Waterfront Family Escape with Private Dock, Beach & Stunning Sunsets

Escape to this beautiful 5-bedroom waterfront cottage on East Chop Drive in Oak Bluffs, where coastal charm meets comfort and relaxation. Tucked away in a peaceful setting yet just minutes from the ferry, this inviting home is the perfect retreat for families and friends looking to experience the best of Martha’s Vineyard.

Enjoy the rare luxury of a private beach and dock, ideal for swimming, kayaking, paddleboarding, boating, or simply relaxing by the water. Start your mornings with coffee on the deck overlooking the harbor, spend your afternoons exploring East Chop by foot or bicycle, and end each day with spectacular sunset views over the water.

Inside, the cottage offers 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, along with bright, comfortable living spaces and a fully equipped kitchen for gathering and entertaining. The warm, welcoming atmosphere makes it easy to settle in and create lasting memories with family and friends.

Whether you’re seeking a quiet waterfront escape or an unforgettable Vineyard vacation filled with outdoor adventures, this special East Chop property offers the perfect blend of privacy, convenience, and classic island charm.

Experience the beauty, tranquility, and charm of waterfront living at 301 East Chop Drive.

Coastal Living in Katama —
Main & Guest House
with Heated Saltwater Pool

Welcome to your Katama escape — a coastal charmer that blends island style, comfort, and effortless outdoor living. Thoughtfully decorated with a relaxed seaside flair, this property invites you to settle in and enjoy the best of Martha’s Vineyard living.

Start your days by the new heated saltwater pool, beautifully fenced and surrounded by lovely landscaping and pristine hardscaping. The 10’ x 20’ pool area is a private retreat of its own, complete withcomfortable lounge seating and a dining table for meals under the sun or stars.

The Main House offers three bedrooms and two baths in an open, airy floor plan that connects the living, dining, and kitchen spaces. Gather around the gas fireplace or enjoy movie nights on the large-screen TV. A gourmet kitchen provides everything you need to entertain or cook up fresh local fare from Morning Glory Farm.

Dine indoors or alfresco just off the living room—perfect for casual evenings or larger family gatherings. The first-floor bedroom opens to its own private deck and shares a full bath with laundry. Upstairs, the primary bedroom and guest bedroom share another full bath, and both enjoy beautiful natural light. The primary suite also features its own private deck, ideal for morning coffee or stargazing at night.

For guests seeking extra privacy, the Guest House above the garage offers a complete one-bedroom suite with a living area, ensuite bath, and a full kitchen with a breakfast bar, stove, microwave, full-size refrigerator, and its own private deck.

Centrally located between Morning Glory Farm, downtown Edgartown, and South Beach, you’re just a short bike ride from everything that makes Katama special. Whether you’re relaxing poolside, dining outdoors, or exploring the island, this property captures the essence of Vineyard living—easy, elegant, and unforgettable.

Welcome to Twin Pines Vineyard Haven — a family-friendly retreat just minutes from all the best attractions! Sleeps 8.

3 Bedroom | 2.5 Bath

Welcome to your perfect island getaway in lovely Vineyard Haven! This bright, comfortable, and well-equipped home is ideal for families or groups seeking a relaxing vacation with easy access to beaches, golf, and downtown Vineyard charm. Whether you’re hitting the beach, exploring downtown, or simply enjoying a relaxing evening on the deck, this well-located and family-friendly home offers everything you need for a memorable Vineyard vacation.

Location Highlights:

• Just 1.4 miles from downtown Tisbury’s shops, dining, and attractions.
• 1.8 miles to Tisbury Town Beach – a quiet spot perfect for swimming and picnics.
• 1.4 miles to Owen Park Beach with gentle surf and scenic harbor views.
• Only 1.5 miles to Mink Meadows Golf Course – great for a quick round or leisurely day on the green.

Edgartown Oasis with Saltwater Pool and Cabana

Vacation in comfort and style at this quintessential shingle-style Edgartown property. Ideally located, this immaculately maintained five-bedroom home is just a 5-minute walk from Edgartown Village, giving you easy access to local shops, dining, Edgartown Harbor and boating.

Property Highlights:

• 4 Spacious Bedrooms: Plenty of room for family or friends.
  Sleeps 8. 
• Saltwater Pool & Cabana: Perfect for entertaining or relaxing. The charming pool house doubles as a great spot for poolside fun or a remote work office.
• Newly Renovated Kitchen: Fully stocked and ready for hosting and preparing meals.
• Perfect for Entertaining: With a comfortable welcoming layout and all the amenities you need for a seamless getaway.

This Edgartown gem offers both the charm of a quiet retreat and the convenience of being just steps from the heart of town. Whether you’re looking to relax by the pool, host a gathering, or explore the island, this home has it all

Lagoon Waterfront 3 Bedroom Private Sandy Beach Oak Bluffs Martha’s Vineyard

Adding 2 new bedrooms, a cozy sitting room, and stunning bathrooms with breathtaking views of the lagoon IN 2025!

This three-bedroom idyllic vacation home offers the perfect escape for a truly memorable summer vacation on Martha’s Vineyard. Nestled on the shores of Lagoon Pond in Oak Bluffs, the house provides a summer recreational setting with its private sandy beach and unobstructed panoramic views of the tranquil Lagoon. Fishing, clamming and two kayaks provided. The newly updated in 2024 property sparkles with beautiful and comfortable furnishings. Lower level adds bonus tv and playroom for kids replete with Ms. Pacman and large screen tv. Sleeps 8. Saturday to Saturday Rentals with a few exceptions for first season bookings.

Architect Designed Oasis in Exclusive Oyster Pond -Pool, Kayaks & Beach!

Escape to a private paradise nestled in Edgartown’s exclusive Oyster Pond with this beautiful, modern-style custom home offering a unique blend of tranquility and recreation. Immerse yourself in the serenity of 7 acres of private meadow with private pond access to a stunning beach. This gem is enhanced by a beautiful heated inground pool and hot tub. The use of kayaks and the ability to rent a boat for your stay add a ton of summer fun and recreation to this secluded retreat! The fully equipped kitchen has all the ingredients to staycation in or plan a wonderful evening out at one of Edgartown’s finest restaurants. There is so much to do you will wish you stayed longer! Whether you’re seeking relaxation, adventure, or a bit of both, this architect-designed home provides the perfect canvas for a memorable vacation. *The owners are in process of building a pickleball court for 2024, stay tuned!

A New Beautifully Designed House in Katama with Pool and Hottub!

This newly built luxurious contemporary home offers indoor-outdoor Vineyard Living! A well-known local architect designed this beautiful house that has an open concept inside and outside with a heated pool with a hot tub, a large stone patio, and a screened porch for outdoor living. The living area is all glass windows with a stone fireplace, sliding doors both to a deck and a pool area, and a screened porch with a fireplace. The Chef’s kitchen has a large center island for prep and also a breakfast bar, commercial stainless appliances, and quartz counters. The kitchen opens to a lovely dining area.
There is a luxury first-floor Master Bedroom suite with a private bath and sliders out to the pool, and a private living room with a TV. The other three bedrooms are upstairs with each bedroom ensuite. There is another sitting area as well. 
There is a large freshwater pool and spa with room for 6 people. This house is in a quiet area close to Edgartown South Beach and Morning Glory Farm.

Beautiful Custom Built House with a Pool and Hot Tub!

A gorgeous builder’s house; this hidden pearl is elegant, private and relaxing. Conveniently located 3 miles from the Triangle in Edgartown and 4 miles from downtown Oak Bluffs with bike paths in both directions, situated off a main road in a very quiet dead-end neighborhood with plenty of opportunities for biking in the woods and walking around neighborhood ponds, and very close to many of the Town’s beaches. The 4200 square feet contemporary house has a main floor with am open cathedral ceiling great room that overlooks the heated pool. Sliding glass doors lead to beautifully Zen landscaped exterior space with areas for dining under an umbrella, sitting on a couch next to the pool, playing bean bag toss, grilling a steak, or sitting in the hot tub. Outdoor lighting allows ultimate enjoyment of this magical oasis.
There is an amazing gourmet kitchen to satisfy any cook or chef’s desire to whip up a quick lunch or a lovely dinner. Remarkably, this is not only an amazing place to gather,
it is a wonderful place to find reflection, Recharge, have adventures, inspire.

Beautiful house in Edgartown with Heated Pool

Vacations are important in your life, and you need a special house where the whole family can enjoy themselves. This beautiful house with a heated saltwater pool, close to the Island beaches, and downtown Edgartown, is just perfect for a family vacation. Come and enjoy a summer vacation like no other that you have ever had. This is island living at its best!!

Vineyard Living at it’s Best!

This newly renovated condo is located in the quiet Sengekontacket community which is centrally located to all the down-island towns, Oak Bluffs, Edgartown, and Vineyard Haven. The 2 bedroom, 2 bath condo with a sleeping loft on the third floor, has been furnished with new coastal furniture and decor.

The amenities include beautifully landscaped tennis/pickle-ball courts, rare private access to Sengekontacket Pond with a private boat launch, and a private dock for swimming, fishing, or kayaking. There are bike trails and wonderful areas in this community to run or take a leisurely stroll. This is Vineyard living at its best!!