9,710

Chatham, MA Homes

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  • /33

    $1,315,000 Sold Oct 21, 2025

    • 1,144 Sq Ft
    • $1,149/SF
    • 177 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1978

    552 Orleans Rd, Chatham, MA 2633

    Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning

    Chris Rhinesmith Compass

    552 Orleans Rd, Chatham, MA 2633
    • /31

      Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,209 Sq Ft

      90 Silver Leaf Ave, Chatham, MA 02633

      90 Silver Leaf Ave, Chatham, MA 02633
  • /71

    $6,395,000

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    101 Morris Island Rd, Chatham, MA 02633

    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

    Jack Bohman Gibson Sotheby's International Realty

    101 Morris Island Rd, Chatham, MA 02633
  • /31

    $1,315,000 Sold Oct 21, 2025

    • 1,144 Sq Ft
    • $1,149/SF
    • 177 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1978

    552 Orleans Rd, North Chatham, MA 02650

    Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning

    Chris Rhinesmith Compass Massachusetts, LLC

    552 Orleans Rd, North Chatham, MA 02650
    • /35

      Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 1,713 Sq Ft

      32 Little Beach Rd, Chatham, MA 02633

      32 Little Beach Rd, Chatham, MA 02633
  • /71

    $4,495,000

    • 4 Beds
    • 5.5 Baths
    • 5,372 Sq Ft

    335 Stage Island Rd, Chatham, MA 02633

    Family-friendly home on Chatham's private Stage Island boasts captivating barrier beach and ocean views. This 10-room, 4-BR, 5.5-bath shingle-style home has 5,372 sf of living space designed for entertaining, indoors and out. The bright and airy 1st floor features a spacious great room with towering windows, a coffered ceiling, and Rumford fireplace. The kitchen boasts top-of-the-line appliances,

    Jack Bohman Gibson Sotheby's International Realty

    335 Stage Island Rd, Chatham, MA 02633
  • /38

    $835,000 Sold Oct 17, 2025

    • 1,144 Sq Ft
    • $730/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1983

    93 Stephen Dr, Chatham, MA 02633

    This quintessential Cape Cod ranch is tucked away in a quiet residential neighborhood south of route 28 with a dedicated path to Ridgevale Beach and is a short drive to Hardings Beach. Just minutes from the West Chatham village center, this home offers the perfect blend of convenience and coastal living. The inviting floor plan of this 3-bedroom, 2-bath home features a warm and welcoming

    Richard Robbins Compass

    93 Stephen Dr, Chatham, MA 02633
    • /53

      Est $2,603,008 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,669 Sq Ft

      16 Windmill Ln, Chatham, MA 02633

      16 Windmill Ln, Chatham, MA 02633
  • /38

    $2,599,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 4 Baths
    • 3,090 Sq Ft

    2 Seapine Rd, North Chatham, MA 02650

    Offered fully furnished, this light-filled contemporary Cape in North Chatham blends coastal elegance with casual sophistication. The main level features a welcoming den, an inviting living room with a fireplace, and a stylish kitchen and dining area that open to a sunny deck, ideal for seamless indoor-outdoor living. The serene first floor primary suite offers comfort and privacy. Upstairs, two

    Jack Bohman Gibson Sotheby's International Realty

    2 Seapine Rd, North Chatham, MA 02650
  • /21

    $855,000 Sold Oct 17, 2025

    • 1,726 Sq Ft
    • $495/SF
    • 154 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    144 Lakeview Ave, Chatham, MA 02633

    SIGNIFICANT PRICE REDUCTION......Three bedroom ranch house in desirable Riverbay Estates. All bedrooms on first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area....Brokers and buyers

    John Burke William Raveis Real Estate & Home Services

    144 Lakeview Ave, Chatham, MA 02633
    • /53

      Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 5,861 Sq Ft

      43 Morris Island Rd, Chatham, MA 02633

      43 Morris Island Rd, Chatham, MA 02633
  • /48

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft

    314 Cockle Cove Rd, Chatham, MA 02659

    Wake up to shimmering views of Nantucket Sound from your luxurious family compound, just steps from Cockle Cove Beach and a sandy stretch off Chatharbor Lane. This rare offering features a newly built main house with three ensuite bedrooms and a separate, gut-renovated one-bedroom cottage for all of your overflow needs. The sundrenched main home boasts spacious, open-concept first-floor living

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    314 Cockle Cove Rd, Chatham, MA 02659
  • /50

    $955,000 Sold Oct 14, 2025

    • 1,340 Sq Ft
    • $713/SF
    • 17 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1981

    67 A Leonard Way, Chatham, MA 02633

    Welcome to 67 A Leonard Way, a charming ranch-style 2-bedroom home tucked away on a quiet street just minutes from downtown Chatham. Inside you'll find a beautifully renovated kitchen with granite countertops, stainless steel appliances and custom cabinetry. The open living and dining areas feature a fireplace, built-in shelving, and hardwood floors, creating a warm and inviting atmosphere. With

    Shane Masaschi Compass

    67 A Leonard Way, Chatham, MA 02633
    • /20

      Est $2,119,264 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,144 Sq Ft

      32 Cranberry Ln, Chatham, MA 02633

      32 Cranberry Ln, Chatham, MA 02633
  • /90

    $4,975,000

    • 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
  • /50

    $995,000 Sold Oct 10, 2025

    • 1,729 Sq Ft
    • $575/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    56 Chatham Crest Dr, Chatham, MA 02633

    Experience classic Cape Cod living in this inviting 3-bedroom, 2-bath Cape, just minutes from Ridgevale Beach, known for its soft sand, gentle surf, and calm waters--perfect for swimming, sunbathing, and relaxing summer days. Set on a generous .35-acre lot, the home features a private backyard ideal for outdoor entertaining or quiet evenings. Inside, the bright and welcoming layout includes a

    Natalia Weiner Gibson Sotheby's International Realty

    56 Chatham Crest Dr, Chatham, MA 02633
    • /45

      Est $3,236,001 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,448 Sq Ft

      48 Salt Marsh Way, North Chatham, MA 02650

      48 Salt Marsh Way, North Chatham, MA 02650
  • /35

    $4,395,000

    • 3 Beds
    • 3 Baths
    • 2,418 Sq Ft

    30 Indian Trail, Chatham, MA 02633

    Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal masterpiece nestled in Hardings Beach Hills with panoramic views of the marsh and creek. Blending classic Cape vernacular with modern inspiration, the home is defined by extraordinary craftsmanship and architectural detail. The open main level features a curved fireplace wall with v-groove paneling that flows into

    Chris Rhinesmith Compass Massachusetts, LLC

    30 Indian Trail, Chatham, MA 02633
  • /95

    $2,025,000 Sold Oct 10, 2025

    • 3,902 Sq Ft
    • $519/SF
    • 64 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2005

    2016 Main St, Chatham, MA 02633

    Stunning Magazine-Quality Home with Resort-Style Living on Main StreetTucked privately off Main Street, this breathtaking home offers the perfect balance of privacy and prime location. Designed for both relaxed living and stylish entertaining, the interior boasts an open floor plan with beautiful shiplap walls, a dedicated dining room with built-in wet bar, and a thoughtfully placed half bath

    Daneen Law Gibson Sotheby's International Realty

    2016 Main St, Chatham, MA 02633
    • /41

      Est $1,644,477 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,205 Sq Ft

      39 Windward Passage, North Chatham, MA 02650

      39 Windward Passage, North Chatham, MA 02650
  • /42

    $3,500,000

    • 3 Beds
    • 4.5 Baths
    • 3,759 Sq Ft

    28 Cranberry Ln, Chatham, MA 02633

    Perfectly sited in sought-after North Chatham, this new construction home is a masterwork of coastal design. The entryway sets a refined tone, opening to a great room with shiplapped and coffered ceilings that create balance and elegance. At one end, a clean-lined kitchen boasts custom cabinetry, a striking quartz island, and premium Thermador and Fisher & Paykel appliances. A dining area flows

    Chris Rhinesmith Compass

    28 Cranberry Ln, Chatham, MA 02633
  • /42

    $4,125,000 Sold Oct 10, 2025

    • 3,808 Sq Ft
    • $1,083/SF
    • 132 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1840

    150 Barcliff Ave, Chatham, MA 02633

    Chatham: where hydrangeas meet the sea and harbors merge into the ocean. A place where cherished memories are created and passed on through generations. If you've been dreaming of living in this storybook town, just a short stroll from sandy beaches and its vibrant Village, you've arrived. Welcome to 150 Barcliff Avenue. Tucked along one of Chatham's most picturesque streets, this updated home

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    150 Barcliff Ave, Chatham, MA 02633
    • /16

      Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 4,581 Sq Ft

      356 Stony Hill Rd, North Chatham, MA 02650

      356 Stony Hill Rd, North Chatham, MA 02650
  • /47

    $3,500,000

    • 3 Beds
    • 4.5 Baths
    • 3,759 Sq Ft

    28 Cranberry Ln, North Chatham, MA 02650

    Perfectly sited in sought-after North Chatham, this new construction home is a masterwork of coastal design. The entryway sets a refined tone, opening to a great room with shiplapped and coffered ceilings that create balance and elegance. At one end, a clean-lined kitchen boasts custom cabinetry, a striking quartz island, and premium Thermador and Fisher & Paykel appliances. A dining area flows

    Chris Rhinesmith Compass Massachusetts, LLC

    28 Cranberry Ln, North Chatham, MA 02650
  • /52

    $1,750,000 Sold Oct 09, 2025

    • 2,366 Sq Ft
    • $740/SF
    • 84 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1971

    10 Pursel Dr, North Chatham, MA 02650

    WATER-VIEW & DEEDED ACCESS TO RYDERS COVE | ''Summer Wind'' - A Coastal Chatham RetreatNestled in one of Chatham's most cherished neighborhoods, ''Summer Wind'' is a timeless Cape Cod escape offering deeded access to Ryders Cove and a private association beach with direct access to Pleasant Bay. Perched gracefully above the water, this serene retreat delivers breathtaking views, impeccable

    Diane Donahue Gibson Sotheby's International Realty

    10 Pursel Dr, North Chatham, MA 02650
    • /40

      Est $1,769,197 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,428 Sq Ft

      98 Orleans Rd, Chatham, MA 02633

      98 Orleans Rd, Chatham, MA 02633
  • /42

    $3,600,000

    • 4 Beds
    • 3.5 Baths
    • 3,899 Sq Ft

    174 Seapine Rd, North Chatham, MA 02650

    Rarely available in Chatham’s coveted Harbor Coves, just steps from the private Association beach, this 4BR, 3.5BA residence has been completely reimagined top to bottom, inside and out. A sweeping circular drive welcomes you home to sunlit vaulted living spaces with high-end finishes that sparkle at every turn. The brand new gourmet kitchen with oversized island flows into a stunning

    Jill Boudreau eXp Realty

    174 Seapine Rd, North Chatham, MA 02650
  • /30

    $1,250,000 Sold Oct 08, 2025

    • 1,179 Sq Ft
    • $1,060/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1963

    141 Marsh View Rd, Chatham, MA 02633

    Welcome to 141 Marsh View Road in the charming Hardings Beach neighborhood of Chatham! This delightful Cape Cod cottage exudes old Cape charm and sits on a desirable corner lot, offering plenty of space for outdoor enjoyment. With 1,179 square feet, this cozy home features 3 bedrooms and one and a half bathrooms making it a perfect retreat or year-round residence.You’ll love the classic touches

    Jessica Metzler Compass

    141 Marsh View Rd, Chatham, MA 02633
    • /30

      Est $1,126,761 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,702 Sq Ft

      6 Palmer Dr, Chatham, MA 02633

      6 Palmer Dr, Chatham, MA 02633
  • /39

    $2,195,000 New Construction

    • 3 Beds
    • 4.5 Baths
    • 3,310 Sq Ft

    98 Horizon Dr, Chatham, MA 02633

    Ready to move-in! New construction and a great value in Chatham with deeded rights to Lover's Lake for swimming, fishing and boating and room for a future pool. Classic Cape Cod home sited high on Great Hills Estates with over 3000 s.f. with 3 BR's and 4.5 baths. Open floor plan offers great room with soaring vaulted ceilings, fireplace and adjacent cook's kitchen with center breakfast island and

    Lori Fanning Smith Compass Massachusetts, LLC

    98 Horizon Dr, Chatham, MA 02633
  • /59

    $1,282,500 Sold Oct 08, 2025

    • 1,661 Sq Ft
    • $772/SF
    • 15 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1850

    591 Crowell Rd, North Chatham, MA 02650

    Chic Meets Historic Charm - Thoughtfully designed, this Cape Cod retreat exudes style and functionality. Featuring 4 bedrooms, and 3 baths, a 2020 renovation by Rick Roy blends rich history with a fresh, modern twist. It's offered turn-key with exquisite designer furnishings down to the top-tier dishes and pots and pans to make your ownership effortless. The layout is flexible, with two private

    Cheryle Young Today Real Estate

    591 Crowell Rd, North Chatham, MA 02650
    • /60

      Est $3,168,969 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,298 Sq Ft

      184 Barcliff Ave, Chatham, MA 02633

      184 Barcliff Ave, Chatham, MA 02633
  • /15

    $675,000 Open Sun 10:30AM - 11:30AM

    • 2 Beds
    • 1 Bath
    • 769 Sq Ft

    39 Meadow Brook Rd, Chatham, MA 02650

    Location! Location! Location! This charming North Chatham gem, remodeled in 2024, offers 768 sq/ft of living space and is located conveniently to the Cape Cod Rail trail, for recreational fun. Enjoy single story living in this 2 bedroom 1 bath home with hardwood floors and a fireplace. There is a 768 sq/ft walkout basement currently used as a single car garage which also has great potential for

    Karin Baxter-King Christie's International Real Estate Atlantic Brokerage

    39 Meadow Brook Rd, Chatham, MA 02650
  • /41

    $825,000 Sold Oct 08, 2025

    • 1,251 Sq Ft
    • $659/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1969

    65 Lantern Ln, South Chatham, MA 02659

    Turnkey investment opportunity in South Chatham! Just .6 miles to Cockle Cove Beach, this classic 3-bedroom, 1-bath ranch offers an unbeatable combination of location, charm, and proven rental performance. South of Route 28, you're moments from the Old Colony Rail Trail, Chatham's seasonal Farmer's Market, and have quick access to the shops, restaurants, and sights of Harwich, Brewster, and

    Erin Copeland Keller Williams Realty

    65 Lantern Ln, South Chatham, MA 02659
    • /53

      Est $2,175,263 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,670 Sq Ft

      390 Old Harbor Rd, Chatham, MA 02633

      390 Old Harbor Rd, Chatham, MA 02633
  • /39

    $11,250,000

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

    558 Fox Hill Rd, Chatham, MA 02633

    Welcome to 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 thoughtful

    Brian Dougherty Corcoran Property Advisors

    558 Fox Hill Rd, Chatham, MA 02633
  • /20

    $1,975,000 Sold Oct 08, 2025

    • 2,770 Sq Ft
    • $713/SF
    • 31 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1970

    20 Hardings Beach Rd, Chatham, MA 02633

    In a coveted Harding's Beach location, this fully renovated Chatham home offers sweeping views of the Sulphur Springs tidal marsh, a spacious yard, and direct sidewalk access to Hardings Beach. Designed for effortless coastal living, the three-level layout features four bedrooms, three and a half baths, and two private primary suites, each with its own en-suite bath. The open-concept main level

    Chris Rhinesmith Compass Massachusetts, LLC

    20 Hardings Beach Rd, Chatham, MA 02633
    • /74

      Est $5,147,491 Not Listed For Sale

      • 5 Beds
      • 6.5 Baths
      • 4,452 Sq Ft

      581 Shore Rd, Chatham, MA 02633

      581 Shore Rd, Chatham, MA 02633
  • /58

    $1,895,000

    • 5 Beds
    • 3 Baths
    • 3,098 Sq Ft

    24 Hillcrest Rd, North Chatham, MA 02650

    Set within one of North Chatham's most coveted enclaves--surrounded by multi-million-dollar homes and moments from the village--this 5-bedroom, 3-bath residence blends timeless Cape charm with outstanding potential. The property enjoys a picturesque corner setting with mature landscaping, perennial gardens, and glimpses of the nearby harbor that hint at its waterview possibilities. Inside,

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    24 Hillcrest Rd, North Chatham, MA 02650
  • /38

    $1,500,000 Sold Oct 03, 2025

    • 1,633 Sq Ft
    • $919/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1963

    17 Bog Way, Chatham, MA 02633

    This contemporary home combines modern design with elevated, sweeping marsh views, just 0.3 miles from Ridgevale Beach. Completely renovated in 2017 with a California-inspired aesthetic, the interiors feature wall-to-wall windows that capture the landscape and provide multiple access points to private decks. The open layout includes a living room with a gas fireplace, dining area, and a sleek

    Chris Rhinesmith Compass

    17 Bog Way, Chatham, MA 02633

Showing Results 41 - 80, Page 2 of 18

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