Chatham, MA Real Estate | Chatham, MA Single Family Homes for Sale

This special home circa 1865 was completely restored down to the studs with a long list of improvements inside and out. Everything has been done here so you can move in and enjoy the wonderful fall months ahead! A stunning new kitchen is the heart of the home, and features a Bertazonni professional range and hood, white custom cabinets, quartz countertops and center island. Relax in the adjacent family room with a cathedral ceiling, restored stained-glass windows and cozy fireplace. A separate dining room with original tin ceiling opens to a charming front porch. There are 3 bedrooms including an en-suite primary on the 2nd floor. Many of the design choices and renovations in the home reflect the period it was built, further enhancing its appeal. The blend of authentic charm with modern updates creates the perfect Chatham cottage retreat! Amenities include gorgeous wood floors, A/C, natural gas heat, on-demand hot water heater, outside shower, new stone driveway, town sewer connection & much more. The pastoral ¾ acre lot offers a beautiful expansive back yard with field that provides many options, including room for a pool or possibly detached garage. This central location provides easy access to shopping, Chatham and Harwich restaurants, and Nantucket Sound beaches. Come view the Zimri Bassett house and fall in love with this Chatham gem!

1455 Old Queen Anne Rd, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$2,240,000

4 Beds ⋅ 3 Baths ⋅ 73571912 MLS

A meticulously maintained and beautifully decorated beach home awaits you in quaint village of South Chatham.Ideally situated between downtown Chatham and Harwich Port, this exceptional property offers the perfect blend of comfort, privacy, convenience and classic Cape Cod charm.Nestled near Forest Beach,Mill Creek,the Cape Cod Rail Trail, tennis court and conservation areas, this puts nature and recreation at your fingertips.The spacious home features 4 bedroomsand 3 baths providing plenty of room for family and guests. Thoughtfully designed for comfortable living and surround sound for entertaining, the home offers inviting spaces inside and out.The two car garage has been transformed into a fantastic game room complete with air hockey, ping pong and foosball-a wonderful space for kids and adults alike.Outside, the beautifullylandscaped yard and gardens are irrigated by a private well, keeping everything lush throughout the season. Three decks, one is a roof top, outdoor shower,firepit, patio creat the perfect setting for relaxing, entertaining and enjoying the warm Cape Cod evenings.The home is being offered partially furnished.

20 Circle Drive, Chatham

Listing courtesy of Listing Agent: Barbara Carroll-Horne from Listing Office: Gibson Sotheby's International Realty.

$4,000,000

5 Beds ⋅ 3 Baths ⋅ 73571777 MLS

A rare opportunity awaits high above the dunes of Hardings Beach to build the bluff house of your dreams. Nestled within the private enclave of Hall’s Bluff, this five-bedroom home boasts majestic, sweeping views of Nantucket Sound, Monomoy Island, and beyond. The sunsets are spectacular. Ownership includes deeded access to a neighborhood footpath leading directly to Harding's Beach and the Oyster River. Built in 1957, the house is in poor condition, but will be a wonderful project for the right buyer. The house is being sold as.

64 Harbor View, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$5,250,000

4 Beds ⋅ 5 Baths ⋅ 73571701 MLS

Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings define the first floor, anchored by a vaulted beam-ceiling primary suite with a spectacular spa-inspired bath. The generous eat-in kitchen and family room feature a dramatic shiplap-vaulted ceiling and open to a sun-drenched patio surrounding a heated plunge pool and oversize yard with unlimited potential. A second-floor deck overlooks the secluded grounds, while an additional primary en-suite and two bedrooms and two more baths complete the upper level. Stroll to Chatham Bars Inn, the Fish Pier and Main Street - an enviable setting where the best of Chatham is truly at your doorstep.

106 Barcliff Ave, Chatham

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.

$2,600,000

3 Beds ⋅ 3 Baths ⋅ 73570905 MLS

Set on a tranquil dead-end lane in Chatham's Old Village, this 2006-built home pays homage to its 1720 predecessor, blending classic charm with modern living in one of the town's most appealing locations. Just steps from Lighthouse Beach and downtown Chatham, this remarkable property offers an exceptional opportunity for a full-time residence, summer getaway, or investment home. Designed for entertaining family and friends, the main level features a bright, open-concept living area with a cozy gas fireplace, hardwood floors, a distinct dining space, and a light-filled kitchen with a center island and pantry closet. French doors lead out to a private, beautifully landscaped fenced-in yard with a stone patio, gas fire pit, outdoor shower, and a charming shed. A main-floor primary bedroom, full bath, and cozy den or office complete this level. The upper level hosts two additional bedrooms and a full bath. The expansive lower level adds even more versatile space, including an entertainment room, a bonus space for an office or overflow guests, a half bath, and a laundry room.

10 Mill Hill Lane, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.

$4,950,000

3 Beds ⋅ 4 Baths ⋅ 73570275 MLS

Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural lines, light wood floors, and custom built-ins. At the heart of the home lies a soaring vaulted great room anchored by a large stone fireplace, framed by double-height windows and glass French doors that capture panoramic water views.Designed for effortless entertaining and everyday comfort, the main level flows between open gathering areas and quiet retreats. The eat-in chef's kitchen features custom cabinetry and professional-grade appliances, including a Sub-Zero refrigerator, double ovens, and a Thermador range. Adjoining the kitchen, the formal dining room serves as a centerpiece for hosting, complete with built-in display shelving and a cozy window seat, illuminated by a custom glass pendant light fixture suspended from a recessed ceiling. A first-floor en suite bedroom completes the main level, providing refined accommodations for guests or family. On the second level, a light-filled den is equipped with a wet bar, a built-in alcove day bed, and a private balcony overlooking the water. The primary suite serves as a true sanctuary, complete with vaulted ceilings, expansive windows framing water views, and a contemporary fireplace. The spa-like primary bath boasts a deep soaking tub with a wood surround, a glass shower with textured wall tiling, dual-sink vanities with under-cabinet lighting, and connects to a spacious walk-in closet. The lower level offers endless possibilities with a stone fireplace, built-in workstations, additional guest space, and a fully appointed bath with a deep soaking tub. Outside, multi-tiered outdoor spaces - including covered decking, a stone patio, and manicured lawns running down toward the water's edge - offer front-row seats to Chatham's iconic maritime landscape. Whether setting off by kayak for a day on the water or enjoying al fresco entertaining amidst unsurpassed natural beauty, this property represents coastal Cape Cod living at its absolute finest.

103 Aunt Nabby's Lane, Chatham

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$6,990,000

5 Beds ⋅ 6 Baths ⋅ 73569424 MLS

Experience the very best of Chatham living. Few properties offer this extraordinary combination of premium waterfront living and the ability to stroll to everything the historic village center has to offer. Set behind privacy fencing and mature plantings on Oyster Pond, this distinctive home sits steps from your private boat dock and steps from vibrant downtown Chatham. Walk to your morning coffee, acclaimed restaurants, luxury boutiques, fine galleries, the historic bandstand, parades and summer baseball games. Then return home to the water, step aboard your boat, and cruise through Stage Harbor to Nantucket Sound and beyond. The private pier and dock provide coveted tidal deep-water access, while stunning water views are enjoyed from nearly every room. The four-plus one bedroom residence spans three levels of exceptional water-view living with expansive windows, generous gathering spaces, a beautiful primary suite, separate guest quartiers and a rare six-car garage. Bring your vision to masterfully renovate the existing home or design an entirely new custom masterpiece. A truly unparalleled real estate opportunity.

108 Queen Anne Road, Chatham

Listing courtesy of Listing Agent: Dawn Marie Boynton from Listing Office: .

$1,795,000

3 Beds ⋅ 3 Baths ⋅ 73569230 MLS

Steps from Cockle Cove Beach! This gorgeous, pristine 3-bedroom, 3-bathroom home offers the perfect blend of modern updates and beachside living. Located just steps from Cockle Cove Beach and right across the street from the Taylors Pond dock, this spotless property is completely move-in ready. Kitchen & Baths have been beautifully remodeled within the past few years. Walls were opened up to create a bright, seamless flow and allow winter views of Taylors Pond from the kitchen, dining area and the fire placed living room. Generous living spaces feature three distinct family areas to gather, relax, and entertain. A lower-level family room features its own full bathroom. It is the perfect escape for rainy days. Three Full Baths easily accommodate a house full of family and weekend guests. Beautiful, established gardens offer incredible curb appeal and are easy to maintain. The absolute best part of this home is where it sits. Walk right over to Cockle Cove Beach for or launch your kayak or paddle board in Taylors Pond and paddle to Nantucket Sound. Many other important updates and renovations have been completed by the current owners.

23 Taylors Pond Rd, Chatham

Listing courtesy of Listing Agent: Kathleen Phelan from Listing Office: Compass.

$1,950,000

4 Beds ⋅ 3 Baths ⋅ 73567876 MLS

Reaching into the ocean, the road to Chatham follows a path carved by memory, a line etched straight through the geography of the heart. At 4 Williams Way, that coastal journey finds its destination. Tucked away on a five-home cul-de-sac, this 1.5 acre Contemporary Cape Cod offers sanctuary in a prime location, just minutes to downtown Chatham and 1.7 miles to Cockle Cove Beach, all while being sheltered from peak summer traffic. Spanning 2,198 interior square feet, this 4 bedroom, 2.5 bath home marries classic coastal architecture with refined single-level living. The open-concept living area is anchored by a light-filled chef's kitchen featuring a spacious quartz-clad island with seating for four. The primary bedroom suite offers dual walk-in closets and an en-suite bathroom complete with soaker tub and tiled shower. The centerpiece of the property is a dramatic and private outdoor living room. Sheltered beneath a beadboard soffit ceiling, this open-air retreat invites you to settle in with friends and family, light the logs in the Cambridge ledgestone fireplace, and play home movies on the custom inset TV. Beyond the canopy, the patio opens completely to the sky; from there, cross the lawn to the fenced vegetable garden for homegrown ingredients, or head to the detached shed to chart your next project. Back inside, the second floor hosts three additional bedrooms and a full bath. Main floor laundry is smartly located in the half bath. The attached one car garage offers walk-up storage above for seasonal gear and long-term organization. Follow your heart to Chatham and let the salt air settle—4 Williams Way is your canvas for reconnection. All parties to verify information contained herein.

4 Williams Way, Chatham

Listing courtesy of Listing Agent: Erin Terkelsen from Listing Office: LPT Realty, LLC.

$1,695,000

2 Beds ⋅ 4 Baths ⋅ 73561031 MLS

Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 2 spacious en-suite bedrooms with walk-in closets, 3½ baths and extra space in the finished basement with full bath. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the dining and living areas with a gas fireplace. Amenities include Anderson Stormwatch windows, gas heat, central air and underground utilities provide year-round comfort. The finished lower level offers a Jacuzzi bath, antique pine bar, and pool table. Quality construction includes double-dipped cedar shingles, Azak trim and decking, heavy-duty asphalt roof, and three porches (two covered). This south-facing lot offers close proximity to Nantucket Sound. Close to Forest Beach, post office, restaurants, package store, and Cape Cod Rail Trail, this beautifully crafted home offers exceptional quality, comfort and a location in one of South Chatham's most desirable neighborhoods.

43 Tobey Turtle, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$1,795,000

2 Beds ⋅ 2 Baths ⋅ 73561027 MLS

Experience the ultimate waterfront lifestyle in this lovely coastal retreat. Perfectly positioned on the edge of Frost Fish Creek, this charming home captures picturesque water views and is thoughtfully designed for effortless indoor-outdoor living. Enjoy direct tidal access to one of Cape Cod's most treasured waterways. Secure a private mooring and launch your kayak, paddleboard, or boat right from your backyard. Meander through scenic Frost Fish Creek into Ryder's Cove and the sparkling waters of Pleasant Bay, where endless opportunities for boating, sailing, fishing, shellfishing, and exploring pristine beaches await. Continue beyond to discover one of New England's most spectacular estuaries and its gateway to the Atlantic Ocean. The expansive rear deck provides the perfect setting for entertaining guests or simply relaxing beneath the stars while taking in the peaceful waterfront setting and ever-changing coastal views.Buyer is responsible for the design and installation of a septic system. Septic engineering is currently underway to determine whether the property will support a two- or three-bedroom septic system.

71 Rowland Drive, Chatham

Listing courtesy of Listing Agent: Dawn Marie Boynton from Listing Office: .

$1,175,000

3 Beds ⋅ 3 Baths ⋅ 73557909 MLS

When offering please include proof of funds or pre-approval letter. Deposits may be paid via Depositlink or check payable to Compass LLC.

190 Heritage Ln, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.

$8,950,000

4 Beds ⋅ 3 Baths ⋅ 73556482 MLS

The SandBox, an icon of Shore Road, sits on one of the most coveted streets in America, steps from the Chatham Bars Inn - where waterfront estates are generational and cherished. Set on an over one-acre lot with immense private beachfront, the home reflects the architectural heritage of the setting, with classic cedar shake and shingle detailing throughout. A staircase framed by flowering landscaping leads to a bluestone patio and entertaining spaces over the beach, with a private trail to the water's edge -- one of the first points on the Eastern Seaboard to greet the sunrise each morning. Inside, a shiplap-clad great room opens the home for gathering, flowing into dining and kitchen areas with water views from every angle. The primary suite is a retreat framed by its own bay window, while well-appointed guest spaces offer comfort for family and friends. Extensively renovated, the home retains the craftsmanship of its original build - true, enduring Cape Cod character. This is where summers are made. Shore Road beachfront grows more coveted with time, and opportunities like this rarely surface - a chance to secure one of the most aspirational addresses on the entire East Coast.

166 Shore Road, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$4,500,000

4 Beds ⋅ 5 Baths ⋅ 73556459 MLS

Waterfront new construction in one of Chatham's most preeminent locations, minutes from town. This rare half-acre offering on Emery Pond is to be built by R.A. Martin, one of the Cape's premier builders, with select interior finishes and customizations still available to the right buyer. New construction of this scale is exceptionally rare on Cape Cod, offering the perfect mix of estate-level living and an in-town lifestyle, all with stunning water views. The finished residence offers approximately 4,689 square feet of considered living space across three thoughtfully composed levels, with 4 bedrooms and 4 full baths. Sunlit interiors flow effortlessly from kitchen to dining to generous entertaining spaces, opening to a screened porch and deck framing sweeping views of the pond. Outside, a waterfront pool anchors a true outdoor retreat -- a private, resort-style setting for gathering, moments from town. A primary suite anchors the upper level alongside an office and two additional bedrooms, while the lower level offers a fourth bedroom suite and a generous recreation room. A rare opportunity to build new construction with a coveted mix of setting, space, and location on Emery Pond.

66 Ethelma Dr, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$4,250,000

3 Beds ⋅ 4 Baths ⋅ 73552814 MLS

Exceptional waterfront estate offering breathtaking views from nearly every room and a private sandy beach. Lovingly owned by the same family for nearly three decades, this spectacular 3 bedroom, 3.5 bath residence offers three levels of beautifully designed living overlooking Crow's Pond. A grand foyer opens to a dramatic living room with soaring ceilings, a fireplace, walls of windows, and sweeping water views. Glass doors lead from the living room to a deck and patio overlooking the water, creating the perfect setting for entertaining or relaxing. The first floor also features a waterfront dining room, kitchen, spacious primary suite, wood-paneled den, powder room, laundry, and an attached two-car garage. A charming side porch provides yet another inviting outdoor retreat with spectacular water views. Upstairs, two guest bedrooms enjoy water views and share a full bath. The walkout lower level offers a family room, office, full bath, natural light, and excellent storage. Experience Cape Cod's finest waterfront living with boating, kayaking, swimming, and fishing right from your private sandy beach. Ideally located next to Eastward Ho! and a short drive to downtown Chatham.

600 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$2,390,000

4 Beds ⋅ 4 Baths ⋅ 73548377 MLS

Enjoy this retreat like home with two great rooms which can be used for entertaining and family gatherings, an open kitchen with large dining space, a first floor primary with en-suite bathroom including laundry. Wrap around decks taking in nature is at every turn of this unique home. This home has deeded rights to Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

55 Winterset Drive, Chatham

Listing courtesy of Listing Agent: Janet Stuart from Listing Office: Coldwell Banker Realty - Concord.

$1,469,000

5 Beds ⋅ 10 Baths ⋅ 73548115 MLS

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 shingle-style exterior is substantial and classic Cape Cod, with a two-car garage and a private boat dock giving direct access to the water. The open, airy living room has a stone fireplace, window seats and vast water views throughout. The kitchen continues the view with a Wolf gas range, a large island with seating and doors opening to an expansive deck overlooking Crows Pond. The three-level layout includes a quiet office, a lower-level gym, an indoor sauna and a guest suite with its own full kitchen and living room. An elevator connects all floors. The pool, patio and private boat dock anchor Fox Hill's outdoor sequence, with sunrise and sunset views in one of Cape Cod's most storied seaside towns.

558 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$5,900,000

4 Beds ⋅ 5 Baths ⋅ 73544856 MLS

Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and rooms and additions in several directions in this very private location of North Chatham....Choice of three 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 heated Gunite pool...Property has been very well maintained by the current owner who has been here for over 36 years and completed a new roof, many new windows, new bedroom addition, newer family room addition and more.....All information here has not been independently verified and buyer should do his/her own due diligence by checking with their attorney, and zoning and building rules and by laws, etc....Assessment numbers subject to change with new Fiscal Year.

95 Cotchpinicut, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.

$995,000

3 Beds ⋅ 3 Baths ⋅ 73538377 MLS

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.Offering 1,754 sqft of main-level living, the home many features include an updated eat-in kitchen, large living room with fireplace, and a dining room that leads you towards two distinct, comfortable sitting areas that open to expansive decks with winter water views. 1632 sf of additional finished space in the walkout lower level add tremendous flexibility. Recent improvements include a new roof, new windows, kitchen renovations, and cooling systems. Generous living spaces, thoughtful updates, and a serene Chatham setting, make this home ready to be enjoyed for years to come.

65 Captain Kendrick Dr, Chatham

Listing courtesy of Listing Agent: Barbara Garside from Listing Office: eXp Realty LLC.

$2,100,000

1 Beds ⋅ 2 Baths ⋅ 73535300 MLS

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. There are 5 private in-town parking spaces behind the building and is located in the coveted GB-1 zoning district that has the most versatile business-use options available. The first floor commercial space features an open floor plan with 3 large areas and 4 oversized showcase windows putting your business directly in front of passing pedestrian traffic. The second floor apartment was fully renovated in 2019 and includes one bedroom, a full bath and laundry, and an open concept kitchen and a living area with vaulted ceilings. A large mahogany deck provides excellent outdoor living space. Both floors are independent of one another with separate A/C and heat.

409 Main St, Chatham

Listing courtesy of Listing Agent: Rick Smith from Listing Office: Gibson Sotheby's International Realty.

$6,500,000

10 Beds ⋅ 10 Baths ⋅ 73535185 MLS

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. The home offers over 7,500 sq ft with 10 bedrooms and 10 bathrooms. Inside, enjoy hand-painted murals, sweeping water views, curved staircases, intricate woodwork, and beautifully scaled living spaces filled with character. The lower level features a ''speakeasy'', ballroom, workshop, and storage. Outside, expansive terraces, mature gardens, bluestone walkways, towering trees, and rolling lawns create a spectacular setting leading toward the water. The property was divided into three townhouse residences, but has since been used as a single-family home. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$5,900,000

6 Beds ⋅ 8 Baths ⋅ 73533378 MLS

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 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every bedroom ensuite. An open-concept great room with soaring ceilings anchors the floor-plan, while a fully finished basement provides a complete auxiliary level for guests and entertaining — a depth of program rarely found. Outside, a pool and integrated jacuzzi anchor the aquatic experience, framed by a dramatic firewall feature and wraparound deck purpose-built for outdoor living at scale. Constructed by R.A. Martin — among the most trusted names in Chatham construction — the property offers a rare opportunity to customize finishes to suit. A singular proposition in the Chatham marketplace!

50 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$1,250,000

3 Beds ⋅ 2 Baths ⋅ 73531412 MLS

Canoe and kayak on Mill Pond. Direct water front at the end of the cul-de-sac. Turn key - Fully furnished year round and off season rental histoy. Very private and peaceful setting yet conveninet to shopping, restaurants, beaches and highways. 3 Bedrooms, 2 baths. First floor master. Plenty of closet space. Walkout basement. Large deck overlooking Mill Pond. Gas fireplace instert. Gas stove. Washer and dryer. May assume summer rentals.

35 Duncan Lane, Chatham

Listing courtesy of Listing Agent: John Habeeb from Listing Office: Alliance Realty Advisors, Inc..

$4,995,000

4 Beds ⋅ 4 Baths ⋅ 73529657 MLS

Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed to maximize its breathtaking setting, the light-filled open floor plan features walls of glass and stunning water views from nearly every room. The main level includes a spacious living room with fireplace, dining area, updated kitchen, two bedrooms, and a shared bath. Upstairs, two private en-suite bedrooms enjoy elevated harbor vistas. The walkout lower level offers a family room and fitness space overlooking the water. A 2025 kitchen renovation, 2019 revetment, direct water access for kayaking, paddleboarding, fishing, clamming, and swimming, make this an exceptional opportunity.

56 Stage Island Road, Chatham

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.

$1,899,000

3 Beds ⋅ 3 Baths ⋅ 73519558 MLS

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. Thoughtfully designed for gathering, relaxing, and entertaining, this one-of-a-kind property offers the charm of a custom retreat with the functionality of today’s living. Ideally located close to beaches, shopping and restaurants. With deeded rights to the private beach just steps away, a beautiful landing to launch your kayaks. This is a truly distinctive home with architectural character, inviting spaces, and an unforgettable sense of place. (Moorings should be available on Taylor's Pond with a relatively short waitlist, check with the Harbormaster!)

70 Uncle Deane's Rd, Chatham

Listing courtesy of Listing Agent: Patrick Davison from Listing Office: .

$4,950,000

4 Beds ⋅ 5 Baths ⋅ 73518596 MLS

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. It is framed by masterful stonework, open-air living spaces, and artisanal native plantings--setting a captivating tone before you even step inside. The foyer sets the stage for the exceptional design that unfolds within. Built by Steven Nickerson, meticulous millwork, custom Kochman Reidt+Haigh cabinetry accentuating many spaces, and intricate architectural details are found throughout the home. The house boasts an extraordinary level of artistry and craftmanship. The main living room with fireplace is refined yet comfortable and flows seamlessly into an intimate sitting area, partitioned by a custom-built cabinet containing a motorized TV lift, creating multi-use spaces.

15 Bay Lane, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$4,200,000

3 Beds ⋅ 3 Baths ⋅ 73515489 MLS

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. The open main level is anchored by an arched fireplace wall that flows into a dramatic two-story dining area and reading loft, both set off by a soaring wall of windows with water views. The chef’s kitchen offers bar seating, while a versatile bedroom or study, full bath and mudroom complete the floor. The primary suite is a quiet retreat, featuring a fireplace, built-in bookshelves, a window seat and a luminous stained-glass accent window. A second guest suite with vaulted ceilings completes the upper level. The walk-out lower level provides generous family space, custom built-ins, abundant storage and room for expansion. Outdoors, mature plantings, stonework, a large deck and a pergola.

30 Indian Trail, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$2,850,000

3 Beds ⋅ 3 Baths ⋅ 73513527 MLS

Stage Island is among the most exclusive addresses on Cape Cod — a private 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 1.07 waterfront acres, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is truly generational. Marsh-front access invites kayaking and quiet recreation, while wildlife and natural beauty frame everyday life. The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light, anchored by a wall of windows and doors with 270-degree views. The private primary suite offers its own deck and a soaking tub with waterfront views — an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks create multiple zones for alfresco dining, yard games, and summers well spent. A setting this rare does not come twice!

336 Stage Island Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$2,950,000

4 Beds ⋅ 4 Baths ⋅ 73511079 MLS

TURNKEY!! Just open the door to one of Chatham's most desirable neighborhoods, a timeless single-family residence, set on over 40 sq. ft. of manicured land, presents an exceptional opportunity for sophisticated coastal living. This property, maintained in great condition, embodies a refined aesthetic and functional design. The kitchen, thoughtfully designed for both culinary pursuits and social engagement, features stainless steel appliances, stone counters, and a convenient peninsula. Its open-plan configuration seamlessly connects with the living room, enhancing the flow for entertaining, and includes a built-in microwave and a high-end range. The living room serves as a central gathering space, distinguished by a fireplace that provides warmth and ambiance. Integrated built-in shelves offer both display and storage solutions, complementing the rich hardwood flooring that extends throughout. 4 bedrooms, 3.5 baths, and oversized 2 car garage with staircase to loft, a walkout finished basement complete wonderful house

60 Harbor Hill Rd, Chatham

Listing courtesy of Listing Agent: Jacqueline Casey from Listing Office: Shore Road Realty, LLC.

$4,295,000

4 Beds ⋅ 4 Baths ⋅ 73509923 MLS

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 & dramatic walls of glass fill the home with natural light and frame spectacular sunsets. Multiple sliders open to an expansive wraparound deck for effortless indoor-outdoor living. Chefs kitchen, dual living areas, and adjacent open dining create an exceptional setting for relaxing or entertaining. There's nearly 5,000 sq on three levels, with 4 bedrooms and 3.5 baths. The luxurious primary suite offers panoramic water and sunset views. A finished multi-room lower level includes family room and convenient kitchenette. Solar panels, generator, gas heat, Central A/C, outside shower, reclaimed wood floors & more. You'll enjoy a seasonal dock/catwalk on Bucks Creek for kayaking, paddle-boarding, or clamming from your own back yard - and the calm waters of Harding's Beach are a short stroll via sidewalk. Don't miss out!

38 Indian Trail, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$5,750,000

5 Beds ⋅ 5 Baths ⋅ 73506909 MLS

Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat w/tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for guests. A walk-out lower level expands living space with an entertainment room and full bath. New HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham PLUS deeded rights to a boat house steps away!

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$5,850,000

5 Beds ⋅ 6 Baths ⋅ 73495151 MLS

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 storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$4,250,000

4 Beds ⋅ 6 Baths ⋅ 73493426 MLS

The location that has it all...walk to both town, fish pier, beach and baseball games... New Farmhouse being built by Morgan and Son is well underway and expecting completion by July. Enjoy Chatham from this 4BR 5.5 baths, 3980Sq foot home. All bedrooms offer specious accommodations with private baths. First floor boasts a primary suite, an inviting study, living room with vaulted ceilings large slider with views overloooking the new pool and patio area, airy chef's kitchen and dining area. A detached outer building houses a one car garage and a seperate

222 Barcliff, Chatham

Listing courtesy of Listing Agent: Lori Fanning Smith from Listing Office: Compass.

$4,500,000

4 Beds ⋅ 4 Baths ⋅ 73492591 MLS

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. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water and doors to an expansive waterside deck. A versatile layout supports single-level living, featuring a first-floor suite currently enjoyed as a family room with a fireplace, soaring ceilings, full bath, and access to the deck. The upper level includes three bedrooms and a den, all benefiting from stunning outlooks. Professionally designed grounds provide a sense of seclusion, complemented by a private footpath to the shoreline. An exceptional offering in one of Chatham's most coveted waterfront locations.

346 Morris Island Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$4,500,000

6 Beds ⋅ 7 Baths ⋅ 73479712 MLS

Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.

48 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$2,295,000

3 Beds ⋅ 3 Baths ⋅ 73477537 MLS

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. 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 FP & wet bar for relaxed moments overlooking koi pond& garden.The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace & skylit seating area, which flows to the tranquil stone patio for outdoor dining, BBQ.1st FL primary suite with sitting room and en suite bath. Plus lower level office 300 Sq ft, 2 car garage, AC, generator, gas heat, irrigation. Seller to install new 3 BED septic & new 2nd FL heating/AC system. Adjacent Building lot 20,737 Sq ft available for sale $650,000 PIN #73528474 after the house is sold or as a package. 2026 Frost Fish Crk Restoration project for tidal flow in progress.

41 Court St, Chatham

Listing courtesy of Listing Agent: The Nickerson Power Group from Listing Office: Compass.

$829,000

3 Beds ⋅ 2 Baths ⋅ 73460325 MLS

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. There is natural gas and town water in the road, The wood burning fireplace creates ambiance when sitting in the family while relaxing with a good book or watching TV. The yard is filled with beautiful perennials that explode throughout spring and summer. The seller will install a new septic and hook up to town water.

33 Duck Marsh Ln, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.

$2,800,000

3 Beds ⋅ 2 Baths ⋅ 73457238 MLS

Professional photos coming soon! 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. Take in spectacular water views and unforgettable sunsets, with private stairs leading down to the water’s edge of Bucks Creek for easy access and serene enjoyment. Inside, the home is a pleasure to show, highlighted by a wonderful sunroom that captures the light and scenery year-round. A rare opportunity to enjoy Chatham living at its best. An abutting property, 92 Indian Trail, is available for $3,200,000.

78 Indian Trail, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$3,200,000

3 Beds ⋅ 3 Baths ⋅ 73457239 MLS

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 setting within a friendly association that features an association dock on Bucks Creek, complete with kayak storage and a picnic area—ideal for effortless days on the water. The home is enhanced by EV charging station and owned solar, offering exceptional energy efficiency and savings. Thoughtfully designed, light-filled, and meticulously cared for, it is truly a delight to show. Come experience the charm, serenity, and coastal lifestyle this Bucks Creek gem has to offer. An abutting property, 78 Indian Trail, is availbale for sale at $2,800,000.

92 Indian Trail, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$789,000

3 Beds ⋅ 2 Baths ⋅ 73435928 MLS

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. A one-car garage and large unfinished basement sits below the home, and the property sits on roughly ½ acre, offering space for outdoor activities or gardening. While in need of some updating, recent upgrades include Roof, Furnace, gas water heater, electrical, and it provides solid value and strong potential in a sought-after location that is close to local amenities.

49 Duck Marsh, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$5,495,000

2 Beds ⋅ 3 Baths ⋅ 73419421 MLS

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 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes.

99 Uncle Alberts Drive Ext, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.

$3,595,000

3 Beds ⋅ 5 Baths ⋅ 73371097 MLS

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat ''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 w/walnut top offers space for casual dining & flows to the dining area. The nearby butler's pantry enjoys a Subzero beverage fridge. The inviting living area w/gas fireplace opens to a 3-season porch and is adjacent to the deck that overlooks conservation. The 1st story primary suite boasts an ensuite bath w/radiant floor heat & walk-in closet. The 2nd story features 2 en-suite bedrooms, family room & home office. Finished lower-level w/9'' ceilings, a full bath, & 725 sq ft. Cedar roof, copper downspouts, generator & irrigation by well. With its prime location, its an easy walk to town & the beach.

287 Cedar St, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.

$1,650,000

1 Baths ⋅ 73258353 MLS

Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to be finished. Lots of possibilities - documents attached include Gb3 standard permitted uses section 3.4 and Appendix 1 ''Schedule of Use Regulations'', floor plans, and septic site plan. Great opportunities-previously a builders work shop and warehouse for storing automobiles, boats, vintage motorcycles etc. The solar panels are owned. Please verify all information contained herein. Don't miss this special property!

231 Crowell Road, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

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