Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. 
This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five original fireplaces, and 3 zone central heat and AC.  Additional conveniences include a mudroom, laundry room and a large screened porch where you’ll find yourself spending more time than anywhere else in the summer time. 
Two of the five bedrooms are on the first floor, including a private ensuite with a full bath. The home is notable for its unusually large and abundant windows, flooding the south-facing interior with natural light. The winding staircase is a sculptural centerpiece that greets you as you enter through the original front door. Renovations include a new roof over the porch, three modernized bathrooms, and updates throughout the first and second floors, all carefully designed to honor the home’s historic charm.
Outside you will find a lawn area and back yard patio that overlook perennial plantings including roses, hydrangeas and dogwood and a white picket fence that creates nice privacy.  Plus there is off-street parking for 2 cars. 
Located just one block from Main Street and two blocks from the Vineyard Haven ferry terminal , this prime location offers easy access to shopping and restaurants and the Tisbury Elementary School.  The town tennis courts are just a half-block away, and its a leisurely stroll to the town beach at Owen Park. 
This is a rare opportunity to own a piece of Vineyard Haven history, where timeless charm meets contemporary comfort.

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27 Spring Street

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THE BEST SEAT IN TOWN! This one-bedroom, one-bathroom condo offers incomparable, panoramic views of Vineyard Sound and the open ocean beyond, across the green expanse of Ocean Park with the Steamship Authority dock in the distance. Door to door, the ferry dock is 392 yards away. This perfect pied-a-terre is convenient to long stretches of beach, numerous shops, great and varied restaurants and the vibrant life of Oak Bluffs in the summertime. This is a completely renovated and updated Unit with high end finishes including solid mahogany doors and mahogany counter top center island. The property is beautifully landscaped and can be enjoyed year-round. It includes a coveted, off-street parking space. From the French doors in the Unit, you walk out onto a private, second floor, 7' x 21' porch from which you have a front row seat to watch the Oak Bluffs fireworks, band concerts in the gazebo and all the summer festivities on Ocean Park.  This is a rare opportunity to own a genuine piece of American history that cannot be duplicated. 

SHOWINGS WILL BEGIN ON SUNDAY, MAY 24TH WITH AN OPEN HOUSE FROM 1:00 TO 3:30PM

61 Ocean Avenue 4

SHOWINGS START MEMORIAL DAY WEEKEND. Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort.
Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark—an offering not to be missed.

61 Stonewall Road

Walk to the splendid sands of Lamberts Cove Beach as well as Seth's Pond for a dip and the nearby Inn for a romantic dinner. Fabulous location. The enchanting path to the white-rimmed cove is a mere 5-minute walk away. Main house with three bedrooms,large livingroom,many-windowed kitchen, artist;s studio and upstairs sun room. The newer two story Guest House is bright and inviting nestled in the lush landscape. Live in the guest house while renovating the main as you reward yourself with sunset picnics at the adjacent Land Bank beach.

318 Lamberts Cove Road

Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom home was built in 2014 and features over 4,000 square feet of thoughtfully designed living space across three levels. A welcoming mudroom, ideal for beach living, opens into a bright and expansive main living area featuring a spacious dining room, gourmet kitchen, and comfortable living room with oversized French doors leading to the pool patio. The first floor primary suite offers a luxurious spa-inspired bath and private French doors opening to a serene outdoor sitting area surrounded by lush landscaping. Four additional guest bedrooms are all generously sized, providing ample accommodations for family and friends. The finished lower level includes a media room, pool table area, and abundant storage space. Designed for effortless indoor-outdoor living, the backyard is a true Vineyard retreat featuring an oversized pool, outdoor kitchen, expansive stone patio, and a pool cabana complete with a full bath. A two-car garage includes unfinished space above with the unique potential to create a guest house, an exclusive feature permitted only for this property within the Nora’s Meadow association. A charming barn-style shed provides additional storage for kayaks, bikes, and boating equipment.  This rare offering combines luxury, privacy, and exceptional outdoor living in one of Edgartown’s most desirable neighborhoods, creating the ultimate Martha’s Vineyard retreat for generations to enjoy.

2 Noras Lane

Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach.  Magical expansive views of meadows, pond and ocean.  This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy.  A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside.  Close to nature, this seasonal home (April through October) was built in 1973 and evokes an earlier and simpler time. Use as is, build anew or significantly expand and/or modify the existing dwelling. There is a second abutting buildable lot with many options as well. Enjoyed as a summer retreat by one family for three generations, this is the only private home on Black Point Pond.  Walking into the generous, inviting wood panelled living room, the eye is drawn to the large windows opening to expansive views.  Rolling meadows, pond, and endless sea and sky… this blend of fields and water stretching into the horizon is the property's backyard. Gazing out from the two-story shingled home it's easy to imagine the legacy of this land, the family that grazed their sheep and for generations tended the land, and the more recent history over the last 50 years of family backyard cookouts, children catching crabs in the nearby creek and bike rides down the dirt road to idyllic Black Point Beach where expansive stretches of white sand run between Black Point Pond and the Atlantic Ocean. A short walking path leads from the house to a kayak rack on the pond.  Paddle and explore the pond or walk, bike, kayak or drive to nearby Black Point Beach.  These three lots (6 acres, 6 acres and 34 acres) are being offered together for the first time in over fifty years.  Two of the lots (Lots 1 and 2) are buildable while the third lot (the Meadow Lot) provides view protection for lots 1 and 2 and frontage on beautiful Black Point Pond.  A Black Point Beach lot is also included as part of this offering and will give a new owner membership in the Black Point Beach Association.  This is a rare opportunity to purchase an estate-sized parcel on Chilmark's south shore with enormous privacy, stunning views, private pond frontage, two buildable lots and access to one of the most spectacular beaches on Martha's Vineyard.

0, 36, 38 Black Point Road

Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom seasonal home sits on one lot with two detached studios alongside. Close to nature, this home was built in 1973 and evokes an earlier and simpler time. Enjoyed as a seasonal retreat by one family for three generations, this is the only private home on Black Point Pond. A short walking path leads from the house to a kayak rack on the pond. Paddle and explore Black Point Pond or walk, bike, kayak or drive to nearby Black Point Beach.   These three lots (6 acres, 6 acres and 34 acres) are being offered together for the first time in over fifty years. Two of the lots (Lots 1 and 2) are buildable while the third lot (the Meadow Lot) provides view protection for lots 1 and 2 and frontage on beautiful Black Point Pond.  A Black Point Beach lot is also included as part of this offering and will give a new owner membership in the private Black Point Beach Association. This is a rare opportunity to purchase an estate-sized parcel on Chilmark's south shore with enormous privacy, stunning views, private pond frontage, two buildable lots and access to one of the most spectacular beaches on Martha's Vineyard.

YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering more than 7,200 square feet of beautifully appointed living space created for the ultimate luxury: treasured time with family and friends. Inside, the home exudes warmth and sophistication with four wood-burning fireplaces, handsome hardwood and painted floors, custom millwork, built-ins, inviting gathering spaces, and sweeping views of Katama Bay from nearly every room. A rooftop widow’s walk crowns the home, offering breathtaking 360-degree vistas across the bay, dunes, tidal ponds, and surrounding grasslands.

One of the home’s most captivating features is the expansive screened and covered porch, extending nearly the full length of the house and overlooking the sparkling waters of Katama Bay. It is an idyllic setting for relaxed summer dinners, quiet afternoons with a book, lively games, or simply taking in the brilliant evening sunsets. With more than 320 feet of Katama Bay frontage, the property invites a true waterfront lifestyle, with exceptional opportunities for sailing, boating, paddleboarding, fishing, and clamming. Beyond the shoreline, Chappaquiddick offers a rare sense of peace and privacy, with miles of unspoiled beaches, nature trails, sand dunes, tidal ponds, and protected habitats to explore. An attached three-bay garage provides ample storage for an island car, watercraft, bicycles, beach gear, fishing equipment, and every essential for life by the water. Offered turnkey, the home includes hand-selected furnishings and accessories by interior designer Jon Hattaway of MJ Berries Design in Boston, whose vibrant colors, curated objects, and artful details bring character and delight to every room. Enjoy the property exactly as it is, or make it your own and create a signature coastal haven. At once elegant, welcoming, and deeply connected to its extraordinary setting, this private Katama Bay retreat is designed for effortless waterfront living.

25 Lelands Path

A truly rare offering on Oyster Pond Rd. This property offer rights to boating and swimming in the pond plus a rare easement to access   “The Barrier Beach", on the south shore. Access to the south beach is by boating down Oyster Pond.This beach access is a spectacular addition to this property. The land is 4.4 acres, very quiet and  bordered by exceptional homes. Privacy abounds.  This contemporary 1980’s home is in excellent condition. It offers four bedrooms and three bathrooms. Though never rented, it could would serve as an excellent summer rental investment.  This property is being sold “turn key” with everything included.

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82 Oyster Pond Road

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck.  There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and apple! The property is gated and entirely enclosed with deer fencing. There is also a storage shed and a detached garage. Easy access to Menemsha, Chilmark Store and Chilmark Beaches.

26 Bijahs Way

Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is  two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system.

47 Winemack Avenue

This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views of open pastures, ancient stone walls, woodlands, and the Atlantic beyond. The three-bedroom residence features an open-concept layout that seamlessly connects indoor living spaces to a full-length deck—perfect for entertaining or simply soaking in the peaceful surroundings. Recent updates include new kitchen appliances and a high-efficiency heat pump system with central air conditioning. A true highlight of this property is the land itself. Crisscrossed with well-maintained trails, it invites exploration through meadows, forest, streams, and even a tranquil pond. This property has an extraordinary sense of place and feels like a private piece of up-island history—rich in character, natural beauty, and possibility. Six-bedroom septic installed. Abutting 3.9-acre building parcel available.

44 Cencelle

This handsome, newly renovated classic Cape, is nestled on a private 1.38 acre lot in the sought after Lagoon Estates community. The property has been thoughtfully renovated with two new kitchens, 5 new bathrooms, 4-bedrooms (two ensuite), all new windows and new flooring on first floor. It's seamless floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace to the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. The first floor includes one of the ensuite bedrooms and a large screened in porch off the dinning room. The 2nd floor includes two large bedrooms (one ensuite), a second full bathroom and new washer/dryer. The attached 1-bedroom apartment includes  living/dining/kitchen area, washer/dryer, heat/AC and sits above a large 2-car garage with mud room and lots of storage space. To the side of the garage is a large separate bonus/variable use room with heat/AC that could be used as an office or game family room. Full unfinished basement has three additional rooms that could be used as a family room, studio/workshop and grow room. Property includes a spacious rear patio and deck with access off both the kitchen and screened in porch, as well as an outdoor shower and parking for several cars in the driveway. The lot is large enough in this R3 zone for an in-ground pool behind the garage. Assessed value does not reflect extensive 2026 renovations. Please note: Newly seeded lawn areas have been touched up and furniture in several rooms is virtually staged and noted in photos. Title V septic passed inspection 5/12/25 and in-ground propane tank pressured tested in 2025.

44 Tiffany Drive

Waterfront house and guest house with a private dock on Menemsha Pond.  This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. 
 Built and cared for over four generations by an
Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the Southeast, watch 
Menemsha Pond ebb and flow around sandy islands with 120 degrees of unobstructed view. To the Northwest, elevated rooms look out over the sunset on Menemsha harbor.
A secluded lawn is partially shaded by healthy blue spruce and bordered by an ancient stone wall. To the south, the dock traverses the estuary into a private cove
opening up to the main pond and the ocean. A secure environment surrounded by water
on three sides.  The property is only a short walk to the Menemsha harbor, beach, boutique
galleries, and fresh seafood restaurants—from the daily catch from local fish markets to the
fine dining of the Home Port. Southern orientation provides sun all-day to both the house
and the guest house. Year-round water and new 5-bedroom Title-5 compliant septic.
Unique remodeling and expansion options compared with other waterfront Island
property due to the existing height, large attic with views, and a lower level with tremendous natural light allowing for valuable future living square footage.
You are welcome to continue the legacy of this extraordinary real estate.

34 Edys Island Way

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay, or taking a scenic shortcut to South Beach, this waterfront setting offers the very best of Vineyard living. Completing the property is a generous 2-car garage

103 Edgartown Bay Road

Edgartown opportunity! Bring your vision to this two-bedroom, one-bath ranch situated close to the heart of downtown Edgartown. This property presents a rare chance to create value in a highly sought-after location.

Just minutes to downtown, with off-street parking for three vehicles, the home features functional single-level living, including a living area, kitchen, two bedrooms, and a study/office. A full unfinished basement provides additional space for storage or future use.

The property requires renovation; however, it offers an entry point into the Edgartown market sought after by investors, builders, and end users alike.

Being offered as-is, this estate sale property is ready for its next chapter. Town sewer tie-in is available, allowing for potential expansion to a four-bedroom home, subject to R5 zoning setbacks and appropriate town permitting. Please note that estate procedures regarding offers will apply.

51 Chase Road

Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages.
From the moment you step through the welcoming vestibule, it’s clear this is a home with stories to tell. Wood plank floors, rich woodwork, and generously proportioned rooms speak to its heritage, while thoughtful updates have introduced an easy, understated luxury throughout. The kitchen has been beautifully remodeled with custom cabinetry and stone countertops. Light pours through oversized windows into gracious living and dining spaces, with a fireplace adding warmth and character to the living room. Upstairs, the primary suite offers garden views and a peaceful retreat, while guest bedrooms retain period charm with airy, sunlit appeal.
Outside, the grounds feel secluded and mature—a private world behind an original wrought iron gate. Paths wind through perennial gardens and wide lawns, while a porch and flagstone patio invite lingering afternoons in the dappled shade. A charming one-bedroom guest cottage sits tucked away from the main house, offering flexibility for guests, work-from-home, or rental income. This home has long been cherished by artists, collectors, and careful stewards—each adding their layer to the property’s quiet patina. Just a short stroll to the ferry, shops, restaurants, library, and beach, 139 Main Street is a rare find: a truly in-town retreat that feels a world apart.
This expansive main house offers flexible living with six rooms currently used as bedrooms, including a separate guest suite. The property has a 5-bedroom septic system per Title 5.

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139 Main Street

A storybook setting in beautiful Pilot Hill. 
For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale. Set on nearly eight acres, this unique seven bedroom estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool house, an art studio, and a carriage house with room for three cars, plus a second studio above.
The main home dates from 1730 and has been lovingly restored over the years.  Carefully preserved original details—such as hand-painted Siberian elm floors, gunstock posts, a Dutch door, and four fireplaces—coexist with thoughtful upgrades throughout. The main residence offers five bedrooms and four plus one half bathrooms, a large kitchen, separate dining room, cozy living room, another formal living room with fireplace and a screened porch that overlooks the heated saltwater pool and grounds.
The pool house adds two more bedrooms, bathroom, and a large double height living room that overlooks the meadow.
The grounds evoke an arboretum-like feel, with mature trees, open meadows, stone walls, a picturesque pond, babbling brook and perennial gardens.  Stroll to the farm for fresh produce and flowers or to the beach for an evening walk.  This is a natural haven in a magical setting, yet just minutes from Vineyard Haven's shops, restaurants, and the ferry.

180 Pilot Hill Farm Road

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47 Winemack Avenue

44 Cencelle

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180 Pilot Hill Farm Road