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$12,000,000
4 Beds 3 Baths 22603612 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 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 private 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

$950,000
3 Beds 1 Baths 22603601 MLS
This charming cottage is in a coveted location close to Hardings Beach and Barn HIll town Landing with iconic oyster shanties and access to Oyster River, Stage Harbor for kayaking & paddleboarding. 2 marinas are also nearby for boating fun not to mention all the local dining options and bike trail. This adorable quintessential Cape Cod cottage has been updated with newer kitchen and bath, skylights, decorated with panache enhancing summer rental investment. Detached 2 car garage is a bonus and the unique '' sleeping under the stars'' porch in the trees adds to the ambiance, creating memorable happy summers in Chatham. Connected to town sewer on a level 23, 741 sq ft lot, it offers many possibilities for potential expansion. Furnace non functional, buyer to install new one or mini splits for heat/AC if desired. Opportunity Knocks! Showings ONLY on Sunday rental turnover days July 26th, Aug 2nd, Aug.16th only 12-3PM.

268 Barn Hill Road, Chatham

$695,000
2 Beds 1 Baths 22603438 MLS
Nestled on a private lane in one of Chatham's most sought after locations, this home has been enjoyed by the same family since 1946 and occupied as a year round home for 40 years. This is a rare opportunity to create your own Cape Cod retreat just moments from Oyster River, the Oyster River Boatyard, and nearby Hardings Beach. Bring your vision to the charming, light-filled home full of original character, vaulted ceilings and ready for its next chapter. Whether you're dreaming of restoring its vintage charm or exploring future possibilities, this is a rare chance to own in Chatham. The property is being sold AS IS. Buyers should anticipate the need for a new Title V septic system and replacement of the existing oil tank to meet current town requirements. All information contained herein is deemed reliable but is not guaranteed. Buyers & buyers agents should perform their own due diligence regarding future use and development potential and independently verify all information.

40 Uncle Abner's Path, Chatham

$9,995,000
3 Beds 3 Baths 22603522 MLS
Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and possibility. Beyond the home's welcoming presence, a surprisingly private landscape unfolds, where mature plantings, a sweeping lawn, a carriage-style garage, and a swimming pool create an extraordinary retreat. Inside, the home was designed for gracious living, with spacious rooms and classic details, equally suited to entertaining or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs, charming windows frame picture-perfect coastal scenes. Whether enjoyed as it is today or reimagined, this is a rare opportunity to begin its next chapter. This special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Road, Chatham

$795,000
4 Beds 4 Baths 22603514 MLS
Tucked away on a cul-de-sac in W. Chatham this spacious 4 bed/ 3.5 bath Cape offers potential in a peaceful setting. Set back from the road with a canopy of trees, this property feels private & serene with seasonal views of a scenic cranberry bog & birdlife. The main level features an open sunny living/dining area, 2 picture windows & slider to wraparound deck, hardwood floors and wood burning Fireplace. The good sized kitchen has wet bar and Breakfast bar seating, Stack WD laundry& pantry area, plus half bath in hallway. The 1st Fl primary bedroom is ensuite with bath. Upstairs are 3 good sized bedrooms, full bath & ample storage closet. The 674 sq ft finished walk out lower level with separate entrance slider offers flexibility for office, TV entertainment room with built in bar ready for gatherings. Nearby is the CC Rail Trail access for biking/ walking or Marion's Pie shop for coffee, a short drive to Ridgevale Beach. Excellent opportunity for next owner to bring their vision and updates to make it truly shine. Great for year round or vacation rental options...lots of possibilities with 3 levels of living space.

19 Joshuas Way, Chatham

$4,250,000
3 Beds 4 Baths 22603504 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 Road, Chatham

$2,390,000
4 Beds 4 Baths 22603375 MLS
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

55 Winterset Drive, Chatham

$1,469,000
5 Beds 10 Baths 22603353 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 classic shingle-style exterior includes a two-car garage and private boat dock with direct water access. The airy living room features a stone fireplace, window seats, and vast water views. The kitchen continues the view with a Wolf gas range, a large island, and doors opening to a deck overlooking Crows Pond. A formal dining room with raised panel walls and a butler's pantry with wet bar completes the main level. The three-level layout includes a quiet office, lower-level gym, indoor sauna, and a guest suite with its own kitchen and living room, all connected by an elevator. A pool, patio, and private dock anchor the outdoor spaces, with sunrise and sunset views from multiple balconies. Lighthouse Beach is close by, and Chatham's Main Street offers galleries, restaurants, and shops. Professionally managed by Pacaso and ready when owners arrive.

558 Fox Hill Road, Chatham

$5,900,000
4 Beds 5 Baths 22603274 MLS
Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and additions in several directions in this very private location of North Chatham...Choice of 3 primary bedrooms with attached baths... Views over Chatham Harbor and beyond.......Beach and boating just an easy walk away. Or swim and relax in your own backyard in the recently retiled heated Gunite pool....House 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 Road, Chatham

$2,995,000
4 Beds 4 Baths 22603172 MLS
Perfectly positioned to capture breathtaking sunsets over Bucks Creek, this meticulously updated 2,700-square-foot residence features 4 bedrooms and 3.5 bathrooms. Just a short distance from Nantucket Sound and Hardings Beach, this craftsman-renovated home offers a spacious open floor plan highlighted by vaulted, beamed ceilings and expansive windows that showcase ever-shifting views of the tidal marsh. Designed to host guests, the first floor includes a stunning professional-grade kitchen with an oversized quartz island that opens to an elegant dining area, two fireplaces, and two primary bedroom suites. The property is rounded out by a large wrap-around deck, two additional second-floor bedrooms, a one-car garage, and a full basement with heat and air conditioning. The house is .7 mi from Harding's Beach and 1.9 miles from downtown Chatham's shops and restaurants. Pull up a chair and savor Mother Nature's ever-changing show.

26 Hardings Beach Road, Chatham

$1,069,000
3 Beds 3 Baths 22602982 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 Drive, Chatham

$6,500,000
10 Beds 10 Baths 22602857 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. In 1978, the property was divided into three townhouse residences, each with private entrances, kitchens, living areas, laundry, terraces, and separate utilities. The property has since been used as a single-family home, but offers remarkable flexibility as either a grand estate or redevelopment opportunity. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham

$1,199,000
4 Beds 3 Baths 22602848 MLS
Welcome to Riverbay Estates, where Cape Cod charm meets endless potential. Enjoy peaceful mornings and beautiful water views from nearly every room in this spacious home. This, well-built 4-bedroom, 3-bath home offers direct access to Pickerel Pond for kayaking and enjoying nature. A true ''diamond in the rough'' project with great bones ready for your updates and personal vision. The, main level features a living room, dining area, kitchen, first-floor primary suite, guest bedroom, and full bath. Upstairs are two additional bedrooms, a full bath, and two expansive walk-in attic spaces offering exceptional storage or future expansion potential. Additional, amenities include first-floor central A/C, natural gas heat, an attached two-car garage, and generator ready. Tucked away in a quiet neighborhood just minutes from Chatham's Main Street, Pleasant Bay, beaches, shopping, and dining, this is a rare opportunity to create your dream Cape escape

68 Chippingstone Road, Chatham

$2,100,000
1 Beds 2 Baths 22602838 MLS
Location,Location, Location ! 409 Main Street in the heart of downtown Chatham Village offers a rare and highly desirable combination: a mixed use building with first floor commercial space with showcase windows, maximum retail exposure and heavy foot traffic along with a fully renovated spacious separate second floor of residential living. 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. Don't miss this opportunity to own a versatile property that offers both exceptional business potential and strong investment value. Seller is the Owner/Broker.

409 Main Street, Chatham

$849,000
2 Beds 1 Baths 22602398 MLS
Tucked away in the heart of Chatham, 66 Snow Lane offers a rare blend of privacy, convenience, & natural beauty. This charming 2-bedroom, 1-bath ranch-style home is surrounded by conservation land, creating a peaceful setting where birds, wildlife, and wooded views can be enjoyed from every window. Thoughtfully designed for easy one-floor living, the home features a wood burning fireplace, first-floor washer & dryer, gas heat, and central AC, outdoor shower, newer shed, making it a comfortable retreat in every season. While the setting feels quiet & removed, the location is wonderfully close to everything that makes Chatham so special. Just 0.4 miles to the village and Veterans Field and a 5 min walk to Oyster Pond. You can stroll into town for shopping, restaurants, theater, movies, and summer baseball, then return home to the calm and privacy of your own little escape. Whether you are looking for a year-round residence, a Cape Cod getaway, or a low-maintenance retreat near the center of town, this delightful home offers the best of both worlds: in-town convenience with the feeling of being away from it all. Sewer at the road, hook-up is designed & ready for the buyer to connect.

66 Snow Lane, Chatham

$4,395,000
4 Beds 6 Baths 22602319 MLS
Situated on Chatham's exclusive Stage Island, this 4 BR, 5.5 bath, shingle-style residence is designed for seamless indoor and outdoor entertaining. The bright, airy first floor is anchored by a great room with a Rumford fireplace, custom cabinets, 10' ceilings, and towering windows. The professional-grade kitchen features premier appliances, a pantry, a wet bar, and a large center island. Primary suites are on both floors, each with a large walk-in closet and a luxurious bath. The fenced-in yard offers two exceptional options for installing a large swimming pool and spa to complement the bluestone patio and built-in gas grill. The second story features an inviting family room with custom-built-ins and a gas fireplace, opening onto a broad deck with views of the Atlantic Ocean and the Outer Beach. The second-floor primary is complemented by two well-appointed guest suites. A private staircase leads to the bonus room with a full bath, located above the two-car garage and ideal for a gym, office, or guest accommodations. A whole-house generator and an in-ground irrigation system supplied by a private well add to what is an unparalleled value in the Chatham real estate market.

335 Stage Island Road, Chatham

$4,950,000
4 Beds 5 Baths 22602178 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. Smart home technology enhances both functionality and ambiance throughout.

15 Bay Lane, Chatham

$4,200,000
3 Beds 3 Baths 22602056 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 patio create a seamless connection to the landscape. As part of the Bucks Creek Association, residents enjoy access to a private picnic area and dock on Nantucket Sound. The nearby Cape Cod Rail Trail offers an easy, scenic ride to downtown Chatham and surrounding towns.

30 Indian Trail, Chatham

$2,995,000
3 Beds 3 Baths 22601983 MLS
Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, this property delivers a generational setting defined by sweeping marsh and water views, breathtaking sunsets, and a bucolic lot surrounded by abundant conservation land.The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light. A wall of windows and doors anchors the main living area with 270-degree views. The private primary suite features its own deck and a soaking tub with waterfront views -- an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks unfold into multiple entertainment zones designed for alfresco dining, yard games, and summers well spent. Move-in ready and meticulously maintained, the expansive footprint also offers meaningful runway for further development. A setting this rare, in a community this sought-after, does not come twice.

336 Stage Island Road, Chatham

$4,495,000
4 Beds 4 Baths 22601752 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 and dramatic walls of glass fill the home with natural light and frame spectacular sunsets; while sliders open to an expansive wraparound deck for effortless indoor-outdoor living. A chef's kitchen, dual living areas, and an open dining space - all framed by stunning views - create an exceptional setting for entertaining. Offering nearly 5,000 sq ft across three levels, you'll enjoy four bedrooms and 3.5 baths, highlighted by a luxurious primary suite with panoramic views. Multiple living spaces provide flexibility for quiet relaxation or hosting guests. The walk-out finished lower level features several rooms plus a convenient kitchenette. A seasonal catwalk leads to Bucks Creek for kayaking, paddle-boarding, or clamming, and the calm waters of popular Harding's Beach are only a short stroll. Other notable features include reclaimed wood floors, 3 fireplaces, natural gas heat, Central A/C, generator, outdoor shower, 2-car garage, and rental history. Paradise found in one of the most coveted towns on Cape Cod!

38 Indian Trail, Chatham

$3,390,000
4 Beds 4 Baths 22601737 MLS
Tucked away in Chatham's most desirable residential enclaves, this property offers a blend of classic Cape Cod charm & refined living. Set on 40,500 sq. ft. of beautifully landscaped grounds, the home invites both quiet retreat and gracious living. Inside, rich pine floors flow throughout a lovely designed layout featuring 10 spacious rooms, including 4 bedrooms & 3.5 baths The gourmet kitchen is the heart of the home, complemented by a walk-in pantry, dining room with f/place, & multiple livings areas each enhanced with 2 additional f/places. A lovely primary bedroom en suite is matched by his/hers walk-in closets. Architectural details abound, including 2 staircases, a walkout partially finished lower level & expansion potential above the oversized 2 car garage. Perfectly positioned to enjoy the best of Chatham living, whether it's walking the iconic Chatham Loop, a short distance from the house or launching a boat from Oyster Harbor boat landing a stones throw away, for all your coastal adventures. Modern comforts include central air, whole-house generator & outdoor shower. It's more than a home-it's a lifestyle-defined by location, character, and timeless coastal elegance.

60 Harbor Hill Road, Chatham

$5,750,000
5 Beds 5 Baths 22601572 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings and thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat with tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for family and guests. A walk-out lower level expands living space with an entertainment room and full bath. Features include 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, with deep water access to Nantucket Sound. This exceptional property just off the Chatham Loop offers both privacy and a picturesque natural setting only minutes to Town.

70 Judges Way, Chatham

$699,999
1 Baths 22601404 MLS
Prime Chatham Residential Potential with R20 Zoning! This unique property offers a rare opportunity to create a standalone single-family home just moments from the vibrant heart of downtown Chatham. Prospective buyers should note that the building is currently utilized as a commercial barber shop under a 1969 variance; however, it is situated in the R20 residential zone. This provides a compelling path for conversion: by petitioning the Zoning Board of Appeals (ZBA) to lift the existing variance, a new owner could return the property to its residential roots as a charming coastal cottage or private pied-a-terre.The 600-square-foot building sits on a prominent corner lot on Route 28 with dedicated front and rear parking. It is fully equipped with town water and sewer (rated for 550 GPD), natural gas heat, and a 2020 mini-split for cooling. The interior already features a sink and laundry area, offering a head start on a residential floor plan. While any change of use from ''Personal and Household Services'' requires formal ZBA approval, the R20 zoning makes this a high-potential project for a custom home. Shown by appointment only.

1772 Main Street, Chatham

$12,999,900
4 Beds 7 Baths 22601380 MLS
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. Spanning more than 6,200 square feet across three impeccably designed levels, the residence is a study in refined elegance and thoughtful scale. Every detail has been curated for a sense of timeless sophistication while embracing the natural beauty of its surroundings. The main level unfolds with effortless grace, where a grand open-concept kitchen and great room--anchored by one of four gas fireplaces--serves as the heart of the home. A formal dining room, butler's pantry, and coffee bar create an environment equally suited for intimate gatherings and elevated entertaining. Bathed in natural light, the breakfast room offers serene views over the resort-caliber outdoor setting, where a 16' x 36' Gunite pool with integrated spa and sun shelf, is set against the tranquil backdrop of the Mitchell River. The first-floor primary suite is a private sanctuary, appointed with a a spa-quality bath featuring radiant heated floors, a soaking tub, and a glass-enclosed shower. The upper level reveals a dramatic loft retreat with fireplace, wet bar, and private deck--an ideal vantage point to take in sweeping water views. A second primary suite, equally refined, is complemented by two additional guest bedrooms and baths. Above the garage, a substantial bonus room with its own deck captures panoramic vistas of Stage Harbor and the historic Chatham Coast Guard Boathouse. This home is further distinguished by its exceptional level of finish and infrastructure, including Wolf appliances, curated fixtures, central vacuum, whole-house generator, 400-amp electrical service, and professionally landscaped grounds supported by a private irrigation well. An outdoor shower completes the effortless indoor-outdoor lifestyle. A singular offering of enduring quality and provenance--this is more than a home; it's a legacy property in one of Cape Cod's most treasured waterfront settings.

157 Bridge Street, Chatham

$4,995,000
5 Beds 5 Baths 22601118 MLS
LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen and oversized island seamlessly integrate with the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy gas fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. Ascending to the second floor, you'll discover four wonderfully proportioned bedrooms, each offering distant Atlantic Ocean views, and three stylish full baths. The primary suite is a true retreat, boasting glorious views, a spacious walk-in closet, a dressing room, and an exquisite bathroom and shower. Around the corner is the Outermost Harbor Marina, and the nearby Old Village is the gateway to the start of Chatham's Main Street.

101 Morris Island Road, Chatham

$5,850,000
5 Beds 6 Baths 22601111 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

$4,500,000
4 Beds 4 Baths 22601006 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

$1,399,000
3 Beds 2 Baths 22600988 MLS
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. Offering two levels with 2,448 sqft (1,530 sqft finished), the home has been meticulously maintained, with updates including a new roof, central A/C, outdoor shower, renovated primary bath, updated appliances, and more. The main level features a bright living room with a wood-burning fireplace and bay window, an updated kitchen with breakfast bar, and a dining area ideal for entertaining. A spacious primary suite with an updated bath, along with two guest bedrooms and a full bath, complete the level. The lower level adds flexibility with a second living area, bonus bunk room, garage, laundry, and additional storage. Outside, enjoy a lush lawn, large patio, new outdoor shower, and new walkway. With a strong 15+ year rental history, this home is equally well suited as a year-round residence, seasonal retreat, or investment property.

137 Shane Drive, Chatham

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