This split-level home in the highly desirable Dodger’s Hole neighborhood offers a central location with easy access to VTA bus routes, the bike path, all down-island towns and both South Beach and State Beach. The main level features a bright and open living room, dining area, and kitchen designed for comfortable island living. A hallway leads to the primary bedroom with private bath, along with two additional bedrooms that share a full bath. The lower level includes a spacious family room plus additional unfinished space with potential for expanded living quarters, guest accommodations, or a recreation area. Set on a private half-acre lot, the property offers both privacy and ample outdoor space to relax after a day at the beach. Its convenient location and versatile layout make it appealing for both seasonal and year-round living. Property is being sold as is. Estate rules apply. Sale may be subject to probate approval and court confirmation. Please see comments below.

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OPPORTUNITY ABOUNDS: This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer (see notes below) creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of in-town living while building new in a highly desirable neighborhood. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

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Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently located near town amenities, beaches, bike paths, a public fitness facility, veterinary services, shopping, the airport, restaurants, and other island services. Buyer is responsible for conducting all due diligence regarding intended use, permitting requirements, and development of the property.

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This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry way into Edgartown Real Estate today so do not let this opportunity pass you by. A 3rd bedroom maybe an option here and seller will work with you to help with the process.

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CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an enhanced system and proper approvals. Also included in the sale is the owner's share of the Calebs Beach Corporation, giving you access to the sandy beach on the outer harbor.

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A rare opportunity to own 7.7 acres on the beautiful and sought-after island of Chappaquiddick. This wooded parcel offers exceptional privacy, natural contours, and the quiet, untouched landscape that defines Chappy living. Preliminary information suggests there is potential upland area to support the creation of a custom island retreat, with possible capacity for 4–6 bedrooms subject to final engineering, wetlands delineation, septic design, permitting, and all required approvals. A percolation test has been completed with favorable results based on available non-wetland acreage. With significant acreage, exceptional privacy, and the timeless natural landscape of Chappaquiddick, this offering represents a unique opportunity for a buyer willing to complete the necessary permitting, engineering, and due diligence to realize the potential of a remarkable island property.

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Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a private mooring, an extraordinary opportunity to enjoy one of Martha’s Vineyard’s most coveted waterfront locations.

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The North Bluff: A rare opportunity to acquire one of Oak Bluffs’ most iconic properties. Originally built in 1913 and expanded over the years, this distinctive property occupies a prominent setting within the B-2 district, offering a unique range of residential and commercial opportunities. Cherished by the same family for generations, the multi-family property currently comprises four separate living spaces, complemented by substantial garage and storage areas and ample on-site parking. A classic front porch speaks to the property’s early-20th-century character, while expansive decks provide wonderful settings for outdoor entertaining and taking in the surroundings. Beautiful views of Oak Bluffs Harbor and Vineyard Sound can be enjoyed from nearly every room, creating an exceptional sense of place. Whether envisioned as a grand single-family residence, a distinctive commercial venture, or a continuation of its current blend of residential and commercial uses, The North Bluff presents extraordinary potential. With thoughtful planning and the appropriate permitting, this landmark property offers a remarkable opportunity to shape its next chapter.

NEW

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This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, providing valuable, clean, safe storage and operational space, an uncommon amenity for downtown Island properties. The second floor includes two beautifully appointed residential apartments, totaling 6 bedrooms and 3 full bathrooms, ideal for creating additional income potential and operational flexibility. The property has a distinctive commercial history, having served in the 1930's as an A&P grocery store (The Great Atlantic & Pacific Tea Company) and, in recent decades, 99-occupancy restaurants and an upscale retail store. Combining outstanding craftsmanship, state-of-the-art building systems, and a highly desirable high-traffic in-town location, this is a premier mixed-use investment offering with broad appeal to investors, business owners, and developers alike.

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This exceptional mixed-use property occupies a premier location in the heart of Oak Bluffs thriving Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, the building offers a distinctive combination of commercial and residential spaces in one of Martha's Vineyard's most sought-after high-foot-traffic downtown locations. The Union Chapel, across the street, and the Tabernacle, behind the property, host major Island events. Every aspect of the property reflects an outstanding level of craftsmanship and attention to detail. The street level features an expansive commercial space with considerable flexibility for restaurant-bar and/or retail use (for a restauranteur, the kitchen and bar infrastructure are intact and virtually turnkey). The commercial floor includes three handicap-accessible half baths and a convenient and thoughtfully designed rear exterior loading area. The very large newly excavated basement is dry and temperate year-round, providing valuable, clean, safe storage and operational space, an uncommon amenity for downtown Island properties. The second floor includes two beautifully appointed residential apartments, totaling 6 bedrooms and 3 full bathrooms, ideal for creating additional income potential and operational flexibility. The property has a distinctive commercial history, having served in the 1930's as an A&P grocery store (The Great Atlantic & Pacific Tea Company) and, in recent decades, 99-occupancy restaurants and an upscale retail store. Combining outstanding craftsmanship, state-of-the-art building systems, and a highly desirable high-traffic in-town location, this is a premier mixed-use investment offering with broad appeal to investors, business owners, and developers alike.

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Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.

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With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the rear of the property, a private guest house—affectionately known as The Nest—has undergone a similar transformation and offers a private escape. Adjacent to the main home, the charming bunk house completes the ensemble, perfectly complementing this unique and inviting expansive compound. Though the wraparound porch invites you to linger with its endless ocean views, the nearby beaches, boutique shops, acclaimed restaurants, and the contagious energy of Circuit Avenue and the Harbor are all steps away, offering something for everyone to enjoy. For those seeking flexibility, the home’s established rental history further highlights the desirability of both the property and its coveted location. An exciting opportunity to own in one of Oak Bluff's iconic settings!

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