Chatham Massachusetts Real Estate & Homes For Sale

New co-ownership opportunity: own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho, and Pleasant Bay from nearly every angle. The classic shingle-style exterior includes a two-car garage and private boat dock with direct water access.

Legendary Shop Ahoy Plaza - a well-known locallandmark● Excellent visibility on busy Route 28● Positioned between the two Chatham rotaries -maximum exposure and accessibility● Great signage potential to capture drive-by attention● Large storefront display windows - ideal for retailvisibility and merchandisingFront and rear egress - easy access for customers

Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and additions in several directions in this very private location of North Chatham...Choice of 3 primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the recently retiled heated Gunite pool.

Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers ball games, concerts, Oyster Pond, and more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment.

Built by Eastward Companies in 2013, this thoughtfully designed, turnkey home is located in one of Chatham's highly desirable neighborhoods. Offering over 3,500 sq. ft. of beautifully appointed living space, this Cape features 3 bedrooms and 3.5 baths with an open-concept floor plan that seamlessly blends timeless Cape Cod style with modern conveniences.

Welcome to 88 Indian Hill Road, where stunning curb appeal and timeless Cape Cod charm welcomes you home. Perfectly situated on a prominent, beautifully landscaped large lot, this sprawling Cape has been meticulously maintained and thoughtfully designed for both everyday living and entertainment.

LONG TERM LEASE. A rare opportunity to lease a Small Business zoned property with excellent frontage on a main road in North Chatham. Perfect for professional offices with major parking access.

Location! Location! on ''The Loop'' at 330 Champlain Rd you have an exceptional lot 42, 518 Sq Ft near Stage Harbor & 2 town landings! This charming Colonial offers 2520 sqq ft of living space in a coveted private locale, great for summer or year round.

Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously updated 2,700-square-foot residence features 4 bedrooms and 3.5 bathrooms.

Beautifully appointed, fully furnished, and turnkey, this exceptional end-unit 2-bedroom, 2-bath second-floor condominium is located in the desirable Nickerson Corners community in North Chatham, offering effortless Cape Cod living in a quiet, well-maintained association.

Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement.

Exceptional opportunity to acquire two prime contiguous Main Street commercial properties being offered together as a package sale. Located in a highly visible, high-traffic location and connected to town sewer, these properties have been under the same ownership for more than 30 years and are now available due to the owner's retirement.

Nestled at the end of a cul-de-sac and abutting conservation land, this well-maintained 3-bedroom, 1.5-bath ranch offers the ideal combination of privacy, comfort, and timeless appeal. With 1,476 square feet of living space, this inviting home features hardwood floors throughout, an open floor plan, and a family room addition with a cathedral ceiling that fills the home with natural light.

Sought after neighborhood of Riverbay. Light and bright home with incredible gardens and fabulous outdoor space. Three bedrooms 2 newly redone baths with livingroom, dinng room and primary suite all with sliders onto the deck with spiral stairway to back yard for super summer fun. Room for a pool! Lower level could be finished off-high ceilings and windows overlooking the back yard.

Sprawling and spacious, 65 Captain Kendrick Drive presents an exceptional opportunity to own a beautifully situated 3 br 3 bath home in one of Chatham's most peaceful settings. Seasonal views of the Monomoy River create a serene backdrop, inviting relaxing vibes and a true sense of coastal tranquility.

Downtown Chatham location, just beofre the Main Street Rotary. Three finished levels: The first floor currently consists of a professional reception area, waiting room, and five private offices designed for efficient client-facing operations. The second floor includes six additional offices and a full bathroom, allowing for flexible administrative, executive, or possible residential adaptation.

Exceptional commercial income property on Rte 28 in North Chatham. Very well maintained 5,101 sf building with plenty of parking and visability. Many recent upgrades including roof, paved parking lot, signage, siding and landscaping. Three units all on leases. Real estate only. Please respect the tenants and patrons privacy. One tenant has right of first refusal.

Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings.

Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living.

Welcome to Riverbay Estates, where Cape Cod charm meets endless potential. Enjoy peaceful mornings and beautiful water views from nearly every room in this spacious home. This, well-built 4-bedroom, 3-bath home offers direct access to Pickerel Pond for kayaking and enjoying nature. A true ''diamond in the rough'' project with great bones ready for your updates and personal vision.

Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living.

The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6,000 square feet of living space sited on 1.

Build your 3 bedroom home in this awesome downtown location walk to everywhere you want to be in Chatham. Meander across the street to Chatham A's Lilly's, the Squire steps to Oyster Pond no car necessary. The property is surrounded by amazing gardens. A sanctuary a feast for the eyes. Call your builder bring your imagination. A oasis in downtown Chatham.

Rare to find a 20,737 lot in an established neighborhood of beautiful homes, close to town center or Ryder's Cove...overlooking Frost Fish Creek conservation, birdlife, tranquility! Building lot has been engineered by Ryder and Wilcox, pre- existing sidelines are R20. This lot will be sold separately after the home at 41 Court Street is sold, listed $2,295,000.

Tucked away in the heart of Chatham, 66 Snow Lane offers a rare blend of privacy, convenience, & natural beauty. This charming 2-bedroom, 1-bath ranch-style home is surrounded by conservation land, creating a peaceful setting where birds, wildlife, and wooded views can be enjoyed from every window.

Situated on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath, shingle-style residence is designed for seamless indoor and outdoor entertaining. The bright, airy first floor is anchored by a great room with a Rumford fireplace, custom cabinets, 10' ceilings, and towering windows. The professional-grade kitchen features premier appliances, a pantry, a wet bar, and a large center island.

Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance.

Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance and is turn key, furnished and ready for summer! Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis.

Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal showpiece set in Hardings Beach Hills, with sweeping views of the marsh and creek. Blending classic Cape vernacular with modern lines, the home showcases exceptional craftsmanship and architectural detail throughout.

Back on the market! Lovingly maintained and thoughtfully enjoyed over the years, this classic Chatham ranch reflects true pride of ownership. A traditional layout offers three bedrooms, including a primary with en suite bath, and easy, comfortable living throughout.

Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.

Conveniently positioned along Main Street in Chatham, this fully renovated housing complex offers a rare and compelling investment opportunity in one of the Cape's most supply-constrained markets. Ideally suited for workforce, employee, or long-term housing, the property is approved by the town for 33 beds and features 12 total units, each designed for comfort, privacy, and efficiency.

This exceptional coastal retreat was designed to capture sweeping views of tidal salt marshes, natural vistas, and Nantucket Sound from nearly every room. Soaring ceilings and dramatic walls of glass fill the home with natural light and frame spectacular sunsets; while sliders open to an expansive wraparound deck for effortless indoor-outdoor living.

Brand new shingled style Coastal retreat offers resort style living in sought after North Chatham location. Sited on .5 of an acre( with pool potential) near beaches and close proximity to town, Chatham Bars Inn and Chatham Seaside Links Golf , this home was curated with luxury and comfort in mind.

Tucked away in Chatham's most desirable residential enclaves, this property offers a blend of classic Cape Cod charm & refined living. Set on 40,500 sq. ft. of beautifully landscaped grounds, the home invites both quiet retreat and gracious living. Inside, rich pine floors flow throughout a lovely designed layout featuring 10 spacious rooms, including 4 bedrooms & 3.

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.

Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout.

Prime Chatham Residential Potential with R20 Zoning! This unique property offers a rare opportunity to create a standalone single-family home just moments from the vibrant heart of downtown Chatham. Prospective buyers should note that the building is currently utilized as a commercial barber shop under a 1969 variance; however, it is situated in the R20 residential zone.

In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury.

Discover a unique opportunity to own a versatile property in one of Cape Cod's most desirable towns, offering potential as a private residence, multi-family retreat, or investment property. Located less than three-quarters of a mile from the beach, this property has multiple possibilities.

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort.

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.

Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn.

Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic.

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.

The location that has it all...walk to both town, fish pier, beach and baseball games....New Farmhouse with pool built by Morgan and Sons and expecting completion by August 1 st.. Enjoy Chatham from this 4BR 5.5 bath , 3980 sq foot home. All bedrooms offer spacious accommodations with private baths.

Comfortable Cape style 3 bedroom home, close to down-town Chatham Village, Oyster Pond Beach and exceptional dining. Set back from the road on a level, grassy front lawn, Updated chef's kitchen, newer A/C splits, fenced, sunny back yard with deck. Free standing 2 car garage on over .6 acre lot. Unfinished second floor offers expansion potential with previously permitted plan.

Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches, Veteran's Field, and the bike path, this three-bedroom, two-bath home offers an exceptional opportunity in a prime Chatham location. Built in 1994, the 1,802 square foot property includes a one-car garage and full basement, providing a strong foundation for your vision.