9,756

Chatham, MA Homes

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  • /22

    $435,000 Sold Mar 14, 2025

    • 1,013 Sq Ft
    • $429/SF
    • 6 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1987

    409 Orleans Rd Unit B, North Chatham, MA 02650

    Welcome to Quail Run, nestled off-the-beaten-path in beautiful North Chatham-yet convenient, easy access to all! This immaculate, delightful unit opens into a spacious, warm and welcoming living room with vaulted ceiling, hardwood floors, and new picture window overlooking a peaceful wooded area; the dining room has built-ins and the same wooded views; the efficient kitchen offers good storage,

    Debra Bassett Cape Cod Associates R E

    409 Orleans Rd Unit B, North Chatham, MA 02650
    • /33

      Est $670,790 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,005 Sq Ft

      367 Orleans Rd Unit C, North Chatham, MA 02650

      367 Orleans Rd Unit C, North Chatham, MA 02650
  • /41

    $1,695,000

    • 6 Beds
    • 5 Baths
    • 2,401 Sq Ft

    72 Forest Beach Rd, South Chatham, MA 2659

    South of 28 | Renovated Beach Compound with 5 Income-Producing Suites. Just 4/10 of a mile from Nantucket Sound, this iconic South Chatham property blends classic Cape charm with modern luxury. Formerly the historic Forest Beach Motel, now meticulously restored and transformed into a stylish coastal compound--offered fully furnished and move-in ready. This unique 6-bedroom, 5-bath offering fully

    Chris Rhinesmith Compass Massachusetts, LLC

    72 Forest Beach Rd, South Chatham, MA 2659
  • /36

    $2,000,000 Sold Mar 14, 2025

    • 2,884 Sq Ft
    • $693/SF
    • 133 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 2002

    53 Ocean Port Ln, Chatham, MA 02633

    South of 28 and situated on a quiet sandy lane in West Chatham, this home is the perfect beach house just a short distance to both Barn Hill Landing and Hardings Beach. Recently renovated, the home exudes coastal style living and offers superbly designed indoor and outdoor spaces. The house welcomes with an open concept great room with cathedral ceilings, abundant light and a fireplace with

    Chris Rhinesmith Compass

    53 Ocean Port Ln, Chatham, MA 02633
    • /46

      Est $1,266,710 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,780 Sq Ft

      25 Spring Hill Rd, North Chatham, MA 02650

      25 Spring Hill Rd, North Chatham, MA 02650
  • /38

    $3,950,000

    • 5 Beds
    • 3.5 Baths
    • 2,659 Sq Ft

    92 Barcliff Ave, Chatham, MA 02633

    Honored with the 2004 Chatham Preservation Award, this iconic residence blends historic charm with modern luxury. The professionally designed gardens, planted decades ago and meticulously maintained, feature vibrant blooms from spring to late October, with a rose garden peaking July 4th and lasting through fall. Inside, rich nautical detailing, wide pine floors, and a Zuber & Cie mural evoke

    Chris Rhinesmith Compass

    92 Barcliff Ave, Chatham, MA 02633
  • /31

    $1,600,000 Sold Mar 14, 2025

    • 3,401 Sq Ft
    • $470/SF
    • 13 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1988

    37 Bellamy Ln, North Chatham, MA 02650

    Located in Cannon Hill (North Chatham), this 5 bedroom, 3 bath residence has deeded rights to a private, sandy beach on Pleasant Bay. With multiple living areas, there is plenty of room for family and friends to spread out. Showings by advance appointment only.

    David Doherty Compass

    37 Bellamy Ln, North Chatham, MA 02650
    • /18

      Est $347,238 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft

      197 Stony Hill Rd Unit C, Chatham, MA 02633

      197 Stony Hill Rd Unit C, Chatham, MA 02633
  • /93

    $6,750,000

    • 5 Beds
    • 5.5 Baths
    • 5,620 Sq Ft

    15 Windy Hill Way, Chatham, MA 02633

    This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

    Tim Bailey John C Ricotta & Assoc.

    15 Windy Hill Way, Chatham, MA 02633
  • /42

    $1,600,000 Sold Mar 13, 2025

    • 1,378 Sq Ft
    • $1161/SF
    • 11 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    26 Sea Mist Ln, South Chatham, MA 02659

    Seaside Perfection with private Deeded Ocean Beach is completely turnkey! Recently redone with improvements such as: New hot water heater, New AC, and heating units, New appliances, counter tops, sink and faucet, New first floor bath update, New Primary bath with double vanity with new floor and shower. New bulkhead, New Storm door, enhanced inground sprinklers, New ceiling lights on first level

    Jan Nowak Craigville Realty Co

    26 Sea Mist Ln, South Chatham, MA 02659
    • /53

      Est $1,275,143 Not Listed For Sale

      • 2 Beds
      • 3.5 Baths
      • 2,546 Sq Ft

      43 Misty Meadow Ln Unit B, North Chatham, MA 02650

      43 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • /50

    $1,899,900

    • 3 Beds
    • 2.5 Baths
    • 3,404 Sq Ft

    331 Riverview Dr, Chatham, MA 02633

    Discover this stunning Riverbay residence remodeled to perfection. Boasting unique design elements such as shiplap and extensive moldings throughout, including soaring ceilings and a serene backyard. This turnkey three-level home with an expansive farmer's porch and an oversized two-car garage has everything you need and more. Step inside to find a chef's kitchen that will inspire your culinary

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    331 Riverview Dr, Chatham, MA 02633
  • /27

    $590,000 Sold Mar 12, 2025

    • 1,489 Sq Ft
    • $396/SF
    • 3 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    108 Misty Meadow Ln Unit A, North Chatham, MA 02650

    Discover this charming 2-bedroom, 2-bathroom condominium in the heart of North Chatham. Tucked away with tranquil wooded views, this turnkey home features beautiful wood floors and an inviting patio and deck perfect for relaxing or entertaining. Enjoy a prime location within walking distance to local gems like Chatham Works, Chatham Perk, Elwood's Raw Bar, the Shark Center, and Cow Yard Beach.

    Diane Donahue Gibson Sotheby's International Realty

    108 Misty Meadow Ln Unit A, North Chatham, MA 02650
    • /29

      Est $1,062,336 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,812 Sq Ft

      39 Misty Meadow Ln, North Chatham, MA 02650

      39 Misty Meadow Ln, North Chatham, MA 02650
  • /2

    $659,000

    • Land
    • 1.01 Acres
    • $652,475 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

    1761 Main St, Chatham, MA 02633
  • /35

    $5,000,000 Sold Mar 07, 2025

    • 3,319 Sq Ft
    • $1506/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1993

    169 Shore Rd, Chatham, MA 02633

    Situated on one of the most sought after locations in Chatham, this distinguished residence nestled on spectacular Shore Road offers a perfect blend of coastal living with accessibility to Chatham's finest beaches, the Village and a stones throw to Chatham Bars Inn with all its luxurious amenities. Set back from the road with views of Chatham Harbor on an expansive lot, this signature setting is

    Chris Rhinesmith Compass Massachusetts, LLC

    169 Shore Rd, Chatham, MA 02633
    • /27

      Est $1,070,154 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,906 Sq Ft

      37 Misty Meadow Ln Unit B, North Chatham, MA 02650

      37 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • /43

    $4,200,000

    • 6 Beds
    • 4 Baths
    • 3,808 Sq Ft

    150 Barcliff Ave, Chatham, MA 02633

    Chatham: where hydrangeas meet the sea and harbors merge into the ocean. A place where cherished memories are created and passed on through generations. If you've been dreaming of living in this storybook town, just a short stroll from sandy beaches and its vibrant Village, you've arrived. Welcome to 150 Barcliff Avenue. Tucked along one of Chatham's most picturesque streets, this updated home

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    150 Barcliff Ave, Chatham, MA 02633
  • /29

    $1,000,000 Sold Mar 07, 2025

    • 3,753 Sq Ft
    • $266/SF
    • 22 Days On Market
    • 9 Beds
    • 5 Baths
    • Built 1900

    27 Barn Hill Rd, Chatham, MA 02633

    An exceptional investment opportunity in West Chatham, 27-29 Barn Hill Road offers a five-unit multifamily property with strong cash flow and long-term potential. Ideally situated near Shop Ahoy Plaza and the West Chatham rotary, this property boasts high walkability and easy access to shops, dining, and local amenities.The front building (27 Barn Hill Road) consists of three units (27A, 27B, and

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    27 Barn Hill Rd, Chatham, MA 02633
    • /25

      Est $1,231,508 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,608 Sq Ft

      61 Bishops Terrace, Chatham, MA 02633

      61 Bishops Terrace, Chatham, MA 02633
  • /45

    $1,399,500

    • 2 Beds
    • 3 Baths
    • 1,861 Sq Ft

    116 Happy Valley Rd, Chatham, MA 02633

    Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway. 1st level open plan features brk bar & dining/living area with views to the bog pond. Door to south facing deck setup for dining & and all day sun. 2 entry kitchen with granite counters & stainless

    Ward Brown William Raveis Real Estate & Home Services

    116 Happy Valley Rd, Chatham, MA 02633
  • /41

    $799,900 Sold Mar 06, 2025

    • 1,365 Sq Ft
    • $586/SF
    • 11 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    1369 Main St, Chatham, MA 02633

    Welcome to 1369 Main Street Chatham! This newly renovated 3 bed 2 bath home sits on a beautiful, cleared, private fenced lot , offering ample space for both relaxation and recreation. A pinch under 1400sqft of living space, the property features an attached 2 car garage, providing convenient storage and parking. Whether you're searching for a cozy year round residence, a vacation retreat , or an

    Lauren Scioletti Sotheby's International Realty

    1369 Main St, Chatham, MA 02633
    • /28

      Est $1,198,508 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft

      32 Aire Ln, Chatham, MA 02633

      32 Aire Ln, Chatham, MA 02633
  • /40

    $1,475,000

    • 3 Beds
    • 3.5 Baths
    • 2,225 Sq Ft

    355 Training Field Rd, Chatham, MA 02633

    Just 8/10 of a mile to Jackknife Point BeachThis beautifully appointed Chatham retreat offers the perfect blend of comfort, style, and solar efficiency. A charming farmer’s porch welcomes you into a light-filled home with high ceilings, an open layout, and a skylit kitchen with granite counters, stainless steel appliances, and a large island. The living room features a cozy gas fireplace, and the

    Margaret McDonald Mathieu Newton Sotheby's International Realty

    355 Training Field Rd, Chatham, MA 02633
  • /62

    $2,050,000 Sold Mar 04, 2025

    • 3,899 Sq Ft
    • $526/SF
    • 220 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1961

    174 Seapine Rd, North Chatham, MA 02650

    Don't miss this fabulous home which is part of Harbor Coves Assoc. with association rights to Crows Pond a saltwater pond leading out to Bassing Harbor, Ryder's Cove, Pleasant Bay, Chatham Harbor and the Atlantic. Assoc. beach and mooring field just down the street This 4 bedroom 3 and 1/2 bath home has plenty of extra space for family and friends. Wonderful family room with cathedral ceiling,

    Judith Smith John C Ricotta & Assoc.

    174 Seapine Rd, North Chatham, MA 02650
    • /42

      Est $1,031,095 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,319 Sq Ft

      261 Stony Hill Rd, North Chatham, MA 02650

      261 Stony Hill Rd, North Chatham, MA 02650
  • /32

    $5,900,000

    • 4 Beds
    • 4.5 Baths
    • 4,654 Sq Ft

    25 Wikis Way, Chatham, MA 02633

    TIMELESS COASTAL LUXURY // Prepare to be embraced by one of the most breathtaking panoramas in all of Cape Cod. This exceptional property offers sweeping and unobstructed views that stretch from Stage Harbor and the iconic Chatham Lighthouse, to the natural beauty of Monomoy Island and the sparkling expanse of the Atlantic Ocean. From first light until sunset, this coastal retreat is surrounded

    Chris Rhinesmith Compass Massachusetts, LLC

    25 Wikis Way, Chatham, MA 02633
  • /54

    $3,695,000 Sold Mar 03, 2025

    • 4,106 Sq Ft
    • $900/SF
    • 174 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2000

    173 Kendrick Rd, North Chatham, MA 02650

    Architectural perfection meets natural harmony in this stunning Polhemus Savery DaSilva (PSD) home. Tucked quietly within a desirable North Chatham with water access on Pleasant Bay, a short stroll away, the residence offers a modern twist on the classic shingle style architecture and delivers impeccable craftsmanship, custom millwork, and exquisite stonework to create a truly refined family

    Chris Rhinesmith Compass Massachusetts, LLC

    173 Kendrick Rd, North Chatham, MA 02650
    • /13

      Est $780,995 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 955 Sq Ft

      276 Orleans Rd, Chatham, MA 02633

      276 Orleans Rd, Chatham, MA 02633
  • /28

    $1,300,000

    • 3 Beds
    • 3 Baths
    • 2,202 Sq Ft

    319 Riverview Dr, Chatham, MA 02633

    Sited on nearly an acre of land in Riverbay Estates, this spacious three bedroom, three bath home offers ample privacy and outdoor living space.Built in 1984 with an addition and updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite withgas fireplace, walk in closet, and outdoor access. The kitchen features abundant cabinet

    Chris Rhinesmith Compass

    319 Riverview Dr, Chatham, MA 02633
  • /42

    $3,800,000 Sold Feb 28, 2025

    • 4,372 Sq Ft
    • $869/SF
    • 39 Days On Market
    • 4 Beds
    • 5.5 Baths
    • Built 2014

    107 School St, Chatham, MA 02633

    Beautiful, like new condition home built in 2014 by Polhemus, Savery, and Desilva in the very sought after OLD VILLAGE. Close walk to downtown, shopping, restaurants and all that Chatham has to offer..... AND Lighthouse and Water Street beaches are only a quick 4 minute walk away,....There are 4 large bedrooms, primary en-suites on first and second floors and 5.5 total bathrooms including one off

    John Burke William Raveis Chatham

    107 School St, Chatham, MA 02633
    • /45

      Est $1,790,899 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,585 Sq Ft

      230 Barcliff Ave, Chatham, MA 02633

      230 Barcliff Ave, Chatham, MA 02633
  • /42

    $1,599,000

    • 3 Beds
    • 3.5 Baths
    • 3,050 Sq Ft

    46 Juniper Ln W, Chatham, MA 02659

    ''Moongazer'' represents a rare opportunity to purchase a thoughtfully updated, proven income-producing property with deeded access to Taylor's Pond, where it is a fun and easy kayak or paddleboard out to Nantucket Sound and the beach. This 3 BR, 3.5 Bath, 3,050 sf split-level house offers far more living space and room for overflow guests than meets the eye. Upon entering the home, you will be

    Jack Bohman Gibson Sotheby's International Realty

    46 Juniper Ln W, Chatham, MA 02659
  • /32

    $399,000 Sold Feb 28, 2025

    • 444 Sq Ft
    • $899/SF
    • 11 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1846

    427 Main St, Chatham, MA 2633

    Opportunities like this are rare—a freestanding 1-bedroom, 1-bath cottage condo just off Chatham's iconic Main Street. Tucked down a quaint alleyway, this charming retreat offers privacy with immediate access to boutique shops, award-winning dining, and Cape Cod’s finest beaches.With dedicated parking—an invaluable summer luxury—this quintessential Cape Cod escape blends classic charm with

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    427 Main St, Chatham, MA 2633
    • /95

      Est $1,941,450 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,459 Sq Ft

      244 Barcliff Ave, Chatham, MA 02633

      244 Barcliff Ave, Chatham, MA 02633
  • /39

    $1,649,000

    • 3 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    307 Riverview Dr, Chatham, MA 02633

    Discover luxury & comfort in this stunning Riverbay home nestled with beautiful landscaping on Riverview Drive. This meticulously renovated 7 room ranch offers 2340 Sq. ft of elegant living space, featuring 3 spacious bedrooms, 2.5 luxurious tiled baths with double vanities. As you step inside, the inviting foyer introduces you to the warmth of a formal living room with fireplace, open plan to

    Phyllis Power Compass

    307 Riverview Dr, Chatham, MA 02633
  • /44

    $1,800,000 Sold Feb 28, 2025

    • 1,904 Sq Ft
    • $945/SF
    • 114 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1946

    504 Stony Hill Rd, North Chatham, MA 02650

    Discover the quintessential Cape Cod lifestyle in this charming 1940's Cape ranch, perfectly situated in one of North Chatham's most sought-after neighborhoods. This well-maintained home offers a blend of classic appeal and modern convenience, nestled among substantial and elegant residences. The serene setting provides a peaceful retreat moments from Scatteree Beach. Whether you're looking to

    LUXRECapeCod Gibson Sotheby's International Realty

    504 Stony Hill Rd, North Chatham, MA 02650
    • /30

      Est $1,142,852 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,320 Sq Ft

      214 Barcliff Ave, Chatham, MA 02633

      214 Barcliff Ave, Chatham, MA 02633
  • /21

    $995,000

    • 3 Beds
    • 2 Baths
    • 1,726 Sq Ft

    144 Lakeview Ave, Chatham, MA 02633

    Three bedroom ranch house with two car garage in desirable Riverbay Estates. All bedrooms on the first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area...Brokers and buyers are

    John Burke William Raveis Chatham

    144 Lakeview Ave, Chatham, MA 02633
  • /55

    $2,610,000 Sold Feb 28, 2025

    • 2,100 Sq Ft
    • $1243/SF
    • 119 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1960

    15 Edgewater Dr, Chatham, MA 02633

    As you drive past Chatham light & turn right on Morris Island Rd, you will find yourself transported to a different time when things moved a little slower. You'll be surrounded by marshes & conservation land, popular with birders for its egrets, hawks & sandpipers. The 3BR, 3bath home sits on about a half-acre overlooking Stage Harbor to the west & the Atlantic to the east, which brings

    Shane Masaschi Compass

    15 Edgewater Dr, Chatham, MA 02633

Showing Results 121 - 160, Page 4 of 18

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