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Chatham, MA Homes for Sale

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  • 67 A Leonard Way, Chatham, MA 02633
    67 A Leonard Way, Chatham, MA 02633
    67 A Leonard Way, Chatham, MA 02633
    /50

    $975,000

    • 2 Beds
    • 2 Baths
    • 1,340 Sq Ft

    67 A Leonard Way, Chatham, MA 02633

    Welcome to 67 A Leonard Way, a charming ranch-style 2-bedroom home tucked away on a quiet street just minutes from downtown Chatham. Inside you'll find a beautifully renovated kitchen with granite countertops, stainless steel appliances and custom cabinetry. The open living and dining areas feature a fireplace, built-in shelving, and hardwood floors, creating a warm and inviting atmosphere. With

    Agent Photo

    Shane Masaschi

    Compass

    (508) 276-7761

    67 A Leonard Way, Chatham, MA 02633
  • 287 Cedar St, Chatham, MA 02633
    287 Cedar St, Chatham, MA 02633
    287 Cedar St, Chatham, MA 02633
    /74

    $4,395,000 Open Sun 10:30AM - 12PM

    • 3 Beds
    • 4.5 Baths
    • 3,640 Sq Ft

    287 Cedar St, Chatham, MA 02633

    NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island

    Agent Photo

    Shane Masaschi

    Compass

    (508) 290-5337

    287 Cedar St, Chatham, MA 02633
  • 39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    39 Meadow Brook Rd, Chatham, MA 02650
    /12

    $735,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    39 Meadow Brook Rd, Chatham, MA 02650

    Refreshed and Renewed... Don't miss this incredible opportunity to own a property in a prime Chatham location, just a short stroll from downtown. Enjoy nearby conservation hiking trails, the Cape Cod Rail Trail, and tennis courts, all within walking distance. Restaurants, shops, beaches, parks, and schools are also just a half-mile away. This home features a bright living room with a fireplace,

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    (508) 458-8396

    39 Meadow Brook Rd, Chatham, MA 02650
  • 9 Bettys Path, Chatham, MA 02633
    9 Bettys Path, Chatham, MA 02633
    9 Bettys Path, Chatham, MA 02633
    /39

    $1,700,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,008 Sq Ft

    9 Bettys Path, Chatham, MA 02633

    Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwork! This charming 3-bed, 2-bath home is nestled on a 1.8-acre lot, complete with a stunning kettle pond and a lush pastoral backdrop. Renovated in 2014, the home boasts a fresh roof and all the modern comforts. Step inside to find an inviting living room with a cozy fireplace, a dining room that opens onto a

    Agent Photo

    Shane Masaschi

    Compass

    (508) 682-4461

    9 Bettys Path, Chatham, MA 02633
  • 0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
    /6

    $250,000

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

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633

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

    Agent Photo

    Shane Masaschi

    Compass

    (508) 691-8324

    0 George Ryder Rd Unit 73104629, Chatham, MA 02633
  • 44 Buena Vista Rd, Chatham, MA 02633
    44 Buena Vista Rd, Chatham, MA 02633
    44 Buena Vista Rd, Chatham, MA 02633
    /52

    $8,500,000

    • 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) 400-2035

    44 Buena Vista Rd, Chatham, MA 02633
  • 10 Pursel Dr, North Chatham, MA 02650
    10 Pursel Dr, North Chatham, MA 02650
    10 Pursel Dr, North Chatham, MA 02650
    /52

    $1,999,999

    • 3 Beds
    • 2 Baths
    • 2,366 Sq Ft

    10 Pursel Dr, North Chatham, MA 02650

    WATER-VIEW & DEEDED ACCESS TO RYDERS COVE | ''Summer Wind'' - A Coastal Chatham RetreatNestled in one of Chatham's most cherished neighborhoods, ''Summer Wind'' is a timeless Cape Cod escape offering deeded access to Ryders Cove and a private association beach with direct access to Pleasant Bay. Perched gracefully above the water, this serene retreat delivers breathtaking views, impeccable

    Diane Donahue Gibson Sotheby's International Realty

    10 Pursel Dr, North Chatham, MA 02650
  • 335 Stage Island Rd, Chatham, MA 02633
    335 Stage Island Rd, Chatham, MA 02633
    335 Stage Island Rd, Chatham, MA 02633
    /67

    $4,950,000

    • 4 Beds
    • 5.5 Baths
    • 5,372 Sq Ft

    335 Stage Island Rd, Chatham, MA 02633

    Family-friendly home on Chatham's private Stage Island boasts captivating barrier beach and ocean views. This 10-room, 4-BR, 5.5-bath shingle-style home has 5,372 sf of living space designed for entertaining, indoors and out. The bright and airy 1st floor features a spacious great room with towering windows, a coffered ceiling, and Rumford fireplace. The kitchen boasts top-of-the-line appliances,

    Jack Bohman Gibson Sotheby's International Realty

    335 Stage Island Rd, Chatham, MA 02633
  • 45 Meadow View Rd S, Chatham, MA 02633
    45 Meadow View Rd S, Chatham, MA 02633
    45 Meadow View Rd S, Chatham, MA 02633
    /76

    $4,345,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 5.5 Baths
    • 4,908 Sq Ft

    45 Meadow View Rd S, Chatham, MA 02633

    New construction and a deeded boat slip in the Oyster River Hills private neighborhood marina. Another magnificent home by Sears Point Residential, move-in ready. 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape. The home's axis is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows seamlessly from the living room to the

    Jack Bohman Gibson Sotheby's International Realty

    45 Meadow View Rd S, Chatham, MA 02633
  • 17 Bucks Ln, Chatham, MA 02633
    17 Bucks Ln, Chatham, MA 02633
    17 Bucks Ln, Chatham, MA 02633
    /25

    $3,795,000

    • 4 Beds
    • 4 Baths
    • 3,030 Sq Ft

    17 Bucks Ln, Chatham, MA 02633

    This Chatham Beach House is calling...hope you answer.... Picture perfect Cape Cod style home with divine views over Nantucket Sound offers the idyllic Chatham beach lifestyle you have been dreaming of.....Steps to the private association beach of Harding's Shores for uncrowded enjoyment and warm water swimming. Classic 4BR 4 bath Cape home with two large decks for al fresco dining or morning

    Lori Fanning Smith Compass Massachusetts, LLC

    17 Bucks Ln, Chatham, MA 02633
  • 7 Squanto Dr, Chatham, MA 02633
    7 Squanto Dr, Chatham, MA 02633
    7 Squanto Dr, Chatham, MA 02633
    /76

    $3,295,000

    • 3 Beds
    • 3.5 Baths
    • 3,014 Sq Ft

    7 Squanto Dr, Chatham, MA 02633

    This Nantucket-style home features extraordinary views across a tidal salt marsh, Oyster Pond, and the 3 church steeples in Town. Enjoy the fireworks display New Year's Eve, ever-changing beauty of the seasons, and a host of wildlife from this elevated .69 acre site. With just over 3,000 square feet this exceptionally-crafted home is the perfect size; with an open floor plan ideal for

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    7 Squanto Dr, Chatham, MA 02633
  • 785 Old Harbor Rd, North Chatham, MA 02650
    785 Old Harbor Rd, North Chatham, MA 02650
    785 Old Harbor Rd, North Chatham, MA 02650
    /41

    $4,895,000

    • 5 Beds
    • 5 Baths
    • 4,200 Sq Ft

    785 Old Harbor Rd, North Chatham, MA 02650

    Welcome to " Two Stars" this meticulously crafted residence located in coveted North Chatham. This beautiful sanctuary offers an harmonious blend of luxury & comfort. Nestled on a lush acre with water views of Chatham harbor, this custom built masterpiece by master/builder owner invites you to experience refined living with every thoughtful detail. Spanning 4200sq. ft of sophisticated space, this

    Phyllis Power Compass

    785 Old Harbor Rd, North Chatham, MA 02650
  • 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

    $3,650,000

    • 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
  • 38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    38 Indian Trail, Chatham, MA 02633
    /44

    $4,950,000

    • 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
  • 104 Seapine Rd, North Chatham, MA 02650
    104 Seapine Rd, North Chatham, MA 02650
    104 Seapine Rd, North Chatham, MA 02650
    /46

    $2,750,000

    • 3 Beds
    • 3 Baths
    • 2,969 Sq Ft

    104 Seapine Rd, North Chatham, MA 02650

    Set within the coveted Harbor Coves Association of North Chatham, 104 Seapine Road is a rare opportunity to own in one of Cape Cod's most exclusive enclaves. With sweeping views over Crow's Pond and direct access to a private association beach just steps away, the setting is exceptional. Built in 1999 by noted local firm von Thaden Builders, the 3-bedroom, 2.5-bath home offers nearly 3,000 sq ft

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    104 Seapine Rd, North Chatham, MA 02650
  • 55 Winterset Dr, Chatham, MA 02633
    55 Winterset Dr, Chatham, MA 02633
    55 Winterset Dr, Chatham, MA 02633
    /68

    $2,445,000 Open Sat 12PM - 3PM

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

    55 Winterset Dr, Chatham, MA 02633

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

    Tara Schiffmann Brown Bayview Real Estate

    55 Winterset Dr, Chatham, MA 02633
  • 106 Stage Neck Rd, Chatham, MA 02633
    106 Stage Neck Rd, Chatham, MA 02633
    106 Stage Neck Rd, Chatham, MA 02633
    /41

    $2,699,000

    • 4 Beds
    • 3.5 Baths
    • 3,834 Sq Ft

    106 Stage Neck Rd, Chatham, MA 02633

    Nestled on just over an acre of meticulously landscaped grounds with a private well for irrigation near the Oyster River, this 4-bedroom, 3.5-bath home offers a rare opportunity to create your dream space. With deeded access to a small, shared boathouse, it provides a serene and sophisticated lifestyle. Built in 1987 and lovingly cared for, the home retains its classic charm and is ready for your

    Jen Graham Christie's International Real Estate Atlantic Brokerage

    106 Stage Neck Rd, Chatham, MA 02633
  • 36 Moonbeam Ln, Chatham, MA 02633
    36 Moonbeam Ln, Chatham, MA 02633
    36 Moonbeam Ln, Chatham, MA 02633
    /63

    $3,495,000

    • 4 Beds
    • 3.5 Baths
    • 4,857 Sq Ft

    36 Moonbeam Ln, Chatham, MA 02633

    This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborhood, and includes deeded rights to the Oyster Pond River. Immaculate and lightly used, you'll find 4,857 square feet of comfortable, casual elegance in a thoughtfully-designed floor plan. There are 4 spacious bedrooms including a lovely first-floor primary En-suite. Bright granite & stainless kitchen opens

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    36 Moonbeam Ln, Chatham, MA 02633
  • 290 Old Comers Rd, Chatham, MA 02633
    290 Old Comers Rd, Chatham, MA 02633
    290 Old Comers Rd, Chatham, MA 02633
    /40

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,603 Sq Ft

    290 Old Comers Rd, Chatham, MA 02633

    ''On Pink Wink Pond'' embodies the essence of Cape Cod. A startling entrance of Belgian blocks with carriage lighted and stone pillars greets the visitor. Ascending the farmers porch and upon entry, an illuminated tile mural of Pink Wink Pond boasts the home's attention to artistic detail. The two-story windowed great room is surrounded by crystal blue shiplap and offers a gas fireplace. Sub-Zero

    Catherine Baran Berkshire Hathaway HomeServices Robert Paul Properties

    290 Old Comers Rd, Chatham, MA 02633
  • 7 Bearberry Ln, South Chatham, MA 02659
    7 Bearberry Ln, South Chatham, MA 02659
    7 Bearberry Ln, South Chatham, MA 02659
    /56

    $925,000 Open Sun 11AM - 12PM

    • 3 Beds
    • 3 Baths
    • 1,328 Sq Ft

    7 Bearberry Ln, South Chatham, MA 02659

    Coastal charm near Cockle Cove Beach. This three bedroom three full bath home in South Chatham has been lovingly maintained and is located just a 1/2 mile to Cockle Cove Beach on Nantucket Sound. With just an easy drive to shopping, golf and more, this property would make a great rental, vacation home or primary home. Notable features include an updated kitchen, bright sunroom, wood burning

    Richard Robbins Compass

    7 Bearberry Ln, South Chatham, MA 02659
  • 24 Chickadee Cir, Harwich, MA 02645
    24 Chickadee Cir, Harwich, MA 02645
    24 Chickadee Cir, Harwich, MA 02645
    /41

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft

    24 Chickadee Cir, Harwich, MA 02645

    Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River with peeks of the water from the main bedroom, screened porch, and huge patio! Completely updated in '23/'24 with new exterior sheathing, siding, windows, doors, and refinished wood floors. The kitchen boasts new cabinetry, counters, and SS appliances. The bathrooms feature new tile floors, vanities, toilets,

    Amy Harbeck Kinlin Grover Compass

    24 Chickadee Cir, Harwich, MA 02645
  • 24 Chickadee Ln, Chatham, MA 02633
    24 Chickadee Ln, Chatham, MA 02633
    24 Chickadee Ln, Chatham, MA 02633
    /44

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,504 Sq Ft

    24 Chickadee Ln, Chatham, MA 02633

    Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River with peeks of the water from the main bedroom, screened porch, and huge patio! Completely updated in '23/'24 with new exterior sheathing, siding, windows, doors, and refinished wood floors. The kitchen boasts new cabinetry, counters, and SS appliances. The bathrooms feature new tile floors, vanities, toilets,

    Amy Harbeck Kinlin Grover Compass

    24 Chickadee Ln, Chatham, MA 02633
  • 30 Tisquantum Rd, Chatham, MA 02633
    30 Tisquantum Rd, Chatham, MA 02633
    30 Tisquantum Rd, Chatham, MA 02633
    /52

    $8,500,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    30 Tisquantum Rd, Chatham, MA 02633

    The first stop of the east wind and the morning sunrise , this elegant Cape Cod home offers an unparalleled living experience with sweeping views over the Atlantic Ocean, Stage Harbor and an enchanting salt marsh that leads to Nantucket Sound. This 5BR ,4.5 bath expanded shingled home offers a luxurious yet comfortable coastal lifestyle incorporating classic Cape Cod architectural styles with

    Lori Fanning Smith Compass Massachusetts, LLC

    30 Tisquantum Rd, Chatham, MA 02633
  • 98 Horizon Dr, Chatham, MA 02633
    98 Horizon Dr, Chatham, MA 02633
    98 Horizon Dr, Chatham, MA 02633
    /13

    $2,375,000

    • Land
    • 0.57 Acre
    • $4,166,667 per Acre

    98 Horizon Dr, Chatham, MA 02633

    New construction well underway with deeded rights to Lover's Lake for swimming, fishing and boating! Classic Cape Cod home sited high on a knoll with over 3000 s.f. spanning three levels with 3 BR's and 4.5 baths. Open floor plan offers great room with vaulted ceilings, fireplace and adjacent kitchen with center breakfast island and high end appliances .First floor primary suite with full bath

    Lori Fanning Smith Compass

    98 Horizon Dr, Chatham, MA 02633
  • 723 Main St, Chatham, MA 02633
    723 Main St, Chatham, MA 02633
    723 Main St, Chatham, MA 02633
    /14

    $1,000,000

    • Land
    • 0.16 Acre
    • $6,250,000 per Acre

    723 Main St, Chatham, MA 02633

    Town of Chatham officially assigned new street address 723 MAIN STREET! Take advantage of this last opportunity to build on a vacant lot on Main Street in downtown Chatham! This lot is 7,010 square feet (0.16 acres) located across from Chatham Veterans Field, home of the Chatham Anglers baseball team. This truly is the last opportunity to build on a vacant lot in downtown Chatham. For those who

    Matthew Burger Kinlin Grover Compass

    723 Main St, Chatham, MA 02633
  • 2016 Main St, Chatham, MA 02633
    2016 Main St, Chatham, MA 02633
    2016 Main St, Chatham, MA 02633
    /95

    $2,150,000

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

    2016 Main St, Chatham, MA 02633

    Stunning Magazine-Quality Home with Resort-Style Living on Main StreetTucked privately off Main Street, this breathtaking home offers the perfect balance of privacy and prime location. Designed for both relaxed living and stylish entertaining, the interior boasts an open floor plan with beautiful shiplap walls, a dedicated dining room with built-in wet bar, and a thoughtfully placed half bath

    Daneen Law Gibson Sotheby's International Realty

    2016 Main St, Chatham, MA 02633
  • 108 Shore Rd, Chatham, MA 02633
    108 Shore Rd, Chatham, MA 02633
    108 Shore Rd, Chatham, MA 02633
    /32

    $11,900,000

    • 7 Beds
    • 9 Baths
    • 6,276 Sq Ft

    108 Shore Rd, Chatham, MA 02633

    Located along Chatham’s transcendent shoreline, this elegant coastal estate includes a Main House, a Guest House with a 3 car garage, and a waterfront Boat House/Cabana. Surrounded by beautiful hardscape, the Colonial style Main Residence has been rebuilt with a modern, open floor plan designed for entertaining. Spectacular views of Chatham Harbor and the Atlantic abound. The Main House features

    Frank Denauw Frank G. Denauw, Esq.

    108 Shore Rd, Chatham, MA 02633
  • 15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    /32

    $1,075,000

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

    15 Sylvan Way, South Chatham, MA 02659

    Nestled in charming Chatham in a neighborhood of higher-end homes—this beautifully maintained coastal-style home blends timeless charm with modern upgrades. A graceful central staircase leads to a rooftop deck, evoking the classic appeal of historic sea captain homes. The interior features high-end European appliances (Fisher & Paykel & Blomberg), granite countertops, newer bathrooms, Roman

    Pauline Teas William Raveis Chatham

    15 Sylvan Way, South Chatham, MA 02659
  • 597 Orleans Rd, North Chatham, MA 02650
    597 Orleans Rd, North Chatham, MA 02650
    597 Orleans Rd, North Chatham, MA 02650
    /76

    $1,445,000

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

    597 Orleans Rd, North Chatham, MA 02650

    Nestled on a sprawling 1.55-acre parcel set back from Route 28, this exquisite North Chatham residence captures the essence of tranquil coastal living. This beautifully renovated home spans 1,942 square feet (including the beautiful finished walkout lower level) and boasts three spacious bedrooms and two pristine bathrooms, offering an exceptional blend of comfort and sophistication.
As you

    Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650
  • 92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    92 Barcliff Ave, Chatham, MA 02633
    /53

    $3,750,000

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

    $6,750,000

    • 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
  • 1761 Main St, Chatham, MA 02633
    1761 Main St, Chatham, MA 02633
    /2

    $659,000

    • Land
    • 1.01 Acres
    • $652,475 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

    Kimberly Clark Bayside Realty Consultants

    1761 Main St, Chatham, MA 02633
  • 150 Barcliff Ave, Chatham, MA 02633
    150 Barcliff Ave, Chatham, MA 02633
    150 Barcliff Ave, Chatham, MA 02633
    /43

    $4,200,000

    • 6 Beds
    • 4 Baths
    • 3,808 Sq Ft

    150 Barcliff Ave, Chatham, MA 02633

    Chatham: where hydrangeas meet the sea and harbors merge into the ocean. A place where cherished memories are created and passed on through generations. If you've been dreaming of living in this storybook town, just a short stroll from sandy beaches and its vibrant Village, you've arrived. Welcome to 150 Barcliff Avenue. Tucked along one of Chatham's most picturesque streets, this updated home

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    150 Barcliff Ave, Chatham, MA 02633
  • 116 Happy Valley Rd, Chatham, MA 02633
    116 Happy Valley Rd, Chatham, MA 02633
    116 Happy Valley Rd, Chatham, MA 02633
    /45

    $1,399,500

    • 2 Beds
    • 3 Baths
    • 1,861 Sq Ft

    116 Happy Valley Rd, Chatham, MA 02633

    Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway. 1st level open plan features brk bar & dining/living area with views to the bog pond. Door to south facing deck setup for dining & and all day sun. 2 entry kitchen with granite counters & stainless

    Ward Brown William Raveis Real Estate & Home Services

    116 Happy Valley Rd, Chatham, MA 02633
  • 355 Training Field Rd, Chatham, MA 02633
    355 Training Field Rd, Chatham, MA 02633
    355 Training Field Rd, Chatham, MA 02633
    /40

    $1,475,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 2,225 Sq Ft

    355 Training Field Rd, Chatham, MA 02633

    Just 8/10 of a mile to Jackknife Point BeachThis beautifully appointed Chatham retreat offers the perfect blend of comfort, style, and solar efficiency. A charming farmer’s porch welcomes you into a light-filled home with high ceilings, an open layout, and a skylit kitchen with granite counters, stainless steel appliances, and a large island. The living room features a cozy gas fireplace, and the

    Margaret McDonald Mathieu Newton Sotheby's International Realty

    355 Training Field Rd, Chatham, MA 02633
  • 25 Wikis Way, Chatham, MA 02633
    25 Wikis Way, Chatham, MA 02633
    25 Wikis Way, Chatham, MA 02633
    /32

    $5,900,000

    • 4 Beds
    • 4.5 Baths
    • 4,654 Sq Ft

    25 Wikis Way, Chatham, MA 02633

    TIMELESS COASTAL LUXURY // Prepare to be embraced by one of the most breathtaking panoramas in all of Cape Cod. This exceptional property offers sweeping and unobstructed views that stretch from Stage Harbor and the iconic Chatham Lighthouse, to the natural beauty of Monomoy Island and the sparkling expanse of the Atlantic Ocean. From first light until sunset, this coastal retreat is surrounded

    Chris Rhinesmith Compass Massachusetts, LLC

    25 Wikis Way, Chatham, MA 02633
  • 319 Riverview Dr, Chatham, MA 02633
    319 Riverview Dr, Chatham, MA 02633
    319 Riverview Dr, Chatham, MA 02633
    /28

    $1,300,000

    • 3 Beds
    • 3 Baths
    • 2,202 Sq Ft

    319 Riverview Dr, Chatham, MA 02633

    Sited on nearly an acre of land in Riverbay Estates, this spacious three bedroom, three bath home offers ample privacy and outdoor living space.Built in 1984 with an addition and updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite withgas fireplace, walk in closet, and outdoor access. The kitchen features abundant cabinet

    Chris Rhinesmith Compass

    319 Riverview Dr, Chatham, MA 02633
  • 292 Stage Harbor Rd, Chatham, MA 02633
    292 Stage Harbor Rd, Chatham, MA 02633
    292 Stage Harbor Rd, Chatham, MA 02633
    /29

    $2,300,000

    • 3 Beds
    • 4.5 Baths
    • 1,834 Sq Ft

    292 Stage Harbor Rd, Chatham, MA 02633

    Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to the center of Chatham Village sits this exceptional 3 bedroom 4 bath custom Farmhouse with inviting front porch built in 2018. Hardwood floors thruout and, formal dining area, custom kitchen along with an office for those working remotely. Home has central a/c and a gas stove in the Livingroom. The lower

    Ward Brown William Raveis Real Estate & Home Services

    292 Stage Harbor Rd, Chatham, MA 02633
  • 213 Main St, Chatham, MA 02633
    213 Main St, Chatham, MA 02633
    213 Main St, Chatham, MA 02633
    /30

    $2,300,000

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

    213 Main St, Chatham, MA 02633

    Location! Location in the heart of Chatham! Historic Greek Revival circa 1850's in the Old Village, with water views of Chatham Harbor, Andrew Harding's landing and Lighthouse beach & Main St shopping/dining, Band Concerts, nearby! This charming 4 bed/2 bath home has a sunny eat-in beamed family room with sliders to deck, cozy kitchen adjacent and a front Living room with gas fireplace, warm

    Phyllis Power Compass

    213 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

Is Chatham, MA a safe city?
In general, the safest neighborhoods in Chatham, MA with lower crime scores are South Chatham, Chatham Village 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 near Chatham, MA?
The most popular neighborhoods near Chatham, MA are Chatham Village, South Chatham, North Chatham, Harwich Center and Northwest Harwich.
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