760 houses for sale in Chatham, Chatham town Barnstable County Massachusetts

Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha's Vineyard Interior Designs. Walls of glass frame sweeping vistas and invite natural light to pour in throughout the home. Indoor and outdoor spaces flow effortlessly, from sun-drenched rooms to generous decks, terraces, and a resort-inspired pool area. The main living areas reflect a thoughtful balance of comfort and sophistication, highlighted by warm wood floors, layered textures, and expertly curated finishes. Multiple sitting and entertaining spaces offer room for every rhythm of daily life, including an expansive lower level with a glass-enclosed wine room, custom bar, game area, and media lounge. The kitchen and ancillary workspaces continue the home's blend of beauty and function, with sleek cabinetry, open shelving, and abundant natural light from picture windows overlooking the landscape

Just 0.4 miles from the sandy shores of Pleasant Street Beach, this enchanting South Chatham Cape-style cottage captures the timeless charm of Cape Cod living. Set down a private lane on a tree-lined lot, this storybook home is filled with warmth and character. The sun-filled interior features an open living and dining area heated by a cozy natural gas stove, a cheerful kitchen with a butcher block island, two inviting bedrooms, one full bath, and an easy single-level floor plan. Step outside to discover your own secluded oasis, where a brick patio, outdoor shower, fire pit tucked beneath the trees, colorful hydrangeas, and raised garden beds create the perfect setting for relaxing and entertaining after a day at the beach. Whether you're searching for a charming year-round residence or a treasured Cape Cod retreat, this special home offers the perfect setting to enjoy life in Chatham. Property is being sold fully furnished and in as-is condition. Excellent rental potential

This is the South Chatham beach house everyone is looking for! Fully renovated and turnkey, 124 Pleasant Street is ready for immediate enjoyment. As a private retreat of your own, or as a proven, guest-favorite rental. A short walk to Pleasant Street Beach, this South Chatham location grows only more desirable year over year. The living room, anchored by a fireplace, flows into the dining room and a well-finished kitchen with updated appliances, with first-floor laundry for convenience. Four well-appointed bedrooms offer easy privacy for family, friends, or guests, including an enchanting staircase leading to a second-floor hideaway all its own. A vaulted, screened sunroom connects indoors to out, and a side porch sets the stage for al fresco dining. Outside, the opportunity multiplies: an expansive backyard with ample room for a pool, and two existing structures. Main house plus a detached two-car garage. Laying the groundwork for a true compound-style setup, whether that means a futu

When offering please include proof of funds or pre-approval letter. Deposits may be paid via Depositlink or check payable to Compass LLC

Experience the ultimate waterfront lifestyle in this lovely coastal retreat. Perfectly positioned on the edge of Frost Fish Creek, this charming home captures picturesque water views and is thoughtfully designed for effortless indoor-outdoor living. Enjoy direct tidal access to one of Cape Cod's most treasured waterways. Secure a private mooring and launch your kayak, paddleboard, or boat right from your backyard. Meander through scenic Frost Fish Creek into Ryder's Cove and the sparkling waters of Pleasant Bay, where endless opportunities for boating, sailing, fishing, shellfishing, and exploring pristine beaches await. Continue beyond to discover one of New England's most spectacular estuaries and its gateway to the Atlantic Ocean. The expansive rear deck provides the perfect setting for entertaining guests or simply relaxing beneath the stars while taking in the peaceful waterfront setting and ever-changing coastal views. Buyer is responsible for the design and installation of a sep

Brand new shingled style Coastal retreat offers resort style living in sought after North Chatham location. Sited on. 5 of an acre(with pool potential) near beaches and close proximity to town, Chatham Bars Inn and Chatham Seaside Links Golf, this home was curated with luxury and comfort in mind. Exceptional scale, volume and open feel, delivering high end finishes and compelling value at $717 sf. The chef's kitchen features Thermador appliances, quartz surfaces including full height back splash, waterfall island, custom cabinetry with walnut accents, uplighting, coffee station and Butler's pantry. Vaulted ceilings, 8' entry door and first floor doors, two striking limestone fireplaces warm the home's light filled spaces. Finished walk out lower level with wet bar, full bath, bonus room spaces and an 8' slider to bluestone patio and outdoor shower. Certificate of Occupancy in hand, HERS. Rated efficiency, builder and appliance warrantees. 2 Car garage with EV station, 400 amp service,

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

The location that has it all. Walk to both town, fish pier, beach and baseball games. New Farmhouse with pool built by Morgan and Sons and expecting completion by August 1 st. Enjoy Chatham from this 4BR 5.5 bath, 3980 sq foot home. All bedrooms offer spacious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings with large slider with views overlooking the new pool and patio area, airy chef's kitchen and dining area. A detached outer building houses a one car garage and a separate cabana comprised of 252 sf with living room, full bath and wet bar. Terrific entertaining home whether indoors or out

Just 0.4 miles from the sandy shores of Pleasant Street Beach, this enchanting South Chatham Cape-style cottage captures the timeless charm of Cape Cod living. Set down a private lane on a tree-lined lot, this storybook home is filled with warmth and character. The sun-filled interior features an open living and dining area heated by a cozy natural gas stove, a cheerful kitchen with a butcher block island, two inviting bedrooms, one full bath, and an easy single-level floor plan. Step outside to discover your own secluded oasis, where a brick patio, outdoor shower, fire pit tucked beneath the trees, colorful hydrangeas, and raised garden beds create the perfect setting for relaxing and entertaining after a day at the beach. Whether you're searching for a charming year-round residence or a treasured Cape Cod retreat, this special home offers the perfect setting to enjoy everything that defines life in Chatham, from beach days and strolls along Main Street to boutique shopping, waterfron

Located in Chatham’s exclusive Quitnesset neighborhood on Morris Island, between the association’s private deeded beach and the protected trails of Monomoy National Wildlife Refuge, this elegant home captures the essence of Cape Cod living. A sunlit foyer opens to a soaring great room with fireplace and a chef’s kitchen designed for entertaining. The breakfast room overlooks the backyard, while the formal dining room is ideal for gatherings. The first-floor primary suite features a walk-in closet and private bath. An octagonal sunroom and wood-paneled family room with a second fireplace offer inviting spaces to relax. Upstairs are four bedrooms and three full baths, including two en suites, plus a charming hideaway accessed by a spiral staircase. A bonus room offers expansion potential, while the lower level with a full bath provides flexibility. Enjoy a private deck, spacious yard, deeded beach rights, nature trails, and easy access to downtown Chatham

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

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 opportu

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

Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches, Veteran's Field, and the bike path, this three-bedroom, two-bath home offers an exceptional opportunity in a prime Chatham location. Built in 1994, the 1,802 square foot property includes a one-car garage and full basement, providing a strong foundation for your vision. Additional features include wood floors throughout, gas heat, a gas stove, a 150-amp electrical panel, an outdoor shower, and a wood-burning fireplace that adds warmth and character to the main living space. The layout is comfortable and versatile, with spaces ready to be refreshed and reimagined. While the home reflects its original-era finishes, it offers solid bones, exciting potential, and possible pool potential. Buyer are encouraged to conduct independent due diligence and verify all details. A rare opportunity to secure a well-located Chatham address and create something truly special

Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed, 2.5 bath Cape is the essence of Cape Cod style. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas FP & wet bar for relaxed moments overlooking koi pond& garden. The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace & skylit seating area, which flows to the tranquil stone patio for outdoor dining, BBQ. 1st FL primary suite with sitting room and en suite bath. Plus lower level office 300 Sq ft, 2 car garage, AC, generator, gas heat, irrigation. Seller to install new 3 BED septic & new 2nd FL heating/AC system. Adjacent Building lot 20,737 Sq ft available for sale $650,000 PIN #73528- after the house is sold or as a package. 2026 Frost Fish Crk Restoration project for tidal flow in progress

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

Lighthouse beach. A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen and oversized island seamlessly integrate with the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy gas fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. Ascending to the second floor, you'll discover four wonderfully proportioned bedrooms, each offering distant Atlantic Ocean views, and three stylish full baths. The primary suite is a true retreat, boasting glorious views, a spacious walk-in closet, a dressing room, and a

Stage Island is among the most exclusive addresses on Cape Cod — a private 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, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is truly generational. Marsh-front access invites kayaking and quiet recreation, while wildlife and natural beauty frame everyday life. The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light, anchored by a wall of windows and doors with 270-degree views. The private primary suite offers its own deck and a soaking tub with waterfront views — an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks create multiple zones for alfresco dining, yard games, and summers well spent. A setting this rare does not come twice!

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 canopy of trees, the 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 and slider to wraparound deck, with hardwood floors & wood burning fireplace. The good sized kitchen has wet bar & breakfast bar seating, laundry/ pantry area & half bath. The 1 st FL primary Bedroom is en suite with bath. Upstairs are 3 large bedrooms, a full bath, along with ample good closet space. The extra 674 Sq ft finished walk-out lower level is flexible space for Family room or home office with 3rd bath. Nearby is the CC RailTrail access for biking/ walking, Marion's Pie Shop or short drive to Ridgevale Beach. Excellent opportunity for next owner to bring their vision and updates to make it truly shine

Chatham By The Sea. Rare 50-year offering where LOCATION presents a premier opportunity in Chatham. Coveted location 2 blocks to downtown Chatham Village. Chatham Fish Pier, Oyster Pond, Veterans Field, Cow Yard Landing, shopping, groceries, tennis, golf, 1/2 mile away. Spacious one-floor living with room to expand. Ranch home is 1531 square feet and includes 3 bedrooms, large formal living room with fireplace, large kitchen, dining area. The en-suite primary bedroom features a full bathroom with large walk-in shower. There is also a full family bathroom. Poured concrete foundation. 2019 roof, 2017 boiler, and attached oversized 2-bay garage. Central air conditioning, recessed lighting, 4 zone heating system, hardwood flooring. Basement is semi-finished and includes a fireplace, workshop and utility room. Sited beautifully on 3/4 of an acre delivering south, southwest sun exposure. Public water, private sewer. Engineering completed 5/14/26 for a new 3 bedroom traditional Title V septic

Rare opportunity to own a move in ready beach home in Chatham's coveted Ridgevale Beach neighborhood, where homes rarely become available. Just 0.3 miles from Ridgevale Beach, this thoughtfully designed 750+/. Sq. ft. Home blends coastal charm with modern style. The home features 2 bedrooms, 1 bath, plus a versatile area offering additional sleeping space for children or guests. Bright, open living areas and updated finishes make it ideal as a year-round home, vacation retreat, or investment property. Enjoy a spacious patio, dual outdoor showers, and a beautifully landscaped private yard filled with mature plantings and numerous seasonal blooms that includes deeded water rights. Experience the best of Chatham with nearby beaches, the iconic Fourth of July Parade, renowned dining, boutique shopping, and everything that makes this seaside village one of Cape Cod's most sought-after destinations

Lighthouse beach. A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen and oversized island seamlessly integrate with the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy gas fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. Ascending to the second floor, you'll discover four wonderfully proportioned bedrooms, each offering distant Atlantic Ocean views, and three stylish full baths. The primary suite is a true retreat, boasting glorious views, a spacious walk-in closet, a dressing room, and a

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. The seller will install a new septic and hook up to town water

Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates. With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and 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. Home is being offered fully furnished if desired

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. The seller will install a new septic and hook up to town water