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$1,200,000
4 Beds ⋅ 2 Baths ⋅ 73575812 MLS
Set in coveted South Chatham less than 1/2 mile to the warm waters of Nantucket Sound, this home has been meticulously maintained by the same owners for the past 20 years and is ready for its next chapter. A flexible floor plan offers two distinct living spaces—a more traditional living room with fireplace and a spacious open-concept great room perfect for gathering and entertaining. With two bedrooms on the first floor and two more upstairs, there's plenty of room for family and guests while offering the convenience of first-floor living. Step outside to a maintenance-free deck and adjoining patio, complete with a new outdoor shower—a Cape Cod summer essential! Beyond, the expansive and private backyard offers a wonderful canvas for whatever you desire, from gardens and outdoor entertaining spaces to simply enjoying the peace and privacy of your own backyard retreat. Comfortable and inviting as it stands today, the home also offers exciting potential for a new owner to update, personalize, and create something truly special. Whether you're searching for a year-round home, summer escape, or investment opportunity, this home combines it all. Bring your vision and make it your own!

122 Forest Beach Rd, Chatham

Listing courtesy of Listing Agent: Sharon Mabile from Listing Office: .
$2,499,000
2 Beds ⋅ 2 Baths ⋅ 73574801 MLS
Perched in one of Chatham's most sought-after coastal neighborhoods, 72 Ridgevale Road South is a rare Cape Cod offering with sweeping views of Bucks Creek, Nantucket Sound, and Ridgevale Beach. Rebuilt in 2002 and beautifully maintained, this move-in ready Chatham home captures sparkling water views from nearly every angle and offers the coastal lifestyle buyers come to Cape Cod to find. A private dock, shared through an intimate seven-member association, provides coveted access to Bucks Creek and beyond, ideal for boating, kayaking, paddleboarding, and enjoying life on the water. The neighborhood association also includes a nearby parking area for added convenience, all for just $200 per year. Additional features include gas heat, a Generac whole-house generator, a new roof, irrigation connected to town water, and a classic outdoor shower. Seller is designing a new septic, install will be buyer responsibility. With dock access, exceptional water views, proximity to Ridgevale Beach, and a prime Chatham location, this is a truly special property for year-round living, a second home, or a Cape Cod retreat.

72 Ridgevale Rd So, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$875,000
3 Beds ⋅ 2 Baths ⋅ 73574852 MLS
This classic Colonial-style home is set on a quiet road ending in a cul-de-sac, close to the Cape Cod Rail Trail and Nantucket Sound beaches. The welcoming first floor features a living room with a wood-burning fireplace, a spacious dining room with hardwood floors, an eat-in kitchen, a bedroom, a bath, and a convenient laundry area. An enclosed, unfinished breezeway offers the potential for a future mudroom and connects the home to an oversized two-car garage. Upstairs are two additional bedrooms, including one with a private balcony deck, along with a full bath and a comfortable sitting room w/fireplace that could also serve as a home office. Additional unfinished space above the garage and breezeway provides exciting possibilities for future living space, a guest suite, studio, or potential accessory dwelling unit, subject to applicable approvals. Highlights include hardwood floors, two fireplaces, oil heat, town water, split-system air conditioning, flexible spaces, passing Title V septic inspection report and wonderful expansion potential in a desirable South Chatham location.

31 Old Village Rd, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$975,000
3 Beds ⋅ 2 Baths ⋅ 73570542 MLS
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.
$2,295,000
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.
$975,000
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.

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