74

Chatham, MA Homes for Sale

Section Image Section Image
  • 99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    /24

    $5,900,000

    • 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

    Agent Photo

    Shane Masaschi

    Compass

    (508) 400-2035

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • 44 Buena Vista Rd, Chatham, MA 02633
    44 Buena Vista Rd, Chatham, MA 02633
    44 Buena Vista Rd, Chatham, MA 02633
    /42

    $7,900,000

    • 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,

    Agent Photo

    Shane Masaschi

    Compass

    (508) 501-9618

    44 Buena Vista Rd, Chatham, MA 02633
  • 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
  • 55 Winterset Dr, Chatham, MA 02633
    55 Winterset Dr, Chatham, MA 02633
    55 Winterset Dr, Chatham, MA 02633
    /74

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 4,072 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

    Agent Photo

    Tara Schiffmann Brown

    Bayview Real Estate

    (508) 388-5284

    55 Winterset Dr, Chatham, MA 02633
  • 287 Cedar St, Chatham, MA 02633
    287 Cedar St, Chatham, MA 02633
    287 Cedar St, Chatham, MA 02633
    /69

    $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

    Agent Photo

    Shane Masaschi

    Compass

    (508) 952-9486

    287 Cedar St, Chatham, MA 02633
  • 0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    /6

    $250,000

    • Land
    • 0.72 Acre
    • $347,222 per Acre

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633

    Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

    Agent Photo

    Shane Masaschi

    Compass

    (508) 691-8324

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
  • 47 Cranberry Way, South Chatham, MA 2659
    47 Cranberry Way, South Chatham, MA 2659
    47 Cranberry Way, South Chatham, MA 2659
    /32

    $799,900

    • 2 Beds
    • 2 Baths
    • 868 Sq Ft

    47 Cranberry Way, South Chatham, MA 2659

    Tucked away on a picturesque side street off Cockle Cove Road in Chatham, this delightful 2-bedroom, 2-bath home is full of coastal charm.Step through the front door into a warm, inviting living room complete with wood floors and a cozy fireplace -- perfect for relaxing evenings. Just off the living area, there's space for a dining nook, while the kitchen sits at the back of the home, offering

    Agent Photo

    William Raye

    Gibson Sotheby's International Realty

    (508) 432-7856

    47 Cranberry Way, South Chatham, MA 2659
  • 47 Cranberry Way, Chatham, MA 02659
    47 Cranberry Way, Chatham, MA 02659
    47 Cranberry Way, Chatham, MA 02659
    /34

    $799,900

    • 2 Beds
    • 2 Baths
    • 868 Sq Ft

    47 Cranberry Way, Chatham, MA 02659

    Charming Coastal Retreat...Tucked away on a picturesque side street off Cockle Cove Road, this delightful 2-bedroom, 2-bath home is full of coastal charm! Step through the front door and into a warm, inviting living room complete with wood floors and a cozy fireplace — perfect for relaxing evenings. Just off the living area, there's space for a dining nook, while the well-appointed kitchen sits

    Agent Photo

    William Raye

    Gibson Sotheby's International Realty

    (508) 290-7066

    47 Cranberry Way, Chatham, MA 02659
  • 93 Bucks Creek Rd, Chatham, MA 02633
    93 Bucks Creek Rd, Chatham, MA 02633
    93 Bucks Creek Rd, Chatham, MA 02633
    /55

    $3,200,000

    • 3 Beds
    • 3.5 Baths
    • 3,544 Sq Ft

    93 Bucks Creek Rd, Chatham, MA 02633

    Welcome to 93 Bucks Creek Rd, where luxury meets coastal elegance. This architecturally stunning, custom-built home offers an unparalleled resort-style experience boasting a heated, saltwater pool and membership to the exclusive Hardings Hills Association, featuring a private dock, kayak storage, & picnic area. Nestled just 3/10ths of a mile from the pristine sands of Hardings Beach, this

    Agent Photo

    Shane Masaschi

    Compass

    (508) 571-0968

    93 Bucks Creek Rd, Chatham, MA 02633
  • 346 Morris Island Rd, Chatham, MA 02633
    346 Morris Island Rd, Chatham, MA 02633
    346 Morris Island Rd, Chatham, MA 02633
    /81

    $4,900,000

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

    346 Morris Island Rd, Chatham, MA 02633

    Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vista out to Nantucket Sound and beyond. This four bedroom, 4.5 bath residence blends exquisite taste with timeless coastal elegance. Thoughtfully renovated, the home is designed to showcase wide, sweeping views of the harbor from nearly every room. Light-filled interiors pair refined finishes with a relaxed

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    (508) 401-8501

    346 Morris Island Rd, Chatham, MA 02633
  • 48 Sylvan Way, South Chatham, MA 02659
    48 Sylvan Way, South Chatham, MA 02659
    48 Sylvan Way, South Chatham, MA 02659
    /50

    $5,495,000

    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    The first of two homes in a private, gated South Chatham enclave retreated off Main Street and bound in the rear by over 550' of Chatham Bike Trail. The first home is an uncommonly stylish 5700 +/- SF destination home designed for generational use and comfort situated on a magnificent piece of land with numerous recreational possibilities (see proposed tennis/ pickleball location), direct private

    Agent Photo

    Chris Olson

    eXp Realty, LLC

    (508) 715-6571

    48 Sylvan Way, South Chatham, MA 02659
  • 335 Stage Island Rd, Chatham, MA 02633
    335 Stage Island Rd, Chatham, MA 02633
    335 Stage Island 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
  • 101 Morris Island Rd, Chatham, MA 02633
    101 Morris Island Rd, Chatham, MA 02633
    101 Morris Island Rd, 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
  • 2 Seapine Rd, North Chatham, MA 02650
    2 Seapine Rd, North Chatham, MA 02650
    2 Seapine Rd, North Chatham, MA 02650
    /38

    $2,599,000

    • 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
  • 314 Cockle Cove Rd, Chatham, MA 02659
    314 Cockle Cove Rd, Chatham, MA 02659
    314 Cockle Cove Rd, Chatham, MA 02659
    /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
  • 85 Cedar St, Chatham, MA 02633
    85 Cedar St, Chatham, MA 02633
    85 Cedar St, 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
  • 30 Indian Trail, Chatham, MA 02633
    30 Indian Trail, Chatham, MA 02633
    30 Indian Trail, Chatham, MA 02633
    /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
  • 28 Cranberry Ln, Chatham, MA 02633
    28 Cranberry Ln, Chatham, MA 02633
    28 Cranberry Ln, Chatham, MA 02633
    /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
  • 28 Cranberry Ln, North Chatham, MA 02650
    28 Cranberry Ln, North Chatham, MA 02650
    28 Cranberry Ln, 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
  • 86 Champlain Rd, Chatham, MA 02633
    86 Champlain Rd, Chatham, MA 02633
    86 Champlain Rd, Chatham, MA 02633
    /49

    $3,200,000

    • 3 Beds
    • 4.5 Baths
    • 4,361 Sq Ft

    86 Champlain Rd, Chatham, MA 02633

    Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lighthouse and Nantucket Sound. Savor the warm summer breezes from this 3 BR, 4.5 Bath, 4,361 sf home with a private deeded footpath to the sandy shores of Stage Harbor. Thoughtfully designed to capture harbor and wetland views, the house features vaulted ceilings, an abundance of windows, hardwood floors and an

    Jack Bohman Gibson Sotheby's International Realty

    86 Champlain Rd, Chatham, MA 02633
  • 39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    /15

    $675,000 Open Sat 11AM - 1PM

    • 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
  • 558 Fox Hill Rd, Chatham, MA 02633
    558 Fox Hill Rd, Chatham, MA 02633
    558 Fox Hill 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
  • 24 Hillcrest Rd, North Chatham, MA 02650
    24 Hillcrest Rd, North Chatham, MA 02650
    24 Hillcrest Rd, North Chatham, MA 02650
    /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
  • 425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    425 Main St Unit D, Chatham, MA 02633
    /17

    $495,000

    • 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 unparalleled lifestyle in the heart of Chatham. This 1-bedroom, 1-bathroom residence blends sophisticated comfort with modern convenience, making it the ideal year-round home or refined retreat. With a private, discreet entrance, this second-floor sanctuary is one of only two residences on this level.Designed for

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • 99 A Leonard Way, Chatham, MA 02633
    99 A Leonard Way, Chatham, MA 02633
    99 A Leonard Way, Chatham, MA 02633
    /6

    $850,000

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    99 A Leonard Way, Chatham, MA 02633

    Living the Cape Cod Dream: Relocating to ChathamHave you ever dreamed of waking up to salty sea air, scenic harbor views, and small-town charm? If so, relocating to Chatham, Massachusetts might just be the lifestyle upgrade you’ve been searching for. Nestled on the elbow of Cape Cod, Chatham blends coastal beauty with historic character, offering residents a unique mix of peace, recreation, and

    Terry Hayes The Paladin Group, LLC

    99 A Leonard Way, Chatham, MA 02633
  • 39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    /13

    $699,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    39 Meadow Brook Rd, Chatham, MA 02650

    Significant Price Reduction- don't miss your opportunity!! Come see this delightful 2 bed/1 bath gem! It has been thoughtfully updated making it move-in ready while still offering tons of potential for all your personal touches. Nestled in a prime location on a quiet street, you'll be just steps from the bike path, conservation paths, school, pickleball courts, sidewalks to town- ideal for anyone

    Beth Ryan Compass

    39 Meadow Brook Rd, Chatham, MA 02650
  • 109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    /26

    $399,000

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

    Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal gateway to the Chatham lifestyle. This second-floor 1-bedroom, 1-bathroom condominium is a rare find, blending convenience, charm, and investment potential. Whether you're seeking a turnkey rental, seasonal getaway, or an easy-care year-round home, this residence delivers on every front. Inside, the unit is

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln 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
    /17

    $495,000

    • 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 unparalleled lifestyle in the heart of Chatham. This 1-bedroom, 1-bathroom residence blends sophisticated comfort with modern convenience, making it the ideal year-round home or refined retreat. With a private, discreet entrance, this second-floor sanctuary is one of only two residences on this level.Designed for

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • 109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
    /30

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650

    Tucked away on a quiet street in the heart of North Chatham, this second-floor condominium offers a rare opportunity to own in one of Cape Cod's most coveted locations. Perfect as a seasonal retreat, investment property, or smart entry into the Chatham market, it blends convenience and charm. Sunlight fills the welcoming interior, highlighting hardwood floors, a cozy wood-burning fireplace, and

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
  • 32 Sunset Ln, Chatham, MA 02633
    32 Sunset Ln, Chatham, MA 02633
    32 Sunset Ln, Chatham, MA 02633
    /77

    $1,995,000

    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    32 Sunset Ln, Chatham, MA 02633

    Extremely rare opportunity! Available for the first time in 60+ years, this property is tucked away on a quiet lane in Chatham's coveted Old Village. The location offers the best of both worlds -- peaceful surroundings with easy access to Chatham's most beloved spots. Take the neighborhood path around Little Mill Pond for your morning coffee downtown, spend the day at Lighthouse Beach, launch a

    Tom Riley Compass Massachusetts, LLC

    32 Sunset Ln, Chatham, MA 02633
  • 20 Cedar Swamp Ln, Chatham, MA 02633
    20 Cedar Swamp Ln, Chatham, MA 02633
    20 Cedar Swamp Ln, Chatham, MA 02633
    /11

    $995,000

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft

    20 Cedar Swamp Ln, Chatham, MA 02633

    Discover the essence of Cape Cod living at this waterfront retreat on Stage Harbor. Tucked away on a quiet lane yet close to Chatham Village, the property offers sweeping views with ever-changing tidal scenery, birdlife, and spectacular sunsets. The home features a welcoming coastal vibe with sun-filled living spaces, while outdoor areas are ideal for entertaining or quiet reflection. A firepit

    Ellen Valentgas Sotheby's International Realty

    20 Cedar Swamp Ln, Chatham, MA 02633
  • 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
  • 27 Martha Kendrick Dr, Chatham, MA 02633
    27 Martha Kendrick Dr, Chatham, MA 02633
    27 Martha Kendrick Dr, Chatham, MA 02633
    /42

    $1,200,000

    • 3 Beds
    • 2.5 Baths
    • 2,179 Sq Ft

    27 Martha Kendrick Dr, Chatham, MA 02633

    Welcome to this delightful 3-bedroom, 2.5-bath Cape-style home nestled just moments from the heart of downtown Chatham. With its classic architecture and thoughtful layout, this property offers the perfect blend of coastal charm and modern convenience.Step inside to discover sun-drenched living spaces with abundant natural light and a cozy fireplace that anchors the main living area. The

    Kathy Doyle Gibson Sotheby's International Realty

    27 Martha Kendrick 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
    /47

    $7,999,000

    • 4 Beds
    • 6 Baths
    • 4,717 Sq Ft

    246 Stage Island Rd, Chatham, MA 02633

    Set on nearly an acre in one of Chatham's most coveted enclaves, this Stage Island residence offers an extraordinary combination of refined craftsmanship and sweeping Stage Harbor views. The welcoming foyer opens to a dramatic living room with walls of glass framing the water, filling the space with natural light. A stylish kitchen with center island and dining area extends to an expansive deck,

    Chris Rhinesmith Compass Massachusetts, LLC

    246 Stage Island Rd, Chatham, MA 02633
  • 19 Captain Richards Way Unit 1, Chatham, MA 02633
    19 Captain Richards Way Unit 1, Chatham, MA 02633
    19 Captain Richards Way Unit 1, Chatham, MA 02633
    /28

    $489,000

    • 2 Beds
    • 1.5 Baths
    • 576 Sq Ft

    19 Captain Richards Way Unit 1, Chatham, MA 02633

    Coastal Charm in Chatham. Located in one of Cape Cod's most sough-after towns, this updated seasonal free standing cottage offers the perfect blend of charm, conveniience and summer living. Just mins to Harding's Beach, shops, and restaurants, it features a bright open layout with vaulted ceilings skylight and whitewashed wood throughout. The kitchen includes vintage inspired appliances butcher

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    19 Captain Richards Way Unit 1, Chatham, MA 02633
  • 6 Stephen Dr, Chatham, MA 02633
    6 Stephen Dr, Chatham, MA 02633
    6 Stephen Dr, Chatham, MA 02633
    /42

    $1,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,069 Sq Ft

    6 Stephen Dr, Chatham, MA 02633

    Set in one of West Chatham's most desirable neighborhoods, minutes from Hardings and Ridgevale beaches, this residence stands out for its scale, flexibility, and refined design. Sunlight fills the interiors, where large windows frame backyard and cranberry bog views and create a bright, welcoming atmosphere. The home offers four bedrooms plus a versatile office/bonus room and 4.5 baths, designed

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    6 Stephen Dr, Chatham, MA 02633
  • 200 Hardings Beach Rd, Chatham, MA 02633
    200 Hardings Beach Rd, Chatham, MA 02633
    200 Hardings Beach Rd, Chatham, MA 02633
    /30

    $1,495,000

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    200 Hardings Beach Rd, Chatham, MA 02633

    Located just a short stroll to Hardings Beach and close to many favorite local restaurants and conveniences, this classic Cape style two story cottage offers the option of summer or year-round living as well as a a rental investment opportunity. With 4 bedrooms and 2 full baths, the layout is designed for easy living, with bedrooms on both levels and full baths conveniently located adjacent to

    Chris Rhinesmith Compass Massachusetts, LLC

    200 Hardings Beach Rd, Chatham, MA 02633
  • 15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    /36

    $899,000

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft

    15 Sylvan Way, South Chatham, MA 02659

    Coastal charm meets timeless elegance at 15 Sylvan Way, tucked on a private lane near beaches, the rail trail, and local dining. This beautifully maintained Colonial is filled with an abundance of natural light from full-length Andersen windows. The open layout features a welcoming living/dining area and a stunning kitchen with high-end appliances, and adjoining mudroom with full bath. Upstairs,

    Jack Bohman Gibson Sotheby's International Realty

    15 Sylvan Way, South Chatham, MA 02659
  • 207 Horizon Dr, Chatham, MA 02633
    207 Horizon Dr, Chatham, MA 02633
    207 Horizon Dr, Chatham, MA 02633
    /35

    $1,650,000

    • 4 Beds
    • 3.5 Baths
    • 2,843 Sq Ft

    207 Horizon Dr, Chatham, MA 02633

    Perched high on a private lot in one of Chatham's most sought-after locations, this stunning residence offers over 2,800 sq. ft. of well-designed living space. Featuring 4 spacious bedrooms and 2.5 baths, the home blends timeless style with modern comfort. Step inside to discover gleaming hardwood floors throughout, two full fireplaces for cozy gathers, and sun-filled rooms that invite

    Jacquelyn Casey Shore Road Realty

    207 Horizon Dr, Chatham, MA 02633
  • 73 Joshua Jethro Rd, Chatham, MA 02633
    73 Joshua Jethro Rd, Chatham, MA 02633
    73 Joshua Jethro Rd, Chatham, MA 02633
    /53

    $1,520,000

    • 3 Beds
    • 2 Baths
    • 2,307 Sq Ft

    73 Joshua Jethro Rd, Chatham, MA 02633

    PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates community, this 3-bedroom, 2-bath, 2,307 sq. ft. home blends classic charm with modern comfort. The farmhouse-style kitchen with newer appliances flows to a spacious living room with fireplace, mudroom, and garage entry. A first-floor bedroom and bath offer flexibility, while a dining room and bright eat-in area

    Paul Borde Christie's International Real Estate Atlantic Brokerage

    73 Joshua Jethro Rd, Chatham, MA 02633

Showing Results 1 - 40, Page 1 of 2

Massachusetts Barnstable County Chatham

Real Estate & Homes for Sale in Chatham, MA

Why Live in Chatham

Located less than a mile from Chatham's downtown district, West Chatham is a coastal community defined by its maritime culture and quick access to the waterfront. “West Chatham offers a lot of beachy, friendly neighborhoods south of state Route 28,” ...

Learn more about living in Chatham

Frequently Asked Questions

What is the average home price in Chatham, MA?
Homes for sale in Chatham, MA have an average home price of $2,805,891.
How many homes have sold over the last 12 months in Chatham, MA?
221 homes have sold in Chatham, MA over the last 12 months.
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 in Chatham, MA?
The most popular neighborhoods in Chatham, MA with the most homes for sale are South Chatham, Chatham Village, North Chatham and West Chatham.
How much do you need to make to afford a house in Chatham?
The median home price in Chatham is $1,899,950. If you put a 20% down payment of $380,000 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $9,280 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $398K a year to afford the median home price in Chatham.
How are the schools in Chatham, MA?
Chatham, MA has highly rated public and private schools. Some of the best schools in Chatham based on Niche Grades are Orleans Elementary School, Nauset Regional High School and Chatham Elementary School. The neighborhoods in Chatham with the highest rated schools are South Chatham, Chatham Village and North Chatham. Browse all the schools in Chatham, MA to learn more.

Home Trends in Chatham, MA

On average, homes in Chatham, MA sell after 81 days on the market compared to the national average of 53 days. The median sale price for homes in Chatham, MA over the last 12 months is $1,511,258, up 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,511,258
Median Single Family Sale Price
$1,995,000
Median Townhouse Sale Price
$4,125,000
Median 2 Bedroom Sale Price
$485,000
Median 1 Bedroom Sale Price
$447,000
Average Price Per Sq Ft
$929
Number of Homes for Sale
49
Last 12 months Home Sales
221
Months of Supply
2.70
Median List Price
$1,899,950
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
15%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group