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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
    /42

    $4,995,000

    $500K 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
  • 2673 Main St, South Chatham, MA 02659
    2673 Main St, South Chatham, MA 02659
    2673 Main St, South Chatham, MA 02659
    /64

    $849,000

    • 4 Beds
    • 2 Baths
    • 1,635 Sq Ft

    2673 Main St, South Chatham, MA 02659

    Classic Cape Cod Charm, a touch of history and a wonderful South Chatham location come together in this well-cared-for antique Greek Revival, treasured by the same family for generations and now ready for its next chapter. Offering four bedrooms and two full baths, the home has everything you hope to find in a Cape Cod antique: beautiful hardwood floors, high ceilings, two staircases, sun-filled

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    2673 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
    /34

    $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
  • 12 Pond St, Chatham, MA 02633
    12 Pond St, Chatham, MA 02633
    12 Pond St, Chatham, MA 02633
    /95

    $6,875,000

    • 4 Beds
    • 5 Baths
    • 4,512 Sq Ft

    12 Pond St, Chatham, MA 02633

    Few homes command Oyster Pond like 12 Pond Street. Three soaring peaks, the center crowned in sculptural rounded copper, announce a custom Eastward Companies build of rare craftsmanship, with immediate proximity to Main Street and the beach. Inside, every room turns toward the water. The open first floor is anchored by a kitchen perched above stunning views, its custom cabinetry and large island

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    12 Pond St, Chatham, MA 02633
  • 87 Cranberry Ln, Chatham, MA 02633
    87 Cranberry Ln, Chatham, MA 02633
    87 Cranberry Ln, Chatham, MA 02633
    /47

    $1,495,000

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft

    87 Cranberry Ln, Chatham, MA 02633

    Location, location, location! Exceptional opportunity to own this charming year-round home and vacation retreat just steps from coveted Ridgevale Beach. This warm, inviting ranch has 3 bedrooms and 2 full baths, offering easy one floor living as well as additional space with a separate entrance on the lower level for storage and recreation. Savor the saltwater views and gentle breezes in the

    David Carter Compass Massachusetts, LLC

    87 Cranberry Ln, 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
  • 103 Aunt Nabbys Ln, Chatham, MA 02633
    103 Aunt Nabbys Ln, Chatham, MA 02633
    103 Aunt Nabbys Ln, Chatham, MA 02633
    /47

    $4,950,000

    • 3 Beds
    • 4 Baths
    • 3,441 Sq Ft

    103 Aunt Nabbys Ln, Chatham, MA 02633

    Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    103 Aunt Nabbys Ln, Chatham, MA 02633
  • 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
  • 35 Duncan Ln, Chatham, MA 02633
    35 Duncan Ln, Chatham, MA 02633
    35 Duncan Ln, Chatham, MA 02633
    /40

    $1,250,000

    $100K PRICE DROP
    • 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
  • 20 Stoughton Ln, Chatham, MA 2633
    20 Stoughton Ln, Chatham, MA 2633
    20 Stoughton Ln, Chatham, MA 2633
    /34

    $2,285,000

    • 5 Beds
    • 4 Baths
    • 2,478 Sq Ft

    20 Stoughton Ln, Chatham, MA 2633

    The magic here is in the location .... leave the car behind, grab a towel and head to stunning Ridgevale Road Beach, a mere 1/10th mile away. This 5-bedroom, 4-bath Chatham residence is privately positioned on .81 acres of natural surroundings offering a rare sense of privacy. From the moment you enter this pristine home, abundant natural light, gleaming hardwood floors and an inviting sense of

    Elaine Babineau Lomenzo William Raveis Real Estate & Home Services

    20 Stoughton Ln, Chatham, MA 2633
  • 72 Ridgevale Rd, Chatham, MA 02633
    72 Ridgevale Rd, Chatham, MA 02633
    72 Ridgevale Rd, Chatham, MA 02633
    /42

    $2,499,000

    • 2 Beds
    • 2 Baths
    • 1,547 Sq Ft

    72 Ridgevale Rd, Chatham, MA 02633

    Perched in one of Chatham's most sought-after coastal neighborhoods, 72 Ridgevale Road South is a rare Cape Cod offering with sweeping views of Bucks Creek, Nantucket Sound, and Ridgevale Beach. Rebuilt in 2002 and beautifully maintained, this move-in ready Chatham home captures sparkling water views from nearly every angle and offers the coastal lifestyle buyers come to Cape Cod to find. A

    Shane Masaschi Compass

    72 Ridgevale Rd, Chatham, MA 02633
  • 20 Circle Dr, South Chatham, MA 02659
    20 Circle Dr, South Chatham, MA 02659
    20 Circle Dr, South Chatham, MA 02659
    /55

    $2,240,000

    • 4 Beds
    • 3 Baths
    • 3,102 Sq Ft

    20 Circle Dr, South Chatham, MA 02659

    A meticulously maintained and beautifully decorated beach home awaits you in the quaint village of South Chatham. Ideally situated between downtown Chatham and Harwich Port, this exceptional property offers the perfect blend of comfort, privacy, convenience and classic Cape Cod charm. Nestled near Forest Beach, Mill Creek, the Cape Cod Rail Trail, tennis court and conservation areas, this home

    Barbara Carroll-Horne Gibson Sotheby's International Realty

    20 Circle Dr, South Chatham, MA 02659
  • 39 Jedidiah Way, Chatham, MA 02633
    39 Jedidiah Way, Chatham, MA 02633
    39 Jedidiah Way, Chatham, MA 02633
    /43

    $1,495,000

    • 2 Beds
    • 2 Baths
    • 1,810 Sq Ft

    39 Jedidiah Way, Chatham, MA 02633

    Welcome to 39 Jedidiah Way, a beautifully maintained Cape Cod residence set on an elevated, meticulously landscaped half-acre at the end of a quiet cul-de-sac. Offering privacy, direct access to the bike path, and convenient proximity to Chatham's beaches, recreation, restaurants, and village amenities, this inviting home presents an exceptional opportunity to embrace the Cape Cod lifestyle. A

    The Grattan Group Christie's International Real Estate Atlantic Brokerage

    39 Jedidiah Way, Chatham, MA 02633
  • 169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    169 Tisquantum Rd, Chatham, MA 02633
    /80

    $4,495,000

    • 5 Beds
    • 4.5 Baths
    • 5,887 Sq Ft

    169 Tisquantum Rd, Chatham, MA 02633

    Beyond the Chatham Lighthouse, with over an acre on Morris Island, a five-bedroom estate of more than 5,000 square feet keeps its own quiet company. Deeded beach rights through the Quitnesset Association put the sand a short stroll away, while Main Street waits minutes behind you. A grand staircase rising from the foyer gives arrival a true sense of occasion. At the heart of the home, a vaulted

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    169 Tisquantum Rd, Chatham, MA 02633
  • 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
  • 32 Tip Cart Dr, Chatham, MA 02633
    32 Tip Cart Dr, Chatham, MA 02633
    32 Tip Cart Dr, Chatham, MA 02633
    /27

    $1,295,000

    • 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
  • 71 Rowland Dr, North Chatham, MA 02650
    71 Rowland Dr, North Chatham, MA 02650
    71 Rowland Dr, North Chatham, MA 02650
    /22

    $1,795,000

    $100K PRICE DROP
    • 3 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
  • 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
  • 33 Duck Marsh Ln, Chatham, MA 02633
    33 Duck Marsh Ln, Chatham, MA 02633
    33 Duck Marsh Ln, Chatham, MA 02633
    /36

    $829,000

    $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
  • 288 Training Field Rd, Chatham, MA 02633
    288 Training Field Rd, Chatham, MA 02633
    288 Training Field Rd, Chatham, MA 02633
    /34

    $1,200,000

    Open Fri 3PM - 5PM
    • 2 Beds
    • 3 Baths
    • 2,380 Sq Ft

    288 Training Field Rd, Chatham, MA 02633

    Welcome to this beautifully designed contemporary home set amidst professionally landscaped grounds in desirable Chatham. Thoughtfully appointed for easy, low-maintenance living, the home offers 1,344 SF on the main level plus 1,036 SF of finished lower-level space with a full bath. The open floor plan flows effortlessly from the inviting living area to the outdoor deck, perfect for relaxed

    Karen Quinn William Raveis Real Estate & Home Services

    288 Training Field 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
    /57

    $2,950,000

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

    60 Harbor Hill Rd, Chatham, MA 02633

    TURNKEY!! Chatham Living — Ready to Enjoy from Day One Privately sited on nearly an acre, this beautifully maintained 4-bedroom Chatham home offers nearly 4,000 square feet of comfortable, gracious living—turnkey and ready to enjoy from the moment you arrive. Spacious and welcoming, the home features a well-appointed kitchen, generous gathering spaces, three fireplaces, central air, a first-floor

    Jacquelyn Casey Shore Road Realty

    60 Harbor Hill Rd, Chatham, MA 02633
  • 216 Orleans Rd Unit D, North Chatham, MA 02650
    216 Orleans Rd Unit D, North Chatham, MA 02650
    216 Orleans Rd Unit D, North Chatham, MA 02650
    /24

    $659,000

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    216 Orleans Rd Unit D, North Chatham, MA 02650

    Spacious and sunny condo in North Chatham set on the corner of Stoney Hill Rd. Walk to Cow yard beach and admire the historic homes along the way. Or walk in the opposite direction towards down town Chatham. The location and size of this condo will win your heart. Offered completely furnished with many recent upgrades including new AC, new deck, new windows and roof. This condo is graced with

    Kathleen Phelan Compass

    216 Orleans Rd Unit D, North Chatham, MA 02650
  • 48 Hillcrest Rd, Chatham, MA 02633
    48 Hillcrest Rd, Chatham, MA 02633
    48 Hillcrest Rd, Chatham, MA 02633
    /61

    $5,900,000

    • 4 Beds
    • 5.5 Baths
    • 5,254 Sq Ft

    48 Hillcrest Rd, Chatham, MA 02633

    An Ed Acton/Harbor Builders home built in 2019, located in the highly desired section of North Chatham. Offering 4 bedrooms, 6 baths, this home has expansive views of Chatham's inner harbor and beyond. Over 5,000 sq ft of refined entertainment space meeting town requirements for a pool, necessary piping already installed, on a level plot of land. This property has beautiful mature flowering

    Bill Storff Compass Massachusetts, LLC

    48 Hillcrest Rd, Chatham, MA 02633
  • 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
  • 106 Barcliff Ave, Chatham, MA 02633
    106 Barcliff Ave, Chatham, MA 02633
    106 Barcliff Ave, Chatham, MA 02633
    /35

    $5,250,000

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft

    106 Barcliff Ave, Chatham, MA 02633

    Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings

    Jill Boudreau eXp Realty LLC - Corporate Office

    106 Barcliff Ave, Chatham, MA 02633
  • 26 Chatham Heights Rd, Chatham, MA 2633
    26 Chatham Heights Rd, Chatham, MA 2633
    26 Chatham Heights Rd, Chatham, MA 2633
    /64

    $3,100,000

    • 3 Beds
    • 3.5 Baths
    • 4,053 Sq Ft

    26 Chatham Heights Rd, Chatham, MA 2633

    Spectacular custom-built Chatham home designed for effortless entertaining, offering three bedrooms, two bonus rooms, inviting living spaces on all three levels, and a picture-perfect backyard pool setting. A charming front porch welcomes you into a light-filled interior rich with coastal character. The main living room features custom built-ins, shiplap detail, and a wood-burning fireplace,

    Chris Rhinesmith Compass Massachusetts, LLC

    26 Chatham Heights Rd, Chatham, MA 2633
  • 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
  • 190 Heritage Ln, Chatham, MA 02633
    190 Heritage Ln, Chatham, MA 02633
    190 Heritage Ln, Chatham, MA 02633
    /42

    $1,175,000

    $24K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,884 Sq Ft

    190 Heritage Ln, Chatham, MA 02633

    Shane Masaschi Compass

    190 Heritage Ln, Chatham, MA 02633
  • 1114 Orleans Rd Unit 8, North Chatham, MA 02650
    1114 Orleans Rd Unit 8, North Chatham, MA 02650
    1114 Orleans Rd Unit 8, North Chatham, MA 02650
    /60

    $1,375,000

    • 2 Beds
    • 2.5 Baths
    • 2,306 Sq Ft

    1114 Orleans Rd Unit 8, North Chatham, MA 02650

    One of the iconic Christopher Ryder House condominiums can be yours in time for the Fall season. This elegant two-bedroom, three-bath home blends timeless architectural character with refined two-level living. Gracious rooms, high ceilings, oversized windows, skylights, original beams, and warm wood floors create an inviting atmosphere throughout. The open floor plan features a spacious living

    Betsy Hargreaves Gibson Sotheby's International Realty

    1114 Orleans Rd Unit 8, North Chatham, MA 02650
  • 31 Old Village Rd, Chatham, MA 02633
    31 Old Village Rd, Chatham, MA 02633
    31 Old Village Rd, Chatham, MA 02633
    /41

    $815,000

    $60K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,167 Sq Ft

    31 Old Village Rd, Chatham, MA 02633

    This classic Colonial-style home is set on a quiet road ending in a cul-de-sac, close to the Cape Cod Rail Trail and Nantucket Sound beaches. The welcoming first floor features a living room with a wood-burning fireplace, a spacious dining room with hardwood floors, an eat-in kitchen, a bedroom, a bath, and a convenient laundry area. An enclosed, unfinished breezeway offers the potential for a

    Shane Masaschi Compass

    31 Old Village 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

    $1,799,000

    $200K PRICE DROP
    • 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
  • 336 Stage Island Rd, Chatham, MA 02633
    336 Stage Island Rd, Chatham, MA 02633
    336 Stage Island Rd, Chatham, MA 02633
    /42

    $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 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, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    336 Stage Island Rd, Chatham, MA 02633
  • 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
  • 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
  • 48 Sylvan Way, South Chatham, MA 02659
    48 Sylvan Way, South Chatham, MA 02659
    48 Sylvan Way, South Chatham, MA 02659
    /42

    $4,500,000

    $750K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    48 Sylvan Way, South Chatham, MA 02659
  • 600 Fox Hill Rd, Chatham, MA 2633
    600 Fox Hill Rd, Chatham, MA 2633
    600 Fox Hill Rd, Chatham, MA 2633
    /24

    $4,250,000

    • 3 Beds
    • 3.5 Baths
    • 3,071 Sq Ft

    600 Fox Hill Rd, Chatham, MA 2633

    Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and

    Chris Rhinesmith Compass Massachusetts, LLC

    600 Fox Hill Rd, Chatham, MA 2633
  • 78 Indian Trail, Chatham, MA 02633
    78 Indian Trail, Chatham, MA 02633
    78 Indian Trail, Chatham, MA 02633
    /48

    $2,700,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    78 Indian Trail, Chatham, MA 02633

    Discover the charm of coastal living just moments from Hardings Beach. This inviting 3-bedroom, 2-bath home enjoys beautiful water views over Bucks Creek and spectacular west-facing sunsets. Private stairs lead directly to the water's edge, making it easy to launch a kayak, explore the creek, or simply relax by the shore. The light-filled sunroom provides the perfect place to unwind while taking

    Judith Smith John C Ricotta & Assoc.

    78 Indian Trail, 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

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, South Chatham, North Chatham and East Harwich.
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