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55 Worcester Ave, Oak Bluffs single family home — photo 1 of 30
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55 Worcester Ave

332Sleeps 8

Oak Bluffs

$5,000 – $12,000 per week

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55 Worcester Ave

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Custom built with exceptional craftsmanship and thoughtfully designed for comfort, this beautiful Oak Bluffs retreat offers the perfect setting for an unforgettable Martha's Vineyard vacation. Tucked away in a quiet residential neighborhood, yet just two miles from downtown Oak Bluffs, Town Beach, and the iconic Inkwell Beach, the home provides the ideal balance of privacy, convenience, and easy access to the island's shops, restaurants, and beaches.

Designed with both entertaining and everyday relaxation in mind, the home offers four separate living spaces, allowing families and groups to gather together while still enjoying plenty of room to spread out. The open and inviting floor plan extends seamlessly to the outdoor living areas, where a spacious deck with dining and lounge seating overlooks the peaceful backyard.

At the heart of the main level is a beautifully appointed gourmet kitchen, flanked by two dining areas and two inviting living rooms. One living space is centered around a media and entertainment area, while the second offers a comfortable setting for conversation and quality time with family and friends. Every space has been carefully designed to create a warm, welcoming atmosphere that embodies relaxed Vineyard living.

The finished lower level provides an additional gathering space with a large sectional sofa and television, perfect for movie nights or a quiet retreat. A convenient powder room is also located on this level.

Upstairs, the second floor features three well appointed bedrooms along with a loft lounge complete with comfortable seating including a pull out sleeper sofa and a television, creating yet another place to unwind.

With multiple living areas, inviting outdoor spaces, and an unbeatable location just minutes from Oak Bluffs' vibrant downtown, beaches, dining, and entertainment, this exceptional vacation home is the perfect place to experience the very best of Martha's Vineyard.

Wallace & Co. Sotheby’s International Realty attempts to accurately represent the Premises to the best of our ability. Our information is deemed reliable but not guaranteed. Opinions as to the condition of the Premises vary from individual to individual and are very subjective. We highly recommend that you personally view the property before signing the lease to verify the information in the advertised listing sheet. Be aware that numerous types of molds occur naturally on Martha’s Vineyard; some people may be sensitive to and have allergic reactions from the same. Any house built prior to 1978 may contain lead paint.

Bedrooms

Bedroom 1

Second Floor: King Bed, Private Bath

Bedroom 2

Second Floor: Queen Bed, Private Bath

Bedroom 3

Second Floor: Two (2) Queen Beds, Private Bath

Amenities

Featured Amenities

  • Lawn / Garden Area
  • Outdoor Shower
  • AC - Central Air

Indoor Amenities

  • Finished Basement

General

  • Hair Dryer
  • Washer/Dryer
  • Vacuum

Linens

  • Linens - Provided

Nearby Attractions

  • Bike Path
  • Beach - Town
  • Downtown

Kitchen And Dining

  • Bakeware
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Microwave
  • Oven/Stove
  • Refrigerator
  • Toaster

Entertainment

  • Wireless Internet
  • TV - Smart TV

Outdoor Amenities

  • Beach Chairs
  • Driveway Parking
  • Patio
  • Porch
  • Deck
  • Grill - Gas
  • Outdoor Dining Area
  • Outdoor Furniture

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October 2026

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Rates & Availability

May 2027 – August 2027

May 2027

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June 2027

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$5,500/week
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$6,500/week
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$7,500/week
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$9,000/week

July 2027

Su
Mo
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$9,000/week
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$9,000/week
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$9,000/week
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$11,000/week

August 2027

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$12,000/week
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$12,000/week
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$12,000/week
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$10,000/week
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$9,000/week
Available BookedCheck-out day — available from middayCheck-in day — available until the afternoon

Rates and availability are subject to change and may not be current. Published rates do not include local & state taxes. Please contact your Wallace & Co. Sotheby’s International Realty agent to confirm current rates and availability.

$5,000 – $12,000 per week

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Location

Oak Bluffs

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