Chatham, MA Homes

• 

  

  

  /68

  $4,295,000

  • 3 Beds
  • 4.5 Baths
  • 5,154 Sq Ft

  83 Old Mail Rd, North Chatham, MA 02650

  NEW CONSTRUCTION: 83 Old Mail Rd is a stunning 3 BR, 4.5 bath, 5,154 sf retreat in North Chatham. This elegant home showcases exceptional craftsmanship & high-end finishes for refined coastal living. The chef's Thermador kitchen with quartz counters and waterfall island opens to a butler's pantry with custom sink & beverage fridge and a first-floor dining room with coffered ceiling. A

  

  Shane Masaschi

  Compass

  (508) 318-7929

  83 Old Mail Rd, North Chatham, MA 02650
• 

  

  

  /17

  $2,000 total monthly price

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

  175 Sam Ryder Rd, Chatham, MA 02633

  Off Season Rental! Available now to the 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.

  Alison Shanley Keller Williams Realty Signature Properties

  175 Sam Ryder Rd, Chatham, MA 02633
• 

  

  

  /77

  $4,500,000 Sold Apr 23, 2025

  79 Barcliff Ave, Chatham, MA 02633

  • 3 Beds
  • 5 Baths
  • 3,724 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $1,208/SF
  • 3 Days On Market

  Current Estimated Value $4,516,006

  Last Listing Agent Doug Grattan Christie's International Real Estate Atlantic Brokerage

  79 Barcliff Ave, Chatham, MA 02633
• 

  

  

  /30

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft

  25 Bobbie's Ln, Chatham, MA 02659

  25 Bobbie's Ln, Chatham, MA 02659
• 

  

  

  /73

  $7,250,000

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

  44 Buena Vista Rd, Chatham, MA 02633

  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,

  

  Shane Masaschi

  Compass

  (508) 501-9618

  44 Buena Vista Rd, Chatham, MA 02633
• 

  

  /18

  $4,950 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  101 Monomoyic Way, Chatham, MA 02633

  Available furnished rental November 1 - April 30. Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that accentuate the

  Kate Wood Keller Williams Realty Boston-Metro | Back Bay

  101 Monomoyic Way, Chatham, MA 02633
• 

  

  /59

  $1,282,500 Sold Oct 08, 2025

  591 Crowell Rd, North Chatham, MA 02650

  • 4 Beds
  • 3 Baths
  • 1,661 Sq Ft
  • Built 1850

  Last Sold Summary

  • 3% Below List Price
  • $772/SF
  • 15 Days On Market

  Last Listing Agent Cheryle Young Today Real Estate

  591 Crowell Rd, North Chatham, MA 02650
• 

  

  /4

  Est $3,019,423 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
• 

  

  /32

  $799,900 Pending

  • 2 Beds
  • 2 Baths
  • 868 Sq Ft

  47 Cranberry Way, South Chatham, MA 2659

  Tucked away on a picturesque side street off Cockle Cove Road in Chatham, this delightful 2-bedroom, 2-bath home is full of coastal charm.Step through the front door into a warm, inviting living room complete with wood floors and a cozy fireplace -- perfect for relaxing evenings. Just off the living area, there's space for a dining nook, while the kitchen sits at the back of the home, offering

  

  William Raye

  Gibson Sotheby's International Realty

  (508) 432-7856

  47 Cranberry Way, South Chatham, MA 2659
• 

  

  /36

  $615,300 Sold May 27, 2025

  369 Orleans Rd Unit A, Chatham, MA 2633

  • 2 Beds
  • 2.5 Baths
  • 1,283 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $480/SF
  • 18 Days On Market

  Current Estimated Value $622,733

  Last Listing Agent David Colville HomeSmart First Class Realty

  369 Orleans Rd Unit A, Chatham, MA 2633
• 

  

  /54

  Est $3,864,631 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
• 

  

  /55

  $3,200,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,544 Sq Ft

  93 Bucks Creek Rd, Chatham, MA 02633

  Welcome to 93 Bucks Creek Rd, where luxury meets coastal elegance. This architecturally stunning, custom-built home offers an unparalleled resort-style experience boasting a heated, saltwater pool and membership to the exclusive Hardings Hills Assn., featuring a private dock, kayak storage, & picnic area. Nestled just 3/10ths of a mile from the pristine sands of Hardings Beach, this property is

  

  Shane Masaschi

  Compass

  (508) 571-0968

  93 Bucks Creek Rd, Chatham, MA 02633
• 

  

  /31

  $1,450,000 Sold Jul 03, 2025

  450 Old Harbor Rd, Chatham, MA 02633

  • 2 Beds
  • 2.5 Baths
  • 1,510 Sq Ft
  • Built 1830

  Last Sold Summary

  • 24% Below List Price
  • $960/SF
  • 265 Days On Market

  Current Estimated Value $1,727,468

  Last Listing Agent Barbara Garside eXp Realty, LLC

  450 Old Harbor Rd, Chatham, MA 02633
• 

  

  /51

  Est $2,897,101 Not Listed For Sale

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

  114 Main St, Chatham, MA 02633

  114 Main St, Chatham, MA 02633
• 

  

  /41

  $1,295,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  79 Forest Beach Rd, South Chatham, MA 02659

  Endless Summer Awaits at 79 Forest Beach Road, South Chatham! A 3 bed, 2 bath bungalow beauty is the coastal escape you've been waiting for. Tucked just south of Route 28 and only .04 miles to sandy Forest Beach, set on an oversized 42,688 sq ft lot. Inside, you'll love the bright and breezy layout, updated kitchen, and baths, & comfort all year long with a high-efficiency 95% combo 2-zone Rinnai

  

  Shane Masaschi

  Compass

  (508) 978-3555

  79 Forest Beach Rd, South Chatham, MA 02659
• 

  

  /40

  $985,000 Sold Dec 20, 2024

  34 Horizon Dr, Chatham, MA 02633

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Below List Price
  • $410/SF
  • 107 Days On Market

  Current Estimated Value $1,087,320

  Last Listing Agent Shane Masaschi Compass

  34 Horizon Dr, Chatham, MA 02633
• 

  

  /42

  Est $8,138,871 Not Listed For Sale

  • 8 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  504 Old Harbor Rd, North Chatham, MA 02650

  504 Old Harbor Rd, North Chatham, MA 02650
• 

  

  /7

  $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
• 

  

  /44

  $1,520,000 Sold Aug 15, 2025

  457 Training Field Rd, Chatham, MA 02633

  • 3 Beds
  • 2.5 Baths
  • 3,027 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $502/SF
  • 8 Days On Market

  Current Estimated Value $1,545,573

  Last Listing Agent Shane Masaschi Compass

  457 Training Field Rd, Chatham, MA 02633
• 

  

  /37

  Est $2,700,954 Not Listed For Sale

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

  47 Gladen Ln, Chatham, MA 02633

  47 Gladen Ln, Chatham, MA 02633
• 

  

  /34

  $799,900 Pending

  • 2 Beds
  • 2 Baths
  • 868 Sq Ft

  47 Cranberry Way, Chatham, MA 02659

  Charming Coastal Retreat...Tucked away on a picturesque side street off Cockle Cove Road, this delightful 2-bedroom, 2-bath home is full of coastal charm! Step through the front door and into a warm, inviting living room complete with wood floors and a cozy fireplace — perfect for relaxing evenings. Just off the living area, there's space for a dining nook, while the well-appointed kitchen sits

  

  William Raye

  Gibson Sotheby's International Realty

  (508) 290-7066

  47 Cranberry Way, Chatham, MA 02659
• 

  

  /59

  $1,200,000 Sold Feb 24, 2025

  1174 Old Queen Anne Rd, Chatham, MA 02633

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft
  • Built 1995

  Last Sold Summary

  • 20% Below List Price
  • $742/SF
  • 256 Days On Market

  Last Listing Agent Paul McCormick Gibson Sotheby's International Realty

  1174 Old Queen Anne Rd, Chatham, MA 02633
• 

  

  /42

  Est $4,065,024 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 3,203 Sq Ft

  38 Sandy Shoes Ln, Chatham, MA 02633

  38 Sandy Shoes Ln, Chatham, MA 02633
• 

  /2

  $619,000

  • Land
  • 1.01 Acres
  • $612,871 per Acre

  1761 Main St, Chatham, MA 02633

  Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

  

  Kimberly Clark

  Bayside Realty Consultants

  (508) 719-6244

  1761 Main St, Chatham, MA 02633
• 

  

  /40

  $900,000 Sold Jul 11, 2025

  100 Potonumecot Rd, Chatham, MA 02633

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $670/SF
  • 16 Days On Market

  Current Estimated Value $931,547

  Last Listing Agent Andy Falconio Kinlin Grover Compass

  100 Potonumecot Rd, Chatham, MA 02633
• 

  

  /26

  Est $1,837,415 Not Listed For Sale

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

  393 Main St, Chatham, MA 02633

  393 Main St, Chatham, MA 02633
• 

  

  /64

  $3,850,000

  • 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) 952-9486

  287 Cedar St, Chatham, MA 02633
• 

  

  /40

  $1,320,000 Sold Jun 12, 2025

  67 The Cornfield, Chatham, MA 02633

  • 4 Beds
  • 2.5 Baths
  • 2,238 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $590/SF
  • 78 Days On Market

  Current Estimated Value $1,361,632

  Last Listing Agent Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  67 The Cornfield, Chatham, MA 02633
• 

  

  /26

  Est $2,549,523 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
• 

  

  /16

  $605,000 Pending

  • Land
  • 0.7 Acre
  • $864,286 per Acre

  Lot 6 Bobbie's Ln, Chatham, MA 02659

  Build your Cape Cod Dream! Opportunity awaits on picturesque Bobbies Lane. This generously sized 30,150 sq ft building lot, located south of Route 28, offers the perfect canvas for your Cape Cod getaway or year-round residence. Just 0.4 miles to stunning Forest Beach, you'll enjoy easy strolls to one of the most scenic and serene beaches on Nantucket Sound. Imagine building a charming 3-bedroom

  

  Shane Masaschi

  Compass

  (508) 738-3104

  Lot 6 Bobbie's Ln, Chatham, MA 02659
• 

  

  /48

  $2,000,000 Sold Sep 08, 2025

  55 Meadowview Rd S, Chatham, MA 02633

  • 4 Beds
  • 3 Baths
  • 1,897 Sq Ft
  • Built 1965

  Last Sold Summary

  • 5% Above List Price
  • $1,054/SF
  • 9 Days On Market

  Last Listing Agent INSPIRE Team Keller Williams Realty

  55 Meadowview Rd S, Chatham, MA 02633
• 

  

  /4

  Est $3,323,796 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft

  35 Mill Hill Ln, Chatham, MA 02633

  35 Mill Hill Ln, Chatham, MA 02633
• 

  

  /81

  $4,900,000

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft

  346 Morris Island Rd, Chatham, MA 02633

  Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vista out to Nantucket Sound and beyond. This four bedroom, 4.5 bath residence blends exquisite taste with timeless coastal elegance. Thoughtfully renovated, the home is designed to showcase wide, sweeping views of the harbor from nearly every room. Light-filled interiors pair refined finishes with a relaxed

  

  Barbara Garside

  eXp Realty, LLC

  (508) 401-8501

  346 Morris Island Rd, Chatham, MA 02633
• 

  

  /47

  $3,350,000 Sold Dec 11, 2025

  174 Seapine Rd, North Chatham, MA 02650

  • 4 Beds
  • 3.5 Baths
  • 3,899 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Below List Price
  • $859/SF
  • 88 Days On Market

  Last Listing Agent Jill Boudreau eXp Realty, LLC

  174 Seapine Rd, North Chatham, MA 02650
• 

  

  /23

  Est $582,862 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 551 Sq Ft

  73 Main St Unit 8, Chatham, MA 02633

  73 Main St Unit 8, Chatham, MA 02633
• 

  

  /24

  $5,900,000

  • 2 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  99 Uncle Alberts Drive Extension, Chatham, MA 2633

  Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

  

  Shane Masaschi

  Compass

  (508) 400-2035

  99 Uncle Alberts Drive Extension, Chatham, MA 2633
• 

  

  /41

  $2,500,000 Sold Oct 24, 2025

  106 Stage Neck Rd, Chatham, MA 02633

  • 4 Beds
  • 3.5 Baths
  • 3,834 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Below List Price
  • $652/SF
  • 152 Days On Market

  Last Listing Agent Jen Graham Christie's International Real Estate Atlantic Brokerage

  106 Stage Neck Rd, Chatham, MA 02633
• 

  

  /31

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,209 Sq Ft

  90 Silver Leaf Ave, Chatham, MA 02633

  90 Silver Leaf Ave, Chatham, MA 02633
• 

  

  /30

  $5,995,000 Pending

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

  4 Ministers Ln, North Chatham, MA 02650

  This unrivaled oceanfront estate on prestigious Ministers Point in North Chatham offers grand-scale living with breathtaking Atlantic Ocean vistas. The cedar shingle and stone exterior blend seamlessly with elegant interiors featuring striking architectural details, custom finishes, and exceptional craftsmanship. Sunlight fills the 11-room residence, showcasing panoramic views of Chatham's

  Chris Rhinesmith Compass

  4 Ministers Ln, North Chatham, MA 02650
• 

  

  /73

  $2,685,000 Sold Jul 09, 2025

  7 Colonial Dr, Chatham, MA 02633

  • 4 Beds
  • 2.5 Baths
  • 3,056 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Above List Price
  • $879/SF
  • 13 Days On Market

  Current Estimated Value $2,607,757

  Last Listing Agent Pam Roberts Gibson Sotheby's International Realty

  7 Colonial Dr, Chatham, MA 02633

Showing Results 1 - 40, Page 1 of 18