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: 6.35% last updated on Sep 5, 2024
* 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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552 Shore Road Chatham MA 02633

Chatham, MA552 Shore Road

Price$13,950,000

Est. Mortgage: $/month

MLS Number 22402778

  • Residential
  • Bedrooms 7
  • Bathroom 7
  • Square Feet 5,868
  • Parking Spaces 8

Situated on a bluff with commanding views over Chatham Harbor, North Beach, and the Atlantic beyond, this extraordinary offering stands as one of the most significant estate properties on exclusive Shore Road. A short stroll from everything Chatham Village has to offer, the property boasts an unprecedented 2.86 acres with rolling lawns, mature landscaping, and a private sandy beach. Mesmerizing views take center stage immediately upon entering the residence, with gracious living spaces and exquisite architectural details. Fit for everyday living and grand entertaining, thoughtful scale and proportions are evidenced throughout. From a large seaside terrace to a secluded deck just above the harbor, numerous outdoor living areas are found across the park-like grounds with ornamental trees and gardens. Set in one of New England's most sought-after waterfront communities, this exceptional estate delivers an unsurpassed lifestyle.

Listed by Paul E Grover and Matthew de Groot of Berkshire Hathaway HomeServices Robert Paul Properties

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$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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23 Oyster Pond Lane Chatham MA 02633

Chatham, MA23 Oyster Pond Lane

Price$12,500,000

Est. Mortgage: $/month

MLS Number 22402360

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,308
  • Parking Spaces 4

Set in the heart of Chatham Village, yet a world apart, 23 Oyster Pond Lane offers an extraordinary lifestyle in one of New England's most sought after communities. Hidden behind tall hedges, a winding driveway gives way to park-like grounds with manicured gardens and mature trees that set the stage for an inimitable seaside estate. Grand and inviting, the five-bedroom colonial residence is ideally perched on a bluff with panoramic views of Oyster Pond and Chatham Village. The interiors artfully balance old world craftsmanship and modern luxury with exquisite attention to detail throughout. At the heart of the home, a gourmet kitchen caters to indoor and outdoor living with French doors that open to a waterside terrace and swimming pool. The well-appointed primary suite is accessed via a private staircase, complete with a walk-in closet, study, and en suite bathroom. At the edge of the lawn, a private dock and boathouse offer endless activities on the water with easy access to Nantucket Sound and the Atlantic Ocean. This magnificent estate is located a short walk from Oyster Pond Beach, Main Street, and everything else Chatham has to offer. Offered furnished for summer enjoyment.

Listed by Paul E Grover and Matthew de Groot of Berkshire Hathaway HomeServices Robert Paul Properties

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$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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178 Queen Anne Road Chatham MA 02633

Chatham, MA178 Queen Anne Road

Price$9,995,000

Est. Mortgage: $/month

MLS Number 22402371

  • Residential
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 7,700
  • Parking Spaces 10

Absolute perfection at this stunning in-town compound featuring commanding water views over Oyster Pond! The result of a multi-year collaboration by top architects, designers and builders, this sophisticated and turn-key coastal offering seamlessly blends classic and contemporary elements to create a one-of-a-kind retreat. Walls of glass overlook expansive lawns and gardens, while sun-drenched living spaces set the stage for large scale entertaining, or relaxed everyday living, alike. Top of the line systems and amenities are found throughout the thoughtfully designed 5 bedroom main house, while a 3 story guest house provides additional accommodations overlooking the beautiful pool and spa. Immediate access to the beach, with a private association dock, and just steps to the restaurants, shops and galleries of Chatham's quintessential Main Street, this exclusive offering is a must see, by appointment only.

Listed by Brian W Dougherty of Corcoran Property Advisors

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$
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$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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: 6.35% last updated on Sep 5, 2024
* 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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326 + 324 Main Street Chatham MA 02633

Chatham, MA326 + 324 Main Street

Price$6,500,000

Est. Mortgage: $/month

MLS Number 22304321

  • Residential
  • Bedrooms 9
  • Bathroom 11
  • Square Feet 6,688
  • Parking Spaces 7

Landmark Main Street Chatham mid-19th century Victorian thoughtfully restored inside and out by renowned architects and builders Polhemus Savory DaSilva. The detailed restoration of this quintessential five bedroom Italianate included a new kitchen, plumbing, electrical system, air conditioning, rebuilding the four and half bathrooms, primary suites on both the first and second floors and outdoor patio with gas fire pit and Admiral Charles Rockwell's iconic eight sided shingled gazebo. In 2010, the Chatham Historical Society honored the work with its prestigious Chatham Preservation Award. This offering also includes an adjacent property highlighted by a renovated barn with a two car garage, extra storage, a gym, large recreation room with a deck and a full bath attached to a thoughtfully renovated four bedroom, 3.5 bath house with an updated kitchen, open floor plan, two en suite bedrooms with private bathrooms, gas fireplaces and screen porches, a home office and ample parking. The grounds are beautifully landscaped. Park your car and explore the nearby harbor, Lighthouse Beach, and Chatham's finest shops and restaurants.

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

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$
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$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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70 Sears Point Lane Chatham MA 02633

Chatham, MA70 Sears Point Lane

Price$6,495,000

Est. Mortgage: $/month

Open House

MLS Number 22404158

  • Residential
  • Next Open House: Thu 09/12 5:00 pm. to 7:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,992

70 Sears Point is a rare legacy property where Cape Cod history meets breathtaking beauty. Set on the bend of Oyster Pond River, and overlooking Stage Harbor, this generational estate offers 270-degree views, including the iconic Stage Harbor Lighthouse and the Atlantic beyond. Designed by Edward Sears Read, grandson of the renowned Willard T. Sears, and completed in 1940, this home harmoniously merges historical sophistication with modern craftsmanship. Antique wood paneling from 1600s Salem, and a nautical-inspired design, with the primary suite positioned like a ship's aft, create a unique treasure. The suite's balcony provides a secluded retreat and perfect perch for panoramic sunsets. The 'wheelhouse' below offers the perfect setting for evening cocktails, while additional living quarters provide space for family or guests. Set on over 200 feet of saltwater frontage with a private sandy beach and licensed dock, the property invites invites you to connect with land and sea in a truly immersive coastal experience. 70 Sears Point is more than a home; it's a generational estate where the quintessential Cape Cod lifestyle can be lived and cherished for yea

Listed by Tony Guthrie and Alfred Schofield of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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372 Fox Hill Road Chatham MA 02633

Chatham, MA372 Fox Hill Road

Price$6,250,000

Est. Mortgage: $/month

MLS Number 22303217

  • Residential
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,214
  • Town Chatham

Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom, two bath waterfront home that feels like a private sanctuary exuding a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining area are view-filled and adjoin a sunroom with a wood burning fireplace, walls of windows and access to a patio. The kitchen has all the amenities as well as a sitting area that opens to a patio with a firepit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat, but can also provide an exceptional palate to create a custom compound or family property for generations to come.

Listed by Chris Rhinesmith of Compass Massachusetts,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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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99 Uncle Alberts Drive Extension Chatham MA 02633

MLS Number 22400763

  • Residential
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,850
  • Town Chatham

My Oyster is a custom-built 2-bedroom, 3-bath house with cherry cabinets, gorgeous trim, hardwood floors, wainscoting, and crown molding, creating a luxurious ambiance of warmth and tranquility. A Dutch oven satisfies culinary desires, and the great room next to the two-car garage can serve as office, gym, or game room. On the bluff, the decks offer 180 degree views of Oyster Pond, Stetsons Cove, and the Oyster River to Nantucket Sound.This historic 1.4-acre waterfront estate, once part of Chatham Bars Inn's farm, has been cherished by the same family for 70+ years. The lot supports the potential for a custom four-bedroom dream home, tennis court, or pool. The Post & Beam barn has water and electricity perfect for a workshop or man cave.Accessible via a scenic driveway, the property offers tranquility, privacy, and timeless charm. It provides direct access to the coastal lifestyle, from water skiing on Oyster Pond to paddling to Nantucket Sound. Close to Chatham's downtown, offering fine dining, boutique shopping, and picturesque streets.This estate is not just land; it's a legacy awaiting new memories and the seaside lifestyle.

Listed by Rick Smith of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.35% last updated on Sep 5, 2024
* 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: 6.35% last updated on Sep 5, 2024
* 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 September 12, 2024 7:53 AM EDT. 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.