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26 Greenleaf Avenue Oak Bluffs MA 02557
Sold

Listing Id 39529

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 3.5
  • Acreage 0.11

How often do you find a property with three different water views -pond (Sunset Lake), harbor (Oak Bluffs) and ocean (Vineyard Sound). Location is everything, and this bungalow has it all. You can practically hear the children squeal with joy after catching the brass ring at the famous Flying Horses Carousel, and a front row seat on your wrap-around porch for the annual August fireworks. As close as it is to the ferry, beaches, restaurants, shops, and even the public library, this getaway perched on a hill in a quiet neighborhood allows for a peaceful cup of morning coffee on the side patio. Thoughtfully renovated by a popular local architect, this bright and cheery cottage provides plenty of room for multiple guests. Each of the unique 6 bedrooms makes clever use of space and natural light. When you think of a seaside getaway with all the amenities, this is what you picture. And if you want to share, there is a strong rental history.

Listed by Carol McManus of C McManus Realty Group

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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69 Putnam Road Chilmark MA 02535

Chilmark, MA69 Putnam Road

Sale Price$3,500,000

Sold

Listing Id 35860

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

Amazing, dramatic, expansive sunset water view property in the desirable Spring Point Association. Property features a three bedroom main house and a two bedroom, two bath guest house. Sited on 3.6 acres, this association offers deeded, private beach access to Beck's Beach, tennis courts, and walking trails. Main house offers an open floor plan with modern kitchen with pantry, dining area, spacious living room with fireplace, and half bath. Wonderful screened porch off the kitchen that opens onto a new, spacious deck. Two additional patios add great outdoor gathering areas. There is a main level master bedroom with en-suite bathroom, office and access to private deck. The lower level features two additional bedrooms, a full bath, storage area, and spacious garage. The guest house is nicely sited away from the main house and is quite private. There is a large deck, screened porch, living room with fireplace, loft, and two bedrooms each with a private bathroom. In addition, enjoy Lucy Vincent Beach, Squibnocket Beach and all Chilmark has to offer. Quansoo Beach lot also available for separate sale. *square footage of property to be confirmed by town

Listed by Sheila Morse of Island Real Estate

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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25 Harthaven Road Oak Bluffs MA 02557
Sold

Listing Id 39790

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 1.56

Harthaven ~ An opportunity that doesn't come often! An expanded Cape in pristine condition with over 3,500s/f, 4 spacious bedrooms, 3.5 baths, great room, large cook's kitchen, dining area plus cozy den. The location and amenities included in Harthaven are exceptional and especially unique for a down-island property. No longer will finding parking at the beach be an issue as this includes use of an expansive private association Nantucket Sound beach, access to Farm Pond and neighborhood tennis/pickleball courts are steps away. Bike or walk into OB on the path at the entrance of the neighborhood. Privacy, summer amenities and proximity to town make for the ultimate vacation retreat!

Listed by Courtney Marek of Sandpiper Realty

Listing Sold by Ocean Park Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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71,77,79 Edgartown-vineyard Haven Road & 10 Gamba Road Oak Bluffs MA 02557
Sold

Listing Id 40244

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 3
  • Acreage 7.769

4 parcels, 2 with dwellings. Assessments and acreage reflect total of all parcels.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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115 South Water Street Edgartown MA 02539
Sold

Listing Id 38797

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.2137

NEWLY LISTED! VINTAGE CHARMER WITH SECOND-STORY WATER VIEWS. Framed by billowing pink rose bushes, a top-railed picket fence and a crushed shell driveway, the charming antique home offers the epitome of classic in-town living. The interior is teeming with original millwork and built-ins plus two (2) lined fireplaces. The two-story home features French doors that open from the Living Room to a covered porch overlooking the private and beautifully landscaped back yard -- and an added special feature is the second-floor deck with superlative views of Edgartown Harbor and the Lighthouse. The property had significant upgrades in 2014-2015 including a new foundation plus new Andersen® windows, foam insulation, cedar shingle siding -- plus a new HVAC system and backup generator, this sweet antique home is ready to be further transformed with renovation upgrades. There are a total of four bedrooms and three full baths, including a first floor Primary Bedroom, two second-floor bedrooms and a detached bedroom with en suite bath.

Listed by Wendy Harman of Compass | Point B

Listing Sold by The Agency

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$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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156 Winyah Circle Vineyard Haven MA 02568
Sold

Listing Id 41461

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 5.5
  • Acreage 0.4595

(*Turnkey, fully furnished package was sold separately*) With a thoughtful floor plan and beautiful backyard, this custom-built home offers you plenty of space to entertain family and friends. The main level Great Room is the hub of the home. With it's stunning stone fireplace anchoring the living room to the chef's kitchen on the opposite side of the room, the Great Room gives you both casual and formal areas to gather. The dining area is centered in front of French doors with views of the pool and patio. The first floor primary and guest bedroom are both en-suite and are located on opposites wings of the main level. A cozy den, laundry room, pantry, mudroom and powder room finish off the main level. The second floor has a stylish open landing overlooking the main level. Two en suite bedrooms are located on opposites sides of this floor. The finished basement offers you additional living space and a private en suite bedroom. The backyard will be your summer oasis. The focal point of this outdoor space is the heated, gunite, saltwater pool. Many gathering spaces to enjoy around the patio such as the hot tub, gas fire pit and covered seating area. This beautiful, well-appointed home has all the features you're looking for in a Vineyard property.

Listed by Terie Geary of Donnelly + Co

Listing Sold by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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27, 30, 31 Tower Lane; 34 Eben's Lane Chilmark MA 02535
Sold

Listing Id 40432

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 4
  • Acreage 67.2

PRICE CHANGE reflects the addition of 3.9 acres to the existing listing. Large estate in Chilmark. As you turn off of Middle Road you are met by a cobblestone driveway that leads you through 7+acres of conservation land and up to the towering Carriage House archway that is the entryway to this majestic property. Emerging through the archway you are greeted by a unique assemblage of structures including the contemporary main house, guest house, and studio. These are surrounded by old stonewalls and newer detailed stonework that creates a harmonious balance between old farmland and new modern design. The Main House contains 4-bedrooms, large open living space and a rooftop deck. The nearby Guest House with 2-bedrooms and full kitchen overlooks raised bed gardens and rolling hills. Also located on the property is another 2-bedroom cottage with a full kitchen and an unfinished pool with pool house. On the far side of the property is over 45 acres of conservation land including portions of the Tiasquam River, all creating the utmost in privacy. There is potential to build one more single-family home on a portion of the property, or simply update the existing structures and enjoy the pristine land that surrounds you. The options for this property are many and varied.

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

Listing Sold by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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5 Puritan Drive Oak Bluffs MA 02557

Oak Bluffs, MA5 Puritan Drive

Sale Price$3,500,000

Sold

Listing Id 42672

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.76

SOLD TURNKEY - Discover this newly built, farmhouse-style residence nestled in the highly desirable Tower Ridge Neighborhood, just moments from downtown Oak Bluffs, with easy access to all other island towns. Offered completely turn-key, this property comes fully furnished, allowing you to settle in immediately and start enjoying its many features. The neighborhood also includes private tennis courts for residents, and proximity to the renowned Farm Neck Golf Club makes this location truly unbeatable. As you arrive, a spacious farmer's porch welcomes you into the meticulously designed home. Step inside to be greeted by walls of windows that frame breathtaking views of the 18x36 pool and attached hot tub, creating a serene backdrop to your everyday living. The inviting living room, complete with a gas fireplace, flows seamlessly into the gourmet kitchen, which is equipped with KitchenAid appliances, including a 6-burner stove, refrigerator, and dishwasher. Quartz countertops, a breakfast bar, and a formal dining area make this space perfect for entertaining. On the main floor, the first primary bedroom offers a luxurious retreat with a king bed and en-suite bath. The second level boasts an additional primary suite with the same level of comfort and elegance, also featuring a king bed and en-suite bath. Two more generously sized bedrooms (4-bedroom maximum) and a versatile den/office space, accessed through a custom steel and glass door by Weldwork, complete the upstairs layout. The finished space above the two-car garage presents endless possibilities-whether as a media room, home gym, or a creative studio. The property also features an outdoor shower and a soon-to-be-completed outdoor kitchen, equipped with premium Hestan appliances, perfect for al fresco dining and summer barbecues. All interior and exterior furniture, except for the bonus room, is by Arhaus, adding a touch of sophistication throughout the home. Blending modern luxury with timeless farmhouse charm, this home provides everything you need for a relaxed and sophisticated island lifestyle. Significant rental history available upon request.

Listed by Jen O'Hanlon of Compass | The O'Hanlon Group

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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339 Lake Street Vineyard Haven MA 02568
Sold

Listing Id 43881

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 1.8

Not listed in link

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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26 Pinkletink Road Chilmark MA 02535

Chilmark, MA26 Pinkletink Road

Sale Price$3,495,000

Sold

Listing Id 39499

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 2
  • Acreage 3

PROSPECT HILL CONTEMPORARY WITH WATER VIEWS. Located off North Road, in the highly-coveted Prospect Hill enclave, this contemporary beach house is set amid a 3-acre natural landscape with rolling fields and perched to enjoy idyllic sunsets and sweeping views across Menemsha Bight to Lobsterville Beach and the Gay Head Lighthouse beyond. The home offers one-level living, designed to maximize the views and indoor-outdoor living with a full wall of sliding glass doors that open out to an expansive 1244-square-foot mahogany deck. The home has been tastefully updated and features beautiful hardwood floors, a wood-burning fireplace, automatic Hunter Douglas® blinds, high-end kitchen appliances, central air, smart home technology with Nest® thermostats and more. Prospect Hill offers private association tennis courts and there is easy access to Menemsha Village plus other favorites like Great Rock Bight Preserve, Menemsha Hills, The Brickyard and more. Note: There is future expansion potential and preliminary plans to site a guest house and pool are available. The property is being offered turnkey with furnishings and contents, making it move-in ready for Summer, 2022. ***OPEN HOUSES are scheduled between 1:00 PM and 3:00 PM on Saturday, 4/23 and Sunday, 4/24***. The Sellers will begin accepting offers at 5:00 PM on Monday, 4/25.

Listed by Wendy Harman of Compass | Point B

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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33 Old Oklahoma Road Vineyard Haven MA 02568
Sold

Listing Id 41300

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.7464

Magnificent is the word that best describes this meeting of nature, with this stunning, shimmering Lagoon vista, and human skill and ingenuity reflected in the craftsmanship of the 2016 complete renovation. You are right at water's edge, with your own private beach area. This home sits high enough to take advantage of the commanding views down the Lagoon toward the drawbridge. It is built on two levels: the kitchen, dining and living rooms on the lower level and the bedrooms on the upper level. The home is all-electric, featuring three bedrooms and three full baths and a recently built two-car garage with solar shingles and a full basement. There are granite stairs leading to ample deck areas, all with spectacular views, and a staircase leading to the beach. The property is being sold mostly furnished. The seller's mooring equipment is included, as well. This is a rare opportunity to obtain a first quality home in a waterfront location.

Listed by Lynn and Karl Buder of Sandpiper Realty

Listing Sold by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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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175 Pond Road West Tisbury MA 02568

West Tisbury, MA175 Pond Road

Sale Price$3,490,000

Sold

Listing Id 38720

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 1.38

Exquisite home with swimming pool in the perfect location in West Tisbury! Set on one of the rarely offered field view parcels in Deep Bottom Pond, this gracious residence in one of the island's most sought after enclaves exudes quality at every turn. Constructed by noted contractor Rosbeck Builders, a rare degree of achievement is on display. Through the front entry, an open and voluminous main living area captivates, with views of the pool, pond and pastures beyond. The front foyer features dramatic 2-story and opens into the home's grand central living room. This gracious gathering place is filled with light from multiple directions and stately wood-burning fireplace. Four bedrooms, home office and 3 and 1/2 baths. There are two master suites one on the first floor and another on the second. Tastefully decorated with artwork from the Louisa Gould Gallery. This home sits on 1.38 acres which gives you breathtaking pasture and pond views all around.

Listed by Lisa Diane Da Silva of Compass | MV Team

Listing Sold by Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 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

Based on information submitted to LINKMV as of June 15, 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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