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Chatham, MA Homes for Sale

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  • 56 Stage Island Rd, Chatham, MA 02633
    56 Stage Island Rd, Chatham, MA 02633
    56 Stage Island Rd, Chatham, MA 02633
    /41

    $5,250,000

    $245K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,932 Sq Ft

    56 Stage Island Rd, Chatham, MA 02633

    Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed

    Agent Photo

    Jim Lowenstern

    eXp Realty LLC

    56 Stage Island Rd, Chatham, MA 02633
  • 65 Captain Kendrick Dr, Chatham, MA 02633
    65 Captain Kendrick Dr, Chatham, MA 02633
    65 Captain Kendrick Dr, Chatham, MA 02633
    /48

    $1,069,000

    $126K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,384 Sq Ft

    65 Captain Kendrick Dr, Chatham, MA 02633

    Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.Offering 1,754 sqft of main-level living, the home many features include an updated

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    65 Captain Kendrick Dr, Chatham, MA 02633
  • 65 Captain Kendrick Dr, Chatham, MA 02633
    65 Captain Kendrick Dr, Chatham, MA 02633
    65 Captain Kendrick Dr, Chatham, MA 02633
    /40

    $1,069,000

    $126K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,752 Sq Ft

    65 Captain Kendrick Dr, Chatham, MA 02633

    Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.Offering 1,754 sqft of main-level living, the home many features include an updated eat-in

    Agent Photo

    Barbara Garside

    eXp Realty LLC

    65 Captain Kendrick Dr, Chatham, MA 02633
  • 66 Ethelma Dr, Chatham, MA 02633
    66 Ethelma Dr, Chatham, MA 02633
    /2

    $4,500,000

    • 4 Beds
    • 4.5 Baths
    • 4,689 Sq Ft

    66 Ethelma Dr, Chatham, MA 02633

    Waterfront new construction in one of Chatham's most preeminent locations, minutes from town. This rare half-acre offering on Emery Pond is to be built by R.A. Martin, one of the Cape's premier builders, with select interior finishes and customizations still available to the right buyer. New construction of this scale is exceptionally rare on Cape Cod, offering the perfect mix of estate-level

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    66 Ethelma Dr, Chatham, MA 02633
  • 71 Rowland Dr, North Chatham, MA 02650
    71 Rowland Dr, North Chatham, MA 02650
    71 Rowland Dr, North Chatham, MA 02650
    /47

    $1,895,000

    • 2 Beds
    • 2 Baths
    • 1,398 Sq Ft

    71 Rowland Dr, North Chatham, MA 02650

    Experience the ultimate waterfront lifestyle in this lovely coastal retreat. Perfectly positioned on the edge of Frost Fish Creek, this charming home captures picturesque water views and is thoughtfully designed for effortless indoor-outdoor living. Enjoy direct tidal access to one of Cape Cod's most treasured waterways. Secure a private mooring and launch your kayak, paddleboard, or boat right

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    71 Rowland Dr, North Chatham, MA 02650
  • 109 Misty Meadow Ln Unit 4, Chatham, MA 02633
    109 Misty Meadow Ln Unit 4, Chatham, MA 02633
    109 Misty Meadow Ln Unit 4, Chatham, MA 02633
    /30

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    109 Misty Meadow Ln Unit 4, Chatham, MA 02633

    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, Chatham, MA 02633
  • 92 Indian Trail, Chatham, MA 02633
    92 Indian Trail, Chatham, MA 02633
    92 Indian Trail, Chatham, MA 02633
    /40

    $3,100,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    92 Indian Trail, Chatham, MA 02633

    Wake each morning to sparkling water views and end your day with spectacular sunsets over Bucks Creek. Located in Chatham's coveted Hardings Beach Hills neighborhood, this thoughtfully updated and meticulously maintained 3-bedroom, 3-bath home captures sweeping westerly water views. The primary suite features a private balcony overlooking the water, while a dedicated office offers flexibility for

    Judith Smith John C Ricotta & Assoc.

    92 Indian Trail, Chatham, MA 02633
  • 212 Orleans Rd Unit D, North Chatham, MA 02650
    212 Orleans Rd Unit D, North Chatham, MA 02650
    212 Orleans Rd Unit D, North Chatham, MA 02650
    /13

    $689,000

    • 2 Beds
    • 2 Baths
    • 1,083 Sq Ft

    212 Orleans Rd Unit D, North Chatham, MA 02650

    Beautifully appointed, fully furnished, and turnkey, this exceptional end-unit 2-bedroom, 2-bath second-floor condominium is located in the desirable Nickerson Corners community in North Chatham, offering effortless Cape Cod living in a quiet, well-maintained association. Ideally situated just moments from Chatham Harbor and downtown Chatham, this exceptional location provides easy access to

    Jim Peterson Peterson Realty Inc.

    212 Orleans Rd Unit D, North Chatham, MA 02650
  • 41 Court St, North Chatham, MA 02650
    41 Court St, North Chatham, MA 02650
    41 Court St, North Chatham, MA 02650
    /38

    $2,295,000

    $655K PRICE DROP
    • 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. 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 FP & wet bar for relaxed moments

    Phyllis Power Compass

    41 Court St, North Chatham, MA 02650
  • 739 Main St Unit 739, Chatham, MA 2633
    739 Main St Unit 739, Chatham, MA 2633
    739 Main St Unit 739, Chatham, MA 2633
    /41

    $1,450,000

    $45K PRICE DROP
    • 2 Beds
    • 3.5 Baths
    • 1,770 Sq Ft

    739 Main St Unit 739, Chatham, MA 2633

    Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers baseball games, band concerts, a sandy beach at Oyster Pond, and much more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen,

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    739 Main St Unit 739, Chatham, MA 2633
  • 190 Heritage Ln, Chatham, MA 02633
    190 Heritage Ln, Chatham, MA 02633
    190 Heritage Ln, Chatham, MA 02633
    /55

    $1,199,000

    Open Sat 10:30AM - 12PM
    • 3 Beds
    • 2.5 Baths
    • 1,884 Sq Ft

    190 Heritage Ln, Chatham, MA 02633

    Experience the best of Chatham living in this beautifully reimagined 3-bedroom, 2.5-bath home, ideally located close to Chatham Village, beaches, White Pond & the bike path. Thoughtfully updated inside and out, the home features a stunning new kitchen with quartz countertops & an AGA professional range, refinished hardwood floors, custom cabinetry, recessed lighting, fresh interior paint, Hunter

    Shane Masaschi Compass

    190 Heritage Ln, Chatham, MA 02633
  • 35 Duncan Ln, Chatham, MA 02633
    35 Duncan Ln, Chatham, MA 02633
    35 Duncan Ln, Chatham, MA 02633
    /42

    $1,350,000

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    35 Duncan Ln, Chatham, MA 02633

    Canoe and kayak on Mill Pond. Direct water front at the end of the cul-de-sac. Turn key - Fully furnished year round and off season rental histoy. Very private and peaceful setting yet conveninet to shopping, restaurants, beaches and highways. 3 Bedrooms, 2 baths. First floor master. Plenty of closet space. Walkout basement. Large deck overlooking Mill Pond. Gas fireplace instert. Gas stove.

    John Habeeb Alliance Realty Advisors, Inc.

    35 Duncan Ln, 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

    $400K PRICE DROP
    • 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 prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean

    John Burke William Raveis Chatham

    238 Cranberry 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
    /38

    $789,000

    $106K PRICE DROP
    • 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 & Associates, Inc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • 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
  • 15 Bay Ln, Chatham, MA 02633
    15 Bay Ln, Chatham, MA 02633
    15 Bay Ln, Chatham, MA 02633
    /40

    $4,950,000

    • 4 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    15 Bay Ln, Chatham, MA 02633

    Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance and is turn key, furnished and ready for summer! Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native

    Chris Rhinesmith Compass

    15 Bay Ln, Chatham, MA 02633
  • 166 Shore Rd, Chatham, MA 02633
    166 Shore Rd, Chatham, MA 02633
    166 Shore Rd, Chatham, MA 02633
    /39

    $8,950,000

    $3M PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,738 Sq Ft

    166 Shore Rd, Chatham, MA 02633

    The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    166 Shore Rd, Chatham, MA 02633
  • 50 Sylvan Way, South Chatham, MA 02659
    50 Sylvan Way, South Chatham, MA 02659
    /2

    $5,900,000

    • 6 Beds
    • 8 Baths
    • 6,183 Sq Ft

    50 Sylvan Way, South Chatham, MA 02659

    The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    50 Sylvan Way, South Chatham, MA 02659
  • 99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    /41

    $5,495,000

    $405K PRICE DROP
    • 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
  • 101 Morris Island Rd, Chatham, MA 02633
    101 Morris Island Rd, Chatham, MA 02633
    101 Morris Island Rd, Chatham, MA 02633
    /42

    $4,995,000

    Open Sat 10AM - 11:30AM $1M PRICE DROP
    • 4 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, beautifully blends elegance and comfort. The open floor plan features oversized windows and soaring ceilings, offering illuminating views of the swimming pool, spa, outdoor kitchen, patio, gas fire pit, and an irrigated, fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse

    The Bohman Hartung Group Gibson Sotheby's International Realty

    101 Morris Island Rd, Chatham, MA 02633
  • 38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    /59

    $4,495,000

    $255K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,967 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings and dramatic walls of glass fill the home with natural light and frame spectacular sunsets; while sliders open to an expansive wraparound deck for effortless indoor-outdoor living. A chef's kitchen, dual living areas, and an

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    38 Indian Trail, Chatham, MA 02633
  • 33 Duck Marsh Ln, Chatham, MA 02633
    33 Duck Marsh Ln, Chatham, MA 02633
    33 Duck Marsh Ln, Chatham, MA 02633
    /36

    $829,000

    Open Fri 1PM - 2:30PM $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    33 Duck Marsh Ln, Chatham, MA 02633

    Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural

    Darci Sequin Gibson Sotheby's International Realty

    33 Duck Marsh Ln, Chatham, MA 02633
  • 157 Bridge St, Chatham, MA 02633
    157 Bridge St, Chatham, MA 02633
    157 Bridge St, Chatham, MA 02633
    /20

    $12,999,900

    New Construction
    • 4 Beds
    • 7 Baths
    • 6,234 Sq Ft

    157 Bridge St, Chatham, MA 02633

    In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    157 Bridge St, Chatham, MA 02633
  • 15 Windy Hill Way, Chatham, MA 02633
    15 Windy Hill Way, Chatham, MA 02633
    15 Windy Hill Way, Chatham, MA 02633
    /42

    $5,850,000

    $400K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,620 Sq Ft

    15 Windy Hill Way, Chatham, MA 02633

    This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

    Tim Bailey John C. Ricotta & Associates, Inc.

    15 Windy Hill Way, Chatham, MA 02633
  • 60 Harbor Hill Rd, Chatham, MA 02633
    60 Harbor Hill Rd, Chatham, MA 02633
    60 Harbor Hill Rd, Chatham, MA 02633
    /54

    $2,950,000

    $650K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,978 Sq Ft

    60 Harbor Hill Rd, Chatham, MA 02633

    TURNKEY!! Just open the door in one of Chatham's most desirable neighborhoods, is this property that offers a blend of classic Cape Cod charm & refined living. Set on 40,500 sq. ft. of beautifully landscaped grounds, the home invites both quiet retreat and gracious living. Inside, rich pine floors flow throughout a lovely designed layout featuring 10 spacious rooms, including 4 bedrooms & 3.5

    Jacquelyn Casey Shore Road Realty

    60 Harbor Hill Rd, Chatham, MA 02633
  • 222 Barcliff Ave, Chatham, MA 02633
    222 Barcliff Ave, Chatham, MA 02633
    222 Barcliff Ave, Chatham, MA 02633
    /15

    $4,250,000

    New Construction $100K PRICE INCREASE
    • 4 Beds
    • 5.5 Baths
    • 3,980 Sq Ft

    222 Barcliff Ave, Chatham, MA 02633

    The location that has it all...walk to both town, fish pier, beach and baseball games....New Farmhouse with pool built by Morgan and Sons and expecting completion by August 1 st.. Enjoy Chatham from this 4BR 5.5 bath , 3980 sq foot home. All bedrooms offer spacious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings with

    Lori Fanning Smith Compass Massachusetts, LLC

    222 Barcliff Ave, Chatham, MA 02633
  • 1772 Main St, Chatham, MA 2633
    1772 Main St, Chatham, MA 2633
    1772 Main St, Chatham, MA 2633
    /15

    $699,999

    • 0.5 Baths
    • 600 Sq Ft

    1772 Main St, Chatham, MA 2633

    Residential Potential in Chatham'sR20 Zone!This unique property offers a rare chance to create a standalone single-family home just moments from downtown Chatham. Note that the building is currently a commercial barber shop under a 1969 variance; however, it is situated in the R20 residential zone. This provides a clear path for conversion: by petitioning the Zoning Board of Appeals (ZBA) to lift

    Erin Terkelsen LPT Realty, LLC

    1772 Main St, Chatham, MA 2633
  • 0 Court St, Chatham, MA 02650
    0 Court St, Chatham, MA 02650
    /2

    $650,000

    • Land
    • 20,908 Sq Ft
    • $1,354,167 per Acre

    0 Court St, Chatham, MA 02650

    Rare to find a 20,737 lot in an established neighborhood of beautiful homes, close to town center or Ryder's Cove...overlooking Frost Fish Creek conservation, birdlife, tranquility! Building lot has been engineered by Ryder and Wilcox, pre- existing sidelines are R20. This lot will be sold separately after the home at 41 Court Street is sold, listed $2,295,000. MLS#22600472 or it can be purchased

    Phyllis Power Compass

    0 Court St, Chatham, MA 02650
  • 48 Hunter Rise, Chatham, MA 2633
    48 Hunter Rise, Chatham, MA 2633
    48 Hunter Rise, Chatham, MA 2633
    /64

    $3,595,000

    • 3 Beds
    • 4 Baths
    • 3,922 Sq Ft

    48 Hunter Rise, Chatham, MA 2633

    Stunning custom home built by Eastward Companies in 2020, ideally situated in Chatham's sought-after Hunter Rise neighborhood just moments from Harding's Beach. Thoughtfully designed with exceptional craftsmanship and timeless finishes, this home features an open-concept floor plan filled with natural light, white oak floors, and custom details throughout. The living room showcases a shiplap

    Chris Rhinesmith Compass Massachusetts, LLC

    48 Hunter Rise, Chatham, MA 2633
  • 336 Stage Island Rd, Chatham, MA 02633
    336 Stage Island Rd, Chatham, MA 02633
    336 Stage Island Rd, Chatham, MA 02633
    /78

    $2,850,000

    $400K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    336 Stage Island Rd, Chatham, MA 02633

    Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, this property delivers a generational setting defined by sweeping marsh and water views,

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    336 Stage Island Rd, Chatham, MA 02633
  • 55 Winterset Dr, Chatham, MA 02633
    55 Winterset Dr, Chatham, MA 02633
    55 Winterset Dr, Chatham, MA 02633
    /44

    $2,390,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property

    Janet Stuart Coldwell Banker Realty

    55 Winterset Dr, 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
    /28

    $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 charming second-floor condominium offers an exceptional opportunity to own in one of the Cape's most coveted locations. Whether you're seeking a seasonal retreat, an investment property, or a smart entry into the Chatham market, this residence delivers a perfect blend of convenience, charm, and value. Filled with natural light, the

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
  • 30 Indian Trail, Chatham, MA 02633
    30 Indian Trail, Chatham, MA 02633
    30 Indian Trail, Chatham, MA 02633
    /26

    $4,200,000

    • 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 showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story

    Chris Rhinesmith Compass

    30 Indian Trail, Chatham, MA 02633
  • 1134 &1142 Main St, Chatham, MA 02633
    1134 &1142 Main St, Chatham, MA 02633
    1134 &1142 Main St, Chatham, MA 02633
    /17

    $1,100,000

    $150K PRICE DROP
    • Land
    • 25,264 Sq Ft
    • $1,896,552 per Acre

    1134 &1142 Main St, Chatham, MA 02633

    Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement. Properties located at 1134 Main Street and 1142 Main Street

    Timothy Bailey John C Ricotta & Assoc.

    1134 &1142 Main St, 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

    346 Morris Island Rd, Chatham, MA 02633
  • 70 Uncle Deane's Rd, Chatham, MA 02659
    70 Uncle Deane's Rd, Chatham, MA 02659
    70 Uncle Deane's Rd, Chatham, MA 02659
    /39

    $1,999,000

    Open Sun 12PM - 1:30PM
    • 3 Beds
    • 3 Baths
    • 3,514 Sq Ft

    70 Uncle Deane's Rd, Chatham, MA 02659

    Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully

    Patrick Davison Shining Sea Realty

    70 Uncle Deane's Rd, Chatham, MA 02659
  • 150 Cross St, Chatham, MA 02633
    150 Cross St, Chatham, MA 02633
    150 Cross St, Chatham, MA 02633
    /28

    $6,500,000

    • 10 Beds
    • 10 Baths
    • 7,658 Sq Ft

    150 Cross St, Chatham, MA 02633

    Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500

    Chris Rhinesmith Compass

    150 Cross St, Chatham, MA 02633
  • 739 Main St Unit 1E, Chatham, MA 2633
    739 Main St Unit 1E, Chatham, MA 2633
    739 Main St Unit 1E, Chatham, MA 2633
    /50

    $1,450,000

    $45K PRICE DROP
    • 2 Beds
    • 3.5 Baths
    • 1,770 Sq Ft

    739 Main St Unit 1E, Chatham, MA 2633

    Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers ball games, concerts, Oyster Pond, and more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen, adjacent dining area, and

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    739 Main St Unit 1E, Chatham, MA 2633
  • 153 Shore Rd, Chatham, MA 02633
    153 Shore Rd, Chatham, MA 02633
    153 Shore Rd, Chatham, MA 02633
    /58

    $9,995,000

    • 3 Beds
    • 2.5 Baths
    • 3,079 Sq Ft

    153 Shore Rd, Chatham, MA 02633

    Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and

    Sarah Keith eXp Realty, LLC

    153 Shore Rd, Chatham, MA 02633
  • 33 Crowell Rd, Chatham, MA 02633
    33 Crowell Rd, Chatham, MA 02633
    33 Crowell Rd, Chatham, MA 02633
    /9

    $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

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    33 Crowell Rd, Chatham, MA 02633

Showing Results 1 - 40, Page 1 of 2

Massachusetts Barnstable County

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, 02650, 02645 and 02646.
What are the most popular neighborhoods near Chatham, MA?
The most popular neighborhoods near Chatham, MA are Chatham Village, West Chatham, North Chatham, South Chatham and East Harwich.
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