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Chatham Village Homes for Sale

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  • /69

    $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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /46

    $4,600,000

    • 3 Beds
    • 3.5 Baths
    • 2,998 Sq Ft

    85 Main St, Chatham, MA 02633

    OFFERED FULLY FURNISHED INCLUDING ALL CONTENTS SO YOU CAN MOVE RIGHT IN! // Ideally situated in one of Chatham's most sought-after enclaves, just steps from iconic Lighthouse Beach, this exceptional home is rich in character and timeless charm. Beautifully maintained, it offers sun-filled, spacious interiors that transition seamlessly between formal elegance and casual comfort.The thoughtfully

    Chris Rhinesmith Compass Massachusetts, LLC

    85 Main St, Chatham, MA 02633
  • /34

    $7,250,000

    • 10 Beds
    • 10 Baths
    • 8,000 Sq Ft

    150 Cross St, Chatham, MA 02633

    Beautiful Chatham Georgian estate on 1.3 acres within walking distance to the center of town, Oyster Pond beach and all the amenities Chatham has to offer. Spectacular sunset views of the Oyster Pond, rolling lawns, bluestone patios and specimen landscaping surround this magnificent estate in the heart of downtown. Comprised of 10 bedrooms, 7 fireplaces, 7 full and 3 half baths, elevator and

    John Ricotta John C Ricotta & Assoc.

    150 Cross St, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /35

    $495,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    425 Main St Unit D, Chatham, MA 02633

    Nestled above Bumbula "It's All About Me", Unit D at 425 Main Street offers an unparalleled lifestyle in the heart of Chatham. This 1-bedroom, 1-bathroom residence blends sophisticated comfort with modern convenience, making it the ideal year-round home or refined retreat. With a private, discreet entrance, this second-floor sanctuary is one of only two residences on this level.Designed for

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    425 Main St Unit D, Chatham, MA 02633
  • /42

    $1,995,000

    • 1 Bed
    • 1.5 Baths
    • 1,479 Sq Ft

    409 Main St, Chatham, MA 02633

    Location-Location-409 Main St. in Downtown Chatham offers you this very rare and desirable combination of a mixed use building with a 1st floor highly visible commercial space with showcase windows, maximum retail exposure and high foot traffic, as well as a fully renovated spacious apartment on the 2nd floor in the heart of Chatham Village. The property offers 5 private in-town parking spaces

    Rick Smith Gibson Sotheby's International Realty

    409 Main St, Chatham, MA 02633
  • /27

    $1,750,000

    • 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
  • /2

    $6,995,000 New Construction

    • 5 Beds
    • 7 Baths
    • 5,700 Sq Ft

    13 Captain Knowles Way, Chatham, MA 02633

    Experience the perfect blend of luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship throughout.Designed for both comfort and entertaining, the home

    Mina O'Keefe Gibson Sotheby's International Realty

    13 Captain Knowles Way, Chatham, MA 02633
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