Nestled on a private 1.7-acre parcel in the peaceful Bold Meadow neighborhood, this classic expanded Cape offers a perfect blend of comfort, space, and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from all that Edgartown has to offer. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a wood-burning fireplace and a separate TV/family room. The well-appointed kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar for casual dining. An eat-in area opens through sliding glass doors to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, two guest bedrooms share a full bath, while a loft above the two-car garage provides flexible bonus space, currently used as an artist’s studio. The home is served by a four-bedroom septic system, with the potential to expand to six bedrooms subject to Board of Health approval and installation of an enhanced system. With easy access to nearby bike paths, pristine beaches, and the shops and restaurants of downtown Edgartown, this property offers an exceptional combination of location, privacy, and lifestyle.

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A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beach, Nantucket Sound and beyond. Set along the Boulevard, behind a traditional white picket fence, this .66 acre property features two side-by-side cottages dating back to the 1940s and captures the relaxed character of an earlier Vineyard. The larger cottage is a quintessential Vineyard retreat with beautiful direct waterviews from the Main living areas, dining area and porch. Upstairs, a sitting area and small upper deck provide exceptional views across Sengekontacket Pond to State Beach extending out towards Cape Cod. The porch and the spacious lush side yard with lawn and lovely plantings, offer an inviting setting for morning coffee, summer dinners, entertaining, or simply enjoying the changing light and activity on the water. The larger cottage has an established rental history. An attractive option for seasonal rental income. The second smaller cottage offer the opportunity for a new owner to renovate and make the space their own as additional living space, a guest cottage or studio, subject to applicable approvals. Another compelling option is to explore removing the cottages and combining the existing square footage together with a percentage of additional square footage as allowed, to create one larger residence to take full advantage of this extraordinary waterfront setting. Any renovations, expansion or redevelopment would be subject to all applicable approvals and zoning regulations. Additionally, just a stone's throw away, the nearby boat landing provides convenient access to the pond, with openings into the Nantucket Sound, for launching kayaks, paddleboards and trailered boats. putting one of the Vineyard's most beautiful waterways practically at your doorstep. With two cottages, acreage, established rental history, convenient boating access and remarkable views.#49 The Boulevard offers a special opportunity to enjoy a classic Vineyard property today while imagining and planning its possibilities for the future.

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Just a block off Main St, Winter Street grew alongside Edgartown's 19th Century maritime and whaling boom. In the mid 2010's local business owners began transforming the corridor, and affectionally dubbed Winter Street the "Left Bank" of Edgartown in comparison to Paris's famous boutique shopping district. This retail condo is one of the the prettiest shops in Edgartown with 2000+ square footage. It has a front row on Winter Street with wonderful display windows that attract attention from auto passengers and pedestrians alike. The space has been extensively renovated with built-ins which help display myriad types of merchandise from clothing and accessories to furniture, books, and house wares. In addition to the retail space, the upstairs offers a full bathroom and office, while the full dry basement is ideal for storing inventory. This is a wonderful opportunity to own a retail space in downtown Edgartown, which is widely considered highly prestigious and places you among the most exclusive markets on the East Coast. This beautiful store is available to rent starting in January 2027!

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Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy access to town and the beach. Neighboring Wilson's Landing opens the door to the Edgartown Great Pond, where kayaking, paddleboarding, and quiet days on the water await. With 8 bedrooms possible and the option to add a guest house, the potential here is considerable. This is one of two parcels for sale.

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Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore. Neighboring Wilson’s Landing provides water access to the Edgartown Great Pond for kayaking, paddleboarding, and other activities. With 8 bedrooms possible and the potential to build a guest house, the development options here are many. Whether you envision a family compound, a retreat with room for extended family and friends, or a legacy property designed to be enjoyed for generations, this land provides the canvas. This is one of two parcels for sale.

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Coastal Luxury Meets Versatility in Edgartown Welcome to a rare opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a sprawling one-acre plot with a stunning detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, sun-drenched living room featuring a wall of glass sliders that erase the boundary between indoor and outdoor living. The gourmet kitchen is a chef’s dream, boasting premium Bosch appliances, a large quartz-topped island with casual seating for four, and a sleek, hidden microwave drawer, all perfectly arranged for entertaining.  The first floor hosts a serene primary suite with a luxurious private bath. Upstairs, you’ll find a cozy second living room and two spacious guest suites, each with private baths. The property includes a 900 sq ft detached accessory dwelling, complete with full kitchen, bath, and bedroom. With one acre of land, this property is poised for a future pool or private oasis. Ready for your 2026 occupancy!  Note: This property is subject to M.G.L. Chapter 40A Section 6 of the Affordable Homes Act: Single-family residence not to exceed 1,850 sq ft of heated living area, min. 3 bedrooms, no short-term rentals.

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LUXURIOUS LIVING AWAITS AT THE ICONIC HARBOR VIEW HOTEL CAPTAIN COLLINS COTTAGE, Unit 22 at 131 N Water Street in Edgartown, a 960-square-foot, two-bedroom, two-bath, second floor condominium that offers a refined island living experience at the crown jewel of Martha’s Vineyard. The legendary Harbor View Hotel has been a mainstay spanning over 130 years. Built in 1891 and after a restoration in 2018, this picturesque and sophisticated resort condo is offering the opportunity of a fully managed residence, providing the splendor of Vineyard home ownership without the worry of maintenance and property management. Thoughtfully designed with coastal-inspired interiors, high ceilings, abundant natural light, and a propane fireplace. The open living space is both elegant and inviting and the well-equipped kitchenette features a microwave, and refrigerator/freezer. Both bedrooms are well proportioned, and the two full bathrooms are designed for everyday ease. An in-unit washer and dryer add to the practicality of the home and an outdoor shower enhances the coastal lifestyle. The building features an elevator for effortless entry to your unit. Owners enjoy access to the Harbor View Hotel’s premier amenities, including concierge services, daily housekeeping, a fitness center, heated salt-water pool, gas fire pits, and exceptional hospitality. This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with luxury, convenience, and peace of mind. Captain Collins Cottage, Unit 22 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience.

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Located on a quiet street just moments from Edgartown Village, this versatile compound offers a rare combination of privacy, flexibility, and proximity to some of the Island’s most treasured outdoor amenities. Set on over a half-acre, the property features a main residence and a detached guest house, thoughtfully positioned with separate driveways and a natural buffer of mature trees. The main house offers a comfortable and inviting interior, highlighted by a bay window and a spacious open kitchen and dining area with granite countertops, custom cabinetry, and direct access to the deck. A sunken living room offers separation while maintaining an open flow. The main level includes a primary bedroom and an additional bedroom, while the second floor offers a third bedroom, a full bathroom, and flexible living space. The finished lower level offers approximately 790 sq ft of additional finished space, including a recreation area, den, and full bathroom, along with approximately 525 sq ft of unfinished storage. Outdoor living is equally inviting, with a deck off the kitchen leading to the heated pool and patio. The space includes a pool house with half bath, an outdoor shower, and ample room for dining and lounging, surrounded by hydrangeas. There is ample yard space behind both the main house and guest house, ideal for games, outdoor entertaining, or simply enjoying the privacy and natural setting. The guest house, built in 2011, is thoughtfully separated from the main house by its own private driveway and mature landscape screening. It features a spacious living area, a main-level bedroom, and additional finished space upstairs, along with full bathrooms on both levels. There is also a half bath with laundry, a one-car garage, and a full basement. At the end of 21st Street you’ll find direct access to over 150 acres within the Caroline Tuthill Preserve, as well as the Boulevard landing on Sengekontacket Pond — perfect for kayaking, paddle boarding, or boating. Edgartown Village is approximately 1.5 miles away. A unique opportunity with an established rental history — details upon request. Furniture available for separate purchase.

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Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round living. At the heart of the home is a beautifully remodeled kitchen, completed in 2023 and designed to be part of daily life rather than separate from it. From here, the home unfolds into a spacious living room warmed by a propane fireplace, a formal dining room and a separate sitting room—giving family and guests the increasingly rare luxury of having both places to come together and places to retreat. Three large bedrooms provide comfortable private quarters, while an open loft creates another flexible destination for working, reading, watching a movie or simply escaping the activity downstairs. Below, a substantial unfinished basement with high ceilings and both interior and exterior access provides exceptional storage and flexibility for the future. Summer living extends naturally outdoors. A generous back deck overlooks the wooded acre-plus setting, offering a private place for morning coffee, long dinners and evenings under the Vineyard sky. And after a day spent at the beach, there is perhaps no more quintessentially Island pleasure than coming home to an outdoor shower. Beyond the property, Woodhaven offers something increasingly difficult to find: a neighborhood setting surrounded by nature with access to trails connecting the Manuel F. Correllus State Forest - opening miles of the Island for walking, running and biking. Private without being isolated, spacious without feeling overwhelming, and thoughtfully updated where it matters most, 10 Woodhaven Drive offers a relaxed approach to Edgartown living—and a home designed to be enjoyed well beyond the summer season.

PC

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Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

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WATERVIEWS of Sengenotacket when you pull out of the driveway at 77 SIXTH STREET NORTH, EDGARTOWN. NEW CONSTRUCTION, with an anticipated completion date in MARCH of 2027; just in time to bring in the 2027 SPRING/SUMMER SEASON! The first floor entry offers an inviting two story foyer which opens to the living room which has a gas fireplace and wall of glass slider doors. Flowing from the living room is the open kitchen area which offers an island with seating for four. The kitchen sports Bosch appliances, an island with a built in drawer microwave, quartz countertops and an easy layout for cooking and entertaining. The kitchen then opens to a separate dining room. A half bath off the living room and a first floor primary bedroom with a luxurious private bath completes the first floor. The second floor offers a second living room and two guest bedrooms, each with their own bath. The plot is large enough to support a future detached garage. Come and enjoy! The pictures are of a similar home that was built.

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Located on Upper Main Street in Edgartown’s BII zoning district, this versatile property is currently home to Lucky Hank’s restaurant. Set on a desirable lot with a large private parking area, and in a coveted high-visibility location. The building offers a turnkey restaurant space and thriving business complete with a fully equipped commercial kitchen on the first floor. Upstairs, you’ll find one bedroom with an ensuite full bathroom, currently being used as the office. There is also an additional room being used for restaurant storage. With the flexibility to convert the property back to residential use, if desired, this is a rare opportunity in a prime location that should not be overlooked! Showings are on Mondays when the restaurant is closed.

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