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18 Henry Hough Lane Chilmark MA 02535
Sold

Listing Id 34988

  • Residential
  • Mls Status Closed
  • Village South
  • Bedrooms 4
  • Bathroom 4

A Large commanding residence set hilltop off Middle road with outstanding water views of the Atlantic and glimpses of Chilmark Pond. Inviting common room with cathedral ceilings, fireplace and gourmet kitchen seamlessly flows to the screened porch and lounging deck. Each wing of the house is comprised of a master bedroom en-suite including two additional bedrooms with private baths. Whether spread out in the family/media room, deck or porch this expansive home can accommodate the largest of families. Special and private with access a short walk away to Fulling Mill Brook Preserve offering 60 acres of walking trails

Listed by Rebecca V Conroy of Conroy & Company R.E.,Inc.

Listing Sold by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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99 Cooke Street Edgartown MA 02539

Edgartown, MA99 Cooke Street

Sale Price$2,135,000

Sold

Listing Id 37794

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 4
  • Bathroom 4.5

LUXURIOUS COTTAGE-STYLE LIVING - WITH ROOM FOR A POOL! Opportunity abounds with this charming cottage-style home in the heart of Edgartown Village. The welcoming porch and French door entry open to a dramatic two-story foyer and open-designed Living/Dining/Kitchen area with gleaming hardwood floors, tasteful accents and a nicely appointed kitchen with classic white cabinets, stone countertops and stainless appliances. French doors open from the Dining area out to a gracious brick terrace and private fenced backyard, ideal for outdoor living and dining. There are a total of FOUR BEDROOMS, each with full bath, including a first-floor Owner's Suite with full en suite bath and French doors that open out to the large mahogany porch and deck. The partially finished Lower Level includes an additional 540-sf of finished space including the 4th bedroom/bonus room with legal egress, a full bath and a separate laundry/utility room. This wonderful in-town cottage LIVES LARGE with over 2,000-s.f. of living space perfectly designed for indoor-outdoor living. There is established rental history with strong recurring demand - plus potential to boost rental income to $125,000+/year with the addition of a SWIMMING POOL (there is a pool permit already in-hand). Furnishings and contents are available separately for a turnkey purchase opportunity. This charming home is a perfect in-town residence or investment property - make it yours!

Listed by Wendy Harman of Compass | Point B

Listing Sold by Compass | MV Team

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 Majors Cove Lane Edgartown MA 02539
Sold

Listing Id 39418

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.56

Major's Cove - A great neighborhood with water views, tennis and pond access! An expanded Cape, traditional in style, with three guest bedrooms and a first floor primary bedroom with en-suite bath, laundry and lots of closets. With over 3,000 sf of living space, there are lots of additional rooms, both formal and informal on two floors. A large sunny deck spans the water side of the home and an oversize garage stores an island car or bikes and toys. This private and peaceful property not only has views of a small fresh water pond, Majors Cove and Sengekontacket Pond but the privacy and natural beauty of the site are further enhanced by hundreds of acres of adjacent Felix Neck Wildlife Trust land.

Listed by Courtney Marek of Sandpiper Realty

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Old Squaw Circle Edgartown MA 02539
Sold

Listing Id 41900

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 0.63

ISLAND GROVE Edgartown. PRISTINE condition and GENEROUS spaces will surprise and impress! With ease of location, systems and well planned areas this expanded home offers abundant lifestyle comforts. Set back from the street, with a welcoming front entrance that reveals years of care and attention to details - blending luxury and coziness. RECENT UPGRADES include; Central AC, new windows, plantation shutters throughout, oak flooring on both levels, new exterior doors including rear slider to the expanded deck. This FOUR bedroom year 'round property is serviced by town water and town sewer allowing for permitted expansion up to 6 bedrooms. The 2019 built garage and rear patio balances this delightful offering. Front to back there's a lot to love about this Island Grove home with easy access to KATAMA, South shore beaches, Edgartown village as well as up island along the West Tisbury Road. Nearby amenities capture foodies and outdoor adventurers alike; Morning Glory Farm stand, Katama General Store - plus conservation trails, hikes and endless bike paths await you. Welcome Summertime with this outstanding offering!

Listed by Helena Kirschenbaum of Compass | MV Team

Listing Sold by Donnelly + Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Sengekontacket Road Oak Bluffs MA 02557
Sold

Listing Id 42694

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.2

Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main level features a living area with a wood-burning fireplace, a spacious kitchen, and a screened-in porch with cathedral ceilings, perfect for dining while enjoying the beautiful views. The primary suite is situated on the second floor and boasts French doors that open to a small deck, allowing you to take in the expansive scenery. The lower level includes three bedrooms, each with French doors leading to a lower deck, and they share a full bathroom. The Sengekontacket Association, established in 1971, encompasses 93 acres and provides a variety of amenities, including tennis and pickleball courts, an Association Clubhouse situated on Wiggy's Pond, and a boat ramp with kayak storage on Sengekontacket Pond. Homeowners can consult the Harbor Master for a mooring in Major's Cove, where the Association dock is located. Fully renovated in 2007, this property is ready for you to enjoy! Furnishings negotiable.

Listed by Cassie Courtney of Wallace & Co. Sotheby's

Listing Sold by Donnelly + Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6 Church Street Aquinnah MA 02535

Aquinnah, MA6 Church Street

Sale Price$2,120,000

Sold

Listing Id 43166

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 2.1

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 Aquinnah and the ocean beyond. Two bedrooms share a full bath, and the primary ensuite bedroom completes this level. Descend to the newly finished lower level, which features a lovely media room, an office, and additional sleeping space. Enjoy multiple outdoor spaces, including a spacious deck perfect for outdoor dining and entertaining, a rooftop deck, (or a "crow's nest,") where you can take in 180-degree views of the Atlantic and breathtaking sunsets, and a new private patio accessible through sliding doors on the lower level. This design allows for three levels of outdoor enjoyment. The home is equipped with central air conditioning and is conveniently located less than a mile from Philbin Beach. You can easily stroll, bike, or drive to the town parking lot just minutes away.

Listed by Heidi Vanderhoop 508-954-5061 of Tea Lane Associates

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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78 Pine Street Edgartown MA 02539

Edgartown, MA78 Pine Street

Sale Price$2,107,000

Sold

Listing Id 38942

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.23

LIKE NEW Five years young expanded Cape located a short walk into town, convenient to all Village amenities: restaurants, shops, groceries, churches, and harbor. The home features quality construction, a bright open floor plan with cathedral ceilings, hardwood floors, central air, four bedrooms, including a first floor Master suite, a second floor Master suite, and two additional second floor guest bedrooms, three and a half baths, a gourmet kitchen with center island, stainless appliances, and granite counters, living room with gas fireplace, full basement, outside deck and shower, and a nicely landscaped , private yard.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11 Brown Road Edgartown MA 02539

Edgartown, MA11 Brown Road

Sale Price$2,100,000

Sold

MLS Number 38996

  • Land
  • Mls Status Closed
  • Acreage 3.04

A beautiful 3 acre building lot nestled between farm fields and forest where privacy and nature abound. The parcel supports up to five bedrooms either in one home or inclusive of a guest house after five years plus outbuildings. Some nearby parcels are substantial in size and have conservation restrictions limiting development. Superbly located with close proximity to South Beach, Morning Glory Farm and Wilson's Landing on the Edgartown Great Pond for kayaking or boating to the barrier beach.

Listed by Sandpiper Realty

Listing Sold by Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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441 State Road Vineyard Haven MA 02568
Sold

MLS Number 35663

  • CommercialSale
  • Mls Status Closed
  • Village Central
  • Bathroom 3
  • Bedrooms 4

POTENTIAL! POTENTIAL! POTENTIAL! in this mixed-use Commercial/Residential Building. Opportunity to own almost 3,000 sq. ft. of retail space PLUS two-2 bedroom apartments PLUS lots of storage PLUS ample parking in the front and rear of the building. Currently the home of Vineyard Auto on the lower level, this part of the building will be sold empty. There are TWO -two bedroom apartments on the second level. The left side apartment features two spacious bedrooms, open living and kitchen area and full bath. The right side apartment features two more bedrooms and full bath. Separate laundry area in hall with two washers and two dryers, office area and another room with separate bath. The septic is for an actual bedroom count of 4 bedrooms. There is separate garage space in the back of the building as well. The electric meter is for the store as well as the apartments- one meter. Any further information about changes to the property should be collected from the town Building Inspector, Board of Health, Zoning and any other departments necessary.

Listed by Nora Jardin of Island Real Estate

Listing Sold by Ezra Sherman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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48 Main Street Vineyard Haven MA 02568
Sold

MLS Number 37486

  • CommercialSale
  • Mls Status Closed
  • Village Downtown
  • Bathroom 3
  • Bedrooms 2

MULTI-GENERATIONAL ISLAND BUSINESS WITH THREE DOWNTOWN LOCATIONS The sale of these three commercial buildings includes all rights to Mad Martha's Ice Cream, which celebrated its 50th year in business this year. All three buildings are in excellent turnkey condition. This modern multi-use building is located in the middle of Main Street Vineyard Haven. Built in 2009, it boasts a basement kitchen as well as two income producing apartments above the main floor. The third floor studio has a spacious roof deck providing views of the harbor. Each apartment has their own separate entrance off the back of the building. Please refer to these links to view information about the other two buildings included in the sale: 7 North Water Street Edgartown - http://vineyard.mylinkmls.com/MyListings/37484 12 Circuit Avenue Oak Bluffs - http://vineyard.mylinkmls.com/MyListings/37485

Listed by Jared Bicknell of Feiner Real Estate

Listing Sold by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10 Paddock Road Oak Bluffs MA 02575

Oak Bluffs, MA10 Paddock Road

Sale Price$2,100,000

Sold

Listing Id 33638

  • Residential
  • Mls Status Closed
  • Village Central
  • Bedrooms 5
  • Bathroom 4.5

4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st and 2nd floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. This is a "family compound in the making," a swimming pool and poolhouse may also be installed if a buyer chooses to do so. With its generous living spaces this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather round at the end of the day.

Listed by Bonnie Pierce of Wallace & Co. Sotheby's

Listing Sold by Priestley Smadbeck & Mone

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Ask A QuestionMore Details

9 Peases Point Road Edgartown MA 02539
Sold

Listing Id 36506

  • Residential
  • Mls Status Closed
  • Village Katama
  • Bedrooms 5
  • Bathroom 6

Welcome to this Edgartown Family Compound which features a spacious colonial that was designed with an open floor plan for easy island living. The living room, with a gas fireplace, dining area and large gourmet kitchen lends itself to comfortable entertaining. The kitchen features expansive granite countertops, double ovens, a gas stove top, trash compactor and an additional sitting nook. The great room area leads to an outdoor deck for gathering and grilling. The spacious bedrooms and finished third floor bonus area provides ample sleeping space and areas to gather. The two bedroom guest house which was built in 2006 features a front farmers porch, an additional covered porch off the great room and a lower level blue stone patio for dining and grilling. This property is located close to Katama General Store, Edgartown Village and South Beach. Come experience all that this family compound has to offer.

Listed by Michele Casavant of Vineyard Village Realty

Listing Sold by Vineyard Village Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.47% last updated on Jun 18, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to LINKMV as of June 21, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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