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

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 oppor

Built by Eastward Companies in 2013, this thoughtfully designed, turnkey home is located in one of Chatham's highly desirable neighborhoods. Offering over 3,500 sq. ft. of beautifully appointed living space, this Cape features 3 bedrooms and 3.5 baths with an open-concept floor plan that seamlessly blends timeless Cape Cod style with modern conveniences. Filled with natural light, the spacious living room showcases cathedral ceilings and a gas fireplace, and flows effortlessly into the well-appointed kitchen and dining area. The first-floor primary suite offers privacy and comfort, while two generously sized second-floor guest bedrooms and large sitting area provide ample space for family and friends. The fully finished basement includes a beautiful in-home gym with a full bath. Quality craftsmanship is evident throughout, with hardwood floors, high-end finishes and attention to detail. Professionally landscaped grounds create a private outdoor retreat, perfect for gardening, relaxing

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

This house was designed and built by Grattan Gill, a Taliesin Fellow and Frank Lloyd Wright apprentice (1952-57). This distinctive South Chatham home showcases timeless architecture, thoughtful design, and modern comfort. The main level offers the convenience of first-floor living, featuring a spacious primary bedroom, a full bath and direct access to a private balcony overlooking the expansive rear deck-an ideal setting for morning coffee or evening relaxation. The walkout lower level adds exceptional versatility with a second full bathroom, a generous bonus room perfect for guests, a home office, or recreation space, along with a dedicated laundry area and abundant storage. Additional highlights include central air conditioning, a whole-house generator for peace of mind, and a desirable South Chatham location close to beaches, shopping, dining, and all that Cape Cod has to offer. This is a rare opportunity to own a home that blends architectural pedigree with everyday functionality i

This house was designed and built by Grattan Gill, a Taliesin Fellow and Frank Lloyd Wright apprentice (1952-57). This distinctive South Chatham home showcases timeless architecture, thoughtful design, and modern comfort. The main level offers the convenience of first-floor living, featuring a spacious primary bedroom, a full bath and direct access to a private balcony overlooking the expansive rear deck-an ideal setting for morning coffee or evening relaxation. The walkout lower level adds exceptional versatility with a second full bathroom, a generous bonus room perfect for guests, a home office, or recreation space, along with a dedicated laundry area and abundant storage. Additional highlights include central air conditioning, a whole-house generator for peace of mind, and a desirable South Chatham location close to beaches, shopping, dining, and all that Cape Cod has to offer. This is a rare opportunity to own a home that blends architectural pedigree with everyday functionality i

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 3 bedrooms (2 spacious en-suite bedrooms with walk-in closets) and 3 1/2 baths. 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 quality, comfort and a location in one of S

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

TURNKEY! Just open the door to one of Chatham's most desirable neighborhoods, a timeless single-family residence, set on over 40 sq. ft. of manicured land, presents an exceptional opportunity for sophisticated coastal living. This property, maintained in great condition, embodies a refined aesthetic and functional design. The kitchen, thoughtfully designed for both culinary pursuits and social engagement, features stainless steel appliances, stone counters, and a convenient peninsula. Its open-plan configuration seamlessly connects with the living room, enhancing the flow for entertaining, and includes a built-in microwave and a high-end range. The living room serves as a central gathering space, distinguished by a fireplace that provides warmth and ambiance. Integrated built-in shelves offer both display and storage solutions, complementing the rich hardwood flooring that extends throughout. 4 bedrooms, 3.5 baths, and oversized 2 car garage with staircase to loft, a walkout finished b

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat 'On the Loop' in Chatham. This elegant residence showcases exceptional craftsmanship and luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island w/walnut top offers space for casual dining and flows to the dining area. The nearby butler's pantry enjoys a Subzero beverage fridge. The inviting living area w/gas fireplace opens to a 3-season porch and is adjacent to the deck that overlooks conservation. The 1st story primary suite boasts an ensuite bath w/radiant floor heat and walk-in closet. The 2nd story features 2 en-suite bedrooms, family room and home office. Finished lower-level w/9' ceilings, a full bath, and 725 sq ft. Cedar roof, copper downspouts, generator and irrigation by well. With its prime location, its an easy walk to town and th

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 footpri

Tucked away in a private North Chatham setting with deeded rights to Lovers Lake just a short distance away, this extensively renovated 2,000 sq. ft. home offers the ideal blend of comfort, style, and turnkey ease.Thoughtfully updated throughout, the home features a renovated kitchen and bathrooms, air conditioning, and inviting living spaces designed for year-round enjoyment.The main level showcases beautiful wood floors, cathedral ceilings, exposed post-and-beam details and a powder room. The primary suite is located on the second floor with its own private bath and walk-in closet, while the walkout lower level offers two additional bedrooms, a full bathroom, and flexible finished space for family, guests, or a home office. Outdoors, the spacious back deck is large enough for both dining and lounging, making it perfect for summer entertaining or quiet mornings surrounded by nature. With its private setting, extensive renovations, and deeded access to one of Chatham's freshwater ponds

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 and fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room and brick floored vaulted ceiling sun/great room with gas FP and wet bar for relaxed moments overlooking koi pondand garden.The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace and 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 and new 2nd FL heating/AC system. Adjacent Building lot 20,737 Sq ft available $650,000 PIN #73528474 after the house is sold or as a package. 2026 Frost Fish Crk Restoration project for tidal flow in progres

Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels with 2,448 sqft (1,530 sqft finished), the home has been meticulously maintained, with updates including a new roof, central A/C, outdoor shower, renovated primary bath, updated appliances, and more. The main level features a bright living room with a wood-burning fireplace and bay window, an updated kitchen with breakfast bar, and a dining area ideal for entertaining. A spacious primary suite with an updated bath, along with two guest bedrooms and a full bath, complete the level. The lower level adds flexibility with a second living area, garage, laundry, and additional storage. Outside, enjoy a lush lawn, large pa

Nestled at the end of a cul-de-sac and abutting conservation land, this well-maintained 3-bedroom, 1.5-bath ranch offers the ideal combination of privacy and comfort. With 1,476 square feet of living space, this inviting home features wood floors, an open floor plan, and a family room addition with a cathedral ceiling that fills the home with natural light. A formal living room with a wood-burning fireplace provides a warm and welcoming gathering space, while the central air, generator and updated bathrooms add modern conveniences. The bright sunroom overlooks the landscaped yard, creating the perfect spot to enjoy your morning coffee. The walkout lower level offers the potential for additional finished living space. A one-car attached garage completes this property, offering one-level living in a sought-after neighborhood. This Chatham home is ready for your summer enjoyment and Cape Cod memories for years to come

This private oasis in North Chatham, hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean beyond. Quick salt water access to anywhere by boat from your own private beach. A perfect spot for relaxing, entertaining under the sun or stars, and creating lasting memories. This coastal property features panoramic water views, five bedrooms, three baths, and 1850+ square feet of living space to leave as you will or make it your own. Zoning of a 69,000 plus square foot lot in R40 zone allows room for a guest house and a pool with town approvals in addition to the large main house. Buyers and agents should verify all information herein. Floor plans in DOCUMENTS

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

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 3 bedrooms (2 spacious en-suite bedrooms with walk-in closets) and 3 1/2 baths. 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 quality, comfort and a location in one of S

Located on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath shingle-style residence is built for entertaining. The airy first floor features 10' ceilings, a great room with a Rumford fireplace, and a professional kitchen with a wet bar and large island. Luxurious primary suites are found on both floors, while the second story adds an inviting family room and a deck overlooking the Atlantic Ocean and Outer Beach. Two guest suites and a flexible bonus room above the two-car garage offer ample space. Outside, the fenced yard with a bluestone patio and built-in grill provides two ideal sites for a pool and spa. Complete with a whole-house generator and private well irrigation, this home offers exceptional value in the Chatham market

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

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 and fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room and brick floored vaulted ceiling sun/great room with gas FP and wet bar for relaxed moments overlooking koi pondand garden.The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace and 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 and new 2nd FL heating/AC system. Adjacent Building lot 20,737 Sq ft available $650,000 PIN #73528474 after the house is sold or as a package. 2026 Frost Fish Crk Restoration project for tidal flow in progres

Nestled on a picturesque, level parcel accented by tranquil water features, this beautifully maintained four-bedroom, two-bath residence offers an exceptional opportunity to embrace the quintessential Cape Cod lifestyle. Thoughtfully designed for comfortable year-round living and effortless entertainment, the home combines classic charm with modern conveniences in a highly desirable location. The spacious eat-in kitchen features an integrated laundry area and sliding glass doors that open to the private backyard, creating a seamless connection between indoor and outdoor living. The inviting living room is highlighted by gleaming hardwood floors and a gas fireplace, providing a warm and welcoming gathering space after a day spent enjoying nearby beaches and outdoor pursuits. The first floor offers two generously sized bedrooms and a beautifully updated full bath with a custom shower. Upstairs, the impressive primary bedroom showcases cathedral ceilings and exposed beams, creating a brig

Nestled in the charming coastal town of Chatham, this beautifully updated TURN KEY Cape home offers a refined blend of privacy, comfort, and timeless appeal. Set more than 300 feet from Steppingstones Rd. This home is filled with natural light and offers a bright, airy feel throughout. Designed for effortless living and entertaining, the open-concept kitchen and dining area creates a graceful flow at the heart of the home, while the fireplaced living room adds warmth and character. The home features 3 bedrooms, 2.5 baths, a walkout basement, and an inviting layout that feels both elegant and relaxed. Thoughtfully reimagined over the past three years, the property includes a new roof, generator, central air conditioning, new refrigerator and stove, custom-built outdoor shower, patio, irrigation, landscaping, shed, and beautifully refinished hardwood floors. An inviting outdoor deck overlooks the private backyard, creating an ideal setting for quiet mornings or relaxed gatherings. Just m

Tucked away in a private North Chatham setting with deeded rights to Lovers Lake just a short distance away, this extensively renovated 2,000 sq. ft. home offers the ideal blend of comfort, style, and turnkey ease.Thoughtfully updated throughout, the home features a renovated kitchen and bathrooms, air conditioning, and inviting living spaces designed for year-round enjoyment.The main level showcases beautiful wood floors, cathedral ceilings, exposed post-and-beam details and a powder room. The primary suite is located on the second floor with its own private bath and walk-in closet, while the walkout lower level offers two additional bedrooms, a full bathroom, and flexible finished space for family, guests, or a home office. Outdoors, the spacious back deck is large enough for both dining and lounging, making it perfect for summer entertaining or quiet mornings surrounded by nature. With its private setting, extensive renovations, and deeded access to one of Chatham's freshwater ponds

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

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat 'On the Loop' in Chatham. This elegant residence showcases exceptional craftsmanship and luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island w/walnut top offers space for casual dining and flows to the dining area. The nearby butler's pantry enjoys a Subzero beverage fridge. The inviting living area w/gas fireplace opens to a 3-season porch and is adjacent to the deck that overlooks conservation. The 1st story primary suite boasts an ensuite bath w/radiant floor heat and walk-in closet. The 2nd story features 2 en-suite bedrooms, family room and home office. Finished lower-level w/9' ceilings, a full bath, and 725 sq ft. Cedar roof, copper downspouts, generator and irrigation by well. With its prime location, its an easy walk to town and th