COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming, sailing, and relaxing with friends or family are just a few of the daily dalliances of time spent on Chappy. There is simply no better place to relax and unwind.

View Property Details >

Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with strong rental history!

View Property Details >

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN ROWLEY COTTAGE, Unit 62 at 131 N Water Street in Edgartown, a 895-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after an extensive restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a cooktop, microwave, and refrigerator/freezer. Both bedrooms are well proportioned, and the two full bathrooms are designed for everyday ease. An outdoor shower enhances the coastal lifestyle. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Rowley Cottage, Unit 62 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

View Property Details >

Close to South Beach! Close to Katama Airpark and nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home. Conveniently located just off the bike path, and only a mile to the desirable South Beach, the location doesn’t get much better than this. Property is being sold “as is”. Buyer is responsible for the research on how to make this pre-existing, non-conforming property conform to today’s building and zoning requirements.

View Property Details >

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick’s most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird’s-eye views capture the natural beauty that surrounds you. Thoughtfully renovated throughout, the home blends modern updates with custom finishes to create a rare balance of style, comfort, and year-round functionality—an uncommon find in this idyllic setting. Enjoy direct access to Katama Bay, just a three-minute stroll down the road. Its calm waters and sandy shoreline are ideal for swimming, boating, and shellfishing. Nearby, the Wasque Preserve offers over 200 acres of pristine conservation land, featuring scenic trails, abundant wildlife, and direct ocean beach access. Whether you’re seeking a serene coastal retreat, a multi-generational family home, or a proven investment property, 76 Washque delivers it all. With an impressive rental history and consistent bookings during both summer and shoulder seasons, it stands out as a premier opportunity in today’s market. This home is more than just an address—it’s the essence of Chappy living.

View Property Details >

Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence blends warmth, character, and enduring craftsmanship. The spacious 4-bedroom, 3-bath home features soaring cathedral ceilings, wide pine floors, a mudroom with built-in storage cubbies, and a generous office/media/playroom complete with custom desks and bookcases. Sun-filled living spaces feel both open and inviting, while a striking brick fireplace anchors the living room — the perfect gathering place after a day at the beach. The property also includes a charming guest cottage, outdoor shower, and large shingled shed, all thoughtfully positioned within a beautifully private setting abutting conservation land. Expansive front and rear decks invite outdoor living, entertaining, and quiet moments immersed in the natural beauty of Chappaquiddick. Thoughtfully updated for comfortable year-round living, the home includes central heating and air conditioning, a whole-house water filtration system, heated mudroom and bathroom floors and energy-efficient solar panels that help keep annual utility costs remarkably low. Located just three miles from the heart of Edgartown, the property is a short walk to Katama Bay, where kayaks and sailboats may be stored, and only 1.5 miles from the pristine shores of Wasque and East Beach. Property Highlights * Distinctive post-and-beam architecture * 4 bedrooms | 3 bathrooms * Separate one-bedroom guest cottage with outdoor shower * Large shingled storage shed * Sprinkler system * Private lot abutting conservation land * Spacious yard with exceptional privacy

View Property Details >

Imagine owning your own beach house on Martha’s Vineyard, ready for summer fun. Perched atop a rise that captures sweeping views over the property, floods interiors with natural light, and opens to a spectacular night sky, this furnished move-in-ready home delivers the Vineyard lifestyle you've been imagining — with room for everyone. Over 2,600 square feet (not including the walk-out basement) unfold across four levels, beginning with a dramatic 30-foot vaulted foyer bathed in sunlight. The fully renovated chef's kitchen features Sub-Zero paneled refrigerator, luxury stainless steel appliances, and stone counters, opening onto a favorite gathering place in the heart of the home - a custom banquette with built-in window seats that easily seats 10. A formal dining room, oak floors, a wood-burning stone fireplace once featured in Architectural Digest, and a view-facing living room with balcony set the tone for effortless entertaining. The primary suite features a walk-in closet and en-suite bath, complete with a sunken tub and double vanity. Two additional bedrooms share a full bath. A sculptural spiral staircase rises to a loft lounge with glass doors to a private balcony — perfect for stargazing or savoring the serene setting — plus two bonus rooms for overflow guests. The walk-out lower level(an additional 900 s/f not included in the s/f), with custom stained concrete floors and new Andersen French doors, adapts easily as a lounge, home office, or gym. Overall, the home is well-maintained, lightly used, with regular renovations and upgrades, including a HydroViv water filter system. The expansion potential is exceptional: a sewer connection option allows growth to seven bedrooms, with room for a guest house, pool, and pool house. Seller is offering $25,000 at closing for the sewer tie-in. There is flex space within the existing floor plan ready for additional bedrooms. Minutes to Vineyard Golf Club, Morning Glory Farm, South Beach, Edgartown Village, and scenic bike paths.

View Property Details >

A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between. Gather around the custom firepit under a canopy of stars, soak in the sauna and cold plunge after a day on the water, or simply unwind on the porch as the island quiets down around you. The three-bedroom main house offers warm, open living spaces, while the two-bedroom guest house — with its covered porch, back deck, and outdoor shower — keeps guests close but comfortably their own. Recent renovations include extensive landscaping, new features, exterior paint, select Vineyard Decorators furniture, plus stainless steel appliances. Move-in ready and offered turnkey with few exclusions for immediate enjoyment. Everything here is geared toward living well outdoors. An oversized garage with furnished loft space provides room for the gear and the gang. Chappy's beaches, hiking trails, Slip Away Farm, and the Community Center are all just minutes away — but with a place this special, you may never want to leave. Offered turnkey with no rentals in place - ready for summer fun!

View Property Details >

LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN HUXFORD COTTAGE, Unit 94 at 131 N Water Street in Edgartown, a 730-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after a restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a microwave, and refrigerator/freezer. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Huxford Cottage, Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

View Property Details >

A Rare Edgartown Opportunity — Privacy, Proximity & Possibility. Tucked away at the end of a private setting on Upper Main Street, this almost one acre parcel offers a rare opportunity to create your own Edgartown retreat within easy walking distance of downtown. Set well back from the road, the property provides a wonderful sense of privacy and seclusion while being remarkably close to the restaurants, shops, galleries, harbor and village life that make Edgartown so desirable. The property offers the potential to build a main residence and guest house, with the two structures together supporting up to seven bedrooms, along with the ability to add a pool and create the quintessential island compound. A small, older guest quarters and shed currently occupy the property and could be removed to make way for a thoughtfully designed new vision. For those seeking the best of both worlds, a private setting with the convenience of town just moments away this parcel of land presents an exceptional opportunity to create a custom Edgartown property tailored to your lifestyle. Bring your architect and imagine what could be created on this special piece of land.

View Property Details >

Tucked at the end of a quiet cul-de-sac in the desirable Island Grove neighborhood of Edgartown, this charming three-bedroom, (plus bonus space and 6 bedroom sewer capacity), two-bathroom residence offers a private setting, association amenities and excellent proximity to Edgartown Village and Katama Beach. Located on arguably one of the most desirable lots in Island Grove and surrounded by conservation land, this half acre lot benefits from peaceful woodland views and has a direct pathway to the association tennis and pickle ball courts. The property has been recently connected to town sewer, with the potential for expansion to SIX BEDROOMS subject to Board of Health confirmation and approval. In addition to the sewer connection, the home benefits from having several significant upgrades including new roof, new windows, and mini-split air conditioning. The main level features a double-height living room with south-facing windows and French doors opening to a generous sun deck and lawn—an inviting setting for summer entertaining and relaxed outdoor living. A wood stove adds warmth and character for cozy fall and winter evenings. The well-equipped kitchen flows comfortably into the dining area, while two spacious bedrooms and a full bath complete the main level. Upstairs you will find the private primary suite with balcony overlooking the yard, and full bathroom, plus bonus loft room which makes a great office, den or additional guest space. On the lower level is a finished bonus room, laundry area and plenty of storage. With its exceptional setting, desirable Island Grove location, recent improvements, expansion potential, and strong rental history, this property presents an appealing opportunity to enjoy immediately while offering the flexibility to enhance and expand over time.

View Property Details >

A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom with full bath and kitchenette located above the attached garage for a separate guest retreat. The walkout basement provides storage, laundry and future potential. A versatile property thoughtfully designed for comfortable year-round living and quintessential Vineyard summers. Bold Meadow community tennis & pickleball courts nearby and abutting State forest bike path and hiking trails right from your back door.

NEW

View Property Details >