Chatham MA Waterfront Homes For Sale

MLS Number 22304409

• Residential
• Bedrooms 8
• Bathroom 5
• Square Feet 4,413

Sitting on 1.74 acres, this is a truly unique and meticulously maintained Chatham compound that offers a variety of possibilities. Whether you're looking for an investment property, a retirement home, a second home, or the potential for expansion, this property has it all. The main home features 4 bedrooms and 4.5 bathrooms. Two of the bedrooms are recently renovated first -floor primary and the remaining two bedrooms are located on the 2nd floor and share a full bathroom. The kitchen is fully equipped and opens up to a large patio fitted with an awning. One of the highlights of this property is the unique Pilot House with its circular design and window lined walls. From here, you can enjoy breathtaking views of the sprawling lawn and Black Pond. In addition to the main house, there is a charming guest cottage located next door which features 3 bedrooms and a recently renovated full bath, sitting area and updated kitchen. Adjacent to both the cottage and main house is a carriage house with additional living space. Ideally situated close to both town and the Atlantic, this property is conveniently close to various activities and attractions, including the Chatham Fish Pier, Chatham A's games, pickleball courts, Seaside Links golf course, and swimming spots. Additionally Downtown Chatham with all it has to offer is just moments away: fine & casual dining, galleries, shops and the beach are within easy reach. Overall, this Chatham pond-front compound is a highly desirable property that combines versatility & beauty in a prime Chatham location. See attached for amenities, improvements and rental history.

Listed by Kimberly A Robbins of Compass Massachusetts,LLC

MLS Number 22303217

• Residential
• Bedrooms 2
• Bathroom 2
• Square Feet 2,214

Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom, two bath waterfront home that feels like a private sanctuary exuding a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining area are view-filled and adjoin a sunroom with a wood burning fireplace, walls of windows and access to a patio. The kitchen has all the amenities as well as a sitting area that opens to a patio with a firepit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat, but can also provide an exceptional palate to create a custom compound or family property for generations to come.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

MLS Number 22302289

• Residential
• Bedrooms 5
• Bathroom 5
• Square Feet 4,000
• Parking Spaces 8

A captivating coastal gem, nestled on the crest of Stage Island and surrounded by the scenic waters of Nantucket Sound, this picturesque setting offers a serene and idyllic backdrop for nature enthusiasts and beachgoers alike. This one of a kind private property provides a tranquil escape from the bustling mainland, making it a cherished destination for those seeking peace and natural beauty with its unspoiled landscapes, yet not far from downtown Chatham. Some of the best views of Stage Harbor and Nantucket Sound beyond, this is simply a remarkable spot. On a double lot this home was completely renovated in 2015 by Steven Nickerson and outfitted with all the modern amenities one could dream of. A true chef's kitchen, custom cabinetry throughout, hurricane rated windows, radiant heated floors, wireless control technology, Sonos, full house generator, and more. What more could you ask for...

Listed by Team Guthrie - Mabile of Berkshire Hathaway HomeServices Robert Paul Properties

MLS Number 22302262

• Residential
• Bedrooms 5
• Bathroom 8
• Square Feet 5,519
• Parking Spaces 5

This exceptional 5 bedroom coastal retreat & boater's delight offers the best of waterfront living; complete with a private deep water dock on Ryder's Cove! Beautifully constructed by Eastward Homes, the home is nestled in a private cul-de-sac and positioned to provide stunning water views from nearly every room. Multiple living spaces inside and out, elegant first-floor primary suite, and 4 additional en-suite bedrooms. An expansive great room encompasses the living room, dining area, and gourmet kitchen, and leads to a water view bluestone patio. The finely-finished walk-out lower level offers a variety of uses and includes a full bath. Amenities include Hardwood floors, Central A/C, generator, 2 laundry rooms, irrigation, outside shower, on-demand hot water and much more to add to your ease of living. This picturesque North Chatham neighborhood is just 10 minutes to Town; with easy access to fine restaurants, shopping, beaches & surrounding towns. Ryder's Cove is a protected saltwater inlet that leads out to Pleasant Bay and the Atlantic ocean. 21 Captains Cove offers exclusive luxe living and phenomenal location for a premiere Chatham waterfront lifestyle!

Listed by Shane K Masaschi and Lori Jurkowski of Kinlin Grover Compass

MLS Number 22300106

• Residential
• Bedrooms 8
• Bathroom 6
• Square Feet 4,859
• Parking Spaces 15

Magnificent eight bedroom mansion from days gone by designed by Architect Edward Sears Read. Perched on a hill overlooking Chatham Harbor, North Beach, and the Atlantic Ocean beyond. Almost 300 feet of sandy private beach described by an article on CNN as ''one of the top 9 secret beaches in NORTH AMERICA''. Three acres of land has room for expansion, a guest house, a pool, and/or a tennis court with town approvals... A true forever, family compound within an easy walk to downtown Chatham or Chatham Bars Inn. Must see the whole property, inside and out, to fully appreciate the surroundings, the privacy of the three acres, the 300 feet of beach, the eight bedrooms, the six fireplaces, and the miles of views to the north, south, and east. And what a spectacular, one of a kind property owned by the same family since the 1940's. Opinion of some people in town is that this is the nicest property in Chatham......You decide......

Listed by John B Burke and Ward H Brown,III of William Raveis Real Estate & Home Services

MLS Number 22205347

• Residential
• Bedrooms 6
• Bathroom 5
• Square Feet 2,919

Perfectly sited on 1.4 acres directly on Oyster Pond River, this spectacular waterfront six bedroom property overlooks one of Chatham's most coveted vistas of the iconic Stage Harbor Lighthouse. From every vantage point, there are sweeping views of the waterfront with beautiful sunsets, swimming, clamming and relaxing at the beach right outside your door. Built in 1938, this property has been occupied by the same family for 70 years and opens the possibility to start a new family legacy in an unmatchable setting. Renovate or rebuild - the home is outside the flood zone. The current residence has a classic old fashion Cape Cod charm with some updates. This is a very special location with easy access to both the Atlantic Ocean and Nantucket Sound.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

MLS Number 22204503

• Residential
• Bedrooms 5
• Bathroom 3
• Square Feet 2,514
• Parking Spaces 5

Your very own paradise in Chatham in exclusive Eastward Point Assoc. 180 degrees of beautiful waterfront views. Sandy beach on Pleasant Bay and association dock on Crows Pond. This 5 bedroom 3 bath home is positioned beautifully on the lot and takes in all the views from Pleasant Bay, Chatham Harbor and Bassing Harbor with boating access to all as well as Ryder's Cove Marina and out to the Atlantic. Primary bedroom on the first & second floor. Whole house generator. Make an appointment to see this fabulous property designed and built by the well renowned Horace F. Reynolds.

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

MLS Number 22200926

• Residential
• Bedrooms 7
• Bathroom 6
• Square Feet 7,200
• Parking Spaces 20

One of the finest oceanfront properties to exist in all of New England, ''High Scatteree'' sits proudly on nearly 3.7 acres and is sited to enjoy commanding water views. Behind tall and established hedges for the ultimate privacy, a winding gravel drive welcomes guests to the classic shingle style Main House which offers 7 bedrooms, 7 fireplaces and a thoughtful floor plan ideal for comfortable family living, or grand entertaining alike. Surrounded by meticulous lawns and gardens, a clay tennis court is found nestled on the park like grounds which include a personal arboretum of specimen trees. A 2 bedroom Guest House overlooks an award winning seaside rose garden, while steps to a private beach, deep water dock, and boathouse complement the property's many resort-like amenities. Updated and expanded several times by top builders and craftsmen, this once-in-a-lifetime property blends timeless architecture and current finishes with modern systems and infrastructure.

Listed by Brian W Dougherty of Compass Massachusetts,LLC