274 properties for sale in Chatham, Chatham town Barnstable County Massachusetts

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

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

In the heart of Chatham's Old Village, 90 Silver Leaf Avenue brings together historic Cape Cod character and inviting spaces for everyday living. Thoughtfully restored, the home features pine floors, a living room with gas fireplace, and a kitchen that opens to a light-filled family room. A dining room and wet bar make gatherings easy, while a first-floor ensuite bedroom offers flexibility for guests. Upstairs, the spacious bedroom suite has cathedral ceilings, skylights and a walk-in closet. The finished lower level provides additional space for recreation or a home office. Outside, enjoy the deck, outdoor shower and a detached cottage beside the two-car garage. From this Silver Leaf Avenue address, Chatham's shops and restaurants, Lighthouse Beach, Mill Pond, bandstand concerts and summer baseball are all close at hand. The property received a 2012 Chatham Preservation Award for its restoration

Situated at the end of a private lane, this North Chatham 4-bedroom, 4.5-bath home on 1.2 acres offers a bright, open layout with numerous updates and energy-efficient smart home upgrades and is being offered furnished. The expansive, sun-filled family room centers on a wood-burning fireplace and flows seamlessly to a spacious treetop deck. The first-floor primary bedroom suite features a spa-like private bathroom with radiant heat and a private deck. The upgraded kitchen features custom cabinets and granite countertops, an expanded sunroom/breakfast nook, and a formal dining room. The second floor boasts two bedroom suites, a study, and a laundry room. The finished lower level includes a bedroom, living room, kitchen, full bath, and separate exterior entrance. Other features include a two-car garage, A/C, a new 26 KW generator, and new energy-efficient heat pumps. The house has a terrific rental history and is located close to the town landings at Cotchpinicut Rd and Scatteree Rd, as

Brand new septic Title V and town water are installed ! Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural gas and town water in the road, The wood burning fireplace creates ambiance when sitting in the family while relaxing with a good book or watching TV. The yard is filled with beautiful perennials that explode throughout spring and summer

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

Set on a tranquil dead-end lane in Chatham's Old Village, this 2006-built home pays homage to its 1720 predecessor, blending classic charm with modern living in one of the town's most appealing locations. Just steps from Lighthouse Beach and downtown Chatham, this remarkable property offers an exceptional opportunity for a full-time residence, summer getaway, or investment home. Designed for entertaining family and friends, the main level features a bright, open-concept living area with a cozy gas fireplace, hardwood floors, a distinct dining space, and a light-filled kitchen with a center island and pantry closet. French doors lead out to a private, beautifully landscaped fenced-in yard with a stone patio, gas fire pit, outdoor shower, and a charming shed. A main-floor primary bedroom, full bath, and cozy den or office complete this level. The upper level hosts two additional bedrooms and a full bath. The expansive lower level adds even more versatile space, including an entertainment

SOLITUDE, A Sophisticated Chatham Antique Tucked away in one of Chatham's most coveted locations, Solitude offers a blend of a private, tranquil setting while just moments from town, Seaside Links Golf Course, and Claflin Landing Beach. This exquisite 5-bedroom, 3.5-bath antique has been masterfully restored, with an emphasis on preserving its timeless character with refined aesthetics. original glass windows, gorgeous wide pine floors, hand-finished woodwork, and four fireplaces. A stunning kitchen and beautifully appointed modern bathrooms bring effortless refined character to the home, while a subtle peek of Chatham Harbor adds to its coastal allure. Outside, private gardens and an expansive yard create a secluded enclave for relaxed Cape Cod living, with a brick terrace, a separate patio with a pergola, and a detached one-car garage. Solitude is a truly special Chatham offering, where history, craftsmanship, privacy, and an extraordinary location come together

Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed to maximize its breathtaking setting, the light-filled open floor plan features walls of glass and stunning water views from nearly every room. The main level includes a spacious living room with a fireplace, dining area, updated kitchen, two bedrooms, and a shared bath. Upstairs, two private en-suite bedrooms enjoy elevated harbor vistas. The walkout lower level offers a family room and fitness space overlooking the water. A 2025 kitchen renovation, 2019 revetment, and direct water access for kayaking, paddleboarding, fishing, clamming, and swimming make this an exceptional opportunity

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

One of the iconic Christopher Ryder House condominiums can be yours in time for the Fall season. This elegant two-bedroom, three-bath home blends timeless architectural character with refined two-level living. Gracious rooms, high ceilings, oversized windows, skylights, original beams, and warm wood floors create an inviting atmosphere throughout. The open floor plan features a spacious living room with gas fireplace flowing seamlessly into the dining room space and updated chef's kitchen—perfect for entertaining. A sunlit office space opens through sliding doors to a private patio, ideal for gatherings, gardening, or a peaceful outdoor retreat. The primary suite offers a walk-in closet and updated bathroom. The spacious second bedroom enjoys a nearby full hall bath, with the additional second office space providing flexibility for work or guests. Interior access to the garage, along with additional storage, adds everyday convenience. A rare opportunity to enjoy architectural charm, mo

A meticulously maintained and beautifully decorated beach home awaits you in the quaint village of South Chatham. Ideally situated between downtown Chatham and Harwich Port, this exceptional property offers the perfect blend of comfort, privacy, convenience and classic Cape Cod charm. Nestled near Forest Beach, Mill Creek, the Cape Cod Rail Trail, tennis court and conservation areas, this home puts nature and recreation at your fingertips. The spacious home features four bedrooms and three baths providing plenty of room for family and guests. Thoughtfully designed for comfortable living and surround sound for entertaining, the home offers inviting spaces inside and out. The two car garage has been transformed into a fantastic game room, complete with air hockey, ping pong and foosball-a wonderful space for kids and adults alike. Outside,the beautifully landscaped yard and gardens are irrigated by a private well, keeping everything lush throughout the season. Three decks one is a roof t

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 opportuni

A rare opportunity awaits high above the dunes of Hardings Beach to build the bluff house of your dreams. Nestled within the private enclave of Hall's Bluff, this five-bedroom home boasts majestic, sweeping views of Nantucket Sound, Monomoy Island, and beyond. The sunsets are spectacular. Ownership includes deeded access to a neighborhood footpath leading directly to Harding's Beach and the Oyster River. Built in 1957, the house is in poor condition, but will be a wonderful project for the right buyer

Welcome home to 3 Oyster Drive, a perfectly idyllic Chatham getaway! This enchanting cottage enjoys dazzling water views and a prime location near Outermost Harbor Marina, beaches, and Town. This 3 BR, 2 BA home is a blend of classic Cape Cod and some newer features and is the ideal backdrop to begin your own Chatham story. Many will find the home comfortable just the way it is, or choose to take advantage of approved house plans and construct an elevated new home on this one-of-a-kind site. First floor offers a bright living room with water views, beamed ceiling and fireplace. Cozy kitchen with adjacent dining area. A bedroom, bath, and laundry are also on this level. Upstairs: full bath and 2 more BRS including the primary w/skylights and amazing view! On-demand gas hot water heater, outside shower, and a wrap-around patio with views. Walk to the beach, bike to Town, fantastic rental potential, and water views is rare for this price in Chatham! Sold mostly furnished; don't miss out!

Welcome to 88 Indian Hill Road, where stunning curb appeal and timeless Cape Cod charm welcomes you home. Perfectly situated on a prominent, beautifully landscaped large lot, this sprawling Cape has been meticulously maintained and thoughtfully designed for both everyday living and entertainment. The private, tranquil grounds are a true highlight, featuring flowering ornamental trees, lush plantings, classic stone walls, and a private deck overlooking the peaceful, park-like setting, perfect for morning coffee, summer dining, or relaxing with family and friends. Inside, a spectacular custom great room with vaulted ceilings and abundant natural light is the heart of the home, complemented by a gracious living room and an elegant dining area ideal for entertaining. The first-floor primary suite offers comfort and convenience, while two inviting guest bedrooms provide wonderful accommodation for family and guests. Finished lower offers a spacious recreation room and private office. Deeded

In the heart of Chatham's Old Village, 90 Silver Leaf Avenue brings together historic Cape Cod character and inviting spaces for everyday living. Thoughtfully restored, the home features pine floors, a living room with gas fireplace, and a kitchen that opens to a light-filled family room. A dining room and wet bar make gatherings easy, while a first-floor ensuite bedroom offers flexibility for guests. Upstairs, the spacious bedroom suite has cathedral ceilings, skylights and a walk-in closet. The finished lower level provides additional space for recreation or a home office. Outside, enjoy the deck, outdoor shower and a detached cottage beside the two-car garage. From this Silver Leaf Avenue address, Chatham's shops and restaurants, Lighthouse Beach, Mill Pond, bandstand concerts and summer baseball are all close at hand. The property received a 2012 Chatham Preservation Award for its restoration

This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers Lake. Thoughtfully renovated in 2010, the main residence features an inviting and comfortable floor plan designed for relaxed living and entertaining. The updated kitchen with pantry opens to the dining area and living space, where views of the pool and grounds create a wonderful connection to the outdoors. A full bath and flexible office or bonus room provide additional options for guests, working from home, or overflow accommodations. Upstairs, the spacious primary suite offers a private retreat with a walk-in closet and en-suite bath featuring a whirlpool tub. A second en-suite bedroom and s

Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to be finished. Lots of possibilities - documents attached include Gb3 standard permitted uses section 3.4 and Appendix 1 'Schedule of Use Regulations', floor plans, and septic site plan. Great opportunities-previously a builders work shop and warehouse for storing automobiles, boats, vintage motorcycles etc. The solar panels are owned. Please verify all information contained herein. Don't miss this special property!

This fabulous, move-in-ready condominium is one of only two units and enjoys a private, desirable location at the end of the street overlooking the marsh. Extensive renovations completed in 2018 include the kitchen, bathrooms, roof, siding, windows, natural-gas heating and central air conditioning, plumbing, electrical systems, and IA septic system. In 2026, the private patio and fire pit were upgraded for the exclusive use of this unit. The monthly condominium fee includes water, flood insurance, landscaping, and the annual IA septic inspection. Just a short stroll to Ridgevale Beach and the Rail Trail, this property offers an easy and inviting Cape Cod lifestyle

Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water and doors to an expansive waterside deck. A versatile layout supports single-level living, featuring a first-floor suite currently enjoyed as a family room with a fireplace, soaring ceilings, full bath, and access to the deck. The upper level includes three bedrooms and a den, all benefiting from stunning outlooks. Professionally designed grounds provide a sense of seclusion, complemented by a private footpath to the shoreline. An exceptional offering in one of Chatham's most coveted waterfront locations

Steps from Cockle Cove Beach! This gorgeous, pristine 3-bedroom, 3-bathroom home offers the perfect blend of modern updates and beachside living. Located just steps from Cockle Cove Beach and right across the street from the Taylors Pond dock, this spotless property is completely move-in ready. Kitchen and Baths have been beautifully remodeled within the past few years. Walls were opened up to create a bright, seamless flow and allow winter views of Taylors Pond from the kitchen, dining area and the fire placed living room. Generous living spaces feature three distinct family areas to gather, relax, and entertain. A lower-level family room features its own full bathroom. It is the perfect escape for rainy days. Three Full Baths easily accommodate a house full of family and weekend guests. Beautiful, established gardens offer incredible curb appeal and are easy to maintain. The absolute best part of this home is where it sits. Walk right over to Cockle Cove Beach for or launch your kaya

Tucked away on a quiet neighborhood lane, 24 Kittys Lane captures the relaxed coastal lifestyle that makes South Chatham so special. This classic Cape Cod cottage is conveniently located near Nantucket Sound beaches, it is.3 to Forest Beach, the Cape Cod Rail Trail, conservation areas, local restaurants, shopping, and the many attractions in Chatham. Inside, the home offers 2 bedrooms, 1 bath, 768 sq ft of living space, and efficient split-system heating and air conditioning. An enclosed 112-square-foot porch provides a comfortable place to unwind, while a 190-square-foot loft offers versatile space. After a day at the beach, rinse off in the outdoor shower and relax on the deck overlooking the 10,000-square-foot lot that is increasingly valuable in the Chatham market. Passing 2-bedroom Title V septic. Ideally suited as a Cape Cod vacation home, seasonal retreat, investment property, rental opportunity, or creatively reimagined this charming cottage presents a wonderful chance to enjoy

Steps from Cockle Cove Beach! This gorgeous, pristine 3-bedroom, 3-bathroom home offers the perfect blend of modern updates and beachside living. Located just steps from Cockle Cove Beach and right across the street from the Taylors Pond dock, this spotless property is completely move-in ready. Kitchen and Baths have been beautifully remodeled within the past few years. Walls were opened up to create a bright, seamless flow and allow winter views of Taylors Pond from the kitchen, dining area and the fire placed living room. Generous living spaces feature three distinct family areas to gather, relax, and entertain. A lower-level family room features its own full bathroom. It is the perfect escape for rainy days. Three Full Baths easily accommodate a house full of family and weekend guests. Beautiful, established gardens offer incredible curb appeal and are easy to maintain. The absolute best part of this home is where it sits. Walk right over to Cockle Cove Beach for or launch your kaya

Spectacular custom-built Chatham home designed for effortless entertaining, offering three bedrooms, two bonus rooms, inviting living spaces on all three levels, and a picture-perfect backyard pool setting. A charming front porch welcomes you into a light-filled interior rich with coastal character. The main living room features custom built-ins, shiplap detail, and a wood-burning fireplace, flowing seamlessly into the chef's kitchen with top-of-the-line appliances, island seating, and a custom window that opens to the outdoor bar. The adjacent dining area is framed by sliders, creating exceptional indoor-outdoor flow. Outside, the private landscaped backyard is a true retreat, featuring a 34'x16' gunite pool, spacious patio, grilling area, deck, bar, outdoor shower, level lawn, and storage shed. Back inside, the main level also offers a primary suite with a spa-like bath, laundry room, mudroom, and storage. Upstairs are a family room, full bath, and two very spacious bedrooms. The fin

This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers Lake. Thoughtfully renovated in 2010, the main residence features an inviting and comfortable floor plan designed for relaxed living and entertaining. The updated kitchen with pantry opens to the dining area and living space, where views of the pool and grounds create a wonderful connection to the outdoors. A full bath and flexible office or bonus room provide additional options for guests, working from home, or overflow accommodations. Upstairs, the spacious primary suite offers a private retreat with a walk-in closet and en-suite bath featuring a whirlpool tub. A second en-suite bedroom and s

Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 2 spacious en-suite bedrooms with walk-in closets, 3 1/2 baths and extra space in the finished basement with full bath. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the dining and living areas with a gas fireplace. Amenities include Anderson Stormwatch windows, gas heat, central air and underground utilities provide year-round comfort. The finished lower level offers a Jacuzzi bath, antique pine bar, and pool table. Quality construction includes double-dipped cedar shingles, Azak trim and decking, heavy-duty asphalt roof, and three porches (two covered). This south-facing lot offers clse proximity to Nantucket Sound. Close to Forest Beach, post office, restaurants, package store, and Cape Cod Rail Trail, this beautifully crafted home offers exceptional qua

Canoe and kayak on Mill Pond. Direct water front at the end of the cul-de-sac. Turn key - Fully furnished year round and off season rental histoy. Very private and peaceful setting yet conveninet to shopping, restaurants, beaches and highways. 3 Bedrooms, 2 baths. First floor master. Plenty of closet space. Walkout basement. Large deck overlooking Mill Pond. Gas fireplace instert. Gas stove. Washer and dryer. May assume summer rentals

Few homes command Oyster Pond like 12 Pond Street. Three soaring peaks, the center crowned in sculptural rounded copper, announce a custom Eastward Companies build of rare craftsmanship, with immediate proximity to Main Street and the beach. Inside, every room turns toward the water. The open first floor is anchored by a kitchen perched above stunning views, its custom cabinetry and large island opening to a fireplaced living and dining area that flows to the waterfront patio. Just beyond, the primary suite offers built-ins, a gas fireplace, a walk-in closet, and a spa-like bath. Hardwood, high ceilings, and exceptional millwork carry throughout. Upstairs, a vaulted family room with wet bar opens to a porch set above the water, joined by three bedrooms and two full baths. Below, a fully equipped gym and entertaining space. Outside, a full paver driveway, retaining walls, and terraced bluestone patios frame hydrangeas and lush native plantings, with a gas firepit, outdoor shower, and ge

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