Chatham, MA Homes for Sale

Beautiful and Historic Chatham, MA

Chatham, located on the southeastern tip of Cape Cod, is known for its beautiful beaches, charming downtown area, and rich maritime history. The town is a popular destination for tourists and second homeowners alike, drawn to its picturesque landscapes and peaceful atmosphere. With a variety of housing options, from quaint cottages to luxurious waterfront estates, there is something for everyone in Chatham.

Real Estate Market Overview

The real estate market in Chatham is strong, with a mix of year-round residents and seasonal visitors driving demand for properties. Prices have steadily increased in recent years, reflecting the town's desirability and limited inventory. Waterfront homes command the highest prices, while properties further inland offer more affordable options for those looking to buy in Chatham. With the market being competitive, it is important for buyers to act quickly and decisively when properties become available.

Chatham's Neighborhoods

Chatham is home to several distinct neighborhoods, each with its own unique charm and character. The downtown area is a hub of activity, with shops, restaurants, and galleries lining Main Street. The Old Village neighborhood is known for its historic homes and scenic views of the harbor. North Chatham boasts spacious properties with water access, while South Chatham offers a mix of year-round and vacation homes near the ocean. Buyers in Chatham have a variety of neighborhoods to choose from, each offering its own appeal.

Investing in Chatham Real Estate

With its prime location on Cape Cod and strong market fundamentals, investing in real estate in Chatham can be a sound financial decision. Rental properties are in high demand, providing a steady income stream for investors. Vacation homes can also be a smart investment, with the potential for rental income and appreciation over time. Whether you are looking for a second home, a rental property, or a permanent residence, Chatham offers a range of opportunities for real estate investors.

Working with a Local Real Estate Agent

When buying or selling a home in Chatham, it is essential to work with a knowledgeable local real estate agent who understands the intricacies of the market. A local agent can help you navigate the buying or selling process, provide valuable insights into pricing and market trends, and connect you with the right properties or buyers. With their expertise and connections, a local real estate agent can streamline the real estate transaction and help you achieve your goals in the Chatham market.

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Newest Chatham, MA Homes for Sale

$1,999,000

4 Beds ⋅ 3 Baths ⋅ 73599517 MLS

Discover the best of Cape Cod living in this beautifully situated home in desirable South Chatham. Set on a peaceful 1.38-acre lot on a quiet cul-de-sac, this inviting home offers a serene setting and a bright, open floor plan perfect for gathering with family and friends throughout the year. The spacious living room features soaring cathedral ceilings, a gas fireplace, and expansive windows that bring the outdoors in while showcasing the tranquil backyard. The dining area flows effortlessly into the chef's kitchen, complete with a center island, stainless steel appliances, abundant cabinetry, and a walk-in pantry. Enjoy relaxing summer evenings and spectacular sunsets from the three-season screened porch which opens to the expansive yard. A thoughtfully designed first-floor primary suite offers a spacious walk-in closet and private bath with double sinks and a tiled shower. An additional first-floor bedroom or home office, laundry room, and convenient mudroom off the attached one-car garage, adds to the home's functionality. The second floor offers two generously sized bedrooms, a full bath, a cozy loft area, and a versatile bonus room ideal for a home office, guest space, or additional living area. Conveniently located, just a short drive to beautiful Chatham beaches, Schoolhouse Pond, the Cape Cod Rail Trail, downtown Chatham's charming shops and restaurants, and all the amenities that make this seaside community so special. A wonderful opportunity to enjoy the space, privacy, and relaxed lifestyle of Cape Cod!

1 Williams Way, Chatham

Listing courtesy of Listing Agent: Louise Coakley from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,295,000

5 Beds ⋅ 4 Baths ⋅ 73599298 MLS

Imagine you own a house on Cape Cod! It sits high upon a hill, completely private - close to the beach, the bike path, shopping & restaurants. The home is beautifully furnished and appointed ( most furnishings can be included). We can make your dreams come true!! This (approx) 3 year young house offers 5 BR's & 4 baths. The lower level (Basement) is walk out & completely finished with a private entrance completely separate from the main living area. A beautiful paver patio surrounds the home and can include all outdoor furniture, hot tub and fire pit. Gorgeous kitchen with center Island, primary suite w/door to private deck on which you can enjoy your morning coffee. BONUS: the property is zoned duplex or 2 family & includes plans for a 2 car garage with an apartment above! Imagine sitting in your hot tub on your private oasis enjoying a perfect Cape Cod summer day! The roof top deck is a perfect place to enjoy refreshments & star gaze. Or maybe you'd like to hop on your bike & ride down the bike path to 'Short & Sweet' for an ice cream cone! All this and more is waiting for you!

2388 Main St, Chatham

Listing courtesy of Listing Agent: Nicolette Lisella from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$475,000

2 Beds ⋅ 1 Baths ⋅ 73598199 MLS

Tucked along a quiet lane in North Chatham, this beautifully refreshed second-floor condominium offers effortless coastal living in one of Cape Cod’s most coveted towns. Truly move-in ready, the home unfolds in an open, airy floorplan where natural light pours across gleaming hardwood floors and frames serene views of the surrounding marshland. An oversized picture window captures the shifting beauty of the marsh, an idyllic backdrop for morning coffee or evenings beside the wood-burning fireplace. The upgraded kitchen with granite counters and the updated bath share the same polished, low-maintenance appeal. A shared balcony and shared yard invite you to savor the natural setting, while private laundry, basement storage, a detached garage, and additional parking add everyday ease. Stroll to nearby shops and coffee, and enjoy easy access to North Chatham’s beaches. Whether as a refined entry into the Chatham market, a turnkey seasonal retreat, or a long-term investment with room to enhance, this is an exceptional opportunity to make Chatham home.

109 Misty Meadow Unit 4, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$5,900,000

4 Beds ⋅ 6 Baths ⋅ 73596909 MLS

An Ed Acton/Harbor Builders home built in 2019, located in the highly desired section of North Chatham. Offering 4 bedrooms, 6 bathrooms, this home has expansive views of Chatham Harbor and the ocean beyond. Over 5,000 sqft of refined entertainment space meeting town requirement for a large pool/spa area if desired. The necessary piping has already been installed on this level plot of land. The property has mature flowering gardens. Inside the home is showered with light, offering high ceilings with a great flow throughout. The lower level was built out in 2021 into a beautiful wine tasting room and an area for watching sports and movies, pool table and exercise area. There is a first floor en-suite bedroom for guests with the primary bedroom on second level with balcony offering panoramic views the water. Buyers and their agents are encouraged to confirm all information. Blending formal and casual entertaining this home is a must see for the discriminating buyer. Please call listing agent, for an exclusive showing.

48 Hillcrest, Chatham

Listing courtesy of Listing Agent: William Storff from Listing Office: Compass.

$699,999

3 Beds ⋅ 2 Baths ⋅ 73596255 MLS

***OPEN HOUSE Sun 11/8 11:30-12:30pm!*** Opportunity awaits in Chatham! Nestled on a quiet, desirable street, this 3 bed, 2 bath home with en suite offers 1,624 sf of living space on a half acre lot. A standout feature is the expansive great room with vaulted ceilings, a wet bar and a slider opening to a deck. Extending across the rear of the home from the great room to the dining room, with access from both spaces, the deck creates an ideal indoor-outdoor setting for relaxing and entertaining. An outdoor shower adds to the Cape Cod lifestyle appeal. While in need of updating, the property presents tremendous potential to renovate, customize and build equity in a premier Cape Cod location. Enjoy the privacy and space afforded by the mature trees and bushes while being conveniently located near Chatham's beaches, downtown shops, restaurants and recreational amenities. Whether you are looking for a year round residence, vacation home or investment opportunity, this property is ready for your vision and personal touches.

25 Clifford Pl, Chatham

Listing courtesy of Listing Agent: Catherine Walsh from Listing Office: Coldwell Banker Realty - Easton.

$589,000

3 Beds ⋅ 1 Baths ⋅ 73595531 MLS

Phenomenal location with everything "Chatham" right around the corner. This home is 1 block from the rail trail into town, 1 mile from Chatham Village by car, and 1.5 miles from the fish pier and Claflin Landing, all via quaint and quiet back roads. The house itself offers 3 bedrooms and 1 full bath with possible expansion potential in the full basement with town approval. New gas furnace in 2023, garage under, and a large lot abutting town land. Septic is a cesspool and design/replacement will be buyer's responsibility. Bring your contractor and make your Chatham dreams come true!

193 Heritage Ln, Chatham

Listing courtesy of Listing Agent: Ned Chatelain from Listing Office: Chatelain Real Estate.

$779,000

3 Beds ⋅ 2 Baths ⋅ 73595488 MLS

Perched on an elevated, beautifully sited lot in the quiet Countryside neighborhood, 49 Duck Marsh Lane offers an accessible entry point to one of the Cape's most coveted markets. This single-level ranch is a true now-and-later proposition: ready to enjoy today, with room to grow tomorrow. The open-concept living room is filled with natural light and anchored by a fireplace, flowing to a dedicated dining room and a kitchen refreshed with painted cabinetry and newer appliances. Three generously sized bedrooms and two baths adapt easily to full-time living, family getaways, guests, or a home office. An expansive lower level awaits finishing to suit your vision, complemented by a garage. Outside, the back deck sets the stage for gatherings, while the expansive yard invites gardens, play, or future enhancement. Well maintained with upgraded systems, efficient natural gas, and underground utilities, the home is ready from day one. Minutes to Ridgevale and Cockle Cove beaches, Chatham village, and Harwich Port, it is ideal as a year-round residence or a second home in an area poised for continued appreciation. Flexible, manageable, and unmistakably Chatham.

49 Duck Marsh Lane, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$1,175,000

2 Beds ⋅ 3 Baths ⋅ 73594614 MLS

Discover one-story living in Chatham's desirable Riverbay Estates. Set on a beautifully landscaped .64-acre corner lot, this inviting 2-bedroom, 3-full-bath Cape Ranch offers classic charm and comfortable living. The interior features a living room with fireplace, spacious dining room, sunroom opening to a large deck, and kitchen with pantry, Viking gas range, center island, and granite countertops. This home offers two bedrooms, including a primary bedroom with ensuite bath. Hardwood floors add warmth throughout. The finished basement provides additional living space with a family room, full bath, and laundry room. Enjoy the outdoors from the large rear deck or covered front porch, surrounded by mature plantings and exceptional landscaping. Additional features include gas heat, two split units for A/C, and an attached two-car garage. Riverbay Estates spans 285 acres of winding streets and offers access to two kettle ponds in a peaceful natural setting.

789 Riverview Drive, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$9,495,000

3 Beds ⋅ 3 Baths ⋅ 73594589 MLS

Sparkling harbor views, afternoons by the pool, and expansive, private grounds on coveted Shore Road. Offered for the first time since 1987, "Offshore" encompasses more than an acre - a rare opportunity to enjoy a remarkably private estate-like setting in the heart of Chatham. Beyond the house, a surprising expanse of lawn and gardens unfolds, its scale and privacy revealed only when you explore the grounds. Inside, gracious, generously proportioned rooms and timeless Cape Cod character create an inviting setting for entertaining, gathering with friends, 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 windows frame picture-perfect coastal scenes. A spacious first-floor primary suite offers comfort and ease. A carriage-style garage completes the property, just moments from Chatham Bars Inn, the Fish Pier, Lighthouse Beach, and Main Street. Whether enjoyed as it is today or thoughtfully reimagined, this special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

153 Shore Rd, Chatham

Listing courtesy of Listing Agent: Sarah Keith from Listing Office: eXp Realty LLC.

$739,000

3 Beds ⋅ 2 Baths ⋅ 73594309 MLS

Classic Cape charm meets a fresh, inviting interior in this beautifully updated 3-bedroom, 2-bath home! An open floor plan welcomes you with hardwood floors, an updated kitchen, and a dining area that flows into the living room, where a cathedral ceiling and fireplace create a wonderful gathering space. Two bedrooms are upstairs, with the third bedroom on the lower level. A lower-level bonus room offers added flexibility, with a newer slider opening to the patio for easy outdoor entertaining. A new bathroom with radiant floor heating adds everyday comfort, while a new boiler, three ductless AC units, newer windows, and PVC trim enhance comfort and ease of maintenance. The garage includes generous storage in the unfinished loft above. Enjoy an exceptional location just one-tenth of a mile from the bike path, 1.2 miles from Forest Beach on Nantucket Sound, and conservation access just across the street, one lot away. A wonderful opportunity to enjoy the Cape Cod lifestyle!

235 Morton Rd, Chatham

Listing courtesy of Listing Agent: Natalia Weiner from Listing Office: Gibson Sotheby's International Realty.

$5,800,000

3 Beds ⋅ 6 Baths ⋅ 73593924 MLS

Located in the highly coveted Harbor Coves Association, this stunning Gambrel-style residence, currently under construction by Harbor Builders, offers an exceptional blend of timeless architecture, elegant living spaces, and resort-style outdoor amenities. The inviting main level features a chef's kitchen that opens up to both the designated dining area and spacious living room. The luxurious first floor primary bedroom offers a private retreat with an en suite bathroom and walk-in closet, complemented by a laundry room and mudroom. Upstairs, two additional en suite bedrooms provide comfort and privacy, along with a spacious family room and office space. The finished lower level expands the living space with a home theatre, exercise room and full bath, ideal for hosting guests. Outdoors, a sparkling in-ground pool, surrounded by beautifully designed grounds creates a private oasis for relaxing and entertaining. With access to a private association beach on Crow's Pond, this North Chatham home provides the best of Cape Cod living.

160 Woodland Way, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$995,000

2 Beds ⋅ 1 Baths ⋅ 73592561 MLS

Discover the essence of Cape Cod living at this waterfront retreat on Stage Harbor. Tucked away on a quiet lane yet close to Chatham Village, the property offers sweeping views with ever-changing tidal scenery, birdlife, and spectacular sunsets. The home features a welcoming coastal vibe with sun-filled living spaces, while outdoor areas are ideal for entertaining or quiet reflection. A firepit sets the stage for summer evenings, the perfect way to end the day toasting marshmallows. Whether enjoyed as a seasonal getaway or a year-round residence, 20 Cedar Swamp Lane captures the very best of Chatham. Buyers and agents, please verify all herein.

20 Cedar Swamp Lane, Chatham

Listing courtesy of Listing Agent: Ellen Valentgas from Listing Office: Sotheby's International Realty.

$870,000

3 Beds ⋅ 2 Baths ⋅ 73590218 MLS

Tucked away in one of Chatham's most desirable neighborhoods, this charming Cape Cod retreat offers the perfect blend of privacy, comfort, and coastal living. Situated on a generous 0.76-acre lot, this well-maintained three-bedroom, two-bath home provides nearly 1,900 square feet of inviting living space designed for year-round enjoyment or the ideal vacation getaway. The thoughtfully designed interior features bright, sun-filled living spaces, an inviting floor plan, and seamless indoor-outdoor flow ideal for entertaining. Spacious bedrooms, and comfortable gathering areas create a warm and welcoming atmosphere. Outside, landscaped grounds, multiple outdoor living spaces, and the tranquility of Round Cove provide the perfect setting for relaxing summer evenings.Welcome to Round Cove Road Chatham.

304 Round Cove Rd, Chatham

Listing courtesy of Listing Agent: Kimberly Arena from Listing Office: Venture.

$2,199,000

3 Beds ⋅ 3 Baths ⋅ 73590086 MLS

Renovated without compromise, finished to the last detail. Set on a generous and private lot in Chatham's sought-after Riverbay neighborhood, 312 Round Cove Road has been thoughtfully reimagined inside and out, offering effortless, turnkey living just minutes from Jackknife Cove, Pleasant Bay and Main Street. Out back, summer starts at home: a new heated pool with automatic cover and patio, a pool cabana and bar made for hosting, stunning hardscaping, and a fully fenced yard where pets can roam freely. Inside, a vaulted great room with shiplap ceilings and recessed lighting flows into an open-concept kitchen with custom cabinetry and quartz countertops. A private dining room with built-ins sets the stage for holiday dinners and summer suppers. Three main-level bedrooms include an ensuite primary, and a finished lower level adds flexible recreation space for movie nights, games or a home gym. No contractors, no waiting lists, no projects. Just unpack and dive in. Spend mornings paddling Pleasant Bay, evenings watching the sunset at Jackknife Cove, and warm nights under the stars by the pool. Riverbay has never been more desirable, and homes this complete rarely come to market.

312 Round Cove Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$599,999

2 Beds ⋅ 1 Baths ⋅ 73589780 MLS

Attention all contractors and investors! This 2 bed, 1 bath Chatham fixer-upper offers great potential and a location that's hard to beat. Passing Title 5. Ridgevale Beach is just a short walk down the lane with additional beaches nearby and Chatham's historic charm, local sights and Cape Cod lifestyle all within easy reach. Offered as is and priced accordingly. Bring your ideas and create something special in Chatham.

15 Eddie Ln, Chatham

Listing courtesy of Listing Agent: Catherine Walsh from Listing Office: Coldwell Banker Realty - Easton.

$849,900

3 Beds ⋅ 2 Baths ⋅ 73589192 MLS

Enjoy the best of Chatham living in this sun-filled home with a desirable southern exposure. The main level features a spacious primary bedroom with walk-in closet, full bath, office, dining room, generous living room and welcoming kitchen. Newer sliders open to a two-story wraparound Azek deck with gazebo—perfect for summer dinners, morning coffee and entertaining, with seasonal peeks of Mill Pond. The lower level offers two additional bedrooms, a full bath, laundry room and foyer with direct access to the two-car garage. A large walk-up attic provides excellent potential for future expansion. Custom built by Cape Associates and originally designed as a passive solar home, the property is now fully electric with owned solar panels that generate credits throughout the year, plus central air. Ideally located near Chatham's beaches, shops and restaurants, with convenient access to neighboring Harwich.

25 Partridge Path, Chatham

Listing courtesy of Listing Agent: Cape Island Estates Group from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$1,650,000

3 Beds ⋅ 3 Baths ⋅ 73586414 MLS

Stunning inside and out. Designed by a professional architect to optimize comfort, entertainment and efficiency. The entire property is meticulously maintained and beams with pride. The private grounds are brimming with an abundance of gardens, flowering plants and ornamental trees. The welcoming pool, play shed, firepit, patio, and side yard for lawn games creates an outdoor living experience that combines beauty and fun. Outside extends in to the home through oversized sliders into a dramatic 13ft. cathedral living room with customized built ins. Beautiful bead board ceilings, hardwood floors, open floor plan and dry basement ready to be finished. Comfortable dining and sitting area, state of the art kitchen with induction cooktop, Electrolux and Bosch appliances with granite countertops. Primary with en-suite and den/office with enough room to sleep guest and attached bath with jetted tub completes the floor. Two cozy bedrooms with full bath on second floor giving you that relaxed at home feeling. This treasured property is the epitome of a tranquility and luxury. Great investment potential with rental history.

764 Riverview Dr, Chatham

Listing courtesy of Listing Agent: Sharon Mabile from Listing Office: .

$1,275,000

4 Beds ⋅ 3 Baths ⋅ 73585978 MLS

Offering exceptional space and versatility on 0.82 acres, this expansive four-bedroom Chatham home is just one mile from Ridgevale Beach and approximately six minutes from both downtown Chatham and Harwich Port. Generous living and dining areas provide ample room to gather and entertain, making the property ideal for year-round living, summer getaways, or a vacation rental investment. The gourmet kitchen features a Wolf range, warming drawer, granite countertops, and oversized center island. A spacious primary suite offers a walk-in closet and luxurious en-suite bath, while three additional bedrooms comfortably accommodate family and guests. A welcoming porch and wraparound decks overlook the private backyard. Additional amenities include central A/C, a Jotul wood stove, tankless water heater, natural gas grill, town sewer, and a separate storage or workshop outbuilding. An unfinished partial walkout basement offers further potential. A rare opportunity for space, flexibility, and convenience in Chatham.

2118 Main St, Chatham

Listing courtesy of Listing Agent: Marcie Smith from Listing Office: Gibson Sotheby's International Realty.

$829,000

4 Beds ⋅ 2 Baths ⋅ 73585326 MLS

2673 Main St, Chatham

Listing courtesy of Listing Agent: Barbara Garside from Listing Office: eXp Realty LLC.

$3,995,000

3 Beds ⋅ 5 Baths ⋅ 73584596 MLS

Exceptional new construction in coveted North Chatham, where timeless Cape Cod architecture meets sophisticated modern design. Offering more than 4,400 square feet of finished living space, this impeccably crafted residence features a first-floor primary suite with spa-inspired bath, private office, elegant dining room, and a stunning gourmet kitchen with Wolf and Sub-Zero appliances opening to beautifully appointed living spaces. The second floor offers two spacious bedrooms, two full baths, and a versatile bonus room. A finished lower level with exceptional ceiling height provides approximately 1,100 square feet of additional living space, ideal for a media or game room, gym, and recreation area with full bath and direct access to the pool and spa via a handsome stone staircase. Custom finishes, refined craftsmanship, a white stone driveway edged with cobblestone, and beautifully landscaped grounds create a sophisticated Cape Cod arrival. Just minutes from North Chatham beaches and harbor, Chatham Village, renowned shops, restaurants, and the best of coastal living.

35 Crows Pond Rd, Chatham

Listing courtesy of Listing Agent: Betsy Hargreaves from Listing Office: Gibson Sotheby's International Realty.

$950,000

3 Beds ⋅ 3 Baths ⋅ 73583268 MLS

Pisces Coastal Kitchen and the mixed-use real estate at 2653 Main Street in South Chatham are offered together for $950,000. The acquisition combines an established full-service restaurant and bar, commercial kitchen, second-floor apartment, and attached residential cottage within one Route 28 property. The exclusive listing agreement specifically provides for the business and real estate to be sold together as a single offering.The approximately 2,252 SF building is situated on a 9,401 SF parcel and is identified in public records as commercial/office/residential mixed use. This configuration provides an owner-operator or hospitality investor with both an operating business and control of the underlying real estate, along with residential space that can support the operation or provide additional income potential.

2653 Main St, Chatham

Listing courtesy of Listing Agent: Kevin A. Pepe from Listing Office: Commercial Realty Advisors, Inc..

$2,285,000

5 Beds ⋅ 4 Baths ⋅ 73582831 MLS

The magic here is in the location .... leave the car behind, grab a towel and head to stunning Ridgevale Road Beach, a mere 1/10th mile away. This 5-bedroom, 4-bath Chatham residence is privately positioned on .81 acres of natural surroundings offering a rare sense of privacy. From the moment you enter this pristine home, abundant natural light, gleaming hardwood floors and an inviting sense of ease set the tone. The spacious eat-in kitchen opens via sliding doors to a west-facing deck, ideal for taking in the ever-changing salt marsh views .A handsome brick wood-burning fireplace centers the living room while an adjoining office/den and full laundry room add convenience. The flexible second level floor plan includes TWO options for primary bedroom suites, one of which could also serve as private guest quarters or rental potential with its own access. A ready-to-be-finished walkout basement with radiant heat , an extra deep two-car garage and abundant storage provide functionality rarely found in a beach property of this caliber. Your Chatham Beach House is right here - and it feels like it's always been waiting for YOU.

20 Stoughton Lane, Chatham

Listing courtesy of Listing Agent: Elaine Lomenzo from Listing Office: William Raveis Real Estate & Homes Services.

$6,575,000

4 Beds ⋅ 5 Baths ⋅ 73582098 MLS

Few homes command Oyster Pond like 12 Pond Street. Three soaring peaks, the center crowned in sculptural rounded copper, announce a custom Eastward Companies build of rare craftsmanship, with immediate proximity to Main Street and the beach. Inside, every room turns toward the water. The open first floor is anchored by a kitchen perched above stunning views, its custom cabinetry and large island opening to a fireplaced living and dining area that flows to the waterfront patio. Just beyond, the primary suite offers built-ins, a gas fireplace, a walk-in closet, and a spa-like bath. Hardwood, high ceilings, and exceptional millwork carry throughout. Upstairs, a vaulted family room with wet bar opens to a porch set above the water, joined by three bedrooms and two full baths. Below, a fully equipped gym and entertaining space. Outside, a full paver driveway, retaining walls, and terraced bluestone patios frame hydrangeas and lush native plantings, with a gas firepit, outdoor shower, and generator. A deeded association dock and mooring field deliver some of the finest boating and recreation on the Cape. A show house, purpose-built for entertaining and for a life lived on the water.

12 Pond St, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$3,999,000

5 Beds ⋅ 5 Baths ⋅ 73581092 MLS

Beyond the Chatham Lighthouse, with over an acre on Morris Island, a five-bedroom estate of more than 5,000 square feet keeps its own quiet company. Deeded beach rights through the Quitnesset Association put the sand a short stroll away, while Main Street waits minutes behind you. A grand staircase rising from the foyer gives arrival a true sense of occasion. At the heart of the home, a vaulted living room gathers light through walls of windows, framing an expansive deck and serene, private grounds with room for a pool. To the left, a private wing pairs the primary suite with a dedicated office. Formal dining flows to a spacious kitchen with a large island, bar seating, and a breakfast nook with sliders to the yard, while a sunroom invites the seasons in. Upstairs, four generous, light-filled bedrooms, several en suite, welcome family and guests across generations. Above the two-car garage, a sprawling recreation room is poised to become a guest suite. A mudroom, first-floor laundry, and outdoor shower make easy work of long beach days. Morning on the sand, evening on Main Street, and every hour between on your own acre. A rare and prestigious Chatham estate, built for gathering.

169 Tisquantum Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$2,199,900

3 Beds ⋅ 4 Baths ⋅ 73579550 MLS

This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers Lake. Thoughtfully renovated in 2010, the main residence features an inviting and comfortable floor plan designed for relaxed living and entertaining. The updated kitchen with pantry opens to the dining area and living space, where views of the pool and grounds create a wonderful connection to the outdoors. A full bath and flexible office or bonus room provide additional options for guests, working from home, or overflow accommodations. Upstairs, the spacious primary suite offers a private retreat with a walk-in closet and en-suite bath featuring a whirlpool tub. A second en-suite bedroom and separate laundry room complete the upper level.Adding tremendous flexibility is the detached two-car garage with a private one-bedroom, one-bath apartment above—ideal for extended family, guests, a home office, or additional income or living space. Outdoors, the pool and surrounding patio serve as the centerpiece of the property, with nearly two acres providing ample room to gather, entertain, garden, or simply enjoy the tranquility of the natural surroundings. Deeded access to Lovers Lake and proximity to Ryder's Cove offer endless opportunities to enjoy life on the water, while Chatham's beaches, boating, dining, shopping, and village amenities are just a short drive away. Additional features include central air conditioning, natural gas, and an owned solar system. Offering the privacy of a country retreat with access to everything that makes Chatham so desirable, "The Compound" is a distinctive Cape Cod property with possibilities for generations to enjoy.

20 Lords Pond Lane, Chatham

Listing courtesy of Listing Agent: Andrew Grattan from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$1,495,000

2 Beds ⋅ 2 Baths ⋅ 73577973 MLS

Welcome to 39 Jedidiah Way, a beautifully maintained Cape Cod residence set on an elevated, meticulously landscaped half-acre at the end of a quiet cul-de-sac. Offering privacy, direct access to the bike path, and convenient proximity to Chatham’s beaches, recreation, restaurants, and village amenities, this inviting home presents an exceptional opportunity to embrace the Cape Cod lifestyle. A welcoming foyer introduces a bright, open interior highlighted by soaring vaulted ceilings and a handsome brick, wood-burning fireplace that anchors the living room. The adjoining dining area opens through sliding glass doors to an expansive rear deck, creating a natural extension of the living space and an ideal setting for summer entertaining, outdoor dining, or simply enjoying the beautifully landscaped and private backyard. The well-appointed kitchen features a center island, pantry, generous workspace, and a comfortable layout designed for both everyday living and entertaining. Completing the first floor is a spacious bedroom, full bath, and conveniently located laundry, providing the flexibility of single-level living. An oak staircase leads to the second floor, where a dramatic loft overlooks the living area below and offers versatile space for a home office, reading area, or additional gathering space. The generously proportioned second bedroom features a defined sitting area and an impressive walk-in closet, with a second full bath completing this level. One of the property's most distinctive features is found just beyond the backyard: a private gated path provides direct access to the Old Colony Rail Trail, placing miles of scenic walking, jogging, and cycling virtually at your doorstep. Schoolhouse Pond, Volunteer Park, conservation areas, and Chatham’s many recreational amenities are also nearby, while Ridgevale Beach and the waters of Nantucket Sound are approximately one mile away. Additional amenities include natural gas heat, central air conditioning, town water, irrigation supplied by a private well, and an unfinished lower level offering excellent storage and future possibilities.

39 Jedidiah Way, Chatham

Listing courtesy of Listing Agent: Andrew Grattan from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$4,250,000

4 Beds ⋅ 5 Baths ⋅ 73576453 MLS

This exceptional Chatham residence blends coastal luxury with country farmhouse charm in the exclusive Stage Neck neighborhood. Sited on nearly an acre lot with a separate barn/out-building, this property allows for privacy, with easy access to the Chatham Loop and vibrant downtown life. Abundant curb appeal starts with the circular driveway, mature plantings, and covered mahogany farmer's porch. Step inside to a home created by one of the Cape's finest craftsmen; custom built with meticulous care and quality. The floor plan provides multiple living areas on two levels, combined with open living spaces today's Buyers are seeking. Four en-suite bedrooms including a wonderful primary on the first floor w/amazing walk-in closet. Bright, renovated granite and stainless kitchen w/breakfast bar, center island, butler's pantry, and wet bar. Spacious living room offers a slider to a deck overlooking the yard. The first floor also encompasses a dining room, office nook, and full laundry room. Three fireplaces, beautiful wood floors, custom crown moldings, built-ins, natural gas heat, Central A/C, outside shower, well-irrigation, 2-car garage, full basement, and so much more. The stunning lot includes a charming barn with many possibilities: workshop, artist studio, kayak storage, or park a tractor! Properties like this don’t come along very often; this is one-of-a-kind offering in a remarkable location. Whether you desire a Summer retreat or elegant year-round living, you will find it here at 22 Moonpenny Lane!

22 Moonpenny Ln, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$619,000

2 Beds ⋅ 2 Baths ⋅ 73571094 MLS ⋅ ['Nickerson Corners'] BLDG.

Spacious and sunny condo in North Chatham set on the corner of Stoney Hill Rd. Walk to Cow yard beach and admire the historic homes along the way. Or walk in the opposite direction towards down town Chatham. The location and size of this condo will win your heart. Offered completely furnished with many recent upgrades including new AC, new deck, new windows and roof. This condo is graced with beautiful wood floors and a fireplace with built in book shelves that make this condo feel like a home. There are 2 spacious bedroom and 2 full bathrooms. This condo has a solid rental history making it a smart investment.

216 Orleans Rd Unit D, Chatham

Listing courtesy of Listing Agent: Kathleen Phelan from Listing Office: Compass.

$2,140,000

4 Beds ⋅ 3 Baths ⋅ 73571912 MLS

A meticulously maintained and beautifully decorated beach home awaits you in quaint village of South Chatham.Ideally situated between downtown Chatham and Harwich Port, this exceptional property offers the perfect blend of comfort, privacy, convenience and classic Cape Cod charm.Nestled near Forest Beach,Mill Creek,the Cape Cod Rail Trail, tennis court and conservation areas, this puts nature and recreation at your fingertips.The spacious home features 4 bedroomsand 3 baths providing plenty of room for family and guests. Thoughtfully designed for comfortable living and surround sound for entertaining, the home offers inviting spaces inside and out.The two car garage has been transformed into a fantastic game room complete with air hockey, ping pong and foosball-a wonderful space for kids and adults alike.Outside, the beautifullylandscaped yard and gardens are irrigated by a private well, keeping everything lush throughout the season. Three decks, one is a roof top, outdoor shower,firepit, patio creat the perfect setting for relaxing, entertaining and enjoying the warm Cape Cod evenings.The home is being offered partially furnished.

20 Circle Drive, Chatham

Listing courtesy of Listing Agent: Barbara Carroll-Horne from Listing Office: Gibson Sotheby's International Realty.

$5,250,000

4 Beds ⋅ 5 Baths ⋅ 73571701 MLS

Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings define the first floor, anchored by a vaulted beam-ceiling primary suite with a spectacular spa-inspired bath. The generous eat-in kitchen and family room feature a dramatic shiplap-vaulted ceiling and open to a sun-drenched patio surrounding a heated plunge pool and oversize yard with unlimited potential. A second-floor deck overlooks the secluded grounds, while an additional primary en-suite and two bedrooms and two more baths complete the upper level. Stroll to Chatham Bars Inn, the Fish Pier and Main Street - an enviable setting where the best of Chatham is truly at your doorstep.

106 Barcliff Ave, Chatham

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.

$675,000

2 Beds ⋅ 2 Baths ⋅ 73568884 MLS ⋅ ['Nickerson Corners'] BLDG.

Wonderful two-bedroom, two bath end unit condominium close to Chatham village and beaches.. Recently renovated and three split units for heat and air conditioning also added. Plenty of parking and storage and all the work is done for you. Insurance, landscaping, trash pickup, exterior maintenance, professional management, snow removal, are all covered in the reasonable monthly association fee. Leave all the work to others and enjoy everything Chatham and Cape Cod have to offer. Affordable for either year-round or seasonal use or rent it out for part of the year..........Being sold mostly furnished for no additional cost.......This information has not been independently verified, and buyer should do their own due diligence by checking with town bylaws zoning, and their attorney

210 Orleans Road Unit C, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.

$1,325,000

2 Beds ⋅ 3 Baths ⋅ 73568802 MLS

One of the iconic Christopher Ryder House condominiums can be yours in time for the Fall season. This elegant two-bedroom, three-bath home blends timeless architectural character with refined two-level living. Gracious rooms, high ceilings, oversized windows, skylights, original beams, and warm wood floors create an inviting atmosphere throughout. The open floor plan features a spacious living room with gas fireplace flowing seamlessly into the dining room space and updated chef's kitchen—perfect for entertaining. A sunlit office space opens through sliding doors to a private patio, ideal for gatherings, gardening, or a peaceful outdoor retreat. The primary suite offers a walk-in closet and updated bathroom. The spacious second bedroom enjoys a nearby full hall bath, with the additional second office space providing flexibility for work or guests. Interior access to the garage, along with additional storage, adds everyday convenience. A rare opportunity to enjoy architectural charm, modern comfort, and effortless living in one exceptional home.

1114 Orleans Rd Unit 8, Chatham

Listing courtesy of Listing Agent: Betsy Hargreaves from Listing Office: Gibson Sotheby's International Realty.

$810,000

1 Beds ⋅ 2 Baths ⋅ 73557769 MLS

This house was designed and built by Grattan Gill, a Taliesin Fellow and Frank Lloyd Wright apprentice (1952-57). This distinctive South Chatham home showcases timeless architecture, thoughtful design, and modern comfort. The main level offers the convenience of first-floor living, featuring a spacious primary bedroom, a full bath and direct access to a private balcony overlooking the expansive rear deck—an ideal setting for morning coffee or evening relaxation. The walkout lower level adds exceptional versatility with a second full bathroom, a generous bonus room perfect for guests, a home office, or recreation space, along with a dedicated laundry area and abundant storage. Additional highlights include central air conditioning, a whole-house generator for peace of mind, and a desirable South Chatham location close to beaches, shopping, dining, and all that Cape Cod has to offer. This is a rare opportunity to own a home that blends architectural pedigree with everyday functionality in one of the Cape’s most sought-after communities.

24 Deep Water Ln, Chatham

Listing courtesy of Listing Agent: Karen St. Amand from Listing Office: Today Real Estate, Inc..

$1,695,000

2 Beds ⋅ 4 Baths ⋅ 73561031 MLS

Discover coastal living in this custom-built 2015 contemporary Cape, just 3/10 mile from Forest Beach in desirable South Chatham. Approximately 2,300 sq. ft. includes 2 spacious en-suite bedrooms with walk-in closets, 3½ baths and extra space in the finished basement with full bath. The open floor plan features 8-10' ceilings, abundant natural light, and white oak floors. The kitchen opens to the dining and living areas with a gas fireplace. Amenities include Anderson Stormwatch windows, gas heat, central air and underground utilities provide year-round comfort. The finished lower level offers a Jacuzzi bath, antique pine bar, and pool table. Quality construction includes double-dipped cedar shingles, Azak trim and decking, heavy-duty asphalt roof, and three porches (two covered). This south-facing lot offers close proximity to Nantucket Sound. Close to Forest Beach, post office, restaurants, package store, and Cape Cod Rail Trail, this beautifully crafted home offers exceptional quality, comfort and a location in one of South Chatham's most desirable neighborhoods.

43 Tobey Turtle, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$1,795,000

3 Beds ⋅ 2 Baths ⋅ 73561027 MLS

Experience the ultimate waterfront lifestyle in this lovely coastal retreat. Perfectly positioned on the edge of Frost Fish Creek, this charming home captures picturesque water views and is thoughtfully designed for effortless indoor-outdoor living. Enjoy direct tidal access to one of Cape Cod's most treasured waterways. Secure a private mooring and launch your kayak, paddleboard, or boat right from your backyard. Meander through scenic Frost Fish Creek into Ryder's Cove and the sparkling waters of Pleasant Bay, where endless opportunities for boating, sailing, fishing, shellfishing, and exploring pristine beaches await. Continue beyond to discover one of New England's most spectacular estuaries and its gateway to the Atlantic Ocean. The expansive rear deck provides the perfect setting for entertaining guests or simply relaxing beneath the stars while taking in the peaceful waterfront setting and ever-changing coastal views.Buyer is responsible for the design and installation of a septic system. Septic engineering is currently underway to determine whether the property will support a two- or three-bedroom septic system.

71 Rowland Drive, Chatham

Listing courtesy of Listing Agent: Dawn Marie Boynton from Listing Office: .

$2,295,000

4 Beds ⋅ 4 Baths ⋅ 73548377 MLS

Exceptional Great Hill Estates retreat being offered fully furnished, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short foot path away. Located on a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out. A first-floor primary suite features ensuite bath and laundry for convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent great rooms with vaulted beamed ceilings and fireplaces. A wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs are two bedrooms and a full bath, including one bedroom with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, another laundry area, and direct access to a stone patio with custom seating and gas fire pit. Additional highlights include central ac, hardwood floors, two-car attached garage and new Bosch heating system. Close to Chatham Village, Lighthouse and Hardings beaches, bike path and tennis courts.

55 Winterset Drive, Chatham

Listing courtesy of Listing Agent: Janet Stuart from Listing Office: Coldwell Banker Realty - Concord.

$1,469,000

5 Beds ⋅ 10 Baths ⋅ 73548115 MLS

New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho and Pleasant Bay from nearly every angle. The shingle-style exterior is substantial and classic Cape Cod, with a two-car garage and a private boat dock giving direct access to the water. The open, airy living room has a stone fireplace, window seats and vast water views throughout. The kitchen continues the view with a Wolf gas range, a large island with seating and doors opening to an expansive deck overlooking Crows Pond. The three-level layout includes a quiet office, a lower-level gym, an indoor sauna and a guest suite with its own full kitchen and living room. An elevator connects all floors. The pool, patio and private boat dock anchor Fox Hill's outdoor sequence, with sunrise and sunset views in one of Cape Cod's most storied seaside towns.

558 Fox Hill Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$5,900,000

4 Beds ⋅ 5 Baths ⋅ 73544856 MLS

Classic Cape Cod home on a one-acre lot on the nicest street in Chatham.... Nooks and crannies and rooms and additions in several directions in this very private location of North Chatham....Choice of three 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 heated Gunite pool...Property 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, Chatham

Listing courtesy of Listing Agent: John Burke from Listing Office: William Raveis Chatham.

$6,500,000

10 Beds ⋅ 10 Baths ⋅ 73535185 MLS

Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500 sq ft with 10 bedrooms and 10 bathrooms. Inside, enjoy hand-painted murals, sweeping water views, curved staircases, intricate woodwork, and beautifully scaled living spaces filled with character. The lower level features a ''speakeasy'', ballroom, workshop, and storage. Outside, expansive terraces, mature gardens, bluestone walkways, towering trees, and rolling lawns create a spectacular setting leading toward the water. The property was divided into three townhouse residences, but has since been used as a single-family home. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$5,900,000

6 Beds ⋅ 8 Baths ⋅ 73533378 MLS

The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every bedroom ensuite. An open-concept great room with soaring ceilings anchors the floor-plan, while a fully finished basement provides a complete auxiliary level for guests and entertaining — a depth of program rarely found. Outside, a pool and integrated jacuzzi anchor the aquatic experience, framed by a dramatic firewall feature and wraparound deck purpose-built for outdoor living at scale. Constructed by R.A. Martin — among the most trusted names in Chatham construction — the property offers a rare opportunity to customize finishes to suit. A singular proposition in the Chatham marketplace!

50 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 73531412 MLS

Canoe and kayak on Mill Pond. Direct water front at the end of the cul-de-sac. Turn key - Fully furnished year round and off season rental histoy. Very private and peaceful setting yet conveninet to shopping, restaurants, beaches and highways. 3 Bedrooms, 2 baths. First floor master. Plenty of closet space. Walkout basement. Large deck overlooking Mill Pond. Gas fireplace instert. Gas stove. Washer and dryer. May assume summer rentals.

35 Duncan Lane, Chatham

Listing courtesy of Listing Agent: John Habeeb from Listing Office: Alliance Realty Advisors, Inc..

$4,995,000

4 Beds ⋅ 4 Baths ⋅ 73529657 MLS

Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed to maximize its breathtaking setting, the light-filled open floor plan features walls of glass and stunning water views from nearly every room. The main level includes a spacious living room with fireplace, dining area, updated kitchen, two bedrooms, and a shared bath. Upstairs, two private en-suite bedrooms enjoy elevated harbor vistas. The walkout lower level offers a family room and fitness space overlooking the water. A 2025 kitchen renovation, 2019 revetment, direct water access for kayaking, paddleboarding, fishing, clamming, and swimming, make this an exceptional opportunity. Fully furnished, turn-key, move right in!

56 Stage Island Road, Chatham

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.

$1,599,000

3 Beds ⋅ 3 Baths ⋅ 73519558 MLS

Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully designed for gathering, relaxing, and entertaining, this one-of-a-kind property offers the charm of a custom retreat with the functionality of today’s living. Ideally located close to beaches, shopping and restaurants. With deeded rights to the private beach just steps away, a beautiful landing to launch your kayaks. This is a truly distinctive home with architectural character, inviting spaces, and an unforgettable sense of place. (Moorings should be available on Taylor's Pond with a relatively short waitlist, check with the Harbormaster!)

70 Uncle Deane's Rd, Chatham

Listing courtesy of Listing Agent: Patrick Davison from Listing Office: .

$2,699,000

3 Beds ⋅ 3 Baths ⋅ 73513527 MLS

Stage Island is among the most exclusive addresses on Cape Cod — a private enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, sweeping marsh and water views, breathtaking sunsets, and abundant conservation land define a setting that is truly generational. Marsh-front access invites kayaking and quiet recreation, while wildlife and natural beauty frame everyday life. The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light, anchored by a wall of windows and doors with 270-degree views. The private primary suite offers its own deck and a soaking tub with waterfront views — an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks create multiple zones for alfresco dining, yard games, and summers well spent. A setting this rare does not come twice!

336 Stage Island Rd, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$5,450,000

5 Beds ⋅ 5 Baths ⋅ 73506909 MLS

Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat w/tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for guests. A walk-out lower level expands living space with an entertainment room and full bath. New HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham PLUS deeded rights to a boat house steps away!

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$5,850,000

5 Beds ⋅ 6 Baths ⋅ 73495151 MLS

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham

Listing courtesy of Listing Agent: Timothy Bailey from Listing Office: John C. Ricotta & Associates, Inc..

$4,500,000

6 Beds ⋅ 7 Baths ⋅ 73479712 MLS

Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.

48 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

$2,295,000

3 Beds ⋅ 3 Baths ⋅ 73477537 MLS

Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas FP & wet bar for relaxed moments overlooking koi pond& garden.The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace & skylit seating area, which flows to the tranquil stone patio for outdoor dining, BBQ.1st FL primary suite with sitting room and en suite bath. Plus lower level office 300 Sq ft, 2 car garage, AC, generator, gas heat, irrigation. Seller to install new 3 BED septic & new 2nd FL heating/AC system.. 2026 Frost Fish Crk Restoration project for tidal flow in progress.

41 Court St, Chatham

Listing courtesy of Listing Agent: The Nickerson Power Group from Listing Office: Compass.

$829,000

3 Beds ⋅ 2 Baths ⋅ 73460325 MLS

Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers gleaming hardwood floors throughout and open concept. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural gas and town water in the road, The wood burning fireplace creates ambiance when sitting in the family while relaxing with a good book or watching TV. The yard is filled with beautiful perennials that explode throughout spring and summer. New septic and town water are installed.

33 Duck Marsh Ln, Chatham

Listing courtesy of Listing Agent: Darci Sequin from Listing Office: Gibson Sotheby's International Realty.

$2,800,000

3 Beds ⋅ 2 Baths ⋅ 73457238 MLS

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 spectacular 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.

78 Indian Trail, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$3,200,000

3 Beds ⋅ 3 Baths ⋅ 73457239 MLS

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 on Bucks Creek, 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 Bucks Creek gem has to offer. An abutting property, 78 Indian Trail, is availbale for sale at $2,800,000.

92 Indian Trail, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

$1,650,000

1 Baths ⋅ 73258353 MLS

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!

231 Crowell Road, Chatham

Listing courtesy of Listing Agent: Judith Smith from Listing Office: John C. Ricotta & Associates, Inc..

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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.

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