Chatham Homes

MLS Number 22600418

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 4,717
• Town Chatham

Set on nearly an acre in one of Chatham's most coveted enclaves, this Stage Island residence offers an extraordinary combination of refined craftsmanship and sweeping Stage Harbor views. The welcoming foyer opens to a dramatic living room with walls of glass framing the water, filling the space with natural light. A stylish kitchen with center island and dining area extends to an expansive deck, creating effortless flow between indoors and outdoors. The first floor also features a private ensuite bedroom, cozy den, and laundry area--providing flexibility for both guests and single-level living. Upstairs, three additional ensuite bedrooms include a serene primary suite with panoramic views, a spa-like bath, and spacious walk-in closet. With generous gathering areas and thoughtful details throughout, the home captures the essence of coastal luxury.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

MLS Number 22501564

• Residential
• Bedrooms 5
• Bathroom 3
• Square Feet 1,896
• Parking Spaces 10

This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and the Atlantic Ocean beyond. Over 114 feet of private beach protected by a beautiful rock revetment. Quick salt water access to ocean by boat from your own beach. A perfect spot for relaxing, entertaining under the sun or stars and creating lasting memories .This coastal property features panoramic water views, five bedrooms, three baths, and 1850+ square feet of living space to leave as you will or make it your own... A 69,000 plus square foot lot in R 40 zone would allow a guest house and a pool with town approvals in addition to the main house. A short jaunt to Main Street, Chatham Bars Inn and Wequassett, and all that Chatham has to offer....Buyers and agents should verify all information herein. This has not been independently verified and buyer should do his/her own due diligence.

Listed by John B Burke and Catherine L Stevens of William Raveis Real Estate & Home Services

MLS Number 22600447

• Residential
• Bedrooms 7
• Bathroom 3
• Square Feet 2,552
• Parking Spaces 4

Presenting a rare and extraordinary opportunity to create the ultimate in-town beach house in the heart of Chatham Village. Ideally set on 1.52 acres in one of Cape Cod's most sought-after neighborhoods, the seven-bedroom residence features a rolling lawn that gives way to a pristine, private sandy beach on Chatham Harbor, with views of North Beach and the Atlantic Ocean beyond. Showcasing original architectural details throughout, this quintessential shingle-style home is a blank canvas ready to be reimagined and deliver an inimitable lifestyle. Perfectly positioned to enjoy coastal living at its finest, days can be spent playing in the sand and soaking up breathtaking water views before strolling into the village for the evening. Combining a highly coveted setting with unsurpassed natural beauty, this exceptional property is ready to be enjoyed for generations.

Listed by Paul E Grover and Matthew de Groot of Berkshire Hathaway HomeServices Robert Paul Properties

MLS Number 22503738

• Residential
• Bedrooms 7
• Bathroom 7
• Square Feet 6,521
• Parking Spaces 10

Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views, sophisticated interiors, and seamless transitions to the outdoors. A grand 5-bedroom, 4 bath, 4,551 sf colonial home with impeccable craftsmanship & 5 fireplace features multiple sun-drenched living spaces and seamless indoor-outdoor flow. The 1,970 sf, 2 bed, 2.5 bath colonial guest house, built in 2016, is perfect for extended family & friends. Nestled along the Chatham shoreline this 2.6-acre property boasts a sparkling in-ground pool, hot tub, and beautifully integrated fire feature. Live an active lifestyle with a private tennis court, half basketball court, space for lawn games and all your summer activities. .2 miles to Hardings Beach, a premier Nantucket Sound beach. This is a once-in-a-generation opportunity to own a legacy estate on the water.

Listed by Shane K Masaschi of Compass

MLS Number 22503829

• Residential
• Bedrooms 2
• Bathroom 3
• Square Feet 1,850
• Town Chatham

Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes. Combining timeless Cape Cod charm with a vision for the future, 99 Uncle Alberts Dr is a one-of-a-kind offering on the waterfront, perfect for those seeking privacy & a truly iconic Chatham location.

Listed by Shane K Masaschi of Compass

MLS Number 22504804

• Residential
• Bedrooms 5
• Bathroom 4
• Square Feet 3,080
• Town Chatham

** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms--four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room with fireplace, first-floor bedroom currently used as a sitting room, foyer with unique herringbone brick floor, laundry room, plus finished basement. Upstairs, the primary suite offers full bath and three closets, plus two additional bedrooms with full bath. Enjoy picturesque front and back porches, mature plantings, a stone deck, a private back yard with firepit, and space for a swimming pool or tennis court. On the Chatham walking loop, just steps to downtown, Oyster Pond, and Battlefield Landing. Don't miss this exceptional opportunity!

Listed by Timothy P Bailey and John C Ricotta of John C Ricotta & Assoc.

MLS Number 22504396

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 5,300
• Town Chatham

Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway...Architecturally pleasing 4BR 6 bath shingled home will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The 5800 sf home will offer the best in new amenities with a nod to the shingled coastal cottage estates of times past.. The open interior has both a welcoming front porch as well as a screened porch. The magic continues with high ceilings, centrally located living room with fireplace that opens to well designed kitchen with center island, breakfast room, pantry and adjacent dining room. A robust primary ensuite, private den and three additional quest bedrooms grace the second floor. The lower level has two additional rooms and a full bath. Media room, playroom, gym? you decide. Two car detached garage with additional full bath and potential for a swimming pool. Early summer 2026 occupancy.

Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

MLS Number 22504680

• Residential
• Bedrooms 3
• Bathroom 5
• Square Feet 4,393
• Parking Spaces 2

One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes and extras at this stage of construction with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyer. Incorporating expansive open living space you will enjoy entertaining friends and family here. Some of the features are three ensuite bedrooms, a magnificent cooks kitchen with butlers pantry and a custom inground pool among other things you come to expect from this creative builder. Do not miss this opportunity to make this very special home your own.

Listed by Ward H Brown,III of William Raveis Real Estate & Home Services

MLS Number 22504678

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 3,713
• Parking Spaces 5

One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes at this stage with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyers. Incorporating expansive open living space you will enjoy entertaining family and friends here. Some of the features are a three car garage, four ensuite bedrooms, a magnificent cooks kitchen with pantry and a custom inground pool among other things you would expect from this creative builder. Do not miss this opportunity to make this very special home your own.

Listed by Ward H Brown,III of William Raveis Real Estate & Home Services

MLS Number 22502029

• Residential
• Bedrooms 3
• Bathroom 5
• Square Feet 3,640
• Town Chatham

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island w/walnut top offers space for casual dining and flows to the dining area. The nearby butler's pantry enjoys a Subzero beverage fridge. The inviting living area w/gas fireplace opens to a 3-season porch which extends your living space and is adjacent to the deck that overlooks a pristine conservation area. The 1st story primary suite boasts an ensuite bath w/radiant floor heat & walk-in closet. The 2nd story features 2 en-suite bedrooms, family room & home office. The finished lower-level w/9'' ceilings, a full bath, & 725 sq ft of living space. Other features include custom woodwork, 1st floor laundry, irrigation by well, dual fuel gas hydro air hvac w/heat pump to maximize efficiency & 1-car garage. With its prime location, you can easily walk to town, a nearby beach and boat mooring.

Listed by Shane K Masaschi of Compass

MLS Number 22505703

• Residential
• Bedrooms 3
• Bathroom 3
• Square Feet 2,004
• Parking Spaces 3

Professional photos coming soon! Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living. This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted setting within a friendly association that features an association dock, complete with kayak storage and a picnic area-ideal for effortless days on the water. The home is enhanced by EV charging station and owned solar, offering exceptional energy efficiency and savings. Thoughtfully designed, light-filled, and meticulously cared for, it is truly a delight to show. Come experience the charm, serenity, and coastal lifestyle this Hardings Beach Hills gem has to offer. Abutting property, 78 Indian Trail, also available for sale at $2,800,000.

Listed by Judith L Smith of John C Ricotta & Assoc.

MLS Number 22505704

• Residential
• Bedrooms 3
• Bathroom 2
• Square Feet 1,160
• Parking Spaces 4

Professional photos coming soon!Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in beautiful water views and unforgettable sunsets, with private stairs leading down to the water's edge of Bucks Creek for easy access and serene enjoyment. Inside, the home is a pleasure to show, highlighted by a wonderful sunroom that captures the light and scenery year-round. A rare opportunity to enjoy Chatham living at its best. An abutting property, 92 Indian Trail, is available for $3,200,000.

Listed by Judith L Smith of John C Ricotta & Assoc.

MLS Number 22505455

• Residential
• Bedrooms 3
• Bathroom 4
• Square Feet 3,090
• Parking Spaces 6

Offered fully furnished, this light-filled contemporary Cape in North Chatham blends coastal elegance with casual sophistication. The main level features a welcoming den, an inviting living room with a fireplace, and a stylish kitchen and dining area that open to a sunny deck, ideal for seamless indoor-outdoor living. The serene first floor primary suite offers comfort and privacy. Upstairs, two additional bedrooms, a full bath, and a family room with a second-level deck provide ample space for guests or a home office. The walk-out lower level offers flexible living or recreation space. Outside, discover a private fenced in backyard oasis complete with a heated in-ground pool, hot tub, stone patio, and lush landscaping--perfect for summer entertaining or quiet relaxation. Situated on nearly half an acre, this exceptional property is moments from Ryders Cove Marina, Crows Pond, Eastward Ho!, and the vibrant shops and restaurants of downtown Chatham. The home has a strong rental history. Furniture Exclusions: Painted Dresser in Living Room, Table in Upstairs Hallway, We Need a Bigger Boat sign

Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

MLS Number 22501963

• Residential
• Bedrooms 3
• Bathroom 5
• Square Feet 1,834
• Parking Spaces 2

Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to the center of Chatham Village sits this exceptional 3 bedroom 4 bath custom Farmhouse with inviting front porch built in 2018. Hardwood floors thruout and, formal dining area, custom kitchen along with an office for those working remotely. Home has central a/c and a gas stove in the Livingroom. The lower level contains an in law suite with full bath and kitchenette less a stove and a laundry room. Furniture negotiable.

Listed by Ward H Brown,III of William Raveis Real Estate & Home Services

MLS Number 22403062

• Residential
• Bathroom 1
• Square Feet 2,586
• Town Chatham

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

Listed by Judith L Smith of John C Ricotta & Assoc.