Chatham, MA

Often cloaked in morning fog, Chatham, Massachusetts forms the ragged elbow of Cape Cod.

Encompassing a mere 16 square miles of dry ground, Chatham is a decidedly maritime place of pristine beaches, wild barrier islands, tidal shoals, fleeting sandbars, circular coves and miles of saltwater inlets.

Incorporated in 1712, Chatham remains remarkable old-fashioned, despite a well-deserved reputation for shopping. Chichi boutiques reside in quaint storefronts along its winding Main Street lined with historic inns, white-steepled churches, varied eateries and art galleries. A visit to the busy commercial fishing pier reveals the thriving fishing village that exists beneath Chatham’s stylish façade.

Chatham has a beauty that is unsurpassed. Surrounded on three sides by water, it has expansive and magnificent beaches, abundant marine wildlife, and a community committed to preserving these natural resources for future generations.

The Town of Chatham is investing in its future with a wastewater construction project that addresses nitrogen issues that degrade the water quality of the harbor and estuaries along Chatham shores. This project will help to maintain the excellent water quality of the drinking water supply wells and preserve the valuable fresh water pond resources in the town.

For more information on this project, visit www.chathamscproject.info.  If you would like to learn more about Chatham MA real estate, contact Shoreland Realty Group.  Register with our site to stay up-to-date on your favorite Chatham Massachusetts home listings.  

301 Whidah Road Chatham MA 02650

Chatham, MA301 Whidah Road

Price$14,950,000

Est. Mortgage: $/month

MLS Number 22402425

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 7,259
  • Parking Spaces 5

Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay. Take the stairs to the water and enjoy your own private beach and moor your boat out in front of your home. Designed by renown Salt Architecture, the residence seamlessly blends Cape Cod design with a modern aesthetic elevating seaside living to a level all its own. Using the finest of building materials, attention to detail and the quality of craftsmanship is evident throughout. From the design-inspired interior to the outdoor patio, and heated pool and spa area, nothing is overlooked in this seaside beauty. A tour of the home starts in the front entryway where guests are greeted with striking views of the water, a grand staircase, and a welcoming sitting area. Floor to ceiling windows draw you into the living room that features an exquisitely designed gas fireplace and rock mantel serving as the focal point of the room. On your way to the kitchen, you'll pass an extended wet bar centrally located to the living, dining, kitchen, and patio areas giving the space a friendly indoor/outdoor vibe when entertaining. Walking through this space and approaching the kitchen you'll understand the value of masterful building design. The scale and proportion of the combined kitchen and dining area are perfect as one blends perfectly with the other. A nearby three-season room with gas stove adds another space to enjoy the views and watch the boats go by. Heading from the kitchen towards the side entrance you pass the laundry area, mudroom with cubbies, a half bath, and a door that leads out to a deck where you'll find a BBQ grill area customized for the home. A private primary suite is located on the West side of the home, set apart from the main living areas. This suite has a private office overlooking the water, and a spa-like private bath and its own outdoor shower providing the ideal alfresco experience. The grand staircase is one of the home's focal points and stands as a work of art extending to all 3 levels. An expansive second floor landing greets you at the top of the stairs giving a bird's eye view to the living room below. 3 bedrooms are located on this level, with 2 having spa-like private baths and the other being a fun bunkroom for kids. You'll also discover a comfortable reading nook, laundry and a family room with its own private deck overlooking the pool and having panoramic views of the water and shoreline. The lower level is designed as the ideal recreation space for both adults and children. Here you'll enjoy a nautical themed bar and half-kitchen, exercise room, glass enclosed climate-controlled wine cellar, full bath, a custom-built pool table, and a comfortable entertainment space with a media area, perfect for movie nights. The residence comes complete with a detached 2 car garage with a private suite above having its own bedroom, bath, wet bar, and laundry. With sustainability in mind during the design process, the home features triple glazed doors and windows, Savant Smart System, radiant heat in the bedrooms and baths, all-electric mechanical systems, above code R values with continuous exterior insulation, locally sourced wood flooring and ceilings, a separate well for irrigation, and a generator for Key Systems. With 5 bedrooms, 6.5 baths, spanning over 7,000 SF of living space, and set on 2.18 acres, this home is truly the epitome of coastal living. We encourage a tour through our photo collection to see more of this remarkable residence. A picture is worth a thousand words.

Listed by Doug Grattan of Christie's International Real Estate Atlantic Brokerage

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$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Fairway Drive Chatham MA 02633

Chatham, MA30 Fairway Drive

Price$7,495,000

Est. Mortgage: $/month

MLS Number 22404578

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 6,128
  • Town Chatham

This architectural masterpiece perched above Chatham Seaside Links in a highly coveted Village enclave offers an incredible array of breathtaking vistas with easterly views of Chatham Harbor. The five bedroom home embodies elegant coastal style with showpiece finishes, custom detailing and countless amenities. The foyer with soaring ceilings discloses a great room with grand windows, fireplace, an exquisite kitchen with top-line appliances, extraordinary marble surfaces, and stylish pantry. There is a dining room, first floor ensuite bedroom, mudroom with laundry and half bath. Above the primary suite with a stone clad fireplace exudes elegance and has access to a private balcony and deck for ultimate views and access to a dreamy widow's walk. There are three additional bedrooms and a sumptuous conservatory with luxurious amenities including built-in coffee bar. Arguably one of the most impressive entertainment rooms houses the lower level with a nautically inspired bar with every amenities possible, exercise room , studio, half bath, and laundry -all open harmoniously to the spectacular pool, outdoor kitchen, artisan gardens and magical stone shower.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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150-154 Cross Street Chatham MA 02633

Chatham, MA150-154 Cross Street

Price$7,250,000

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.

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$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Seapine Road Chatham MA 02650

Chatham, MA16 Seapine Road

Price$6,995,000

Est. Mortgage: $/month

MLS Number 22403574

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 6,508
  • Town Chatham

This exceptional custom residence currently under construction is situated in a prime North Chatham location with a nearby association beach. Seamlessly blending comfort and sophistication, the home spans three levels of generous open floor plan spaces and is located on over one acre. The main level interiors flow freely from foyer to a large great room with a living room, dining area and well appointed kitchen. There is a guest bedroom and ensuite bath, office, laundry and mudroom. Above is a luxurious primary suite with views of Crows Pond, Pleasant Bay, the Atlantic and beyond. There are two additional exquisite en-suite bedrooms, laundry and a loft area for entertaining. The lower level accommodates a family room, exercise room and bath. The 4 bedroom main house is complemented by a detached garage with one bedroom guest quarters above. Replete with statement touches throughout, this home is designed for both family life and easy entertaining with a spa-like pool with hot tub. This inviting home is impeccably designed and a rare Chatham find.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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67 Uncle Alberts Drive Chatham MA 02633

Chatham, MA67 Uncle Alberts Drive

Price$4,750,000

Est. Mortgage: $/month

MLS Number 22403761

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 5,578
  • Town Chatham

This impressive home sited on 2.07 acres on a quiet cul-de-sac is just a few minutes away from restaurants, the Chatham bike path and nearby Chatham beaches. The 2014 Eastward Companies home offers a tremendous sense of living space spanning 5,578 square feet and defined by lovely grounds, water views, luxurious finishes and a sweeping open floor plan. The main level flows seamlessly between the entrance hall, beautiful living room, sitting area, a fully equipped kitchen with walk-in pantry, resplendent primary suite with sitting room, mudroom and laundry. Above are three view-filled en suite bedrooms, bonus room and an expansive light-filled family room with fireplace and outdoor living room. The lower level standout feature is an entertainment retreat. This is an outstanding opportunity to own a welcoming retreat for family living and entertaining.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Indian Trail Chatham MA 02633

Chatham, MA30 Indian Trail

Price$4,695,000

Est. Mortgage: $/month

MLS Number 22402957

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,418
  • Town Chatham

Nestled in Hardings Beach Hills, Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, presents a stunning display of nature with its panoramic marsh and creek views. The architecture of this residence is a masterful fusion of classic Cape vernacular with modern inspiration, reflective of PSD's signature style. Unique design elements and extraordinary millwork details, like the curve of the living room fireplace mantle wall with v-groove paneling that extends through to the dining room impart a symmetry and flow throughout the open main level. Views of the marsh, creek and surrounding landscape are offered from every window yet the focus of this extraordinary home is the two story dining room and open reading nook above, illuminated by a dramatic wall of windows overlooking the marsh. The adjoining chef's kitchen offers full amenities and casual bar seating. The main level is complete with a sunny bedroom/study, full bath and multi-use mudroom. The serene primary bedroom has a gas fireplace surrounded by built-in bookshelves and window seat, and the ensuite bath is accented with a custom, stained glass window, designed by the architect, that allows light to pass through from the stair hall - just one of the many special touches. The upstairs guest bedroom has high ceilings and a window niche that can accommodate a table or desk. The walk-out lower level offers additional living space with more views of the marsh and includes a laundry room with abundant storage, built in bookshelves, and plenty of room for family activities. Additionally, the lower level offers adjoining unfinished space if expansion is desired. The stunning marsh and creekfront setting is augmented by mature plantings, natural stonework, generous outdoor deck space and a grilling patio with a picturesque pergola. This coastal home is part of the Bucks Creek Association, which offers a private community picnic area and dock for launching kayaks for leisurely excursions through the marsh and beyond to Nantucket Sound.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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45 Meadow View Road Chatham MA 02633

Chatham, MA45 Meadow View Road

Price$4,495,000

Est. Mortgage: $/month

MLS Number 22403089

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4,908
  • Parking Spaces 4

Deeded rights to a boat slip in the Oyster River Hills Association's private neighborhood marina are just steps away. Custom builder Sears Point Residential has begun constructing a stunning new 4 bedroom, 6 bath, 4,908 sf classic Cape. Move in for the summer of 2025. The axis of the home is defined by a chef's kitchen with a Thermador six burner range, Thermador refrigerator, and additional beverage storage, a large center island with Quartz countertops, an open floor-plan dining and living space with hardwood floors, 9' plus ceilings and custom woodwork throughout. Each bedroom is en-suite with primary bedrooms with soaking tubs on both floors. A den/office, a mudroom, and an oversized one-car garage round things out. There is an additional 1,587 sq ft of basement with high ceilings and deep window wells ready for customization. The irrigated yard is poised for generous outdoor living space and potentially a pool, ideal for entertaining family and friends. The house is fueled by natural gas and on town sewer. Enjoy the close proximity to your own saltwater boat slip, which flows into the Oyster River, Stage Harbor, and Nantucket Sound. Hardings Beach is a short bike ride away.

Listed by The Bohman Hartung Group of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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107 School Street Chatham MA 02633

Chatham, MA107 School Street

Price$4,200,000

Est. Mortgage: $/month

MLS Number 22500042

  • Residential
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4,372
  • Parking Spaces 6

Beautiful, like new condition home built in 2014 by Polhemus, Savery, and Desilva in the very sought after OLD VILLAGE. Close walk to downtown, shopping, restaurants and all that Chatham has to offer..... AND Lighthouse and Water Street beaches are a close 4 minute walk away,....There are 4 large bedrooms, primary en-suites on first and second floors and 5.5 total bathrooms including one off the finished basement rooms.... Living room with built in book cases, large screen TV, windows facing east, west, and south, and a fireplace.... Large chef's kitchen with granite counters and stainless steel appliances. Kitchen island that seats 4 right off the dining room with a table for 8....Views of the Mill Pond from the second floor and a back yard with patio and outside shower... Something for everyone.......

Listed by John B Burke of William Raveis Real Estate & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Jessies Landing Chatham MA 02633

Chatham, MA33 Jessies Landing

Price$3,499,900

Est. Mortgage: $/month

MLS Number 22402528

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,345
  • Parking Spaces 4

A new residence is under way by Eastward Companies. This superbly designed 3,300+ sq. ft. home ticks off most boxes on everyone's wish list; spacious open floor plan, gourmet kitchen with butler's pantry, first floor master suite, and plenty of room for entertaining or hosting overnight guests. Additional notables include a large bonus room with a full bath over the garage, a formal dining room, and a breakfast nook providing additional space for casual gatherings. This home design also includes a first-floor powder and laundry room, 2 additional bedrooms and full bath on the second floor, a 2-car garage and a beautiful in-ground saltwater pool and spa. Completion date is estimated for early spring 2025.

Listed by Doug Grattan of Christie's International Real Estate Atlantic Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Mill Hill Lane Chatham MA 02633

Chatham, MA30 Mill Hill Lane

Price$3,250,000

Est. Mortgage: $/month

MLS Number 22404932

  • Residential
  • Bedrooms 7
  • Bathroom 3
  • Square Feet 2,460
  • Town Chatham

Rare and unique opportunity to own a classic Cape Cod compound in Chatham's iconic Old Village. Tucked at the end of a quiet lane just moments to town, lighthouse and beach. This hide-a-away compound built in 1840 consists of a four bedroom main house, three bedroom guest cottage and a small carriage house currently used as a workshop with a lively history as a neighborhood entertainment venue. While this legacy property has been used as a family vacation residence for generations, it has abundant potential for a creative renovation and enhancement, to be appreciated for generations to come. Steeped with old fashioned charm and classic cottage character like wide board wood floors, original beams and a multitude of wood burning fireplaces, there are so many possibilities to explore. The main house has a painted original wainscoting wood-paneled living room and dining room; both with fireplaces, a kitchen, two full baths, 4 bedrooms above and a lovely screened porch. The intimate three bedroom guest cottage has three small bedrooms and a theatrical double height grand living room with hearth and incredible picture window. Unparalleled, once in a lifetime opportunity.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.93% last updated on Jan 9, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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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 Shoreland Realty are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Shoreland Realty shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated January 12, 2025 11:51 PM EST. All properties are subject to prior sale, changes, or withdrawal.

Shoreland Realty 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.