Dukes, MA Homes

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  /21

  $1,795,000

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  9 Brunswick Ave, Oak Bluffs, MA 02557

  PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

  

  Alice Pierce

  Coldwell Banker Realty - Hingham

  (870) 917-0672

  9 Brunswick Ave, Oak Bluffs, MA 02557
• 

  Explore Oak Bluffs

• 

  

  

  /41

  $8,750 per month

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

  11 High Meadow Ln, Vineyard Haven, MA 02568

  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 full bath, plus additional half bath on main level. The

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 High Meadow Ln, Vineyard Haven, MA 02568
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  /41

  $1,850,000 Sold Aug 04, 2025

  • 2,210 Sq Ft
  • $837/SF
  • 22 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  26 Tia Anna Ln, Oak Bluffs, MA 02557

  Welcome to 26 Tia Anna Lane! This exquisite residence is immaculate, stylish, and fully renovated, ready to welcome its new owners! Situated on a beautifully landscaped 0.30-acre lot adorned with vibrant plantings, the home boasts pristine conditions both inside and out, featuring newer Hardi Plank siding. The inviting farmer's porch, complete with Mahogany decking, sets the tone for this

  Marilyn Moses Ocean Park Realty Inc

  26 Tia Anna Ln, Oak Bluffs, MA 02557
• 

  

  

  /3

  Est $1,537,478 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  18 Towanticut Ave, Oak Bluffs, MA 02557

  18 Towanticut Ave, Oak Bluffs, MA 02557
• 

  

  

  /42

  $5,995,000 Open House 8/17

  • 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) 274-5363

  385 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /20

  $14,000 per month

  • 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
• 

  

  /22

  $1,000,000 Sold Jul 31, 2025

  • 768 Sq Ft
  • $1302/SF
  • 96 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  130 Wing Rd, Oak Bluffs, MA 02557

  This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're driving, biking or relying on public transportation to restaurants, shops, beaches, bike paths and

  Lynn Buder Sandpiper Realty Inc

  130 Wing Rd, Oak Bluffs, MA 02557
• 

  

  /21

  Est $1,103,311 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  10 Lagoon Rd, Oak Bluffs, MA 02557

  10 Lagoon Rd, Oak Bluffs, MA 02557
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  /32

  $985,000

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

  Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 514-5238

  37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
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  /30

  $28,500 per month

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

  9 Tuckernuck Ave, Oak Bluffs, MA 02557

  **PEAK SUMMER WEEKLY RATE** 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 distinctive design.

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  9 Tuckernuck Ave, Oak Bluffs, MA 02557
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  /32

  $899,000 Sold Jul 11, 2025

  • 955 Sq Ft
  • $941/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1871

  8 Rock Ave, Oak Bluffs, MA 02557

  Experience the charm of this exquisitely renovated Victorian Gingerbread Cottage, nestled within the historic Martha's Vineyard Camp Meeting Association. Just moments away from Oak Bluffs Harbor, ferry terminals, art galleries, restaurants, public beaches, and vibrant shopping areas, this cottage offers an unparalleled location next to all of Oak Bluffs' picturesque parks.This rare gem

  Marilyn Moses Ocean Park Realty Inc

  8 Rock Ave, Oak Bluffs, MA 02557
• 

  

  /31

  Not Listed For Sale

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

  12 Fairway Dr, Vineyard Haven, MA 02568

  12 Fairway Dr, Vineyard Haven, MA 02568
• 

  

  /24

  $935,000

  • 1 Bed
  • 1 Bath
  • 797 Sq Ft

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

  Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 422-4131

  37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
• 

  

  /10

  $20,000 per month

  • 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
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  /22

  $975,000 Sold Jul 07, 2025

  • 940 Sq Ft
  • $1037/SF
  • 61 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2025

  128 Manchester Ave, Oak Bluffs, MA 02568

  This delightful, modern cape-style home features thoughtful and impressive finish details. The covered porch welcomes you into the home where you will find well-appointed spaces. The kitchen has stainless appliances including a 5-burner gas range with pot filler, an LG French-door refrigerator and dishwasher. The kitchen area is finished with shiplap. There is an open dining and living area with

  Michele Moore Island Real Estate

  128 Manchester Ave, Oak Bluffs, MA 02568
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  /37

  Est $1,519,629 Not Listed For Sale

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

  12 Fairway Dr, Oak Bluffs, MA 02557

  12 Fairway Dr, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /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
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  /29

  $1,100,000 Sold Jun 27, 2025

  • 1,976 Sq Ft
  • $557/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  10 Kims Way, Oak Bluffs, MA 02557

  Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

  Michael Schweikert Ocean Park Realty Inc

  10 Kims Way, Oak Bluffs, MA 02557
• 

  

  /38

  Est $1,055,023 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
• 

  

  /45

  $1,250,000

  • 2 Beds
  • 3 Baths
  • 1,500 Sq Ft

  70 Carol Ln, Oak Bluffs, MA 02557

  Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 456-5742

  70 Carol Ln, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /32

  $1,100,000 Sold Jun 27, 2025

  • 1,976 Sq Ft
  • $557/SF
  • 156 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1985

  10 Kims Way, Oak Bluffs, MA 02568

  Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

  Michael Schweikert Ocean Park Realty, Inc.

  10 Kims Way, Oak Bluffs, MA 02568
• 

  

  /17

  Est $1,551,966 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
• 

  

  /22

  $1,250,000

  • 2 Beds
  • 1 Bath
  • 742 Sq Ft

  47 Winemack St, Oak Bluffs, MA 02557

  Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 403-9601

  47 Winemack St, Oak Bluffs, MA 02557
• 

  

  /25

  $24,000 per month

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • House for Rent

  5 Laurel Ave, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage decor and beautiful bamboo floors. Entertainment options include

  Karen Overtoom Karen M. Overtoom R.E.

  5 Laurel Ave, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /12

  Est $1,307,200 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft

  3 Carole Ave, Vineyard Haven, MA 02568

  3 Carole Ave, Vineyard Haven, MA 02568
• 

  

  /32

  $1,550,000

  • 4 Beds
  • 2 Baths
  • 1,304 Sq Ft

  11 John Wesley Ave, Oak Bluffs, MA 02568

  East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 682-5574

  11 John Wesley Ave, Oak Bluffs, MA 02568
• 

  

  /30

  $20,000 per month

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

  Karen Overtoom Karen M. Overtoom R.E.

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557
• 

  

  /17

  $700,000 Sold Jun 20, 2025

  • 725 Sq Ft
  • $966/SF
  • 111 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1870

  2 Fisk Ave, Oak Bluffs, MA 02557

  Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling,

  Julie Walker Century 21 North East

  2 Fisk Ave, Oak Bluffs, MA 02557
• 

  

  /13

  Est $1,234,075 Not Listed For Sale

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

  33 Menahan St, Vineyard Haven, MA 02568

  33 Menahan St, Vineyard Haven, MA 02568
• 

  

  /28

  $1,950,000

  • 4 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Upper Meadow Ln, Oak Bluffs, MA 02557

  Tucked at the end of a quiet cul-de-sac in the desirable Meadow View Farms neighborhood, this spacious Colonial offers over 3,200 square feet of comfortable and inviting living space. This home is ideal for those who love to host lively gatherings while providing comfortable accommodations for all. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary

  Lesley Heidt Sandpiper Realty Inc

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
• 

  

  /14

  $14,200 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
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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
• 

  

  /31

  Est $1,461,908 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  48 Puritan Dr, Vineyard Haven, MA 02568

  48 Puritan Dr, Vineyard Haven, MA 02568
• 

  

  /40

  $1,925,000

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

  Nora Jardin Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
• 

  

  /15

  $21,000 per month

  • 6 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • House for Rent

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

  Karen Overtoom Karen M. Overtoom R.E.

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
• 

  

  /28

  $1,270,000 Sold May 23, 2025

  • 2,192 Sq Ft
  • $579/SF
  • 57 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  60 Prospect Ave, Oak Bluffs, MA 02557

  OAK BLUFFS ~ APPROVED 4 BEDROOM SEPTIC IN PLACE - This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan. The main level displays beautiful hardwood

  Marilyn Moses Ocean Park Realty Inc

  60 Prospect Ave, Oak Bluffs, MA 02557
• 

  

  /34

  Est $1,241,357 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  38 Lake St, Vineyard Haven, MA 02568

  38 Lake St, Vineyard Haven, MA 02568

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