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Find charming homes for sale in downtown Martha’s Vineyard. Enjoy the vibrant island lifestyle with these centrally located properties.

Downtown

Downtown Homes for Sale, Martha’s Vineyard | MV Seacoast

A must see property located in the heart of Vineyard Haven. This three-bedroom, two bath, colonial style condo boasts expansive living spread over three floors. Completed in 2019, this energy efficient 1682 sq ft home includes a 5 KW solar PV system. The open layout of the first floor includes a modern, galley style kitchen with stainless steel appliances and extensive counter space. The three bedrooms located on the second floor include the primary bedroom with an amazing third floor loft. The loft spans the length of the home and offers distant water views of Lagoon Pond and Vineyard Haven Harbor at opposite ends. The house is surrounded by unbelievable, professionally landscaped yards with ornamental trees, a grape arbor, herb garden, planting beds, cobblestone walls, front and back lawns, and over 1500 sq ft of brick paver walkways and patio spaces. The property is fully fenced and provides the owners with a private oasis in the heart of downtown Vineyard Haven. This is village living at its best! In the back of the home there are two outbuildings. A large 16'x14' insulated/heated workshop with an attached 10'x12' storage room, and a detached 6'x8' garden shed. There is a three-car asphalt driveway at the front of the property and room for additional parking in the courtyard space at the front of the house. The property is a 4 minute (0.2 mi) walk to the Steamship Authority ferry terminal. Just steps from all the shops and restaurants downtown Vineyard Haven has to offer, as well as the MV Museam , and Veterans Park. Located in the Tisbury Waterfront/Commercial District with flexible zoning that allows for residential, commercial, or mixed uses. Additionally, the home is tied into the Tisbury Wastewater system which provides for possible expansion pending town and condo trust approval.

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62 Lagoon Pond Road B

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This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design, fosters positive and sustained interaction and relationships among people and the natural environment. The entrance to the home leads across enormous granite steppingstones bridging over expansive reflection ponds with two waterfalls cascading to a lower-level pond. The entry way welcomes one to open and dramatic living spaces with 10 ft ceilings and large expanses of glass facing Vineyard Sound and the surrounding landscape. In the main residence, each of the five-bedroom suites have unique features and connect with the beauty of the outdoors. The lower level of the residence offers amazing, eye-catching living spaces which include state of the art wine cellar, entertainment room, media room, gym and sauna. There is a spectacular glass circular staircase leading to a roof top pool which is surrounded by expansive decks and gardens and offers what is arguably the best place one could choose to watch the sunset each evening. The residence offers countless distinctive features and green technologies including self-sustaining solar energy. Minawetu is essentially a platform for a botanical garden, one with nature and a harmonic part of the island’s environment. Complimenting the property is a detached accessory building with two rooms and two full baths which is designed in harmony with the main house and constructed with the same level of detail. This outbuilding would also be a perfect place for a removed office or studio space. While it’s a short walk to the main residence, it enjoys privacy and it’s owns views over wild flower covered meadows. The landscaping is an incredible blend of open, natural settings complimented by the botanical gardens which grow on and around the house. There is a weathered stone staircase providing easy access to a white sandy beach. There are so many spectacular properties on the island of Martha’s Vineyard, each offering their own incredible features but there truly is no other property that captures the magic of Minawetu.

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60 Bartimus Luce Road

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.

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34 Windemere Road

East Chop close to beach and town! This 4 bedroom home has it all; great location, wrap around porch, plenty of parking, oversized garage, large shed, walk-out basement, heating system, original hardwood floors. 4 Bedroom Title V passed septic system. Don't miss this opportunity to buy in this desirable neighborhood just a short distance to the beaches, shops, and restaurants of Downtown Oak Bluffs.

11 John Wesley Avenue

This custom Gambrel-style home sits high atop Manaca Hill on Chappaquiddick Island with views of Edgartown Harbor and Katama Bay. The first-floor features hardwood floors throughout, tall ceilings and lots of windows to maximize the views. Enjoy the spacious open kitchen with top of the line appliances, a large center island and soapstone countertops. Perfect for entertaining, the area opens up to a sunny living room with fireplace and French doors leading out to the terrace. A formal dining room, laundry room, powder room and den with custom woodwork complete the first floor. All three-bedroom suites are on the second floor with luxurious private baths. The large, screened porch with fireplace and lounge seating is the perfect spot for morning coffee or a glass of wine before dinner. You will have the pleasure of spending your day on the private association beach just a short walk from the house, and the Chappy Ferry is also nearby for a quick run into Edgartown Village.

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5 Armstrong Lane

Live the beautiful Island Life with this gorgeous condo at an affordable price. This is a delightful one and a half bedroom seasonal condo ( sleeps 6) available for your families use. When you’re not here, the management team will rent and take care of everything for you. Amenities are amazing. There’s a beautiful pool, spacious outdoor area with lots of seating, fire pits, play area &  barbecues.  Right next to the popular Nomads restaurant and walking distance to two ocean beaches, bike paths and buses to towns.
Brokers must accompany clients.

21 Island Inn Road 35G

Final lot remaining in this subdivision. Includes an approved 4 bedroom septic permit. Town water available to each lot, and electricity. There is a $250 annual membership in the Holly Bear Lane Road Association required. Broker has a partial ownership interest in property. Broker is also a builder and can give a land/house package price. Homes in this area recently selling for near $3 million.

1 Holly Bear Lane

Explore this colonial style home in the ideal Edgartown Estates neighborhood. The upside-down layout maximizes lush tree views and privacy. The main living area awaits—a bright cathedral-ceilinged room that seamlessly blends kitchen, dining, and lounging spaces. Two separate decks with sliding doors off dining and living area perfect for summer gatherings with a fireplace to anchor the open layout. The first floor has French doors into the den—a versatile space for work or guest overflow. Three bedrooms including the primary bedroom with private porch and private bath. The property has a one car garage with two built-in storage sheds. The location of this home is ideal, nestled conveniently off the bike path and close to both town and South Beach.

30 Deacon Vincent Way

Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation.

Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with soaring ceilings. A staircase leads to a second-level landing area and a third level that extends across the entire structure. This additional space effectively doubles the square footage, totaling approximately 6,000 square feet. The barn offers endless possibilities, from completely renovating it into a massive 6-bedroom home to hosting large events or accommodating extensive storage needs. It must be seen to be fully appreciated.

There is a driveway to the property directly off Moshup Trail and an expansive backyard meadow perfect for a larger new house, a pool, or a large play area. Additionally, the property includes a charming 2-bedroom, 1.5-bathroom cottage with beautiful hardwood floors, providing an immediate, cozy living space.

With the existing 6-bedroom septic system in place, you have the flexibility to completely renovate, rebuild, or expand to meet your specific needs. The potential this property holds is limited by your imagination only. Don't miss the opportunity to make this unique property in Aquinnah your own, and create a custom retreat that perfectly suits your lifestyle.

9 Moshup Trail

This beautiful wooded 4.12 acre parcel of land is peaceful and serene, and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. The large, flat building envelope on this parcel offers many siting possibilities, the ability to create a meadow and open gardens or keep a more wooded feel, and the land is grandfathered for a possible guest house. The sought after Plum Bush Point neighborhood is located between two large conservation preserves, the 91-acre Short Cove Preserve and the 173 acre-Sepiessa Point Reservation. Launch your kayak or small boat from the Sepiessa Point Reservation just around the corner. This is a wonderful piece of land in a special location…private and close to nature yet convenient to West Tisbury town center and centrally located on the island, essentially equidistant from here to Menemsha Harbor, Edgartown Main Street and Tisbury Main Street. This property provides natural beauty and easy access to all the Vineyard has to offer, including access to Lambert's Cove Beach. Spend your day hiking miles of walking trails or exploring the waters and beaches of the South Shore, Tiah’s Cove and Tisbury Great Pond, and then come home to your private and quiet country retreat.

25 Plum Bush Point Road

Katama location! Approximately 1.5 miles to South Beach as well as the center of town. Very close to a bike path for easy access to all that Edgartown has to offer. This level lot already has a lawn with mature trees on it. Should be able to build a four bedroom house. Buyer should confirm this with the Board of Health.

9 Marthas Way

This waterfront Edgartown Great Pond compound abounds with rare features. Set in a coveted, private location on Turkeyland Cove, the 4.8 acre parcel includes two full sized homes, custom pool with pool house, +/- 400 feet of waterfront, outstanding views, and a private beach lot on the Atlantic. The main residence sits right on the shoreline, with four bedrooms and beautiful quality throughout. The second home, built in 2010, is set back from the waterfront - still with water views - with 2556 sf, two bedrooms, three car attached garage, and full basement. The property is tied together gracefully with extensive plantings, landscaping and custom fence/gateways. The pool area is an oasis unto itself, with two outbuildings supporting the L shaped gunite swimming pool. Open lawns lead easily to the waterfront, where you have access by boat to the Atlantic beach or other recreation on these pristine waters. Held by the same owner for over 30 years, this property is an opportunity not to be missed.

74 Turkeyland Cove Road

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. Super sunny lot that is fully engineered and ready to go. Single-family dwelling plus an 800sq ft guest house allowed by special permit, plus a detached bedroom and accessory dwellings according to the Chilmark by-laws. Great location in Chilmark, close to the Nashaquitsa town boat landing, Chilmark Town Center, and Menemsha. A dream location for Chilmark lovers. The lot offers interesting topography allowing for a lower-level walk-out basement facing south for maximum sunlight and additional living square footage.  A rare opportunity in Chilmark to own land in Chilmark in this association. Build/design package for a new owner will allow for ease in the development process.

4 Cedar Lane

This rare, unparalleled building opportunity sits on Squibnocket Farm, one of the island’s most private and spectacular locations. Squibnocket Farm consists of approximately 500 acres of forever-protected conservation land, with private access to over 2 miles of beautiful dunes and sandy beach. The 5-acre building site overlooks stone walled conservation fields and beyond to the island’s South Shore. The building envelope has been thoughtfully planned to maximize privacy, views, and to enjoy the pristine natural beauty that Squibnocket Farm affords.

2 Round Pond Road

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. Second floor waterviews over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling , plus a detached bedroom and accessory buildings allowed according to the Chilmark by-laws. Great location in Chilmark, close to the Nashaquitsa town boat landing, Chilmark Town Center, and Menemsha. A dream location for Chilmark lovers. The lot offers interesting topography allowing for a lower-level walk-out basement facing south for maximum sunlight and additional living square footage. A rare opportunity in Chilmark to own land in Chilmark in this association. Build/design package for a new owner will allow for ease in the development process.

32 Stonewall Road

Stonewall is a beloved area of Chilmark with private south shore beach access, well maintained roads and a supreme location for easy Chilmark living. Well located close to the Community Center, Chilmark Store, Quitsa Pond, Lucy Vincent Beach and Squibocket Beach. This property is being offered with two separate abutting lots totaling over 6 acres. 32 Stonewall has second-floor water views facing westward towards sunsets and Squibnocket Point. This parcel will allow for a single-family dwelling and accessory buildings (barn, garage, detached bedroom). The second lot (4 Cedar Lane) has the potential for a house and guest house, garage, barn, and detached bedroom. Both lots have a gentle southern slope allowing for a walk-out lower level where a buyer can gain additional square footage for living space. The potential square footage by right for the two main homes and a guest house is 7925 square feet of living space. This combination of acreage allows for a compound with  parking at Stonewall Association’s quiet and pristine Atlantic Ocean Beach. Both parcels are offered fully engineered with wells installed and septic designs forthcoming. This is a tremendous opportunity to acquire land in Chilmark where you can create exactly what you want while enjoying the privacy and amenities that Stonewall offers. A design-build package is available to a Buyer.

32 Stonewall Road and 4 Cedar Lane

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

Newly renovated commercial and residential building in Edgartown. Located on N. Summer St., less than a block off Main Street, this handsome building is finishing a complete renovation. The building includes 2 commercial spaces and 2 apartments each with their separate entrances, parking spaces in the rear, and storage spaces in the basement. No detail has been missed from the new appliances, tiles, and HVAC to the copper lanterns outside and the redesigned first floor deck. This is truly a unique property with endless possibilities. There are some leases in place, those can be available upon request.

31 North Summer Street

Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury.  Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen with top-of-the-line appliances and custom butcher block island.  Attached to the kitchen is a welcoming dining room and wet-bar and a screened porch with garden views.  The multiple spacious living areas are flooded with natural light and fireplaces perfect for both entertaining and everyday living.  The second floor features 3 beautifully appointed bedrooms with 3 updated tile baths. Additionally, a serene sitting room awaits, complete with built-in bookshelves, creating the perfect place for relaxation or study. Venture to the third level and discover a hidden retreat—a charming bedroom offering privacy distant water views. Outside, there is an expansive yard, a rare find in-town, offering ample space for outdoor gatherings and gardening. The detached 2-story 1-bedroom barn-style guest house beckons, a charming retreat with its own private back deck. From the elegant facade to the landscaped grounds with beautiful perennial gardens, every aspect of this property reflects a rich history and a timeless appeal. The perfect in-town location with easy access to Downtown Vineyard Haven restaurants, shops, beaches and ferry. Excellent rental history.

49 William 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

Welcome to your dream home in the exclusive Lower Makonikey Association, a serene enclave on Martha's Vineyard. This meticulously crafted 3,284 square-foot residence with a 3-car garage is a masterpiece of design and comfort, set on 3.21 acres of lush, tree-lined grounds accented by historic stone walls. Offering 4 spacious bedrooms and 4 elegantly appointed bathrooms, this home embraces the charm of island living.  The main level features a flowing floor plan, ideal for both entertaining and everyday living, with a gourmet kitchen with a sun-filled breakfast nook, and butler’s pantry, dining room, and a spacious living room with a brick fireplace.  A home office and laundry room finish the first floor which has beautiful hardwood floors throughout. Upstairs, the primary bedroom suite is beautifully appointed and features a spacious bathroom with double sinks, spa tub and shower.  The bedrooms are generously sized, with ample natural light and stunning views of the surrounding landscape. The third level holds tremendous potential, offering the possibility to add 2 additional bedrooms, further enhancing the home's versatility. Outside, the back deck and expansive grounds provide a peaceful sanctuary, perfect for outdoor activities, gardening, or simply relaxing in nature's embrace. As a resident of the Lower Makonikey Association, you'll enjoy access to a private association beach on Vineyard Sound. This exceptional property is more than just a home; it's a lifestyle. Experience the perfect blend of privacy, elegance, and community in one of Martha's Vineyard's most sought-after neighborhoods.

37 Memphremagog Avenue

Welcome to your dream retreat in Oak Bluffs. A magnificent eight-bedroom oceanview estate that combines luxury, space, and unparalleled views in one breathtaking offering. This property is designed to accommodate family and friends with ease while offering an elegant and serene environment for all to enjoy. The open floor plan of the main living areas ensures a seamless flow between the living room, dining room, and kitchen, making it perfect for entertaining. High ceilings and large windows flood the space with natural light and provide spectacular water views from every angle. The state-of-the-art kitchen is a chef's delight, featuring high-end appliances, ample counter space, and a large island that doubles as a breakfast bar. Custom cabinetry and elegant finishes complete this culinary haven. Each of the eight bedrooms is designed as a private sanctuary, offering comfort and tranquility. Most rooms feature ensuite baths and large windows that offer stunning water views, allowing you to wake up to the sight and sound of the gentle waves. In addition to the main living room, the property includes several cozy sitting areas, a media room for movie nights, and a game room, ensuring there's always a perfect spot for relaxation and entertainment. It's more than just a home, it's a sanctuary where you can create lasting memories with loved ones, enjoy sophisticated coastal living, and savor the unique charm of this beautiful area.

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150 East Chop Drive

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

CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to ½ mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard. An exceptional opportunity to create more than just a home, but cherished memories for generations to come.

0 Pocha Road Extension

NEW CONSTRUCTION, EDGARTOWN COMPOUND, ready for 2025.  This property offers a PRIMARY HOME, with four levels of living amongst 5,914 sq. ft. of high end finished space. The PRIMARY HOME has four bedrooms, each bedroom with a private full bathroom, there is a half bath, a mud room, an open floor plan with a gourmet kitchen, dining and living room. The 2nd floor offers three bedroom en-suites. The top level offers 994 sq. ft. of finished space with endless uses, i.e. a lounge, a game room or home office.  The lowest level, (basement area), offers 1,319 sq. ft. of finished space.  An attached two car garage opens into a well thought out mudroom area with half bath. The four levels of living offers privacy for company or multi-generational living. This is a well thought out designed home. The GUEST HOUSE offers privacy for family/guests with its one bedroom, full bath, kitchen/dining/lounge area.  The GUEST HOUSE offers additional storage in the unfinished basement.  Both the PRIMARY HOME and the GUEST HOUSE enjoy views of the POOL HOUSE, POOL and outdoor hardscape. The Gunite POOL is 16 x 34 ft. heated, saltwater and has a 7 x 7 ft spa with waterfall feature attached to it! The prime location of this property is an incredible additive to this offering.  It is close to the heart of Edgartown Village, the shops, dining, the library, and all Edgartown has to offer. This property is a hidden gem on the outskirts of Edgartown Village.

23 Pinehurst Road

Island Inn is the quintessential “condotel,” for buyers who want their vacations and easy income too!  The very popular resort offers grassy grounds, tennis, pool, charcoal grills, fire pits, playground and event hall – as well as oh-so easy access to State Beach and in-town Oak Bluffs.  There’s no need to worry about caretaking from afar.  Vacasa, the on-site management company, takes care of bookings, cleanings and routine maintenance to ensure the best guest - or owner-experience.   The compound is open six-plus months of the year, from April till October.  Unit 12, a fully equipped studio unit with easy ground level access, is located deep at the more peaceful end of the compound.  The unit is offered fully furnished - or you may upgrade it to your own taste.  Kick back on your patio with a beverage at the end of a long day of play.  Or run the toddler about the lawn till bedtime.  For a livelier evening:  Hang out at family-friendly Noman’s, just across the lawn.  See Documents for owner guidelines and Vacasa information.   Note: Showings inside the unit are scheduled only between tenants. Link to Vacasa: https://www.vacasa.com/usa/The-Island-Inn-MA/

27 Island Inn Road Unit 12D

New Construction To Be Built at Lagoon Ridge ~ The Homes at Lagoon Ridge is a subdivision of stylish, new construction properties to be built by M. Duffany Builders. The Naushon home design is an elegant 2 bedroom, 3 full and 1 half bath home with over 2500 square feet of fine craftsmanship. The curb appeal will immediately charm you with its welcoming wrap-around porch. Just off the foyer, the spacious Great Room is open to the kitchen and dining area, offering an ideal space to entertain large groups of friends and family. The smart kitchen design includes stainless steel Bosch appliances, spacious 42” tall wall cabinets, quartz countertops, and Kohler fixtures. The main floor has 9’ ceilings and oak hardwood floors throughout. French doors in the dining room open to a sunny side deck that flows onto an attached covered rear porch. For privacy, the main level guest bedroom and en suite bathroom are on the opposite side of the foyer. The spacious primary bedroom suite, on the second level, will be your serene and private retreat. The en suite primary bathroom includes a Kohler soaking tub, a tiled walk-in shower with a glass door enclosure, and a double vanity. A full bath and separate laundry room complete this lovely space. Enjoy the spacious backyard from your deck or covered porch, which can easily accommodate a pool and a two-car detached garage, offered as an optional upgrade, creating the perfect Vineyard dream. *Optional builder and appliance package upgrades are available. *Renderings are for illustrative purposes only. Construction details are governed by builder specifications and final construction agreement with Builder.

35 Double Ox Road

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.

00 Kennebago Avenue - 65-E-1

LUXURIOUS LIVING AT THE FIELD CLUB. Experience the epitome of luxurious and carefree island living at Seven Field Club Lane.  Designed by renowned architect Patrick Ahearn, this exceptional home is a masterpiece of superior architectural detailing. From the random-width oak floors to the custom millwork and raised paneling, every aspect exudes quality and craftsmanship. The open floor plan seamlessly integrates indoor and outdoor living, with four sets of French doors leading to the covered portico, terrace, and private yard. The professionally decorated interior, with its calming palette of sand and sea-inspired colors, creates a tranquil and inviting atmosphere. This elegant and classically-styled home offers a private membership to the Field Club, providing access to a wealth of amenities including swimming pools, tennis and squash courts, a full-service spa and fitness club, private dining options, and custom-designed activities for all age groups. Offered turnkey with exquisite indoor and outdoor furnishings, this meticulously maintained home is truly move-in ready. Additionally, the site plan includes designs for an Ahearn-designed pool and cabana, adding further allure to this already stunning property. Conveniently located between Edgartown Village and South Beach, this home offers easy access to both the vibrant town center and the sandy shores of South Beach. Embrace the opportunity to enjoy a sophisticated island lifestyle in this gorgeous, move-in ready home.

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7 Field Club Lane

Welcome to 24 Dark Woods Road, a beautifully maintained 3-bedroom, 3.5-bath Contemporary Colonial nestled in an upscale, tranquil neighborhood. This spacious residence abuts acres of Sheriffs Meadow conservation land, offering miles of trails, serene pond views and peaceful privacy at the end of a quiet road, yet is just a mile from the beach and closer to Edgartown Village. This association prides itself in complementing and maintaining the natural surroundings. 

Step into the entryway to a sunlit, front-facing kitchen featuring granite countertops, custom cabinetry and coordinated built-in desk. The open-concept living room boasts soaring ceilings, a commodious dining area and a wall of sliders leading out to a backyard deck perfect for outdoor living and future expansion. The first-floor primary bedroom with ensuite bath, second bedroom, full bath and study, provide convenience and comfort.
An open stairway leads to the second floor with a balcony overlooking the living room, where you'll discover a cozy versatile den, a large third bedroom, full bath and a bright office space. Thoughtful design elements include a central vacuum system, ample storage and energy-efficient features including solar panels and a modern heat pump system, backed by an oil heating option. Additional unfinished space on the second level as well as over the garage. The lush, irrigated yard and welcoming front hydrangea garden complete this idyllic offering.
With potential for expansion to 6 bedrooms, a spacious basement, and an EV-ready garage, this home is a rare find. Offered mostly furnished, it’s ready for you to make it your own.

24 Dark Woods Road

Vacant land in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of the Village. This wooded parcel is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool is allowed "by right" and so is a guesthouse after 5 years. The property, shown as Lot 4 in a "Plan of Land in Edgartown Mass" dated November 5, 2013 and revised May 22, 2023 (See "Documents" section), is awaiting a final judgment from the Land Court confirming good title in the seller, with only standard clerical steps remaining.

1 Wilsons Lane

Welcome to 12 West Farm Road, a delightful classic cape nestled among beautiful mature evergreens in the Coffins Field neighborhood of West Tisbury. This well-kept home features 3 bedrooms and 2 bathrooms, offering 1,389 square feet of cozy and inviting living space. Skylighted ceilings and an open first-floor living/cooking/dining area combination provide a spacious feeling for everyday relaxation or special occasion entertaining. An elevated rear deck off the dining area allows for nearby grilling while enjoying the outdoor greenery, blue skies, and sunshine.

The main level includes two conveniently located bedrooms for easy accessibility. Upstairs, you'll find a spacious loft area and an excellent primary bedroom, offering a serene retreat. A full unfinished walkout basement is ready for your creative ideas. The property sits on a gently sloping and generous  0.81-acre lot, providing a park-like canvas for your personal landscaping touches 

Centrally located in the Coffins Field neighborhood, 12 West Farm Road combines nearby island convenience with the potential to become your perfect retreat. Explore the possibilities that await in this charming West Tisbury home which is now available for the first time in 35 years. (Property is being sold furnished and as is).

12 West Farm Road

Edgartown opportunity—Finish off the seller's vision or create your own masterpiece! With over an acre of land, there is plenty of room to expand. Only two miles from lively downtown Edgartown, you get the privacy, beauty, and feel of the up-island without the commute. The lot can support a house, guest house, garage, and pool. Please no drive-bys.

4 Dubud Lane

CASUAL ELEGANCE ON KATAMA BAY.  Welcome to 25 Lelands Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappaquiddick. This magnificent home, nestled at the end of a private winding drive on 16.4 private acres, offers over 7,200 square feet of living space, designed for the ultimate luxury of spending treasured time with family and friends.

As you step inside, you'll be greeted by the warmth of four wood-burning fireplaces, handsome hardwood and painted floors, custom millwork and built-ins, a spacious screened porch and more! The rooftop widow's walk provides breathtaking 360-degree views, while the sparkling blue waters of Katama Bay can be seen and enjoyed from most every room in the house

This welcoming retreat features six bedrooms, all with en suite baths, including an exquisite three-room Owner's Suite with en suite bath, adjoining den/office, sweeping water views, and a private second-floor deck. Additionally, there is a three-room Family Suite on the second floor, complete with its own private living area and kitchenette.

The combined screened and covered porch, which extends nearly the full length of the home and overlooks Katama Bay, is a defining feature of the property, providing ample space for al fresco summer meals, reading, playing games, or simply soaking in the brilliant evening sunsets.

With over 320 feet of frontage on Katama Bay, this home offers ample opportunities for sailing, boating, paddleboarding, fishing, and clamming. Embrace the tranquility of life on Chappy, surrounded by sand dunes, tidal ponds and grassland habitats, with access to miles of unspoiled beaches and nature trails. There is an attached 3-bay garage for storing all your recreational gear including your island car, watercraft, bicycles, beach equipment and fishing gear!

The home was designed by architect Patrick Ahearn and is being offered turnkey, including hand-selected furnishings and accessories by interior designer Jon Hattaway of MJ Berries Design in Boston, adding objects and vibrant colors that delight the eye in every room. Enjoy this beautiful property as-is or bring your own design style and create your  signature coastal haven. Discover the perfect blend of casual elegance and serene waterfront living at this stunning Chappy waterfront retreat on Katama Bay.

25 Lelands Path

Located in picturesque Sweetened Water Farm on a 1.2-acre lot, lies this 3,400 square foot 5-bedroom, 3.5-bath traditional styled home. The primary entrance leads through a large eat-in kitchen to a dramatic 2-story cathedral ceiling Great room with a large stone fireplace at each end. There is a first-floor master suite and 4-bedrooms upstairs sharing 2 baths. The entrance road leads past rolling pastures and a beautiful horse barn and winds up through a wildflower filled field to the house. There is a large lawn and the property has mature landscaping creating a wonderful setting. A unique opportunity which offers a English country feeling while located less than a mile to Edgartown’s village center.

1 Louis Field Road

43 Peases Point Way South is where warmth and style meet sophistication, creating a truly one-of-a-kind living experience in the heart of Edgartown Village. Once you step through the gated arbor, you are welcomed by a lovely courtyard, creating the first of many unexpected and special moments carefully planned to provide the utmost privacy and tranquility, whether indoors or out. The Patrick Ahearn-designed home, just a short stroll away from Main Street shops, restaurants and the scenic Edgartown harbor, is elevated by its exceptional interior finishes and distinctive floor plan. Unparalleled luxury is carried through all levels of living, including an awe-inspiring outdoor space anchored by a remarkable salt water pool with a sunken fire pit and unique custom glass wall feature. Perfectly curated and luxurious furnishings only further enhance each space, making a turn-key opportunity possible. Recently completed, this phenomenal property has set a new elite standard.

43 Peases Point Way South

A rare opportunity in the iconic Abel's Hill Association which offers private association beach access, three tennis courts and walking trails. This multi-level Chilmark home was designed and built as an homage to architect Frank Lloyd Wright's ethos of open living spaces with flowing sightlines from room to room. The main house has a pocket view to the Atlantic that opens in the fall and winter months, wood floors, natural light and multiple levels. The living room features a contemporary Swedish woodstove and two skylights and sliding glass doors to a balcony making the space bright and cozy. The expanded primary bedroom suite is spacious and offers a private bathroom with generous jacuzzi tub. The kitchen and dining rooms open onto a large deck for entertaining that looks out over the back yard and lovely plantings. There are two guest bedrooms on the second floor separated by an open loft space currently being used as a study and sitting area. The lower level of the main house features a garage, additional storage, and a bonus room with private entrance. The studio style separate guest house offers a full bathroom and kitchen and is situated over a large barn storage space that could accommodate a vehicle or boat. The 1.4 acre property is surrounded by mature trees and abuts the historic Chilmark Cemetery, preserving the privacy and ensuring quiet neighbors. The private association barrier beach is a short walk from the house, or use the association's private beach parking. There are also kayak racks available for association residents to store their kayaks and canoes by Chilmark Pond.  The main house has solar panels powering all the electric and hot water in the home and the auto charging station. The main house features a whole house water purifier, ducted heat and AC. The main and guest have separate septic systems and both septic systems have passed Title V.

10 North Abels Hill Road

11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of this beautiful site, with a patio for entertaining and a dipping pool. A spacious shed has great storage for kayaks, paddle boards, surfboards and much more. Beautifully landscaped and ready for you to enjoy summer in Chilmark with additional beach access to Lucy Vincent and Squibnocket. An added bonus is the 240v ChargePoint at the driveway.

11 Greenhouse Lane

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

OAK BLUFFS IMPROVED PRICE~ APPROVED 4 BEDROOM SEPTIC IN PLACE -  This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan.  The main level displays beautiful hardwood floors, a bright open kitchen, and a charming dining area. The focal point in the family room is an attractive propane gas fireplace that creates the perfect space for entertaining. Step outside and enjoy the mahogany deck overlooking the expansive backyard surrounded by tall Leland Pines and many mature plantings. Sliders and large windows flood the interior with streams of sunlight. In addition, there are 2 delightful bedrooms each with custom "California Closets" and cabinetry. The lower level has one airy bedroom, a full bath, hobby room, laundry room, utility room and work out room. This property is a must-see treasure you will not want to leave. Features Central AC, lots of closets, garden shed, outdoor shower, cement driveway, and detached roomy garage. New Roof (2023) garden and hardscape. Whether enjoying indoor gatherings or outdoor activities, this home provides a perfect balance of comfort and versatility. The Two Story detached Studio is ideal for a Yoga, Art Studio or detached office!
The Possibilities are endless!

60 Prospect Avenue

East Chop-Near Oak Bluffs Center. This antique bungalow was lovingly restored to a modern year-round home by a Island craftsman. Completely rewired, replumbed, and insulated from the walls in and between the ceiling and roof. This roomy 2 bedroom 2 bathroom home has a complete basement below with finished rooms and separate laundry room. The fenced property provides privacy and outdoor comfort. with a garden and back deck **Sister property next door also for sale.**

14 Maple Avenue

Oak Bluffs- Walk to Beach and town center from this East Chop Bungalow. Lovingly restored by a local craftsman. Custom made throughout from the mosaic tile foyer, to the large open kitchen with tera cotta tile, the wooden vaulted ceiling and stone decorative fireplace in the living room. Two bedrooms each with a full bathroom en suite. An additional room being used as an office. A full finished basement with wide tiled stairs, floors, and walls. Laundry and rec. room and separate workshop are on this lower level. The house has 2 heating systems, new heat pumps for heat and air conditioning as well as a propane furnace. This fenced property has an outdoor paradise with a private yard, back area patio, and seating area, and side porch. **sister property next door also for sale.

12 Maple Avenue

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and custom cabinetry. The five spacious bedrooms are thoughtfully positioned throughout the home, providing unparalleled privacy and comfort. The main house features four private bedrooms with three full bathrooms and private balconies. The fifth bedroom is housed over the detached two-car garage. The detached two-car garage not only provides ample storage for vehicles but also features a private one-bedroom suite above, perfect for accommodating guests or serving as a tranquil home office space. The meticulously landscaped grounds are a true masterpiece, featuring a sparkling pool surrounded by a flagstone patio complete with an outdoor dining area and fire pit, making indoor and outdoor living seamless. This property offers both tranquility and convenience. Just moments away from the charming shops and restaurants of downtown Edgartown, and a short distance from the island's pristine beaches. A well rounded offering that should not be overlooked!

1 Field Club Drive

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore.

Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

64 Squibnocket Farm Road

Mattakesett units continue to be in high demand and Unit B2 is the latest to hit the market!  Take advantage of all the Winnetu Resort amenities and a robust rental program which covers your fees and provides great revenue! This unit offers abundant views of the farm fields out front, open common space next to and behind, and is a short walk or bike to South Beach! There are 3 bedrooms, 2.5 baths and the bonus of a finished loft.  With over 1,400 sq ft of living space this is one of the larger units. The outdoor rear deck offers additional space for dining or relaxing after a day at the beach. These units are seasonal, closed down in mid-November and re-opened starting in mid-April.  This unit is being offered fully furnished.  Showings can take place during rental turnovers on Thursdays between 12-2pm.

467 Katama Road B2

Embrace the history and character of this delightful 1870’s Oak Bluffs cottage. Formerly the Laura Thomas Smith House, it was relocated from the Vineyard Highlands area, nestled in a quaint neighborhood close to the center of town and the harbor. It was documented in a 1978 Oak Bluffs Historical Survey and has been in the same family for 98 years. This cottage features a sun-filled living room, vintage kitchen, one bath and mudroom on the first floor, with all 3-bedrooms on the second floor. The cottage radiates timeless appeal, with its painted pine floors, exposed beams, inviting covered front porch, and a second-floor deck to take advantage of the summer breezes. The home was upgraded with a new septic system in 2022, plumbing and 4 Mini splits for heating and cooling as well as other improvements along the way including an architectural roof, shed and hot water heater. With its ideal location, this cottage is a short stroll to all the attractions of Oak Bluffs, including the harbor, the library, restaurants and shops. Whether you're looking to winterize the property for a year-round residence, a summer vacation escape, or a potential rental property, this cottage offers a rare opportunity to own a piece of Oak Bluffs history. There is an established rental history. Property is being offered turnkey.

18 Brunswick Avenue

A rare opportunity to acquire exceptional property in Chilmark. This well maintained modern home is situated on a knoll overlooking the rolling hills with a perfect combination of forest and farmland and the Atlantic Ocean. The property boasts ancient stonewalls, intriguing glacial boulders, a small pond with stream and extensive well kept walking trails covering the entire property. The home consists of four bedrooms, three bathrooms, open kitchen/dining area, living room with fireplace family room and study. Extremely private, the perfect Vineyard escape.

44 Cencelle

Lovely five acre wooded lot off of South Road is ready to be yours. Located in a desirable neighborhood in the Quansoo area in Chilmark. Abuts conservation land on one side and ancient farm land on another. Your chance to build your dream home in a rural setting yet close to West Tisbury center. Access to Lucy Vincent and Squibnocket beaches.
Property has been surveyed, perc test completed and preliminary septic plan done.

90 Quenames Road

Prime 2-acre parcel situated close to the bike path, state forest, Morning Glory Farm and Edgartown village. Per Edgartown BOH, this lot is approved to support a 5-bedroom home with a standard septic system. Additionally, with an advanced treatment system and a variance, the potential exists to expand with one or two extra bedrooms. Enjoy the perfect blend of convenience and tranquility in this location. Don't miss out on creating your dream home in this idyllic setting. **Seller is in the process of NHESP review.

501 West Tisbury Road

Discover this Martha's Vineyard treasure, held by one family since 1968. Just steps from Seth's Pond, enjoy tranquil water views from the oversized porch. The home offers a balance of privacy and togetherness with a welcoming living room, dining area, and a walk-out basement for easy outdoor access.
The spacious yard is ideal for relaxation, and the pond invites swimming and kayaking. Located off Lambert's Cove Road, you have access to Lambert's Cove Beach and Long Point Beach with a beach pass.
This is your chance to revitalize a cherished home into your own Vineyard escape. Note that changes to the home's footprint may require approvals and permits from local authorities.
Septic System Compliance: Seller will cover costs to bring the septic system up to Title 5 and local regulations. An escrow holding 150% of the estimated cost (based on a seller-obtained estimate) will be managed by the buyer’s attorney until work is completed. Excess funds return to the seller upon completion. A neutral inspector will resolve any disputes.
Please Note: Septic upgrade is for compliance only; additional enhancements are the buyer's responsibility.
Own a piece of Martha's Vineyard history and make this lakeside property your personal retreat.

5 Scottys Lane

Sublime hillside site with old growth trees and walking easement to 16' of sandy lagoon pond beach.
This property is in the lagoon pond water shed and will require a NitROE denitrification component on the septic system. All information should be verified by the Vineyard Haven Building Department and Board of Health. Seller not able to close prior to October 31, 2024.

126 Border Road

Perfectly sited on a knoll with expansive water views at the head of the Lagoon, it is a few short steps to the private sandy shore for swimming, kayaking or continue down the pond out to open water. Designed by the owner's architect father (Nembhard Culin a renowned watercolor artist,) it worked as a solar-heated house for over 40 years. The non working hot air solar collectors have now been turned into a photovoltaic system so it is now 100% renewable electric. The award winning organic garden is being revived by the resident caretaker.

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5 baths, including a spa room, this residence offers both comfort and relaxation. The bright living room offers a gas fireplace with built-in shelving, and access to a wrap around porch and stone patio. The 2-car garage provides ample storage space. Located just minutes from downtown Oak Bluffs, this home offers convenience and charm. Don't miss the opportunity to own this fantastic property.

30 Franklin Avenue

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. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you can enjoy swimming and watching beautiful sunsets.  There is also a 1 car garage with a work space.

100 Gosnolds Way

EDGARTOWN VILLAGE - One block from Main Street sits an impeccably constructed home with an interior design that provides a sense of elegance and style. The luxurious indoor and outdoor living areas take entertaining to the next level. Resort-like grounds feature a covered open-air terrace with wood burning fireplace, heated Gunite pool, built-in BBQ, blue stone patios and beautiful landscaping. Indoors, antique wide pine flooring, wooden beams and five fireplaces throughout the home exude warmth and character. The entry foyer sets expectations at the door and has high ceilings, a coat closet, powder room, and a winding staircase to the second floor. A formal dining room, the living room, and the handsome wood-paneled library lend to entertaining, quiet reading, or intimate conversation. The kitchen is well-appointed and has a large center island, butler's pantry, and a sunken sunroom. There are five bedrooms in all, including two primary suites. Separate from the main living areas is a family room and billiards room ideal for evening entertainment or rainy days. Offered turn-key for immediate enjoyment. Boutiques, art galleries, fine restaurants and the harbor are just steps away.

15 Tilton Way

Welcome to your Vineyard Dream in the heart of West Chop! Built by Novo Builds, a renowned construction company that is recognized for their innovative designs and high-quality craftsmanship. Novo Builds is set to enhance the landscape of this iconic island with their latest development.

This stunning new build offers the perfect blend of modern luxury and coastal charm, making it an ideal sanctuary for families or those looking to entertain in style. The home has 5 bedrooms, 6.5 bathrooms and 4,216 sqft. With a six bedroom septic in place, the new owner has the option of adding a bedroom.

The open-concept design of the main living area ensures a seamless flow between the living room, dining area, and kitchen. High ceilings and large windows allow natural light to flood the space, creating a bright and airy atmosphere.

The state-of-the-art kitchen is a chef's dream, featuring top-of-the-line appliances, custom cabinetry, and a large island perfect for meal prep and casual dining.

Each of the five bedrooms is a private retreat, complete with en-suite bathrooms and ample closet space. The first floor master suite is particularly impressive, walk-in shower, dual vanities and master dressing room.

The beautifully landscaped yard offers plenty of space for relaxation and recreation. Enjoy al fresco dining on the expansive patio or take a dip in the sparkling 18X40 pool. Complete with a cabana the yard is your personal retreat for relaxation and entertainment.


Situated in West Chop, this home provides easy access to all that Martha's Vineyard has to offer, from pristine beaches, charming shops and fine dining. The estate is nestled near the prestigious West Chop Club, Vineyard Haven Yacht Club and Mink Meadows Golf Club. 

This new build in West Chop, to be completed summer 2025, is more than just a house; it's a lifestyle. Don't miss the chance to make this exquisite property your own and experience the best of Martha's Vineyard living.

*Renderings are for illustrative purposes only.

Architect plans and finish details available on request.

64 Crowell Lane

CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a day at Lucy Vincent Beach or on the boat. Pick up some local oysters and lobster rolls in Menemsha and then head home to enjoy a perfect summer sunset on the patio overlooking Menemsha Pond and the Elizabeth Islands. 
The home is pristine and private with many unique features that make it the perfect place from which to enjoy all that up-Island has to offer. The chef's kitchen and dining area are serene, bright, and functional. The main floor living spaces feature unparalleled Chilmark panoramas with views of South Shore beaches, Quitsa and Menemsha Ponds, and the Vineyard Sound. A stately wood-burning stone fireplace centers the living room which overlooks the expansive lap pool and stone patio area with dining space for outdoor enjoyment. The stunning main house has 4 bedrooms and 3 1/2 baths. The primary bedroom, on the main level, has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. 
This rare up-Island property also includes a secluded guest house with a well-appointed kitchen, two ensuite bedrooms, and a spacious living area with wood burning fireplace. A one-car garage on the property is a plus for storing all of your Island toys such as surfboards, beach gear, and the Island car. This Chilmark retreat also features deeded access for small boat pick-up and drop-off on Menemsha Pond, just across the way. Close to the Chilmark General store, Chilmark Tavern, Beetlebung Farm Stand, and the Chilmark Community Center for your convenience. However you like to spend your days, at the beach, by the pool, grilling with a crowd, or curled up with a good book in front of the fire, you can do it all at this one-of-a-kind Chilmark property. The co-listing agent is related to the Seller.

2 Squibnocket Road

EDGARTOWN - A RARE OPPORTUNITY to purchase a Newly Created Conforming Lot in a PRIME Edgartown location.  Build your Dream Vineyard Home facing Cannon Ball Park and opposite a row of newly constructed and existing multi million dollar properties.  Located within walking distance to Main Street Edgartown and all that Edgartown has to offer.  Once connected to the Town Sewer this lot qualifies for FOUR (4) BEDROOMS. An opportunity to build a luxurious property in one of the Vineyard's quaintest and most sought after towns.  Property is in R5 zone - Setbacks are 20 feet from the front and 5 feet from the side and rear boundaries.  Access from Cooke Street.

126 Cooke Street

OAK BLUFFS BEACHFRONT WITH DOCK -

Completed in 2024, this fully renovated three-bedroom, two-bath cottage offers sweeping views of Vineyard Haven Harbor, with private dock and an additional abutting parcel for extra privacy and expanded water frontage. The home seamlessly blends modern upgrades with classic Vineyard charm.

In the living room, a large picture window perfectly frames panoramic views of the harbor, setting the tone for this coastal retreat. The space features original wood floors, beadboard walls, and a cozy gas fireplace set against a real stone chimney wall. Flowing seamlessly from the living room, the dining area offers the perfect setting for memorable meals, accompanied by stunning water views. Adjacent to the living room is a sunroom, ideal for relaxing while enjoying sunsets over West Chop.

The fully updated cook's kitchen is a chef's delight with new appliances, double ovens, a gas stove, butcher block countertops, and a farmhouse sink. The layout comfortably seats six, creating the perfect space for guests to relax and chat while the chef works their magic.

The first-floor bedroom opens to an expansive Ipe hardwood deck with seating for eight, a propane gas grill hookup, and a custom outdoor shower. Upstairs, two additional bedrooms feature designer Annie Selke wallpaper, beadboard accents, and refinished original floors, creating cozy, inviting spaces. Both bathrooms are thoughtfully updated with designer tiles, ceramic floors, and luxury finishes.

A new mudroom and laundry room with ample storage makes this property both practical and picturesque. Additional recent upgrades include new shingles, shutters, plumbing, electrical, insulation, mini-split heating and cooling systems, new driveway and landscaping.

For pet owners, this home is fully equipped with dog doors and a fully fenced-in yard, making it ideal for those who want to bring their furry friends along.

With every detail meticulously attended to, this pristine property is truly move-in ready. All the work has been done, allowing the next owner to immediately enjoy the carefree coastal lifestyle and all the beauty that this exceptional Vineyard location has to offer.

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