17

Chatham, MA Homes for Sale with Acreage

Section Image Section Image
  • /42

    $7,900,000

    • 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,

    Agent Photo

    Shane Masaschi

    Compass

    (508) 501-9618

    44 Buena Vista Rd, 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

    Agent Photo

    Kimberly Clark

    Bayside Realty Consultants

    (508) 719-6244

    1761 Main St, Chatham, MA 02633
  • /74

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 4,072 Sq Ft

    55 Winterset Dr, Chatham, MA 02633

    Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

    Agent Photo

    Tara Schiffmann Brown

    Bayview Real Estate

    (508) 388-5284

    55 Winterset Dr, Chatham, MA 02633
  • /50

    $5,495,000

    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    The first of two homes in a private, gated South Chatham enclave retreated off Main Street and bound in the rear by over 550' of Chatham Bike Trail. The first home is an uncommonly stylish 5700 +/- SF destination home designed for generational use and comfort situated on a magnificent piece of land with numerous recreational possibilities (see proposed tennis/ pickleball location), direct private

    Agent Photo

    Chris Olson

    eXp Realty, LLC

    (508) 715-6571

    48 Sylvan Way, South Chatham, MA 02659
  • /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

    Agent Photo

    Shane Masaschi

    Compass

    (508) 400-2035

    99 Uncle Alberts Drive Extension, Chatham, MA 2633
  • /39

    $11,250,000

    • 5 Beds
    • 10 Baths
    • 11,000 Sq Ft

    558 Fox Hill Rd, Chatham, MA 02633

    Welcome to Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a thoughtful

    Brian Dougherty Corcoran Property Advisors

    558 Fox Hill Rd, Chatham, MA 02633
  • /35

    $8,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,307 Sq Ft

    127 Wapoos Trail, Chatham, MA 02633

    Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water view residence is a rare treasure offering architectural distinction and an intimate connection to Cape Cod's unspoiled coastal beauty. With panoramic views spanning Stage Harbor to the Atlantic shoreline, the home was thoughtfully designed to embrace its extraordinary setting—inviting nature's ever-changing

    Dee Sullivan Christie's International Real Estate Atlantic Brokerage

    127 Wapoos Trail, Chatham, MA 02633
  • /52

    $7,999,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    30 Tisquantum Rd, Chatham, MA 02633

    What. A. View! 180 degree panoramic water vistas over The Atlantic Ocean, Chatham Harbor, and picturesque Stage Harbor set the tone for this shingled style home located high on a hill on private Morris Island. Sweeping ocean views and a private association beach combine with 2.33 acres to create a luxurious yet comfortable coastal retreat located in the Quitnesset Association.

    Lori Fanning Smith Compass Massachusetts, LLC

    30 Tisquantum Rd, 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
  • /2

    $6,995,000

    • 5 Beds
    • 7 Baths
    • 5,700 Sq Ft

    13 Captain Knowles Way, Chatham, MA 02633

    Experience luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship. Designed for both comfort and entertaining, it offers five spacious bedrooms, each

    Mina O'Keefe Gibson Sotheby's International Realty

    13 Captain Knowles Way, Chatham, MA 02633
  • /90

    $4,975,000

    • 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
  • /28

    $489,000

    • 2 Beds
    • 1.5 Baths
    • 576 Sq Ft

    19 Captain Richards Way Unit 1, Chatham, MA 02633

    Coastal Charm in Chatham. Located in one of Cape Cod's most sough-after towns, this updated seasonal free standing cottage offers the perfect blend of charm, conveniience and summer living. Just mins to Harding's Beach, shops, and restaurants, it features a bright open layout with vaulted ceilings skylight and whitewashed wood throughout. The kitchen includes vintage inspired appliances butcher

    Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    19 Captain Richards Way Unit 1, Chatham, MA 02633
  • /35

    $4,395,000

    • 3 Beds
    • 3 Baths
    • 2,418 Sq Ft

    30 Indian Trail, Chatham, MA 02633

    Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal masterpiece nestled in Hardings Beach Hills with panoramic views of the marsh and creek. Blending classic Cape vernacular with modern inspiration, the home is defined by extraordinary craftsmanship and architectural detail. The open main level features a curved fireplace wall with v-groove paneling that flows into

    Chris Rhinesmith Compass Massachusetts, LLC

    30 Indian Trail, Chatham, MA 02633
  • /42

    $1,225,000

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft

    597 Orleans Rd, North Chatham, MA 02650

    Set on over an acre and a half of beautifully landscaped grounds, this 3-bedroom contemporary home is flooded w/natural light and offers stunning water views, a flexible floor plan and impressive finishes.The welcoming living room offers walls of windows, cathedral ceilings, a focal fireplace and skylights. A white chef’s kitchen has granite counters, stainless appliances and is open to the

    Cape Cod Power of Two Compass

    597 Orleans Rd, North Chatham, MA 02650
  • /49

    $4,750,000

    • 4 Beds
    • 3.5 Baths
    • 3,878 Sq Ft

    38 Indian Trail, Chatham, MA 02633

    BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a

    Chris Rhinesmith Compass Massachusetts, LLC

    38 Indian Trail, 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
  • /42

    $3,495,000

    • 4 Beds
    • 3.5 Baths
    • 4,857 Sq Ft

    36 Moonbeam Ln, Chatham, MA 02633

    This expansive Cape with timeless curb appeal is located in an exclusive area just 5 minutes to Town and includes deeded rights to the Oyster Pond River. You’ll enjoy 4,857 square feet of casual elegance in a thoughtfully-designed floor plan. This immaculate home offers 4 spacious BRs including a first-floor primary suite. Sunny granite & stainless kitchen opens to the family room w/fireplace.

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    36 Moonbeam Ln, Chatham, MA 02633

Home Trends in Chatham, MA

Housing Trends

Median Sale Price
$1,511,258
Median Single Family Sale Price
$1,995,000
Median Townhouse Sale Price
$4,125,000
Median 2 Bedroom Sale Price
$485,000
Median 1 Bedroom Sale Price
$447,000
Average Price Per Sq Ft
$931
Number of Homes for Sale
48
Last 12 months Home Sales
222
Months of Supply
2.60
Median List Price
$1,900,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
15%
How to Buy a Home How to Finance a Home How to Sell a Home