Chatham, MA Homes

• 

  

  

  /44

  $1,550,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,027 Sq Ft

  457 Training Field Rd, Chatham, MA 02633

  This stunning and professionally landscaped Cape-style home offers the perfect blend of comfort and amenities in a private setting. This impressive residence offers 3.024 square feet of living space on a generous 22,651 square foot lot and lovely oak hardwood floors. The front foyer leads into a spacious living room with custom built-ins & gas fireplace. A cozy den with built-ins provides a quiet

  

  Shane Masaschi

  Compass

  (508) 863-4844

  457 Training Field Rd, Chatham, MA 02633
• 

  

  

  /17

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 872 Sq Ft
  • House for Rent

  175 Sam Ryder Rd, Chatham, MA 02633

  Off Season Rental! Available 9/15 to end of May only! Welcome to this charming furnished 2 Bed 1 Bath Ranch, a true Chatham gem that has undergone a complete renovation, offering modern comforts and stylish finishes throughout. The open-concept layout features a fully equipped kitchen with stainless steel appliances and inviting island providing ample space for preparation and entertaining. The

  Alison Shanley Keller Williams Realty Signature Properties

  175 Sam Ryder Rd, Chatham, MA 02633
• 

  

  

  /40

  $900,000 Sold Jul 11, 2025

  • 1,344 Sq Ft
  • $670/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  100 Potonumecot Rd, Chatham, MA 02633

  Now is your opportunity to own in the Riverbay community. Situated on a lovely corner lot with a park-like yard, this 3-bedroom, 2 bath home is ideal for one floor living.The layout consists of a kitchen with a vaulted ceiling and skylights, an adjoining dining area and a living room with a gas fireplace. There are three spacious bedrooms and two baths. The primary bedroom is bright and airy

  Andy Falconio Kinlin Grover Compass

  100 Potonumecot Rd, Chatham, MA 02633
• 

  

  /2

  Est $2,516,675 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,037 Sq Ft

  51 Oyster Bay Ln, Chatham, MA 02633

  51 Oyster Bay Ln, Chatham, MA 02633
• 

  

  

  /55

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft

  1996 Main St, Chatham, MA 02633

  Welcome to 1996 Main Street in the picturesque town of Chatham, MA! This charming 3-bedroom, 2-bathroom ranch style home spans 1,813 square feet and is ready for your vision and creativity. With several essential updates already in place, including a new roof, fresh shingles, and a newer gas heating system, you can focus on adding your personal touch to make this house your dream retreat. The

  

  Shane Masaschi

  Compass

  (508) 506-5693

  1996 Main St, Chatham, MA 02633
• 

  

  /24

  $4,750 per month

  • 4 Beds
  • 2 Baths
  • 9,999 Sq Ft
  • House for Rent

  15 Myrtle Dr, South Chatham, MA 02659

  Don't miss this opportunity to rent this gem in one of Cape Cod's most beloved towns! Tucked away on a cozy side street, this gorgeous home is a walk away from Forest Beach and plenty of incredible restaurants. Step out on to your brand new outdoor deck and patio and enjoy a game of cornhole in your backyard after a long day at the beach. This home features two bedrooms on the first floor and two

  Sean Anderson Access

  15 Myrtle Dr, South Chatham, MA 02659
• 

  

  /28

  $795,000 Sold Jul 07, 2025

  • 1,672 Sq Ft
  • $475/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  96 Island View Ln, South Chatham, MA 02659

  Attention Builders! This 3 BR, 2 Bath Cape offers curb appeal and a desirable cul-de-sac neighborhood location just 8/10 mile to Cockle Cove Beach. Huge potential awaits to create your Chatham dream home; bring your ideas! Great floor plan to work with includes open living and dining, good-sized kitchen, BRs and a bath on each level, plus a 12 x 19 attic perfect for finishing. Full walk-out

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  96 Island View Ln, South Chatham, MA 02659
• 

  

  /69

  Est $1,236,210 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,153 Sq Ft

  37 Chatharbor Ln, South Chatham, MA 02659

  37 Chatharbor Ln, South Chatham, MA 02659
• 

  

  /69

  $4,395,000 Open Sun 11:30AM - 1PM

  • 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

  

  Shane Masaschi

  Compass

  (508) 290-5337

  287 Cedar St, Chatham, MA 02633
• 

  

  /31

  $1,450,000 Sold Jul 03, 2025

  • 1,510 Sq Ft
  • $960/SF
  • 265 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1830

  450 Old Harbor Rd, Chatham, MA 02633

  Once in a lifetime are you fortunate enough to be presented with an opportunity to own beachfront property! Waterfront Haven with Seawall Bulkhead & Stunning Views of Chatham Harbor. Experience the potential of this unique waterfront property nestled along Chatham Harbor. This two-bedroom, two and a half bath home features a private sandy beach with panoramic views out to the Atlantic Ocean. The

  Barbara Garside eXp Realty, LLC

  450 Old Harbor Rd, Chatham, MA 02633
• 

  

  /12

  Not Listed For Sale

  140 Happy Valley Rd, Chatham, MA 02633

  140 Happy Valley Rd, Chatham, MA 02633
• 

  

  /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,

  

  Barbara Garside

  eXp Realty, LLC

  (508) 458-8396

  39 Meadow Brook Rd, Chatham, MA 02650
• 

  

  /38

  $2,200,000 Sold Jul 03, 2025

  • 1,863 Sq Ft
  • $1181/SF
  • 356 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  16 Little Beach Rd, Chatham, MA 02633

  OFFERED FULLY FURNISHED AND READY FOR SUMMER OCCUPANCY. Immerse yourself in the ultimate beach lifestyle. Superbly located in a highly desirable Lighthouse Beach neighborhood, this luxurious beach house built in 2018 was extensively refreshed in 2023 with all new bathrooms, appliances, light and plumbing fixtures, smart technology and exterior curb appeal. The interiors are both elegant and

  Chris Rhinesmith Compass Massachusetts, LLC

  16 Little Beach Rd, Chatham, MA 02633
• 

  

  /4

  Est $3,265,162 Not Listed For Sale

  • 3 Beds
  • 5.5 Baths
  • 4,197 Sq Ft

  21 Hunter Rise, Chatham, MA 02633

  21 Hunter Rise, Chatham, MA 02633
• 

  

  /39

  $1,700,000

  • 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

  

  Shane Masaschi

  Compass

  (508) 682-4461

  9 Bettys Path, Chatham, MA 02633
• 

  

  /6

  $635,000 Sold Jul 01, 2025

  • 912 Sq Ft
  • $696/SF
  • 135 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1972

  127 Oak Hill Rd, Chatham, MA 02633

  Almost 1 acre in a desirable quiet neighborhood. The land provides space to remodel or update the exiting house and make it your own. House needs work and is being sold As Is. Septic Inspection completed early December- passed Title V for 3 bedroom - report attached to listing.

  Sarah Gammons - Ciampa Berkshire Hathaway HomeServices Robert Paul Properties

  127 Oak Hill Rd, Chatham, MA 02633
• 

  

  /54

  Est $3,846,255 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,751 Sq Ft

  110 Sea Shells Dr, South Chatham, MA 02659

  110 Sea Shells Dr, South Chatham, MA 02659
• 

  

  /18

  $600,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  19 Stoughton Ln, Chatham, MA 2633

  Here is your chance to own a slice of seaside Chatham! This prime location is only a short walk or .02 miles to stunning Ridgevale Beach on pristine Nantucket Sound. Included in the sale is a 3 bedroom Title V septic, ZBA approval to demolish the existing structure and to build a dwelling with a deck. Seller has building plans for a 3 bedroom, 2 bath, 1356 SF home. Imagine the possibilities of

  

  Shane Masaschi

  Compass

  (508) 400-2035

  19 Stoughton Ln, Chatham, MA 2633
• 

  

  /20

  $734,000 Sold Jun 27, 2025

  • 992 Sq Ft
  • $740/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  61 Pond View Ave, Chatham, MA 02633

  Welcome to your dream Cape Cod getaway! This delightful 2-bedroom, 1-bath home is nestled in one of West Chatham’s most desirable neighborhoods. This home is just minutes from Hardings Beach, local shopping, and great dining spots. Step inside to find a warm and inviting interior with natural tones that create a relaxed, coastal feel throughout. Whether you're enjoying a quiet weekend or

  Charles Quigley Keller Williams Realty

  61 Pond View Ave, Chatham, MA 02633
• 

  

  /51

  Est $3,015,836 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 4,449 Sq Ft

  114 Main St, Chatham, MA 02633

  114 Main St, 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,

  

  Shane Masaschi

  Compass

  (508) 691-8324

  0 George Ryder Rd Unit 73104629, Chatham, MA 02633
• 

  

  /58

  $1,309,000 Sold Jun 20, 2025

  • 2,590 Sq Ft
  • $505/SF
  • 1 Day On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  144 Countryside Dr, Chatham, MA 02633

  Welcome to this meticulously maintained Cape Cod gem in highly sought-after Chatham, lovingly cared for by a single family and used only seasonally until recently. Perched on a gentle slope for added privacy, this home offers a serene retreat surrounded by nature, and lush, manicured gardens with classic Cape plantings. Inside, a spacious family room with vaulted ceilings, a cozy fireplace, and

  Maureen Green Kinlin Grover Compass

  144 Countryside Dr, Chatham, MA 02633
• 

  

  /38

  Est $2,077,543 Not Listed For Sale

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

  671 Old Harbor Rd, North Chatham, MA 02650

  671 Old Harbor Rd, North Chatham, MA 02650
• 

  

  /54

  $3,250,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,314 Sq Ft

  35 Whistler Ln, Chatham, MA 02633

  Discover this beautiful 3-bedroom, 3.5-bath home nestled amongst lovely properties in North Chatham only 370ft from the Ocean. The thoughtfully designed reverse floor plan captures stunning views of Pleasant Bay, complemented by refreshing breezes. Enjoy the convenience of central AC, gas heat, a fireplace for cozy evenings, and a private irrigation well to maintain the level lot. Imagine the

  

  MaryEllen Monahan

  Today Real Estate

  (508) 484-8014

  35 Whistler Ln, Chatham, MA 02633
• 

  

  /12

  $3,200,000 Sold Jun 20, 2025

  • 4,620 Sq Ft
  • $693/SF
  • 346 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 2024

  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
• 

  

  /56

  Est $7,591,854 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 5,528 Sq Ft

  444 Old Harbor Rd, Chatham, MA 02633

  444 Old Harbor Rd, Chatham, MA 02633
• 

  

  /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
• 

  

  /11

  $3,200,000 Sold Jun 20, 2025

  • 4,620 Sq Ft
  • $693/SF
  • 346 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 2024

  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
• 

  

  /37

  Est $2,666,882 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,203 Sq Ft

  47 Gladen Ln, Chatham, MA 02633

  47 Gladen Ln, 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
• 

  

  /36

  $2,100,000 Sold Jun 18, 2025

  • 2,270 Sq Ft
  • $925/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  84 Emery Ln, North Chatham, MA 02650

  Location! Location! North Chatham! Sought after Emery Lane at the top of Look Out Hill, offers privacy & the convenience of town center nearby & Cow Yard landing. The best of both worlds! This custom designed Cape built by Ted Spencer offers gracious living in the spacious 2270 Sq. ft.. The sweeping staircase foyer with skylight sets the tone for elegance and charm as you enter the open plan

  Phyllis Power Compass

  84 Emery Ln, North Chatham, MA 02650
• 

  

  /12

  Est $5,610,202 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,286 Sq Ft

  486 Shore Rd, Chatham, MA 02633

  486 Shore Rd, Chatham, MA 02633
• 

  

  /76

  $4,495,000

  • 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
• 

  

  /63

  $1,125,000 Sold Jun 18, 2025

  • 1,662 Sq Ft
  • $677/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  155 Cranberry Ln, Chatham, MA 02633

  First time offered! Discover your Cape Cod retreat at 155 Cranberry Lane, South Chatham. This meticulously maintained 3-bedroom, 2-bath home offers serene living on a peaceful corner lot, bordered by conservation land. Enjoy easy access to Bucks Creek via a deeded right of way, and find yourself just moments from Ridgevale Beach. Inside, you'll appreciate hardwood floors, a renovated kitchen

  Kate Plummer Today Real Estate

  155 Cranberry Ln, Chatham, MA 02633
• 

  

  /26

  Est $1,970,324 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  393 Main St, Chatham, MA 02633

  393 Main St, Chatham, MA 02633
• 

  

  /65

  $749,900 Pending

  • 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
• 

  

  /44

  $1,350,000 Sold Jun 17, 2025

  • 2,279 Sq Ft
  • $592/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  33 Captains Walk, North Chatham, MA 02650

  This inviting 4-bedroom Colonial-style home with an attached garage is nestled in one of North Chatham's most sought-after neighborhoods. Just a short stroll to downtown Chatham and beautiful beaches, this well-loved and meticulously maintained home has been cherished by the same family for many years.Situated on a level lot with mature perennials, the property offers plenty of space to enjoy the

  Natalia Weiner Gibson Sotheby's International Realty

  33 Captains Walk, North Chatham, MA 02650
• 

  

  /26

  Est $2,695,460 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  10 Mill Hill Ln, Chatham, MA 02633

  10 Mill Hill Ln, Chatham, MA 02633
• 

  

  /25

  $3,895,000 Open Sat 1PM - 2:30PM

  • 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
• 

  

  /40

  $1,320,000 Sold Jun 12, 2025

  • 2,238 Sq Ft
  • $590/SF
  • 78 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1980

  67 The Cornfield, Chatham, MA 02633

  Situated on a quiet cul-de-sac in a desirable neighborhood, this bright Cape enjoys a prime location just a mile from town with several shops & restaurants within walking distance. Encompassing 2,300 sq. ft of living space on three levels, an easy-flowing floor plan offers a granite & stainless kitchen with adjacent open dining & breakfast nook, sun-filled living room with walls of glass, and

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  67 The Cornfield, Chatham, MA 02633

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