Our mobile site is optimized for smaller screens.

TRY IT NO THANKS
MORE SEARCH OPTIONS

      Chatham Luxury Homes

      Search for the latest luxury homes for sale in Chatham, MA. Look through a variety of scenic listings including waterfront and beachfront properties. Buyer Brokers of Cape Cod is your real estate resource for the Cape.

      Save your favorite waterfront homes when you create an account. We will keep you up to date on any property changes or when a similar listing comes on the market. Already have an account with us? Log in here.

      Contact Buyer Brokers of Cape Cod - our team can help answer any questions, set up private showings and provide additional information for any listing below.

      63 Shell Drive Chatham MA 02633

      Chatham, MA63 Shell Drive

      Price$9,999,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22201138

      • Residential
      • Bedrooms 5
      • Bathroom 7
      • Square Feet 6,429
      • Parking Spaces 4

      Waterfront estate with private beach ownership and panoramic Pleasant Bay, Outer Beach and Atlantic Ocean views on 3.47 acres are among the many highlights of this exquisite property. Custom builder Sears Point Residential has begun construction of this 5 BR, 6.5 Bath, 6,205 sf custom home with saltwater swimming pool and hot tub, stunning pool house, and generous outdoor entertaining space. Private stairs lead you to 600' of private beach and a mooring field. The axis of the house is a chef's kitchen with an oversized center island that flows to a central dining space and a living area with a gas fireplace. The house boasts wide plank hardwood floors throughout, 9+ ft ceilings, custom woodwork, a covered porch, study, mudroom, laundry on two floors and a three car garage. Each bedroom is en-suite and there are primary bedrooms with private decks on both the first and second floors. The generous lower level walk-out offers the opportunity for living room, gym, recreation room and wine storage. The third floor Widow's Walk captures the sweeping Pleasant Bay and Atlantic ocean views. Permits are in the works for the buyer to add a custom guest/boat house. Completion spring 2023.

      Listed by Jack D Bohman of Gibson Sotheby's International Realty

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      150-154 Cross Street Chatham MA 02633

      Chatham, MA150-154 Cross Street

      Price$7,600,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22107120

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

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

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

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      95 Tisquantum Road Chatham MA 02633

      Chatham, MA95 Tisquantum Road

      Price$7,500,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22200508

      • Residential
      • Bedrooms 3
      • Bathroom 2
      • Square Feet 1,359

      Available publicly for the first time in nearly 50 years, this coveted family property sits proudly atop a pristine private beach with panoramic ocean and harbor views! The prime one acre parcel with existing cottage is the perfect opportunity for a family looking to build lasting memories in a physically beautiful setting. Enjoy relaxing sea breezes and gorgeous scenery from sunrise to sunset at this exclusive Morris Island sanctuary. Stunning conceptual designs for new home, guesthouse and infinity edge pool by Patrick Ahern Architect. A pleasure to show, by appointment only.

      Listed by Brian W Dougherty of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      52 Tisquantum Road Chatham MA 02633

      Chatham, MA52 Tisquantum Road

      Price$6,995,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22200651

      • Residential
      • Bedrooms 4
      • Bathroom 5
      • Square Feet 4,567

      '' Shambala'' ....Nature and design merge seamlessly in this exquisite contemporary cape home on 2.29 acres. Set on a knoll to take full advantage of the ever changing views over salt marsh ,Stage Harbor and the Atlantic beyond. Custom built in 2016, this Hutker designed home offers 4 Br's, 3 full and 2 half baths, and living space on three levels. A wrap around deck draws you outside to the natural beauty and privacy. The interior offers a refreshing contemporary vibe with open , light filled spaces and a massive fireplace as the focal point of the great room. A chef's kitchen with tremendous views and breakfast island open to a large living room/dining space. A cozy den with access to the screened porch, and guest suite with private bath complete the first floor. Second floor includes a luxurious primary suite with spa like bath with free standing soaking tub , two additional bedrooms and several viewing balconies and decks. A walk out lower level has a media/game room, half bath and additional office space/bunk room. Located on Morris Island, the home includes deeded access to a private sandy beach fronting on Chatham Harbor. Sold furnished ( some excl) Septic is for 5 BR's

      Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      58 Whistler Lane Chatham MA 02633

      Chatham, MA58 Whistler Lane

      Price$5,750,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22201987

      • Residential
      • Bedrooms 4
      • Bathroom 3
      • Square Feet 2,446

      Set in a highly coveted North Chatham location, this charming four-bedroom residence boasts panoramic ocean views and a pristine private beach to enjoy coastal living at its finest. A spacious deck runs the length of the home along the water, with sliding glass doors that seamlessly connect the indoor and outdoor living spaces. Stunning vistas are on full display throughout, while the spacious grounds allow ample space to add a swimming pool or tennis court. Minutes from everything Chatham has to offer, endless opportunities await in an unrivaled setting.

      Listed by Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      177 Cross Street Chatham MA 02633

      Chatham, MA177 Cross Street

      Price$4,995,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22201920

      • Residential
      • Bedrooms 6
      • Bathroom 6
      • Square Feet 4,576

      Originally built in 1838, Hiawatha, located between Chatham Village and Oyster Pond Beach, is meticulously restored top to bottom achieving an elegant combination of comfort and modern coastal sophistication. Clean-lined spaces, wood floors, abundant light and a neutral palette hallmark the flowing interiors and highlight the fine period craftsmanship throughout. Perfect for entertaining, there are 6 bedrooms, 4 full and 2 half baths, 5 woodburning fireplaces, a grand porch, finished space above the detached garage, and stunning bluestone terraced grounds hidden from the road. The focal point of the home is a stately sized living room with a fireplace overlooking the landscape. The well-appointed chef's kitchen has a center island and dining area with a wood burning fireplace, adjoining a formal dining room. Living space is extended to the front of the home with a family room and library both with fireplaces. Two separate staircases lead to the second floor bedrooms. The master suite with fireplace overlooks the home's grounds, with five additional bedrooms and three baths to accommodate everyone's needs. This historic beauty is private, timeless, and a classic Chatham home.

      Listed by Chris Rhinesmith of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      364 Old Harbor Road Chatham MA 02633

      Chatham, MA364 Old Harbor Road

      Price$4,250,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22200549

      • Residential
      • Bedrooms 7
      • Bathroom 8
      • Square Feet 4,279

      Charming New England Luxury meets 21st century living. Take a short stroll over to Cow Yard beach and catch Fish Pier for dinner. The 2021, extensive renovation provides plenty of room for multiple families, summer vacations and cozy winter gatherings. This 4279 sq ft home has an additional expansion option with a garage conversion. The interior design has had no expense spared from the moment you enter. All new custom millwork, paneling, exposed beams, fireplaces, flagstone floors all brought to life with imported fabrics, wallpaper and soft furnishings. The heart of the home is the new farmhouse custom kitchen which spills into the conservatory and the patio beyond with room for a swimming pool. Adjacent is a family room or 1st floor guest room leading to a separate staircase to a beautiful retreat with a private garden. All bedrooms are en-suite. Additional highlights include smart technology, Lutron lighting, professional appliances, heated floors, A/C ultra air quiet system setting each room at your own personal temperature. Oversized laundry room with two washers and professional dryers, irrigation system. Hydrangeas surround this historic home in Chatham.

      Listed by Chris Rhinesmith of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      112 Tisquantum Road Chatham MA 02633

      Chatham, MA112 Tisquantum Road

      Price$3,949,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22106465

      • Residential
      • Bedrooms 5
      • Bathroom 6
      • Square Feet 5,888

      A family compound located on the most southern end of Chatham, this private island location, accessed via a scenic causeway, offers the unbeatable combination of miles of pristine white sandy beaches, woodland walking trails and access to both Chatham and Stage Harbors. For many residents of Morris Island, it's not just a home, it's a lifestyle. Includes deeded rights to 1/2 mile private beach, dog friendly, year round .Custom built by Prestige Homes of Chatham in 2015, this multigenerational Contemporary Cape is a tale of two homes. A 4300 s.f. Main home offering 3BR's plus office and an attached renovated cottage with 1660 s.f with second kitchen, 2BR's, 1.5 baths,loft and living room. A wide hallway transitions between the two residences and has an additional bonus space above for use as a home office / guest overflow. The Main house offers a chef's kitchen with top end Thermador appliances, pantry , breakfast room and granite counter tops. A welcoming living room with gas fireplace and dining space provide room for optimal entertaining. First and second floor bedroom suites offer flexibility. The perfect place to gather family and friends with enough space to work remotely

      Listed by Lori L Fanning Smith of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      517 Stony Hill Road Chatham MA 02650

      Chatham, MA517 Stony Hill Road

      Price$3,795,000The price has recently decreased

      Est. Mortgage: $/month

      Pending

      MLS Number 22200135

      • Residential
      • Bedrooms 4
      • Bathroom 7
      • Square Feet 5,837
      • Parking Spaces 5

      New Construction in Chatham, Move In Spring 2022! Thoughtful 4 bedroom, 6.5 bath, 4,087 sf home on .87 professionally landscaped acres with a 20' by 40' swimming pool and waterfall spa, 300 sf pool house and a 1,450 sf finished basement with a full bath. Ideally located just 1.5 miles from Chatham's acclaimed downtown shops and restaurants and in a neighborhood with three nearby beaches and wonderfully conducive to walking, jogging and biking. Longtime custom builder Webb Place Development has seamlessly blended classic Farmhouse design style with innovative touches. The chef's kitchen with a large island, Quartz countertops and professional series Thermador appliances anchors the open living plan. Other first floor highlights include a family room with gas fireplace, dining room, en suite bedroom, study, screen porch, mudroom, deck, outdoor shower, attached garage and a generator. The second floor includes the primary bedroom suite, two additional guest rooms, a large bonus room with adjacent full bathroom and laundry room. The basement has two large finished rooms with full sized windows and ample storage.

      Listed by Jack D Bohman of Gibson Sotheby's International Realty

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      26 Cross Street Chatham MA 02633

      Chatham, MA26 Cross Street

      Price$3,795,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22201281

      • Residential
      • Bedrooms 4
      • Bathroom 5
      • Square Feet 4,136

      Within steps to Chatham Village, this exquisite residence built by Polhemus Savery DaSilva Architects Builders in 2017 is a showcase offering. The open layout and impeccably finished interiors are perfect for both large scale and intimate family gatherings. The fully equipped kitchen with grand center island opens to an expansive dining area with outdoor patio access and is flanked by a living room and family room both with gas fireplaces. There is a first floor en-suite bedroom with three en-suite bedrooms upstairs and a comfortable sitting area. The master suite is a private retreat and exudes charm with beamed ceiling and a cozy fireplace. With approx 2,000 square feet of unfinished space in the lower level, there is the option to expand. The property is a Cross Street Landing condominium by structure and accessed by a private driveway that leads to the two car garage. With close access to Oyster Pond Beach and all the Village amenities, this pristine home is a very unique in-town find.

      Listed by Chris Rhinesmith of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      24 North Skyline Drive Chatham MA 02633

      Chatham, MA24 North Skyline Drive

      Price$3,450,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22201950

      • Residential
      • Bedrooms 4
      • Bathroom 4
      • Square Feet 4,500

      From the moment you walk into this stunning 4,500 sq. ft. Chatham home the only thing you can say is WOW! High above Great Hills Estates with views of Lovers Lake, White Pond and distant ocean view. This home offers 4 spacious bedrooms (5 bedroom septic- town approved) 2 are primary bedrooms, 4 bathrooms, ( 2 of which have been newly appointed) beautiful gourmet cook's kitchen with spectacular center island, granite countertops and new appliances. Also, 2 gas fireplaces, one in the inviting sunlit living room and the other fireplace in finished bright and airy walkout media / entertainment basement. Great space for that busy family life! This home also offers formal Living Room, a Study and views from just about every room.Perfection abounds from not only inside but the beatifically manicured grounds with new decks, new roof, outdoor shower. Other highlights include new AC, security system, central vac, 2 car attached garage. This home epitomizes THE CAPE COD DREAM !

      Listed by Nancy E Griffin of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      16 Nameless Lane Chatham MA 02633

      Chatham, MA16 Nameless Lane

      Price$3,295,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 22202006

      • Residential
      • Bedrooms 3
      • Bathroom 4
      • Square Feet 3,662
      • Parking Spaces 3

      Tucked within a quiet enclave in the heart of Chatham Village, this pristine home designed and built by Polhemus Savery DaSilva Architects Builders offers a combination of casual open concept design with a contemporary coastal sophistication. Arranged on three levels, the main floor is open and airy with beautiful custom finishes. The well-appointed chef's kitchen offers top of the line appliances, eat-in dining, ample storage and pantry space, bar service, laundry, and a peninsula that welcomes an inviting great room with a gas fireplace as well as french doors accessing a blue stone patio. To the left and right is a dining room and family room/home office with a nearby half bath. Above, the primary bedroom features a walk-in closet, adjacent stackable laundry, custom bureau built-ins and a sleek bath. Two additional bedrooms and a shared double vanity bath complete this level. The lower floor houses a gym, full bath and bonus room and walks out to the two car garage with storage and utility rooms.The private backyard oasis has been immaculately landscaped with terracing and stonework and is just a stone's throw to dining, shops and three nearby beaches.

      Listed by Chris Rhinesmith of Compass Massachusetts,LLC

      {$office->Name}

      Buyers Brokers of Cape Cod, McKenna Associates
      116 Route 6A
      Sandwich MA, 02563
      Office: 774-994-1900

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule TourAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 5.3% last updated on 2022-05-12

      This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

      broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Buyer Brokers of Cape Cod are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Buyer Brokers of Cape Cod shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

      This site was last updated May 19, 2022. All properties are subject to prior sale, changes, or withdrawal.

      Buyer Brokers of Cape Cod has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.

      Testimonials

      “It is certainly not a difficult task in referring Buyer Brokers of Cape Cod, McKenna Associates to anyone who is looking for a home here on the Cape. You are such a class act!”   

      Open Houses

      TIME TO TAKE A LOOK

      Browse the open house schedule today.

      View
      Blog

      STAY CURRENT

      Read about local area info.

      View