164 properties for sale in East Chop

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 privat

The Doll House is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering exceptional opportunities for swimming, kayaking, and paddleboarding directly from your backyard. The main residence features a welcoming sun porch, an inviting living room anchored by a stone fireplace, and a light-filled primary bedroom with tranquil water views. The updated kitchen and adjoining dining area showcase beautiful brick floors and a built-in window seat. French doors open from the kitchen to a spacious lawn designed for outdoor entertaining, complete with a charming former boathouse reimagined as a unique dining pavilion. A strikin

The Doll House is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and impeccably maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush landscaping and beautiful hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering exceptional opportunities for swimming, kayaking, and paddleboarding directly from your backyard. The main residence features a welcoming sun porch, an inviting living room anchored by a stone fireplace, and a light-filled primary bedroom with tranquil water views. The updated kitchen and adjoining dining area showcase beautiful brick floors and a built-in window seat. French doors open from the kitchen to a spacious lawn designed for outdoor entertaining, complete with a charming former boathouse reimagined as a unique dining pavilion. A strikin

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 privat

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Here is your opportunity to own a charming Cape close to beaches, the bike path and plenty of dining and shopping options. This home features wide plank wood floors on the first level and a full unfinished basement for storage and potential additional living space. Second level has two spacious bedrooms with cathedral ceilings and ample natural light. Rooftop widow's walk provides panoramic views. 3 bedroom septic has passed Title 5 inspection. This home is being offered as-is

Set within the historic fabric of Edgartown Village, 14 Thayer Street is a property of uncommon scale and quiet distinction. Occupying a 0.62-acre parcel, rare for this in-town setting, the grounds offer a sense of space and privacy just moments from the harbor and village center. The residence is attributed to Frederick Baylies Jr the builder of the Whaling Church, and reflects the enduring architectural traditions that define Edgartown. With five bedrooms and five baths across more than 3,100 square feet, the home is both comfortable and unpretentious, suited to long summer stays and informal gatherings. Mature landscaping and open lawn frame the house, lending a sense of seclusion that is increasingly difficult to find within the village. Properties of this scale and provenance seldom come to market, offering a measured opportunity to steward a piece of Edgartown's architectural legacy

Located in Falmouth Heights, less than two-tenths of a mile from Falmouth Heights Beach, this well-built three-bedroom home offers an exceptional opportunity in one of Falmouth's most desirable seaside neighborhoods. Set on a generous corner lot outside the flood zone, the property offers added space and privacy while remaining close to the beach, Falmouth Harbor, and downtown Falmouth. Built in 1983, the home offers the advantages of more modern construction, including a poured concrete foundation and full basement. The flexible floor plan features two bedrooms on the first floor and a third bedroom upstairs. Recent improvements include a newer roof and fresh interior paint throughout, creating a clean canvas for new owners to make it their own. The spacious yard offers room for outdoor living, gardening, and recreation. Enjoy easy access to seaside dining, the Heights ballfield, and the summer traditions that make Falmouth Heights so special. Whether it's a morning walk to the beach,

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, dishwasher, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha's Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef's kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat

This year-round home, situated less than half a mile from Lambert's Cove Beach, boasts fine craftsmanship and character in a peaceful, wooded environment. Inside, the open living room features wide plank floors, cathedral ceilings with beams, and a central brick fireplace that connects seamlessly to the updated kitchen

Fantastic location near Falmouth Heights Beach, Falmouth Harbor, Island Queen, Main Street restaurants and shopping. 3 bedrooms and 2 full baths. Living room, family room, kitchen with dining area. Full bath on both first and second floor. Roof 2022. Hot water tank 2024. Freshly painted interior. This location is ideal for ease of getting on and off the Cape and then enjoying all the things that make Falmouth such a special Cape Cod town

This classic Edgartown Colonial is ideally situated in the heart of the village, just a short stroll from Fuller Street Beach, as well as Edgartown's acclaimed restaurants, boutiques, and harbor. Designed for comfortable coastal living and effortless entertaining, the open-concept floor plan flows seamlessly throughout the home. Offering 10 well-appointed rooms, the residence features six bedrooms, four full bathrooms, and two powder rooms. The gourmet kitchen opens to the spacious living and dining areas, creating an inviting gathering space that extends through French doors to a generous bluestone patio. The beautifully landscaped yard is highlighted by a private, thoughtfully sited swimming pool, providing a peaceful outdoor retreat perfect for relaxing or entertaining

ENJOY THE SEA BREEZES AND SPECTACULAR VIEWS. Wake up to the ever-changing beauty of Vineyard Sound, watch the ferries cross in the distance toward Woods Hole, and end the day with sunset views stretching down the Lagoon. Designed to celebrate its extraordinary setting, this 4-bedroom, 2.5-bath home offers a rare lifestyle defined by light, water, and effortless indoor-outdoor living. With commanding views from nearly every room, the home invites you to slow down and take in the scenery from every angle. Two levels of covered decks overlook Vineyard Sound, while two additional levels of decks face the Lagoon, creating multiple outdoor spaces for morning coffee, afternoon reading, summer entertaining, or quiet evenings under the stars. The first level offers three comfortable bedrooms, a spacious family room, a full bath with laundry, and generous storage - ideal for hosting family and friends after a day at the beach, on the boat, or exploring the Island. Upstairs, the sun-filled open l

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilit

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha's Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef's kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 94 at 131 N. Water Street is a beautifully appointed 730+/- sq. ft second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, dishwasher, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

New Price! Nestled in the serene Lower Davisville neighborhood of East Falmouth, this waterfront gem offers 1.8 acres of coastal bliss with direct frontage on Bourne's Pond, a saltwater inlet flowing to Vineyard Sound. Perfect for kayaking, small craft sailing, or simply soaking in the tranquil views. The home boasts one level living in the main residence with 3 spacious bedrooms, 2 full baths, and separate laundry, with sunlit interiors that seamlessly connect to the stunning natural surroundings. Adding to its allure, the property includes a remarkable detached two-story art studio, complete with an open living and dining area, full bath, and lofted bedroom. Whether you envision it as a creative workspace, a private guesthouse, or even a rental opportunity, it's a unique feature that sets this property apart. Less than one mile from Menauhant Beach and Green Pond Yacht Club, this home offers peaceful seclusion with easy access to East Falmouth's coastal attractions

LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061+/- sq. ft second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities and services. Coastal-inspired interiors feature high ceilings, abundant natural light, a propane fireplace, and an inviting open living area. The well-equipped kitchenette includes a cooktop, dishwasher, microwave, and refrigerator/freezer. Owners enjoy concierge services, daily housekeeping, a fitness center, heated salt-water pool, and gas fire pits.This landmark property offers a rare opportunity to enjoy the Vineyard lifestyle with convenience and peace of mind. Unit 94 combines convenience and a sought-after Edgartown address making it an ideal retreat for those seeking an extraordinary living experience

New Price! Nestled in the serene Lower Davisville neighborhood of East Falmouth, this waterfront gem offers 1.8 acres of coastal bliss with direct frontage on Bourne's Pond, a saltwater inlet flowing to Vineyard Sound. Perfect for kayaking, small craft sailing, or simply soaking in the tranquil views. The home boasts one level living in the main residence with 3 spacious bedrooms, 2 full baths, and separate laundry, with sunlit interiors that seamlessly connect to the stunning natural surroundings. Adding to its allure, the property includes a remarkable detached two-story art studio, complete with an open living and dining area, full bath, and lofted bedroom. Whether you envision it as a creative workspace, a private guesthouse, or even a rental opportunity, it's a unique feature that sets this property apart. Less than one mile from Menauhant Beach and Green Pond Yacht Club, this home offers peaceful seclusion with easy access to East Falmouth's coastal attractions

Easy Edgartown living awaits in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout that works beautifully for everyday life, entertaining, or relaxed seasonal stays. The private primary suite includes its own bath, while two additional bedrooms share a full bathroom, creating a practical and comfortable floor plan. A full basement provides excellent storage and added flexibility, with room for bikes, beach gear, tools, or future possibilities. Step outside to enjoy the deck, fenced yard, and quintessential outdoor shower - the perfect Vineyard touch after a day at the beach. With the bus stop conveniently located at the end of the street, getting around the island is simple and stress-free. Just minutes from downtown Edgartown, bike paths, restaurants, shops, and some of the island's most loved bea

Less than 0.5 mile to Falmouth Heights Beach-this is the kind of Falmouth Heights location that rarely becomes available and doesn't last. Sidewalk-lined streets lead to the shoreline, with Falmouth Harbor, the Island Queen ferry, and Main Street just 1.5 miles away. Beach days, boat rides, dinner out, and morning coffee-everything that defines summer on Cape Cod is right here, without compromise. Set on a.24-acre lot, this 3-bedroom, 1.5-bath Cape offers ~1,404 sq ft with a flexible layout, including a main-level bedroom and bath that adds everyday convenience. Beautifully maintained with timeless charm, the home offers immediate comfort along with opportunity for future customization. Out back, the fenced yard is designed for summer living with an outdoor shower, retractable awning for shade, and a firepit area perfect for easy evenings after the beach. A proven coastal location with strong rental appeal, immediate enjoyment, and long-term upside-opportunities like this don't wait