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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.

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26 Curtis Lane

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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.

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211 Upper Main Street & 26 Curtis Lane

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

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

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

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

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

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

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72 Chappaquiddick Avenue

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

63 Division Road

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

79 Beach Road B13 and B14

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

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

56 Holmes Hole Road

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite. 
Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses.

25 Fulling Mill Road

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

37 Circuit Avenue 4

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

37 Circuit Avenue 5

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

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

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

46 Red Buoy Lane

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

34 Windemere Road

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

96 Dunham Avenue

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

16 Shotnaigher Lane

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

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

47 East Chop Drive

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

47 East Chop Drive Unit 5

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

47 East Chop Drive Unit 4

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

47 East Chop Drive Unit 2

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

47 East Chop Drive Unit 3

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

4 Jacobs Neck Road

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

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33 Boldwater Road

This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this special piece of land. Peaceful and private, this area is next door to 184 acres of conservation land at Waskosim's Rock Reservation, with miles of walking trails. A 4-bedroom septic has been designed by Sourati Engineering which could be expanded. A guest house is also possible with proper permitting. Natural heritage approval is in process. The lot is part of the Association tennis allowing a future owner access and usage of the community tennis courts. Chilmark residents enjoy the ocean beaches of Lucy Vincent, Squibnocket, and Vineyard Sound beach featuring the celebrated sunsets at Menemsha.
*NOTE: Architect Peter Breese designed an elegant potential 4-bedroom home on this land for the current owner that she is willing to share with a Buyer.

37 Bijahs Way

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

47 East Chop Drive Unit 1

A combination of luxury, comfort, and natural beauty, this expansive custom, five bedroom, post and beam home is sited on more than eight acres of land, surrounded by acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow from one room to the next, perfect for entertaining or simply enjoying daily living. The great room features a beautiful custom Johnny Hoy stone fireplace, cypress ceiling, white ash flooring, and custom cabinetry. High end chef's kitchen with breakfast bar opens into the dining area. Home has state of the art technology, solar panels, and an elevator. From the screened porch, with a second custom fireplace by Johnny Hoy, to the expansive finished basement with media room, this home invites you to enjoy many amazing spaces. Main floor offers the open living concept as well as a separate den, two offices, and two bedrooms, including the primary bedroom suite with office and bathroom. Single story living as well as handicapped accessibility and generational living is possible with this floor plan. In addition to the media and rec room, the lower level has ground floor living space as well as two additional bedrooms, one full baths and a 1/2 bath in the theater room. The beautiful, professionally landscaped yard leads you to a two story post and beam 48x52 barn. Every detail of this home has been carefully designed to exceed your expectations. Impeccable craftsmanship elevate this home to a level of luxury that is unmatched. Don't miss out on the opportunity to make this dream home your home.

71 Stoney Hill Road

Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious floor plan offers four bedrooms and four full bathrooms, complemented by two powder rooms and a fully finished lower level for additional entertainment. Separate guest quarters above the garage provide visitors with their own private retreat, featuring a dedicated living room, convenient wet bar, and private deck. Outdoors, a mahogany deck overlooks beautifully landscaped gardens, with an outdoor shower perfect for post-beach rinses before alfresco dining under the stars. Conveniently located just a short distance from downtown Edgartown's acclaimed restaurants, boutiques, and harbor, this property offers a quintessential Vineyard experience and an established rental history.

16 Mockingbird Drive

This dramatic contemporary styled house lies on 6.5-acres of beautiful pond front land in the exclusive Herring Creek Farm. The home features cathedral ceilings throughout and an open floor plan with large living room, dining room and kitchen, all with clear story light, fireplaces and 20 ft. breakaway Nana walls. The spiral staircase leads from the living room to a large roof deck with expansive views of the South Shore. There are 5 suites all with luxurious bathrooms, closets, and private garden terraces. Additionally, there is an attached carriage house with 3 additional bedrooms, a billiards room and exercise room. The grounds offer a large, stunning pool, a 12 person Jacuzzi, outdoor kitchen, and parking courtyard. There is a high level of finish throughout, a whole house Lutron control system and advanced audio/video. Herring Creek Farm offers direct access to private South Shore beach and over 150 acres of conserved land.

30 Crackatuxet Cove Road

Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

28 Beach Road

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

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.

60 Bartimus Luce 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

East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most importantly, the modern comforts today's lifestyle demands. Set on a generous, level parcel, with an existing seven-bedroom septic system—providing ample opportunity for future expansion and customization. Located in the heart of East Chop, a cherished community known for its neighborly spirit, you're just minutes from the harbor and vibrant downtown Oak Bluffs. A true island compound—rooted in tradition, yet ready for what comes next.

16 Atlantic Avenue

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 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

Island Grove Building Lot - A highly desirable Edgartown location near Morning Glory Farm, the Village, and South Beach. The 1/2 acre parcel is conforming in nature, allowing for maximum development. With approval for 6 bedrooms with sewer tie-in, the opportunities are endless! A great opportunity to get into this terrific community.

58 Marthas Road

Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax overlooking the expansive front lawn. The light-filled, open first floor boasts cathedral ceilings, and hand-cut stone propane fireplace, a kitchen featuring granite countertops, Wolf range, and an undercounter wine cooler. A casual dining area at one end of the kitchen, and inviting living room offer the perfect space to entertain. Rounding out the first floor, the primary bedroom has a large walk-in closet, soaking tub, and bay window looking out over the backyard. The second first floor bedroom is currently being used as a TV room. The second level has two sizable ensuite bedrooms with ample closet space and skylights. Highlights of the home include radiant heat, hardwood floors, firepit, large yard and plenty of room for expansion. Even more opportunity for expansion is found in the partially finished lower level. A future office, media room, or workout area awaits. The two car garage is large and has additional space above offering options for additional guest quarters. Meadow View Farms is quiet and private with walking trails and association tennis. The property has mature plantings and is close to both the bike path and over 200 acres of conservation land with hiking trails. Title 5 inspection passed for a 5 bedroom septic. This home is move in ready and is perfect for year-round living. This home would also make a desirable summer vacation retreat. Most furnishings included.

4 High Meadow Lane

Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers require a deed restriction that prevents the property from ever being used as a bike rental shop. Seize this unique chance to establish your business in a highly visible area.

4 Lagoon Pond Road

This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring ceilings and rich oak floors that flood the space with natural light. Expansive glass walls open up to sweeping oceanviews over Chilmark Pond creating a seamless connection between the indoors and the stunning landscape. The chef's kitchen is a true standout, featuring custom cherry cabinetry, luxurious granite countertops, and top-tier appliances from Sub-Zero, Miele and Wolf. The primary suite offers a private study with a cozy fireplace, two spa-like baths, and a spacious deck with ocean views. Heated floors throughout add an extra layer of comfort. Outdoors, a spacious screened porch and heated infinity pool overlooks the ocean and a beautifully landscaped terrace. The property also boasts a large kitchen garden, fruit trees, and a half-basketball court. A detached three-bay garage and a charming two-bedroom guest cottage provide plenty of room for family and friends. To complete this extraordinary offering, private access to a secluded south shore beach, accessible by boat from Chilmark Pond, ensures a truly exclusive lifestyle.

8 Snail Road

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

501 West Tisbury Road

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

30 Franklin Avenue

Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard. The property feels quintessentially Chilmark with ancient stone walls and mature plantings. The detached guest quarters features a spacious bedroom, full bath, kitchenette eating area, and a garage. Menemsha Hills Reservation is your backyard - 211 acres described by its Trustees as follows: "Menemsha Hills was shaped by thousands of years of glacial advance and retreat. Today an array of mini-environments comprise a rugged, pleasant landscape: low wetlands, woodland groves leading to a hilltop, wind-blasted coastal plains, a rocky ocean edge, and 308-foot Prospect Hill." Not to mention - Menemsha sunsets are a short distance away!

345 North Road

Classic three-bedroom farmhouse offers the perfect blend of island charm and laid-back comfort. Located within walking distance to scenic Sengekontacket Pond, it’s an ideal retreat for nature lovers, kayakers, or anyone looking to enjoy the Vineyard lifestyle.
The home features a welcoming front porch and back deck—perfect spaces to relax, dine, or entertain outdoors. Inside, you'll find a warm and functional layout with three bedrooms, two and a half baths, and a bright, open living space that flows easily from room to room.
A third floor bonus space offers flexible potential—use it as a home office, studio, guest overflow, or playroom. Whether you're looking for a year-round residence, a summer getaway, or a rental investment, this property checks all the boxes.
Enjoy quiet privacy while being just minutes from downtown Edgartown, State Beach, and Oak Bluffs.

71 Sixth Street North

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

90 Seventeenth Street North
Edgartown, Massachusetts

FOR SALE

Here is a chance for you to own a water view property in Edgartown. Property is located just off the Boulevard on a quiet dead end lane.  This property has been in the same family for decades and is now offered for sale. It is a blank canvas for you to create your dream home. Interior has been gutted and is ready for your renovation. The property has a brand new, never used two-bedroom septic system which complies with all applicable laws and regulations and a new electrical panel. Sengekontacket Pond is a short walk away. Downtown Edgartown amenities and beaches are within a short drive. This property is being sold as is and buyers must use their due diligence before making an offer. This property won’t last long.

90 Seventeenth Street North

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS.  THESE LOTS ARE ALREADY SUBDIVIDED.  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

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood.  Open floor plan with high ceilings  that allows a lot of great light into house.  The screened in porch is perfect for family dinners or relaxing.  Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you can enjoy swimming and watching beautiful sunsets.  There is also a 1 car garage with a work space.

100 Gosnolds Way

The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an expansive deck, a pergola with a fireplace, and an elevated gazebo overlooking meticulously manicured grounds. Versatility is at the heart of this unique compound. With three full kitchens, the home easily accommodates use as a spacious single-family residence or as three separate living quarters—ideal for multi-generational living, hosting extended guests, or generating rental income. Additional highlights include a 10-bedroom septic system in place - allowing for future expansion, an oversized three car garage, and solar. Come experience the very best of Island living.

8 Fresh Pond Road

Make your own Chilmark dream come true!
12.6 +/- acres of prime land allows you to create your own family
compound or Island Farm. Enjoy the peacefulness of the Chilmark
with room to expand. Two separate buildable lots provides you unique
options. The Main house has three bedrooms, three bathrooms, two
studies, multiple living spaces and a large three-car garage

88 & 90 Quenames Road

This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle.  The large, flat building envelope offers many siting possibilities and, should you choose, the property is grandfathered for a 1000 sq ft guesthouse, could also support a 900 sq ft ADU and offers room for a barn, pool and/or studio as well. Create an expansive meadow and open gardens or keep a more wooded feel. 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

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location.  As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

7 Overview Lane

Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. 
This five-bedroom, four-bath residence combines historic character with modern comforts. The home features five fireplaces, (one currently hidden behind a plastered wall), a gracious living room, dining room, office, and an inviting kitchen/breakfast room. Additional conveniences include a mudroom, laundry room, central heat and 3 zone air conditioning, and a large screened porch where you’ll find yourself spending more time than anywhere else in the summer time. 
Two of the five bedrooms are on the first floor, including a private ensuite with a full bath. The home is notable for its unusually large and abundant windows, flooding the south-facing interior with natural light. The winding staircase is a sculptural centerpiece that greets you as you enter through the original front door. Renovations include a new roof over the porch, three modernized bathrooms, and updates throughout the first and second floors, all carefully designed to honor the home’s historic charm.
Outside you will find a lawn area and back yard patio that overlook perennial plantings including roses, hydrangeas and dogwood and a white picket fence that creates nice privacy.  Plus there is off-street parking for 2 cars. 
Located just one block from Main Street and two blocks from the Vineyard Haven ferry terminal , this prime location offers easy access to shopping and restaurants and the Tisbury Elementary School.  The town tennis courts are just a half-block away, and its a leisurely stroll to the town beach at Owen Park. 
This is a rare opportunity to own a piece of Vineyard Haven history, where timeless charm meets contemporary comfort.

27 Spring Street

Magical waterfront Quitsa pond cottage with private dock.  This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates the simplistic beauty of this propery. A unique and inspirational built-in art installation by Andy Goldsworthy adorns the northeastern wall of the living room.  A fireplace created with slate roof tiles unlike any other is built into the southwest wall.   Custom Will Parry windows and doors throughout with giant floor to ceiling glass doors that slide wide to join the inside and outside of the home bringing the natural beauty of the area into the house.  Step outside and onto your private dock with power and water, or walk down your boat ramp into the warm waters of the pond for a swim, kayak or paddleboard adventure.  A custom staircase influenced by Frank LLoyd Wright has built-in book cases and metal work by artisan Whit Hanschka which brings you to the upper floor where there are 3 bedrooms and 2 baths. 2 of the bedrooms open out onto a small deck overlooking the pond and all have views of the water. This home is cozy with radiant floor heat under the tile floor

131 State Road

Position your business for success in one of Vineyard Haven’s most visible and accessible locations in Tisbury Marketplace. Unit 30 at 79 Beach Road offers a rare opportunity to own commercial space in the bustling Vineyard Haven business district—just minutes from the ferry terminal and downtown.

This versatile, second-floor unit features 641 square feet of space with a private half bath and stunning views of the Harbor and Lagoon Pond, ideal for a wide range of uses including retail, office, wellness, or professional services. With excellent foot traffic and prominent road frontage, your business will benefit from strong exposure in a high-demand area.

Property highlights include: prime location with steady vehicle and pedestrian traffic; flexible layout adaptable to multiple business types; ample on-site parking; well-maintained complex with professional management; and easy access to ferry, shops, and island amenities.

Whether you're an investor looking for a strong rental property or an owner-user ready to establish a Vineyard presence, this commercial condo delivers unmatched value in a high-visibility setting.

Note: Elevator access available to second floor at the rear of the building.

79 Beach Road 30

This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm.  Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have the best qualities of an island existance, minimize their impact and enjoy the literal fruits of life.  The home has an 81 panel solar production system, granting it producer status and producing a surplus of energy that far surpasses the use. There are fruit orchards around the property that include fig, plum, apple, blueberry, cherry and more. (see addendum) The property achieved status as a Certified Organic Farm (USDA). The fantastic kitchen is designed for the serious chef with a huge 4 x 9 foot center island made of honed granite and a 48 gas range, subzero fridge and bosch dishwasher.  The great room has a floor to ceiling rumford designed stone fireplace with cathedral ceilings, reclaimed antique beams, and a great floor plan that still maintains a sense of intimacy.  Great mudroom with tons of built in that opens into the garage and the laundry room. Generator fed by 500 gallon buried propane tank provides security if weather goes bad. This is a really wonderful house and must be seen.

60 Meetinghouse Road

Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown’s most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the thoughtfully curated interiors and unique floor plan, every detail reflects impeccable craftsmanship and intentional design. The outdoor living space is equally remarkable, featuring a heated saltwater pool, a sunken fire pit, and a show stopping custom glass wall feature. With a strong, proven rental history, this luxurious retreat offers both investment potential and flexibility for today’s discerning buyer. A rare and refreshing opportunity in the heart of Edgartown Village.

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