Historical Homes

This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, is flooded with light, open to breezes, and marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with an expansive breakfast island, dining room, and living room with a gas fireplace. Sliders from the living room open to the heated pool and hot tub surrounded by granite pavers. The kitchen shares a view of the pond and Nantucket Sound through the wall of windows and sliders in the dining room out to the deck, a perfect spot for outdoor dining. A wine cooler in the dining room has a pass-through space above it to the adjacent family room. The open floor plan lets the cook connect with family and guests. Beyond the kitchen, accessed through a sliding barn door, is a cleverly placed office with built-in bookshelves and sliders to the deck. A pantry, half bath, laundry, and another mudroom adjacent to the outdoor shower complete the first floor. The views of Sengekontacket and Nantucket Sound become more dramatic on the second and third floors. There are 4 bedrooms on the second floor, including 2 primary suites, all with vaulted shiplap ceilings, as well as a den and a shared bath. The den and one of the suites have private decks that capture the essence of the views. A second sliding barn door opens to the den, creating a private primary wing at the front of the house. An outstanding spiral staircase provides access to the fabulous "Lookout Lounge," where you will enjoy exceptional views inside and outside on 2 decks. The professionally landscaped yard includes a perennial garden, mature trees and shrubs, and a rolling lawn with a fire pit. It's only steps away from the hiking trails of Felix Neck Wildlife Sanctuary, a short trip to the town landing, and an easy drive or bike ride to downtown Edgartown. With ample spaces for relaxation, entertainment, and multiple living areas, this home is the perfect Vineyard experience. First Floor: The mudroom entrance leads directly into the kitchen, which boasts an enormous breakfast island with plenty of room for casual dining. Sliders in the cozy living room with a gas fireplace lead directly to the pool and spa. The dining room, with sliders to the expansive deck, is on the right, with direct access to the family room. Separated by a sliding barn door is an office and a second mudroom that leads to the outdoor shower. A half bath and laundry room complete this floor. Second Floor: Two primary suites on this floor enjoy pleasant views of Sengekontacket and Nantucket Sound. A barn door off one of the suites opens to a den with a private deck overlooking the water. There are two additional bedrooms and a shared full bath on this floor. Third Floor: An impressive spiral staircase leads you to the third level. This space has been ordained the "Lookout Lounge" because of the impressive and expansive views with 2 decks, which both take advantage of the views. A truly spectacular experience!

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

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

Tucked away on the serene shores of Lagoon Pond in Vineyard Haven, this cozy one-bedroom cottage offers the perfect island escape. Located on exclusive Hines Point, the home features stunning water views, direct access to a private beach, and the calming sounds of the tide just steps from your door. Inside, the cottage is thoughtfully designed for comfort and simplicity, with an open living area that captures the natural light and a first floor bedroom retreat. Large windows frame the ever-changing scenes of the lagoon, while a private deck invites you to relax, dine al fresco, or launch a kayak right from your yard. Look no further for your Hines Point oasis or use it as a guest house if you already own on Hines Point — a great location, just minutes from downtown Vineyard Haven shops, restaurants and ferry.

Coming Soon! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to beach, town, bike path, and more, this home sits in a special location. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but it is not on the MACRIS registry. Buyer should research the process for making major renovations. Septic is a cesspool and will need to be upgraded at a Buyer's expense and as part of the overall plan for the property. Being sold ''as is''. Interior photos to be added by 9/23.

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.

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.

Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to shops, restaurants, beaches, and ferries. . The commercial zoned land has been approved for several different situations from housing to store fronts. Come take a look at all this property has to offer.

Circuit Ave. Commercial Property Build your own commercial building of your dreams on the last B1 undeveloped commercial property on Circuit Avenue's main strip. The commercial land had previously approved development plans including mixed use with commercial store front and apartments or condos above. Located on the corner of Circuit Ave and Massasoit Ave. this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms. With a large warp around porch the spacious home has a lot to offer from Employee housing to a bed and breakfast. The commercial zoned land has been approved for several different situations from housing to store fronts. Easy to show.

Unlock the potential of this unique property! Sitting on a spacious 1.83-acre lot, this property offers town water and endless possibilities for builders and investors ready for a project. The existing house needs to be raised and is being sold strictly as-is, presenting a rare opportunity to create your vision from the ground up. Enjoy the privacy and space of nearly two acres, all while being close to local amenities, major routes, and community resources. Bring your plans, your contractor, and your imagination — this is your chance to make something truly special. House is serviced by a cesspool. Important: Property will not qualify for traditional financing. Buyer to do their own due diligence. Schedule your showing today and see the potential for yourself!

Highest & Best Due Tuesday 12noon!! Fall in Love with this Adorable Somerset Cottage! Imagine the peaceful start to each day on the inviting front porch of this charming 2-bed, 1 bath cottage, perfectly situated in a quiet Somerset neighborhood. Step inside and feel the cozy atmosphere, enhanced by a wood-burning fireplace that invites relaxation. A practical detached garage provides convenient parking or extra storage. The large basement offers valuable space for organized storage or to indulge in your hobbies. The spacious, fenced-in backyard is a true extension of the living space, offering a secure and tranquil environment for children and pets to play. This delightful cottage also boasts the convenience of being located close to major highways for easy commuting, a variety of shopping options to meet your needs, and lovely local parks for outdoor recreation, all within the welcoming town of Somerset. Don't miss the opportunity to make this charming cottage your own!

This classic cape-style home is a true piece of Plympton history with charming details including Kings Pine Floors, exposed beams, large fireplace with hearth, and shiplap wainscoting. This home features a first-floor master bedroom and full bath. Two additional rooms are on the second floor with built-in dressers in the eaves and a large shared closet between them. Step outside to your very own oasis, complete with horse barns, enclosed animal pen, wildflowers, fruit trees, and incredible views of the Winnetuxet River! Close proximity to schools, shopping, restaurants and major routes. If you are looking for a one-of-a-kind home, you will truly enjoy this rare offering. MORE PICTURES COMING THIS WEEK!

Classic Hip-roof Colonial style home situated on 3/4 acre lot and abutting the 12th hole on Thorny Lea Golf Course. The setting of this house is a one of a kind in the City of Brockton. Enter the front door to a large open foyer with a spectacular circular stairway to the second floor. The first floor has a large front to back living room with fireplace, a light and bright sunroom room off the living room. The dining room is off the foyer and will seat all your family and more. There is family room/study off the foyer that also enters the kitchen area. The kitchen has a large working area for the chef of the house and a large dining area for your every day dining. Continue from the kitchen to a full bath with shower, laundry room and access to the garage and patio area. The second floor has a large main bedroom suite with 2 walk-in closets and full bath. There are 3 additional bedrooms and another full family bathroom. The back yard setting is out of Home and garden

Fantastic investment opportunity awaits with this beautifully updated three-family home, ideally located on a quiet dead-end street! Each unit has been thoughtfully refreshed, featuring modern touches. Offering spacious living areas, and a quaint yard, this property offers hassle-free ownership and steady income potential. Convenient to local amenities and commuter routes this home is a perfect investment opportunity! Don’t miss out on this turnkey multi-family gem!

Discover your dream coastal estate on a stunning peninsula, offering breathtaking sunrise and sunset views. This rare estate includes four buildings, perfect for creating a family compound, boutique bed-and-breakfast, or vacation rentals. The main home features 4 bedrooms, 3 baths, and potential for additional space in the attic. The updated pool/guest house and barn-style building with an apartment and workshop add to the charm. Recent improvements include new roofs on all buildings, fresh exterior paint, two new heating systems, and a new pool liner for the in-ground pool. New septic system for the back house to be installed prior to closing, passing Title V for front septic. This is your chance to own a breathtaking coastal retreat with endless opportunities!

Welcome to your private retreat in East Fairhaven! Set on 6.16 serene acres, this charming 2-bed, 1-bath home offers endless possibilities. Sunlight pours through picture windows, highlighting a cozy stone fireplace and open living spaces. Enjoy peaceful mornings on the covered porch or relax on the well-sized deck overlooking a tranquil duck pond surrounded by mature trees and vibrant flowers. Expansion potential or an ADU opportunity makes this property even more versatile. Nature, privacy, and possibility await — a rare find close to town amenities!

Discover unparalleled coastal elegance with these remarkable front residences, perfectly positioned on a dramatic peninsula. The main home features four expansive bedrooms, 2.5 modern baths, and untapped attic potential, all set against captivating sunrise and sunset panoramas. Recent upgrades include brand-new roofing, pristine exterior finishes, new heating systems, and an updated in-ground pool with new liner that redefines outdoor leisure. Enhancing this exclusive offering is a 750 sq.ft. pool/guest house and a charming barn-style structure that houses a 975 sq.ft. apartment above an oversized garage, complete with a spacious workshop. A shared driveway easement ensures effortless access, making this section of the estate ideal for a family compound or a serene coastal haven. This property is also available as a package—see MLS 73301880 for details.

Discover your dream coastal estate on a stunning peninsula, offering breathtaking sunrise and sunset views. This rare estate includes four buildings, perfect for creating a family compound, boutique bed-and-breakfast, or vacation rentals. The main home features 4 bedrooms, 3 baths, and potential for additional space in the attic. The updated pool/guest house and barn-style building with an apartment and workshop add to the charm. Recent improvements include new roofs on all buildings, fresh exterior paint, two new heating systems, and a new pool liner for the in-ground pool. New septic system for the back house to be installed prior to closing, passing Title V for front septic. This is your chance to own a breathtaking coastal retreat with endless opportunities!

Welcome home to this beautifully updated 4-bedroom, 2 bath colonial conveniently located near vibrant downtown Middleboro! Easy commuting with quick access to commuter rail and major routes RTE 44, 495, and 18. Enjoy gatherings in the spacious, modern kitchen featuring an inviting open floor plan. Cozy up by the fireplace or utilize the convenient main-floor office space. Relax on the charming covered porch overlooking a generous yard perfect for entertaining, play, or relaxation. Additionally a new water line is being installed. This home seamlessly blends timeless colonial charm with contemporary comforts—a must-see!

Charming Farmhouse with Victorian Flair on 1.97 Acres! Welcome to 99 Heart St., Taunton—a picturesque farmhouse with a touch of Victorian charm, known as the “Gingerbread House” during the holidays for its festive Christmas lights! Built in 1900, this 1,510sq.ft. home sits on a sprawling 1.97-acre lot, offering space, privacy, and timeless character. Inside, you’ll find 3 bedrooms, 1.5 baths, and warm, inviting spaces perfect for cozy living.A standout feature of this property is the massive detached 50’ x 30’ garage, ideal for car enthusiasts, hobbyists, or extra storage. Enjoy the charm of an older-style farmhouse with modern conveniences, all in a desirable Taunton location.Don’t miss the opportunity to own this truly special home—schedule your private showing today!