Recent Price Changes
4 Cormorant Circle Edgartown
New Price: $1,875,000 | Original Price: $1,925,000 | Change: -2.6%
Property Description:
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 Katam... Click here for more details
34 Windemere Road Oak Bluffs
New Price: $2,495,000 | Original Price: $2,579,000 | Change: -3.3%
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
12 Boldwater Road Edgartown
New Price: $9,500,000 | Original Price: $9,950,000 | Change: -4.5%
Property Description:
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 ... Click here for more details
11 Stanley Street Oak Bluffs
New Price: $1,195,000 | Original Price: $1,255,000 | Change: -4.8%
Property Description:
Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac
Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous .35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend... Click here for more details
41 Renear Street Vineyard Haven
New Price: $997,000 | Original Price: $1,150,000 | Change: -13.3%
Property Description:
Some properties you visit, and some properties you experience. Tucked behind mature gardens and a lush natural landscape, 41 Renear Street is a hidden Vineyard treasure — a classic 1927 cottage where timeless character, village convenience, and the beauty of the outdoors come together.
Set on a g... Click here for more details
64 Christiantown Road West Tisbury
New Price: $3,249,000 | Original Price: $3,495,000 | Change: -7.0%
Property Description:
This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchore... Click here for more details
150 Field View Lane West Tisbury
New Price: $1,495,000 | Original Price: $1,600,000 | Change: -6.6%
Property Description:
A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-... Click here for more details
2 Other House Road Chilmark
New Price: $2,250,000 | Original Price: $2,500,000 | Change: -10.0%
Property Description:
Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with... Click here for more details
8 Beach Plum Meadows Edgartown
New Price: $6,900,000 | Original Price: $7,250,000 | Change: -4.8%
Property Description:
BEACH PLUM MEADOWS: ARCHITECTURAL KATAMA COMPOUND NEAR SOUTH BEACH. Set on more than 1.6 acres in the coveted Beach Plum Meadows enclave, this distinctive property combines classic coastal architecture, private compound living, and distant views across the Katama plains to the Atlantic Ocean—all l... Click here for more details
528 Main Street Vineyard Haven
New Price: $1,395,000 | Original Price: $1,800,000 | Change: -22.5%
Property Description:
Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a priv... Click here for more details
17 Chockers Lane Chilmark
New Price: $4,950,000 | Original Price: $5,500,000 | Change: -10.0%
Property Description:
Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring.
Inside, hand-painted floors and a w... Click here for more details
81 Whalers Walk Edgartown
New Price: $2,125,000 | Original Price: $2,350,000 | Change: -9.6%
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
41 Hagerty Drive Vineyard Haven
New Price: $5,750,000 | Original Price: $5,950,000 | Change: -3.4%
Property Description:
Welcome to your Vineyard dream home in the highly sought-after West Chop neighborhood. This exceptional brand-new construction offers 6 bedrooms, 6 full baths, and 1 half bath, thoughtfully designed with timeless coastal elegance and modern luxury.
Filled with natural light, the home’s bright and... Click here for more details
139 Chappaquiddick Road Edgartown
New Price: $10,750,000 | Original Price: $12,250,000 | Change: -12.2%
Property Description:
Overlooking the active waters of the outer harbor and set just off the paved road, this remarkable waterfront estate occupies one of Chappaquiddick’s most spectacular stretches of beach, just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village. A rare and t... Click here for more details
39 Ferro Way Vineyard Haven
New Price: $1,390,000 | Original Price: $1,488,000 | Change: -6.6%
Property Description:
Tucked away on a quiet cul-de-sac, this beautifully maintained multi-family property offers the perfect blend of privacy, flexibility, and convenience. Built in 2020, the home encompasses 2,884 square feet of thoughtfully designed living space, featuring a total of 5 bedrooms and 4 full bathrooms. T... Click here for more details
96 Dunham Avenue Vineyard Haven
New Price: $849,000 | Original Price: $949,000 | Change: -10.5%
Property Description:
NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dinin... Click here for more details
35 Double Ox Road Oak Bluffs
New Price: $675,000 | Original Price: $749,500 | Change: -9.9%
Property Description:
GOING, GOING… GONE!
This is the LAST 3-bedroom lot available in Cluster C.
12 lots SOLD
9 homes already built.
Welcome to Lagoon Ridge Oak Bluffs’ newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, ... Click here for more details
7 Ploughshare Lane Oak Bluffs
New Price: $1,399,000 | Original Price: $1,599,000 | Change: -12.5%
Property Description:
Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layou... Click here for more details
19 Perkins Avenue Oak Bluffs
New Price: $799,000 | Original Price: $825,000 | Change: -3.2%
Property Description:
Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries... Click here for more details
33 Alyssa Lane Vineyard Haven
New Price: $1,200,000 | Original Price: $1,495,000 | Change: -19.7%
Property Description:
MOTIVATED SELLER. Please note substantial PRICE CHANGE. Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area ... Click here for more details
10 Woodhaven Drive Edgartown
New Price: $2,500,000 | Original Price: $2,650,000 | Change: -5.7%
Property Description:
Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equ... Click here for more details
135 Mayflower Lane Vineyard Haven
New Price: $1,895,000 | Original Price: $1,995,000 | Change: -5.0%
Property Description:
Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential.
The main residence features three bedrooms and an inviting open-concep... Click here for more details
5 Paula Avenue Vineyard Haven
New Price: $1,299,000 | Original Price: $1,400,000 | Change: -7.2%
Property Description:
Discover the opportunity to make this spacious Vineyard Haven home your own, ideally located on the desirable lower end of Lambert’s Cove Road. Just across from Pilot Hill Road and approximately one mile from the pristine shores of Lambert’s Cove Beach, this well-positioned property offers a won... Click here for more details
22 Old Lighthouse Road Vineyard Haven
New Price: $1,499,000 | Original Price: $1,650,000 | Change: -9.2%
Property Description:
This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels ... Click here for more details
33 Vineyard Avenue Oak Bluffs
New Price: $1,695,000 | Original Price: $1,995,000 | Change: -15.0%
Property Description:
33 Vineyard Avenue Oak Bluffs offers immense investment and flexible living opportunity with TWO UNITS on a fully irrigated appx 5200 sq ft lot.
Fully gut renovated with all BRAND NEW; electric, plumbing, roof, septic system, and structural engineering - highlighted by elevated finishes, classic ae... Click here for more details
99 Ocean Avenue Oak Bluffs
New Price: $3,700,000 | Original Price: $3,975,000 | Change: -6.9%
Property Description:
A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ... Click here for more details
43 North Slope Lane Chilmark
New Price: $1,649,000 | Original Price: $1,799,999 | Change: -8.4%
Property Description:
Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while rem... Click here for more details
37 Dodgers Hole Road Edgartown
New Price: $1,175,000 | Original Price: $1,249,900 | Change: -6.0%
Property Description:
This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designe... Click here for more details
32 Norton Orchard Road Edgartown
New Price: $1,850,000 | Original Price: $2,100,000 | Change: -11.9%
Property Description:
Discover this turnkey Edgartown home in a prime location near downtown dining and shopping, Edgartown Golf Club, and popular beaches. The refreshed interior features modern flooring, modern LED lighting, bathroom, and a bright kitchen with dark green granite countertops, tall windows, and a vaulted ... Click here for more details
25 Fulling Mill Road Chilmark
New Price: $1,995,000 | Original Price: $2,450,000 | Change: -18.6%
Property Description:
Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main... Click here for more details
50 Canonicus Avenue Oak Bluffs
New Price: $825,000 | Original Price: $995,000 | Change: -17.1%
Property Description:
Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. ... Click here for more details
217 Barnes Road Oak Bluffs
New Price: $4,450,000 | Original Price: $5,695,000 | Change: -21.9%
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
2 Lexington Avenue Edgartown
New Price: $7,695,000 | Original Price: $7,950,000 | Change: -3.2%
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
323 County Road Oak Bluffs
New Price: $1,095,000 | Original Price: $1,225,000 | Change: -10.6%
Property Description:
This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or p... Click here for more details
74 Chase Lane & 25 Norton Ave Land Lot Vineyard Haven
New Price: $905,000 | Original Price: $945,000 | Change: -4.2%
Property Description:
Great Location Turnkey Cape Cod style year round home well maintained on a private dead end road close to Tashmoo Landing. New roof 2025, new windows, basement insulation replaced. A solid well built home ready for new owners to enjoy! Open concept kitchen to dining room. Three bedrooms and one full... Click here for more details
21 Davis Street Vineyard Haven
New Price: $2,325,000 | Original Price: $2,925,000 | Change: -20.5%
Property Description:
Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home encompassing 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restora... Click here for more details
59 Tuckernuck Avenue Oak Bluffs
New Price: $2,595,000 | Original Price: $2,650,000 | Change: -2.1%
Property Description:
Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting ope... Click here for more details
26 Bijahs Way Chilmark
New Price: $2,195,000 | Original Price: $2,495,000 | Change: -12.0%
Property Description:
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 heati... Click here for more details
40 Hidden Cove Road Oak Bluffs
New Price: $1,495,000 | Original Price: $1,595,000 | Change: -6.3%
Property Description:
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, m... Click here for more details
40 Hidden Cove Road Oak Bluffs
New Price: $1,495,000 | Original Price: $1,595,000 | Change: -6.3%
Property Description:
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, m... Click here for more details
36 Hines Point Road Vineyard Haven
New Price: $2,995,000 | Original Price: $3,100,000 | Change: -3.4%
Property Description:
HINES POINT WATERFRONT GEM with 85 feet of frontage on the Lagoon, offering ever-changing water views and the perfect vantage point to watch the Steamship Authority ferries arrive in Vineyard Haven Harbor. Enjoy the charming, timeless cottage with a one-car garage as an idyllic summer retreat, or br... Click here for more details
20 Hidden Cove Road Oak Bluffs
New Price: $1,595,000 | Original Price: $1,625,000 | Change: -1.8%
Property Description:
Hidden Cove Retreat — Water Access, Tennis & Pickleball
Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat d... Click here for more details
45 Quenames Road Chilmark
New Price: $1,125,000 | Original Price: $1,575,000 | Change: -28.6%
Property Description:
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two bedrooms, a full bath with shower, an enormous three... Click here for more details
47 Quenames Road Chilmark
New Price: $1,150,000 | Original Price: $1,575,000 | Change: -27.0%
Property Description:
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A ... Click here for more details
76 Washque Avenue Edgartown
New Price: $2,299,000 | Original Price: $2,575,000 | Change: -10.7%
Property Description:
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... Click here for more details
14 Cow Bay Road Edgartown
New Price: $14,000,000 | Original Price: $15,000,000 | Change: -6.7%
Property Description:
Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of pri... Click here for more details
38 Fire Tower Road West Tisbury
New Price: $1,350,000 | Original Price: $1,425,000 | Change: -5.3%
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
37 Bijahs Way Chilmark
New Price: $1,245,000 | Original Price: $1,325,000 | Change: -6.0%
Property Description:
FRESHLY BRUSH CUT and EASY to WALK! This quiet and lovely four-and-a-half-acre lot in Chilmark is READY-TO-BUILD. The land has a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, ... Click here for more details
14 Thayer Street Edgartown
New Price: $10,995,000 | Original Price: $12,925,000 | Change: -14.9%
Property Description:
An exceptional offering in the heart of Edgartown Village, 14 Thayer Street presents the rare combination of estate-scale grounds, privacy, and an in-town location. Set across an extraordinary 0.62-acre double lot, the property unfolds as a private retreat just moments from the harbor, shops, galler... Click here for more details
44 Tiffany Drive Oak Bluffs
New Price: $2,595,000 | Original Price: $3,245,000 | Change: -20.0%
Property Description:
Tucked away in a serene setting and set on 1.38 private acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq. ft. of living space with plenty of room for a backyard pool. The main portion of the house includes a gourmet kitchen, multiple entertaining areas including living room, fam... Click here for more details
299 Daggett Avenue Unit A Vineyard Haven
New Price: $1,095,000 | Original Price: $1,249,000 | Change: -12.3%
Property Description:
This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was a... Click here for more details
30 Water Gate Road Vineyard Haven
New Price: $3,495,000 | Original Price: $4,695,000 | Change: -25.6%
Property Description:
Set privately in one of Vineyard Haven’s most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and ready access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for both gathering and quiet re... Click here for more details
99 The Boulevard Edgartown
New Price: $2,455,000 | Original Price: $2,475,000 | Change: -0.8%
Property Description:
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 ma... Click here for more details
2 Bold Meadow Road Edgartown
New Price: $2,850,000 | Original Price: $2,950,000 | Change: -3.4%
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
41 Edgartown Vineyard Haven Road Vineyard Haven
New Price: $1,299,000 | Original Price: $1,399,000 | Change: -7.1%
Property Description:
Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with r... Click here for more details
60R Carol Lane Oak Bluffs
New Price: $785,000 | Original Price: $794,000 | Change: -1.1%
Property Description:
Charming Oak Bluffs Retreat Near Town
Tucked away down a quiet lane just moments from downtown Oak Bluffs, this charming home offers the perfect blend of simplicity, comfort, and convenience. Set on just over 8,400 square feet, the property provides easy, single-story living in a sought-after Oak Bl... Click here for more details
261 Sandpiper Lane Vineyard Haven
New Price: $1,175,000 | Original Price: $1,250,000 | Change: -6.0%
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
12 East Pasture Road Aquinnah
New Price: $3,100,000 | Original Price: $3,495,000 | Change: -11.3%
Property Description:
This elegant architectural home is set within a lovely rolling meadow on four and a half generous acres, surrounded by stone walls, blue sky, and tranquility at all times of year. 12 East Pasture is a peaceful retreat on the westernmost side of Martha's Vineyard, known for the beautiful beaches and ... Click here for more details
29 Scotchmans Lane West Tisbury
New Price: $1,289,000 | Original Price: $1,399,000 | Change: -7.9%
Property Description:
Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing d... Click here for more details
21 island Inn Road Oak Bluffs
New Price: $389,000 | Original Price: $527,500 | Change: -26.3%
Property Description:
Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommoda... Click here for more details
31 Josiah Sachem Way West Tisbury
New Price: $3,790,000 | Original Price: $4,650,000 | Change: -18.5%
Property Description:
Open House Sat Oct 10th 10:30A-12:30P.
Some properties are a house. This one is a world.
Set on more than three private acres along the gentle slopes of Indian Hill, this is a true multi-dwelling compound, purpose-built for the way people actually want to live now: together, apart, and on their own ... Click here for more details
22 Oklahoma Avenue Vineyard Haven
New Price: $1,250,000 | Original Price: $1,445,000 | Change: -13.5%
Property Description:
HOUSE + APARTMENT NEAR LAGOON! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean and bright, move-in ready property features a 3 BR, 1 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-deman... Click here for more details
47 Winemack Avenue Oak Bluffs
New Price: $1,100,000 | Original Price: $1,199,000 | Change: -8.3%
Property Description:
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 fl... Click here for more details
99 Old Purchase Road Edgartown
New Price: $1,775,000 | Original Price: $1,850,000 | Change: -4.1%
Property Description:
Set at the end of a cul-de-sac, this property offers a peaceful setting on .71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike ... Click here for more details
146 Quenames Road Chilmark
New Price: $32,500,000 | Original Price: $35,000,000 | Change: -7.1%
Property Description:
Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintain... Click here for more details
37 Circuit Avenue Oak Bluffs
New Price: $879,000 | Original Price: $899,000 | Change: -2.2%
Property Description:
Intown Oak Bluffs Condo with Panoramic Rooftop Views
Discover the charm of island living in this exceptional 2-bedroom, 1-bath condo in the heart of Oak Bluffs. Just under 1,000 square feet, this comfortable residence combines character, comfort, and an unbeatable in-town location.
Step inside to an... Click here for more details
37 Circuit Avenue Oak Bluffs
New Price: $849,000 | Original Price: $869,000 | Change: -2.3%
Property Description:
In-Town Oak Bluffs Condo with Panoramic Water Views
Experience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space.
The condo features one generously sized bedroom plus a separate sleep nook, offering flex... Click here for more details
6 Brewster Avenue Oak Bluffs
New Price: $3,100,000 | Original Price: $3,450,000 | Change: -10.1%
Property Description:
Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while prese... Click here for more details
15 Twenty First Street North Edgartown
New Price: $2,590,000 | Original Price: $2,950,000 | Change: -12.2%
Property Description:
Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities.
Set on over a half-acre, the property features a main residence and a detached guest ho... Click here for more details
233 East Chop Drive Oak Bluffs
New Price: $6,900,000 | Original Price: $7,550,000 | Change: -8.6%
Property Description:
Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with... Click here for more details
19 Locust Lane Aquinnah
New Price: $5,900,000 | Original Price: $6,950,000 | Change: -15.1%
Property Description:
There is a town at the end of Martha's Vineyard. The road narrows, the houses thin, and the light changes. This is Aquinnah; the westernmost town, clay cliffs, a lighthouse, and one of the smallest year-round populations on the Vineyard. Compound-scale offerings rarely come to market here. 19 Locust... Click here for more details
44 Prices Way Edgartown
New Price: $1,395,000 | Original Price: $1,495,000 | Change: -6.7%
Property Description:
CONTEMPORARY ISLAND RETREAT. As a smart opportunity for Vineyard buyers seeking a low-maintenance Island home close to Edgartown Village, this contemporary home offers easy access to shopping, services, and the bicycle path connecting the three down-Island towns. Whether used as a year-round residen... Click here for more details
237 Lagoon Pond Road Vineyard Haven
New Price: $1,999,500 | Original Price: $2,250,000 | Change: -11.1%
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
104 Pond View Farm Road West Tisbury
New Price: $4,300,000 | Original Price: $4,800,000 | Change: -10.4%
Property Description:
Two homes on over three acres of waterfront on the beautiful and coveted Tisbury Great Pond. This remarkable waterfront property offers a rare opportunity to own a serene compound with two existing homes and a private permitted dock.
Both the main house and guest house boast unobstructed water view... Click here for more details
41 & 0 Cook Road Vineyard Haven
New Price: $1,690,000 | Original Price: $1,790,000 | Change: -5.6%
Property Description:
Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, s... Click here for more details
170 Barnes Road Oak Bluffs
New Price: $1,195,000 | Original Price: $1,095,000 | Change: + 9.1%
Property Description:
Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundr... Click here for more details
0 Old Country Lane Vineyard Haven
New Price: $450,000 | Original Price: $450,000
Property Description:
Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.
9 Marthas Way Edgartown
New Price: $4,600,000 | Original Price: $4,800,000 | Change: -4.2%
Property Description:
ONE MILE FROM HISTORIC EDGARTOWN VILLAGE; Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with fre... Click here for more details
53 Stoney Hill Road West Tisbury
New Price: $2,999,000 | Original Price: $3,299,000 | Change: -9.1%
Property Description:
Nestled in one of Martha’s Vineyard’s most coveted locations, this custom-built residence blends timeless elegance with contemporary luxury. Complete with exclusive access to the serene shores of Lambert’s Cove Beach.
At the heart of the home lies a professionally designed chef’s kitchen, f... Click here for more details
345 North Road Chilmark
New Price: $1,375,000 | Original Price: $1,550,000 | Change: -11.3%
Property Description:
This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two ... Click here for more details
100 Gosnolds Way Chilmark
New Price: $3,300,000 | Original Price: $3,400,000 | Change: -2.9%
Property Description:
Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands... Click here for more details