Historical Homes

Discover these historic homes, each with a unique story waiting for you to make it your own. Explore these timeless treasures and discover a home that connects you to the past.

$1,599,000

3 Bed

2 Bath

North Chatham

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Sited in one of North Chatham's most sought-after areas on a 1/2 acre lot, this recently renovated custom home sets the bar on luxurious living. This 3 BR, 2 BA home is rich in architectural design with crown molding, shiplap ceilings and walls, and gorgeous 4-inch white oak floors throughout. This open and circular one-floor living space has an expansive feel with a gas fireplace including chefs kitchen with large quartz center island, top-of-the-line appliances, full pantry with wine shelves and custom cabinets with interior lighting. Office with laundry room hook-up overlooking the back deck can accommodate a twin bed or crib. French doors open onto a private wrap-around deck that runs the length of the house with an outdoor shower that overlooks a huge flat backyard with room for a pool, fire pit, and lawn games. There is also a shed for storage. Professional landscaping includes a new well and irrigation system, pea stone driveway for 6 cars, blue granite walkways, alluring hydrangeas and tall privet hedge.Walk to Chatham Bars Inn, fish pier, downtown Chatham and neighborhood beaches. This is a gem of a house that won't last! Please verify all information contained herein.

$3,700,000

6 Bed

3 Bath

Oak Bluffs

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This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to shops, restaurants, beaches, and ferries. Come take a look at all this property has to offer.

$1,200,000

2 Bed

1 Bath

Provincetown

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Smartly renovated and beautifully decorated top floor two-bedroom condo in an ideal near West End location. An outside stairway with a comfortable rise and run brings you up to a private deck and the main entrance. The sunlit great room features remote control skylights with electric shades, a well-designed kitchen, and a comfortable dining and living area. Both bedrooms accommodate queen-size beds. Small format subway tiles in white and vintage green set a relaxing tone in the spacious bathroom with built in storage and and stack laundry in the closet. The exterior of the building is equally well maintained with newer siding, decks, railings and lighting. Split system AC and heat, baseboard electric, pet-friendly, and rentals allowed. Includes one outside parking space and the right of first refusal to purchase garage Unit #4 for $249,000 (MLS#22405883)

$1,900,000

3 Bed

2 Bath

Oak Bluffs

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Downtown Oak Bluffs- TWO Penthouse Condominiums being sold together. Located in the heart of Oak Bluffs on Circuit Ave. with easy access to beaches, shops, and restaurants. These two units with a combined 1787 square feet of interior space come and an amazing rooftop deck were you can see panoramic views of the Vineyard Sound and Oak Bluffs harbor. This large deck with multiple seating areas and a is an ideal place to gather with family and friends and relax above it all. As you enter the first unit you'll notice the beautiful hardwood floors and custom-made cabinetry throughout, with a kitchen and breakfast bar leading into a dining area. A Ship's ladder takes you the the rooftop deck which gives you a birds eye view of downtown Oak Bluffs and the surrounding water. The spacious living room is a great place to gather with an electric fireplace for cozy nights. Off the living area is a guest bedroom. The primary bedroom is large and inviting with plenty of closet space. A tiled bathroom has a glass enclosed shower surround. --- The second unit has the same hardwood floors, with the kitchen and dining area are divided with custom cabinetry. An open staircase leads to the rooftop deck creating a nook with storage and a daybed on the other side. Take a step down to the comfortable living area. The spacious bedroom has an alcove with pull down skylight, ideal for an exercise area or office. A tiled bathroom with full tub and shower can be entered off the hall or bedroom. Both of the units have their own entrances to the amazing rooftop deck exclusively for their use only. A connecting door in the living rooms between the units can be opened up or lock depending on your desired use. A separate Laundry room is available on the second floor.

$2,795,000

3 Bed

2 Bath

Brewster

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Bayfront Brewster- Located in one of Brewsters premier bay locations. The residence offers direct access to your own beach. this classic Cape Cottage style beach house has been updated, but still has that classic Cape Cod beach house charm of yesteryear. The residence has 3 bedrooms, 2 updated baths, ductless heat and ac, backup generator, detached shed for all those beach toys and more!

$12,000,000

8 Bed

7 Bath

Hyannis Port

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This quintessential Cape Cod home has spectacular views of Nantucket Sound and Hyannis Port Harbor..It is a true landmark property and has been lovingly cared for. Step inside the enclosed front porch overlooking the sprawling lawn perfect for summer entertaining.The spacious living room has a wood burning fireplace and French doors leading to the pool and garden. The gracious dining room with fireplace can host a large holiday gathering with views of the harbor. The entertainment size kitchen is well equipped with stainless subzero fridges, a wine cooler, oversized wolf range and ovens, a coffee bar, and counter height center island. The second story has a primary suite with an ensuite bath and sitting area with water views. Head upstairs and one feels they are stepping on to a custom yacht with the beautiful wood details in the upstairs entertainment room with a bar and half bath.There are stairs that lead up to a large widows walk so one can watch the boats come and go.The three car detached garage has a two bedroom guest house ensuring ample space of family and friends.Located in the heart of the village, this spectacular residence is within the Hyannis Port Civic Association.

$364,900

3 Bed

2 Bath

New Bedford

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Welcome to this delightful three bedroom one and a half bathroom home, offering an eatin kitchen with a large pantry that keeps everything within reach. The Dining room flows nicely into the living room great for entertaining, this home also has a nice bonus space that would be great for a small office or sitting area. The three bedrooms are all very spacious. The back yard is designed for relaxation with an above ground pool , patio area and a shed. The yard also has a sprinkler system and the home has solar panels to reduce energy cost. Roof aprox 10 yr old, furnance 2 yrs old

$429,000

3 Bed

2 Bath

Wareham

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Discover this delightful single-family home just minutes from Onset Beach, featuring a spacious floor plan that invites abundant natural light through its numerous windows. This charming residence boasts three bedrooms, including a first-floor option for easy accessibility, and one and a half baths, offering both comfort and convenience. The generous living room is perfect for relaxation, while the modern kitchen, equipped with ample cabinetry and access to the backyard, flows seamlessly into a formal dining area. The second floor hosts two additional bedrooms, each providing ample closet space and stunning views. Outside, a large yard awaits, ideal for entertaining, complete with a wooden deck, fire pit, fenced yard, and a convenient storage shed. With ample parking for six vehicles, this home also has great potential as a beach or seasonal rental, making it a perfect coastal retreat for those looking to embrace beachside living!

$699,000

3 Bed

2 Bath

Harwich

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Welcome to 589 Depot Street. This property is .89 acres and is convenient to the highway, shopping, conservation areas, the Rail Trail, and is centrally located to allow for easy travel to the North or South side of the Cape. This three bedroom home features a sprawling floorplan, including a first-floor guest room, a recently renovated full first-floor bathroom, and a large great room perfect for entertaining. A large, detached two-car garage with loft provides ample storage separate of the house, and is another highlight of this property. Listed as a three-bedroom home with the town, the septic system has capacity for a fourth bedroom, should renovations or an addition be contemplated. This property is full of potential, and is ready to welcome its next owner.

$950,000

4 Bed

2 Bath

Falmouth

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Charming 1920s Cape-style home in a desirable saltwater community of Falmouth Heights with peek water views from multiple rooms. This 4-bedroom, 1.5-bath residence spans 1616+/- sq ft, featuring original wood floors, a walk-in pantry, and a kitchen with custom, solid cabinetry. The cozy enclosed heated porch and level yard with a shed offer inviting outdoor spaces. Recent updates include a new first-floor half bath (2018) and a CertainTeed 40-year roof (2020). Ample parking with two paved driveways. Enjoy the coastal lifestyle near Central Park, Falmouth Harbor, Yacht Club, Island Queen, local beaches, Black Dog Cafe and more. Reasonable estimate in hand for a four bedroom septic. Currently a cesspool. Not in NSA. Buyers to verify all information contained herein.

$599,000

2 Bed

1 Bath

East Falmouth

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This charming, recently renovated cottage sits on over an acre of land in the heart of Waquoit Village Historic District. Inside, you'll find a cozy living room with a wood-burning fireplace, an updated kitchen and bathroom with tile flooring, and inviting bedrooms designed for relaxation. The spacious yard offers plenty of room to expand or rebuild, with access from Parsons Lane and bordering Barrows Road. Currently tenant-occupied, this property presents an excellent opportunity for either investment or personal use. Additionally, it features a screened-in ''Teahouse'' with an incredible brick wood-burning fireplace, perfect for entertaining or quiet evenings. Situated in a desirable neighborhood, this home provides convenient access to all that Cape Cod has to offer.

$2,349,999

7 Bed

9 Bath

Fairhaven

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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!

$2,349,999

7 Bed

9 Bath

Fairhaven

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$2,000,000

4 Bed

4 Bath

Oak Bluffs

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These twin houses built in 1909 in the historic subdivision of East Chop Highlands offer most of the modern conveniences of today with the old world charm and decorative craftmanship style. Both houses are separately deeded so that they could be owned separately or together. These houses are fully winterized and have been occupied for the past 30 years. Each house has 2 bedrooms with bathrooms en suite. An open floor plan with a kitchen, dining area, and living room #12 has a bonus room presently used as an office. Both houses have 2 heating systems, both forced hot-air central heat, and air pump heating and air conditioning for energy efficiency. One is heated with oil and the other with propane. The yards are complete apple trees, cherry trees, grapevines and more. Each home has it's own back patio with a private seating area and outdoor shower.

$2,100,000

13 Bed

6 Bath

Provincetown

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Nestled away along one of the enchanting footpaths of Provincetown's historic Commercial Street, The Captain's House is a remarkable opportunity awaiting its next chapter. This stately Federal Style home has been a cherished bed and breakfast for generations, embodying the very essence of Cape Cod hospitality. Steeped in history, this property is licensed for 12 rooms, accommodating up to 24 guests at a time. With its spacious layout and versatile floor plan, it offers an array of possibilities, including the potential for generous owner's quarters. The Captain's House is perfectly poised to continue its legacy as a thriving B&B, providing guests with an authentic Provincetown experience. For those seeking a more personal touch, the property's 13 bedrooms and 6 full baths make it a prime candidate for conversion into a magnificent single-family residence. Imagine the grandeur of living in a Federal Style home that has hosted countless stories and cherished memories over the years. Seller welcomes offers with requests for buyer concessions. The spaciousness and elegant architecture await your creative vision to transform this property into your dream coastal retreat. While the Captain's House Guest House exudes tranquility and seclusion, it's merely a stone's throw away from the public beach access, ensuring that sun, sand, and surf are just moments from your doorstep. Whether you envision running a thriving hospitality business or creating your private haven in one of Cape Cod's most beloved towns, this property offers a myriad of possibilities. Don't miss this rare chance to own a piece of Provincetown's history and shape its future. The Captain's House Guest House awaits its next captain, and it could be you. Come and explore the endless potential that this iconic property has to offer.

$3,500,000

4 Bed

3 Bath

West Tisbury

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Hickory Hollow is one of the most enchanting parcels of land in Seven Gates Farm. You enter the property and feel as if you have stepped back in time. The cozy antique farmhouse is the centerpiece of the 6.8-acre property which includes rolling lawns, lichen-covered stone walls and boulders, numerous specimen trees, and no fewer than 3 ponds. In addition to the main house there are 3 additional structures on the property. The historic barn features a studio apartment with kitchenette, bedroom area, full bath, and deck with a double garage below. There is also a small writer's study as well as a two-story garage/studio with a second floor balcony overlooking the grounds. Seven Gates owns two miles of private beaches, two large docks for swimming and boating, two tennis courts, and many miles of walking trails through 1600 acres of unspoiled association land.

$679,000

2 Bed

1 Bath

Oak Bluffs

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WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. If your preference is to build a new 5 Bedroom House instead, the Seller has already been through the lengthy process with the Martha's Vineyard Commission to receive approvals to knock down the house and has succeeding in obtaining that approval. According to the engineer who percolated the lot, the lot will allow a 5 bedroom regular septic system. The Board of Health have stated there are no Board of Health issues with this property and are deferring to the engineer's opinion. Water and Electricity are already at the site. Property is being sold in 'As is" condition. If BUYER chooses to remove the house and garage it will be at their expense. Retaining the footprint of the garage has value as it's a preexisting non conforming location on the lot and therefore could be rebuilt in place or possibly an ADU could be built on that footprint. Easy access to harbor, town, shops, restaurants, Oak Bluffs Ferry, Sunset Lake, Campground cottages, Oak Bluffs Library. Front porch for relaxing on a Summer evening. Easy to show! PRICED BELOW ASSESSED VALUE.

$1,100,000

2 Bed

1 Bath

Provincetown

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Pre-construction pricing! Just a short way down charming Pearl Street just beyond the Fine Arts Work Center and close to the gallery district - a newly renovated 2BR, 1BA condominium awaits its next chapter. Here, old Cape charm dances with fresh modern flair, and the town's storied vibrancy hums softly in the background. Spanning 736 square feet, this second-floor gem is bright and airy. The kitchen, with floating shelves and granite countertop, is tucked back from the living room yet open enough to keep you connected to the action. The living room has large windows that stream in plenty of sunlight and the oak floors beneath promise the laughter of many Provincetown summers to come. The full bath has a modern sensibility and is smartly configure with a stacked washer and dryer. And even more magic spills outdoors to a 240-square-foot deck which beckons you to pause and sip morning coffee where breezes stir your imagination as you stare out over the shared front lawn—complete with irrigation from a private well. Two tandem parking spaces ensure practical convenience, and with the ferry and Commercial Street's galleries just a short distance away, this home is perfectly poised to be your Cape Cod sanctuary. It's not just a place to live; it's a narrative of beauty, creativity, and connection waiting for you to pen the next chapter. No rental restrictions.

$1,250,000

2 Bed

1 Bath

Provincetown

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Pre-construction pricing! Just a short way down the charming Pearl Street just beyond the Fine Arts Work Center and close to the gallery district - a newly renovated 2BR, 1BA condominium awaits its next chapter. Here, old Cape charm dances with fresh modern flair, and the town's storied vibrancy hums softly in the background. Spanning 1,000 square feet, this first-floor wonder is the belle of its three-unit association's ball. The kitchen, a sunlit stage for culinary escapades, unfolds with an inviting spaciousness that hints at hearty dinners and impromptu gatherings. The living room, anchored by a high-end electric fireplace, radiates warmth and ambiance, while the oak floors beneath promise the laughter of countless Provincetown summers. A modern bathroom balances elegance and utility, and the primary bedroom's walk-in closet is so big it could double as a mini-gallery for hanging treasures from local galleries. And even more magic spills outdoors. A 240-square-foot covered porch beckons you to pause and sip morning coffee as breezes stir your imagination as you stare out over the shared front lawn - complete with irrigation from its private well. Meanwhile, a large deck off the kitchen promises grilling and lively gatherings under the open sky. Two tandem parking spaces ensure practical convenience, and with the ferry and Commercial Street's galleries just a short distance away, this home is perfectly poised to be your Cape Cod sanctuary. It's not just a place to live; it's a narrative of beauty, creativity, and connection waiting for you to pen the next chapter. No rental restrictions.

$3,700,000

6 Bed

4 Bath

Oak Bluffs

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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 warp 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.