Edgartown, MA Homes

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  /23

  $8,995,000

  • 11 Beds
  • 8.5 Baths
  • 6,289 Sq Ft

  1 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 this 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

  (508) 715-8610

  1 Louis Field Rd, Edgartown, MA 02539
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  /41

  $8,750 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • House for Rent

  11 High Meadow Ln, Vineyard Haven, MA 02568

  **SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 High Meadow Ln, Vineyard Haven, MA 02568
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  /23

  $1,575,000 Sold Nov 24, 2025

  • 1,666 Sq Ft
  • $945/SF
  • 223 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1997

  60 Windsor Dr, Edgartown, MA 02539

  Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  60 Windsor Dr, Edgartown, MA 02539
• 

  

  

  /17

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 279 Sq Ft

  15 Mill St Unit 31F, Edgartown, MA 02539

  15 Mill St Unit 31F, Edgartown, MA 02539
• 

  

  

  /37

  $9,995,000

  • 6 Beds
  • 7.5 Baths
  • 7,205 Sq Ft

  25 Lelands Path, Edgartown, MA 02539

  Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

  

  Wendy Harman

  Compass

  (508) 625-9706

  25 Lelands Path, Edgartown, MA 02539
• 

  

  /27

  $21,700 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,168 Sq Ft
  • House for Rent

  97 3rd St N, Edgartown, MA 02539

  YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

  Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

  97 3rd St N, Edgartown, MA 02539
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  /48

  $4,750,000 Sold Nov 21, 2025

  • 4,131 Sq Ft
  • $1,150/SF
  • 84 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  36 Crocker Dr, Edgartown, MA 02539

  Stunning Katama Retreat ~ Welcome to this newly constructed architectural gem, nestled on half an acre in the heart of Katama. Perfectly positioned just blocks from the Field Club, close to South Beach, the bike path, and Edgartown Village, this home offers the ultimate indoor-outdoor Martha's Vineyard lifestyle. The elegant entryway sets the tone, leading into a spectacular vaulted living room

  Stephanie Roache Donnelly + Co.

  36 Crocker Dr, Edgartown, MA 02539
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  /36

  Est $2,458,974 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  28 Woodhaven Dr, Edgartown, MA 02539

  28 Woodhaven Dr, Edgartown, MA 02539
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  /42

  $5,995,000

  • 3 Beds
  • 6 Baths
  • 3,608 Sq Ft

  385 Barnes Rd, Vineyard Haven, MA 02568

  Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

  

  Wendy Harman

  Compass

  (508) 205-8817

  385 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /22

  $20,000 total monthly price

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  55 Samoset Ave, Oak Bluffs, MA 02557

  Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  55 Samoset Ave, Oak Bluffs, MA 02557
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  /10

  $3,867,650 Sold Nov 21, 2025

  • 3,000 Sq Ft
  • $1,289/SF
  • 65 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2004

  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 International Realty

  160 Katama Rd, Edgartown, MA 02539
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  /37

  Est $3,590,044 Not Listed For Sale

  • 3 Beds
  • 5 Baths
  • 4,417 Sq Ft

  149 Litchfield Rd, Edgartown, MA 02539

  149 Litchfield Rd, Edgartown, MA 02539
• 

  

  /41

  $5,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,643 Sq Ft

  4 Somerset Ln, Edgartown, MA 02539

  EXPERIENCE BAREFOOT ELEGANCE AT SOMERSET. Welcome to 4 Somerset Lane, a newly completed luxury residence in Edgartown’s exclusive Somerset enclave—perfectly positioned between the charm of Edgartown Village and the surf and sand of South Beach. Developed by Stanmar, owners of the renowned Winnetu Oceanside Resort, this exceptional home embodies the essence of modern coastal living—combining

  

  Wendy Harman

  Compass

  (508) 715-9594

  4 Somerset Ln, Edgartown, MA 02539
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  /29

  $11,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  29 Mercier Way, Edgartown, MA 02539

  **SUMMER RATE$ 9,500-$11,000 WEEKLY** Freshly remodeled 4 bed, 2 full bath coastal cape with all new furnishings, flawless finishes, large private yard, close to South Beach, bike path and downtown Edgartown. Large family room with vaulted ceiling and large TV , gorgeous kitchen with all new stainless appliances, vaulted ceilings, sky lights, custom blue stone countertop, island eatery, and wine

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  29 Mercier Way, Edgartown, MA 02539
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  /42

  $3,075,000 Sold Nov 21, 2025

  • 3,159 Sq Ft
  • $973/SF
  • 157 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1979

  3 Down Harbor Rd, Edgartown, MA 02539

  Exceptional Opportunity in Down HarborRare chance to own in Edgartown’s exclusive Down Harbor community, known for its serene setting and access to Katama Bay. Enjoy deeded rights to a pristine sandy association beach, plus coveted mooring and dock privileges—benefits usually reserved for waterfront estates. This peaceful neighborhood is experiencing a wave of elegant new builds and renovations,

  Susie Wallo Compass

  3 Down Harbor Rd, Edgartown, MA 02539
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  /37

  Est $1,464,307 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft

  12 Fairway Dr, Oak Bluffs, MA 02557

  12 Fairway Dr, Oak Bluffs, MA 02557
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  /34

  $2,250,000

  • 6 Beds
  • 2.5 Baths
  • 1,666 Sq Ft

  34 Massasoit Ave, Oak Bluffs, MA 02568

  Downtown Oak Bluffs an investment opportunity awaits at the top of Circuit Ave. Dual zoned this is two properties in one. An existing 6 bedroom 3.5 bath Victorian home in the popular Copeland District a couple blocks to the beach even closer to restaurants shops and entertainment. On town sewer it's ideal for weekly rentals. The other side of the property facing Circuit Ave. is zoned Commercial

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 715-8624

  34 Massasoit Ave, Oak Bluffs, MA 02568
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  /30

  $28,500 total monthly price

  • 9 Beds
  • 6.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  9 Tuckernuck Ave, Oak Bluffs, MA 02557

  **SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  9 Tuckernuck Ave, Oak Bluffs, MA 02557
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  /42

  $3,695,000 Sold Nov 20, 2025

  • 2,500 Sq Ft
  • $1,478/SF
  • 40 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  37 Road To the Plains, Edgartown, MA 02539

  Exceptional Opportunity to Create Your Signature Vineyard Compound. Behind a charming white picket fence with blooming hydrangeas, this beautifully renovated Edgartown property blends island charm with new construction. Renovated in 2024 by top-tier builders, the nearly new home offers immediate comfort and timeless style, with potential for expansion into a luxury compound. On a private

  Wendy Harman Compass

  37 Road To the Plains, Edgartown, MA 02539
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  /38

  Est $975,891 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  287 County Rd, Vineyard Haven, MA 02568

  287 County Rd, Vineyard Haven, MA 02568
• 

  

  /20

  $1,100,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

  Welcome to this spacious and well-appointed home offering 2,128 square feet of comfortable living space, nestled on a generous 0.49-acre lot. Perfect for both everyday living and entertaining, this residence features beautiful hardwood floors throughout the first floor, with wall to wall carpet in the second floor bedrooms adding warmth and timeless appeal. The large open-concept kitchen is the

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 827-6851

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
• 

  

  /10

  $20,000 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • House for Rent

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

  Karen Overtoom Karen M. Overtoom R.E.

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
• 

  

  /39

  $2,495,000 Sold Nov 20, 2025

  • 2,694 Sq Ft
  • $926/SF
  • 161 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 2016

  16 Mockingbird Dr, Edgartown, MA 02539

  Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious

  Emma Kennedy Sandpiper Realty Inc

  16 Mockingbird Dr, Edgartown, MA 02539
• 

  

  /17

  Est $1,518,651 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,298 Sq Ft

  19 Quantapog Rd, Vineyard Haven, MA 02568

  19 Quantapog Rd, Vineyard Haven, MA 02568
• 

  

  /42

  $2,695,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,001 Sq Ft

  2 Orchard Ln, Edgartown, MA 02539

  Nestled just a short stroll from all the best of Edgartown Village, this beautifully renovated retreat offers the ideal balance of Vineyard charm and modern convenience. Designed across three levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, or hosting guests. The main floor welcomes you with an inviting living room and a custom bar

  

  Wendy Harman

  Compass

  (508) 978-1599

  2 Orchard Ln, Edgartown, MA 02539
• 

  

  /12

  $5,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

  Karen Overtoom Karen M. Overtoom R.E.

  2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
• 

  /2

  $1,350,000 Sold Nov 20, 2025

  • 1,560 Sq Ft
  • $865/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  1 Ambers Way, Edgartown, MA 02539

  This custom three-bedroom post-and-beam home captures the rustic charm and natural beauty of Chappaquiddick. Thoughtfully designed with light-filled spaces and a wood-burning fireplace, the home offers a warm and inviting retreat in every season. A spacious workshop, perfect for the avid outdoorsman, ideal for storing boating, fishing, and woodworking gear. Set on nearly four private acres, the

  Katherine Donahue Sandpiper Realty Inc

  1 Ambers Way, Edgartown, MA 02539
• 

  

  /14

  Est $971,167 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  51 Manchester Ave, Vineyard Haven, MA 02568

  51 Manchester Ave, Vineyard Haven, MA 02568
• 

  

  /42

  $1,498,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,105 Sq Ft

  10 Peases Point Way N, Edgartown, MA 02539

  ICONIC EDGARTOWN VILLAGE BEAUTY with elevated style just one block from Main Street! Recent renovations and upgrades give this 1840's classic a fresh and modern vibe for easy maintenance in-town living. Gracious bluestone terrace bordered with hydrangeas provides a private and serene setting for outdoor living and entertaining. Other notable features include: 3-minute walk to the heart of Main

  

  Wendy Harman

  Compass

  (508) 691-7503

  10 Peases Point Way N, Edgartown, MA 02539
• 

  

  /8

  $13,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Condo for Rent

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

  Karen Overtoom Karen M. Overtoom R.E.

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
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  /46

  $12,500,000 Sold Nov 20, 2025

  • 8,912 Sq Ft
  • $1,403/SF
  • 223 Days On Market

  • 8 Beds
  • 7.5 Baths
  • Built 2008

  30 Crackatuxet Cove Rd, Edgartown, MA 02539

  This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive

  Gerrett Conover Landvest MV

  30 Crackatuxet Cove Rd, Edgartown, MA 02539
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  /45

  Est $1,706,944 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  38 Edgewood Dr, Edgartown, MA 02539

  38 Edgewood Dr, Edgartown, MA 02539
• 

  

  /29

  $1,395,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  42 Road To the Plains, Edgartown, MA 02539

  Classic Colonial - Located between Edgartown Village and Katama, this classically styled colonial features plenty of traditional charm as well as a world of possibilities for renovations and/or expansion. The main entrance opens up to a center staircase flanked by a formal Living Room and Dining Room and there is also a kitchen with breakfast bar PLUS a first-floor bedroom and full bath. The

  

  Wendy Harman

  Compass

  (508) 978-3864

  42 Road To the Plains, Edgartown, MA 02539
• 

  

  /26

  $7,000 total monthly price

  • 7 Beds
  • 1.5 Baths
  • 2,900 Sq Ft
  • House for Rent

  39 N Neck Rd, Edgartown, MA 02539

  Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

  Charles Petitti Coldwell Banker Realty - Newton

  39 N Neck Rd, Edgartown, MA 02539
• 

  /2

  $3,200,000 Sold Nov 18, 2025

  • 960 Sq Ft
  • $3,333/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1966

  23 Manaca Hill Rd, Edgartown, MA 02539

  Enjoy dynamic, panoramic views from this charming and thoughtfully updated single-story Chappaquiddick cottage. Designed for effortless living, the home features an expansive deck overlooking the outer harbor and iconic lighthouse, perfect for entertaining or relaxation. A rooftop observation area provides additional seating and even more breathtaking vistas. Deeded beach access is conveniently

  Katherine Donahue Sandpiper Realty Inc

  23 Manaca Hill Rd, Edgartown, MA 02539
• 

  

  /41

  Est $2,541,338 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  53 Peases Point Way N, Edgartown, MA 02539

  53 Peases Point Way N, Edgartown, MA 02539
• 

  

  /42

  $10,995,000 Pending

  • 7 Beds
  • 3.5 Baths
  • 2,957 Sq Ft

  117 N Water St, Edgartown, MA 02539

  Classic Captain's Home With Deep Water Dock On Edggatown Harbor - Located on prestigious North Water Street in the heart of historic Edgartown Village, this premier harbor front home combines the best of in-town and waterfront living, with deep water dock. On the harbor front side of the home, there are 2 decks with panoramic views across the harbor. There are a total of 7 Bedrooms making the

  

  Wendy Harman

  Compass

  (508) 715-6592

  117 N Water St, Edgartown, MA 02539
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  /6

  $6,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,213 Sq Ft
  • House for Rent

  16 Majors Cove Ln, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Light and spacious home in Major's Cove. Privacy, sunshine, spacious deck out back. Nicely maintained and convenient to all down island towns. Close to Oak Bluffs and Edgartown. Nestled privately in the Major's Cove association, this house is filled with light. It has cathedral ceilings in the living room, a gourmet kitchen open to a dining area or

  Karen Overtoom Karen M. Overtoom R.E.

  16 Majors Cove Ln, Edgartown, MA 02539
• 

  

  /34

  $3,746,925 Sold Nov 14, 2025

  • 2,861 Sq Ft
  • $1,310/SF
  • 114 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1974

  39 Sengekontacket Rd, Edgartown, MA 02539

  SPECTACULAR WATERFRONT home with stunning water views from every room. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. Completely renovated in 2014. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four

  Jayne Isford Ocean Park Realty Inc

  39 Sengekontacket Rd, Edgartown, MA 02539
• 

  

  /38

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  56 Pinehurst Rd, Edgartown, MA 02539

  56 Pinehurst Rd, Edgartown, MA 02539

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