Chatham Massachusetts Real Estate & Homes For Sale

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.

Newly renovated and beautifully refreshed, this exceptional 4-bedroom, 3.5-bath home is set in one of Chatham's most sought-after neighborhoods, within an exclusive enclave near Oyster Pond and surrounded by remarkable properties.

Nestled in a premier Stage Harbor location, this 4-bedroom, 2-bath property presents an exceptional redevelopment opportunity. Just a short stroll from the beach, boat launch, yacht club and nestled in a prestigious neighborhood, the value lies in this coveted setting. Bring your builder and architect to create a new, luxurious custom home on this prime piece of real estate.

Positioned in the heart of Chatham, 894 Main Street presents a rare mixed-use investment in one of Cape Cod's most visible and enduring locations. Directly across from Chatham Village Market, this iconic Main Street address benefits from exceptional foot traffic, strong frontage, and effortless walkability to the town's most desirable destinations.

Welcome to Chatham! Be in for summer and enjoy this move-in ready, meticulously maintained home offering comfort and easy location to beach and restaurants. The open floor plan is perfect for entertaining, with bright living spaces that flow seamlessly throughout. The chef's kitchen showcases high-end finishes, premium appliances, custom cabinetry, and a spacious island ideal for gathering.

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.

PONDFRONT: Welcome to 118 Wilfred Road, a charming Cape-style home tucked into one of Chatham's beloved ponds settings. With 3 bedrooms, 3 baths, and 1,804 square feet, this inviting residence captures the essence of relaxed Cape Cod living. Enjoy sweeping views of Black Pond, White Pond and Emery Pond and take advantage of an exceptional location less than 0.

Part of the historic Christopher Ryder House, this elegant two-bedroom, three bath condominium blends one floor living with timeless architectural charm. The residence offers beautifully proportioned rooms, high ceilings, large sun-filled windows, and warm wood floors throughout.

The location that has it all...walk to both town, fish pier, beach and baseball games....New Farmhouse being built by Morgan and Sons is well underway and expecting completion by July. 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.

Conveniently located just off Rt 28, this two-story office building features a separate seven-unit storage bay building in the back. Situated on 1.21 acres, it offers excellent income potential of over $175,000 annually and is close to everything in Chatham and Harwich Port...Completely renovated and redone in 2013...

Park Place is the Premiere Chatham address for an easy-care, maintenance-free lifestyle! These apartment-style condos cater to age 62+ residents seeking to enjoy a walkable location in Town, numerous opportunities for social engagement (including daily continental breakfast and Friday night cocktails), an exercise room, library, guest suite, garage parking, elevator and more.

39 Jedidiah Way, has been gently utilized by the same family for the past 29 years, serving as a reliable summer retreat. Situated on a .5-acre elevated lot overlooking a wooded cul-de-sac, this property boasts direct access to the Old Colony Rail Trail, a unique feature among current Chatham offerings.

Tucked within a coveted North Chatham setting of Harbor Coves and offering access to a private association beach, this exceptional Gambrel-style residence currently under construction with Harbor Builders presents a sophisticated coastal retreat.The property offers generous indoor and outdoor living spaces on a half an acre.

Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha's Vineyard Interior Designs. Walls of glass frame sweeping vistas and invite natural light to pour in throughout the home.

Beautifully renovated inside and out oceanfront townhome nestled in the heart of Chatham. Fully furnished 2 bedroom, 2 bathroom home offers the epitome of Cape Cod living with breathtaking ocean views and private association beach access just steps from your door. Wake up to stunning sunrises over the water. The vaulted ceilings allow natural light to fill the bedrooms.

A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels.

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.

This high-visibility commercial property is ideally situated on Route 28, a primary thoroughfare leading into the upscale, vibrant heart of downtown Chatham. Currently operating as a successful barber shop, and a hair salon before that, the 600 square foot building enjoys a prominent corner lot position with it's own dedicated parking spaces, front and rear.

Ideally situated just moments from Chatham's Village boutiques and restaurants, this exceptional three bedroom,two bath residence captures the essence of Chatham coastal living. Privately set on a private dead-end street, the property offers tranquility and also convenience in one of Chatham's most desirable settings.

Set within a private gated enclave in South Chatham's emerging luxury corridor, 48 Sylvan Way is a singular estate retreat discreetly positioned just moments from the Cape's most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational potential, the property offers rare privacy, scale, and versatility in one of Chatham's most compelling locations.

Inviting 1,583 +/- SF commercial space ideally suited for professional offices, creative firms, or service-oriented tenants. Enjoy a versatile layout featuring three distinct office areas plus two additional private rooms, a generous 550 SF shared workspace, a half bath, and a full kitchen -- perfect for flexible daily operations.

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 building lot 20,737 sq ft.. Wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship.

Set within the prestigious Harbor Coves enclave of Oyster Harbors overlooking Ryders Cove, this exceptional North Chatham waterfront residence offers refined coastal living at its finest. A dramatic entry reveals a showstopping living room with soaring cathedral ceilings and walls of glass framing panoramic water views.

Set on nearly an acre in one of Chatham's most coveted enclaves, this Stage Island residence offers an extraordinary combination of refined craftsmanship and sweeping Stage Harbor views. The welcoming foyer opens to a dramatic living room with walls of glass framing the water, filling the space with natural light.

A fantastic opportunity to purchase a building on a highly trafficked corner lot in the downtown area of Chatham. This 2,015 square foot office space opens up to an open floor plan with 20+ desks. Equipped with the amenities any business needs. Located at the intersection of Crowell Road and Main Street, adjacent from the famous Chatham Village Market. Tenants in place.

Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the quintessential Cape Cod lifestyle. Situated in the sought-after Quitnesset community, this elegant property is perfect for making lasting memories.

Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation.

NEW CONSTRUCTION - NORTH CHATHAM, 02650. Introducing a newly built luxury residence offering sophisticated coastal living and exceptional craftsmanship in one of Chatham's most prestigious enclaves.

Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated with hardwood throughout, this 3 bedroom, 2.5 bath home offers a comfortable floor plan including a first floor primary ensuite bedroom and 2 large guest bedooms and bath on the second level.

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.

Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water.

Co-ownership opportunity. Own one-eighth of this turnkey home, professionally managed by Pacaso.

Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace.

One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes at this stage with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyers.

One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes and extras at this stage of construction with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyer.

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.

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.

NICKERSON CORNERS . . . Spacious corner office of 1,123 sq ft. Great location in North Chatham. Lots of parking and ease of access. Take next steps to grow your business in prestigious North Chatham location. Sold AS IS, but ready for your custom touches. Make it yours today and grow easily into the new century.

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.

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.

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.