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Discover beautiful homes for sale on Martha’s Vineyard’s South Shore. Enjoy coastal living with breathtaking views and serene surroundings.

South Shore

South Shore 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

This conforming 10,108 sq ft lot sits in the middle of a new 3-lot subdivision just minutes to Main Street.  It is approved and ready for nearby town water and sewer connections to accommodate a 4-bedroom residence.  A new private way is in, along with fire hydrants and power lines and the entrance is being improved by MA DOT.  With few Edgartown building lots available, this is an ideal location for your next project.  Note: The adjacent lot on the road is also available for purchase for a special package price of $2.6M.  Double the size of your lot, increase your building area, develop it, or sell it!

3 Ogden Lane

This charming 1942 two bedroom ranch-style home is part of a 3-lot subdivision located just a short walk to downtown.  The conforming lot is connected to town water and sewer, approved for 4 bedrooms. A new private road, Ogden Lane, has been created to allow access to the two lots in the rear.  A buyer can refurbish the existing cottage, expand, or build your Vineyard dream home from scratch.  With limited land listings, this is a great opportunity to be in a very convenient Edgartown location, close to the Village, school, library, bike path, Morning Glory, shopping, etc.  Property is being offered "as-is".  Note: the vacant lot behind is also available for purchase for a special package price of $2.6M for both lots.

87 West Tisbury Road

This conforming 10,169 sq ft lot sits on the road at the start of a new 3-lot subdivision, just minutes to Main Street.  The existing 1940's ranch is connected to town water and sewer, approved for a 4-bedroom residence.  A new private way is in, along with fire hydrants and power lines and the entrance is being improved by MA DOT.  With few Edgartown building lots available, this is an ideal location for your next project.  Note: The vacant lot behind this property is also available for purchase for a special package price of $2.6M.  Double the size of your lot, increase your building area, develop it, or sell it!

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

Classic turn-of-the Century building in the heart of Circuit Avenue's pedestrian bustle. This well-cared-for building has housed a vibrant clothing store for more than 30 years. There is ample window display space and high ceiling height and a newley created half bath. The expansive second floor, with lofty ceilings and a full bath is ready for creative use. It's finished interior includs skylights,bright living area with french doors to a spacious deck overlooking the charm of the Campground and providing access to two coveted, rear parking places. This seperate entrance creates possibilities for use or rental as professional office or studio space.. A large, clean basement for storage and the potential for expansion add to the appeal and versatility of this marvelous spot.

33 Circuit Avenue

Waterview beach house in Aquinnah! Just a short walking path to the calm and sandy waters of the North Shore beach. Traditional
layout with the kitchen, living, dining room and full bath on the first floor. The living room comes with water views and a cozy
fireplace, and multiple sliding doors that walk out to the wrap around porch. Upstairs the views are increasingly beautiful! Four
bedrooms share a full bath, one of the bedrooms has a fireplace while two have sliding doors that walk out to water view balconies.
The full walkout basement/garage offers plenty of room for a vehicle, extra storage or set up a ping pong table. This bright and
airy home is the perfect Aquinnah retreat.

654 Lighthouse Road

Welcome to this beautifully renovated 4-bedroom, 3-bathroom home nestled on a tranquil dead-end street, offering a spacious .92-acre lot and a fabulous finished basement. This property is the epitome of modern comfort and convenience, where every detail has been thoughtfully considered.
As you approach this charming home, you'll appreciate the quiet serenity of the dead-end street, ensuring minimal traffic and a safe environment for your family, and guests. The nearly one-acre lot provides ample space for outdoor activities, gardening, or simply enjoying the natural surroundings.
Step inside and be captivated by the meticulous renovation that has transformed this property into a haven of contemporary living. The open-concept design welcomes you with a bright and airy atmosphere. The heart of the home is the stunning kitchen, boasting Quartz countertops, and a generous island for both meal prep and casual dining. It seamlessly flows into the dining area and living room, creating a perfect space for entertaining and everyday living. 
The commitment to excellence in this home doesn't stop at the exterior and main living areas. Each of the bathrooms in this property has been completely renovated from top to bottom. These renovations ensure that not only the shared and private spaces are modern and functional but also offer a touch of luxury. 
Upon descending the stairs, you will discover a exquisitely finished basement, elegantly augmenting the available living area on the primary level.
This remarkable property unquestionably demands your attention. Kindly request a comprehensive list of the extensive enhancements available.

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69 Island Farms Road

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

Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as well as the primary bedroom suite and office on this upper level. This is a great house for entertaining and offers A/C, screened porch, generator, music system, outdoor lighting and other perks. The exterior space features a tennis court, beautiful gardens with water feature, and a cleared meadow, which is several acres in size, surrounded by woodlands. No other houses can be seen from here. A pool is possible and there is plenty of space for this addition. Subdivision potential. Includes Brickyard Beach rights.

49 Gosnolds Way

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

Welcome to 12 Mae Avenue, where laid-back island living meets timeless allure. This 3-bed, 2-bath gem boasts 1,700 square feet of pure Martha's Vineyard charm. Nestled in the sought-after Lagoon area of Oak Bluffs, this home offers breathtaking panoramic views of the serene Lagoon from nearly every angle. Step inside to discover the first floor, where a full bathroom and three generous bedrooms await, including an inviting primary bedroom with its own ensuite bathroom. As you make your way through the home, you'll find yourself drawn to the rear door, leading you to a covered porch adorned with not one, but two, roomy porch swings. Ascend to the second floor, where the magic continues. A spacious living room welcomes you with its lofty vaulted ceilings, creating an airy and inviting atmosphere. Adjacent, the dining room and kitchen beckon, offering the perfect space to entertain and create culinary delights while taking in the stunning views that surround you. Step outside through one of three large sliding glass doors to the upper porch, where automatic awnings provide shade for the ample outdoor dining and entertainment space. Whether you're hosting a lively gathering or simply unwinding with a glass of wine as you soak in the sunset, this outdoor oasis is the perfect extension of the home's charm. With its ideal location only steps from the Lagoon and close to downtown Oak Bluffs and offering picturesque vistas, 12 Mae Avenue is the quintessential Martha's Vineyard retreat. Whether you're seeking a peaceful getaway or a year-round haven, this home offers a classic charm with a touch of vintage allure, providing an opportunity to upgrade or renovate to match your unique style. Don't miss your chance to make this island paradise your own. This home also represents a good investment opportunity with a solid rental history. Furnishings available for separate purchase / negotiation.

12 Mae Avenue

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

THIS IMMACULATELY MAINTAINED AND UPGRADED HOME WITH GUEST COTTAGE AND NEW SEPTIC IS A RARE FIND! Situated on a quiet cul-de-sac and located only minutes from downtown Vineyard Haven, with its unique shops, restaurants, entertainment, markets, beaches, and more…. this five-bedroom home is MOVE-IN-READY! The owner has added many upgrades and renovations, including a charming studio guest cottage and finished walk-out basement.  Among the many newer renovations and replacements are: New Nitrogen mitigating Septic System, new Andersen windows, exterior doors and skylights; Irrigation system; Mini splits/Heat and AC installed throughout (in addition to the existing baseboard hot water heat); Hot water heater; All light fixtures replaced; All decks replaced with IPE lumber;… and more! The beautifully landscaped back yard, accented with statuesque Leyland Cypress trees, sprinkled with a variety of other tastefully placed shrubs and trees, creates a perfect island getaway in your own back yard.  Other features include solar panels, outdoor shower and hot tub!  Entering the front door, you’re greeted with a bright living and dining room area, kitchen with beautiful wood dining counter and beyond the kitchen, is the first-floor bedroom with a full bath across the hall with laundry room and new Samsung washer and dryer.  Moving back to the dining area –the double glass patio door opens to an immaculate and spacious 27 x 18 stone patio which flows into the spacious greenery. Beyond the patio, to the left, is the sweet guest cottage studio with kitchen and mini-split.  The “everyday” side entrance opens to a mudroom with convenient built-ins and coat hooks for easy storage.  Going up - the second floor boasts two spacious bedrooms and hall bath with skylight.  Both bedrooms feature custom built-ins as well as roomy closets with extra storage, cathedral ceilings and skylights for star gazing enthusiasts. The finished walk-out basement, including a sizeable fourth bedroom, full bath, generous family room (with upgraded large well window) and additional laundry area with more storage, completes this Vineyard GEM. A MUST SEE!!

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191 Spring Hill Road

This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below. The property is located in a very conservative minded, private area abutting Katharine Graham’s Mohu estate.

104 & 111 Old Herring Creek Road

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

Exceptional In-Town Opportunity:
A Canvas for Luxury Living in Oak Bluffs.
Discover a rare opportunity in the heart of Oak Bluffs, on Martha's Vineyard – a sprawling .6-acre lot offering a serene blend of natural beauty and prime location.
This property presents a unique opportunity to create a luxury residence with a design that honors the island's charm and your personal taste in upscale living.

Key Highlights:
Prime Location with Natural Splendor:
Experience the best of both worlds - a peaceful oasis boasting picturesque views of gardens, pine woods, and wetlands stretching to Sunset Lake and Oak Bluffs Harbor, while being just moments away from the vibrant harbor life, exquisite dining, entertainment, and sandy beaches.

Approved Plans for a Dream Home:
Included in the sale are approvals and plans for a breathtaking 2,500 sq ft home, masterfully designed by Breese Architects. The proposed 4-bedroom, 3-bathroom residence has received the nod from the Martha’s Vineyard Commission, Oak Bluffs Historic Commission, and Conservation Commission, ensuring a seamless transition from vision to reality.

Innovative Design and Elegance:
The architectural plans showcase a home elevated above natural grade, providing stunning water views from a second-floor balcony. The design cleverly incorporates two garage spaces beneath the raised floor levels, merging functionality with style.

Historic Charm Meets Modern Elegance:
While the exterior echoes the historic character of the original house, the interior proposes a bright, open concept with a striking vaulted ceiling in the great room and upper-level windows that bathe the kitchen and dining area in natural light.

Seamless Indoor-Outdoor Living:
Envision life in a space where the transition from indoors to outdoors is effortless, featuring a screened porch, open porches, and a balcony, perfect for savoring the tranquil surroundings.

This property represents more than just a home; it's a lifestyle choice for those who appreciate the blend of historical reverence and modern luxury. With demolition approval already in place for the existing structure, your vision for a distinguished living experience is ready to be realized.

Connect with me to explore how this property can be the canvas for your dream home, where luxury, location, and natural beauty converge.

17 School Street

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

Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The property is in an area of several multimillion-dollar homes and will accommodate a house, guesthouse, and swimming pool. The neighboring 3.2-acre lot (48.5) which includes 60 ft of water frontage on Vineyard Sound is also available for purchase.

11 Beach Pebble Road

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

Discover an exceptional opportunity at The Triangle in Edgartown with this commercial condominium for sale. Boasting ample parking, coveted high-visibility, and a very convenient location. With its strategic positioning, located at an important junction just off of Edgartown Vineyard Haven Road and within easy range of central Edgartown, it is sure to draw in customers and maximize your business' exposure. Don't miss out on this rare opportunity to secure your place in one of the most sought-after commercial units.

245 Edgartown Vineyard Haven Road 1

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

East Chop waterfront – Once in a lifetime, a property of this caliber becomes available, with an on-the-water East Chop location, a wide range of amenities, and multi-functional use! Uses include -- 1.) Currently operated as East Chop Harborfront Apartments, a pre-existing non-conforming use for the past 70+ years, 2.) Use it as a residential home or family compound, or live in a portion and rent a portion, 3.) Potential to convert to condominiums, paperwork presently in process 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 6-unit 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, heating/AC, 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. Private outdoor shower with dressing area. On town sewer.

47 East Chop Drive

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

NEW CONSTRUCTION: REIMAGINED ISLAND LIVING AT SOMERSET.  Summer is here and construction for 4 Somerset Lane is currently underway with a targeted completion date of November, 2024.  Somerset is an exclusive five-home luxury enclave perfectly located between Edgartown Village and South Beach -- and developed by Stanmar, owners of the Winnetu Oceanside Resort. This curated home has been perfectly designed for entertaining, peaceful relaxation, working from home -- and features spacious living spaces conducive to hosting and entertaining family and friends. The home sites have been designed to maximize outdoor living and entertaining around a spacious and private yard with expansive lawns and room for an in-ground pool, pool house/cabana and outdoor fire pit. The beautifully designed interiors will feature a fresh coastal style and will evoke a sense of casual island living and barefoot elegance. **ABOUT THIS HOME***: This smartly-designed luxury residence will include 3,643-square feet of finished interior living space -- with an additional 887 square feet of outdoor living spaces, including a spacious covered portico and second-floor screened porch -- for a combined total of over 4,530 square feet. Somerset offers a one-of-a-kind opportunity to own in premiere Katama location, with easy access to Edgartown Village, The Field Club -- as well as the bicycle path and South Beach.

4 Somerset Lane

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

UNPARALLELED LUXURY AWAITS AT THE HARBOR VIEW CAPTAIN’S COTTAGES - Near the end of North Water Street, overlooking Edgartown’s picturesque harbor and steps from the iconic lighthouse, sits the most storied hotel on Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay for all to gather for generations. Built in 1891 and after a top to bottom restoration in 2018 and extensive modernization again in 2021, this charming and sophisticated resort is offering the opportunity of fully managed residences with deeded ownership providing the splendor of Vineyard homeownership without the worry of maintenance and property management. Sprinkled across the property, the Harbor View Captain’s Cottages provide all of the hotel’s refined amenities. This gorgeous 2-Bedroom, 2-Bath second floor residence is located in the Captain Rowley Cottage and features fresh and inviting spaces with furnishings that evoke Vineyard style and life lived near the sea. There is a private outdoor shower and front and back private porches! Enjoy morning coffee on the veranda before a day lounging at the pool and cabanas. Have the Concierge book a tee time or pack a picnic for your afternoon relaxing with a book at Lighthouse Beach. Gather for sunset cocktails before dining at the hotel’s award winning Bettini Restaurant, while the Chef prepares your favorite meal. Bicycle or stroll around Edgartown Village and enjoy the many art galleries, shops and restaurants surrounded by the beauty and historic charm of the village. Ownership at the Harbor View Captain’s Cottages has been thoroughly contemplated to offer the finest service and unsurpassed experiences for Vineyard lovers of all ages. Owners enjoy a myriad of benefits including dining and beverage discounts at the hotel. There is also a fully managed rental program available for when owners are not in residence. The Harbor View Captain’s Cottages offer easy and carefree second home ownership with the opportunity for idyllic in-town living.

131 North Water Street 62 - Captain Rowley Cottage

Enjoy the convenience of Dark Woods, a quiet neighborhood in an ideal location close to the Village, bike path, beaches, and 27 acres of Sheriff’s Meadow conservation land. Tucked in the woods of the pleasant Dark Woods community, this property has been meticulously maintained and is ready for your enjoyment. Sited on a pleasant .77-acre lot, the property offers expansive space with a floor plan that is perfect for entertaining. The first floor features a fabulous living room with a gas fireplace and a formal dining room. Overlooking a private backyard is the open eat-in kitchen with direct access to a 2-tiered deck with a hot tub and outdoor shower, where you will spend much of your time entertaining. A bar/pantry is conveniently located between the dining room and kitchen, and a laundry room off the kitchen. If you are looking to retreat, enjoy the bonus space above the 2-car garage. The primary ensuite with a newly renovated bathroom is cleverly located on the right side of the second floor for privacy and 2 large guest bedrooms and another newly renovated bathroom complete this floor. The lower level enjoys a large walk-out bedroom with direct access to the backyard and a living and dining area with a wet bar and full bath. The home is connected to town water and sewer with the ability to expand to 7 bedrooms. Being sold furnished and ready for immediate occupancy, this highly coveted Dark Woods neighborhood offering is a home you don't want to miss! The listing agent is related to the seller.

43C Dark Woods Road

UNPARALLELED LUXURY AWAITS AT THE HARBOR VIEW CAPTAIN’S COTTAGES - Near the end of North Water Street, overlooking Edgartown’s picturesque harbor and steps from the iconic lighthouse, sits the most storied hotel on Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay for all to gather for generations. Built in 1891 and after a top to bottom restoration in 2018 and extensive modernization again in 2021, this charming and sophisticated resort is offering the opportunity of fully managed residences with deeded ownership providing the splendor of Vineyard homeownership without the worry of maintenance and property management. Sprinkled across the property, the Harbor View Captain’s Cottages provide all of the hotel’s refined amenities. This gorgeous 2-Bedroom, 2-Bath second floor residence is located in the Captain Collins Cottage and features fresh and inviting spaces with furnishings that evoke Vineyard style and life lived near the sea. There is even a private outdoor shower! Enjoy morning coffee on the veranda before a day lounging at the pool and cabanas. Have the Concierge book a tee time or pack a picnic for your afternoon relaxing with a book at Lighthouse Beach. Gather for sunset cocktails before dining at the hotel’s award winning Bettini Restaurant, while the Chef prepares your favorite meal. Bicycle or stroll around Edgartown Village and enjoy the many art galleries, shops and restaurants surrounded by the beauty and historic charm of the village. Ownership at the Harbor View Captain’s Cottages has been thoroughly contemplated to offer the finest service and unsurpassed experiences for Vineyard lovers of all ages. Owners enjoy a myriad of benefits including dining and beverage discounts at the hotel. There is also a fully managed rental program available for when owners are not in residence. The Harbor View Captain’s Cottages offer easy and carefree second home ownership with the opportunity for idyllic in-town living.

131 North Water Street 22/22A - Captain Collins Cottage

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

Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedroom, 1-bathroom apartment attached to the home, providing a perfect space for guest accommodation. With a generous 2,954 square feet of living space, there's plenty of room to live and entertain comfortably. The fully finished basement provides a versatile space that can be used as a home gym, office, or entertainment area. Step outside to a very peaceful backyard and patio, ideal for relaxation and gatherings. Enjoy the outdoor seating area, a grill with a direct propane line to the house, a charming goldfish pond, and a two-seat bar with water and electricity. Additional storage is provided by an outdoor shed and a separate 1-car garage. The property also features fully-installed solar panels, providing an excellent opportunity to reduce your electric bill with clean, renewable energy. Don't miss the opportunity to own this exceptional property in a great neighborhood in Oak Bluffs just 1 mile from the beach and downtown.

Property being sold unfurnished, AS-IS.

9 Goode Street

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

Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This main house and guest house are perfectly sited on just over 2 acres and are ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. Guest house needs finishing and presents a number of possibilities. Both structures are sited with the potential to expand, and according to the West Tisbury Board of Health, the property can support up to 8 bedrooms. This property is being sold "as-is".

41 Old County Road

This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground and fire pit with outdoor seating on wraparound deck, covered porch and around fire pit. The front and side covered porches lead to the outdoor shower. The first floor has hardwood flooring throughout, and the living room is open to the kitchen area. A separate formal dining area is off the kitchen with a full bathroom located in between. The primary bedroom has vaulted ceiling, tiled bathroom with air bubble jet tub and large walk-in closet. The second floor has four generous size carpeted bedrooms and a full bathroom. The lower level has a finished room creating additional living space to enjoy. The laundry room is in the basement with a sink and storage cabinets and the house is equipped with a central vacuum system. Many recent updates include a new furnace, AZEK exterior trim and deck railings. Currently a five-bedroom dwelling with a septic design for six bedrooms. A great investment property for year-round living or rental income. Come take a look while still available!

32 Flamingo Drive

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

CHARMING VINTAGE HOME IN THE HEART OF EDGARTOWN VILLAGE. 

Nestled within lush perennial gardens and surrounded by hedges and a classic picket fence, the Charles W. Crowell House is a delightful antique home that captures the essence of a bygone era. With its origins dating back to 1760, the home boasts beams crafted from trees that once grew on the property. These timeless timbers are prominently showcased throughout the home, adorning the ceilings and walls with their enduring presence.

Renovated in 2010 to incorporate modern conveniences such as updated electrical, central air conditioning and refreshed kitchen and baths, the residence has seamlessly blended contemporary comfort with its original period charm. Noteworthy features include an wide-planked pine flooring, two original fireplaces, and exquisite period millwork, as well as built-in cabinets and bookshelves.

Comprising a total of four bedrooms and three and one-half baths, including a first-floor Primary Bedroom, this home offers both space and intimacy. The private backyard features a brick terrace and is enclosed to create a serene retreat for dining al fresco, unwinding with a good book, and relishing the beauty of the surrounding gardens.

Located in the heart of historic Edgartown Village, this beloved antique home provides an exceptional opportunity to embrace the quintessential Vineyard lifestyle and create lasting memories for years to come.

2 Green Avenue

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.

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