Chatham, MA Homes

• 

  

  

  /25

  Est $816,334 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 966 Sq Ft

  161 Shane Dr, Chatham, MA 02633

  161 Shane Dr, Chatham, MA 02633
• 

  

  

  /48

  $4,900,000

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

  85 Main St, Chatham, MA 02633

  OFFERED FULLY FURNISHED AND READY FOR SUMMER OCCUPANCY // INCLUDES 1970 FORD BRONCO 302 COYOTE. 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

  Chris Rhinesmith Compass Massachusetts, LLC

  85 Main St, Chatham, MA 02633
• 

  

  

  /35

  $1,599,000 Sold Feb 24, 2025

  • 1,511 Sq Ft
  • $1058/SF
  • 7 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1940

  101 Old Mail Rd, North Chatham, MA 02650

  Sited in one of North Chatham's most sought-after areas on a 1/2 acre lot, this recently renovated custom home sets the bar on luxurious living. This 3 BR, 2 BA home is rich in architectural design with crown molding, shiplap ceilings and walls, and gorgeous 4-inch white oak floors throughout. This open and circular one-floor living space has an expansive feel with a gas fireplace including chefs

  Jessica King Compass Massachusetts, LLC

  101 Old Mail Rd, North Chatham, MA 02650
• 

  

  

  /46

  Est $1,425,052 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,491 Sq Ft

  265 Barcliff Ave, Chatham, MA 02633

  265 Barcliff Ave, 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
• 

  

  /59

  $1,200,000 Sold Feb 24, 2025

  • 1,617 Sq Ft
  • $742/SF
  • 256 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1995

  1174 Old Queen Anne Rd, Chatham, MA 02633

  First time on the market! Experience coastal living surrounded by conservation areas and stunning sunsets. This remarkable Chatham year-round retreat spans 2.1 acres with views along Monomoy River. The main house features single-story living with two bedrooms, cozy living areas, bonus area and captivating outdoor garden spaces. The late 1800's original cottage offers the opportunity to be a

  Paul McCormick Gibson Sotheby's International Realty

  1174 Old Queen Anne Rd, Chatham, MA 02633
• 

  

  /24

  Est $3,669,151 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,421 Sq Ft

  125 Stage Harbor Rd, Chatham, MA 02633

  125 Stage Harbor Rd, Chatham, MA 02633
• 

  

  /4

  $315,000

  • Land
  • 1.07 Acres
  • $294,393 per Acre

  2386 Main St, South Chatham, MA 02659

  This 1.069 acre lot is zoned R20 and partially R60. Great location close to the beach and bike trail. Buyer and their agent to do their own due diligence. Please verify all information contained herein.

  Judith Smith John C Ricotta & Assoc.

  2386 Main St, South Chatham, MA 02659
• 

  

  /46

  $4,000,000 Sold Feb 21, 2025

  • 4,195 Sq Ft
  • $954/SF
  • 2 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2004

  43 Chatham Heights Rd, Chatham, MA 02633

  On a tucked away street near town, beaches and some of Chatham favorite restaurants, this private hideaway on 1.4 acres transports you to a serene and sun-infused getaway overlooking a lush landscape of greenery and sparkling pond views. Custom design detail, soothing color palette and a sophisticated open floor plan make this home truly unique. A generous great room is anchored by a wood burning

  Chris Rhinesmith Compass Massachusetts, LLC

  43 Chatham Heights Rd, Chatham, MA 02633
• 

  

  /62

  Est $2,385,224 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,732 Sq Ft

  276 Stage Harbor Rd, Chatham, MA 02633

  276 Stage Harbor Rd, Chatham, MA 02633
• 

  

  /58

  $1,750,000

  • 4 Beds
  • 3 Baths
  • 1,990 Sq Ft

  235 Training Field Rd, Chatham, MA 02633

  NEED AN IN-LAW APARTMENT? Tucked away from the road in desirable Riverbay, this comfortable ranch offers easy living with three bedrooms and two full baths. A standout feature is the spacious one-bedroom apartment with its own private entry, a cozy kitchenette, and a fully accessible handicapped bathroom--perfect for guests, extended family, or rental income.The home features a fireplaced living

  Keith Bradley Gibson Sotheby's International Realty

  235 Training Field Rd, Chatham, MA 02633
• 

  

  /43

  $1,400,000 Sold Feb 20, 2025

  • 2,124 Sq Ft
  • $659/SF
  • 136 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  17 Menekish Ln, Chatham, MA 02633

  Located on a tranquil private lane in highly desirable North Chatham, 17 Menekish Lane is on the market for the first time. A scenic stroll or bike ride of less than a mile takes you to the heart of charming downtown Chatham, where boutique shops, delightful restaurants, and the iconic Chatham Bars Inn await. A quick stroll down the street brings you to Cow Yard Beach for kayaking or standup

  Daren Marvin Sotheby's International Realty

  17 Menekish Ln, Chatham, MA 02633
• 

  

  /40

  Est $5,557,359 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 4,576 Sq Ft

  177 Cross St, Chatham, MA 02633

  177 Cross St, Chatham, MA 02633
• 

  

  /53

  $1,400,000

  • 3 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
• 

  

  /50

  $2,450,000 Sold Feb 18, 2025

  • 3,193 Sq Ft
  • $767/SF
  • 27 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2016

  55 Youngs Rd, Chatham, MA 2633

  This beautifully crafted Chatham residence is 3/4 of a mile from the Barn Hill Rd boat landing (Home of Chatham Kayak Co and Chatham Shellfish Co) and just under a mile from Harding's Beach. Upon entering the main level, you are greeted by stunning oak floors that exude warmth and elegance throughout. The chef's kitchen features exquisite quartz countertops and top-of-the-line Viking appliances.

  Marcia Thorngate Smith Christie's International Real Estate Atlantic Brokerage

  55 Youngs Rd, Chatham, MA 2633
• 

  

  /44

  Est $6,236,320 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,567 Sq Ft

  52 Tisquantum Rd, Chatham, MA 02633

  52 Tisquantum Rd, 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
• 

  

  /28

  $475,000 Sold Feb 14, 2025

  • 616 Sq Ft
  • $771/SF
  • 22 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1846

  435 Main St, Chatham, MA 2633

  Positioned just off Chatham's iconic Main Street, this freestanding 2-bedroom, 1-bath condo offers charm, convenience, and opportunity. With a thoughtful layout, the main level features an open-concept living space, while two bedrooms upstairs provide privacy and comfort.This property boasts a strong rental history but could also be the perfect summer escape or a valuable addition to a savvy

  Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  435 Main St, Chatham, MA 2633
• 

  

  /69

  Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 5,619 Sq Ft

  513 Stage Harbor Rd, Chatham, MA 02633

  513 Stage Harbor Rd, Chatham, MA 02633
• 

  

  /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
• 

  

  /10

  $192,000 Sold Feb 13, 2025

  • 450 Sq Ft
  • $427/SF
  • 37 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1991

  33 Cross St Unit 4, Chatham, MA 02633

  Here is your opportunity to have a unique and convenient spot right in downtown Chatham. This Chatham House Co-Op unit features a spacious bedroom and bathroom, a cozy kitchen, and a comfortable living space. Among other items, the monthly fee includes all utilities, and covers structural and mechanical maintenance. Extra storage and laundry can be found in the shared basement. A small deck off

  Brennan Finnegan William Raveis Real Estate & Home Services

  33 Cross St Unit 4, Chatham, MA 02633
• 

  

  /25

  Est $4,661,182 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,514 Sq Ft

  192 Eastward Rd, Chatham, MA 02633

  192 Eastward Rd, Chatham, MA 02633
• 

  

  /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
• 

  

  /22

  $415,000 Sold Feb 11, 2025

  • 1,080 Sq Ft
  • $384/SF
  • 71 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  912 Main St Unit 207, Chatham, MA 02633

  Welcome home to easy living at Park Place, a 62+ senior independent living community centrally located in the quaint seaside village of Chatham! Privacy abounds in this second floor, corner unit with a multitude of recent upgrades and highly desirable features like high-end laminate flooring, new primary shower, granite countertops, a new range & French door refrigerator, large walk-in closet in

  Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

  912 Main St Unit 207, Chatham, MA 02633
• 

  

  /39

  Est $1,924,590 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,445 Sq Ft

  560 Orleans Rd, North Chatham, MA 02650

  560 Orleans Rd, North Chatham, MA 02650
• 

  

  /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
• 

  

  /52

  $970,000 Sold Feb 07, 2025

  • 1,331 Sq Ft
  • $729/SF
  • 51 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1947

  58 Diane Dr, Chatham, MA 02633

  This charming ranch style home is located in the highly sought after Ridgevale Beach Hills Community. The property offers 2 bedrooms (one on either side of the home), a spacious bathroom, wood burning fireplace, interior access to the garage, second floor home office and playroom, a spacious living room with lots of natural light, panoramic views of the marsh, hardwood floors, and exterior access

  A Cape Life Today Real Estate

  58 Diane Dr, Chatham, MA 02633
• 

  

  /43

  Est $2,561,031 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,406 Sq Ft

  30 Pine Ln, North Chatham, MA 02650

  30 Pine Ln, 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

  Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

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

  

  /47

  $2,850,000 Sold Feb 03, 2025

  • 2,399 Sq Ft
  • $1188/SF
  • 91 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1956

  47 Quasson Rd, Chatham, MA 02633

  Rare opportunity in Mattaquason Point Association! This 4-bedroom 4-bath home is being offered for the first time in a generation. Sited on almost half an acre, and steps away from both downtown Chatham and Lighthouse Beach, this private neighborhood also boasts deeded access to ''the sandbox'' on Chatham Harbor where you can enjoy the morning sunrise on association-owned Adirondack chairs... or

  Kristin Muller John C Ricotta & Assoc.

  47 Quasson Rd, Chatham, MA 02633
• 

  

  /47

  Est $2,764,379 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,996 Sq Ft

  74 Frost Fish Rd, North Chatham, MA 02650

  74 Frost Fish Rd, 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 second-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
• 

  

  /30

  $2,195,800 Sold Jan 31, 2025

  • 3,776 Sq Ft
  • $582/SF
  • 1 Day On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2001

  72 Old Field Bend, North Chatham, MA 02650

  This is a rare chance to own a coastal retreat in North Chatham's coveted Cannon Hill Association. Built in 2001, this 4 BR, 4.5 BA colonial thoughtfully marries modern comforts with Cape Cod authenticity, offering a wonderful floor-plan perfect for entertaining and hosting guests. Warm hardwood floors guide you into a welcoming living room anchored by a gas fireplace, while the chef's

  Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

  72 Old Field Bend, North Chatham, MA 02650
• 

  

  /25

  Est $458,140 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,038 Sq Ft

  409 Orleans Rd Unit A, North Chatham, MA 02650

  409 Orleans Rd Unit A, 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
• 

  

  /31

  $800,000 Sold Jan 31, 2025

  • 1,976 Sq Ft
  • $405/SF
  • 121 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  53 Partridge Path, South Chatham, MA 02659

  This immaculate, spacious three bedroom, 2.5 bath colonial is privately set on a cul-de-sac! This beautiful home features a front to back living room with gas fired wood stove set in the fire place and double sliders to a sunny deck. A bright white on white eat in kitchen with light granite counters with sliders opening to a rear private deck is ideal for summer entertaining plus there is a

  Kayla Hilts Today Real Estate

  53 Partridge Path, South Chatham, MA 02659
• 

  

  /18

  Est $498,065 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,013 Sq Ft

  407 Orleans Rd Unit B, North Chatham, MA 02650

  407 Orleans Rd Unit B, North Chatham, MA 02650
• 

  

  /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
• 

  

  /28

  $800,000 Sold Jan 31, 2025

  • 1,976 Sq Ft
  • $405/SF
  • 124 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  53 Partridge Path, Chatham, MA 02633

  This immaculate and spacious colonial is privately set on a cul-de-sac! This beautiful home features a front to back living room with gas fired wood stove set in the fire place and double sliders to a sunny deck. A bright white on white eat in kitchen with light granite counters with sliders opening to a rear private deck is ideal for summer entertaining plus there is a formal dining room for

  Kayla Hilts Today Real Estate, Inc.

  53 Partridge Path, Chatham, MA 02633
• 

  

  /26

  Est $404,269 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 836 Sq Ft

  36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

  36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

Showing Results 161 - 200, Page 5 of 18