Refine Search
Map
Sort by
$5,805,000
7 Beds ⋅ 4 Baths ⋅ 73421848 MLS
Perched high above Oyster Pond, this generational estate—first known as “The Beach Plum House” and later as “Adsamore”—is one of Chatham’s rarest offerings. Set on a .93-acre parcel with expansive frontage, it captures sweeping views of town and Oyster Pond, a lifestyle both connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, it has been preserved and expanded over generations while modernized for gatherings. Seven bedrooms include a first-floor primary suite, while a Good Morning staircase with a hand-painted Chatham mural leads to additional bedrooms. Historic character endures throughout: the celebrated wood room with elements from the Plymouth Cordage Co. ropewalk (c.1824), hand-hewn beams, herringbone brick floors, central hearths, and built-ins. Outside, brick patios, sycamore trees, granite steps, and rock walls frame lawns rolling to the water’s edge, where a private catwalk and moorings await. A legacy property, ready for its next steward.

58 Oyster Bluff, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$1,385,000
4 Beds ⋅ 3 Baths ⋅ 73422354 MLS
Just steps from deeded rights to fishing kayaking swimming kayaking what a fantastic location

114 Bucks Creek, Chatham

Listing courtesy of Listing Agent: Adeline Harrington from Listing Office: .
$1,495,000
3 Beds ⋅ 2 Baths ⋅ 73436434 MLS
Idyllic Seaside Cottage is just steps to popular Ridgevale Beach! Enchantment begins with the exquisite and stunning array of Hydrangeas and seasonal plantings making it as inviting on the outside as it is on the inside. Whether you are sipping coffee on the deck or just simply soaking in the ocean breezes, this Coastal year round Cottage is what living in Chatham is all about. Many recent updates include new Central AC, Heat Pump, Gutters, New Asphalt roof, new deck, new quartz countertops and marble bath vanity, refinished wood floors, new appliances, custom interior Cafe shutters, electrical updates, painted interior and exterior, and so much more...This sweet home is the perfect blend of comfort and Coastal charm. Don't miss this rare Seaside gem! Bonus: Excellent Rental history wit impeccable ratings!

291 Ridgevale Rd, Chatham

Listing courtesy of Listing Agent: Janet Nowak from Listing Office: Craigville Realty, Inc..
$3,350,000
4 Beds ⋅ 4 Baths ⋅ 73415038 MLS
Rarely available in Chatham’s coveted Harbor Coves, just steps from the private Association beach, this 4BR, 3.5BA residence has been completely reimagined top to bottom, inside and out. A sweeping circular drive welcomes you home to sunlit vaulted living spaces with high-end finishes that sparkle at every turn. The brand new gourmet kitchen with oversized island flows into a stunning shiplap-ceiling family room with wet bar. Enjoy seamless indoor-outdoor living with a spacious deck and new patio, balcony and gas fire pit overlooking private grounds. The vaulted primary suite features a spa-like bath and dual closets on the 1st floor. Upgrades include new gas fireplace, hardwoods, custom tile, fresh paint, roof, siding, windows, gutters, hardscape, landscape, outdoor shower, irrigation, security system, gas HVAC, and hot water heater. Three-car garage. A turnkey coastal retreat in one of Chatham’s most exclusive neighborhoods—offering the perfect blend of luxury, privacy, and location!

174 Seapine Road, Chatham

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: .
$4,600,000
5 Beds ⋅ 5 Baths ⋅ 73391890 MLS
Welcome to " Two Stars" this meticulously crafted residence located in coveted North Chatham. This beautiful sanctuary offers an harmonious blend of luxury & comfort. Nestled on a lush acre with water views of Chatham harbor, this custom built masterpiece by master/builder owner invites you to experience refined living with every thoughtful detail. Spanning 4200sq. ft of sophisticated space, this home boasts 9 gracious well appointed rooms that include private primary 1st fl suite, 3 full and 2 half baths, and 3 further bedrooms, a charming library & a 1 st Floor cathedral ceiling Great room /studio with skylights & French doors that could serve as the 5th bedroom. The interior is a testament to craftsmanship with custom cherry cabinets and doors, inlaid wooden medallions, and array of bespoke built-ins. The exterior is equally impressive with expertly landscaped & fenced back yard offering room for a pool. With nearby Scatteree &Cow Yard beaches, a timeless lifestyle awaits.

785 Old Harbor Rd, Chatham

Listing courtesy of Listing Agent: Phyllis Power from Listing Office: Kinlin Grover Compass.
$895,000
2 Beds ⋅ 2 Baths ⋅ 73440834 MLS
Located in Chatham’s desirable Riverbay, this 2-bedroom, 2-bath, 2,097 sq. ft. home rests on a private .91-acre irrigated lot with mature plantings. In solid condition, the home is ready for cosmetic updates to reflect your style. The kitchen with laundry opens to a fireplaced family room, while the adjoining dining room flows to a bright living room with wood floors, a second fireplace, bay window, and window seat overlooking the tranquil yard. A sunroom with abundant light adds versatile living space and easy access to the outdoors. The ensuite primary bedroom with wood floors is complemented by a second bedroom and hall bath. An attached garage with direct entry enhances convenience. With thoughtful improvements, this property could be transformed into a perfect summer retreat or comfortable year-round residence. Minutes to Jacknife Cove, Riverbay ponds, and Chatham’s amenities.

558 Riverview, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$2,950,000
4 Beds ⋅ 5 Baths ⋅ 73441716 MLS
Wake up to shimmering views of Nantucket Sound from your luxurious family compound, just steps from Cockle Cove Beach and a sandy stretch off Chatharbor Lane. This rare offering features a newly built main house with three ensuite bedrooms and a separate, gut-renovated one-bedroom cottage for all of your overflow needs. The sundrenched main home boasts spacious, open-concept first-floor living that spills perfectly onto an inviting deck and screened porch; a first-floor primary suite with a spa-inspired bathroom; and a finished, walk out basement with 9 ft ceilings, a gym, movie room and rec room. After a movie & a game of pool, relax in your hot tub under the stars to recap your perfect day. Down the way, you'll be delighted with your coastal inspired cottage with a 30-foot deck boasting amazing views of the Sound and Cockle Cove Creek. Make lasting memories here yourself or take advantage of well-established rental income--this exceptional offering gives you the best of both worlds.

314 Cockle Cove Rd, Chatham

Listing courtesy of Listing Agent: Christa Zevitas from Listing Office: .
$1,785,000
4 Beds ⋅ 3 Baths ⋅ 73439936 MLS
Nestled on a quiet street in the heart of downtown Chatham, 24 Shattuck Place is a beautifully maintained 4-bedroom, 2.5-bath home offered fully furnished and turnkey. The thoughtful floor plan includes a first-floor primary suite, an updated kitchen, central air, and a new hot water heater and gas furnace. 3 additional bedrooms and full bath on the second level offer flexibility and privacy from the main level. Step outside to enjoy a private patio and outdoor shower—perfect for summer living. From this ideal in-town location, you can walk to Oyster Pond, Lighthouse Beach, Chase Park, and all the shops and restaurants of Main Street. Whether you’re seeking a year-round residence, summer retreat, or investment property, this home is ready for you to move right in and start enjoying the best of Chatham living.

24 Shattuck Pl, Chatham

Listing courtesy of Listing Agent: The Charles King Group from Listing Office: Real Broker MA, LLC.
$6,995,000
5 Beds ⋅ 7 Baths ⋅ 73348335 MLS
Experience luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship. Designed for both comfort and entertaining, it offers five spacious bedrooms, each with an en suite bathroom, plus two half baths. Two elegant living rooms and a formal dining room create the perfect setting for memorable gatherings. The gourmet kitchen features high-end appliances, custom cabinetry, and exquisite finishes. A dedicated home office and two laundry areas add convenience. Step outside to your private waterfront retreat with a beautiful pool and direct deep-water access to the Oyster River, perfect for boating. This rare opportunity to own a brand-new luxury home in one of Chatham’s most coveted locations offers refined elegance and serene coastal living.

13 Captain Knowles Way, Chatham

Listing courtesy of Listing Agent: Mina O'Keefe from Listing Office: Gibson Sotheby's International Realty.
$1,700,000
3 Beds ⋅ 2 Baths ⋅ 73426705 MLS
Welcome to 44 Emery Lane is North Chatham! This welcoming sunny 3 bedroom cape on .7 level acres is sure to please, especially given its excellent location. Walk to historic Old Harbor road and stop by Cow Yard beach to get your feet wet, or saunter over to Scatteree point and take a few casts....This is what living in Chatham is about. Hardwood floors greet you along with a wood burning fireplace in the living room. A large dining room opens to a family room/sunroom. The kitchen is spacious. the first floor includes a first floor bedroom and full bath. The second floor is made up of 2 oversized bedrooms and a large shared bath. The garage is huge and includes a loft that would make an ideal finished space in the future. Title 5 has passed. Lot's of room for a pool!

44 Emery, Chatham

Listing courtesy of Listing Agent: Kathleen Phelan from Listing Office: Compass.
$1,475,000
3 Beds ⋅ 4 Baths ⋅ 73374547 MLS
Just 8/10 of a mile to Jackknife Point BeachThis beautifully appointed Chatham retreat offers the perfect blend of comfort, style, and solar efficiency. A charming farmer’s porch welcomes you into a light-filled home with high ceilings, an open layout, and a skylit kitchen with granite counters, stainless steel appliances, and a large island. The living room features a cozy gas fireplace, and the first-floor primary suite provides comfort and convenience. A flexible space on the main level offers potential for a home office or family room. Upstairs, two spacious bedrooms share a Jack and Jill bath. The walk-out lower level offers expansion potential, while first-floor laundry, solar panels, and a peaceful wooded backdrop add to the appeal. Enjoy coffee on the front porch or unwind on the back deck after a day at the beach—this is Chatham living at its best.

355 Training Field Road, Chatham

Listing courtesy of Listing Agent: Margaret McDonald from Listing Office: Mathieu Newton Sotheby's International Realty.
$9,650,000
5 Beds ⋅ 8 Baths ⋅ 73421738 MLS
Wake up to captivating and shimmering water views from nearly every room in this stunning Little Mill Pond home. Completely rebuilt just a few years ago with exceptional craftsmanship, it blends custom trim, cabinetry & timeless design. This residence blends coastal elegance with modern convenience, all within walking distance to the charming shops and dining of downtown Chatham. Inside, you'll find exquisite custom finishes at every turn—detailed trim work, bespoke cabinetry, and thoughtfully curated personal touches that make the home truly one-of-a-kind. The airy floor plan is enhanced by walls of glass and multiple balconies and decks that invite the outdoors in. The kitchen is a chef's dream, seamlessly flowing into inviting living spaces that are perfect for entertaining. The finished lower level features a sophisticated entertainment bar and flexible space for gatherings. Practical luxuries include a full-house generator, 4 fireplaces, and deep water access via a private catwalk

53 Gristmill, Chatham

Listing courtesy of Listing Agent: Sharon Mabile from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 73427284 MLS
Just a short stroll from Forest Road Beach, this classic Chatham cape captures the essence of coastal living. Wake to sea breezes and glimpses of the ocean from your front lawn, spend the day swimming or beachcombing, then return to a sun-drenched living room where a traditional hearth and built-ins create timeless New England charm. With four bedrooms, three of them en suite, everyone has their own retreat. The guest suite, complete with sitting area, kitchenette, and two private entrances, offers ultimate flexibility for guests or extended family. The galley kitchen and breakfast room overlook a spacious deck and half-acre of lush irrigated lawn and flowers. Rinse off in the outdoor shower before settling in for the night. A year-round haven, vacation escape, or prime rental, this home invites you to slow down and savor Cape Cod life. Buyers and buyer agents to verify all facts therein

216 Forest Beach Rd, Chatham

Listing courtesy of Listing Agent: Maureen Green from Listing Office: Kinlin Grover Compass.
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 73435858 MLS
Exceptional views of Nantucket Sound and Deeded rights to a private beach just steps away make this fully renovated three bedroom home truly exceptional. Styled with a coastal aesthetic, the interior features designer finishes that evoke the relaxed elegance of oceanside living. Step outside to enjoy an expansive outdoor living area, complete with a natural gas fire table, an outdoor shower and space for sunbathing ~ all surrounded by lush, professionally landscaped grounds. Don't miss this rare opportunity to own a move-in-ready home that offers luxury, lifestyle, and location all in one.

34 Sea Mist Ln Unit 34, Chatham

Listing courtesy of Listing Agent: Rick Smith from Listing Office: Gibson Sotheby's International Realty.
$2,450,000
3 Beds ⋅ 4 Baths ⋅ 73429729 MLS
Catch the breezes atop Great Hill in this centrally located classic Cape with deeded rights to Lovers Lake. Updated with flair, this 8-room home offers 3275 sq ft. of living space & is perfectly nestled on a professionally landscaped lot. The home has a great floor plan that will surprise and delight you with unique & pizazz-y features. Whether year-round, or summer living, this beautifully designed floor plan accommodates any lifestyle. The great room, with a gas FP is an open plan with a vaulted ceiling. Gatherings are easy and flow well into adjacent spaces, including the formal DR, a good-sized butler's pantry, LR, and powder room. Also on the 1st FL is the primary bedroom and bath. Two different sets of stairs lead to 3 upstairs rooms and 2 additional bathrooms for flexible living space and work-from-home options.. Attached 2-car garage with mini split, OS, and irrigation. Many fine improvements make this a charming, bespoke home move-in ready!

252 North Skyline Dr, Chatham

Listing courtesy of Listing Agent: The Nickerson Power Group from Listing Office: Compass.
$674,000
2 Beds ⋅ 1 Baths ⋅ 73429710 MLS
Don’t miss this lovely 2 Bedroom, 1 Bath Cape-style ranch in well-groomed residential neighborhood near town. As part of Great Hills Estates, this property has deeded rights to Lover’s Lake including water access, picnic & BBQ area, and kayak racks. Enjoy sidewalk access to Town, easy proximity to the Chatham Bike Path, and a location just 2 miles to Hardings Beach. Inside, the main level offers 2 bedrooms, a full bath, living room with bay window and fireplace, and small kitchen with adjacent dining. There is also a finished room in the walk-out lower level. Amenities include natural gas heat, 1-car garage, yard, outside shower, and a good-sized corner lot. Cosmetic updates would further enhance this home that already has nice curb appeal. Possible expansion opportunities exist for a creative Buyer looking to create their Chatham dream home. 38 Andover Drive has the location and potential - it just needs a Buyer who will make it shine!

38 Andover Dr, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$3,550,000
4 Beds ⋅ 4 Baths ⋅ 73399127 MLS
This Chatham Beach House is calling...hope you answer.... Picture perfect Cape Cod style home with divine views over Nantucket Sound offers the idyllic Chatham beach lifestyle you have been dreaming of.....Steps to the private association beach of Harding's Shores for uncrowded enjoyment and warm water swimming. Classic 4BR 4 bath Cape home with two large decks for al fresco dining or morning coffee while watching the tides change. Built in 2004 , this home offers so much more on the interior. Open floor plan includes a bright kitchen with water views and granite counter tops, ,dining area, a fireplaced living room, a second intimate media room/den , a lower level play area and four upstairs bedrooms. The primary offers privacy and a walk in closet, full bath and access to the second floor deck. An additional bedroom also has it's own bath . Harding's Beach offers a great hiking travel towards Stage Harbor Lighthouse and good Striper fishing from the beach.

17 Bucks Ln, Chatham

Listing courtesy of Listing Agent: Lori Fanning Smith from Listing Office: Compass.
$3,675,000
4 Beds ⋅ 6 Baths ⋅ 73268296 MLS
NEW CONSTRUCTION Another magnificent home by Sears Point Residential is now move-in ready. This 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape is just steps from your deeded boat slip in the Oyster River Hills private neighborhood marina. The heart of the home is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows seamlessly from the living room to the dining room and a den/office and features stunning hickory floors, high ceilings, and custom woodwork throughout. Each bedroom has an en-suite bathroom, with primary bedrooms on both floors, and both feature luxurious soaking tubs. The finished lower level with 9' ceilings and deep window wells provides 1,587 sq. ft. of living space and includes a custom bar, wine storage, a family room with a gas fireplace, a home gym, a den/study, and a half bath. The well-water irrigated yard is designed for outdoor living with ample room to add a pool. Whole house generator

45 Meadow View Rd South, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.
$898,000
4 Beds ⋅ 2 Baths ⋅ 73433213 MLS
Cape Cod living made easy in this beautifully updated 4-bedroom, 2-bathroom Cape nestled in the desirable Great Hill Estates neighborhood, less than a mile from downtown Chatham. Thoughtfully renovated throughout, this home blends modern updates with timeless Cape charm. The inviting floor plan features a bright living area, a well-appointed kitchen with quality finishes, and four comfortable bedrooms offering plenty of space for family and guests. A standout bonus is the sunroom, filled with natural light and perfect for relaxing or entertaining year-round. Enjoy the best of Cape Cod living with deeded access to picturesque Lover’s Lake, where you can launch a kayak, paddleboard, or simply enjoy the peaceful surroundings. Set in a prime location close to shops, dining, and Chatham’s vibrant Main Street, this property is ideal as a year-round home, vacation retreat, or investment opportunity.

306 Old Queen Anne Rd, Chatham

Listing courtesy of Listing Agent: Sharon Mabile from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$2,325,000
3 Beds ⋅ 4 Baths ⋅ 73431929 MLS
Built in 2014, this beautifully designed home offers 3 bedrooms, 4 full baths, and over 3,400 sq. ft. of living space, including a finished basement and a bonus room above the detached garage. Hardwood floors flow throughout the open layout, where you'll find a chef ready kitchen, sun-filled living room with coffered ceilings and gas fireplace. The first floor is completed by a full bath, laundry room & den. Upstairs, 3 bedrooms including a primary ensuite with a walk-in closet. The finished basement expands your options with a living room, sleeping area, full bath, and wet bar—perfect for guests. Outdoor living shines with a welcoming front porch and a back patio featuring a natural gas firepit. Just around the corner, Barn Hill Landing offers easy access to the water for boating or kayaking. A perfect blend of comfort, style, and Cape Cod living.

94 Ocean Port Ln, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.
$2,400,000
4 Beds ⋅ 5 Baths ⋅ 73332508 MLS
''On Pink Wink Pond'' embodies the essence of Cape Cod. A startling entrance of Belgian blocks with carriage lighted and stone pillars greets the visitor. Ascending the farmers porch and upon entry, an illuminated tile mural of Pink Wink Pond boasts the home's attention to artistic detail. The two-story windowed great room is surrounded by crystal blue shiplap and offers a gas fireplace. Sub-Zero and Wolf appliances are features of the chef's kitchen. A main floor primary suite boasts marble steam shower and soaking tub. Half bath with laundry, ample closets, and media room tops off the main level. Sliding doors lead to a wraparound deck. Perched next to the pond, ''The Nest'' provides the perfect spot to enjoy a quiet moment. The second floor provides luxury comfort with two en-suite bedrooms, one with a balcony and home office, plus private guest quarters. A whole house generator, radiant heated floors, and on-demand water heater completes this home. This Estate is pure perfection.

290 Old Comers Rd, Chatham

Listing courtesy of Listing Agent: Catherine Baran from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$1,195,000
3 Beds ⋅ 2 Baths ⋅ 73415633 MLS
Elevated for privacy, this single-level home features a bright living room with a wood-burning fireplace, a dining area opening to a Brazilian hardwood deck, and a sleek kitchen with upgraded appliances and nearby laundry. The primary suite includes an ensuite bath, while two additional bedrooms include one with built-ins and a window seat—ideal as an office. The expansive, private yard offers excellent pool potential, complemented by an outdoor shower, generator, and a one-car garage. An unfinished lower level offers future expansion opportunity. Nestled across the street from two scenic ponds, the home is located in Chatham’s sought-after Riverbay Estates, known for its tranquil tree-lined streets, community vibe, and driving proximity to Chatham Village, East Harwich, Pleasant Bay swimming, and much more.

56 Riverview Drive, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$2,500,000
4 Beds ⋅ 4 Baths ⋅ 73350536 MLS
Nestled on just over an acre of meticulously landscaped grounds near the Oyster River, this 4-bedroom, 3.5-bath home offers a rare opportunity to create your dream space. With deeded access to a shared boathouse, it provides a serene and sophisticated lifestyle. Built in 1987 and well cared for, the home retains its classic charm and is ready for your updates. Designed for effortless entertaining, it features a seamless flow with two sets of French doors opening to an oversized deck. The sunlit living room boasts vaulted ceilings, a fireplace, and built-in bookcases, while the study offers additional built-ins for a refined touch. The first-floor primary suite includes two walk-in closets, and the second-floor ensuite features a charming window seat with custom built-ins. A rare find in an unbeatable location.

106 Stage Neck Rd, Chatham

Listing courtesy of Listing Agent: Jen Graham from Listing Office: Christie's International Real Estate Atlantic Brokerage.
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 73363447 MLS
Discover luxury & comfort in this stunning Riverbay home nestled with beautiful landscaping on Riverview Drive. This meticulously renovated 7 room ranch offers 2340 Sq. ft of elegant living space, featuring 3 spacious bedrooms, 2.5 luxurious tiled baths with double vanities. As you step inside, the inviting foyer introduces you to the warmth of a formal living room with fireplace, open plan to dining room perfect for gatherings. The heart of the home is the gorgeous sunny white Omega kitchen, SS appliances, vaulted skylight, good storage cabinets, quartz countertops, seamlessly blending style and functionality. Rich hardwood floors flow throughout, complemented by marble and tile accents. The 1/2 bath, laundry/mud room has door to spacious deck on south. The adjacent family room is cozy with a gas fireplace & slider to the deck. There is a home office for remote working & an oversize garden shed big enough to store kayaks .Generator, AC, OS, irrigation, Pella windows, WOW!

307 Riverview Dr, Chatham

Listing courtesy of Listing Agent: Phyllis Power from Listing Office: Compass.
$846,000
3 Beds ⋅ 2 Baths ⋅ 73432255 MLS
OPEN HOUSE CANCELLED-Don't miss this 3-bedroom, 2-bath, lovingly cared for home offering 1,536 sq. ft. of inviting living space including a large open great room and living room with fireplace. Beautiful hardwood floors run throughout. Ideally located in a quiet neighborhood, the house is situated on the bike path and a short distance to White Pond for kayaking and swimming . Relax on the welcoming front porch overlooking a quiet street, or retreat to the private back deck complete with an outdoor shower—perfect after a day at the beach. Already connected to town sewer = this home is ideal as a year-round residence, summer getaway, or starter home. Enjoy all the benefits of Chatham living located near downtown center shops and dining, beaches and ballpark.

29 Wilfred Rd, Chatham

Listing courtesy of Listing Agent: The Bohman Hartung Group from Listing Office: Gibson Sotheby's International Realty.
$1,315,000
3 Beds ⋅ 3 Baths ⋅ 73339493 MLS
Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates. Step into the spacious great room with exposed beams and a cozy wood-burning fireplace, perfect for relaxing after a day by the water. The adjoining kitchen and dining area provide seamless access to the waterside deck—ideal for morning coffee or sunset gatherings. All bedrooms are conveniently located on the main level. The newly remodeled lower level has a game room and walk-in laundry room with a sink, and direct outdoor access. Inquire about the many recent upgrades. Located near Jackknife Beach.

552 Orleans Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$855,000
3 Beds ⋅ 2 Baths ⋅ 73363317 MLS
Three bedroom ranch house with two car garage in desirable Riverbay Estates. All bedrooms on the first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area...Brokers and buyers are encouraged to verify all information herein....

144 Lakeview Avenue, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.
$955,000
2 Beds ⋅ 2 Baths ⋅ 73410964 MLS
Welcome to 67 A Leonard Way, a charming ranch-style 2-bedroom home tucked away on a quiet street just minutes from downtown Chatham. Inside you'll find a beautifully renovated kitchen with granite countertops, stainless steel appliances and custom cabinetry. The open living and dining areas feature a fireplace, built-in shelving, and hardwood floors, creating a warm and inviting atmosphere. With both bedrooms on the main floor, one en-suite, this home offers easy one-floor living. Step outside to a private deck w/pergola, surrounded by mature plantings, ideal for relaxing, entertaining, or simply enjoying the Cape Cod lifestyle. Features a one-car garage, first story washer & dryer, outdoor shower, 4-season sunroom w/soaring ceiling, office & walk-out lower level for future potential expansion. Located .5 mi from Jackknife Beach and 1.5 miles from the bike path. This hidden gem offers the perfect blend of comfort, privacy, and convenience.

67 A Leonard Way, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$995,000
3 Beds ⋅ 2 Baths ⋅ 73422565 MLS
Experience classic Cape Cod living in this inviting 3-bedroom, 2-bath Cape, just minutes from Ridgevale Beach, known for its soft sand, gentle surf, and calm waters—perfect for swimming, sunbathing, and relaxing summer days. Set on a generous .35-acre lot, the home features a private backyard ideal for outdoor entertaining or quiet evenings. Inside, the bright and welcoming layout includes a first-floor office and a living room centered around a cozy wood-burning fireplace—perfect for curling up on cooler Cape nights. Efficient gas heat keeps the home comfortable year-round. Outside, the existing outdoor shower is ideal for rinsing off after a day at the beach. With its prime location and versatile spaces, this home offers excellent rental potential while providing an idyllic year-round residence or summer retreat that captures the true charm of Cape Cod.

56 Chatham Crest Dr, Chatham

Listing courtesy of Listing Agent: Natalia Weiner from Listing Office: Gibson Sotheby's International Realty.
$2,025,000
4 Beds ⋅ 5 Baths ⋅ 73389277 MLS
Stunning magazine-worthy home tucked privately off Main Street offers resort-style living with an unbeatable location. Designed for comfort and entertaining, it features an open floor plan, shiplap walls, dining room with wet bar, and a half bath leading to a backyard oasis. Enjoy a heated inground pool, spacious deck, fire pit, outdoor shower, and TV—just steps from the Cape Cod Rail Trail. The main level includes a primary suite with pool access, gas fireplace living room, cozy den, and chef’s kitchen with island. Upstairs boasts two bedrooms, a private den, full bath, and a second primary suite. The walkout lower level offers polished cement floors, sleek wet bar, full bath, and Murphy bed.

2016 Main St, Chatham

Listing courtesy of Listing Agent: Daneen Law from Listing Office: Gibson Sotheby's International Realty.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.