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Explore homes for sale in Martha's Vineyard.

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

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

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

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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

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

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

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

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

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

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

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

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

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 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

Located at the end of Sweetened Water Farm, on nearly 5-acres, lies this property with incredible and expansive views across open fields to the horse pasture and barn. There is a 5-bedroom, 3-bath main house featuring an open floor plan, a screened porch and spacious deck. Additionally, there is a 6-stall horse barn with a large one-bedroom apartment above. The peaceful and quiet setting is complimented with stone walls, gardens and large expanses of manicured lawns.  This is a very special offering which is in great condition and wonderful as it stands, but could be reimagined to create an extraordinary family compound in a country setting, all within minutes to downtown Edgartown.

25 Beetle Swamp Road

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The french doors open to a deck overlooking the manicured lawn. A state-of-the-art media room, complete with comfortable seating, a large screen, and high-quality audio visual equipment. It's the perfect spot for movie nights, game days, or simply relaxing with friends and family along with a wine cellar just steps away. The carriage house features a three-car garage, providing ample space for your vehicles and storage needs including a large one bedroom and bath upstairs.  Katama Bay View Road is located adjacent to Sheriffs Meadow Conservation land and public access to Katama Bay. Conveniently located near South Beach, one of Martha's Vineyard's most beautiful and sought-after beaches.

24 Katama Bay View Road

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS.  Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor.  NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling.  Septic permits in place for two lots.  Lot #1 - 147.2 (45,782sq.ft.) Permit in place for an APPROVED 6 Bedroom Septic System;  Lot #2 - 147.3 - (31,320sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #3 - 147.4 - (34,824sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #4 - (52,451sq.ft.)  6 Bedroom Septic System Designed, NOT YET submitted; Lot #5 - (45,074sq.ft.) - Permit in place, APPROVED for a 4 Bedroom Septic System.  Lot # 5 - May have access directly from Wapello Street.  Ten (10) Bedrooms have been approved.  Applications for an additional Twelve (12) Bedrooms are in process.  Lot#2 - Application for 6 bedrooms. Lot#3 - Application for 6 Bedrooms.  Lot #4 is undetermined at this point.  Access may be allowed via Sunset Road or Eastville Avenue.  Water is available via Sunset Road, at the property.  Electricity is on site.  Buyer is responsible for verifying any and all information on this property.

0 Eastville Avenue

Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working wood-burning fireplaces, and the roof, windows, exterior doors, decking and siding have all been replaced within the last 10 years. The interior layout is ideally suited to taking in the views and spectacular sunsets, with an open kitchen, dining and living room that connect to a spacious deck and screened porch. The primary suite also connects to the deck and has views to the water. Guest bedrooms are on the ground floor and are privately set. The land is generous and beautifully landscaped, with a half basketball court carved in along the drive up to the house. Located just a short drive or bike ride to Menemsha and all town beaches, the setting is private, convenient and quintessentially Chilmark.

31 North Slope Lane

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

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

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

46 Red Buoy Lane

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

22 Paddock Road

On approximately .40 of an acre this 21 year old home has much to offer. In a very convenient location close to the
Farm Neck golf course,  O.B. elementary school, and a land bank conservation property - the 72 acre Tradewinds Field Reserve dog park. Two decks provide summertime fun and the walk out basement with bath offers an opportunity to finish off more living space. An excellent floor plan lends itself to entertaining.

10 Nunes Way

KATAMA - CONSTRUCTION IN PROGRESS - This elegant home sits on a spacious lot in a new 5 home luxury private enclave with breathtaking views of the surrounding pastures. The property offers privacy, a serene and picturesque setting, perfect for those seeking tranquility and natural beauty yet a convenient 1.6 mile distance to Edgartown Village. With meticulous attention to detail, this home boasts luxurious amenities and modern comforts, providing an exquisite living experience. Sewer connection permits expansion of UP TO 7 BEDROOMS. Enjoy the 18X42 saltwater, gunite pool! Don't miss the opportunity to make this stunning property your own!

61 Division Road

KATAMA CONDOMINIUM IN MEETINGHOUSE VILLAGE - A bright and sunny center unit with an open floor plan, vaulted ceilings, skylights, and windows that fill the space with natural light. This home is in excellent condition, showing the pride of ownership. The wide-open kitchen with a breakfast bar offers a wonderful space for cooking and entertaining. Accommodations include a first-floor bedroom with a full bath and a second-floor primary suite. Outside, you will find a private back deck, beautiful garden and open lawn. The newly appointed Association swimming pool is close by. Located in the highly desirable Katama area, this home sits less than two miles from South Beach and even closer to Edgartown Great Pond. This private community is a hidden gem, ideal for year-round living, a vacation home, or a rental investment.

17 Meetinghouse Village Way

This captain’s home built in 1850 lies on a double sized lot with expansive views of Edgartown Lighthouse and the entrance to the harbor. The home went through a full renovation years ago, updating the kitchen, bathrooms, opening up the floor plan and freshening all surfaces, while maintaining much of the original historic features. The street level of the home features an open floor plan with kitchen, family room, dining and living room, all which open up to an enormous exterior deck and enjoying incredible views. The second floor features a master suite with private bath and three additional bedrooms sharing two baths. There is a finished, cathedral ceiling third floor that could be used as additional bedrooms or recreational usages. The lower level offers two additional bedrooms, a full bath, living area and laundry. There is a guest house set on the lower lawn offering one bedroom, a full bath, living room with kitchenette and a charming, covered porch with direct views of the harbor. The property offers ample parking, beautiful landscaping and a huge front lawn which stretches to the harbors edge with sandy shoreline and a deep-water pier. A very rare opportunity to acquire a significant waterfront home on Edgartown’s inner harbor and with an exclusive North Water Street address.

111 North Water Street

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon entering, you'll be greeted by a sophisticated interior with open-plan living spaces designed for easy entertaining. The main level features sleek modern furnishings, flowing from the kitchen and dining area through French doors to a beautifully landscaped outdoor patio, ideal for al fresco dining and relaxation. Beyond the patio, a lush lawn and manicured gardens surround an impressive 42' x 18' swimming pool, creating a true outdoor oasis. The second level houses four spacious bedrooms, including a luxurious primary suite with an office, ensuite bath, and a private deck overlooking the pool. The third floor offers a large sleeping area with six twin beds, a full bath, a game area, and French doors leading to a sun-drenched deck. Perfect for family living or hosting guests, this home combines historic character with the finest modern conveniences. Located on North Water Street, this light-filled property is an exceptional opportunity to own a one-of-a-kind retreat in one of Edgartown’s most desirable locations.

68 North Water Street

Lowest Price in Aquinnah! - Rare opportunity to own this Single Family Home, in the natural serenity of Aquinnah, situated on 1.1 acres! Step onto the wrap around deck and enjoy the ocean views before going inside to the inviting kitchen and dining room, with stunning natural light coming from the windows and skylights that leads into the sitting area. The left wing has 3 bedrooms down the hall with one half bath and one full bath. To the right is the great room with cathedral ceilings, large expansive windows giving you the ocean view from inside, half bath with laundry hookup to the side. Step downstairs to the walk out lower level room, full bath, and additional room. Outside has a heated studio/shed to give your work area a year round home with two additional storage sheds, and outdoor shower. This home was uniquely built and loved by one family, come make this your family oasis! AS IS SALE

453 Lighthouse Road

Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system.

2 Other House Road

7500 sq ft+ commercial office building in the Waterfront/Commercial District of Vineyard Haven. There are currently 10 rented office spaces with several long-term tenants in place who enjoy the building's excellent condition and waterfront location with stunning views over both the Harbor and Lagoon. Located less than half a mile to the ferry and downtown Vineyard Haven. Financials are available with a signed NDA. Note: Monthly fees for each unit are calculated based on the square footage of that unit. Showings on Sunday only and with minimum 48 hour notice.

151 Beach Road

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

249 State Road

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

10 Tilton Way

Nestled in a private neighborhood in Vineyard Haven conveniently located to the ferry and town for plenty of shopping and dining, this renovated home is move-in ready and sited on 1.5 generous acres. There are two entrances to the home. The most operational is off the side deck where you enter the fabulous must-have mudroom. Offering separation from the main part of the home is a dramatic cathedral-ceiling Great Room with a wood-burning stove where you will occupy most of your time. There is an office area set aside in this room and a cleverly designed spiral staircase with a loft perfect for overflow. Entering the opposite side of the home you will enjoy the open floor plan with a fully renovated kitchen, dining room, and living room with another wood-burning stove. A renovated full bath with laundry and a first-floor bedroom complete this floor. There are two large bedrooms with skylights for great natural light and another large fully renovated full bath on the second floor. The unfinished basement has room for storage. You will love the stunning professionally landscaped yard with a patio, mature plantings, an outdoor shower, and room for a pool. There is a ZBA-approved pool plan and permit in place. If you are interested in renting, this property has a solid rental history. This property offers ultimate privacy and is not to be missed! The property is in the Tashmoo watershed and will require an upgrade to an Enhanced Nitrogen Septic system.

97 Snake Hollow

Spectacular, private beach lot located just off Moshup Trail. Gated entry, parking rights and a deeded 1/5 acre of beach on the Atlantic. This is not a buildable lot, no structures of any kind are permitted. Lot 7-5

00 Moshup Trail

This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven’s most quiet and quaint neighborhoods.  With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also features a renovated garage with a finished second level, perfect for a creative studio. Inside, the home exudes warmth and elegance, with wide pine flooring, custom craftsmanship, and intricate wood detailing on the ceilings. The spacious living room, centered around a gas fireplace, is both inviting and stylish. The sunlit kitchen, equipped with top-of-the-line appliances and refined finishes, includes a cozy window seat that adds to its charm. The primary bedroom suite offers a serene retreat, complete with a private tile bath and access to a 2nd-floor deck. The three additional bedrooms are equally comfortable and well-appointed, providing ample space for guests. The finished lower level expands your living space further, ideal for a home theater, gym, or playroom. Spend your days soaking in this privacy that this tranquil abode provides, or take advantage of its ideal location to access the hustle and bustle of downtown Vineyard Haven where you can enjoy various galleries, shops, and fine dining.  This location is also convenient to Owen Park Beach, West Chop and Mink Meadows Golf Club.

36 Tashmoo Avenue

In the heart of Katama, close to south beach and all that the area has to offer, is this traditional 3 bedroom cape with updates. The bright kitchen and dining area offer a modern space, perfect for entertaining. A vaulted ceiling makes the living room light and bright. Three bedrooms, two up and one down, share bathrooms on each level. An outdoor shower,  screened porch and outdoor decks make the indoor / outdoor transition comfortable. This property has an excellent rental history, or make it your island getaway or year round home. Offered turnkey, As Is.

6 Gerts Way

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

26 Curtis Lane

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

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

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

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

211 Upper Main Street & 26 Curtis Lane

A unique opportunity to own a one of a kind property with capacity for twenty people complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first level. The potential opportunity to subdivide this parcel only adds value to this well-rounded offering. The property is being offered turn key with the opportunity to own a very profitable business. This offering is for both the current business and the real estate. Just a short distance to downtown Vineyard Haven, the harbor and the ferry, look no further for your future investment!

11 Macs Lane

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

15 & 27 Pennywise Path

The Katama General Store, fondly known as the "Heartbeat of Katama," has been a beloved community landmark on Martha’s Vineyard since 1995. Reestablished with a new building in 2017, this store is ideally located just a half-mile from historic downtown Edgartown and close to South Beach, making it a vital stop for locals and tourists alike.
Offering a fully equipped commercial kitchen and modern retail space with over 2,000 square feet on the ground level featuring a vaulted ceiling and abundant natural light.  The upper and main levels offer bright, spacious prep, office and storage space.   The property also offers extensive outdoor amenities, including a covered 1,800 square-foot wraparound porch and 4,300 square-foot landscaped picnic event area with 25 dedicated parking spaces. This property combines historic charm with robust operational capability.
This property is a true community hub, offering local produce, gourmet foods, and specialty items, and serving as a gathering place for the Edgartown area. The opportunity also includes a seasonal wine and beer license that is transferable to the new owner upon approval from the Town of Edgartown, adding further value for expanding the business's offerings.
This sale includes all commercial equipment, fixtures, and furnishings, creating a seamless path for the next owner to continue building on the Katama General Store's 22-year legacy. Own a piece of Martha’s Vineyard history with a property poised for continued growth, community engagement, and connection.

170 Katama Road

The Katama General Store, fondly known as the "Heartbeat of Katama," has been a beloved community landmark on Martha’s Vineyard since 1995. Reestablished with a new building in 2017, this store is ideally located just a half-mile from historic downtown Edgartown and close to South Beach, making it a vital stop for locals and tourists alike.  Offering a fully equipped commercial kitchen and modern retail space with over 2,000 square feet on the ground level featuring a vaulted ceiling and abundant natural light.  The upper and main levels offer bright, spacious prep, office and storage space.   The property also offers extensive outdoor amenities, including a covered 1,800 square-foot wraparound porch and 4,300 square-foot landscaped picnic event area with 25 dedicated parking spaces. This property combines historic charm with robust operational capability.  This property is a true community hub, offering local produce, gourmet foods, and specialty items, and serving as a gathering place for the Edgartown area. The opportunity also includes a seasonal wine and beer license that is transferable to the new owner upon approval from the Town of Edgartown, adding further value for expanding the business's offerings.  This sale includes all commercial equipment, fixtures, and furnishings, creating a seamless path for the next owner to continue building on the Katama General Store's 22-year legacy. Own a piece of Martha’s Vineyard history with a property poised for continued growth, community engagement, and connection.

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

9 North Neck Road

This beautifully designed and built home is privately sited on 12.23 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views,  tall ceilings, a field stone fireplace and concrete floors heated by radiant heat. French doors take you out to a stone patio overlooking a meadow and distant ocean views. The well equipped eat-in kitchen is sun-filled with a center island, granite counters, top of the line appliances, a butlers pantry and a stone fireplace. The spacious family room is privately tucked away and features nice built in shelving and room for an oversized TV station. First floor primary features en-suite bathroom with oversized shower and soaking tub, french doors to a private porch. There are two stairways that take you to the second floor offering 4 spacious bedrooms, 2 full baths and a roof deck for enjoying the exceptional ocean views. Wood and tile floors, a full basement, propane FHA and a "monster" whole house generator. There is also a detached 3-car garage offering plenty of storage for bikes and kayaks with a charming second floor 1 bedroom guest apartment for extended family or guests. Plenty of room for a pool. Potential for 2 more building sites. Philbin town beach access and up-island living at it's best!

19 Locust Lane

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

4 Boldwater Road

Ocean views - Nestled on a quiet corner lot, this classic beach house  offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain. It is only 1.5 miles to South Beach and just under 2 miles to the heart of Edgartown village. The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus an 2 additional bedrooms and full bathroom. For 30 years the property has been a generational meeting place for the owners, their family, and friends, and now they are passing the baton on to its future owners. Enjoy it “as is” or put your vision to work to create a brand new Katama beach house to make your own memories.

18 Katama Drive

GROVEDALE BUILD YOUR DREAM OPPORTUNITY - Along a quiet country lane and close to all Oak Bluffs has to offer, this level lot is located in a neighborhood of nicely landscaped homes. The pride of ownership is apparent in this locale. There are not many opportunites like this left on Martha's Vineyard.

0 Concord Avenue

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

9 Weston Avenue

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

Main and second floors combine over 3,400 square feet of spacious, elegant living.  The partially finished lower level abounds with an additional 1891 sf, opening even more possibilities for unique customization to suit any lifestyle.

Three of the four bedrooms are en suite with all four quarters well separated, adding wonderful privacy from the next.

The show-stopping central staircase with its grandeur and contour adds a touch of elegance to the home, complemented perfectly by the warmth and sophistication of the maple inlay flooring, which is comfortably radiant heated throughout all three floors.

Despite its proximity to the bustling village life, the thoughtful sound-proof design allows for quiet relaxation when desired. The abundance of French doors not only brings in natural light but also seamlessly connects indoor and outdoor living spaces, enhancing the overall inviting atmosphere of the home.

Overall, this superb Edgartown Village property offers exceptional location with a unique blend of charm and elegance, making it a wonderful investment for those seeking a truly special home in the highly desirable Village of Edgartown.

62 North Summer Street

Sited on a pleasantly landscaped lot in sought-after Edgartown Estates, this desirable Katama location is equidistant between the Village and South Beach, with easy access to the bike path and proximity to Morning Glory Farm. 87 Schoolhouse Road is a charming gem with two large primary suites, loads of natural sunlight, a cathedral-ceiling living room, and slider doors off the kitchen to a patio for outdoor enjoyment. This pristine move-in ready home with a full basement and AC has been loving maintained with many updates including a new roof, shingling, a new furnace, new irrigation and professional landscpaing. This fabulous offering enjoys all the components of a Vineyard dream home. Being sold furnished this property is not to be missed!

87 Schoolhouse Road

The Preserve at the Woodlands - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two sides. The lot will support 6 bedrooms, has been perk tested and is ready for you to build your ultimate Vineyard compound.

34 Paddock Road

Panoramic Ocean Views can be enjoyed from each level of his thoughtfully built 4 BR home designed for easy Summer enjoyment or 4 Season living. It is wonderful in every way. It is built into the hill, so the first floor feels like a 2nd floor. Downstairs is a large open space to create a family room, or use it the way it is as a home gym/spa with state of the art equipment included. Energy efficient, private, easy access, plenty of outdoor space that has huge potential since the home takes up only 1/3d of the property. Enjoy complete privacy from neighbors or the road, nestled into a hillside where bird life abounds, yet convenient to dining at the Outermost Inn, Lighthouse and cliffs.

The home is lavishly laid out over 2 levels and provides over 3000 ft. of living space. A wall of glass on both levels for the enjoyment of the uniquely insteresting, forever protected vistas across a one of a kind beauty of the pristine fauna and flora of Aquinnah. There is nothing obstructing the views to the horizon with the Elizabeth Islands, and Menemsha hills. Watch the sailboats glide by and relax in style and comfort in this wonderful space. All Aquinnah Beaches are accessible within a short distance. Price has been drastically reduced by motivated Seller! House comes Turn Key for immediate use. Fully furnished and ready to go right now, or Enjoy your first Summer 2025 at this fabulous Vineyard Coastal home.

382 Lighthouse Road

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable lot. For 35 years, home of Susan Branch, the illustrious self-taught artist and author of New York Times best-seller "Martha's Vineyard, Isle of Dreams," this quintessential Greek Revival gem with Neoclassical touches enjoys over 3,300 s.f. of living space on more than a half acre in town with wood floors throughout and day long, east to west sunlight. With period paneling, crown molding, and 9' ceilings, the floor plan includes front hall entry with lovely curved staircase, front parlor-studio, formal living room with fireplace and bay window, spacious dining room, second side entrance vestibule used as a dry bar,  cozy wood paneled study/tv room, eat-in kitchen with wainscotting, east-facing side porch, laundry/storage room, and a half bath. With a convenient back staircase off the kitchen, the second floor includes additional spacious rooms:  A large primary bedroom with fireplace and ensuite bath, sitting room, three additional bedrooms, one with bay window, plus two additional full baths. Wonderful two-story carriage house - barn, expansive lawn and yard, tea-house pergola for afternoon tea, cocktail social, and alfresco dining.  Seller has plans for potential renovation of the barn to include a studio apartment - see Documents. Mature plantings including privet, flowering trees and bushes, perennials, historic Linden trees, and herb garden. Six bedroom approved Title 5 septic. A rare opportunity for those who appreciate the history and value of historic homes in a sailing port which as been described as "the sweetest little harbor on the east coast." *Extensive list of furnishings and household items available for purchase by separate bill of sale.  This property and the owners abutting Town Approved Building Lot comprised of 12,527 s.f on William Street is available for purchase together for $3,800,000.

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