Chatham, MA Homes

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  $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
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  /29

  $14,000 per month

  • 6 Beds
  • 4.5 Baths
  • 3,941 Sq Ft
  • House for Rent

  351 Whidah Rd, North Chatham, MA 02650

  **Summer Weekly or Monthly rental, please inquire about availability** Incredible views and exclusive location! Located in North Chatham, with expansive, commanding and sweeping saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to Pleasant Bay and Orleans from this classic Cape Cod home located at end of a quiet road located in Cannon Hill. High on a

  Anthony Escobedo Coldwell Banker Realty - Newton

  351 Whidah Rd, North Chatham, MA 02650
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  $5,300,000 Sold Jan 14, 2026

  4 Ministers Ln, North Chatham, MA 02650

  • 5 Beds
  • 6.5 Baths
  • 5,143 Sq Ft
  • Built 2003

  Last Sold Summary

  • 12% Below List Price
  • $1,031/SF
  • 256 Days On Market

  Current Estimated Value $6,022,388

  Last Listing Agent Chris Rhinesmith Compass

  4 Ministers Ln, North Chatham, MA 02650
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  /30

  Not Listed For Sale

  25 Bobbie's Ln, Chatham, MA 02659

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft
  • Built 1950

  25 Bobbie's Ln, Chatham, MA 02659

  Last Sold Summary

  • $917/SF
  • 3 Days On Market

  Last Sold Price $708,115

  Last Listing Agent Shane Masaschi Compass
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  $5,995,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft

  101 Morris Island Rd, Chatham, MA 02633

  LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated

  The Bohman Hartung Group Gibson Sotheby's International Realty

  101 Morris Island Rd, Chatham, MA 02633
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  /12

  $9,500 per month

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  15 Myrtle Dr, South Chatham, MA 02659

  SEASONAL RENTAL JUNE -AUGUSTClassic cedar shingled Cape Cod–style 4-bedroom, 2-bath home on a quiet street in South Chatham. This lovely home sets the scene for slow mornings with coffee and a good book. Inside, sunny rooms and gleaming hardwood floors flow from a cozy living room to a well-equipped kitchen—perfect for baking warm bread or prepping fresh-caught seafood. Four comfortable bedrooms

  Eleanor Bright Berkshire Hathaway HomeServices Commonwealth Real Estate

  15 Myrtle Dr, South Chatham, MA 02659
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  $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 $4,655,464

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

  79 Barcliff Ave, Chatham, MA 02633
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  /4

  Est $3,288,819 Not Listed For Sale

  21 Hunter Rise, Chatham, MA 02633

  • 3 Beds
  • 5.5 Baths
  • 4,197 Sq Ft
  • Built 2018

  21 Hunter Rise, Chatham, MA 02633

  Last Sold Summary

  • 17% Above List Price
  • $667/SF
  • 56 Days On Market

  Last Sold Price $2,800,000

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC
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  $5,400,000 Open Sat 2PM - 3:30PM

  • 5 Beds
  • 4.5 Baths
  • 5,587 Sq Ft

  169 Tisquantum Rd, Chatham, MA 02633

  Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the Cape Cod lifestyle. Situated in the sought-after Quitnesset community, this property is perfect for making lasting memories. Step into a the foyer with a stunning double curved staircase, leading to a vaulted living room with a cozy fireplace and a chef's kitchen designed for entertaining. Enjoy casual meals in the

  Sandra Tanco Kinlin Grover Compass

  169 Tisquantum Rd, Chatham, MA 02633
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  $20,000 per month

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

  101 Monomoyic Way, Chatham, MA 02633

  Furnished rental available June 1st to October 1st, 2026. 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

  Steven Cohen Team Keller Williams Realty Boston-Metro | Back Bay

  101 Monomoyic Way, Chatham, MA 02633
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  /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
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  Est $3,545,851 Not Listed For Sale

  110 Sea Shells Dr, South Chatham, MA 02659

  • 3 Beds
  • 2.5 Baths
  • 2,751 Sq Ft
  • Built 1982

  110 Sea Shells Dr, South Chatham, MA 02659

  Last Sold Summary

  • 28% Below List Price
  • $1,781/SF
  • 10 Days On Market

  Last Sold Price $4,900,000

  Last Listing Agent The Bohman Hartung Group Gibson Sotheby's International Realty
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  $2,500,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  16 Old Salt Works Rd, Chatham, MA 02633

  This charming Cape-style home is located in Eastward Point, one of Chatham's most coveted coastal enclaves, near the eastern end of Fox Hill Road. Membership in the homeowners association grants access to private sandy beaches as well as use of a shared deep water dock on Crows Pond - leading to Pleasant Bay and the Atlantic.The thoughtful renovation, performed by Polhemus and Savory, seamlessly

  Chet Crabtree Christie's International Real Estate Atlantic Brokerage

  16 Old Salt Works Rd, Chatham, MA 02633
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  /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 $633,136

  Last Listing Agent David Colville HomeSmart First Class Realty

  369 Orleans Rd Unit A, Chatham, MA 2633
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  Est $3,042,274 Not Listed For Sale

  47 Quasson Rd, Chatham, MA 02633

  • 4 Beds
  • 4 Baths
  • 2,399 Sq Ft
  • Built 1956

  47 Quasson Rd, Chatham, MA 02633

  Last Sold Summary

  • 7% Above List Price
  • $1,188/SF
  • 91 Days On Market

  Last Sold Price $2,850,000

  Last Listing Agent Kristin Muller John C Ricotta & Assoc.
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  /10

  $4,525,000 New Construction

  • 4 Beds
  • 6 Baths
  • 5,300 Sq Ft

  230 Barcliff Ave, Chatham, MA 02633

  Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway and anticipating delivery for late June 2026...Architecturally pleasing 4BR 6 bath shingled home with pool will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The

  Lori Fanning Smith Compass Massachusetts, LLC

  230 Barcliff Ave, Chatham, MA 02633
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  /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 $2,073,598

  Last Listing Agent Barbara Garside eXp Realty, LLC

  450 Old Harbor Rd, Chatham, MA 02633
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  Est $3,134,627 Not Listed For Sale

  114 Main St, Chatham, MA 02633

  • 6 Beds
  • 4 Baths
  • 4,449 Sq Ft
  • Built 1809

  114 Main St, Chatham, MA 02633

  Last Sold Summary

  • 21% Above List Price
  • $582/SF
  • 589 Days On Market

  Last Sold Price $2,590,000

  Last Listing Agent John Burke William Raveis Real Estate & Home Services
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  $2,950,000

  • 3 Beds
  • 2.5 Baths
  • 3,504 Sq Ft

  41 Court St, North Chatham, MA 02650

  Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style & includes extra 20,737 Sq ft building lot. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas

  Phyllis Power Compass

  41 Court St, North Chatham, MA 02650
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  /41

  $765,000 Sold Mar 12, 2026

  23 Shane Dr, Chatham, MA 02633

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1965

  Last Sold Summary

  • 2% Above List Price
  • $724/SF
  • 41 Days On Market

  Current Estimated Value $762,406

  Last Listing Agent Samantha Edwards Compass

  23 Shane Dr, Chatham, MA 02633
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  /42

  Est $7,156,374 Not Listed For Sale

  504 Old Harbor Rd, North Chatham, MA 02650

  • 8 Beds
  • 5.5 Baths
  • 4,859 Sq Ft
  • Built 1940

  504 Old Harbor Rd, North Chatham, MA 02650

  Last Sold Summary

  • 16% Below List Price
  • $1,749/SF
  • 156 Days On Market

  Last Sold Price $8,500,000

  Last Listing Agent Phyllis Power Compass
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  $2,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,481 Sq Ft

  234 Round Cove Rd, Chatham, MA 02633

  Tucked within Chatham's coveted Riverbay community, 234 Round Cove Road offers a rare blend of walkability and private, resort-style living. Moments to Jackknife Beach and Pleasant Bay, the setting delivers coastal access while feeling entirely private and your own.Designed for effortless living, the single-level layout features three oversized bedrooms and 2.5 baths, including a secluded primary

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  234 Round Cove Rd, Chatham, MA 02633
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  $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 $1,569,644

  Last Listing Agent Shane Masaschi Compass

  457 Training Field Rd, Chatham, MA 02633
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  Est $2,629,211 Not Listed For Sale

  47 Gladen Ln, Chatham, MA 02633

  • 4 Beds
  • 3 Baths
  • 3,203 Sq Ft
  • Built 1987

  47 Gladen Ln, Chatham, MA 02633

  Last Sold Summary

  • 12% Above List Price
  • $734/SF
  • 13 Days On Market

  Last Sold Price $2,350,000

  Last Listing Agent John Hopkins Frank A Sullivan Real Estate
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  $3,200,000

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft

  92 Indian Trail, Chatham, MA 02633

  Professional photos coming soon! Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living. This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted

  Judith Smith John C Ricotta & Assoc.

  92 Indian Trail, Chatham, MA 02633
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  /30

  $1,415,000 Sold Jan 12, 2026

  200 Hardings Beach Rd, Chatham, MA 02633

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 1964

  Last Sold Summary

  • 5% Below List Price
  • $777/SF
  • 75 Days On Market

  Current Estimated Value $1,422,337

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  200 Hardings Beach Rd, Chatham, MA 02633
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  Est $3,974,081 Not Listed For Sale

  38 Sandy Shoes Ln, Chatham, MA 02633

  • 7 Beds
  • 5 Baths
  • 3,203 Sq Ft
  • Built 1930

  38 Sandy Shoes Ln, Chatham, MA 02633

  Last Sold Summary

  • 5% Above List Price
  • $1,186/SF
  • 6 Days On Market

  Last Sold Price $3,800,000

  Last Listing Agent Team Real Market Berkshire Hathaway HomeServices Commonwealth Real Estate
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  $2,297,000 Pending

  • 3 Beds
  • 4 Baths
  • 3,090 Sq Ft

  2 Seapine Rd, North Chatham, MA 02650

  Offered fully furnished, this light filled Cape in North Chatham offers easy Cape living in a great location. The main level includes a comfortable den, a living room with fireplace, and a kitchen and dining area that opens to a sunny deck, perfect for indoor-outdoor living. There's also a first-floor primary bedroom for added convenience.Upstairs you'll find two additional bedrooms, a full bath,

  The Bohman Hartung Group Gibson Sotheby's International Realty

  2 Seapine Rd, North Chatham, MA 02650
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  /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 $946,208

  Last Listing Agent Andy Falconio Kinlin Grover Compass

  100 Potonumecot Rd, Chatham, MA 02633
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  Est $1,977,760 Not Listed For Sale

  393 Main St, Chatham, MA 02633

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Built 1910

  393 Main St, Chatham, MA 02633

  Last Sold Summary

  • 1% Below List Price
  • $1,209/SF
  • 98 Days On Market

  Last Sold Price $1,995,000

  Last Listing Agent Chris Rhinesmith Compass
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  /46

  $2,199,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,651 Sq Ft

  8 Kingsbury Way, Chatham, MA 02633

  Tucked away at the end of a private lane in the heart of town, this charming 3-bedroom, 2.5-bath Cape offers the perfect blend of classic character and modern comfort--just steps from Children's Beach on Oyster Pond. Wide pine floors and warm architectural details create an inviting atmosphere throughout the main level. The first-floor primary suite features a full bath and serene water views,

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  8 Kingsbury Way, Chatham, MA 02633
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  /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 $1,400,425

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

  67 The Cornfield, Chatham, MA 02633
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  Est $2,556,253 Not Listed For Sale

  10 Mill Hill Ln, Chatham, MA 02633

  • 3 Beds
  • 2.5 Baths
  • 2,174 Sq Ft
  • Built 1720

  10 Mill Hill Ln, Chatham, MA 02633

  Last Sold Summary

  • 11% Above List Price
  • $1,061/SF
  • 44 Days On Market

  Last Sold Price $2,307,500

  Last Listing Agent Jessica King Compass Massachusetts, LLC
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  /90

  $4,700,000

  • 5 Beds
  • 3.5 Baths
  • 3,080 Sq Ft

  85 Cedar St, Chatham, MA 02633

  ** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms--four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room

  Tim Bailey John C Ricotta & Assoc.

  85 Cedar St, Chatham, MA 02633
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  $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
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  Not Listed For Sale

  67 School St, Chatham, MA 02633

  • 4 Beds
  • 2 Baths
  • 1,595 Sq Ft
  • Built 1910

  67 School St, Chatham, MA 02633

  Last Sold Summary

  • $1,113/SF
  • 26 Days On Market

  Last Sold Price $1,775,000

  Last Listing Agent Phyllis Power Compass
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  $2,650,000

  • 3 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  104 Seapine Rd, North Chatham, MA 02650

  Optimally sited on the lot to maximize views of Crows Pond from every room, this 3-bedroom 2.5-bath home is just steps away from the private Harbor Coves Association beach & ready to make your Chatham dreams come true. The first floor of this custom-built home features multiple living areas perfect for entertaining company or enjoying the peace of all four seasons in Chatham. With hardwood floors

  Kristin Muller John C Ricotta & Assoc.

  104 Seapine Rd, North Chatham, MA 02650
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  $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

  Current Estimated Value $3,336,201

  Last Listing Agent Jill Boudreau eXp Realty, LLC

  174 Seapine Rd, North Chatham, MA 02650
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  Est $3,268,214 Not Listed For Sale

  35 Mill Hill Ln, Chatham, MA 02633

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1987

  35 Mill Hill Ln, Chatham, MA 02633

  Last Sold Summary

  • 2% Above List Price
  • $1,585/SF
  • 3 Days On Market

  Last Sold Price $3,195,000

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC
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  $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

  287 Cedar St, Chatham, MA 02633

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