59

Chatham, MA Homes for Sale

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

    $5,495,000

    Open Sat 11AM - 1PM
    • 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

    (508) 290-1631

    56 Stage Island Rd, Chatham, MA 02633
  • 39 Jedidiah Way, Chatham, MA 02633
    39 Jedidiah Way, Chatham, MA 02633
    39 Jedidiah Way, Chatham, MA 02633
    /47

    $1,650,000

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,810 Sq Ft

    39 Jedidiah Way, Chatham, MA 02633

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

    Agent Photo

    Tom Jones

    Berkshire Hathaway HomeServices Robert Paul Properties

    (508) 290-1665

    39 Jedidiah Way, Chatham, MA 02633
  • 101 Morris Island Rd, Chatham, MA 02633
    101 Morris Island Rd, Chatham, MA 02633
    101 Morris Island Rd, Chatham, MA 02633
    /77

    $5,995,000

    • 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

    The Bohman Hartung Group Gibson Sotheby's International Realty

    101 Morris Island Rd, Chatham, MA 02633
  • 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

    Situated on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath, shingle-style residence is designed for seamless indoor and outdoor entertaining. The bright, airy first floor is anchored by a great room with a Rumford fireplace, custom cabinets, 10' ceilings, and towering windows. The professional-grade kitchen features premier appliances, a pantry, a wet bar, and a large center island.

    The Bohman Hartung Group Gibson Sotheby's International Realty

    335 Stage Island Rd, Chatham, MA 02633
  • 260 Tanglewood Dr, South Chatham, MA 02659
    260 Tanglewood Dr, South Chatham, MA 02659
    260 Tanglewood Dr, South Chatham, MA 02659
    /41

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    260 Tanglewood Dr, South Chatham, MA 02659

    One-floor living for your retreat or year-round residence! A wood-burning fireplace anchors the inviting living room while a large bay window welcomes the sunlight! The main bedroom offers an en suite bath and private outdoor access—ideal if you decide to add a hot tub behind the house! The 1st-floor laundry and bonus space are handy where there was previously a garage. The unfinished lower level

    Amy Harbeck Kinlin Grover Compass

    260 Tanglewood Dr, South Chatham, MA 02659
  • 2386 Main St, South Chatham, MA 02659
    2386 Main St, South Chatham, MA 02659
    2386 Main St, South Chatham, MA 02659
    /4

    $315,000

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

    2386 Main St, South Chatham, MA 02659

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

    Judith Smith John C Ricotta & Assoc.

    2386 Main St, South Chatham, MA 02659
  • 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
  • 243 Crowell Rd, Chatham, MA 02633
    243 Crowell Rd, Chatham, MA 02633
    243 Crowell Rd, Chatham, MA 02633
    /48

    $1,350,000

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

    243 Crowell Rd, Chatham, MA 02633

    Comfortable Cape style 3 bedroom home, close to down-town Chatham Village, Oyster Pond Beach and exceptional dining. Set back from the road on a level, grassy front lawn, Updated chef's kitchen, newer A/C splits, fenced, sunny back yard with deck. Free standing 2 car garage on over .6 acre lot. Unfinished second floor offers expansion potential with previously permitted plan. Large unfinished

    Michael Hall William Raveis Real Estate & Home Services

    243 Crowell Rd, Chatham, MA 02633
  • 60 Harbor Hill Rd, Chatham, MA 02633
    60 Harbor Hill Rd, Chatham, MA 02633
    60 Harbor Hill Rd, Chatham, MA 02633
    /51

    $3,600,000

    • 4 Beds
    • 3.5 Baths
    • 3,978 Sq Ft

    60 Harbor Hill Rd, Chatham, MA 02633

    Tucked away in Chatham's most desirable residential enclaves, this property 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 baths The gourmet kitchen is

    Jacquelyn Casey Shore Road Realty

    60 Harbor Hill Rd, 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
  • 301 Whidah Rd, North Chatham, MA 2650
    301 Whidah Rd, North Chatham, MA 2650
    301 Whidah Rd, North Chatham, MA 2650
    /52

    $12,950,000

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

    301 Whidah Rd, North Chatham, MA 2650

    Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha's Vineyard Interior Designs. Walls of glass frame sweeping vistas and invite natural light to pour in throughout the home. Indoor and outdoor spaces flow effortlessly, from sun-drenched rooms to generous

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, North Chatham, MA 2650
  • 83 Old Mail Rd, North Chatham, MA 02650
    83 Old Mail Rd, North Chatham, MA 02650
    83 Old Mail Rd, North Chatham, MA 02650
    /49

    $3,695,000

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

    83 Old Mail Rd, North Chatham, MA 02650

    Brand new shingled style Coastal retreat offers resort style living in sought after North Chatham location. Sited on .5 of an acre( with pool potential) near beaches and close proximity to town, Chatham Bars Inn and Chatham Seaside Links Golf , this home was curated with luxury and comfort in mind. Exceptional scale, volume and open feel, delivering high end finishes and compelling value at $717

    Lori Fanning Smith Compass Massachusetts, LLC

    83 Old Mail Rd, North Chatham, MA 02650
  • 301 Whidah Rd, Chatham, MA 02650
    301 Whidah Rd, Chatham, MA 02650
    301 Whidah Rd, Chatham, MA 02650
    /42

    $12,950,000

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

    301 Whidah Rd, Chatham, MA 02650

    Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha’s Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, Chatham, MA 02650
  • 137 Shane Dr, Chatham, MA 02633
    137 Shane Dr, Chatham, MA 02633
    137 Shane Dr, Chatham, MA 02633
    /50

    $1,495,000

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

    137 Shane Dr, Chatham, MA 02633

    Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels with 2,448 sqft (1,530

    Tom Riley Compass Massachusetts, LLC

    137 Shane Dr, Chatham, MA 02633
  • 48 Glover Square, Chatham, MA 02633
    48 Glover Square, Chatham, MA 02633
    48 Glover Square, Chatham, MA 02633
    /35

    $1,650,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 2 Baths
    • 2,169 Sq Ft

    48 Glover Square, Chatham, MA 02633

    Chatham By The Sea. Rare 50-year offering. 48 Glover Sq presents a premier opportunity in Chatham. Incredible, coveted location 2 blocks to downtown Chatham Village. Chatham Fish Pier, Oyster Pond, Veterans Field, shopping, grocery, tennis, golf, all 1/2 mile away. Spacious one-floor living with room to reimagine! Add a second story? Ranch home is 1531 square feet and includes 3 bedrooms, large

    Laurie McCann Gibson Sotheby's International Realty

    48 Glover Square, 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
  • 304 Round Cove Rd, Chatham, MA 02633
    304 Round Cove Rd, Chatham, MA 02633
    304 Round Cove Rd, Chatham, MA 02633
    /30

    $895,000

    Open Sat 11AM - 1PM $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,896 Sq Ft

    304 Round Cove Rd, Chatham, MA 02633

    Tucked away in one of Chatham's most desirable neighborhoods, this charming Cape Cod retreat offers the perfect blend of privacy, comfort, and coastal living. Situated on a generous 0.76-acre lot, this well-maintained three-bedroom, two-bath home provides nearly 1,900 square feet of inviting living space designed for year-round enjoyment or the ideal vacation getaway. The thoughtfully designed

    Kimberly Arena Venture

    304 Round Cove Rd, Chatham, MA 02633
  • 7 Cove Rd, Chatham, MA 02650
    7 Cove Rd, Chatham, MA 02650
    7 Cove Rd, Chatham, MA 02650
    /9

    $5,750,000

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

    7 Cove Rd, Chatham, MA 02650

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

    Chris Rhinesmith Compass Massachusetts, LLC

    7 Cove Rd, Chatham, MA 02650
  • 33 Jeanette Rd, Chatham, MA 02633
    33 Jeanette Rd, Chatham, MA 02633
    33 Jeanette Rd, Chatham, MA 02633
    /17

    $985,000

    Open Sat 11AM - 1PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    33 Jeanette Rd, Chatham, MA 02633

    Lovingly updated and meticulously maintained, this turnkey 3-bedroom, 2-bath ranch offers the perfect blend of comfort, convenience, and Cape Cod charm. Gently used and move-in ready, this furnished home features gorgeous wood floors, a wood-burning fireplace, an updated kitchen, and two renovated full bathrooms. The mini-split heated and cooled sunroom provides additional year-round living space

    Kari Wagner Compass

    33 Jeanette Rd, Chatham, MA 02633
  • 234 Round Cove Rd, Chatham, MA 02633
    234 Round Cove Rd, Chatham, MA 02633
    234 Round Cove Rd, Chatham, MA 02633
    /55

    $2,150,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,481 Sq Ft

    234 Round Cove Rd, Chatham, MA 02633

    Tucked within Chatham's coveted Riverbay community, 234 Round Cove Road offers a rare blend of walkability and private, resort-style living. Moments to Jackknife Beach and Pleasant Bay, the setting delivers coastal access while feeling entirely private and your own.Designed for effortless living, the single-level layout features three oversized bedrooms and 2.5 baths, including a secluded primary

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    234 Round Cove Rd, Chatham, MA 02633
  • 92 Indian Trail, Chatham, MA 02633
    92 Indian Trail, Chatham, MA 02633
    92 Indian Trail, Chatham, MA 02633
    /34

    $3,100,000

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

    92 Indian Trail, Chatham, MA 02633

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

    Judith Smith John C Ricotta & Assoc.

    92 Indian Trail, Chatham, MA 02633
  • 33 Crowell Rd, Chatham, MA 02633
    33 Crowell Rd, Chatham, MA 02633
    33 Crowell Rd, Chatham, MA 02633
    /10

    $4,499,900

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

    33 Crowell Rd, Chatham, MA 02633

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

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

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

    $1,650,000

    $345K PRICE DROP
    • 1 Bath
    • 2,586 Sq Ft

    231 Crowell Rd, Chatham, MA 2633

    Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

    Judith Smith John C. Ricotta & Associates, Inc.

    231 Crowell Rd, Chatham, MA 2633
  • 346 Morris Island Rd, Chatham, MA 02633
    346 Morris Island Rd, Chatham, MA 02633
    346 Morris Island Rd, Chatham, MA 02633
    /33

    $4,500,000

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

    346 Morris Island Rd, Chatham, MA 02633

    Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water

    Chris Rhinesmith Compass Massachusetts, LLC

    346 Morris Island Rd, Chatham, MA 02633
  • 38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    /72

    $4,750,000

    • 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
  • 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
  • 70 Uncle Deane's Rd, Chatham, MA 02659
    70 Uncle Deane's Rd, Chatham, MA 02659
    70 Uncle Deane's Rd, Chatham, MA 02659
    /42

    $1,999,000

    • 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
  • 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
  • 21 Quail Trail, South Chatham, MA 02659
    21 Quail Trail, South Chatham, MA 02659
    21 Quail Trail, South Chatham, MA 02659
    /15

    $760,000

    • 2 Beds
    • 1.5 Baths
    • 864 Sq Ft

    21 Quail Trail, South Chatham, MA 02659

    This adorable turn-key 2 bedroom 1 1/2 bath home sited on .26 acres was thoughtfully overhauled in 2021 to include refinished hardwood, interior paint as well as a fully renovated kitchen and bathrooms. A blank canvas in the form of an unfinished walk out basement with windows and sliders is left to the buyer's imagination for any number of uses and leads to a private backyard on this sleepy dead

    Jon Clark Nauset Management

    21 Quail Trail, South Chatham, MA 02659
  • 49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    /40

    $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 & Assoc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • 32 Tip Cart Dr, Chatham, MA 02633
    32 Tip Cart Dr, Chatham, MA 02633
    32 Tip Cart Dr, Chatham, MA 02633
    /31

    $1,350,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,802 Sq Ft

    32 Tip Cart Dr, Chatham, MA 02633

    Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches, Veteran's Field, and the bike path, this three-bedroom, two-bath home offers an exceptional opportunity in a prime Chatham location. Built in 1994, the 1,802 square foot property includes a one-car garage and full basement, providing a strong foundation for your vision. Additional features include wood

    Shane Masaschi Compass

    32 Tip Cart Dr, Chatham, MA 02633
  • 727 Main St, Chatham, MA 02633
    727 Main St, Chatham, MA 02633
    727 Main St, Chatham, MA 02633
    /5

    $999,000

    • Land
    • 6,969 Sq Ft
    • $6,243,750 per Acre

    727 Main St, Chatham, MA 02633

    Build your 3 bedroom home in this awesome downtown location walk to everywhere you want to be in Chatham. Meander across the street to Chatham A's Lilly's, the Squire steps to Oyster Pond no car necessary. The property is surrounded by amazing gardens. A sanctuary a feast for the eyes. Call your builder bring your imagination. A oasis in downtown Chatham.

    Noreen Kennedy Kennedy Real Estate

    727 Main St, Chatham, MA 02633
  • 169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    /53

    $4,900,000

    Open Sat 3:30PM - 5PM $500K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 5,587 Sq Ft

    169 Tisquantum Rd, Chatham, MA 02633

    Located in Chatham's exclusive Quitnesset neighborhood on Morris Island, ideally situated between the Association's private deeded beach and the trails of the protected Monomoy National Wildlife Refuge, this elegant and spacious home embodies the quintessential Cape Cod lifestyle. Step into the sunlit foyer leading to a soaring great room with a fireplace and a chef's kitchen designed for

    Sandra Tanco Kinlin Grover Compass

    169 Tisquantum Rd, Chatham, MA 02633
  • 7 Fox Hill Rd, Chatham, MA 02633
    7 Fox Hill Rd, Chatham, MA 02633
    7 Fox Hill Rd, Chatham, MA 02633
    /6

    $2,400,000

    $446K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,317 Sq Ft

    7 Fox Hill Rd, Chatham, MA 02633

    ''Step back in time while enjoying modern comfort in this charming historic home, originally built in 1810 and beautifully preserved with character and warmth throughout. Rich wood beams, original architectural details and timeless craftsmanship create a unique sense of place that is increasingly rare to find.The home seamlessly blends its historic charm with a newer addition featuring a

    Pam Roberts Gibson Sotheby's International Realty

    7 Fox Hill Rd, Chatham, MA 02633
  • 2653 Main St, South Chatham, MA 02659
    2653 Main St, South Chatham, MA 02659
    2653 Main St, South Chatham, MA 02659
    /28

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    2653 Main St, South Chatham, MA 02659

    Discover a unique opportunity to own a versatile property in one of Cape Cod’s most desirable towns, offering potential as a private residence, multi-family retreat, or investment property. Located less than three-quarters of a mile from the beach, this property has multiple possibilities.The property currently includes a two-bedroom apartment and a separate studio apartment, providing immediate

    Sharon Kingman Dixon William Raveis Real Estate & Homes Services

    2653 Main St, South Chatham, MA 02659
  • 66 Snow Ln, Chatham, MA 02633
    66 Snow Ln, Chatham, MA 02633
    66 Snow Ln, Chatham, MA 02633
    /41

    $849,000

    $51K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    66 Snow Ln, Chatham, MA 02633

    Tucked away in the heart of Chatham, 66 Snow Lane offers a rare blend of privacy, convenience, & natural beauty. This charming 2-bedroom, 1-bath ranch-style home is surrounded by conservation land, creating a peaceful setting where birds, wildlife, and wooded views can be enjoyed from every window. Thoughtfully designed for easy one-floor living, the home features a wood burning fireplace,

    Shane Masaschi Compass

    66 Snow Ln, 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
  • 99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    99 Uncle Alberts Drive Extension, Chatham, MA 2633
    /44

    $5,495,000

    $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
  • 15 Windy Hill Way, Chatham, MA 02633
    15 Windy Hill Way, Chatham, MA 02633
    15 Windy Hill Way, Chatham, MA 02633
    /93

    $6,250,000

    • 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 & Assoc.

    15 Windy Hill Way, Chatham, MA 02633
  • 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

Showing Results 1 - 40, Page 1 of 2

Massachusetts Barnstable County Chatham

Real Estate & Homes for Sale in Chatham, MA

Frequently Asked Questions

Is Chatham, MA a safe city?
In general, the safest neighborhoods in Chatham, MA with lower crime scores are Chatham Village, North Chatham, West Chatham and South Chatham.
What are the most popular zip codes in Chatham, MA?
The most popular zip codes in Chatham, MA include 02659, 02633, 02645, 02653 and 02650.
What are the most popular neighborhoods near Chatham, MA?
The most popular neighborhoods near Chatham, MA are South Chatham, West Chatham, Chatham Village, Harwich Port and North Chatham.
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 © 2026 CoStar Group