Dukes County, MA Homes for Rent

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  $10,000 per month plus fees

  • 6 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  15 Crowell Lane Wt119, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

  Karen Overtoom Karen M. Overtoom R.E.

  15 Crowell Lane Wt119, West Tisbury, MA 02575
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  $46,000 per month plus fees

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

  99 Pond Road Wt104, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

  Karen Overtoom Karen M. Overtoom R.E.

  99 Pond Road Wt104, West Tisbury, MA 02575
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  $12,000 per month plus fees

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  267 Great Plains Road Wt117, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

  Karen Overtoom Karen M. Overtoom R.E.

  267 Great Plains Road Wt117, West Tisbury, MA 02575
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  $10,000 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • House for Rent

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

  Karen Overtoom Karen M. Overtoom R.E.

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
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  $19,000 per month plus fees

  • 6 Beds
  • 2.5 Baths
  • 2,155 Sq Ft
  • House for Rent

  17 Umbagog Ave Wt109, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

  Karen Overtoom Karen M. Overtoom R.E.

  17 Umbagog Ave Wt109, West Tisbury, MA 02575
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  $13,600 per month plus fees

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft
  • House for Rent

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

  Karen Overtoom Karen M. Overtoom R.E.

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
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  $14,500 per month plus fees

  • 5 Beds
  • 5.5 Baths
  • 3,392 Sq Ft
  • House for Rent

  76 School House Lane Wt101, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  $24,000 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • House for Rent

  836 State Rd, Aquinnah, MA 02535

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the sand

  Karen Overtoom Karen M. Overtoom R.E.

  836 State Rd, Aquinnah, MA 02535
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  $3,000 per month plus fees

  • 4 Beds
  • 2.5 Baths
  • 2,703 Sq Ft
  • House for Rent

  41 Oak Lane Wt147, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

  Karen Overtoom Karen M. Overtoom R.E.

  41 Oak Lane Wt147, West Tisbury, MA 02575
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  $11,000 per month plus fees

  • 2 Beds
  • 1.5 Baths
  • 800 Sq Ft
  • House for Rent

  55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. Nestled on a quiet country lane, this charming two BR guest house will enchant you with its inviting character and custom features throughout. From the cathedral living area and newly furnished interior to the covered front porch and expansive deck, this lovely cottage has it all. Privately situated , yet convenient to the village, bike path and local

  Karen Overtoom Karen M. Overtoom R.E.

  55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
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  $10,000 per month plus fees

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

  21 Leona Lane Wt115, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

  Karen Overtoom Karen M. Overtoom R.E.

  21 Leona Lane Wt115, West Tisbury, MA 02575
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  $21,000 per month plus fees

  • 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
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  $10,800 per month plus fees

  • 4 Beds
  • 2 Baths
  • 702 Sq Ft
  • House for Rent

  141 N Rd Ch202, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

  Karen Overtoom Karen M. Overtoom R.E.

  141 N Rd Ch202, Chilmark, MA 02535
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  $30,000 per month plus fees

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • House for Rent

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This stunning sanctuary offers a unique balance of simplicity and sophistication. There is a lot of room for family and friends to enjoy both indoors and out. Nestled about midway between Tisbury and West Tisbury, here you will find yourself close to two of Martha's Vineyard's town centers. Enjoy ping pong in the retro style game room or a fire in the fire pit. This

  Karen Overtoom Karen M. Overtoom R.E.

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575
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  $12,500 per month plus fees

  • 4 Beds
  • 1.5 Baths
  • 1,413 Sq Ft
  • House for Rent

  11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior decor. The wraparound porch has plenty of room to enjoy people watching or sipping ice cold tea, perfect for a hot summer day. Alternatively, you can enjoy peering down the street from the master bedroom which opens up to a charming porch with plenty of room for two to enjoy

  Karen Overtoom Karen M. Overtoom R.E.

  11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557
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  $6,500 per month plus fees

  • 3 Beds
  • 3 Baths
  • 1,645 Sq Ft
  • House for Rent

  23 Ocean Ave Unit OB539, Edgartown, MA 02539

  THIS IS A SUMMER WEEKLY RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This charming beach house is steps away

  Karen Overtoom Karen M. Overtoom R.E.

  23 Ocean Ave Unit OB539, Edgartown, MA 02539
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  $21,000 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,481 Sq Ft
  • House for Rent

  24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568

  THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a

  Karen Overtoom Karen M. Overtoom R.E.

  24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568
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  $20,000 per month plus fees

  • 3 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • House for Rent

  67 New York Ave Unit OB536, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. 1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and

  Karen Overtoom Karen M. Overtoom R.E.

  67 New York Ave Unit OB536, Oak Bluffs, MA 02557
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  $40,000 per month plus fees

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft
  • House for Rent

  38 Farm Pond Ob524, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. Gracious 4 bedroom home with private beach access and tennis. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate studio is attached by the deck. You are a short distance from town, less than a mile to the public beach and a minutes to a beautiful

  Karen Overtoom Karen M. Overtoom R.E.

  38 Farm Pond Ob524, Oak Bluffs, MA 02557
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  $25,000 per month plus fees

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  61 Roadto Greatneck, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This lovely new build house features 3 bedrooms, and 3 bathrooms. There is a full gourmet kitchen, open to the dining, living and patio area. French doors off the living area open up to a beautiful blue stone patio complete with breath taking water views. All three bedrooms are located on the upstairs level including the master suite. Lambert's Cove Beach Access.

  Karen Overtoom Karen M. Overtoom R.E.

  61 Roadto Greatneck, West Tisbury, MA 02575
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  $17,000 per month plus fees

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  196 Vineyard Meadow Farms Wt130, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. Well appointed Farmhouse Colonial, on two private acres on private road. Conveniently located in Vineyard Meadow Farms abutting the entrance to Long Point Beach, considered by many to be the best beach on the Island. Home was built for families in mind, with three bedrooms upstairs, master with queen bed and ensuite bathroom. In addition there are two bedrooms, each

  Karen Overtoom Karen M. Overtoom R.E.

  196 Vineyard Meadow Farms Wt130, West Tisbury, MA 02575
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  $13,000 per month plus fees

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

  14 Pulpit Rock Rd, Oak Bluffs, MA 02557

  PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

  Karen Overtoom Karen M. Overtoom R.E.

  14 Pulpit Rock Rd, Oak Bluffs, MA 02557
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  $18,000 per month plus fees

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  40 Lighthouse Rd, Aquinnah, MA 02535

  Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Lighthouse Rd, Aquinnah, MA 02535
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  $40,000 per month plus fees

  • 6 Beds
  • 3 Baths
  • 1,704 Sq Ft
  • House for Rent

  120 Eastville Ave Ob520, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

  Karen Overtoom Karen M. Overtoom R.E.

  120 Eastville Ave Ob520, Oak Bluffs, MA 02557
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  $30,000 per month plus fees

  • 3 Beds
  • 3 Baths
  • 2,888 Sq Ft
  • House for Rent

  101 Peasepoint Way Ed324, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. This grand and stately home is located in Starbuck Point in Edgartown. The home is elegantly furnished with traditional charm . The Captain's house is surrounded by neatly manicured lawns and the ocean is at the end of the street. It is a five minute walk to the Edgartown Village and Harbor for shopping, dining or theater.

  Karen Overtoom Karen M. Overtoom R.E.

  101 Peasepoint Way Ed324, Edgartown, MA 02539
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  $27,000 per month plus fees

  • 4 Beds
  • 3.5 Baths
  • 1,962 Sq Ft
  • House for Rent

  20 Bay Lot Circle Ed323, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappiquidick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the ocean breezes and sandy beaches, there is great sunbathing,

  Karen Overtoom Karen M. Overtoom R.E.

  20 Bay Lot Circle Ed323, Edgartown, MA 02539
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  $12,500 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  138 South Rd, Chilmark, MA 02535

  THIS IS A SUMMER RENTAL ONLY. This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy, comfortable house in a central location. Three ceiling fans and 3

  Karen Overtoom Karen M. Overtoom R.E.

  138 South Rd, Chilmark, MA 02535
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  $14,000 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  88 Quenames Rd, Chilmark, MA 02535

  THIS IS A SUMMER RENTAL ONLY. This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors and simple, appropriate cottage touches. There is a new expansive deck

  Karen Overtoom Karen M. Overtoom R.E.

  88 Quenames Rd, Chilmark, MA 02535
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  $56,000 per month plus fees

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

  337 Barnes Rd Ob526, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fresco or try a nearby bistro or 5 star restaurant----the choice is

  Karen Overtoom Karen M. Overtoom R.E.

  337 Barnes Rd Ob526, Oak Bluffs, MA 02557
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  $12,000 per month plus fees

  • 3 Beds
  • 1.5 Baths
  • 820 Sq Ft
  • House for Rent

  8 Beach Plum Path Ob525, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This irresistible home is a 3-minute walk away from a deeded, sandy, sheltered beach and only a 5-minute drive to the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soaring ceilings, a wood-burning fireplace, and delightful furnishings.

  Karen Overtoom Karen M. Overtoom R.E.

  8 Beach Plum Path Ob525, Oak Bluffs, MA 02557
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  $13,200 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  8 Lobsterville Rd, Aquinnah, MA 02535

  Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Beach.

  Karen Overtoom Karen M. Overtoom R.E.

  8 Lobsterville Rd, Aquinnah, MA 02535
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  $7,900 per month plus fees

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
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  $112,000 per month plus fees

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft
  • House for Rent

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568

  Karen Overtoom Karen M. Overtoom R.E.

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568

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