46

Chatham, MA Homes for Sale

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  • 1761 Main St, Chatham, MA 02633
    1761 Main St, Chatham, MA 02633
    /2

    $619,000

    • Land
    • 1.01 Acres
    • $612,871 per Acre

    1761 Main St, Chatham, MA 02633

    Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

    Agent Photo

    Kimberly Clark

    Bayside Realty Consultants

    (508) 719-6244

    1761 Main St, Chatham, MA 02633
  • 169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    /38

    $5,400,000

    • 5 Beds
    • 4.5 Baths
    • 5,587 Sq Ft

    169 Tisquantum Rd, Chatham, MA 02633

    Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the Cape Cod lifestyle. Situated in the sought-after Quitnesset community, this property is perfect for making lasting memories. Step into a the foyer with a stunning double curved staircase, leading to a vaulted living room with a cozy fireplace and a chef's kitchen designed for entertaining. Enjoy casual meals in the

    Sandra Tanco Kinlin Grover Compass

    169 Tisquantum Rd, Chatham, MA 02633
  • 230 Barcliff Ave, Chatham, MA 02633
    230 Barcliff Ave, Chatham, MA 02633
    230 Barcliff Ave, Chatham, MA 02633
    /10

    $4,525,000 New Construction

    • 4 Beds
    • 6 Baths
    • 5,300 Sq Ft

    230 Barcliff Ave, Chatham, MA 02633

    Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway and anticipating delivery for late June 2026...Architecturally pleasing 4BR 6 bath shingled home with pool will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The

    Lori Fanning Smith Compass Massachusetts, LLC

    230 Barcliff Ave, Chatham, MA 02633
  • 41 Court St, North Chatham, MA 02650
    41 Court St, North Chatham, MA 02650
    41 Court St, North Chatham, MA 02650
    /42

    $2,950,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 3,504 Sq Ft

    41 Court St, North Chatham, MA 02650

    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 & includes extra 20,737 Sq ft building lot. 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

    Phyllis Power Compass

    41 Court St, North Chatham, MA 02650
  • 44 Buena Vista Rd, Chatham, MA 02633
    44 Buena Vista Rd, Chatham, MA 02633
    44 Buena Vista Rd, Chatham, MA 02633
    /76

    $6,900,000

    • 7 Beds
    • 6.5 Baths
    • 6,521 Sq Ft

    44 Buena Vista Rd, Chatham, MA 02633

    Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views,

    Shane Masaschi Compass

    44 Buena Vista Rd, Chatham, MA 02633
  • 20 Jessies Landing, Chatham, MA 2633
    20 Jessies Landing, Chatham, MA 2633
    20 Jessies Landing, Chatham, MA 2633
    /66

    $3,299,900 Open Sat 11AM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    20 Jessies Landing, Chatham, MA 2633

    Welcome to this beautifully crafted residence in Jessie's Landing, an exclusive Eastward Companies development, ideally located just a short walk to Harding's Beach. Set on nearly a half-acre and outside the flood zone, this thoughtfully designed home offers the perfect blend of Cape Cod charm, modern comfort, and peace of mind. The open floor plan is ideal for everyday living and entertaining,

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    20 Jessies Landing, Chatham, MA 2633
  • 92 Indian Trail, Chatham, MA 02633
    92 Indian Trail, Chatham, MA 02633
    92 Indian Trail, Chatham, MA 02633
    /34

    $3,200,000

    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    92 Indian Trail, Chatham, MA 02633

    Professional photos coming soon! Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living. This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted

    Judith Smith John C Ricotta & Assoc.

    92 Indian Trail, Chatham, MA 02633
  • 85 Cedar St, Chatham, MA 02633
    85 Cedar St, Chatham, MA 02633
    85 Cedar St, Chatham, MA 02633
    /90

    $4,700,000

    • 5 Beds
    • 3.5 Baths
    • 3,080 Sq Ft

    85 Cedar St, Chatham, MA 02633

    ** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms--four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room

    Tim Bailey John C Ricotta & Assoc.

    85 Cedar St, Chatham, MA 02633
  • 238 Cranberry Ln, Chatham, MA 02633
    238 Cranberry Ln, Chatham, MA 02633
    238 Cranberry Ln, Chatham, MA 02633
    /36

    $6,800,000

    • 5 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    238 Cranberry Ln, Chatham, MA 02633

    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, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, Chatham, MA 02633
  • 287 Cedar St, Chatham, MA 02633
    287 Cedar St, Chatham, MA 02633
    287 Cedar St, Chatham, MA 02633
    /63

    $3,850,000

    • 3 Beds
    • 4.5 Baths
    • 3,640 Sq Ft

    287 Cedar St, Chatham, MA 02633

    NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & 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

    Shane Masaschi Compass

    287 Cedar St, Chatham, MA 02633
  • 78 Indian Trail, Chatham, MA 02633
    78 Indian Trail, Chatham, MA 02633
    78 Indian Trail, Chatham, MA 02633
    /35

    $2,800,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    78 Indian Trail, Chatham, MA 02633

    Professional photos coming soon!Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in beautiful water views and unforgettable sunsets, with private stairs leading down to the water's edge of Bucks Creek

    Judith Smith John C Ricotta & Assoc.

    78 Indian Trail, Chatham, MA 02633
  • 83 Old Mail Rd, North Chatham, MA 02650
    83 Old Mail Rd, North Chatham, MA 02650
    83 Old Mail Rd, North Chatham, MA 02650
    /42

    $3,795,000

    • 3 Beds
    • 4.5 Baths
    • 5,154 Sq Ft

    83 Old Mail Rd, North Chatham, MA 02650

    NEW CONSTRUCTION - NORTH CHATHAM, 02650. Zillow’s February 2026 data showed just 6 homes for sale in the coveted 02650 North Chatham market, with 50% higher average home values at $1,933,566, compared to 29 homes for sale and a 50% lower average home value of $1,282,193 in 02633. As someone who lives and works in Chatham, I can tell you this kind of difference matters. Buyers at the luxury level

    Shane Masaschi Compass

    83 Old Mail Rd, North Chatham, MA 02650
  • 2386 Main St, South Chatham, MA 02659
    2386 Main St, South Chatham, MA 02659
    2386 Main St, South Chatham, MA 02659
    /4

    $315,000

    • Land
    • 1.07 Acres
    • $294,393 per Acre

    2386 Main St, South Chatham, MA 02659

    This 1.069 acre lot is zoned R20 and partially R60. Great location close to the beach and bike trail. Buyer and their agent to do their own due diligence. Please verify all information contained herein.

    Judith Smith John C Ricotta & Assoc.

    2386 Main St, South Chatham, MA 02659
  • 66 Ethelma Dr, Chatham, MA 02633
    66 Ethelma Dr, Chatham, MA 02633
    66 Ethelma Dr, Chatham, MA 02633
    /23

    $949,000

    • 4 Beds
    • 1 Bath
    • 1,547 Sq Ft

    66 Ethelma Dr, Chatham, MA 02633

    66 Ethelma Drive is a rare pond front opportunity in Chatham, MA, set along the shores of Emery Pond just minutes from downtown Chatham, Cape Cod beaches, restaurants, shops and close to the bike path. This 4-bedroom, 1-bath home offers 1,547 sq ft on approximately half an acre and presents exceptional potential for renovation, reconstruction, or a custom waterfront build. For buyers seeking

    Shane Masaschi Compass

    66 Ethelma Dr, Chatham, MA 02633
  • 118 Wilfred Rd, Chatham, MA 02633
    118 Wilfred Rd, Chatham, MA 02633
    118 Wilfred Rd, Chatham, MA 02633
    /50

    $1,200,000

    • 3 Beds
    • 3 Baths
    • 1,804 Sq Ft

    118 Wilfred Rd, Chatham, MA 02633

    Welcome to 118 Wilfred Road, a charming Cape-style home tucked into one of Chatham's beloved ponds settings. With 3 bedrooms, 3 baths, and 1,804 square feet, this inviting residence captures the essence of relaxed Cape Cod living. Enjoy sweeping views of Black Pond, White Pond and Emery Pond and take advantage of an exceptional location less than 0.2 miles from White Pond, a cherished freshwater

    Shane Masaschi Compass

    118 Wilfred Rd, Chatham, MA 02633
  • 425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    /25

    $450,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    425 Main St Unit D, Chatham, MA 02633

    Nestled above Bumbula “It’s All About Me,” Unit D at 425 Main Street offers a rare blend of privacy, comfort, and true in-town living. One of only two residences on the second floor, it features a discreet private entrance and an open, light-filled layout with recent upgrades, including luxury vinyl flooring and refreshed finishes. The well-appointed kitchen flows into a spacious living and

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • 243 Crowell Rd, Chatham, MA 02633
    243 Crowell Rd, Chatham, MA 02633
    243 Crowell Rd, Chatham, MA 02633
    /48

    $1,350,000

    • 3 Beds
    • 1.5 Baths
    • 2,278 Sq Ft

    243 Crowell Rd, Chatham, MA 02633

    Comfortable Cape style 3 bedroom home set back from the road, close to down-town Chatham Village, Oyster Pond Beach and exceptional dining. Updated kitchen, A/C splits, fenced, sunny back yard with deck. Free standing 2 car garage on over .6 acre lot. Expansion potential in the unfinished second floor and basement areas.

    Michael Hall William Raveis Real Estate & Home Services

    243 Crowell Rd, Chatham, MA 02633
  • 301 Whidah Rd, North Chatham, MA 2650
    301 Whidah Rd, North Chatham, MA 2650
    301 Whidah Rd, North Chatham, MA 2650
    /52

    $12,950,000

    • 5 Beds
    • 6.5 Baths
    • 7,259 Sq Ft

    301 Whidah Rd, North Chatham, MA 2650

    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

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, North Chatham, MA 2650
  • 301 Whidah Rd, Chatham, MA 02650
    301 Whidah Rd, Chatham, MA 02650
    301 Whidah Rd, Chatham, MA 02650
    /42

    $12,950,000

    • 5 Beds
    • 6.5 Baths
    • 7,259 Sq Ft

    301 Whidah Rd, Chatham, MA 02650

    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 views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, Chatham, MA 02650
  • 137 Shane Dr, Chatham, MA 02633
    137 Shane Dr, Chatham, MA 02633
    137 Shane Dr, Chatham, MA 02633
    /49

    $1,495,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    137 Shane Dr, Chatham, MA 02633

    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 iconic landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels of living, the

    Tom Riley Compass Massachusetts, LLC

    137 Shane Dr, Chatham, MA 02633
  • 246 Stage Island Rd, Chatham, MA 02633
    246 Stage Island Rd, Chatham, MA 02633
    246 Stage Island Rd, Chatham, MA 02633
    /37

    $7,999,000

    • 4 Beds
    • 6 Baths
    • 4,735 Sq Ft

    246 Stage Island Rd, Chatham, MA 02633

    Set on nearly an acre with commanding views of Stage Harbor, this Stage Island residence combines timeless elegance with modern comfort. The foyer opens to a dramatic living room framed by expansive windows and a stylish kitchen with an island and dining area that extends to a generous deck—perfect for entertaining. The main level also offers a private ensuite bedroom, den, and laundry. Upstairs

    Chris Rhinesmith Compass

    246 Stage Island Rd, Chatham, MA 02633
  • 558 Fox Hill Rd, Chatham, MA 02633
    558 Fox Hill Rd, Chatham, MA 02633
    558 Fox Hill Rd, Chatham, MA 02633
    /39

    $1,469,000

    • 5 Beds
    • 10 Baths
    • 11,000 Sq Ft

    558 Fox Hill Rd, Chatham, MA 02633

    Co-ownership opportunity. Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a

    Brian Dougherty Corcoran Property Advisors

    558 Fox Hill Rd, Chatham, MA 02633
  • 39 Jedidiah Way, Chatham, MA 02633
    39 Jedidiah Way, Chatham, MA 02633
    39 Jedidiah Way, Chatham, MA 02633
    /50

    $1,650,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,810 Sq Ft

    39 Jedidiah Way, Chatham, MA 02633

    39 Jedidiah Way, has been gently utilized by the same family for the past 29 years, serving as a reliable summer retreat. Situated on a .5-acre elevated lot overlooking a wooded cul-de-sac, this property boasts direct access to the Old Colony Rail Trail, a unique feature among current Chatham offerings. Enjoy the convenience of being just 1 mile from Nantucket Sound Beaches or capitalize on the

    Tom Jones Berkshire Hathaway HomeServices Robert Paul Properties

    39 Jedidiah Way, Chatham, MA 02633
  • 28 Lakeview Ave, Chatham, MA 02633
    28 Lakeview Ave, Chatham, MA 02633
    28 Lakeview Ave, Chatham, MA 02633
    /63

    $1,495,000

    • 3 Beds
    • 2.5 Baths
    • 2,441 Sq Ft

    28 Lakeview Ave, Chatham, MA 02633

    Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated with hardwood throughout, this 3 bedroom, 2.5 bath home offers a comfortable floor plan including a first floor primary ensuite bedroom and 2 large guest bedooms and bath on the second level. In addition to the inviting living room and dining room, adjacent to well apppointed eat-in kitchen, the den with

    Ella Leavitt Compass

    28 Lakeview Ave, Chatham, MA 02633
  • 7 Cove Rd, Chatham, MA 02650
    7 Cove Rd, Chatham, MA 02650
    7 Cove Rd, Chatham, MA 02650
    /9

    $5,750,000

    • 3 Beds
    • 6 Baths
    • 4,902 Sq Ft

    7 Cove Rd, Chatham, MA 02650

    Tucked within a coveted North Chatham setting of Harbor Coves and offering access to a private association beach, this exceptional Gambrel-style residence currently under construction with Harbor Builders presents a sophisticated coastal retreat.The property offers generous indoor and outdoor living spaces on a half an acre. The main level features an inviting open floor plan where a

    Chris Rhinesmith Compass Massachusetts, LLC

    7 Cove Rd, Chatham, MA 02650
  • 46 Chippingstone Rd, Chatham, MA 02633
    46 Chippingstone Rd, Chatham, MA 02633
    46 Chippingstone Rd, Chatham, MA 02633
    /35

    $919,000

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft

    46 Chippingstone Rd, Chatham, MA 02633

    Riverbay, Chatham... True One Level living with Garage/parking on home level. 8 room custom built ranch with side loading garages, high profile roofline, integrated front porch. Inside, abundant common areas and living space. entrance hallway opens to the living and dining rooms, and two hallways leading to the 3 bedrooms. At the back of the home- 3 additional rooms: a fireplaced family room, an

    Derek Greene The Greene Realty Group

    46 Chippingstone Rd, Chatham, MA 02633
  • 33 Crowell Rd, Chatham, MA 02633
    33 Crowell Rd, Chatham, MA 02633
    33 Crowell Rd, Chatham, MA 02633
    /10

    $4,499,900 New Construction

    • 3 Beds
    • 7 Baths
    • 5,820 Sq Ft

    33 Crowell Rd, Chatham, MA 02633

    A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    33 Crowell Rd, Chatham, MA 02633
  • 231 Crowell Rd, Chatham, MA 2633
    231 Crowell Rd, Chatham, MA 2633
    231 Crowell Rd, Chatham, MA 2633
    /27

    $1,650,000

    • 1 Bath
    • 2,586 Sq Ft

    231 Crowell Rd, Chatham, MA 2633

    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

    Judith Smith John C. Ricotta & Associates, Inc.

    231 Crowell Rd, Chatham, MA 2633
  • 50 Eldredge Square S, Chatham, MA 02633
    50 Eldredge Square S, Chatham, MA 02633
    50 Eldredge Square S, Chatham, MA 02633
    /23

    $1,995,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    50 Eldredge Square S, Chatham, MA 02633

    Ideally situated just moments from Chatham's Village boutiques and restaurants, this exceptional three bedroom,two bath residence captures the essence of Chatham coastal living. Privately set on a private dead-end street, the property offers tranquility and also convenience in one of Chatham's most desirable settings. Thoughtfully designed for effortless single-level living, the main floor

    Chris Rhinesmith Compass Massachusetts, LLC

    50 Eldredge Square S, Chatham, MA 02633
  • 346 Morris Island Rd, Chatham, MA 02633
    346 Morris Island Rd, Chatham, MA 02633
    346 Morris Island Rd, Chatham, MA 02633
    /33

    $4,500,000

    • 4 Beds
    • 3.5 Baths
    • 2,850 Sq Ft

    346 Morris Island Rd, Chatham, MA 02633

    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

    Chris Rhinesmith Compass Massachusetts, LLC

    346 Morris Island Rd, Chatham, MA 02633
  • 1114 Orleans Rd Unit 2, North Chatham, MA 02650
    1114 Orleans Rd Unit 2, North Chatham, MA 02650
    1114 Orleans Rd Unit 2, North Chatham, MA 02650
    /37

    $1,425,000

    • 2 Beds
    • 3 Baths
    • 2,212 Sq Ft

    1114 Orleans Rd Unit 2, North Chatham, MA 02650

    Part of the historic Christopher Ryder House, this elegant two-bedroom, three bath condominium blends one floor living with timeless architectural charm. The residence offers beautifully proportioned rooms, high ceilings, large sun-filled windows, and warm wood floors throughout. A gracious foyer opens to a grand living room with gas fireplace that flows seamlessly into the dining room and

    Chris Rhinesmith Compass Massachusetts, LLC

    1114 Orleans Rd Unit 2, North Chatham, MA 02650
  • 425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    /25

    $450,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    425 Main St Unit D, Chatham, MA 02633

    Nestled above Bumbula ''It's All About Me,'' Unit D at 425 Main Street offers an exceptional blend of privacy, comfort, and in-town convenience. This updated 1-bedroom, 1-bath residence is one of only two homes on the second floor, accessed by a discreet private entrance that enhances its quiet, retreat-like feel. Inside, an open-concept layout is filled with natural light and features recent

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • 2548 Main St, South Chatham, MA 2659
    2548 Main St, South Chatham, MA 2659
    /2

    $3,999,900 New Construction

    • 4 Beds
    • 5.5 Baths
    • 4,942 Sq Ft

    2548 Main St, South Chatham, MA 2659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes at this stage with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyers. Incorporating expansive open living space you will enjoy entertaining family

    Ward Brown William Raveis Real Estate & Home Services

    2548 Main St, South Chatham, MA 2659
  • 49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    /36

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    49 Duck Marsh Ln, Chatham, MA 02633

    Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

    Tim Bailey John C Ricotta & Assoc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • 99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    /44

    $5,495,000

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    99 Uncle Alberts Drive Extension, Chatham, MA 2633

    Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

    Shane Masaschi Compass

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • 32 Tip Cart Dr, Chatham, MA 02633
    32 Tip Cart Dr, Chatham, MA 02633
    32 Tip Cart Dr, Chatham, MA 02633
    /34

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,802 Sq Ft

    32 Tip Cart Dr, Chatham, MA 02633

    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

    Shane Masaschi Compass

    32 Tip Cart Dr, Chatham, MA 02633
  • 104 Seapine Rd, North Chatham, MA 02650
    104 Seapine Rd, North Chatham, MA 02650
    104 Seapine Rd, North Chatham, MA 02650
    /36

    $2,650,000

    • 3 Beds
    • 2.5 Baths
    • 2,969 Sq Ft

    104 Seapine Rd, North Chatham, MA 02650

    Optimally sited on the lot to maximize views of Crows Pond from every room, this 3-bedroom 2.5-bath home is just steps away from the private Harbor Coves Association beach & ready to make your Chatham dreams come true. The first floor of this custom-built home features multiple living areas perfect for entertaining company or enjoying the peace of all four seasons in Chatham. With hardwood floors

    Kristin Muller John C Ricotta & Assoc.

    104 Seapine Rd, North Chatham, MA 02650
  • 2550 Main St, South Chatham, MA 02659
    2550 Main St, South Chatham, MA 02659
    /2

    $3,999,900 New Construction

    • 3 Beds
    • 4.5 Baths
    • 4,393 Sq Ft

    2550 Main St, South Chatham, MA 02659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes and extras at this stage of construction with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyer. Incorporating expansive open living space you will

    Ward Brown William Raveis Real Estate & Home Services

    2550 Main St, South Chatham, MA 02659
  • 1114 Orleans Rd Unit 2, Chatham, MA 2633
    1114 Orleans Rd Unit 2, Chatham, MA 2633
    1114 Orleans Rd Unit 2, Chatham, MA 2633
    /38

    $1,425,000

    • 2 Beds
    • 3 Baths
    • 2,212 Sq Ft

    1114 Orleans Rd Unit 2, Chatham, MA 2633

    This two-bedroom, three bath condominium, part of the historic Christopher Ryder House, blends timeless architecture with elegant design. The residence features high ceilings, wood floors, large windows, and generously scaled rooms. The foyer opens to a grand living room with gas fireplace flowing into the dining area and adjoining pantry, with views into the chef’s kitchen featuring a Thermador

    Chris Rhinesmith Compass

    1114 Orleans Rd Unit 2, Chatham, MA 2633
  • 912 Main St Unit 308, Chatham, MA 02633
    912 Main St Unit 308, Chatham, MA 02633
    912 Main St Unit 308, Chatham, MA 02633
    /65

    $459,000

    • 1 Bed
    • 2 Baths
    • 1,284 Sq Ft

    912 Main St Unit 308, Chatham, MA 02633

    Park Place is the Premiere Chatham address for an easy-care, maintenance-free lifestyle! These apartment-style condos cater to age 62+ residents seeking to enjoy a walkable location in Town, numerous opportunities for social engagement (including daily continental breakfast and Friday night cocktails), an exercise room, library, guest suite, garage parking, elevator and more. Unit 308 is located

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    912 Main St Unit 308, Chatham, MA 02633

Showing Results 1 - 40, Page 1 of 2

Massachusetts Barnstable County Chatham

Real Estate & Homes for Sale in Chatham, MA

Frequently Asked Questions

Is Chatham, MA a safe city?
In general, the safest neighborhoods in Chatham, MA with lower crime scores are Chatham Village, North Chatham, West Chatham and South Chatham.
What are the most popular zip codes in Chatham, MA?
The most popular zip codes in Chatham, MA include 02633, 02659, 02645, 02646 and 02650.
What are the most popular neighborhoods near Chatham, MA?
The most popular neighborhoods near Chatham, MA are Chatham Village, West Chatham, South Chatham, Harwich Port and North Chatham.
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