57

Chatham, MA Homes for Sale

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  • 27 Fairview Dr, South Chatham, MA 02659
    27 Fairview Dr, South Chatham, MA 02659
    27 Fairview Dr, South Chatham, MA 02659
    /36

    $1,275,000

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft

    27 Fairview Dr, South Chatham, MA 02659

    Tucked in a quiet enclave south of Rt. 28, this inviting South Chatham home blends coastal charm with modern comfort. The open floorplan welcomes you with a fireplaced living room and gleaming hardwood floors that flow seamlessly throughout. The updated kitchen features a center island perfect for casual meals and entertaining, while the spacious, light-filled sunroom offers a serene retreat

    Kathy Doyle Gibson Sotheby's International Realty

    27 Fairview Dr, South Chatham, MA 02659
  • 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 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    /15

    $675,000

    • 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
  • 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 Open Sat 12PM - 2PM

    • 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
  • 50 Hillside Rd, Harwich, MA 02645
    50 Hillside Rd, Harwich, MA 02645
    50 Hillside Rd, Harwich, MA 02645
    /28

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    50 Hillside Rd, Harwich, MA 02645

    Welcome to this inviting 3-bedroom, 2-bath ranch nestled in the heart of South Harwich. Just 1.5 miles from the sandy shores of Red River Beach and with direct access to the scenic Cape Cod Rail Trail, this home offers the perfect blend of coastal relaxation and outdoor adventure.Inside, you'll find multiple living spaces including a bright and airy sunroom, perfect for morning coffee or

    Jonathan Cahoon John C. Ricotta & Associates, Inc.

    50 Hillside Rd, Harwich, MA 02645
  • 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
  • 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 Assn., featuring a private dock, kayak storage, & picnic area. Nestled just 3/10ths of a mile from the pristine sands of Hardings Beach, this property is

    Agent Photo

    Shane Masaschi

    Compass

    (508) 571-0968

    93 Bucks Creek Rd, Chatham, MA 02633
  • 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
  • 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
    /37

    $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
  • 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
  • 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
  • 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
  • 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
  • 58 Sugar Hill Dr, Harwich, MA 02645
    58 Sugar Hill Dr, Harwich, MA 02645
    58 Sugar Hill Dr, Harwich, MA 02645
    /25

    $769,900

    • 2 Beds
    • 2 Baths
    • 1,356 Sq Ft

    58 Sugar Hill Dr, Harwich, MA 02645

    Updated ranch with views of Monomoy River and deeded access for fishing and launching canoes and kayaks out to Pleasant Bay. 2 bedroom, 2 bath home with full basement and garage under. Renovated kitchen with granite countertops, custom made stained glass window, living room with natural gas fireplace, and year round sun room overlooking the river. Stairway to 2nd level bonus room. Raised garden

    Daniel Michael Main Street Realty

    58 Sugar Hill Dr, Harwich, MA 02645
  • 230 Barcliff Ave, Chatham, MA 02633
    230 Barcliff Ave, Chatham, MA 02633
    230 Barcliff Ave, Chatham, MA 02633
    /10

    $4,399,000 New Construction

    • 4 Beds
    • 6 Baths
    • 5,800 Sq Ft

    230 Barcliff Ave, Chatham, MA 02633

    Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway...Architecturally pleasing 4BR 6 bath shingled home 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 5800 sf home will offer the best in new amenities with a

    Lori Fanning Smith Compass Massachusetts, LLC

    230 Barcliff Ave, 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
  • 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
  • 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

    Tucked in a well-loved Chatham neighborhood, with deeded rights to Lover's Lake, this gracious 4-bedroom Cape seamlessly blends coastal living and Cape Cod charm. 207 Horizon Drive possess charm throughout with its spacious and traditional floor plan. Featuring two fireplaces, two full and two half baths, and a sunlit family room off the kitchen. This home is designed for easy living. Enoy

    Jacquelyn Casey Shore Road Realty

    207 Horizon Dr, 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
    /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
  • 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
  • 56 Skyline Dr, Chatham, MA 02633
    56 Skyline Dr, Chatham, MA 02633
    56 Skyline Dr, Chatham, MA 02633
    /32

    $1,599,000

    • 4 Beds
    • 2 Baths
    • 2,392 Sq Ft

    56 Skyline Dr, Chatham, MA 02633

    Enjoy breezy summer days and lots of lake time from this updated 4 Bedroom home located on Great Hill. With deeded rights to Lovers Lake and lake access less than 100 yards outside your door, this classic cape style home invites family fun & enjoying nature all year long. Updates include granite/stainless kitchen w/ breakfast bar, a great room / rec room w/ vaulted beamed ceiling, french doors,

    Janet Stuart Coldwell Banker Realty - Concord

    56 Skyline Dr, Chatham, MA 02633
  • 93 Orleans Rd, Chatham, MA 02633
    93 Orleans Rd, Chatham, MA 02633
    93 Orleans Rd, Chatham, MA 02633
    /48

    $1,359,000

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

    93 Orleans Rd, Chatham, MA 02633

    Welcome to the meticulous and delightful 93 Orleans Road Chatham. Enter onto the beautiful herringbone-designed brick walkway leading to a relaxing covered front porch with durable Azek flooring-perfect for enjoying the fresh Cape Cod sunshine and ocean breeze. This single-level home offers a true slice of paradise. Completely updated in 2024, the 3-bedroom, 2-bath residence blends modern comfort

    Derek Greene The Greene Realty Group

    93 Orleans Rd, Chatham, MA 02633
  • 127 Wapoos Trail, Chatham, MA 02633
    127 Wapoos Trail, Chatham, MA 02633
    127 Wapoos Trail, Chatham, MA 02633
    /35

    $8,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,307 Sq Ft

    127 Wapoos Trail, Chatham, MA 02633

    Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water view residence is a rare treasure offering architectural distinction and an intimate connection to Cape Cod's unspoiled coastal beauty. With panoramic views spanning Stage Harbor to the Atlantic shoreline, the home was thoughtfully designed to embrace its extraordinary setting—inviting nature's ever-changing

    Dee Sullivan Christie's International Real Estate Atlantic Brokerage

    127 Wapoos Trail, Chatham, MA 02633
  • 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
  • 72 Forest Beach Rd, Chatham, MA 02659
    72 Forest Beach Rd, Chatham, MA 02659
    72 Forest Beach Rd, Chatham, MA 02659
    /32

    $1,499,000

    • 6 Beds
    • 5 Baths
    • 2,401 Sq Ft

    72 Forest Beach Rd, Chatham, MA 02659

    South of 28! Renovated Beach Compound with 5 Income-Producing Suites. Just 4/10 of a mile from Nantucket Sound, this iconic South Chatham property blends classic Cape style with modern luxury. Formerly the historic Forest Beach Motel, now meticulously restored and transformed into a stylish coastal compound. Property is offered fully furnished and move-in ready. This unique 6-bedroom, 5-bath

    Michael Magner Berkshire Hathaway HomeServices Robert Paul Properties

    72 Forest Beach Rd, Chatham, MA 02659
  • 72 Forest Beach Rd, South Chatham, MA 2659
    72 Forest Beach Rd, South Chatham, MA 2659
    72 Forest Beach Rd, South Chatham, MA 2659
    /41

    $1,499,000

    • 6 Beds
    • 5 Baths
    • 2,401 Sq Ft

    72 Forest Beach Rd, South Chatham, MA 2659

    South of 28! Renovated Beach Compound with 5 Income-Producing Suites. Just 4/10 of a mile from Nantucket Sound, this iconic South Chatham property blends classic Cape style with modern luxury. Formerly the historic Forest Beach Motel, now meticulously restored and transformed into a stylish coastal compound. Property is offered fully furnished and move-in ready. This unique 6-bedroom, 5-bath

    Michael Magner Berkshire Hathaway HomeServices Robert Paul Properties

    72 Forest Beach Rd, South Chatham, MA 2659
  • 12 Pond St, Chatham, MA 02633
    12 Pond St, Chatham, MA 02633
    12 Pond St, Chatham, MA 02633
    /60

    $7,299,000

    • 4 Beds
    • 5 Baths
    • 4,214 Sq Ft

    12 Pond St, Chatham, MA 02633

    Custom Home in Chatham Village. 4-bedroom, 5-bathroom residence located steps from Oyster Pond and its sandy beach. This thoughtful home offers open floor plan, high ceilings, hardwood floors and expansive water views. Deeded access to an association dock and mooring field for boating enthusiasts. The gourmet kitchen features stone countertops, large center island with seating, and premium

    Tim Bailey John C Ricotta & Assoc.

    12 Pond St, Chatham, MA 02633
  • 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
  • 597 Orleans Rd, North Chatham, MA 02650
    597 Orleans Rd, North Chatham, MA 02650
    597 Orleans Rd, North Chatham, MA 02650
    /42

    $1,225,000

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft

    597 Orleans Rd, North Chatham, MA 02650

    Set on over an acre and a half of beautifully landscaped grounds, this 3-bedroom contemporary home is flooded w/natural light and offers stunning water views, a flexible floor plan and impressive finishes.The welcoming living room offers walls of windows, cathedral ceilings, a focal fireplace and skylights. A white chef’s kitchen has granite counters, stainless appliances and is open to the

    Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650
  • 38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    /49

    $4,750,000

    • 4 Beds
    • 3.5 Baths
    • 3,878 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a

    Chris Rhinesmith Compass Massachusetts, LLC

    38 Indian Trail, Chatham, MA 02633
  • 92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    /53

    $3,500,000

    • 5 Beds
    • 3.5 Baths
    • 2,659 Sq Ft

    92 Barcliff Ave, Chatham, MA 02633

    Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical residence was meticulously restored to perfection in 2002, seamlessly blending its storied heritage with the finest modern luxuries. Nestled in a prime yet private locale, the home's enchanting exterior teases with a glimpse of the lush, secluded garden, a serene oasis framed by a stately pergola. The

    Chris Rhinesmith Compass Massachusetts, LLC

    92 Barcliff Ave, 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

Showing Results 1 - 40, Page 1 of 2

Massachusetts Barnstable County Chatham

Real Estate & Homes for Sale in Chatham, MA

Frequently Asked Questions

What is the average home price in Chatham, MA?
Homes for sale in Chatham, MA have an average home price of $2,805,121.
How many homes have sold over the last 12 months in Chatham, MA?
219 homes have sold in Chatham, MA over the last 12 months.
Is Chatham, MA a safe city?
In general, the safest neighborhoods in Chatham, MA with lower crime scores are South Chatham, Chatham Village, North Chatham and West 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 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 $1,895,000. If you put a 20% down payment of $379,000 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $9,320 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $399K a year to afford the median home price in Chatham. Learn how much home you can afford with our Home Affordability Calculator.
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 80 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 16% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,511,258
Median Single Family Sale Price
$1,975,000
Median Townhouse Sale Price
$4,125,000
Median 2 Bedroom Sale Price
$480,000
Median 1 Bedroom Sale Price
$399,000
Average Price Per Sq Ft
$924
Number of Homes for Sale
38
Last 12 months Home Sales
219
Months of Supply
2.10
Median List Price
$1,895,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
16%
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