COASTAL CONTEMPORARY IN KATAMA. An exceptional Katama retreat, this beautiful coastal contemporary offers a refined expression of island living, thoughtfully designed for both casually elegant entertaining and effortless summer relaxation. Set on beautifully landscaped grounds between Edgartown Village and South Beach, this custom-built residence pairs sophisticated architecture with an inviting sense of ease.

The centerpiece of the home is a spectacular two-story Great Room, where dramatic volume, abundant natural light, and a gas fireplace create an impressive yet comfortable gathering space. The open living and dining areas extend naturally to a generous screened porch, blurring the distinction between indoor and outdoor living and providing an ideal setting for everything from morning coffee to sunset dinners.

The beautifully appointed eat-in kitchen combines custom cabinetry with all-new appliances, offering both exceptional functionality and understated elegance. A private primary suite occupies the main level, while the second floor features a spacious guest suite and an adjoining open living and recreation space overlooking the great room. A recent second-floor expansion adds more than 200 square feet of beautifully integrated living space, further enhancing the home's generous proportions.

The outdoor spaces are equally compelling. Expansive, professionally landscaped grounds offer exceptional privacy and ample room for a future pool, while a handsome stone terrace with a private hot tub creates an intimate setting for evenings beneath the stars. The screened porch and outdoor living areas invite a relaxed rhythm of Vineyard life, with room to gather, dine, entertain, and simply enjoy the beauty of Katama.

Additional amenities include central air conditioning, a full unfinished basement offering significant potential for additional living or recreational space, and a two-car garage with abundant storage for everything that comes with island living.

Beautifully conceived and exceptionally well maintained, 26 Pulpit Lane offers the rare combination of architectural presence, modern comfort, generous outdoor space, and an enviable Katama location—a sophisticated Martha’s Vineyard residence designed to be enjoyed for generations.

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26 Pulpit Lane

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BUILD YOUR HOME on this beautiful lot! Centrally located close to Farm Neck, bike path, and more, this property offers a wonderful opportunity to create your own home. Located in a newly created sub-division on a dead-end road, there is a baseball field right across from the property. This preserves the open feel of the area. As part of a new subdivision, the property is approved for a one-bedroom septic system. 
The perk test is complete, and the site plan is ready and will be included with the sale. 
A perfect opportunity to be creative and bring your vision to life. Build your own home in a unique setting, close to town and everything Oak Bluffs has to offer.  Building package may be available.

109 Forest Avenue

Perched atop the highest point on Chappaquiddick, this private compound truly has it all, while still being a short distance from Chappy favorites including the Community Center, Beach Club, Ferry, and Slip Away Farm. Designed for both relaxation and recreation, the property offers endless ways to enjoy time with family and friends. Spend the afternoon on the sports courts, cool off at the pool, or relax on one of the expansive porches or patios.

The guest house provides additional space and privacy. The pool house, complete with a half bath and kitchenette, makes entertaining effortless, with everything you need close at hand. A separate gym and game room offer even more ways to stay active or unwind, whatever the weather. 

With a strong rental history, the property also presents an excellent investment opportunity, while its generous amenities and multiple living spaces make it an ideal generational home to be enjoyed for years to come.

72 Chappaquiddick Avenue

Set just across from iconic Inkwell Beach in Oak Bluffs’ historic Copeland District, 8 Pequot Avenue offers a rare combination of architectural character, water views and an exceptional in-town location. Built in 1870, this distinctive Victorian retains many of the period details that make this neighborhood so recognizable, from decorative gingerbread trim and steeply pitched rooflines to pointed-arch windows and doors, painted wood interiors and charming upper-level spaces tucked beneath the eaves.
Inside, the five-bedroom home has an easy, informal layout centered around a living room with a substantial fieldstone fireplace. An updated kitchen and bath add modern convenience while preserving the character of the original home. There are 1.5 baths, an outdoor shower and partially insulated spaces that help extend enjoyment beyond the summer season.
The front porch has been a gathering place for generations and remains one of the home’s most inviting features—a place to sit, catch the sea breeze and enjoy the activity of this special neighborhood. Inkwell Beach is just across the way, while Ocean Park, the harbor, ferries, shops and restaurants of downtown Oak Bluffs are all within easy reach.
With its remarkable location, five-bedroom layout and authentic period details, 8 Pequot Avenue offers an opportunity to preserve and enhance a piece of Oak Bluffs history while making it your own. Property is being sold as-is.

8 Peqout Avenue

PHOTOS COMING SOON-Nestled within Edgartown’s coveted Katama/Island Grove enclave, 32 Martha’s Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication—rich with architectural intention, bathed in natural light, and thoughtfully composed for both intimate daily living and memorable entertaining.

Set on .5 acres, the home unfolds across approximately 3,594 square feet, with an additional 2,300+ square feet of high-ceilinged, unfinished basement space offering extraordinary future potential. Cathedral ceilings, refined millwork, and expansive windows throughout create an atmosphere of lightness and luxury.

A soaring, cathedral-height entryway immediately captivates, framed by striking two-story windows that draw the eye through the home to the serene, professionally landscaped backyard beyond. The foyer’s scale and natural light set the tone for the residence’s modern, airy aesthetic.

The open-concept kitchen, dining, and living areas form an inviting central gathering space anchored by a warm gas fireplace and illuminated by windows on both sides. The gourmet kitchen is a true showpiece, featuring Thermador appliances, an expansive center island, and exceptional craftsmanship. It opens to a deep, walk-in pantry and a beautifully designed entertaining area complete with a sink, Zephyr beverage refrigerator, generous shelving, and abundant storage—functioning perfectly as a wet bar when hosting family and friends.

Just beyond, a stunning screened porch extends the living space outdoors, offering a wood-burning fireplace and direct access to the stone patio and level backyard. With ample room for recreation and the potential for a future pool, the property invites endless enjoyment.

With commanding curb appeal, flexible expansion opportunities, and abundant outdoor space, 32 Martha’s Road stands as an exceptional offering in one of Edgartown’s most desirable neighborhoods. Beautifully conceived, crafted with care, and designed with intention, this modern farmhouse is ready to be made uniquely your own—a rare opportunity to enjoy Vineyard living at its most refined.

32 Marthas Road

Martha's Vineyard has many fine waterfront properties but only a handful of exceptional ones.  The Lee Family Compound is an exceptional 3 acre waterfront property with breathtaking unobstructed pond views from an elevated secure location, 750+ ft of pond frontage, 48 ft dock with separate mooring for easy access to Menemsha Pond and Vineyard Sound and privacy without an abutter in view - all compliment the spacious 5 bedroom 5 bath comfortable well built main house and well sited 2 bedroom 1 bath contemporary guest house.  The stunning views are everywhere so 14 of the 16 rooms in both houses enjoy grand pond views.  Because of the elevation -- the sunsets, moonrises, and stargazing are some of the most remarkable the island has to offer.  The two home compound can house 18 comfortably and is perfect for year-round family events.  Come launch your canoe, kayak or paddle board from spring to fall; swim, clam or sail from private sandy beach off the point all summer long; sunbathe on your private dock or 3 decks or on the terraced lawn overhanging the cove; and enjoy seasonal holidays by a roaring fire with extended family and loved ones.  This compound is proof that a picture is worth a 1,000 words.(see Video Aerial Tour)

1 Clam Point Cove Road

A wonderful opportunity to enjoy island living within one of Oak Bluffs’ most desirable private communities. Set on over 65 acres, Hidden Cove offers the perfect combination of privacy, recreation, and easy Vineyard living.
This contemporary three-bedroom and three bath home has been thoughtfully renovated and is offered fully furnished. The modern aesthetic complements the home’s architectural design, with a lofty living room ceiling and a fireplace, and an open kitchen and dining area with multiple glass sliders to the back deck. The back deck is buffered by mature trees, that creates a private setting for outdoor dining and entertaining.

The comfortable floor plan features a first-floor primary suite, with two spacious bedrooms, a full bath, and an open loft area upstairs, plus ample eave storage. Offered turnkey with a solid rental history in place. This home works equally well as a personal Vineyard retreat or investment property. 

Hidden Cove residents enjoy private access to Sengekontacket Pond, an association dock and kayak/boat storage, tennis and pickleball courts, and scenic walking trails. Centrally located between Oak Bluffs and Edgartown, the location offers convenient access to beaches, bike paths, shopping, and dining.

10 Ploughshare Lane

The North Bluff: A rare opportunity to acquire one of Oak Bluffs’ most iconic properties. Originally built in 1913 and expanded over the years, this distinctive property occupies a prominent setting within the B-2 district, offering a unique range of residential and commercial opportunities. Cherished by the same family for generations, the multi-family property currently comprises four separate living spaces, complemented by substantial garage and storage areas and ample on-site parking. A classic front porch speaks to the property’s early-20th-century character, while expansive decks provide wonderful settings for outdoor entertaining and taking in the surroundings. Beautiful views of Oak Bluffs Harbor and Vineyard Sound can be enjoyed from nearly every room, creating an exceptional sense of place. Whether envisioned as a grand single-family residence, a distinctive commercial venture, or a continuation of its current blend of residential and commercial uses, The North Bluff presents extraordinary potential. With thoughtful planning and the appropriate permitting, this landmark property offers a remarkable opportunity to shape its next chapter.

31 Circuit Avenue Extension

A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

12 Boldwater Road

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.

42 Bold Meadow Road

In a beautiful coastal setting, this 4-bedroom, 4.5-bath wood-sided contemporary is perched on 1.8 private waterfront acres in Major’s Cove, with frontage on Sengekontacket Pond, and offers a functional floor plan with exceptional views. Expanded over time, the home now includes a primary suite and laundry on the main living level, with comfortable living spaces opening to expansive wraparound decks. The home offers approximately 3,148 square feet of finished space, including approximately 800 square feet on the finished lower level, with substantial above-grade exposure at the rear. An upper-level ensuite bedroom and two additional bedrooms with two full baths on the lower level provide flexibility for family and guests. Improvements include newer windows and doors, new mini-split systems, new hot water heaters, and work to several bathrooms. The September 2026 Title V inspection passed and supports a five-bedroom septic capacity. With town water, only one existing structure on the 1.8-acre parcel, and substantial acreage, the property may offer long-term potential for expansion or future improvements, subject to applicable approvals. Life at Major’s Cove includes access to tennis and pickleball courts, a community boat launch, and kayak storage. HOA services include private-road maintenance, snow removal, and common-area landscaping. Whether enjoyed as a peaceful waterfront retreat or a home with room to evolve over time, this property offers exceptional privacy, versatility, and a distinctive island setting.

24 Myober Lane

Set within an established island community, this spacious condominium offers tall ceilings, an open floor plan, abundant windows, and wonderful natural light, with views toward the surrounding woods. Its flexible layout and exceptional community amenities make it an inviting choice for year-round living or a seasonal Vineyard retreat.
The first floor features open kitchen, dining, and living areas centered around a fireplace, plus a versatile study and full bath. The second floor offers two private bedroom suites, each with its own full bath, along with conveniently located laundry. An unfinished basement provides generous storage and future possibilities.
Outdoor living includes a wraparound deck with wooded views, an outdoor shower, garage, additional storage, and established perennial plantings. Residents enjoy a heated pool, tennis courts, approximately 500 feet of Vineyard Sound beach, and a private boat landing—offering easy access to the water and the best of island living.
*Located within the Tashmoo Watershed area.

176 Sandpiper Lane 12

Centrally located at the top of Daggett Avenue, just blocks from the harbor and town beach, sits this charming turn of the century Cape. The covered porch graces the front of the home welcoming friends and family. Light spills into the living room that stretches across the front of the house featuring vintage architectural details and the warm patina of newly refinished Carolina pine floors. Continue through the framed wide entrance to the dining room featuring a built-in corner China cupboard. The sweet country kitchen has been updated with new appliances and flooring. The laundry with new large capacity washer and dryer and shower bath is conveniently located on the first floor. A central hall on the second floor opens to four corner bedrooms and a full bath. The walk-up attic provides plenty of storage.  Step into the newly landscaped yard with a new driveway and off-street parking. Other improvements include a new electrical service and wiring, dual heat/AC mini splits for the entire house, new Rothe fuel tank, newly shingled exterior and gutters, and the requisite outdoor shower. The windows were replaced by the previous owner.

95 Daggett Avenue

Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired décor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A first-floor bedroom provides added flexibility, while the enclosed 120-square-foot sun porch creates a wonderful extension of the living space. Outdoor living shines with a newer mahogany outdoor shower, bluestone patio and beautifully designed walkway, all surrounded by a private setting. An unfinished basement provides approximately 720 square feet of additional space for storage and future possibilities.  Walk or bike to Jetty Beach and the East Chop Lighthouse, enjoy the nearby East Chop Beach Club, or stroll to Oak Bluffs Harbor, downtown restaurants and shops. With a proven rental history and a desirable East Chop location, this move-in-ready property is equally suited as a Vineyard retreat, year-round home or investment opportunity. Please include a pre approval letter with all offers and or proof of funds for cash.

39 Chickawaukee  Street

Lovely residential lot with a rural feel. Conforming 1.397 acre wooded lot in R3 with 150ft frontage on County Rd very close to the entrance to Meadow View Farm. Residential with bike path access along County Rd. Has been surveyed, staked & tagged. Town water available along County Rd. Electric access box will need to be installed. Number of bedrooms allowed is more than 7 bedrooms. This is dependent on an approved septic design for what an new owner would like to build. Drone photos coming......

455 County Road

Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate mudroom/back entry. Recent updates include a new kitchen with new appliances, new baths, fresh interior and exterior paint, new lighting, and new flooring and carpet throughout.

234 County Road

Two complete homes on one acre in Edgartown's Smith Hollow neighborhood — a rare find. Set at the end of a paved cul-de-sac, the property gives each house its own septic system, its own landscaped yard, and enough separation for real privacy.
The main house has four bedrooms and two baths, along with a basement and a drive-under garage. The guest house features three bedrooms, two baths, a full basement, and laundry. With a solid rental history already in place, this is a chance to get two houses for the price of one.

4 Farm Way

A standout commercial offering in Edgartown, combining striking contemporary design with exceptional flexibility. Located just outside the historic district and just shy of 2,000 square feet, this commercial condominium offers a beautifully finished, thoughtfully designed interior that feels anything but ordinary. Soaring ceilings, polished concrete floors, dramatic black architectural details and walls of glass create a sophisticated, light-filled space with a modern industrial aesthetic. The versatile layout features an open reception or showroom area, multiple private rooms, a glass-enclosed conference room, additional work areas, and a half bath, allowing the space to adapt easily to a variety of business needs. A full 1,520± square foot basement provides substantial expansion, storage and utility space. Central heat and air conditioning, fire sprinkler system, town water and sewer, on-site parking and a dedicated loading area add everyday convenience and functionality.  Renovated in 2021 with an uncommon level of style and attention to detail, this is a compelling opportunity for an owner-user or investor. The Master Deed allows for a broad range of commercial uses, subject to Edgartown zoning and other applicable regulations and restrictions.

1 Mariners Way A

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