New Listings

Address: 105 Whalers Walk    Town: Edgartown    Link ID: 44346

Price: $2,495,000

Property Description:
Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to... Click here for more details

Address: 60 Crocker Drive    Town: Edgartown    Link ID: 44200

Price: $2,300,000

Property Description:
Nestled in the heart of Katama, 60 Crocker Drive offers a decerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 4 bedrooms, you can renovate the existing structures or start from scratch to make it your own. Th... Click here for more details

Address: 51 Summer Street    Town: Vineyard Haven    Link ID: 44326

Price: $1,395,000

Property Description:
Beautifully renovated and full of charm, this Vineyard Haven home combines stylish design with modern function in one of the island’s most sought-after neighborhoods. Every space has been thoughtfully planned to offer flexibility, comfort, and light, while maintaining the relaxed character that de... Click here for more details

Address: 7 Overview Lane    Town: Oak Bluffs    Link ID: 44341

Price: $5,100,000

Property Description:
A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build... Click here for more details

Address: 79 Beach Road    Town: Vineyard Haven    Link ID: 44193

Price: $1,799,000

Property Description:
TISBURY MARKETPLACE offers an active and well-established setting for this beloved eatery. The year 'round destination hub draws proven foot traffic and a healthy commercial environment. Rocco’s Pizzeria anchors the corner of the water view plaza with sustained history and a devoted following. Ope... Click here for more details

Address: 393 Lighthouse Road    Town: Aquinnah    Link ID: 44338

Price: $1,599,000

Property Description:
Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Liv... Click here for more details

Address: 0 State Road    Town: Vineyard Haven    Link ID: 44340

Price: $2,000,000

Property Description:
1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

Address: 31 North Road    Town: Chilmark    Link ID: 44180

Price: $1,200,000

Property Description:
Surrounded by three-season perennial gardens, this sun-filled two bedroom cottage offers an airy open floor plan with high ceilings that create an impressive sense of space. Natural light pours in through four skylights and classic 8 over 8 windows, while a deck off the side and rear of the home pro... Click here for more details

Address: 237 Lagoon Pond Road    Town: Vineyard Haven    Link ID: 44301

Price: $2,250,000

Property Description:
Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area. Set on a gentle ris... Click here for more details

Address: 25 Bold Meadow Road    Town: Edgartown    Link ID: 44319

Price: $3,450,000

Property Description:
This distinguished home in the Bold Meadow neighborhood of Edgartown offers so much. Immediately upon entering one is captivated by the light and bright interiors showcased by the banks of south-facing windows in the cathedral-ceilinged Great Room. This continues through to the new sunroom. The prop... Click here for more details

Address: 0 North Road/15 Belhaven Way    Town: Chilmark    Link ID: 44325

Price: $1,325,000

Property Description:
Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Mi... Click here for more details

Address: 20 Edson Forest Road    Town: West Tisbury    Link ID: 44269

Price: $3,950,000

Property Description:
Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. A full restoration of this this three-bedroom house (with six-bedroom septi... Click here for more details

Address: 26 Flint Hill Road    Town: West Tisbury    Link ID: 44135

Price: $1,645,000

Property Description:
Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with... Click here for more details

Address: 12 Wheelhouse Way    Town: Oak Bluffs    Link ID: 44330

Price: $1,095,000

Property Description:
Charming, custom-built, 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, year-round ferries, and miles of ancient way trails through acres of conservation land. Well-maintained with many decorative details, features... Click here for more details

Address: 309 Barnes Road    Town: Oak Bluffs    Link ID: 44257

Price: $3,125,000

Property Description:
Your Vineyard summer begins the moment you arrive. Fully furnished, renovated waterfront retreat offers 175' of private shorefront on Lagoon Pond — one of Martha's Vineyard's most coveted settings. Taken to the studs in 2022 and reimagined by architect Ramsay Gourd, this bright coastal escape feat... Click here for more details

Address: 34 Windemere Road    Town: Oak Bluffs    Link ID: 44300

Price: $2,579,000

Property Description:
Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard loca... Click here for more details

Address: 834 State Road    Town: Aquinnah    Link ID: 44317

Price: $1,375,000

Property Description:
Gorgeous hilltop water view property looks out over the Atlantic Ocean. This building site is optimal for a passive or active solar home with ideal south-west orientation for panels and maximizing light. Great breezes come from the southwest keeping down the mosquito interactions. The driveway app... Click here for more details

Address: Off. Moshup Trail    Town: Aquinnah    Link ID: 44306

Price: $330,000

Property Description:
Tucked along the south shore of Aquinnah on Martha’s Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects... Click here for more details

Address: 27 Clambelly Road    Town: Chilmark    Link ID: 44318

Price: $3,395,000

Property Description:
A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. ... Click here for more details

Address: 25 Pennacook Avenue    Town: Oak Bluffs    Link ID: 44285

Price: $2,180,000

Property Description:
A unique offering in the heart of the historic Copeland District of downtown Oak Bluffs. This cherished main residence and guest house, embody the timeless charm that defines this beloved community. Just minutes from Circuit Ave, the ferries and harbor, and a block from Inkwell Beach. This home invi... Click here for more details

Address: 98 Farm Neck Way    Town: Oak Bluffs    Link ID: 44316

Price: $3,995,000

Property Description:
Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views... Click here for more details

Address: 261 Sandpiper Lane    Town: Vineyard Haven    Link ID: 44304

Price: $1,250,000

Property Description:
END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation... Click here for more details

Address: 68 Front Street    Town: Oak Bluffs    Link ID: 44077

Price: $1,795,000

Property Description:
Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan wit... Click here for more details

Address: 26 Sea Glen Road    Town: Oak Bluffs    Link ID: 44199

Price: $1,625,000

Property Description:
Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, ... Click here for more details

Address: 31 Temahigan Avenue    Town: Oak Bluffs    Link ID: 44308

Price: $975,000

Property Description:
HEAD START BUILD OPPORTUNITY IN OAK BLUFFS WITH POTENTIAL WATER VIEWS OF THE VINEYARD HAVEN HARBOR. Rare opportunity to secure a prime parcel in a sought-after Oak Bluffs location with valuable groundwork already in place and potential views of Vineyard Haven Harbor. The property features an existi... Click here for more details

Address: 119 North William Street    Town: Vineyard Haven    Link ID: 44260

Price: $950,000

Property Description:
A rare opportunity to own a historic Martha’s Vineyard home just moments from town. Originally built in 1900, this charming 3-bedroom, 1.5 bath home in Vineyard Haven offers 1,395 sq ft of living space on a 0.20-acre lot, blending classic island character with an unbeatable location! Enjoy the eas... Click here for more details

Address: 385 Barnes Road    Town: Oak Bluffs    Link ID: 42465

Price: $5,495,000

Property Description:
SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living s... Click here for more details

Address: 56 North Summer Street    Town: Edgartown    Link ID: 44194

Price: $21,500,000

Property Description:
A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined... Click here for more details

Address: 26 Union Court    Town: Vineyard Haven    Link ID: 44294

Price: $1,625,000

Property Description:
Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a t... Click here for more details

Address: 38 Fire Tower Road    Town: West Tisbury    Link ID: 44299

Price: $1,425,000

Property Description:
The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's eas... Click here for more details

Address: 12 Lobsterville Road    Town: Aquinnah    Link ID: 44289

Price: $1,850,000

Property Description:
12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and gras... Click here for more details

Address: 62 North Summer Street    Town: Edgartown    Link ID: 44293

Price: $5,875,000

Property Description:
Village dreams come true… STUNNINGLY CRAFTED, **this four-bedroom five bath property in Edgartown Village with Garage is truly a rare find! Situated on a corner lot just two blocks north of Main Street and two blocks from the Harbor, it features walking convenience and luxury in one package. Main ... Click here for more details

Address: 23 Calebs Common Lane    Town: Edgartown    Link ID: 44198

Price: $650,000

Property Description:
CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create... Click here for more details

Address: 3 Somerset Lane    Town: Edgartown    Link ID: 44089

Price: $6,595,000

Property Description:
Introducing 3 Somerset Lane, one of 4 newly built residences in an exclusive new enclave in the heart of Katama. This beautifully crafted new construction home, built by respected Island builder Adam Moran Construction, showcases nearly 4,000 square feet of thoughtfully designed living space, execu... Click here for more details

Address: 205 South Road    Town: Chilmark    Link ID: 44028

Price: $5,650,000

Property Description:
CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 s... Click here for more details

Address: 370 Lighthouse Road    Town: Aquinnah    Link ID: 44244

Price: $3,375,000

Property Description:
Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes wit... Click here for more details

Address: 5 Lenssen Way & 63 Eel Pond Lane    Town: Edgartown    Link ID: 44196

Price: $4,200,000

Property Description:
A rare opportunity to create your dream Vineyard estate in a unique setting with the rural feel of up-Island and the easy convenience of, and proximity to, Edgartown Village. Just a 1/2 mile walk, bike or drive to the top of Lower Main Street, the vacant lot rests on a private, dirt road off prestig... Click here for more details

Address: 94 Weaver Lane    Town: Vineyard Haven    Link ID: 44191

Price: $4,500,000

Property Description:
Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its best. Set on 2.25 secluded acres, spectacular panoramic views stretch across the shimmering waters of Lagoon Pond, a private haven for kaya... Click here for more details

Address: 78 Hammett Road    Town: Chilmark    Link ID: 44277

Price: $6,750,000

Property Description:
Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedro... Click here for more details

Address: 0 Jeffers Way    Town: Aquinnah    Link ID: 44222

Price: $785,000

Property Description:
Nestled within the serene landscape of Aquinnah, this 3.8-acre parcel offers a unique blend of natural beauty and historical significance. Bordered by ancient stone walls and mature vegetation, the elevated terrain provides a bucolic setting for a private residence. Already in place is a private wel... Click here for more details

Address: 37 Circuit Avenue    Town: Oak Bluffs    Link ID: 44276

Price: $899,000

Property Description:
In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This cond... Click here for more details

Address: 37 Circuit Avenue    Town: Oak Bluffs    Link ID: 44275

Price: $869,000

Property Description:
In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surro... Click here for more details

Address: 2 Bold Meadow Road    Town: Edgartown    Link ID: 44240

Price: $2,950,000

Property Description:
Nestled on a private 1.7-acre parcel in the peaceful Bold Meadow neighborhood, this classic expanded Cape offers a perfect blend of comfort, space, and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from all tha... Click here for more details

Address: 17 John Wesley Avenue    Town: Oak Bluffs    Link ID: 44267

Price: $1,795,000

Property Description:
Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by a... Click here for more details

Address: 2 Lexington Avenue    Town: Edgartown    Link ID: 44051

Price: $7,950,000

Property Description:
NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed new construction by Morgan Studio, a husband-and-wife–led boutique design firm. A turn-key offering for elevated indoor-outdoor living, the residence features soaring ceilings, a fluid floor plan with multiple gatherin... Click here for more details

Address: 95 Hines Point Road    Town: Vineyard Haven    Link ID: 44144

Price: $4,695,000

Property Description:
A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high cei... Click here for more details

Address: 29 Majors Cove Lane    Town: Edgartown    Link ID: 44080

Price: $4,675,000

Property Description:
First time on the market in 26 years, this beautiful waterfront family compound sits at the end of Majors Cove Lane in a private and peaceful setting with sweeping and expansive water views and a private 85’ boat dock shared with only one neighboring property. The property directly fronts Sengekon... Click here for more details

Address: 217 Barnes Road    Town: Oak Bluffs    Link ID: 44172

Price: $5,695,000

Property Description:
This exceptional waterfront estate offers unmatched panoramic views from house and guest house with extraordinary privacy on a nearly two acre setting rarely found in this coveted Oak Bluffs location. Commanding sweeping vistas of Lagoon Pond, Vineyard Haven, Hines Point, the iconic drawbridge, Vine... Click here for more details

Address: 50 Hidden Cove Road    Town: Oak Bluffs    Link ID: 44263

Price: $2,400,000

Property Description:
Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovi... Click here for more details

Address: 6 Stone Pound Way    Town: Oak Bluffs    Link ID: 44033

Price: $1,399,000

Property Description:
The ambience of this tranquil Waterfront community will inspire you immediately. This spacious 3 bedroom w/oversized family room home is affordably priced. The sun shines in the charming living room w/ brick fireplace, Palladian side windows, Rennai gas monitor & attractive hardwood floors. The amp... Click here for more details

Address: 81 Whalers Walk    Town: Edgartown    Link ID: 44085

Price: $2,350,000

Property Description:
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 be... Click here for more details

Address: 110 Clover Hill Drive    Town: Vineyard Haven    Link ID: 44254

Price: $1,575,000

Property Description:
Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment i... Click here for more details

Address: 111 Charles Neck Way    Town: West Tisbury    Link ID: 44256

Price: $1,599,000

Property Description:
Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert’s Cove Beach. Th... Click here for more details