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$1,799,000
9 Beds ⋅ 9 Baths ⋅ 73504088 MLS
Once known as the Mashantum House & later the award-winning Four Chimneys Inn, this 9 bedroom/9bath, single family home, dating back to 1820, is set back, north of 6A on 1.6 acres & is close to everything! Directly across from Scargo Lake's landing; .4 mil to Howe's St. Beach on the bay; .5 mil to Dennis Village & just over a mile to Sesuit Harbor. This 3-story Victorian is the perfect place to live your Cape Cod Dreams. It may need exterior paint, but don't let that fool you...A new state of the art, 6-zone, gas HVAC system was installed & the interior of the home was painted in 2019; the roof was replaced on the main portion of the home in 2018 & in 2010, the farmhouse kitchen was updated from floor joists & floors to new appliances. Full of history & charm,from the elegant first floor with soaring ceilings, to the cozy 3rd floor with skylights & views of the lake, this substantial property has the potential to be a real stunner. An amazing investment or family home! A Must see!

946 Route 6a, Dennis

Listing courtesy of Listing Agent: Jennifer Monac from Listing Office: Today Real Estate, Inc..
$1,550,000
6 Beds ⋅ 5 Baths ⋅ 73502104 MLS
Beautiful sprawling property featuring the historic Captain's House (1802), guest cottage, screen house, and lush mature gardens throughout. The impeccably preserved main house offers 8-foot ceilings, wide pine floors, a spacious living/dining area, Baker’s pantry, first-floor bedroom with en suite bath, separate kitchen with Santa Cecilia Light granite, built-ins, and a den. Minisplits (2019) and two stairways lead to four additional bedrooms and three baths.The bright, airy cottage includes cathedral ceilings, full kitchen, private yard, and attached workshop—ideal for rental or caretaker use. Additional highlights include a 2-car garage, abundant storage, full-house generator, owned solar panels, and koi pond.Located near North Truro center, bay and ocean beaches, and Provincetown, this private compound offers exceptional charm and versatility. New 6-bed septic installed! (2 images digitally contain enhanced grass.)

16 Shore Rd, Truro

Listing courtesy of Listing Agent: Melissa Yeaw from Listing Office: Berkshire Hathaway HomeService Robert Paul Properties.
$1,095,000
7 Beds ⋅ 4 Baths ⋅ 73500376 MLS
The numbers work for this investment property. Three separate homes on one lot. Fully rented with yearly income over $82,000 with minimal expenses. Tenants are responsible for their utilities. The rear unit is brand new and cute as a button, the middle unit has been freshly painted and has new heat. The front unit has hardwood floors, updated kitchen, and many updates in 2020. Just around the corner from Sundae School, Wee Packet, La Scala, Seaview Park and great southside beaches, this is a great opportunity to own and earn from your Cape Cod property.

117 Depot St, Dennis

Listing courtesy of Listing Agent: Terri Gordon from Listing Office: Fathom Realty MA.
$6,488,000
7 Beds ⋅ 7 Baths ⋅ 73499989 MLS
Experience one of Cape Cod's most exceptional luxury estates, where private lakefront serenity meets effortless access to Nantucket Sound. Newly constructed in 2025 and offered fully furnished, this spectacular 6,700 sq. ft. residence is set on 2.52 secluded acres with 7 bedrooms, 6.5 baths, a heated pool, wine cellar, home theater, and 3-car garage. Walls of glass frame tranquil water views, while soaring ceilings, designer finishes, and a chef's kitchen create an extraordinary setting for entertaining and everyday living. Swim, kayak, paddleboard, or fish from your backyard, then keep your boat just minutes away at Ryder's Cove, Wychmere, or Saquatucket Harbors. Rarely does a home combine this level of privacy, luxury, recreation, and turnkey convenience. A true multigenerational retreat designed for unforgettable gatherings and the very best of Cape Cod living.

19 Walkerwoods Dr, Harwich

Listing courtesy of Listing Agent: Marirose Lynch from Listing Office: RE/MAX Real Estate Center.
$1,200,000
7 Beds ⋅ 3 Baths ⋅ 73493357 MLS
Buyers changed their plans and this prime property located in downtown Buzzards Bay is available to the wise investor. It has views of the railroad bridge and is a stones throw to the Cape Cod Canal. Currently there are 3 rental units and a 4th unit which is open to imagination. The town of Bourne has placed liberal zoning on the area of this property which allows for further development to the site. All units were remodeled to the studs in 2012 & 2013 and new electrical, plumbing, wall board and heating and hot water systems were installed. Most appliances will remain. Liberal Village zoning "may" permit adding additional units. This is an outstanding opportunity to be part of the thriving downtown of Buzzards Bay which is home to the Massachusetts Maritime Academy, the National Marine Life Center and many visitor attractions.

151 - 153 Main St, Bourne

Listing courtesy of Listing Agent: Ralph J. Grassia from Listing Office: Conway - Wareham.
$4,750,000
6 Beds ⋅ 7 Baths ⋅ 73479712 MLS
Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.

48 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$2,795,000
19 Beds ⋅ 28 Baths ⋅ 73461696 MLS
The property is situated on over 2.22 acres of waterfront property overlooking The Herring River. The site has two landing areas, with dockage potential, where easy access to Nantucket Sound can be found by traveling south on the river to open waters of The Sound via Kayak, Paddle Board, Canoe or the like. The land is improved by four buildings with 11,900 SF. The main building is 7,922 square feet and has a large restaurant space previously and spacious commercial kitchen area, three / four bedrooms, and five bathrooms. The previous restaurant had a capacity of around 375 persons based on municipal records. The Backhouse, which is located behind the Main Building has seven bedrooms and four bathrooms, living / dining rooms and deck overlooking the Herring River. The Side Cottage, located to the left of the Main House has four bedrooms, and two baths. There is also a large shed building to the rear of the property used for storage. Waterfront location, history, development potential, s

126 Route 28, Harwich

Listing courtesy of Listing Agent: Christopher Manning from Listing Office: William Raveis Real Estate & Homes Services.
$21,500,000
13 Beds ⋅ 14 Baths ⋅ 73457530 MLS
A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. This inimitable compound features a seven-bedroom main residence and a guest house with four bedrooms and two separate apartments with private entrance, providing refined accommodations for multi-generational living and staff. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

151 & 155 Irving Avenue, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$10,900,000
7 Beds ⋅ 8 Baths ⋅ 73456699 MLS
Rocky Island offers old Cape charm with a modern stylish interpretation, fully renovated in 2014 with up-to-date systems, and winterized for off season enjoyment. Connected to the mainland by a wooden bridge, it provides the privacy and safety of a true island and the ease and accessibility of a mainland property. Sandy beachfront, seasonal deepwater dock, pool, and a pool house/garage. Wrap around covered porch for panoramic water views and sunsets. Seven bedrooms each with water views, seven full and one half baths, and three fireplaces. Potential for three additional bedrooms. Plenty of space inside and out on your own private island.

75 Winsor Road, Bourne

Listing courtesy of Listing Agent: G. Stewart Young from Listing Office: LandVest, Inc..
$4,249,000
6 Beds ⋅ 5 Baths ⋅ 73426596 MLS
WATERFRONT ESTATE – This rare Cape Cod retreat blends classic coastal architecture with modern refinement. Refreshed with new siding and a Red Cedar roof (August 2025), the home offers 6 bedrooms and 5 baths, a chef’s kitchen with Viking professional gas range, Sub-Zero refrigerator, and center island with prep sink flows seamlessly into the sun-filled living room, dining area, and waterfront sunroom. The main residence includes a 2-car garage and full basement, while a versatile guest house with its own 2-car garage and striking fieldstone fireplace invites endless possibilities as a one or two-bedroom retreat, artist’s studio, game room, or workshop. Set on 3.8 private acres, the estate features a heated in-ground pool, landscaped grounds, and direct access to tidal waters. More than a residence, it is a private Cape Cod sanctuary offering beauty, privacy, and an unparalleled coastal lifestyle. 2-Year Choice ULTIMATE Home Warranty included. Some photos virtually staged.

4390 Main, Barnstable

Listing courtesy of Listing Agent: Robert MacKinnon from Listing Office: eXp Realty LLC.
$7,750,000
7 Beds ⋅ 11 Baths ⋅ 73383981 MLS
Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

440 Grand Island Dr, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
$4,499,000
8 Beds ⋅ 9 Baths ⋅ 73377530 MLS
Nestled in the heart of the West End, this historic 1847 Greek Revival Captain's Home is now available for purchase after 29 years under the same ownership. As one of the largest buildings in the neighborhood, the West End Inn serves primarily as a private residence but is also licensed as a B&B. The first floor was completely renovated in 2019. The property features three kitchens, a kitchenette, and four separate living quarters, each with private entrances. The light-filled, three-family layout offers potential to be converted into a substantial single-family home. There are nine bathrooms, eight bedrooms, two dens, two decks, two private garden spaces, and a beautifully appointed front yard. The top floor, with its large deck, provides water views and unobstructed vistas of Telegraph Hill and stunning sunsets. Parking is available for five or more cars, and beach access is directly across the street. Betterment paid in full.

44 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.
$2,700,000
7 Beds ⋅ 7 Baths ⋅ 73373131 MLS
For the first time in generations, this landmark Pleasant Bay compound—anchored by the iconic "Topside" main residence and the charming two-bedroom "Boathouse"—is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, "Topside" offers 5 bedrooms and 4.5 baths with timeless coastal character and spaces designed for gathering, while the "Boathouse" sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied, landmark waterfront settings.

645 S Orleans, Orleans

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$999,000
7 Beds ⋅ 5 Baths ⋅ 73306126 MLS
35 Pleasant Street in Hyannis is located in downtown Hyannis, 0.2 miles from Hyannis Harbor. Built in 1853, this seven bedroom home also has the original barn/stable on the property giving it a historic New England charm. With 0.27 acres of land, the property sites in the Downtown Village Zone allowing for personal home use or investment potential. Please schedule a walk through of the property.

35 Pleasant, Barnstable

Listing courtesy of Listing Agent: Charles Carey from Listing Office: Carey Commerical, Inc..
$9,950,000
6 Beds ⋅ 9 Baths ⋅ 73285680 MLS
Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views. The grand interiors seamlessly blend with the exquisitely landscaped outdoor spaces, featuring an inground pool, hot tub, spacious pool house, and a substantial private deep-water dock. Upon entering the home, the grand foyer leads you into the magnificent great room with a two-story custom fireplace, where panoramic vistas of the water and breathtaking sunsets set the scene for unforgettable family gatherings as well as effortless entertaining. The generous floor plan also features a refined library, formal dining room, a gourmet kitchen with center island, custom cabinetry and top-of-the-line appliances and a state-of-the-art home theatre. The six en-suite bedrooms include a first-floor suite with French doors leading to the back yard and a lavish primary suite with a luxurious bathroom, two walk-in closets and a private deck overlooking the water. Enhanced with modern conveniences such as a Sonos whole-house sound system and a 9-zone Hydro air system, every detail has been carefully planned and implemented. Additional highlights include a private guest suite above the attached 3-car garage and a sprawling entertainment room with a balcony on the third level highlighted by western exposure to experience breathtaking sunsets. Located just minutes from the upscale boutiques and renowned dining of Osterville village, this extraordinary property offers a lifestyle of unparalleled elegance and tranquility by the sea. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

501 Eel River Rd, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

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