • /4

    $809,000

    • Land
    • 0.39 Acre
    • $2,074,359 per Acre

    7 Highland Ave, Vineyard Haven, MA 02568

    Rare opportunity in East Chop. Buildable lot in a beautiful, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible.

    Shera Toledo eXp Realty, LLC

    7 Highland Ave, Vineyard Haven, MA 02568
  • /37

    $7,950,000

    • 5 Beds
    • 7 Baths
    • 4,531 Sq Ft

    85 Reservoir Rd, Vineyard Haven, MA 02568

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

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • /17

    $1,700,000

    • Land
    • 0.85 Acre
    • $2,000,000 per Acre

    4 Wilson's Landing Unit 49.2, Edgartown, MA 02539

    Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed "by right" (certain restrictions apply to ADUs; an unrestricted 900 sq ft

    Mark Jenkins Wallace & Co. Sotheby's

    4 Wilson's Landing Unit 49.2, Edgartown, MA 02539
  • /42

    $16,900,000

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

    114 N Water St, Edgartown, MA 02539

    Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house

    Erin Hegarty Donnelly + Co.

    114 N Water St, Edgartown, MA 02539
  • /26

    $1,750,000

    • 3 Beds
    • 2.5 Baths
    • 2,862 Sq Ft

    103 Meadow View Rd, Oak Bluffs, MA 02557

    Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring

    Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, Oak Bluffs, MA 02557
  • /46

    $1,975,000

    • 3 Beds
    • 2.5 Baths
    • 1,902 Sq Ft

    81 Leland Ave, Vineyard Haven, MA 02568

    Close to town with exceptional indoor / outdoor flow & privacy.Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor

    Jill Napior Tea Lane Associates

    81 Leland Ave, Vineyard Haven, MA 02568
  • /19

    $1,700,000

    • Land
    • 0.85 Acre
    • $2,000,000 per Acre

    4 Wilson's Landing, Edgartown, MA 02539

    Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed ''by right'' (certain restrictions apply to ADUs; an unrestricted 900 sq ft

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    4 Wilson's Landing, Edgartown, MA 02539
  • /34

    $14,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,705 Sq Ft

    64 Squibnocket Farm Rd, Chilmark, MA 02535

    Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

    Tom Wallace

    64 Squibnocket Farm Rd, Chilmark, MA 02535
  • /29

    $2,500,000

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    16 South Rd, Chilmark, MA 02535

    Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly

    Michele Casavant Vineyard Village Realty

    16 South Rd, Chilmark, MA 02535
  • /39

    $3,995,000

    • 8 Beds
    • 6 Baths
    • 4,651 Sq Ft

    23 Beetle Swamp Rd, Edgartown, MA 02539

    Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses.

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    23 Beetle Swamp Rd, Edgartown, MA 02539
  • /40

    $1,695,000

    • 4 Beds
    • 2 Baths
    • 1,342 Sq Ft

    58 Road To the Plains, Edgartown, MA 02539

    Turnkey Katama Retreat – Welcome to this beautifully appointed, fully furnished home, offering the perfect blend of relaxed coastal living and effortless ownership. With a strong rental history and thoughtful upgrades throughout, this property is an exceptional opportunity as a year-round residence, vacation escape, or income-producing investment. At the heart of the outdoor experience is a

    Stephanie Roache Donnelly + Co

    58 Road To the Plains, Edgartown, MA 02539
  • /28

    $1,350,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft

    56 Garvin St, Oak Bluffs, MA 02557

    Single Story Bungalow — Turnkey & Walkable Lifestyle! Welcome to this beautifully updated home offering effortless single-level living and a bright, open layout designed for comfort and functionality. Turnkey and thoughtfully renovated, the property seamlessly blends classic charm with modern upgrades throughout. The updated kitchen features contemporary cabinetry, sleek countertops, and modern

    Casandra Hyland Sandpiper Realty, Inc.

    56 Garvin St, Oak Bluffs, MA 02557
  • /7

    $599,000

    • Land
    • 0.07 Acre
    • $8,160,763 per Acre

    112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557

    Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park. This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

    Rose Ryley Wallace & Co. Sotheby's

    112 Dukes County Ave Unit 209, Oak Bluffs, MA 02557
  • /7

    $599,000

    • Land
    • 0.07 Acre
    • $8,557,143 per Acre

    112 Dukes County Ave, Oak Bluffs, MA 02557

    Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha’s Vineyard’s most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park.This level lot includes an existing poured concrete foundation and Martha’s Vineyard Commission–approved

    Rose Ryley Wallace & Co. Sotheby's International Realty

    112 Dukes County Ave, Oak Bluffs, MA 02557
  • /27

    $8,500,000

    • 4 Beds
    • 6 Baths
    • 3,497 Sq Ft

    24 Katama Bay View Rd, Edgartown, MA 02539

    This classic New England waterview home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room

    Tom Wallace Wallace & Co. Sotheby's International Realty

    24 Katama Bay View Rd, Edgartown, MA 02539
  • /26

    $3,895,000

    • 4 Beds
    • 4 Baths
    • 1,590 Sq Ft

    99 Cooke St, Edgartown, MA 02539

    LUXURY COTTAGE-STYLE LIVING IN THE VILLAGE – WITH A POOL! This updated classic cottage is located in the heart of Edgartown Village, less than a quarter mile to Main Street. Upon arrival, you are greeted by a spacious porch and elegant French door entry that lead you into the dramatic foyer. The open living plan with kitchen, dining, and living area is light and bright. The first floor opens out

    Bonnie Pierce Wallace & Co. Sotheby's

    99 Cooke St, Edgartown, MA 02539
  • /24

    $1,999,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • /11

    $1,200,000

    • 3 Beds
    • 3 Baths
    • 1,581 Sq Ft

    15 Goah Way, Vineyard Haven, MA 02568

    2 bedroom 2 bath cottage with 1 bedroom 1 bath ADU. Large 15,950 square foot lot, short distance to school and town. Second floor bedroom space is large and possibly convertable to 2 bedrooms. New windows and 2 mini split systems, ADU also has a mini split unit. ADU is beleived to have been built in 2017. Property is loacted in Tashmoo watershed district and will require an upgrade to an nitrogen

    Roy Cutrer Jr Laer Realty Partners

    15 Goah Way, Vineyard Haven, MA 02568
  • /39

    $3,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,068 Sq Ft

    241 Daggett Ave, Vineyard Haven, MA 02568

    Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    241 Daggett Ave, Vineyard Haven, MA 02568
  • /23

    $3,100,000

    • 1 Bed
    • 1 Bath
    • 1,250 Sq Ft

    114 Meeting House Way, Edgartown, MA 02539

    3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach

    Rose Ryley Wallace & Co. Sotheby's International Realty

    114 Meeting House Way, Edgartown, MA 02539
  • /25

    $1,950,000

    • 2 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    378 State Rd, Vineyard Haven, MA 02568

    MIXED USE PROPERTY WITH PROFESSIONAL OFFICES AND TWO-BEDROOM APARTMENT - Extensively renovated mixed-use property offering commercial + residential use in a high-visibility location on State Road in Tisbury. This versatile property presents a true live-work opportunity with strong income-producing potential.The first floor offers four offices including a reception area, 1.5 baths, and a

    Lesley Heidt Sandpiper Realty Inc

    378 State Rd, Vineyard Haven, MA 02568
  • /19

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,164 Sq Ft

    3 Kims Way, Oak Bluffs, MA 02557

    Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    3 Kims Way, Oak Bluffs, MA 02557
  • /12

    $610,000

    • 2 Beds
    • 1 Bath
    • 705 Sq Ft

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

    Here is your chance to be a Homeowner on Martha's Vineyard. MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that

    Michele Moore Island Real Estate

    124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
  • /40

    $7,350,000

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

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535

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