Chatham Homes with Cape Cod Style

Welcome to Chatham, Massachusetts, a picturesque gem nestled on Cape Cod's enchanting shores. Renowned for its stunning coastal landscapes, charming downtown, and rich maritime history, Chatham offers a unique blend of small-town charm and vibrant community spirit. With its pristine beaches, scenic lighthouses, and abundant outdoor activities, residents and visitors alike are drawn to this idyllic setting that perfectly embodies the quintessential Cape Cod experience.

The heart of Chatham lies in its captivating architecture, particularly the iconic Cape Cod style homes that dot the landscape. These charming residences, characterized by their steep roofs, dormer windows, and clapboard siding, exude a timeless elegance that pays homage to the region's rich heritage. Many of these homes are thoughtfully designed to blend seamlessly with their natural surroundings, offering breathtaking views of the Atlantic Ocean and the serene beauty of the Cape.

Living in Chatham means indulging in a lifestyle that celebrates both relaxation and adventure. Spend your days exploring the scenic beaches, where you can soak up the sun, enjoy water sports, or simply take leisurely strolls along the shore. The vibrant downtown area is brimming with delightful shops, art galleries, and restaurants serving up fresh, local seafood.

Whether you're looking for a cozy cottage or a grand waterfront estate, Chatham's real estate market offers a diverse selection of Cape Cod style homes that cater to every taste and lifestyle. Embrace the charm of Chatham and discover your dream home in this delightful coastal community, where every day feels like a vacation.

Newest Chatham Homes with Cape Cod Style

$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

$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

$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

$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

$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

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