When making property decisions that impact you now and in the future, you will need a partner who knows Martha’s Vineyard Real Estate. The team members at Seacoast Properties are a dedicated team of passionate, property professionals who understand our clients’ needs and wants. We're here to serve you and make your Martha's Vineyard dreams a reality.

Explore homes for sale in Martha's Vineyard.

Explore our entire selection of premier Martha's Vineyard rentals to find the stay of your dreams.

Seacoast Exclusive

This 3 + acre Lower Makonikey lot with mature trees is a short distance away from a deeded private association beach. A quiet friendly community with protective covenants. The lot has been surveyed and a building envelope has been established. To date no testing or septic design has been performed.

Residential Property Image/jpeg #1

Residential Property Image/jpeg #2

Residential Property Image/jpeg #3

Residential Property Image/jpeg #4

Residential Property Image/jpeg #5

Residential Property Image/jpeg #6

Residential Property Image/jpeg #7

00 Kennebago Avenue - 65-E-1

Association Fee

Association Fee Includes

Basement

Fireplace Features

Flooring

Foundation Types

Frontage Type

Heating

Interior Features

Link MLS Comments

Lot Features

Parking Features

Possible Use

Assessed Building Value

Assessed Land Value

THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground utilities and town water in place and each lot has been approved for up to six bedrooms per Oak Bluffs Board of Health. A peaceful and private setting abutting conservation land and trails for hiking, walking and biking! Don't wait to be part of this lifestyle!

22 Paddock Road

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 a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system.

2 Other House Road

Exceptional 8 bedroom home with attached artist/fitness barn studios. 
Each bedroom includes a en-suite bathroom.
The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

Residential Property Image/jpeg #8

Residential Property Image/jpeg #9

Residential Property Image/jpeg #10

Residential Property Image/jpeg #11

Residential Property Image/jpeg #12

Residential Property Image/jpeg #13

Residential Property Image/jpeg #14

Residential Property Image/jpeg #15

Residential Property Image/jpeg #16

Residential Property Image/jpeg #17

26 Curtis Lane

Unique opportunity to purchase two adjoining lots at 211 Upper Main Street and 26 Curtis Lane in Downtown Edgartown. 

211 Upper Main St., Edgartown is a 15 bedrooms, 18 full baths, 2 half baths building with two large artist/fitness studios attached. It is in the B1 Commercial zoning district. Each bedroom includes an en-suite bathroom. Spacious kitchen and dining area. The kitchen/dining area includes: 2 refrigerators and 4 freezer drawers, A 5-burner gas stove and oven, 2 dishwashers, 1 microwave. Spacious living room: including 2 sofas and 1 coffee table, finished basement (2,000 square feet), Basement includes: 10 washer/dryers, 1 television and DVD player, 2 small rehearsal rooms, Complimentary Wi-Fi, Outdoor deck with picnic tables.

26 Curtis Lane is an exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

Two more adjacent lots with parking and a yard are also available for purchase upon request.

Residential Property Image/jpeg #18

Residential Property Image/jpeg #19

Residential Property Image/jpeg #20

Residential Property Image/jpeg #21

Residential Property Image/jpeg #22

Residential Property Image/jpeg #23

211 Upper Main Street & 26 Curtis Lane

PRIME 5-ACRE LOT - R20 ZONE EDGARTOWN 
Introducing a rare opportunity to own a piece of the island (currently two parcels) close to all Edgartown has to offer. This spectacular level lot is situated along Edgartown Road and provides the perfect setting to create a private retreat or a potential subdivision. The property borders the Triangle area of Edgartown, with ease of access to public transportation routes. Ideally located just minutes from beautiful beaches, boutique shops, and world-class dining. Please note, that perc tests and utilities are the buyer's responsibility. Don't let this extraordinary opportunity to build slip away!

15 & 27 Pennywise Path

You’ll always feel like you’re on vacation at this four-bedroom, two and one half bath home sited perfectly on 2.4 acres to capture sweeping vistas of the Atlantic Ocean and Noman's Island. Built in 2006, this home features an open living room, dining room and stainless steel kitchen flooded with light from the wall of windows providing wide views to the Atlantic. Enjoy dining on the wrap around mahogany decking. Views are also seen from the large, first floor, primary bedroom with en-suite bath. Descend to the lower level, where three additional bedrooms await—two of which have water views. The larger of the three bedrooms has walk out access to a patio with an adjoining flower and vegetable garden. A large bathroom, laundry and utility room complete the lower level. The property is further enhanced by stone walls and mature landscaping, creating a picturesque setting. A workshop/studio with full basement, plumbing, electricity and a wood stove is located at the rear of the property. A new Land Bank/Sheriff's Meadow property currently under development will provide access to Squibnocket Pond and one of the most beautiful beaches on the island and is located just across the street.

Residential Property Image/jpeg #24

Residential Property Image/jpeg #25

Residential Property Image/jpeg #26

4 Nomans Watch Road

PRIME 1.5 ACRE BUILDING LOT IN EDGARTOWN - Seize this opportunity to design and build your very own signature estate in Katama including the possibility of a Main House, Guest House, Garage, Pool, and more! This conforming, R-20 prime building parcel will support EIGHT BEDROOMS (8) with a standard Title 5 septic system. Nestled in an area of fine homes and ideally located on the edge of famed Katama, just 4 minutes to Main Street in Edgartown. PLEASE NOTE: Locus shown in first photo is approximate. Refer to attached documents for complete survey.

26 Mill Hill Road

Private Atlantic Ocean beach lot located on the serene coastline of Aquinnah on Martha's Vineyard.  This exceptional beach lot offers a rare opportunity to own a piece of prime oceanfront. Located just off of Moshup Trail is private gated access to your own designated parking area. From there, a picturesque boardwalk meanders through native flora and opens onto a sandy path leading directly to the water's edge. The sandy ocean beach offers panoramic views of the Atlantic Ocean. Don't miss your chance to own a piece of Martha's Vineyard's coveted coastline.

00 Moshup Trail

WELCOME to this turn-key CHAPPY COMPOUND!  This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the traditional US Open colors. The court is lined for tennis as well as two full pickleball courts with portable nets.  Game on!  All of this is set upon three acres of private, expansive land with distant WATER VIEWS! 

The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location!

This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping.

The Workout & Game Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. 

The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large.  

The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Workout & Game Barn.  The interplay between the Workout & Game Barn, Pool House, Pool and abutting Tennis and Pickleball Courts makes this Chappy Compound fun and playful! Strong Rental History.

Residential Property Image/jpeg #27

Residential Property Image/jpeg #28

Residential Property Image/jpeg #29

Residential Property Image/jpeg #30

Residential Property Image/jpeg #31

Residential Property Image/jpeg #32

Residential Property Image/jpeg #33

Residential Property Image/jpeg #34

Residential Property Image/jpeg #35

Residential Property Image/jpeg #36

Residential Property Image/jpeg #37

Residential Property Image/jpeg #38

Residential Property Image/jpeg #39

Residential Property Image/jpeg #40

Residential Property Image/jpeg #41

Residential Property Image/jpeg #42

Residential Property Image/jpeg #43

Residential Property Image/jpeg #44

Residential Property Image/jpeg #45

Residential Property Image/jpeg #46

Residential Property Image/jpeg #47

Residential Property Image/jpeg #48

Residential Property Image/jpeg #49

Residential Property Image/jpeg #50

Residential Property Image/jpeg #51

Residential Property Image/jpeg #52

Residential Property Image/jpeg #53

Residential Property Image/jpeg #54

Residential Property Image/jpeg #55

Residential Property Image/jpeg #56

Residential Property Image/jpeg #57

Residential Property Image/jpeg #58

Residential Property Image/jpeg #59

Residential Property Image/jpeg #60

Residential Property Image/jpeg #61

Residential Property Image/jpeg #62

Residential Property Image/jpeg #63

72 Chappaquiddick Avenue

Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on property is a detached 304sq. ft. garage/cottage.

9 Galway Road

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench, offering stunning water views of Vineyard Sound and the Elizabeth Islands. Ideally located just steps from Gray's Beach and dock, this is one of the most picturesque properties in Seven Gates Farm. The Seven Gates Farm community consists of 45 homesites on 1,600 acres with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails for walking and horseback riding. Residents of Seven Gates Farm also enjoy exclusive access to 1.5 miles of private beach, two piers, and two tennis courts. This rare opportunity allows you to become part of a remarkable community, once an assembly of farms, that remains dedicated to the preservation and stewardship of the land.

85 North Reservoir Road

Great opportunity for commercial space in a thriving business district with plenty of street parking and a storefront and side entrance. Office / Studio / Retail ~ Your choice! The space is versatile and is currently set up as a large open space with 2 dressing rooms, a large storage room in the back, and a shared half bath. If you are looking for a different layout, the space can easily be reconfigured to fit your specific business needs. With move-in-ready space and a fabulous location, this is an exciting opportunity to own a piece of commercial/retail space, whether for your own business or as an excellent rental investment property.

47 Circuit Avenue 1B

LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own family compound including all the popular requests such as a 3-car garage, pool and pool house. The oversized lots are connected to town water and town sewer and all have an established building/development envelope.  Substantial new construction homes are up on surrounding lots 1, 2, and 5. Lot 4, which is 1.57-acres, is currently being offered and is ready for your design concept.

63 Division Road

"Turn-key" offering!  This custom cape design with a delightful farmer's porch provides ample opportunities to entertain.  Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard and a pool!  The large detached two-bay garage has a new attached studio with full bath, laundry, kitchen and a private deck.  Newer exterior cedar shingles and trim, and a new 4 bedroom septic installed.  Equidistant to each down-Island village, it resides within a mature neighborhood with attractive curb appeal.

2 Farm Path

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming, sailing, and relaxing with friends or family are just a few of the daily dalliances of time spent on Chappy. There is simply no better place to relax and unwind.

9 North Neck Road

This commercially zoned property enjoys plenty of foot traffic in the heart of Circuit Avenue’s pedestrian activity. The space is bright and cheery with great natural light. Currently set up as a hair salon with access to a shared half bath, the space can be transformed to fit other specific needs including retail or office space. The property offers an opportunity for a piece of commercial/retail space or as an excellent rental investment property.

47 Circuit Avenue 1A

Rocco's Pizza Restaurant located in the vibrant Tisbury Marketplace. This is an Iconic Island Eatery open year-round! For Sale is this "Turnkey" business along with the 2 commercial retail condominiums totaling 1309 sf, which the business occupies. There is also a water view roof-top deck consisting of an additional 500(+-) sf. with plenty of seating. OWNER IS OPEN TO CREATIVE FINANCING WITH THE OPTION OF PURCHASING THE BUSINESS ONLY AND LEASING THE REAL ESTATE PORTION WITH AN OPTION TO PURCHASE THE REAL ESTATE IN THE FUTURE. This is a rare opportunity to own a successful and well-established island business. Sale includes all equipment, commercial appliances, furnishings, fixtures, and recipes. Owner currently holds a Beer and Wine Permit which is transferable to the buyer upon application and approval from the Town of Tisbury. Property has 3 half-baths, 2 sets of stairs to access the upper deck. There are water views from the first and second floors, along with an abundance of convenient parking. A very desirable location, along the Tisbury Waterfront area which is in the midst of a revitalization. NOW is the perfect time to make your investment. Inventory List and Financials are available upon request.

79 Beach Road B13 and B14

TURKEYLAND COVE: 3-ACRE ESTATE-SIZED PARCEL IN KATAMA.  This beautiful and private building site is one of the last remaining 3-acre parcels in Katama. The property offers a perfect opportunity to create a signature residence, multi-generational retreat, or equestrian dream, with possibilities for a Main House, Carriage House, pool, tennis court and/or barn. An idyllic Katama lifestyle awaits . . . with mornings spent walking or beachcombing along the windswept shores of South Beach or spent swimming and picnicking at Norton Point. For time on the water the property offers easy access to the Edgartown Great Pond from Wilson's Landing where you can enjoy kayaking, paddle boarding or taking a motorboat across the pond to enjoy the sand and surf at the Land Bank barrier beach. This expansive property offers the opportunity to enjoy all the best of Katama living with easy access to Edgartown Village shops, restaurants and more. IMPROVEMENTS: NHESP approvals already obtained and clearing has been done inside the approved building envelope. There is a new electric service off Slough Cove Road, a new well has been installed and 4-bedroom septic design has been approved by the Edgartown Board of Health.  Architectural plans available for separate purchase ($75,000) with a gorgeous modern farmhouse.

9 Turkeyland Cove Road

The Salt Shack merges historic preservation with modern updates in Menemsha. Designed by husband-and-wife luxury boutique design firm, Morgan Studio, the renovation of this 100-year-old ocean view cottage preserves its charm and historical integrity while incorporating contemporary design elements to enhance both comfort and aesthetics. Nestled behind Menemsha Pond, the cottage boasts a prime location for watching incredible sunsets over the pond to the ocean beyond and strolling into town for beach-going, fishing, boating, shopping, and dining. The layout and flow of the spaces feature captivating views from many vantages, and all new windows enhance natural light and views. The refined palette and materials reflect the natural surroundings and match the experience of Menemsha living. With modern forced air cooling and heating and a fully insulated structure, the property can be enjoyed year-round. Additionally, the ground level suite is the ideal complement to the two upper floors, providing a private retreat for family and friends. A turnkey ocean-view offering, the Salt Shack presents a rare opportunity to enjoy a stunning escape to the authentic fishing village of Menemsha.

10 Molly's Way

A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and a kitchen with doors leading out to a welcoming screened porch. This home features a primary bedroom suite  and a guest bedroom suite on the first level. Two additional guest bedrooms complete second floor. The exclusive Boldwater Association offers tennis courts, a boat landing on the Edgartown Great Pond, and a private South Shore sandy Atlantic Ocean beach. The Edgartown Great Pond is great for kayaking, paddling and boating.

4 Boldwater Road

Upon entering through the charming side door, you're welcomed into a beautifully screened sun porch – the perfect spot to relax and soak in the surroundings. This inviting space leads to a sprawling, light-filled chef’s kitchen, designed for both culinary creativity and social gatherings. Adjacent to the kitchen, a warm and welcoming living room awaits, featuring a convenient half bath and access to a cozy first-floor bedroom. Just to the right, you’ll discover a second ensuite bedroom, offering both comfort and privacy for guests or family.

From the hallway, a staircase leads to the upper level, where two additional, spacious bedrooms each come with their own well-appointed bathrooms, creating a serene and private retreat.

A second door off the living room opens to the lower level, where you’re greeted by a partially finished entertainment haven, complete with a pool table – an ideal space for relaxation and recreation. Further down the hall, to the left, is the media room, a cozy setting perfect for movie nights. Across from the media room, you’ll find a convenient half bath that leads into a laundry room with direct access to the backyard, blending functionality and convenience seamlessly.

32 Norton Orchard Road

This historic commercial property, built in 1790, is ideally situated in the vibrant heart of Downtown Edgartown. Currently functioning as a blend of retail and residential units, it presents remarkable opportunities for diverse ventures. The property combines exceptional Main Street frontage with a large open lot that abuts Edgartown’s primary downtown commons, the Village Green. Whether you aspire to establish your own business or take advantage of the rental market, this property offers an exceptional chance for both ownership and investment that should not be overlooked.

37 Main Street

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy access to all island amenities, including beaches, bike paths, state forests, and public transportation. Step inside to discover a bright and airy first floor, adorned with hardwood floors and a cozy fireplace. The spacious eat-in kitchen boasts stainless steel appliances and granite countertops, complemented by a slider leading to a sprawling deck overlooking manicured landscaping and gardens. On the first floor, you'll find a convenient bathroom and one bedroom, while the second floor hosts a generously sized primary bedroom with abundant natural light and a skylight. Two additional bedrooms and another full bathroom complete the second level, offering ample space for family and guests. Adding to the allure of this home is the expansive basement, spanning 890 sq. ft. and providing endless possibilities for storage, recreation, or future expansion. Don't miss out on the opportunity to make this exceptional Edgartown property your own.

60 Windsor Drive

Designed by renowned architect Araldo Cossutta as his personal retreat, the estate is made up of 5 dwellings providing a rare opportunity with pre existing density. One of the most stunning approaches from Middle Road thru your 8 acres of agriculturally conserved land. In need of renovation, the options are endless. Create a family compound, B+B/Inn, Farm, much needed housing or other ideas. Priced for sale "As Is". Showings to begin Saturday March 15th.

0, 27 & 30 Tower Lane

Enjoy waterfront living at its best with 163’ of Lagoon frontage, including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning water views and spectacular sunsets. This is your time to enjoy Vineyard life on the water ~ boating, swimming, kayaking, clamming, and more. Savor the views from almost every room of the house, designed to accommodate family and friends with ease, and comfortable living. It is rare to find a home in a setting like this on Martha’s Vineyard. Tucked away off Barnes Road in a remote locale and close to many Island favorites. The main level, with high ceilings and large windows, enjoys natural light and provides spectacular water views from all angles. A wood-burning fireplace and wet bar set the tone of the living room, and a more formal sitting area is focused on the views. There is a half bath, a dining room, and a large eat-in kitchen with access to the patio. Two additional rooms with a private deck and full bath are cleverly located in a separate wing of this floor and can be used as an office or den. Unique to the second floor is a wraparound deck and screened porch overlooking the Lagoon. The primary suite has a wood-burning fireplace, a walk-in closet, and a generous en suite bath with direct access to a private deck overlooking the Lagoon. There are two additional spacious en suite bedrooms on this floor which also enjoy fabulous views. If you are looking for a quiet retreat, a second covered porch at the front of the house is the place for you. Have fun transforming this 2,000-square-foot walk-out basement with a full bath to fit your needs.  Being sold furnished, this is the ultimate Vineyard Experience.

267 Barnes Road

Waterfront beach house on Dogfish Bar in Aquinnah.  Take in the beauty of this gem of a location with rolling dunes, waterviews and immense sunsets!  This property is one of only a few homes on this stretch of private and preserved beach.  This 2009 contemporary beach house offers a reverse floor plan with the entire top floor as the living area, kitchen & dining, and more windows than walls to enjoy the views!  Cherry floors, a fireplace and plenty of space for cooking, dining and entertaining.  The first floor offers an en suite bedroom, and two guest bedrooms with a shared bath.  Recently expanded deck off the living area.  A detached shed houses the water filtration system and offers storage for bikes, beach gear and fishing equipment.  Meander down the path through the dunes to the sandy beach for some of the best swimming, sunsets, fishing and boating on the island.  198' of pristine shoreline, sandy beach and dunes.  This is a magical spot on the Island!

29 Oxcart Road

Great location, this vacant 1.44-acre lot is located on a quiet street with direct access to the bike path and proximity to State Beach, and just minutes to town for shopping, dining, and enjoying all the activities and amenities of Edgartown Village. The wooded parcel will support 2 bedrooms with a NitRoe 2ks Enhanced Septic System. The lot has been staked, and perc tested, and the septic design has been approved by the Edgartown Board of Health. The property is in the NHESP zone and the NHESP study has been completed. The seller is in the process of installing the well. Don’t miss this exceptional opportunity.

117 Pennywise Path

Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either an Enhanced Septic System or Advanced Treatment System, or alternatively, a 2-bedroom home equipped with a Title 5 septic system. Prospective buyers are encouraged to confirm building options and requirements with the Town of Oak Bluffs. 
Attached documents for buyers review.

56 Holmes Hole Road

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 house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite. 
Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses.

25 Fulling Mill Road

Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.
The interior with it's custom wooden features and ships ladder to the deck gives it a nautical feel. It's surprisingly spacious with a living area, dining and separated kitchen. The primary bedroom is over 16' x 21'. Just off the hall is a tiled bathroom with glass enclosed shower and another bedroom. This space is perfect for year-round living or makes a great summer rental property with it's ideal location. No need for a vehicle with in-town living, beach, and access to all the Ferries within a few blocks.

37 Circuit Avenue 4

Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood floors, air-conditioning, custom built-in with a open yet divided living area, a sleep alcove and wood staircase to the rooftop deck. The large bedroom has a sunny nook with a opening skylight. This condo is ideal for a year-round living, an escape from the city getaway, or would make a great vacation rental with no car needed.

37 Circuit Avenue 5

Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space.  
The main level boasts a thoughtfully designed floor plan featuring a gourmet kitchen, a spacious living area, and a dining space ideal for entertaining. The primary bedroom suite offers a private retreat with a luxurious en-suite bathroom.

With a 6-bedroom septic in place, the possibilities for expansion are endless. The generous lot size allows for the potential of a garage, guest house, and pool catering to your individual vision. 

Located in the sought-after Vineyard Haven, this home presents a rare opportunity to embrace a lifestyle of luxury and tranquility. The property is located within the Lagoon Watershed and does not require a septic system upgrade. The current system complies with the new town regulations. 24-hour notice is needed for all showings.

46 Red Buoy Lane

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has in store for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2024 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.

34 Windemere Road

This attractive colonial style home is located in a terrific neighborhood. Just a short distance to the center of town with nearly 1/2 acre of rolling treed land.  The features include a cathedral ceiling over the kitchen and dining room. A large fireplace highlights the living room. From upstairs you can look over the balcony to the dining area and kitchen below. The first floor bedroom with has its own bathroom. A small screened in porch on the front side of the house will keep the bugs away. A spacious deck is on the back side of the house. Built in 1972, this home  needs some TLC but is well worth it in this terrific neighborhood. Price includes a $50,000 credit to the buyer to bring the septic system into Title V compliance with the Tisbury Board of Heath.

96 Dunham Avenue

New to market this completely renovated water view home is located in a private  enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic  Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet kitchen, adjacent butler's pantry & vast open living area with wood burning fireplace, mellow wood floors and breathtaking views out every window. Four large bedrooms, three bathrooms plus a powder room. Primary suite bathroom features an independent tub and steam shower.  Fully heated, insulated and air conditioned this home is  four season living. Walking paths to pond access for kayaking, swimming and boating & association tennis court. This property is protected by a Trustees of Reservation Deed of Conservation Easement.

16 Shotnaigher Lane

This distinguished Edgartown Great Pond compound presents an exceptional collection of features and amenities. Situated within a highly desirable, secluded enclave on Turkeyland Cove, the 4.8-acre property includes two residences, a bespoke private in-ground swimming pool, approximately 400 feet of waterfront, outstanding water views, and a private beach lot on the Atlantic Ocean. The principal dwelling offers four bedrooms, exquisite craftsmanship throughout, and a unique setting right along the water. The secondary residence was constructed in 2010 and spans 2,556 square feet, featuring two bedrooms, a three-car attached garage, and a full basement. The buildings are harmoniously integrated with meticulously designed plantings, landscape, and custom-built fencing and gates. The pool area provides a secluded oasis, with an L-shaped gunite swimming pool nicely complemented by two adjacent outbuildings. Expansive lawns gently slope towards the waterfront, and boat access to the Atlantic beach is readily available from the property shoreline. Held by the same owner for over three decades, this property represents an unparalleled opportunity.

74 Turkeyland Cove Road

East Chop waterfront – Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 3.) Or convert to condominiums, paperwork has been completed but would be a buyers choice.

Located directly on the harbor, this property features outstanding water views of the harbor and sound beyond and is just steps from the tennis club, beaches, ferries to the mainland and downtown. In pristine condition, this 7-bedroom  property includes a 106 ft dock with water/electric for 8 slips and a 40’ T at the end for a 9th boat. Parking for 6-7 vehicles at street in front. Built in 1952, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, all new heating/AC mini-splits, new exterior security cameras and dredged dockage. Features include high end finishing in all units, as well as beautifully landscaped grounds. The first floor consists of three 1-bedroom units, each with new kitchen, living and dining areas and private covered front porches over-looking the water. The second floor consists of two 2-bedroom units each with kitchen, living and dining areas as well as private covered front porches. A separate detached year-round cottage apt unit with Murphy bed, kitchen, full bathroom and washer/dryer can serve as a rental unit or as live in office for a property manager/caretaker and, has an additional loft area with double bed for kids. Each apartment has electric baseboard heat plus mini-split heat/AC. Generator. Furniture included depending on price. Private outdoor shower with dressing area. On town sewer.

47 East Chop Drive

East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each condo unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, and dredged dockage. Features include crown molding and attention to detail, new kitchen and bathroom (with handicap accessible shower) with Italian Carrara subway tile, classic and timeless, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. House keeping available at owners discretion.  Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

47 East Chop Drive Unit 5

East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the "Tivoli", features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include crown molding and attention to detail, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. Hot water on 80-gal. tank, metered and proated.  House keeping available at owners discretion. Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

47 East Chop Drive Unit 4

East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, "Cottage City", features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with fireplace, dining area and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each condo unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include crown molding and attention to detail, new kitchen and bathroom with Italian Carrara subway tile, classic and timeless, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. New hot water tank 2023. House keeping available at owners discretion. If owner desires, the propane fireplace may require a new propane tank exclusively for the fireplace independent of generator, inspection and approval of town and fire department, prior to operation. CO detector required. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

47 East Chop Drive Unit 2

This classic East Chop Drive gem lies on a 10,000 sq. ft. lot nestled in the sand dunes, just steps to the waters edge and private dock. The 4-bedroom/2.5-bath cottage went through a substantial renovation years ago with the majority of mechanicals, electrical and plumbing being updated. There is an open floor plan with kitchen, dining and living space with cathedral ceiling and wood burning fireplace. There is a ground floor master with private bath and lots of glass, a second bedroom with half bath and laundry/mudroom. The second-floor features 2-bedrooms and a shared bath. The cottage style structure is super charming inside and out and has a wonderful water facing brick terrace with built-in planter, a covered porch and a one-car garage. Beautiful landscaping with lawns and gardens complete this very special property. Let's not forget to mention, it offers some of the best seats on the Island to take in the incredible sunsets.

311 East Chop Drive

Flat building lot centrally located in West Tisbury.  It is the Buyer's responsibility to conduct a perc test and install utilities, well and septic.

22 Bramble Path

East Chop Water Front Luxury Condominiums -- This 2-bedroom, waterfront condominium, the "Highlands", features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a private covered front porch over-looking the water. The unit has electric baseboard heat plus mini-split heat/AC. Common areas include a private outdoor shower with dressing area, and outdoor patio/grill area. Condominium owners have first option to rent a slip at the 106 ft dock for 8 slips and a 40’ T at the end for a 9th boat. Each unit includes a designated parking space for one vehicle. Built in 1952, and operated as East Chop Harborfront Apartments since then, the property has had extensive top to bottom renovations including new wiring, plumbing, insulation, heating/AC, exterior security cameras and dredged dockage. Features include high end finishing, as well as beautifully landscaped grounds. Laundry service available. Occupancy available beginning Nov. 1st, 2025. New condominium pending buyer approval of final condominium documents. House keeping available at owners discretion. Hot water on 80-gal. tank, metered and prorated. Sold with furniture depending on price. Available for showing with 24-hour notice until June 15th, thereafter Saturday's 10-12.

47 East Chop Drive Unit 3

**Charming Vineyard Waterfront Cottage in Oak Bluffs**

Nestled in a peaceful cul-de-sac in Oak Bluffs, this newly renovated 2-bedroom, 1-bathroom cottage offers the perfect blend of traditional Vineyard charm and modern sensibility. With stunning panoramic views of Brush Pond, the Lagoon, and the iconic Drawbridge, this cozy retreat provides the ultimate setting for both relaxation and outdoor enjoyment.

Inside, natural light pours into the open-concept living, dining, and kitchen areas, creating a bright and airy space designed with comfort in mind. The spacious kitchen flows seamlessly into the dining area, where you can enjoy meals with a view or sip a morning coffee while taking in the serene landscape. The living room offers a cozy space to unwind, while large windows frame the breathtaking vistas and invite the outdoors in.

Step outside onto the surrounding patio, where you'll find plenty of seating to enjoy the tranquil surroundings. Adirondack chairs and patio furniture provide the perfect spots to watch the sunset over the water—an experience you won't want to miss. Lush greenery, vibrant flowers, and mature trees create an idyllic outdoor oasis.

Whether you’re seeking a peaceful retreat or a place to entertain, this Vineyard cottage offers it all. The combination of its charming interior, spectacular views, and serene outdoor spaces make it a true haven. Ideal for a vacation home or year-round residence, this property is a rare find in Oak Bluffs. Don't miss the chance to call this waterfront beauty your own! This property is a great income producer, with a very strong rental history.

66 Brush Pond Road

This one of a kind property is extremely private, yet only 12 minutes to the airport or Edgartown Village. The 10+ acre parcel is bordered on two sides by Sheriff's Meadow Conservation land and miles of walking trails nearby. The dwellings and other structures are meticulously crafted and offer a range of possibilities. The "guest house" is 2300 sq ft with finished basement and loft space.  The "barn" encompasses an 1,832 sq ft two bedroom, three and one-half bath apartment with fireplace, a 1,730 sq ft loft space with full bath, a multiple car garage with Tesla charger, and equipment room with counter and sink.  The garage, loft and equipment room have red pine wall paneling. There is an exceptional 800 sq ft greenhouse and many other amenities are too numerous to list.  This unique property is part of the Boldwater Association a sought after private enclave with use of the association tennis courts and deeded pond and Atlantic Ocean beach access across Edgartown Great Pond.  The "barn" was built in such a way that it could be converted to an expansive single family home with a pool. This is a very special property with loads of potential. Call for a private showing of this one of a kind opportunity! FYI: First photo shows deeded pond access close-by to access the barrier beach on the south shore.

4 Jacobs Neck Road

Exquisite Waterfront Retreat - A rare opportunity to purchase a meticulously crafted 5,600 square-foot stone main house and 900 square-foot stone guesthouse with pool in a naturalized wooded setting.  This extraordinary compound redefines the conventions of traditional Vineyard architecture in the most charming and sophisticated of ways. The house was sited to offer views of Edgartown Great Pond and distant ocean views from almost every room and possesses a delightful mix of contemporary and modern features, such as geothermal and solar panels. The houses sit on nine acres of beautiful waterfront with 800 feet of sandy pond beach frontage. A 16’ Duxbury Dory with trailer in excellent condition included with the house, allowing you to explore the great pond and easily access Atlantic Ocean beach rights only 15 minutes away.  In a private though convenient location only 12 minutes to the airport or Edgartown Village. This property may be purchased with 4 Jacobs Neck, if you need more space close-by for family and friends! Please call listing broker for details.

Residential Property Image/jpeg #64

Residential Property Image/jpeg #65

Residential Property Image/jpeg #66

Residential Property Image/jpeg #67

Residential Property Image/jpeg #68

Residential Property Image/jpeg #69

Residential Property Image/jpeg #70

Residential Property Image/jpeg #71

Residential Property Image/jpeg #72

Residential Property Image/jpeg #73

Residential Property Image/jpeg #74

Residential Property Image/jpeg #75

33 Boldwater Road

You haven't missed the boat. And if you live here, you will never miss the boat.
This fully furnished, classic Vineyard-style home can be your home in time for spring.  
This beautifully restored 3-bedroom, 2-bath home has touches from the old Vineyard—a sun porch for napping or reading, a large yard with magnificant magnolia tree, and a detached garage for your Island car. You will never have to worry about steamship reservations again.
You're within walking distance of everything you need—markets with locally grown food, fish, and meats; coffee shops, restaurants, galleries, 
and you can walk to the Steamship Authority terminal.  
This Vineyard classic home is being sold fully furnished down to the lobster pot. All you need to bring is your swimsuit.

249 State Road

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 easy to understand why this property is so special. There's a generous designated building envelope of 1.41 acres to allow a Buyer to build a significant house with multi level views of the water and additional structures with proper permitting. Thoughtful planning and preparation of the Tower Hill Declaration for the area creates a deeded view easement and greenbelt area to preserve the serenity, privacy and experience of being surrounded by nature while still being minutes away from West Tisbury center. The abutting lots have already been developed, demonstrating the type of home, landscape, and view possible for 38 Fire Tower Road. Outlands Design has created architectural rendering, shown via the CGI imagery photos to help envision a home, infinity pool, driveway and landscaping. The property is staked, and surveyed with paths cleared to make showing easy. NHESP requirements met. Perc test done and the well (12 gpm) has been installed.

38 Fire Tower Road

Embrace the Essence of Martha's Vineyard on Red Buoy Lane. This idyllic vacant lot in Vineyard Haven offers a gateway to serene island living. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy the peace of a rural setting, yet remain conveniently close to the ferry and vibrant downtown Vineyard Haven. Design your home with a walk-out basement, maximizing natural light and living space. Benefit from the Massachusetts ADU law and build an accessory apartment or guest house with no waiting period. The Board of Health confirms there is no limit on the number of bedrooms with the required enhanced septic system - you just need to comply with zoning setbacks. Seize this extraordinary chance to make a shrewd investment and build your legacy on Martha's Vineyard. Note: This is the last vacant lot available in the now established subdivision. Disclosure: Listing Broker is property owner.

0 Red Buoy Lot 147

This recently constructed home conveniently sits in the center of Edgartown close to Sengekontacket Pond.  With 3 bedrooms, 3.5 baths, bright and sunny living areas, and a very spacious and finished lower level, this property is well-designed.  Featuring hardwood floors throughout, the open concept on the first floor has modern kitchen with a center island and stainless appliances, a dining area and comfortable living room.  There are two spacious bedroom on the second floor, both with ensuite baths.  The finished basement has high ceilings, lots of natural light, a full bath, storage space, and a private entrance - a terrific rentable option! The solar panels will be sure to provide low electric bills.  The yard has new plantings with irrigation, a MicroFast septic system, and a gravel driveway.  This long lot includes additional, undeveloped space to increase the size of the yard, or seek approval to add a rear driveway from 14th Street, a pool or garage.

23 Thirteenth Street North

The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living area with light while providing a view to the side yard and fountain down below. Enjoy evenings on the deck or in front of the wood-burning fireplace. Any chef will be happy in the well-appointed kitchen with Thermador appliances that include a 5-burner cook top and double wall ovens, sizable island with seating, and counters topped with quartz. The kitchen affords views to the dining and living areas as well as out to the deck and yard. There is a first-floor room with an en suite bath. Pocket doors allow for the bath to be a powder room while providing privacy to the flex-room. Ascend the modern staircase to be wowed by the primary suite. The spa-like bath has double sinks and a make-up vanity. There is a glass-enclosed, tiled shower with multiple shower heads. The walk-in closet has been finished with hanging rods, shelves, and drawers. and there is a sliding door that opens to a balcony overlooking the yard. The second en suite bedroom has plantation shutters and a bathroom with a tub. Behind a pocket door, in the hall, you will find a well-organized laundry room with commercial-sized washer and dryer. White oak floors throughout the first and second level with tiled baths. Rinnai on demand water heater. Plantations shutters and custom shades throughout. There is an over-sized garage that is larger than many of the other units. With association amenities that include a pool with pool house, multiple tennis courts, playground, basketball court, private access area to Lake Tashmoo, and a beach on Vineyard Sound. If you are looking for luxury with the convenience of townhouse living, look no further than this truly spectacular unit.

150 Cove Road 10

This newly built traditionally styled Greek Reival home offers a wonderful open floor plan with refreshing interior design, all presented in excellent condition. The first floor front foyer, leads to the well-appointed kitchen with high-end appliances and large island. A dining area and living room with fireplace, all with an abundance of natural light. There are French doors leading to a covered porch with stone fireplace, all of which overlooks the exquisitely landscaped rear yard and patios. The second floor offers a spacious primary suite with sundeck and two additional ensuite bedrooms. The finished lower level offers two additional bedrooms with shared bath, a comfortable sitting room with TV and large laundry area. There is a detached barn to the rear of the property with a spacious deck that could be used for a number of usages, an outdoor shower and parking for 4-cars. All of the these mentioned on a quiet street just blocks to the downtown Historic District.

10 Tilton Way

This 4-bedroom / 3-bath home lies in the middle of East Chop at the highest point on the bluff offering expansive views of Vineyard Sound. The home features a large clear story living room with fireplace, a family room/kitchen also with fireplace, a huge screened porch opening up to a large deck area and a first floor bedroom with private bath. The 2nd floor offers two guest bedrooms and a master bedroom with large deck that share two baths. There are entrances on two roads, the grounds are nicely landscaped and there is a garage that could be used for a number of usages.

Seacoast Exclusive Martha's Vineyard Real Estate

No properties found

Explore Other Martha's Vineyard Towns