LandVest Martha's Vineyard

09/25/2026

Now in its 81st year, the Martha's Vineyard Striped Bass & Bluefish Derby, Inc. has once again taken over the shoreline, harbors, and early-morning conversations of the Vineyard. Anglers are back on the water and weighing in at Derby Headquarters in Edgartown, carrying on a tradition that has brought generations of Islanders and visitors together since 1946.

And this year is already one for the books: a 19.91-pound false albacore weighed in by Sherry Countryman set both a new Derby record and Massachusetts state record.

But as anyone who has spent a fall on the Vineyard knows, the Derby has always been about more than the leaderboard. It is early mornings, familiar faces at the weigh-in station, stories traded on the dock, and an Island community gathering around one of its most enduring traditions.

Photo Credit: Larry Glick

09/25/2026

Bass in the Grass is an annual Edgartown tradition celebrating art, community, and the Martha’s Vineyard Striped Bass & Bluefish Derby. Each one-of-a-kind bass is created by a local artist and auctioned to support the Derby Scholarship Fund, participating artists, and the Edgartown Board of Trade’s work in our community.

Over the years Bass in the Grass has helped raise more than $70,000 for the Derby Scholarship Fund.

Auction is live and you can bid online here:

Join me in supporting EDGARTOWN BOARD OF TRADE: https://go.rallyup.com/bassinthegrass2026

09/24/2026

Long established as a Katama favorite, Katama General occupies a singular position along the route between downtown Edgartown and South Beach. Set just off the bike path in a largely residential setting, its commercial presence is unusually difficult to replicate, giving the property a distinction all its own.

Built in 2017 and offered in turnkey condition, the 3,027-square-foot property includes an expansive retail area, fully equipped commercial kitchen, dedicated food-preparation space, office, storage, and the infrastructure to support food service and catering operations. A seasonal b**r and w**e license, transferable with Town approval, adds another layer of possibility.

Outside, a generous wraparound porch and approximately 4,300 square feet of event space create room for gathering, dining, and seasonal programming, while 25 on-site parking spaces provide a rare convenience in such a sought-after location.

Beloved by residents and visitors alike, Katama General offers the opportunity not simply to acquire a commercial property, but to take stewardship of a familiar Island institution and imagine its next chapter.

$4,450,000 | 0.67 Acres | 3,027 Sq. Ft.

Listed by Gerret Conover & Thomas Leclair | LandVest

Explore the property: landvest.com/listing/MA5906

09/23/2026

Built in 1910 as one of the earliest homes at Herring Creek Farm, 31 Butlers Cove Road is a wonderfully intact antique farmhouse set on three acres overlooking open pasture, horse paddocks, and the rolling landscape of one of Edgartown’s most distinctive private communities.

The house retains the easy character of an old Island farmhouse, with original details, a generous living room with fireplace, dining room, four bedrooms, and broad views across the surrounding fields. Wildflowers, grazing horses, and long stretches of open land give the property a sense of space that feels increasingly rare.

Beyond the house, ownership within Herring Creek Farm includes access to more than 2,000 feet of private Atlantic shoreline, with 19 acres of association beach reached by foot, bicycle, or golf cart. South Beach, Katama Airfield, the bike path, and downtown Edgartown are all close by, though the setting feels worlds removed.

An evocative piece of old Katama, surrounded by farmland, ocean, and more than a century of Vineyard history.

$4,850,000 | 4 Bedrooms | 2 Full Baths | 3.04 Acres | 2,808 Sq. Ft.

Listed by Gerret Conover | LandVest

Explore the property: landvest.com/listing/43952

09/21/2026

For those who like their Vineyard summers with Main Street, the harbor, and the beach all within easy reach.

Set in the heart of Edgartown Village, 38 Simpsons Lane is a classic Colonial with a distinctly fresh point of view. Four levels of beautifully finished living space create plenty of room to gather, while an open floor plan keeps the house feeling relaxed, bright, and wonderfully suited to summer.

At the center of the home, the gourmet kitchen opens to generous living and dining areas, with French doors leading directly to a bluestone patio and private backyard. Beyond, mature landscaping surrounds a thoughtfully sited swimming pool, creating a secluded retreat just moments from the bustle of town.

Six bedrooms, a newly finished lower level, and 4,664 square feet of living space make this an unusually substantial in-town residence, while Fuller Street Beach, Edgartown Harbor, restaurants, and shops are all just a short stroll away.

A polished village home with everything close at hand and plenty of reasons to stay in.

$6,650,000 | 6 Bedrooms | 4 Full Baths | 2 Half Baths | 4,664 Sq. Ft.

Listed by Thomas Leclair | LandVest
508-627-0177

Explore the property: landvest.com/listing/MA5865

09/20/2026

Perched high above the water on 2.1 private acres, 12 Caleb’s Pond Lane commands a remarkable panorama across Edgartown Harbor, with nearly 180-degree views stretching from Memorial Wharf toward South Beach. From the broad decks, lawns, and nearly every principal room, the harbor unfolds below in full view.

The custom residence pairs exceptional craftsmanship with an unmistakably Vineyard sensibility, including design by Hutker Architects and distinctive stonework by Lew French. Warm wood interiors, walls of glass, and a dramatic stone fireplace frame the water without competing with it.

The three-bedroom main house is joined by a separate guest bedroom nearby, while the grounds include a pool and jacuzzi, expansive lawns, private beach, deep-water pier, and mooring. Across the meadow, a substantial barn creates an entirely different kind of retreat, with a basketball court, fitness space, sauna, and private guest apartment above.

For all its privacy, Edgartown feels remarkably close: take the skiff across the harbor or reach the Chappy Ferry in minutes.

A rare compound where architecture, landscape, and one of the Island’s most extraordinary harbor perspectives come together.

$17,500,000 | 5 Bedrooms | 4 Full Baths | 1 Half Bath | 2.1 Acres | 6,061 Sq. Ft.

Listed by Gerret Conover: 508-627-161

Explore the property:
landvest.com/listing/MA5845

09/18/2026

Perched high above the bluffs beside the historic East Chop Lighthouse, 233 East Chop Drive is the sort of New England waterfront house that feels almost too picturesque to be real. A Victorian-style residence, broad rolling lawn, wraparound porch, and extraordinary views across Vineyard Sound create a setting of rare character and beauty.

Inside, much of the home’s original charm remains intact, with a gracious living room and fireplace, sun-filled sunroom, and five bedrooms in the main residence. Nearly every room is oriented toward the water, where passing boats and changing light become part of the view.

The grounds stretch toward the bluff’s edge, with private steps descending to the shoreline below. A deep-water pier and private mooring make the Sound immediately accessible, while a detached two-car garage with a one-bedroom apartment offers additional accommodations for guests.

Lighthouse next door, Vineyard Sound out front, and one of the Island’s most iconic coastal landscapes all around.

$6,900,000 | 6 Bedrooms | 3 Full Baths | 2 Half Baths | 0.42 Acres | 2,522 Sq. Ft.

Listed by Gerret Conover | LandVest

Explore the property:
landvest.com/listing/MA5839

09/16/2026

SOLD!

6 Kent Harbor Road
Sale Price: $2,950,000

Congratulations to all involved in this sale! Another Martha's Vineyard property finds its next chapter. Sold by Cheri Mason, LandVest.

Interested in buying or selling on Martha's Vineyard? Reach out to our team today.

09/16/2026

A classic Edgartown exterior gives way to a residence that feels remarkably fresh.

Designed by Patrick Ahearn, 15 Tilton Way pairs traditional architecture with every modern comfort, all just a few blocks from downtown and the harbor. Graciously proportioned interiors, abundant natural light, and French doors create an effortless flow between the home and its beautifully landscaped grounds.

The main level includes a formal living room, private den, dining room, and generous kitchen and family room, while a deep covered porch with its own fireplace extends the living space outdoors. Upstairs, four bedrooms open onto private decks, and the finished lower level adds a fifth en-suite bedroom, TV area, and billiards room.

Outside, mature gardens create an unexpected sense of privacy around the swimming pool, jacuzzi, entertaining terrace, outdoor shower, and lush rear lawn.

Turnkey and impeccably finished, this is an in-town Edgartown home with all the bells and whistles, but none of the fuss.

$8,250,000 | 5 Bedrooms | 4 Full Baths | 1 Half Bath | 4,562 Sq. Ft.

Explore the property:
landvest.com/listing/MA5909/15-tilton-way-edgartown-ma-02539

Photography by Dania Alyse Photography

09/15/2026

There are very few places on Martha’s Vineyard quite like Cow Bay.

Set within this coveted ten-home association, 14 Cow Bay Road offers an unusual combination of privacy, water access, and proximity to Edgartown. The 1.5-acre property is reached by private road through protected land and enjoys association access to more than 2,000 feet of shoreline, a pristine private beach, Trapps Pond, beach cabanas, and potential mooring.

The residence itself is gracious without being formal, with beautifully proportioned interiors, a chef’s kitchen, generous living and dining spaces, and a sweeping screened porch overlooking the pool and toward Vineyard Sound.

Outside, mature gardens, broad stone terraces, wisteria-draped pergolas, and a beautifully designed pool and lounge area create the feeling of a private summer resort. A separate carriage house above the three-car garage provides additional accommodations for guests or staff.

Water views, private swimming, boating access, and one of Edgartown’s most desirable neighborhood settings, all just minutes from town.

$14,500,000 | 7 Bedrooms | 7 Full Baths | 3 Half Baths | 1.5 Acres | 6,462 Sq. Ft.

Explore the property:
landvest.com/listing/44402