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$12,000,000
4 Beds ⋅ 3 Baths ⋅ 22603612 MLS
The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a private retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham
$950,000
3 Beds ⋅ 1 Baths ⋅ 22603601 MLS
This charming cottage is in a coveted location close to Hardings Beach and Barn HIll town Landing with iconic oyster shanties and access to Oyster River, Stage Harbor for kayaking & paddleboarding. 2 marinas are also nearby for boating fun not to mention all the local dining options and bike trail. This adorable quintessential Cape Cod cottage has been updated with newer kitchen and bath, skylights, decorated with panache enhancing summer rental investment. Detached 2 car garage is a bonus and the unique '' sleeping under the stars'' porch in the trees adds to the ambiance, creating memorable happy summers in Chatham. Connected to town sewer on a level 23, 741 sq ft lot, it offers many possibilities for potential expansion. Furnace non functional, buyer to install new one or mini splits for heat/AC if desired. Opportunity Knocks! Showings ONLY on Sunday rental turnover days July 26th, Aug 2nd, Aug.16th only 12-3PM.

268 Barn Hill Road, Chatham
$695,000
2 Beds ⋅ 1 Baths ⋅ 22603438 MLS
Nestled on a private lane in one of Chatham's most sought after locations, this home has been enjoyed by the same family since 1946 and occupied as a year round home for 40 years. This is a rare opportunity to create your own Cape Cod retreat just moments from Oyster River, the Oyster River Boatyard, and nearby Hardings Beach. Bring your vision to the charming, light-filled home full of original character, vaulted ceilings and ready for its next chapter. Whether you're dreaming of restoring its vintage charm or exploring future possibilities, this is a rare chance to own in Chatham. The property is being sold AS IS. Buyers should anticipate the need for a new Title V septic system and replacement of the existing oil tank to meet current town requirements. All information contained herein is deemed reliable but is not guaranteed. Buyers & buyers agents should perform their own due diligence regarding future use and development potential and independently verify all information.

40 Uncle Abner's Path, Chatham
$9,995,000
3 Beds ⋅ 3 Baths ⋅ 22603522 MLS
Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and possibility. Beyond the home's welcoming presence, a surprisingly private landscape unfolds, where mature plantings, a sweeping lawn, a carriage-style garage, and a swimming pool create an extraordinary retreat. Inside, the home was designed for gracious living, with spacious rooms and classic details, equally suited to entertaining or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs, charming windows frame picture-perfect coastal scenes. Whether enjoyed as it is today or reimagined, this is a rare opportunity to begin its next chapter. This special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Road, Chatham
$795,000
4 Beds ⋅ 4 Baths ⋅ 22603514 MLS
Tucked away on a cul-de-sac in W. Chatham this spacious 4 bed/ 3.5 bath Cape offers potential in a peaceful setting. Set back from the road with a canopy of trees, this property feels private & serene with seasonal views of a scenic cranberry bog & birdlife. The main level features an open sunny living/dining area, 2 picture windows & slider to wraparound deck, hardwood floors and wood burning Fireplace. The good sized kitchen has wet bar and Breakfast bar seating, Stack WD laundry& pantry area, plus half bath in hallway. The 1st Fl primary bedroom is ensuite with bath. Upstairs are 3 good sized bedrooms, full bath & ample storage closet. The 674 sq ft finished walk out lower level with separate entrance slider offers flexibility for office, TV entertainment room with built in bar ready for gatherings. Nearby is the CC Rail Trail access for biking/ walking or Marion's Pie shop for coffee, a short drive to Ridgevale Beach. Excellent opportunity for next owner to bring their vision and updates to make it truly shine. Great for year round or vacation rental options...lots of possibilities with 3 levels of living space.

19 Joshuas Way, Chatham
$4,250,000
3 Beds ⋅ 4 Baths ⋅ 22603504 MLS
Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and sweeping water views. Glass doors lead from the living room to a deck and patio overlooking the water, creating the perfect setting for entertaining or relaxing. The first floor also features a waterfront dining room, kitchen, spacious primary suite, wood-paneled den, powder room, laundry, and an attached two-car garage. A charming side porch provides yet another inviting outdoor retreat with spectacular water views. Upstairs, two guest bedrooms enjoy water views and share a full bath. The walkout lower level offers a family room, office, full bath, natural light, and excellent storage. Experience Cape Cod's finest waterfront living with boating, kayaking, swimming, and fishing right from your private sandy beach. Ideally located next to Eastward Ho! and a short drive to downtown Chatham.

600 Fox Hill Road, Chatham
$468,000
2 Beds ⋅ 2 Baths ⋅ 22603405 MLS
Beautifully remodeled in 2023, this charming 2 bedroom, 1.5 bath Seasonal Cottage is just 0.8 miles from Hardings Beach . Thoughtfully updated and move-in ready, it features a private deck, spacious patio and outdoor shower; perfect for enjoying the Cape lifestyle. Ideally located just minutes from Chatham's acclaimed restaurants, boutiques, and beaches, this turnkey property baosts strong rental history, making it an execptional opportunity!

19 Captain Richards Way, Chatham
$2,390,000
4 Beds ⋅ 4 Baths ⋅ 22603375 MLS
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

55 Winterset Drive, Chatham
$2,750,000
22603371 MLS
Exceptional investment opportunity in the heart of downtown Chatham. This well-maintained, recently updated 1,920+/- SF freestanding commercial building sits on a prominent 0.63-acre parcel with ample on-site parking. Offered for sale is the real estate only; the property is fully leased to CODO Mexican Kitchen, a well-established and thriving restaurant with a long-term lease in place, providing stable cash flow for investors. The property's prime Main Street location offers outstanding visibility, strong pedestrian and vehicle traffic, and convenient access to Chatham's shops, galleries, beaches, and year-round attractions. The combination of a quality tenant, long-term lease, recent building updates, and one of Cape Cod's most desirable commercial locations makes this a rare opportunity for investors seeking a low-maintenance, income-producing asset in a premier market.Connected to Municipal sewer. 32 parking spaces.

859 Main Street, Chatham
$1,469,000
5 Beds ⋅ 10 Baths ⋅ 22603353 MLS
New co-ownership opportunity: own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho, and Pleasant Bay from nearly every angle. The classic shingle-style exterior includes a two-car garage and private boat dock with direct water access. The airy living room features a stone fireplace, window seats, and vast water views. The kitchen continues the view with a Wolf gas range, a large island, and doors opening to a deck overlooking Crows Pond. A formal dining room with raised panel walls and a butler's pantry with wet bar completes the main level. The three-level layout includes a quiet office, lower-level gym, indoor sauna, and a guest suite with its own kitchen and living room, all connected by an elevator. A pool, patio, and private dock anchor the outdoor spaces, with sunrise and sunset views from multiple balconies. Lighthouse Beach is close by, and Chatham's Main Street offers galleries, restaurants, and shops. Professionally managed by Pacaso and ready when owners arrive.

558 Fox Hill Road, Chatham
$1,800
22603315 MLS
Legendary Shop Ahoy Plaza - a well-known locallandmark● Excellent visibility on busy Route 28● Positioned between the two Chatham rotaries -maximum exposure and accessibility● Great signage potential to capture drive-by attention● Large storefront display windows - ideal for retailvisibility and merchandisingFront and rear egress - easy access for customers anddeliveries● Oversized storage area below● On-site parking - convenient for staff and patrons● Half bath● HVAC - forced hot air and air conditioning● Municipal sewer● Sprinklered and fire alarm systemRent is per month plus Utilities and Fees.

1589 Main Street, Chatham
$1,495,000
2 Beds ⋅ 4 Baths ⋅ 22603300 MLS
Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers ball games, concerts, Oyster Pond, and more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen, adjacent dining area, and comfortable living room. A French door opens to a 15 x 10 deck for outside relaxation. Upstairs there are two en-suite bedrooms - each with peeks of the water and a lovely private bath. The walk-out lower level provides additional living space/family room plus full bath, perfect for overflow. Amenities include a one-car garage, 1/2 bath, and 2nd floor laundry. Reasonable condo fees that include outside maintenance allow you to relax and enjoy your Chatham time. Don't miss this very special offering in a prime, walkable location!

739 Main Street, Chatham
$5,900,000
4 Beds ⋅ 5 Baths ⋅ 22603274 MLS
Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and additions in several directions in this very private location of North Chatham...Choice of 3 primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the recently retiled heated Gunite pool....House has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more......All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc.. Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut Road, Chatham
$2,995,000
4 Beds ⋅ 4 Baths ⋅ 22603172 MLS
Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously updated 2,700-square-foot residence features 4 bedrooms and 3.5 bathrooms. Just a short distance from Nantucket Sound and Hardings Beach, this craftsman-renovated home offers a spacious open floor plan highlighted by vaulted, beamed ceilings and expansive windows that showcase ever-shifting views of the tidal marsh. Designed to host guests, the first floor includes a stunning professional-grade kitchen with an oversized quartz island that opens to an elegant dining area, two fireplaces, and two primary bedroom suites. The property is rounded out by a large wrap-around deck, two additional second-floor bedrooms, a one-car garage, and a full basement with heat and air conditioning. The house is .7 mi from Harding's Beach and 1.9 miles from downtown Chatham's shops and restaurants. Pull up a chair and savor Mother Nature's ever-changing show.

26 Hardings Beach Road, Chatham
$1,100,000
22603130 MLS
Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement.Properties located at 1134 Main Street and 1142 Main Street must be purchased together and will not be sold separately.Ideal for investors, entrepreneurs, owner-users, or redevelopment, this unique offering provides the opportunity to acquire well-positioned Main Street commercial real estate with outstanding visibility and long-term potential.

1134 &1142 Main Street, Chatham
$1,100,000
22603123 MLS
Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement.Properties located at 1134 Main Street and 1142 Main Street must be purchased together and will not be sold separately.Ideal for investors, entrepreneurs, owner-users, or redevelopment, this unique offering provides the opportunity to acquire well-positioned Main Street commercial real estate with outstanding visibility and long-term potential.

1134 &1142 Main Street, Chatham
$1,275,000
3 Beds ⋅ 2 Baths ⋅ 22603060 MLS
Sought after neighborhood of Riverbay. Light and bright home with incredible gardens and fabulous outdoor space. Three bedrooms 2 newly redone baths with livingroom, dinng room and primary suite all with sliders onto the deck with spiral stairway to back yard for super summer fun. Room for a pool! Lower level could be finished off-high ceilings and windows overlooking the back yard. Deeded rights to 2 ponds for kayaking, canoeing and fishing. Come take a look at this special property.

240 Riverview Drive, Chatham
$1,069,000
3 Beds ⋅ 3 Baths ⋅ 22602982 MLS
Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.Offering 1,754 sqft of main-level living, the home many features include an updated eat-in kitchen, large living room with fireplace, and a dining room that leads you towards two distinct, comfortable sitting areas that open to expansive decks with winter water views. 1632 sf of additional finished space in the walkout lower level add tremendous flexibility. Recent improvements include a new roof, new windows, kitchen renovations, and cooling systems. Generous living spaces, thoughtful updates, and a serene Chatham setting, make this home ready to be enjoyed for years to come.

65 Captain Kendrick Drive, Chatham
$2,399,000
22602911 MLS
Downtown Chatham location, just beofre the Main Street Rotary. Three finished levels: The first floor currently consists of a professional reception area, waiting room, and five private offices designed for efficient client-facing operations. The second floor includes six additional offices and a full bathroom, allowing for flexible administrative, executive, or possible residential adaptation.The lower level offers two half bathrooms, lounge space, additional finished areas, utility access, elevator mechanical room access, and substantial unfinished storage space. This lower level configuration provides flexibility for back-office operations, storage, staff amenities, or additional future buildout.Central air conditioningNatural gas heatWood frame constructionProfessional signageRear accessPublic sewer serviceProminent Main Street frontage

697 Main Street, Chatham
$6,500,000
10 Beds ⋅ 10 Baths ⋅ 22602857 MLS
Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500 sq ft with 10 bedrooms and 10 bathrooms. Inside, enjoy hand-painted murals, sweeping water views, curved staircases, intricate woodwork, and beautifully scaled living spaces filled with character. The lower level features a ''speakeasy'', ballroom, workshop, and storage. Outside, expansive terraces, mature gardens, bluestone walkways, towering trees, and rolling lawns create a spectacular setting leading toward the water. In 1978, the property was divided into three townhouse residences, each with private entrances, kitchens, living areas, laundry, terraces, and separate utilities. The property has since been used as a single-family home, but offers remarkable flexibility as either a grand estate or redevelopment opportunity. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham
$1,199,000
4 Beds ⋅ 3 Baths ⋅ 22602848 MLS
Welcome to Riverbay Estates, where Cape Cod charm meets endless potential. Enjoy peaceful mornings and beautiful water views from nearly every room in this spacious home. This, well-built 4-bedroom, 3-bath home offers direct access to Pickerel Pond for kayaking and enjoying nature. A true ''diamond in the rough'' project with great bones ready for your updates and personal vision. The, main level features a living room, dining area, kitchen, first-floor primary suite, guest bedroom, and full bath. Upstairs are two additional bedrooms, a full bath, and two expansive walk-in attic spaces offering exceptional storage or future expansion potential. Additional, amenities include first-floor central A/C, natural gas heat, an attached two-car garage, and generator ready. Tucked away in a quiet neighborhood just minutes from Chatham's Main Street, Pleasant Bay, beaches, shopping, and dining, this is a rare opportunity to create your dream Cape escape

68 Chippingstone Road, Chatham
$2,100,000
1 Beds ⋅ 2 Baths ⋅ 22602838 MLS
Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. There are 5 private in-town parking spaces behind the building and is located in the coveted GB-1 zoning district that has the most versatile business-use options available. The first floor commercial space features an open floor plan with 3 large areas and 4 oversized showcase windows putting your business directly in front of passing pedestrian traffic. The second floor apartment was fully renovated in 2019 and includes one bedroom, a full bath and laundry, and an open concept kitchen and a living area with vaulted ceilings. A large mahogany deck provides excellent outdoor living space. Both floors are independent of one another with separate A/C and heat. Don't miss this opportunity to own a versatile property that offers both exceptional business potential and strong investment value. Seller is the Owner/Broker.

409 Main Street, Chatham
$2,100,000
22602839 MLS
Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. There are 5 private in-town parking spaces behind the building and is located in the coveted GB-1 zoning district that has the most versatile business-use options available. The first floor commercial space features an open floor plan with 3 large areas and 4 oversized showcase windows putting your business directly in front of passing pedestrian traffic. The second floor apartment was fully renovated in 2019 and includes one bedroom, a full bath and laundry, and an open concept kitchen and a living area with vaulted ceilings. A large mahogany deck provides excellent outdoor living space. Both floors are independent of one another with separate A/C and heat. Don't miss this opportunity to own a versatile property that offers both exceptional business potential and strong investment value. Seller is the Owner/Broker.

409 Main Street, Chatham
$999,000
22602638 MLS
Build your 3 bedroom home in this awesome downtown location walk to everywhere you want to be in Chatham. Meander across the street to Chatham A's Lilly's, the Squire steps to Oyster Pond no car necessary. The property is surrounded by amazing gardens. A sanctuary a feast for the eyes. Call your builder bring your imagination. A oasis in downtown Chatham.

727 Main Street, Chatham
$849,000
2 Beds ⋅ 1 Baths ⋅ 22602398 MLS
Tucked away in the heart of Chatham, 66 Snow Lane offers a rare blend of privacy, convenience, & natural beauty. This charming 2-bedroom, 1-bath ranch-style home is surrounded by conservation land, creating a peaceful setting where birds, wildlife, and wooded views can be enjoyed from every window. Thoughtfully designed for easy one-floor living, the home features a wood burning fireplace, first-floor washer & dryer, gas heat, and central AC, outdoor shower, newer shed, making it a comfortable retreat in every season. While the setting feels quiet & removed, the location is wonderfully close to everything that makes Chatham so special. Just 0.4 miles to the village and Veterans Field and a 5 min walk to Oyster Pond. You can stroll into town for shopping, restaurants, theater, movies, and summer baseball, then return home to the calm and privacy of your own little escape. Whether you are looking for a year-round residence, a Cape Cod getaway, or a low-maintenance retreat near the center of town, this delightful home offers the best of both worlds: in-town convenience with the feeling of being away from it all. Sewer at the road, hook-up is designed & ready for the buyer to connect.

66 Snow Lane, Chatham
$4,395,000
4 Beds ⋅ 6 Baths ⋅ 22602319 MLS
Situated on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath, shingle-style residence is designed for seamless indoor and outdoor entertaining. The bright, airy first floor is anchored by a great room with a Rumford fireplace, custom cabinets, 10' ceilings, and towering windows. The professional-grade kitchen features premier appliances, a pantry, a wet bar, and a large center island. Primary suites are on both floors, each with a large walk-in closet and a luxurious bath. The fenced-in yard offers two exceptional options for installing a large swimming pool and spa to complement the bluestone patio and built-in gas grill. The second story features an inviting family room with custom-built-ins and a gas fireplace, opening onto a broad deck with views of the Atlantic Ocean and the Outer Beach. The second-floor primary is complemented by two well-appointed guest suites. A private staircase leads to the bonus room with a full bath, located above the two-car garage and ideal for a gym, office, or guest accommodations. A whole-house generator and an in-ground irrigation system supplied by a private well add to what is an unparalleled value in the Chatham real estate market.

335 Stage Island Road, Chatham
$4,950,000
4 Beds ⋅ 5 Baths ⋅ 22602178 MLS
Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance and is turn key, furnished and ready for summer! Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native plantings--setting a captivating tone before you even step inside. The foyer sets the stage for the exceptional design that unfolds within. Built by Steven Nickerson, meticulous millwork, custom Kochman Reidt+Haigh cabinetry accentuating many spaces, and intricate architectural details are found throughout the home. The house boasts an extraordinary level of artistry and craftmanship. The main living room with fireplace is refined yet comfortable and flows seamlessly into an intimate sitting area, partitioned by a custom-built cabinet containing a motorized TV lift, creating multi-use spaces. Smart home technology enhances both functionality and ambiance throughout.

15 Bay Lane, Chatham
$4,200,000
3 Beds ⋅ 3 Baths ⋅ 22602056 MLS
Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story dining area and reading loft, both set off by a soaring wall of windows with water views. The chef's kitchen offers bar seating, while a versatile bedroom or study, full bath and mudroom complete the floor. The primary suite is a quiet retreat, featuring a fireplace, built-in bookshelves, a window seat and a luminous stained-glass accent window. A second guest suite with vaulted ceilings completes the upper level. The walk-out lower level provides generous family space, custom built-ins, abundant storage and room for expansion. Outdoors, mature plantings, stonework, a large deck and a pergola patio create a seamless connection to the landscape. As part of the Bucks Creek Association, residents enjoy access to a private picnic area and dock on Nantucket Sound. The nearby Cape Cod Rail Trail offers an easy, scenic ride to downtown Chatham and surrounding towns.

30 Indian Trail, Chatham
$2,995,000
3 Beds ⋅ 3 Baths ⋅ 22601983 MLS
Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, this property delivers a generational setting defined by sweeping marsh and water views, breathtaking sunsets, and a bucolic lot surrounded by abundant conservation land.The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light. A wall of windows and doors anchors the main living area with 270-degree views. The private primary suite features its own deck and a soaking tub with waterfront views -- an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks unfold into multiple entertainment zones designed for alfresco dining, yard games, and summers well spent. Move-in ready and meticulously maintained, the expansive footprint also offers meaningful runway for further development. A setting this rare, in a community this sought-after, does not come twice.

336 Stage Island Road, Chatham
$2,350,000
22601891 MLS
Conveniently positioned along Main Street in Chatham, this fully renovated housing complex offers a rare and compelling investment opportunity in one of the Cape's most supply-constrained markets. Ideally suited for workforce, employee, or long-term housing, the property is approved by the town for 33 beds and features 12 total units, each designed for comfort, privacy, and efficiency. The property includes 10 individual room units, each with a bath, small kitchenette, and heating and cooling; a main house with four bedrooms, three bathrooms, and a full kitchen; and an attached two-bedroom apartment with its own kitchen and bath. Connected to the town sewer and located on the Route 28 bus line, the property offers accessibility for tenants and employers. Extensively renovated in 2026, improvements include flooring, plumbing, electrical, siding, paint, roof, landscaping, and a shared laundry room with three new coin-operated washer and dryer sets. With several leases in place, the asset offers immediate income. Turnkey, low-maintenance, and positioned in a market with persistent housing demand, this is a rare opportunity to acquire a high-performing investment property Chatham.

1547 Main Street, Chatham

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