Chatham Homes

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

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. 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 22302404

• Residential
• Bedrooms 6
• Bathroom 8
• Square Feet 7,700
• Parking Spaces 10

Absolute perfection at this stunning in-town compound featuring commanding water views over Oyster Pond! The result of a multi-year collaboration by top architects, designers and builders, this sophisticated and turn-key coastal offering seamlessly blends classic and contemporary elements to create a one-of-a-kind retreat. Walls of glass overlook expansive lawns and gardens, while sun-drenched living spaces set the stage for large scale entertaining, or relaxed everyday living, alike. Top of the line systems and amenities are found throughout the thoughtfully designed 5 bedroom main house, while a 3 story guest house provides additional accommodations overlooking the beautiful pool and spa. Immediate access to the beach, with a private association dock, and just steps to the restaurants, shops and galleries of Chatham's quintessential Main Street, this exclusive offering is a must see, by appointment only.

Listed by Brian W Dougherty of Compass Massachusetts,LLC

MLS Number 22304126

• Residential
• Bedrooms 5
• Bathroom 6
• Square Feet 5,219
• Town Chatham

A rare offering in Chatham....Formerly part of The Plum Estate, this salt waterfront home offers stunning water views over The Oyster Pond , magnificent pool, spa and patio area and large dock capable of handling multiple boats. This 5BR home underwent a meticulous renovation between 2013-2016 ,preserving original details while optimizing the finest of today's conveniences. The original double doors open unto a truly Great room with high ceilings, fireplace, stunning water vistas and room for multiple sitting and dining areas. Adjacent is the renovated kitchen with center island, breakfast nook and ample cabinetry, A luxurious study/media room , half and full bath complete the first floor. The left side of the house opens to a private ''napping house'' with second study/media room, full bath and bedroom. The second floor offers a spacious primary suite with double closets and full bath. Three additional bedrooms share two baths. The lower level boasts a games and more room with pool table ,and additional table seating and lounging space. Coastal gardens and lawns surround for privacy. Close proximity to shopping and downtown Chatham.

Listed by Lori L Fanning Smith 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 22301766

• Residential
• Bedrooms 2
• Bathroom 3
• Square Feet 1,786
• Town Chatham

Set on a south-facing lot protected from the ocean, this Chatham escape will afford its new owners views of the Oyster Pond and a mile long stretch of Oyster River. Almost as striking is its history: it is the former working farm of Chatham Bars Inn. Owned by the same family for over 70 years, the estate could accommodate an additional 4-bedroom structure and possibly a pool bringing back the tradition of families summering together on the shore. Arrive by winding drive to the main home, built in 2004. Plentiful windows allow you to enjoy the sights with your morning coffee. A finished basement, 2 car garage and a separate barn with a garage and workshop provide ample space to store your beach gear. Watch boats drift by from the wrap around deck, spot waterfowl and church steeples in the distance, gaze at the fireworks on New Year's Eve, and see the sunset to the tune of lapping waves. Water ski, paddle down the river to Nantucket Sound, or shop in town center, which is minutes away.

Listed by Rick Smith of Gibson Sotheby's International Realty

MLS Number 22107120

• Residential
• Bedrooms 10
• Bathroom 10
• Square Feet 8,000
• Parking Spaces 15

Beautiful Chatham Georgian estate on 1.3 acres within walking distance to the center of town, Oyster Pond beach and all the amenities Chatham has to offer. Spectacular sunset views of the Oyster Pond, rolling lawns, bluestone patios and specimen landscaping surround this magnificent estate in the heart of downtown. Comprised of 10 bedrooms, 7 fireplaces, 7 full and 3 half baths, elevator and approximately 8000 square feet of living space on 3 main levels, with a grand main foyer and cantilevered staircase. The lower level includes a speakeasy bar and playroom. North and south wings of this single family home provide separate quarters for guests or family-each with 3 bedrooms, living areas and kitchens. A Chatham landmark, ''The Beechwood'' reflects unparalleled architectural detail, craftsmanship and timeless charm-perfect for large family gatherings of multiple generations under one roof.

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

MLS Number 22301578

• Residential
• Bedrooms 5
• Bathroom 7
• Square Feet 5,143
• Town Chatham

This unrivaled oceanfront estate located on prestigious Ministers Point in North Chatham offers grand scale living with dramatic Atlantic Ocean vistas. The meticulously designed cedar shingle and sprawling stone exteriors seamlessly blend the elegant interiors that boast striking architectural details, custom finishes and the highest quality craftsmanship. The 11 rooms radiate light and a breadth of picturesque vistas of Chatham's coastline and stretches of North and South Beach. The entry opens to a spectacular living and dining room with soaring coffered ceilings, an imported fireplace, and walls of windows that unveil the majestic sea backdrop. A grand family room with fireplace assures large-scale entertaining while the nearby wood paneled ensuite study delivers coziness and privacy. The main floor is complete with a fully equipped chef's kitchen that leads to a separate second floor ensuite bedroom above the garage. The main stairway leads to a magnificent master suite, a third en suite bedroom and a bookshelves sitting area. The lower level features two more ensuite bedrooms facing the sea. The grounds are mesmerizing with mature trees, native plants and paths to the sea.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

MLS Number 22303217

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

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 22300820

• Residential
• Bedrooms 5
• Bathroom 3
• Square Feet 2,459
• Town Chatham

Welcome to 95 Tisquantum, the spectacular beachfront property ideally located on Chatham's coveted Morris Island. Sited on a large and level piece of land with commanding ocean views, the existing five bedroom mid century modern has long been admired by passing walkers and boaters alike. Enjoy the home in its current iteration, or reimagine the possibilities for expansion or rebuilding with conceptual designs by famed architect Patrick Ahearn. The property features direct stairs to an expansive private beach while a large front yard provides ample space for lawn games and endless summer fun. Surrounded by nature, and just moments from the serene Monomoy wildlife sanctuary, 95 Tisquantum blends privacy and proximity so seamlessly while being just a short distance from Chatham's quintessential Main Street. A pleasure to show, by appointment only.

Listed by Brian W Dougherty 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 22205347

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

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 22301344

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 4,334
• Parking Spaces 8

New construction steps to Barn Hill Boat Landing and close to Harding's Beach. Designed with the classic coastal style of Cape Cod living and modern luxuries of a new home built for entertaining. The heart of the home is built around a sun-filled great room with 16' cathedral ceilings, gas fireplace and a show stopping 21' custom sliding door. The great room seamlessly connects directly onto a resort style pool, an expansive mahogany deck and outside shower. The stylish chef's kitchen features an oversized island, dual dishwashers, and state of the art appliances. With four large bedrooms with en suite bathrooms, plus a den and additional bonus space, there is plenty of room for family and friends. One of the bedrooms has a dedicated stairway for a primary suite or private guest quarters. Equipped with a whole house generator the home is nestled next to expansive acres of conservation land and landscaped with indigenous flora and cascading sea grasses. Professionally decorated with distinctive style throughout and is being sold completely furnished! Just unpack and enjoy!Don't miss the two virtual tours of the property. Stunning!

Listed by David C Carter of Compass Massachusetts,LLC

MLS Number 22206218

• Residential
• Bedrooms 3
• Bathroom 4
• Square Feet 3,582
• Town Chatham

Completed and ready for occupancy. A winning combination of water views and water access over the Oyster Pond , a walk to town location and a new plunge pool ! Sea Captain style inspired home with 3BR's plus den . Sited on a gentle knoll with three levels of living space. Boasting a gracious open floor plan with both living room and great room with fireplace, screened sun porch ,second floor master with luxurious en suite and water view deck, and two additional guest bedrooms. The walk out lower level provides additional study /recreational space . A lovely plunge pool with stone terrace provides even more outdoor entertaining options. Fresh coastal finishes and design elements will make this your Chatham escape or year round destination.

Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

MLS Number 22205629

• Residential
• Bedrooms 4
• Bathroom 6
• Square Feet 3,624
• Town Chatham

WALK TO VILLAGE, BEACH, PRIVATE POOL. Classic Cape Seaview Luxury in a highly desirable location. Privately elevated on a hill with views of Oyster Pond, with sandy beach across the street and also feels like it's in the countryside. Surrounded by grand-scale trees, gardens and stone work, this home was meticulously transformed and expanded in 2021. While preserving the original old Cape ambiance it also has modern convenience and luxury. The carriage house style includes a brand-new addition of a garage, family room and office that opens to a brick alfresco dining terrace sited for west-facing sunsets. Above is a truly stunning new primary en-suite bedroom with unique coastal design and a customized wardrobe. The home seamlessly flows with a grand living room that opens to a show-stopping Pebble Tec heated pool. There is a first floor en-suite bedroom, a seaside-inspired dining room with fireplace, mudroom, 2 laundries and a light-filled cathedral ceiling chef's kitchen. Above are two bedrooms, a bonus room and a bath and a half. Interiors and exteriors guarantee entertainment space and- even a little adventure with a magical backyard wooded path which leads to Cross street.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC