Dukes, MA Homes

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  /26

  $2,795,000

  • 3 Beds
  • 3 Baths
  • 2,750 Sq Ft

  109 Herring Creek Rd, Edgartown, MA 02539

  Coastal Retreat In Katama - Located in the heart of Katama, with the iconic Katama Airfield and the sandy shores of South Beach nearby, this contemporary coastal retreat is ideal for enjoying all the best of Katama. The reverse-style contemporary features a sunny, open-designed floor plan with vaulted ceilings that seamlessly combine an inviting Living Room with gas fireplace, a Game Room with

  

  Wendy Harman

  Compass

  (508) 274-5363

  109 Herring Creek Rd, Edgartown, MA 02539
• 

  

  

  /20

  $20,000 per month

  • 3 Beds
  • 3 Baths
  • House for Rent

  40 Hidden Cove Rd, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

  Karen Overtoom Karen M. Overtoom R.E.

  40 Hidden Cove Rd, Oak Bluffs, MA 02557
• 

  

  

  /22

  $1,299,000 Sold Jun 25, 2025

  • 1,512 Sq Ft
  • $859/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  2 Boylston Dr, Edgartown, MA 02539

  Edgartown: MOVE IN READY! Stylish 3-bedroom 2 bath home with inviting and charming floor plan integrates comfort and function. Cathedral ceilings with skylight and 2 sets of sliders providing natural light and a bright open floor plan.Updated kitchen with breakfast bar and dining area. 1st Floor bedroom. Full bathroom and spacious living room perfect for gatherings and relaxing. There is

  Martha Smith C McManus Realty Group

  2 Boylston Dr, Edgartown, MA 02539
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  /7

  Not Listed For Sale

  • 4 Beds

  53 N Neck Rd, Edgartown, MA 02539

  53 N Neck Rd, Edgartown, MA 02539
• 

  

  

  /34

  $2,700,000

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

  34 Massasoit Ave, Oak Bluffs, MA 02568

  This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 348-7972

  34 Massasoit Ave, Oak Bluffs, MA 02568
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  /29

  $64,000 per month

  • 4 Beds
  • 7 Baths
  • 3,600 Sq Ft
  • House for Rent

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557
• 

  

  /26

  $1,000,000 Sold Jun 24, 2025

  • 1,202 Sq Ft
  • $832/SF
  • 254 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  17 Meetinghouse Village Way, Edgartown, MA 02539

  KATAMA CONDOMINIUM IN MEETINGHOUSE VILLAGE - A bright and sunny center unit with an open floor plan, vaulted ceilings, skylights, and windows that fill the space with natural light. This home is in excellent condition, showing the pride of ownership. The wide-open kitchen with a breakfast bar offers a wonderful space for cooking and entertaining. Accommodations include a first-floor bedroom with

  Leslie C. Floyd Portfolio Real Estate, Inc.

  17 Meetinghouse Village Way, Edgartown, MA 02539
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  /14

  Est $5,464,361 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,193 Sq Ft

  100 Meetinghouse Way, Edgartown, MA 02539

  100 Meetinghouse Way, Edgartown, MA 02539
• 

  

  /5

  $2,995,000 Pending

  • Land
  • 3.01 Acres
  • $995,017 per Acre

  9 Turkeyland Cove Rd, Edgartown, MA 02539

  Turkeyland Cove: Three-Acre Estate-Sized Parcel In Katama - This beautiful and private building site is one of the last remaining 3-acre parcels in Katama. The property offers a perfect opportunity to create a signature residence, multi-generational retreat, or equestrian dream, with possibilities for a Main House, Carriage House, pool, tennis court and/or barn. The property offers easy access to

  

  Wendy Harman

  Compass

  (508) 252-8527

  9 Turkeyland Cove Rd, Edgartown, MA 02539
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  /40

  $16,400 per month

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

  20 Katama Bay Rd Ed350, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

  Karen Overtoom Karen M. Overtoom R.E.

  20 Katama Bay Rd Ed350, Edgartown, MA 02539
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  /7

  $600,000 Sold Jun 23, 2025

  • Land
  • 0.50 Acre
  • $1,200,000 per Acre

  • 4 Days On Market

  27 7th St N Unit 198, Edgartown, MA 02539

  This .5-acre lot is located in a favorable Edgartown neighborhood with proximity to the bike path, public transportation, and close to town. The property has been staked and perc tested, and will support 2 bedrooms with a standard Title V septic system or 3 bedrooms with an advanced treatment system. Information should be verified by the Edgartown Board of Health Department. Embrace the unique

  Stephanie Roache Donnelly + Co

  27 7th St N Unit 198, Edgartown, MA 02539
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  /36

  Est $1,735,729 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,122 Sq Ft

  62 Whalers Walk, Edgartown, MA 02539

  62 Whalers Walk, Edgartown, MA 02539
• 

  

  /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
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  /30

  $20,000 per month

  • 4 Beds
  • 3 Baths
  • 2,226 Sq Ft
  • House for Rent

  54 Schoolhouse Road Ed330, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

  Karen Overtoom Karen M. Overtoom R.E.

  54 Schoolhouse Road Ed330, Edgartown, MA 02539
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  /6

  $600,000 Sold Jun 23, 2025

  • Land
  • 0.50 Acre
  • $1,200,000 per Acre

  • 4 Days On Market

  27 7th St N, Edgartown, MA 02539

  This .5-acre lot is located in a very favorable Edgartown neighborhood with proximity to the bike path, public transportation, and close to town. The property has been staked and perc tested, and will support 2 bedrooms with a standard Title V septic system or 3 bedrooms with an advanced treatment system. Information should be verified by the Edgartown Board of Health Department. Embrace the

  Stephanie Roache Donnelly + Co.

  27 7th St N, Edgartown, MA 02539
• 

  

  /36

  Est $3,937,092 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,902 Sq Ft

  94 Marthas Rd, Edgartown, MA 02539

  94 Marthas Rd, 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
• 

  

  /31

  $50,000 per month

  • 5 Beds
  • 5 Baths
  • 2,975 Sq Ft
  • House for Rent

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

  Karen Overtoom Karen M. Overtoom R.E.

  17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
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  /47

  $1,595,500 Sold Jun 23, 2025

  • 1,822 Sq Ft
  • $876/SF
  • 73 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2003

  21 Coffins Field Rd, Edgartown, MA 02539

  EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

  Helena Kirschenbaum Studio Realty

  21 Coffins Field Rd, Edgartown, MA 02539
• 

  

  /20

  Est $1,575,031 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,532 Sq Ft

  39 Prices Way, Edgartown, MA 02539

  39 Prices Way, 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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  /29

  $18,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,027 Sq Ft
  • House for Rent

  12 Cottle Lane Ed341, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

  Karen Overtoom Karen M. Overtoom R.E.

  12 Cottle Lane Ed341, Edgartown, MA 02539
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  /56

  $1,699,000 Sold Jun 20, 2025

  • 2,954 Sq Ft
  • $575/SF
  • 314 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1900

  9 Goode St, Oak Bluffs, MA 02557

  Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedroom, 1-bathroom apartment attached to the home, providing a perfect space for guest accommodation.

  Grace Hagerty Grace Hagerty Real Estate Inc

  9 Goode St, Oak Bluffs, MA 02557
• 

  

  /23

  Est $2,154,681 Not Listed For Sale

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

  31 Pulpit Ln, Edgartown, MA 02539

  31 Pulpit Ln, Edgartown, MA 02539
• 

  

  /42

  $3,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,056 Sq Ft

  9 Thaxter Ln, Edgartown, MA 02539

  Contemporary coastal retreat near South Beach. Just moments from the ocean, this tri-level home on Thaxter Lane offers modern design, indoor-outdoor living, and a saltwater pool. Hear ocean sounds from your deck and enjoy Edgartown living—ideal as a private escape or rental property. The light-filled living room has vaulted ceilings, a wood-burning fireplace, and sliding doors opening to

  

  Wendy Harman

  Compass

  (508) 274-5363

  9 Thaxter Ln, Edgartown, MA 02539
• 

  

  /36

  $56,800 per month

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

  2 Nonamessett Rd, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

  Karen Overtoom Karen M. Overtoom R.E.

  2 Nonamessett Rd, Edgartown, MA 02539
• 

  

  /20

  $821,000 Sold Jun 17, 2025

  • Land
  • 1.40 Acres
  • $586,429 per Acre

  • 0 Days On Market

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

  Large 1.4 Acre Corner lot in Vineyard Meadow Farms South side of West Tisbury Road. Private, flat, level parcel, paved dead end road with no unnecessary through traffic. Six bedrooms, a 3,000SF Main House, a 2,000SF detached/attached Secondary Building allowed per the Town. Pool allowed with standard Special permit. Centrally located to all Island Towns. Great neighborhood. Great location with

  Janna O'Loughlin Portfolio Real Estate, Inc.

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
• 

  

  /48

  Est $2,960,910 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
• 

  

  /42

  $16,975,000

  • 6 Beds
  • 4.5 Baths
  • 3,606 Sq Ft

  111 N Water St, Edgartown, MA 02539

  Historic captain’s home circa 1850, brilliantly renovated by architect Patrick Ahearn in 2002, on coveted North Water Street. Enjoy sweeping 180 Edgartown Harbor views from bright, sunlit living spaces with heart pine floors and custom millwork. An open-concept first floor flows to an 18x29' mahogany deck, perfect for al fresco dining and entertaining. The rare double-wide lot offers a lawn

  

  Wendy Harman

  Compass

  (508) 274-5363

  111 N Water St, Edgartown, MA 02539
• 

  

  /25

  $80,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

  Karen Overtoom Karen M. Overtoom R.E.

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
• 

  

  /18

  $1,219,000 Sold Jun 16, 2025

  • 1,512 Sq Ft
  • $806/SF
  • 99 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  108 Charles Neck Way, Vineyard Haven, MA 02568

  This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

  Alyssa Halisky Wallace & Co. Sotheby's

  108 Charles Neck Way, Vineyard Haven, MA 02568
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  /52

  Est $5,460,636 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,740 Sq Ft

  12 Plantingfield Wood Cir, Edgartown, MA 02539

  12 Plantingfield Wood Cir, Edgartown, MA 02539
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  /48

  $5,495,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 3.5 Baths
  • 4,131 Sq Ft

  36 Crocker Dr, Edgartown, MA 02539

  Stunning Katama Retreat ~ Welcome to this newly constructed architectural gem, nestled on half an acre abutting serene common land 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

  Stephanie Roache Donnelly + Co.

  36 Crocker Dr, Edgartown, MA 02539
• 

  

  /23

  $36,000 per month

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft
  • House for Rent

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

  Karen Overtoom Karen M. Overtoom R.E.

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
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  /42

  $2,400,000 Sold Jun 05, 2025

  • 3,200 Sq Ft
  • $750/SF
  • 49 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 2014

  6 Martha's Park Rd, Oak Bluffs, MA 02557

  Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

  Jennifer B. DaSilva Compass

  6 Martha's Park Rd, Oak Bluffs, MA 02557
• 

  

  /21

  Est $1,585,977 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,583 Sq Ft

  8 Old Purchase Way, Edgartown, MA 02539

  8 Old Purchase Way, Edgartown, MA 02539
• 

  

  /27

  $2,500,000

  • 4 Beds
  • 4 Baths
  • 2,202 Sq Ft

  2 Farmers Rd, Edgartown, MA 02539

  This house and guesthouse combination are situated in a very special location. Located equidistant between town and South Beach. The neighboring properties are quite impressive. Across the lane is over 28 acres of Edgartown Conservation Commission land. The property currently has two dwellings, a three bedroom main house and a one bedroom guesthouse. A separate toolshed has an additional finished

  Neal Stiller Cronigs Real Estate

  2 Farmers Rd, Edgartown, MA 02539
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  /32

  $100,000 per month

  • 5 Beds
  • 4 Baths
  • 4,500 Sq Ft
  • House for Rent

  60 Witchwood Lane Ed317, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $25,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy

  Karen Overtoom Karen M. Overtoom R.E.

  60 Witchwood Lane Ed317, Edgartown, MA 02539
• 

  

  /18

  $3,350,000 Sold Jun 05, 2025

  • 3,156 Sq Ft
  • $1061/SF
  • 138 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1900

  25 Simpson's Ln, Edgartown, MA 02539

  Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The

  Greg Hartel Hartel Realty

  25 Simpson's Ln, Edgartown, MA 02539
• 

  

  /27

  Est $2,201,793 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  1 Gray Gull Cir, Edgartown, MA 02539

  1 Gray Gull Cir, Edgartown, MA 02539

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