Chatham Real Estate

Welcome to Chatham, Massachusetts – a charming coastal gem nestled in the heart of Cape Cod. Renowned for its picturesque landscapes and vibrant community, Chatham offers a unique blend of classic New England charm and modern amenities. With its stunning beaches, quaint downtown area, and rich maritime history, this idyllic town is a perfect destination for both residents and visitors alike.

Chatham is bordered by the Atlantic Ocean, providing residents with breathtaking ocean views and an array of recreational activities. Spend your days basking on the sandy shores of Lighthouse Beach or explore the scenic trails at Monomoy National Wildlife Refuge, where you can spot diverse wildlife and enjoy the tranquility of nature. The town’s historic lighthouse, built in 1808, stands as a beacon of the area’s storied past and is a must-visit landmark.

Downtown Chatham is brimming with delightful shops, art galleries, and gourmet restaurants, offering a taste of the local culture and cuisine. Whether you’re indulging in fresh seafood at a waterfront eatery or browsing unique boutiques, the vibrant atmosphere is sure to enchant you.

Chatham also boasts a strong sense of community, with numerous events and festivals throughout the year that celebrate local traditions and bring residents together. From summer concerts on the green to the beloved Chatham Fish Pier, there’s always something happening in this lively town.

Whether you’re looking for a seasonal getaway or a permanent residence, Chatham, MA, offers an unparalleled quality of life that captures the essence of Cape Cod living. Come experience the charm of Chatham – where coastal beauty meets a warm, welcoming community.

Newest Listings in Chatham

$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

$695,000

2 Beds ⋅ 1 Baths ⋅ 22603438 MLS

Nestled on a private lane in one of Chatham's most sought after locations, this home has been enjoyed by the same family since 1946 and occupied as a year round home for 40 years. This is a rare opportunity to create your own Cape Cod retreat just moments from Oyster River, the Oyster River Boatyard, and nearby Hardings Beach. Bring your vision to the charming, light-filled home full of original character, vaulted ceilings and ready for its next chapter. Whether you're dreaming of restoring its vintage charm or exploring future possibilities, this is a rare chance to own in Chatham. The property is being sold AS IS. Buyers should anticipate the need for a new Title V septic system and replacement of the existing oil tank to meet current town requirements. All information contained herein is deemed reliable but is not guaranteed. Buyers & buyers agents should perform their own due diligence regarding future use and development potential and independently verify all information.

40 Uncle Abner's Path, 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

$468,000

2 Beds ⋅ 2 Baths ⋅ 22603405 MLS

Beautifully remodeled in 2023, this charming 2 bedroom, 1.5 bath Seasonal Cottage is just 0.8 miles from Hardings Beach . Thoughtfully updated and move-in ready, it features a private deck, spacious patio and outdoor shower; perfect for enjoying the Cape lifestyle. Ideally located just minutes from Chatham's acclaimed restaurants, boutiques, and beaches, this turnkey property baosts strong rental history, making it an execptional opportunity!

19 Captain Richards Way, 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

$2,750,000

22603371 MLS

Exceptional investment opportunity in the heart of downtown Chatham. This well-maintained, recently updated 1,920+/- SF freestanding commercial building sits on a prominent 0.63-acre parcel with ample on-site parking. Offered for sale is the real estate only; the property is fully leased to CODO Mexican Kitchen, a well-established and thriving restaurant with a long-term lease in place, providing stable cash flow for investors. The property's prime Main Street location offers outstanding visibility, strong pedestrian and vehicle traffic, and convenient access to Chatham's shops, galleries, beaches, and year-round attractions. The combination of a quality tenant, long-term lease, recent building updates, and one of Cape Cod's most desirable commercial locations makes this a rare opportunity for investors seeking a low-maintenance, income-producing asset in a premier market.Connected to Municipal sewer. 32 parking spaces.

859 Main Street, Chatham

$1,469,000

5 Beds ⋅ 10 Baths ⋅ 22603353 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 classic shingle-style exterior includes a two-car garage and private boat dock with direct water access. The airy living room features a stone fireplace, window seats, and vast water views. The kitchen continues the view with a Wolf gas range, a large island, and doors opening to a deck overlooking Crows Pond. A formal dining room with raised panel walls and a butler's pantry with wet bar completes the main level. The three-level layout includes a quiet office, lower-level gym, indoor sauna, and a guest suite with its own kitchen and living room, all connected by an elevator. A pool, patio, and private dock anchor the outdoor spaces, with sunrise and sunset views from multiple balconies. Lighthouse Beach is close by, and Chatham's Main Street offers galleries, restaurants, and shops. Professionally managed by Pacaso and ready when owners arrive.

558 Fox Hill Road, Chatham

$1,800

22603315 MLS

Legendary Shop Ahoy Plaza - a well-known locallandmark● Excellent visibility on busy Route 28● Positioned between the two Chatham rotaries -maximum exposure and accessibility● Great signage potential to capture drive-by attention● Large storefront display windows - ideal for retailvisibility and merchandisingFront and rear egress - easy access for customers anddeliveries● Oversized storage area below● On-site parking - convenient for staff and patrons● Half bath● HVAC - forced hot air and air conditioning● Municipal sewer● Sprinklered and fire alarm systemRent is per month plus Utilities and Fees.

1589 Main Street, Chatham

$1,495,000

2 Beds ⋅ 4 Baths ⋅ 22603300 MLS

Live in the heart of Chatham at 739 Main street, where shops and restaurants, a movie theatre, Chatham Anglers ball games, concerts, Oyster Pond, and more are just outside your door step! This luxury condominium residence is like-new and ready for immediate enjoyment. An open-concept floor plan on the first level includes a gorgeous granite and stainless kitchen, adjacent dining area, and comfortable living room. A French door opens to a 15 x 10 deck for outside relaxation. Upstairs there are two en-suite bedrooms - each with peeks of the water and a lovely private bath. The walk-out lower level provides additional living space/family room plus full bath, perfect for overflow. Amenities include a one-car garage, 1/2 bath, and 2nd floor laundry. Reasonable condo fees that include outside maintenance allow you to relax and enjoy your Chatham time. Don't miss this very special offering in a prime, walkable location!

739 Main Street, Chatham

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