Chatham Massachusetts Real Estate & Homes For Sale

What's on your wish list? A primary or vacation home that you can walk to downtown Chatham from with its fine dining, shopping and galleries...or to the bike path & pickleball? Look no further! 99 Heritage Ln is only 2/3 mile to Oyster Pond Beach and minutes away from the many beautiful south side beaches. Enjoy this comfortable 3-bedroom home with a large fenced-in backyard.

Discover luxury and comfort in this stunning Riverbay home nestled with beautiful landscaping on Riverbay Drive. This meticulously renovated 7 room ranch offers 2340 sq. ft of elegant living space, featuring 3 spacious bedrooms, including a sunny primary suite, 2.5 baths with double sink vanities.

Three bedroom ranch house in desirable Riverbay Estates. All bedrooms on first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area....

This Quintessential Chatham retreat on picturesque Shore Road exudes timeless charm and sits in close proximity to beautiful beaches and the village. The well maintained home provides a welcoming floor plan with comfortable spaces for gathering, and private rooms for peaceful reflection.

Looking for a project? Opportunity builders/investors to bring your imagination to renovate this nostalgic 1947 Cape style home with 1988 addition enlarging it to 2625 Sq. ft being sold AS IS.

South of 28 Chatham 3BR ranch for sale just 0.3 miles from beautiful Forest Beach on the ocean! Renovated in 2002 with a vaulted ceiling living room addition that doubles as a sunroom & opens to a large dining area that can fit all your guests around a big table. Hardwood floors in all 3 bedrooms, living room/sunroom & dining room.

This gorgeous 5-bedroom lot offers the rare opportunity to create your ideal custom home in a private, tranquil setting--tucked away from the traffic of Chatham's busy main roads. Whether you're looking to build immediately or hold for the future, this prime piece of land is ready for your vision.

Perfectly positioned in one of Chatham's most coveted enclaves--just across from iconic Lighthouse Beach--this classic Cape-style residence offers an exceptional blend of historic charm and modern comfort. Rich in character and beautifully maintained, the home features light-filled, generously scaled rooms that flow effortlessly between formal and informal living spaces.

This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.

Tucked away on a private lane in North Chatham, 25 Menekish Lane offers a rare blend of seclusion and proximity--steps from Cow Yard Beach, Chatham Bars Inn, the Fish Pier, and Main Street.

This commercial lease space is in a prime location in the heart of Chatham's bustling walking district, offering unparalleled visibility. Space is directly across from the Chatham Wayside Inn. Ideal for capturing summer crowds, this front-to-back space includes a private half bath and convenient front and rear entrances. Ample street parking and rear lot space provide additional convenience.

Enjoy your dream Cape vacation destination in this shared-ownership, professionally managed waterfront property in North Chatham. The house features 3 bedrooms and 4 and a half bathrooms with breath taking views of Ryders Cove. Encompassing 3200 sq ft of living space, the property is being offered as shared ownership among five owners (20% share).

This one owner, custom built home, by Cape Cod Associates, was forward thinking and designed in 1981 as a passive solar house. Today it is a fully solar, efficient electric home with solar panels that are owned and create credits throughout the year. The thoughtful floor plan allows for seasonal views of the pond.

Attention Builders and Investors! This 3 BR, 2 Bath Cape boasts curb appeal and a desirable south-of-28 location near Cockle Cove Beach. There is tremendous opportunity to create value. First floor has a kitchen, living room w/FP, adjacent open dining, two bedrooms & bath with double vanity.

This 1.069 acre lot is zoned R20 and partially R60. Great location close to the beach and bike trail. Buyer and their agent to do their own due diligence. Please verify all information contained herein.

Tucked away from the road in desirable Riverbay, this charming ranch offers comfortable living with three bedrooms and two full baths. A standout feature is the spacious one-bedroom ancillary apartment with its own private entrance, a cozy kitchenette, and a fully accessible handicapped bathroom--perfect for guests, extended family, or rental income.

A rare opportunity to own a pond front home in the highly desirable Riverbay Estates. Nestled on the tranquil shores of Pickerel Pond, this beautiful 4-bed, 3-bath home offers breathtaking water views and direct pond access, perfect for kayaking and paddleboarding.

Nestled on just over an acre of meticulously landscaped grounds with a private well for irrigation near the Oyster River, this 4-bedroom, 3.5-bath home offers a rare opportunity to create your dream space. With deeded access to a small, shared boathouse, it provides a serene and sophisticated lifestyle.

Refreshed and Renewed... Don't miss this incredible opportunity to own a property in a prime Chatham location, just a short stroll from downtown. Enjoy nearby conservation hiking trails, the Cape Cod Rail Trail, and tennis courts, all within walking distance. Restaurants, shops, beaches, parks, and schools are also just a half-mile away.

This unrivaled oceanfront estate located on prestigious Ministers Point in North Chatham offers grand scale living with dramatic Atlantic Ocean vistas. The meticulously designed cedar shingle and sprawling stone exteriors seamlessly blend the elegant interiors that boast striking architectural details, custom finishes and the highest quality craftsmanship.

Experience the perfect blend of luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship throughout.

Welcome to 1996 Main Street in the picturesque town of Chatham, MA! This charming 3-bedroom, 2-bathroom ranch style home spans 1,813 square feet and is ready for your vision and creativity. With several essential updates already in place, including a new roof, fresh shingles, and a newer gas heating system, you can focus on adding your personal touch to make this house your dream retreat.

New construction underway with deeded rights to Lover's Lake for swimming, fishing and boating! Classic Cape Cod home sited high on a knoll with over 3000 s.f. spanning three levels with 3 BR's and 4.5 baths. Open floor plan offers great room with vaulted ceilings, fireplace and adjacent kitchen with center breakfast island and high end appliances .

Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwork! This charming 3-bed, 2-bath home is nestled on a 1.8-acre lot, complete with a stunning kettle pond and a lush pastoral backdrop. Renovated in 2014, the home boasts a fresh roof and all the modern comforts.

Discover your dream home just a short stroll to Cockle Cove Beach! Incredible spot...Tucked away at the end of a private lane, this 3 bedroom 2 1/2 bath home with long leaf yellow pine floors throughout the first floor has plenty of living space for family and friends.

Designed by the award-winning architectural firm Polhemus Savery DaSilva, this waterfront masterpiece has been refined with elevated finishes by renowned designer Lisa Tharp.

A truly rare offering on Chatham's iconic Main Street--605 Main Street is an 827 sq. ft. freestanding retail building in one of Cape Cod's most coveted commercial districts. This standalone property commands maximum visibility, ensuring unparalleled exposure amidst the town's exceptional foot traffic.

Set in the desirable Misty Meadow neighborhood, 109 Misty Meadow Unit 2 offers an ideal gateway to the Chatham lifestyle. This ground-floor 1-bedroom, 1-bathroom condominium is a rare find, blending convenience, charm, and investment potential. Whether you're seeking a turnkey rental, seasonal getaway, or an easy-care year-round home, this residence delivers on every front.

Tucked away on a quiet street in the heart of North Chatham, this charming second-floor condominium offers an exceptional opportunity to own in one of the Cape's most coveted locations. Whether you're seeking a seasonal retreat, an investment property, or a smart entry into the Chatham market, this residence delivers a perfect blend of convenience, charm, and value.

Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this charming North Chatham residence, offering three bedrooms and three beautifully remodeled bathrooms. Whether you're looking for a serene getaway or a year-round retreat, this home delivers coastal comfort and modern updates.

In the heart of South Chatham, just moments from Forest Road Beach, this versatile 5-bedroom, 3-bathroom antique home offers endless possibilities. Built in 1834, yet, designed for dual-unit living, the property is perfect for multi-generational families, rental income, or easily converting into a spacious single-family retreat.

TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.

TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.

Nestled above Bumbula ''It's All About Me'', Unit D at 425 Main Street offers an unparalleled lifestyle in the heart of Chatham. This 1-bedroom, 1-bathroom residence blends sophisticated comfort with modern convenience, making it the ideal year-round home or refined retreat. With a private, discreet entrance, this second-floor sanctuary is one of only two residences on this level.

Situated on a quiet cul-de-sac in a desirable neighborhood, this bright Cape enjoys a prime location just a mile from town with several shops & restaurants within walking distance. Encompassing 2,300 sq.

This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborhood, and includes deeded rights to the Oyster Pond River. Immaculate and lightly used, you'll find 4,857 square feet of comfortable, casual elegance in a thoughtfully-designed floor plan. There are 4 spacious bedrooms including a lovely first-floor primary En-suite.

Building lot available! Located at the end of a cul-de-sac and abutting the Town Forest. Water Department has an easement for a road over the property at the edge of the lot boundary. All due diligence required for building allowances and restrictions are responsibility of the buyer.

''On Pink Wink Pond'' embodies the essence of Cape Cod in this remarkable estate. A startling entrance of Belgian blocks with carriage lighted and stone pillars greets the visitor. Ascending a few steps to the farmers porch and upon entry, an illuminated tile mural of Pink Wink Pond establishes this home's attention to artistic detail.

Family-friendly home on Chatham's private Stage Island boasts captivating barrier beach and ocean views. This 10-room, 4-BR, 5.5-bath shingle-style home has 5,372 sf of living space designed for entertaining, indoors and out. The bright and airy 1st floor features a spacious great room with towering windows, a coffered ceiling, and Rumford fireplace.

Three - 2 Bedroom Apartments are included in this Main Street Chatham Mixed Use Property located at 1223 Main Street, Chatham, Cape Cod, MA. Close to the beach, shopping, retail, USPO and much more. The parcel is 41,059 square feet and is improved by a 7,552 square foot building. The first floor has three retail tenants, Cape Shark, Liberty Bakery and Dog Spaw.

Great Investment Opportunity! Highly Visible well established 2,368 sq ft Medical Office Building Complex including a separate 3,344 sq. ft.7 Bay Garage Warehouse & a huge unfinished room above all on 1.2 Acres! There is also an Owners Quarters above the medical building.Multi-Use.

First floor office located in Chatham, a short distance to downtown with easy access to Route 6 and all Lower Cape points. +/- 900 Sq. ft., multiple offices, storage space, and plenty of parking. Front & Rear entrances, central air & gas heat. Full bathroom. Asking $1,350 per month.

Price reduction! Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house or 2 separate houses on this 1 acre lot that backs up to a cranberry bog. The lot has sewer hook up in front of the house. This lot has potential view of the cranberry bog and is very close to Ridgevale beach.

Price reduction! Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house or 2 houses on this 1 acre lot that backs up to a cranberry bog. This lot has potential view of the cranberry bog and is very close to Ridgevale beach.

Take advantage of this last opportunity to build on a vacant lot on Main Street in downtown Chatham! This lot is 7,010 square feet (0.16 acres) located across from Chatham Veterans Field, home of the Chatham Anglers baseball team. This truly is the last opportunity to build on a vacant lot in downtown Chatham.

The 4th of July is less than 6 months away! Here is a rare opportunity to be a stone's throw from Ridgevale Beach with private association access via the Buck's Creek Association bridge. This 2-bedroom cape style cottage is ready for rehab, or a total rebuild. It sits on an elevated bluff and is not in the Flood Zone.

Perched on a bluff in one of Chatham's most coveted locations, Summer Wind is an expanded Cape Cod classic offering the perfect blend of traditional charm and modern amenities. With deeded access to picturesque Ryder's Cove, the luxury of an association beach, and the convenience of deep-water access to Pleasant Bay and the Atlantic beyond.

Sited on a picturesque lane in a coveted North Chatham location, this custom estate home with deeded access to a private sandy beach on Pleasant Bay is being offered fully furnished and turn key!! Featuring the absolute best of coastal Cape Cod living, the 5+ bedroom Main House and 2 bedroom Guest House are like new, having been further improved and maintained to exacting standards.