82

Chatham, MA Homes for Sale

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  • /47

    $1,650,000

    • 3 Beds
    • 2.5 Baths
    • 2,430 Sq Ft

    70 Lantern Ln, South Chatham, MA 02659

    Discover your dream home just a short stroll to Cockle Cove Beach! Incredible spot...Tucked away at the end of a private lane, this 3 bedroom 2 1/2 bath home with long leaf yellow pine floors throughout the first floor has plenty of living space for family and friends. Surrounded by an expansive wrap-around deck, the open concept first floor is highlighted by the living room with wood burning

    Judith Smith John C Ricotta & Assoc.

    70 Lantern Ln, South Chatham, MA 02659
  • /40

    $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
  • /43

    $9,950,000

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

    113 Seapine Rd, North Chatham, MA 02650

    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 Massachusetts, LLC

    113 Seapine Rd, North Chatham, MA 02650
  • /19

    $399,000

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

    Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal gateway to the Chatham lifestyle. This ground-floor 1-bedroom, 1-bathroom condominium is a rare find, blending convenience, charm, and investment potential. Whether you're seeking a turnkey rental, seasonal getaway, or an easy-care year-round home, this residence delivers on every front. Inside, the unit is

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
  • /23

    $399,000

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft

    109 Misty Meadow Ln, North Chatham, MA 02650

    Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal gateway to the Chatham lifestyle. This ground-floor 1-bedroom, 1-bathroom condominium is a rare find, blending convenience, charm, and investment potential. Whether you're seeking a turnkey rental, seasonal getaway, or an easy-care year-round home, this residence delivers on every front.Inside, the unit is

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln, North Chatham, MA 02650
  • /27

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    109 Misty Meadow Ln, 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

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln, North Chatham, MA 02650
  • /33

    $1,595,000

    • 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

    $1,595,000

    • 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
  • /65

    $749,900

    • 5 Beds
    • 3 Baths
    • 2,184 Sq Ft

    2590 Main St, South Chatham, MA 02659

    In the heart of South Chatham, just moments from Forest Road Beach, this versatile 5-bedroom, 3-bathroom antique home offers endless possibilities. Built in 1834, yet, designed for dual-unit living, the property is perfect for multi-generational families, rental income, or easily converting into a spacious single-family retreat.Sitting on a 6-bedroom septic system, this home provides potential

    Richard Waystack William Raveis Real Estate & Home Services

    2590 Main St, South Chatham, MA 02659
  • /25

    $899,900

    • 3 Beds
    • 3 Baths
    • 1,492 Sq Ft

    25 Crosby Ln, Chatham, MA 02633

    TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best

    Amanda Bender Christie's International Real Estate Atlantic Brokerage

    25 Crosby Ln, Chatham, MA 02633
  • /25

    $899,900

    • 3 Beds
    • 3 Baths
    • 1,492 Sq Ft

    25 Crosby Ln, Chatham, MA 02633

    TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best

    Amanda Bender Christie's International Real Estate Atlantic Brokerage

    25 Crosby Ln, Chatham, MA 02633
  • /41

    $997,000

    • 2 Beds
    • 3 Baths
    • 2,399 Sq Ft

    1082 Main St Unit 1082, Chatham, MA 02633

    Motivated sellers! Come take a look at this turn key, end unit townhome in beautiful Chatham! This serene setting overlooks Perch Pond where nature abounds.This 3 level townhome has an attached garage and private driveway, an extra "flex space" room on the 2nd level (could be an office, art studio, gym, 3rd bedroom, etc) and a finished lower level w/ large great room & full bath. This complex is

    Kristin Coletti William Raveis R.E. & Home Services

    1082 Main St Unit 1082, Chatham, MA 02633
  • /36

    $495,000

    • 1 Bed
    • 1 Bath
    • 578 Sq Ft

    Unlisted Address

    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

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    Unlisted Address
  • /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

    425 Main St Unit D, Chatham, MA 02633
  • /8

    $349,900

    • Land
    • 0.47 Acre
    • $744,468 per Acre

    0 Tirrells Way, Chatham, MA 02659

    Building lot available! Located at the end of a cul-de-sac and abutting the Town Forest. Water Department has an easement for a road over the property at the edge of the lot boundary. All due diligence required for building allowances and restrictions are responsibility of the buyer.

    Kathy Doyle Gibson Sotheby's International Realty

    0 Tirrells Way, Chatham, MA 02659
  • /42

    $5,400,000

    • 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 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, coffered ceiling, and Rumford fireplace. The kitchen boasts a large center island, custom wet bar, and butler’s

    335 Stage Island Rd, Chatham, MA 02633
  • /24

    $740,000

    • Land
    • 1.01 Acres
    • $732,673 per Acre

    1761 Main St, Chatham, MA 02633

    Price reduction! Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house or 2 houses on this 1 acre lot that backs up to a cranberry bog. This lot has potential view of the cranberry bog and is very close to Ridgevale beach. If you are looking to build a large home with a guest house and a pool or even 2 houses; this lot has

    Kathleen Phelan Compass Massachusetts, LLC

    1761 Main St, Chatham, MA 02633
  • /21

    $740,000

    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft

    1761 Main St, Chatham, MA 02633

    Price reduction! Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house or 2 separate houses on this 1 acre lot that backs up to a cranberry bog. The lot has sewer hook up in front of the house. This lot has potential view of the cranberry bog and is very close to Ridgevale beach. If you are looking to build a large home with a

    Kathleen Phelan Compass Massachusetts, LLC

    1761 Main St, Chatham, MA 02633
  • /10

    $775,000

    • 2 Beds
    • 1 Bath
    • 572 Sq Ft

    82 Diane Dr, Chatham, MA 02633

    The 4th of July is less than 6 months away! Here is a rare opportunity to be a stone's throw from Ridgevale Beach with private association access via the Buck's Creek Association bridge. This 2-bedroom cape style cottage is ready for rehab, or a total rebuild. It sits on an elevated bluff and is not in the Flood Zone. Abutting conservation land, the site offers plenty of privacy and has great

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    82 Diane Dr, Chatham, MA 02633
  • /14

    $1,000,000

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

    727 Main St, Chatham, MA 02633

    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 dreamed of building a home with a sense of community, who enjoy Chatham's

    Matthew Burger Kinlin Grover Compass

    727 Main St, Chatham, MA 02633
  • /39

    $6,995,000

    • 7 Beds
    • 8.5 Baths
    • 7,111 Sq Ft

    114 Cranberry Ln, North Chatham, MA 02650

    Sited on a picturesque lane in a coveted North Chatham location, this custom estate home with deeded access to a private sandy beach on Pleasant Bay is being offered fully furnished and turn key!! Featuring the absolute best of coastal Cape Cod living, the 5+ bedroom Main House and 2 bedroom Guest House are like new, having been further improved and maintained to exacting standards. Thoughtfully

    Brian Dougherty Corcoran Property Advisors

    114 Cranberry Ln, North Chatham, MA 02650
  • /42

    $1,635,000

    • 3 Beds
    • 2.5 Baths
    • 2,310 Sq Ft

    315 Pleasant St, South Chatham, MA 02659

    Chatham - The salt waters of Nantucket Sound greet you instantly here at 315 Pleasant Street! This is a rare opportunity to live high and dry and a mere 350 yards from one of the finest and best stretches of sandy beach on Nantucket Sound. 315 Pleasant Street has been lovingly maintained and recently improved and upgraded by the current owners. Enjoy water views from the primary bedroom's

    Ritu Chawla Gibson Sotheby's International Realty

    315 Pleasant St, South Chatham, MA 02659
  • /23

    $2,950,000

    • 7 Beds
    • 3 Baths
    • 2,460 Sq Ft

    30 Mill Hill Ln, Chatham, MA 02633

    Rare and unique opportunity to own a classic Cape Cod compound in Chatham's iconic Old Village. Tucked at the end of a quiet lane just moments to town, lighthouse and beach. This hide-a-away compound built in 1840 consists of a four bedroom main house, three bedroom guest cottage and a small carriage house currently used as a workshop with a lively history as a neighborhood entertainment venue.

    Chris Rhinesmith Compass Massachusetts, LLC

    30 Mill Hill Ln, 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
  • /41

    $4,400,000

    • 5 Beds
    • 8 Baths
    • 5,578 Sq Ft

    67 Uncle Alberts Dr, Chatham, MA 02633

    This impressive home sited on 2.07 acres on a quiet cul-de-sac is just a few minutes away from restaurants, the Chatham bike path and nearby Chatham beaches. The 2014 Eastward Companies home offers a tremendous sense of living space spanning 5,578 square feet and defined by lovely grounds, water views, luxurious finishes and a sweeping open floor plan. The main level flows seamlessly between the

    Chris Rhinesmith Compass

    67 Uncle Alberts Dr, Chatham, MA 02633
  • /50

    $4,400,000

    • 5 Beds
    • 8 Baths
    • 5,578 Sq Ft

    67 Uncle Alberts Dr, Chatham, MA 02633

    NEWLY REDUCED! Space, Luxury, Convenience! This impressive home, situated on 2.07 acres in a quiet cul-de-sac, is just minutes away from restaurants, the Chatham bike path, and nearby Chatham beaches. Built by Eastward Companies in 2014, this home offers a tremendous sense of living space, spanning 5,578 square feet, and is defined by lovely grounds, water views, luxurious finishes, and a

    Chris Rhinesmith Compass Massachusetts, LLC

    67 Uncle Alberts Dr, Chatham, MA 02633
  • /75

    $4,750,000

    • 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 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

    Jack Bohman Gibson Sotheby's International Realty

    45 Meadow View Rd S, Chatham, MA 02633
  • /39

    $4,395,000

    • 3 Beds
    • 3 Baths
    • 2,418 Sq Ft

    30 Indian Trail, Chatham, MA 02633

    Nestled in Hardings Beach Hills, Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, presents a stunning display of nature with its panoramic marsh and creek views. The architecture of this residence is a masterful fusion of classic Cape vernacular with modern inspiration, reflective of PSD's signature style. Unique design elements and extraordinary millwork details, like the

    Chris Rhinesmith Compass Massachusetts, LLC

    30 Indian Trail, Chatham, MA 02633
  • /11

    $3,499,900

    • 3 Beds
    • 4.5 Baths
    • 4,620 Sq Ft

    33 Jessie's Landing, Chatham, MA 02633

    Get ready for summer and enjoy the saltwater pool, spa and firepit! A new residence is in progress by Eastward Companies, showcasing exquisite details and finishes. This beautifully designed home spans over 4,600 sq. ft. and checks off many items on everyone's wish list. It features a spacious open floor plan, a gourmet kitchen with a butler's pantry, and a first-floor master suite, making it

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    33 Jessie's Landing, 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
  • /15

    $399,900

    • Land
    • 0.28 Acre
    • $1,428,214 per Acre

    0 Victoria Dr, Chatham, MA 02633

    Build your dream home on this beautiful lot nestled on a cul de sac in desirable Chatham. Septic design, engineering, and wind and energy plan are done. Town water, gas and electric are on the street. Seller currently has plans for a 1700 square foot, two bedroom, two and a half bath Cape with two car garage.

    Caroline McAdams Covell Realty Inc

    0 Victoria Dr, Chatham, MA 02633
  • /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
  • /43

    $1,850,000

    • 6 Beds
    • 4.5 Baths
    • 2,665 Sq Ft

    14 Squanto Dr, Chatham, MA 02633

    Perched high above the Oyster River with stunning water views and deeded river access for your paddling and boating adventures, 14 Squanto Drive is your new Chatham beach oasis. Offering a relaxed coastal lifestyle, this home boasts open sight lines, sundrenched living spaces, ideal flow for indoor/outdoor entertaining, and an abundance of room for extended families and guests. From sunrise to

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    14 Squanto Dr, Chatham, MA 02633
  • /4

    $265,500

    • Land
    • 0.72 Acre
    • $368,750 per Acre

    0 George Ryder Rd Unit 22301591, 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, with approvals a 4-bedroom may be possible. Buyer's & buyer brokers verify sewer regulations with Board of Health as rules continue to change. The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to

    0 George Ryder Rd Unit 22301591, 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
  • /23

    $399,000

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
  • /26

    $475,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650

    109 Misty Meadow Ln Unit 4, North Chatham, MA 02650
  • /3

    $1,295,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    0 Victoria Dr, Chatham, MA 02633

    Build your dream home on this beautiful lot nestled on a cul de sac in desirable Chatham. Septic design, engineering and wind and energy plan are done. Town water and gas and electric are on the street.Building packages for a Cape and Ranch are available. Capes are approximately 2400 square feet with 2.5 baths and one or two car garage. Could also be customized and price will depend on level of

    Caroline McAdams Covell Realty Inc

    0 Victoria Dr, Chatham, MA 02633
  • /48

    $6,995,000 New Construction

    • 5 Beds
    • 6.5 Baths
    • 6,508 Sq Ft

    16 Seapine Rd, North Chatham, MA 02650

    This exceptional custom residence currently under construction is situated in a prime North Chatham location with a nearby association beach. Seamlessly blending comfort and sophistication, the home spans three levels of generous open floor plan spaces and is located on over one acre. The main level interiors flow freely from foyer to a large great room with a living room, dining area and well

    Chris Rhinesmith Compass Massachusetts, LLC

    16 Seapine Rd, North Chatham, MA 02650
  • /12

    $3,499,900 New Construction

    • 3 Beds
    • 4.5 Baths
    • 4,620 Sq Ft

    33 Jessies Landing, Chatham, MA 02633

    Get ready for summer and enjoy the saltwater pool, spa and firepit! A new residence is in progress by Eastward Companies, showcasing exquisite details and finishes. This beautifully designed home spans over 4,600 sq. ft. and checks off many items on everyone's wish list. It features a spacious open floor plan, a gourmet kitchen with a butler's pantry, and a first-floor master suite, making it

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    33 Jessies Landing, Chatham, MA 02633

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