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Waterfront Homes for Sale in Chatham, MA

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  • /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
  • /52

    $8,500,000

    • 7 Beds
    • 6.5 Baths
    • 6,521 Sq Ft

    Unlisted Address

    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

    Unlisted Address
  • /27

    $3,895,000

    • 4 Beds
    • 4 Baths
    • 3,000 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

    17 Bucks Ln, Chatham, MA 02633
  • /42

    $7,299,000

    • 4 Beds
    • 5 Baths
    • 4,214 Sq Ft

    12 Pond St, Chatham, MA 02633

    Home in Chatham Village. 4-bedroom, 5-bathroom located just steps from Oyster Pond and sandy beach. Features include open floor plan, high ceilings, hardwood floors, and expansive water views. Enjoy deeded access to association dock and mooring field. The kitchen offers stone countertops, large center island, and premium appliances, flowing into a dining and living area with fireplace—ideal for

    Tim Bailey John C. Ricotta & Associates, Inc.

    12 Pond St, Chatham, MA 02633
  • /42

    $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 summer breezes from this 3 BR, 4.5 Bath, 4,361 sf home with a private deeded footpath to Stage Harbor. Thoughtfully designed to capture harbor and wetland views, the house features vaulted ceilings, an abundance of windows, hardwood floors and an open floor plan that

    The Bohman Hartung Group Gibson Sotheby's International Realty

    86 Champlain Rd, 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
  • /42

    $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 & Associates, Inc.

    15 Windy Hill Way, Chatham, MA 02633
  • /37

    $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

    85 Main St, Chatham, MA 02633
  • /36

    $7,200,000

    • 5 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    238 Cranberry Ln, Chatham, MA 02633

    This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, Chatham, MA 02633
  • /38

    $6,500,000

    • 5 Beds
    • 6.5 Baths
    • 5,143 Sq Ft

    4 Ministers Ln, North Chatham, MA 02650

    MAJESTIC SEASIDE LIVING. This unrivaled oceanfront estate located on prestigious Ministers Point in North Chatham offers grand scale living with dramatic Atlantic Ocean vistas. The meticulously designed cedar shingle and sprawling stone exteriors seamlessly blend the elegant interiors that boast striking architectural details, custom finishes and the highest quality craftsmanship. The 11 rooms

    Chris Rhinesmith Compass Massachusetts, LLC

    4 Ministers Ln, North Chatham, MA 02650
  • /42

    $9,950,000

    • 4 Beds
    • 5.5 Baths
    • 3,504 Sq Ft

    113 Seapine, Chatham, MA 02635

    Designed by the award-winning architectural firm Polhemus Savery DaSilva, this waterfront masterpiece has been refined with elevated finishes by renowned designer Lisa Tharp. Set on Crows Pond, the open-concept main level showcases breathtaking water views from the stunning chef's kitchen and great room with open dining area, all seamlessly flowing to a screened porch, expansive stone patio,

    Chris Rhinesmith Compass

    113 Seapine, Chatham, MA 02635
  • /42

    $4,345,000 Open Sat 11AM - 1PM

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

    45 Meadow View Rd S, Chatham, MA 02633

    NEW CONSTRUCTION Another magnificent home by Sears Point Residential is now move-in ready. This 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape is just steps from your deeded boat slip in the Oyster River Hills private neighborhood marina. The heart of the home is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows

    The Bohman Hartung Group Gibson Sotheby's International Realty

    45 Meadow View Rd S, Chatham, MA 02633
  • /41

    $3,295,000

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

    7 Squanto Dr, Chatham, MA 02633

    Open House Saturday! 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 sq' this exceptionally-crafted home is the perfect size; with an open floor plan ideal

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    7 Squanto Dr, Chatham, MA 02633
  • /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
  • /45

    $1,399,500 Open Sat 9AM - 11PM

    • 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
  • /42

    $2,750,000

    • 3 Beds
    • 2.5 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

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    104 Seapine Rd, North Chatham, MA 02650
  • /38

    $1,599,000

    • 3 Beds
    • 3.5 Baths
    • 3,050 Sq Ft

    46 Juniper Ln W, Chatham, MA 02659

    ''Moongazer'' represents a rare opportunity to purchase a thoughtfully updated, proven income producing property with deeded access to Taylor's Pond where it is a fun and easy kayak or paddle board out to Nantucket Sound and the beach. This 3,150 sf home offers far more living space and room for overflow guests than meets the eye. Upon entering, you will be wowed by the soaring ceilings,

    The Bohman Hartung Group Gibson Sotheby's International Realty

    46 Juniper Ln W, Chatham, MA 02659
  • /53

    $1,400,000

    • 4 Beds
    • 3 Baths
    • 2,391 Sq Ft

    68 Chippingstone Rd, Chatham, MA 02633

    Ideal rental investment property in Riverbay Estates! Enjoy water views and direct access to Pickerel Pond from this 4-bed, 3-bath home perfect for kayaking and paddleboarding. Features include a first-floor primary suite, living and dining areas with pond views, central A/C, gas heat, and an attached two-car garage. The home is generator ready with a panel for the transfer switch already in

    Marcia Thorngate Smith Christie's International Real Estate Atlantic Brokerage

    68 Chippingstone Rd, Chatham, MA 02633
  • /45

    $9,950,000

    • 4 Beds
    • 5.5 Baths
    • 5,850 Sq Ft

    113 Seapine Rd, North Chatham, MA 02650

    Designed by award-winning firm Polhemus Savery DaSilva and enhanced by designer Lisa Tharp, this waterfront masterpiece embodies timeless coastal luxury. Perfectly sited on Crows Pond, the open-concept main level captures stunning water views from every angle--including the chef's kitchen, great room, and dining area. These spaces open to a screened porch, stone patio, infinity pool, and

    Chris Rhinesmith Compass Massachusetts, LLC

    113 Seapine Rd, North Chatham, MA 02650
  • /33

    $1,450,000

    • 3 Beds
    • 2.5 Baths
    • 1,144 Sq Ft

    552 Orleans Rd, Chatham, MA 2633

    Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning

    Chris Rhinesmith Compass

    552 Orleans Rd, Chatham, MA 2633
  • /32

    $1,450,000

    • 3 Beds
    • 2.5 Baths
    • 1,144 Sq Ft

    552 Orleans Rd, North Chatham, MA 02650

    Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning

    Chris Rhinesmith Compass Massachusetts, LLC

    552 Orleans Rd, North Chatham, MA 02650
  • /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
  • /32

    $1,469,000

    • 5 Beds
    • 10 Baths
    • 11,000 Sq Ft

    558 Fox Hill Rd, Chatham, MA 02633

    New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and

    John DePreaux Corcoran Property Advisors

    558 Fox Hill Rd, Chatham, MA 02633
  • /9

    $13,950,000

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

    301 Whidah Rd, Chatham, MA 02650

    Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay. Take the stairs to the water and enjoy your own private beach and

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    301 Whidah Rd, Chatham, MA 02650
  • /90

    $13,950,000

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

    301 Whidah Rd, North Chatham, MA 2650

    Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay. Take the stairs to the water and enjoy your own private beach and

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    301 Whidah Rd, North Chatham, MA 2650
  • /42

    $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

    Tim Bailey John C. Ricotta & Associates, Inc.

    150 Cross St, Chatham, MA 02633
  • /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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