66 Ethelma Drive is a rare pond front opportunity in Chatham, MA, set along the shores of Emery Pond just minutes from downtown Chatham, Cape Cod beaches, restaurants, shops and close to the bike path. This 4-bedroom, 1-bath home offers 1,547 sq ft on approximately half an acre and presents exceptional potential for renovation, reconstruction, or a custom waterfront build. For buyers seeking waterfront property in Chatham, Cape Cod real estate, or the chance to create a custom home on the pond, this offering is rich with possibility. Enjoy peaceful water views, a serene natural setting, and the kind of privacy and lifestyle that make pond front living so special. Valuable due diligence is already in place, including building plans, engineered plans, ZBA approval, and town sewer is at the road. A unique chance to reimagine and create a signature Chatham retreat in a coveted waterfront setting. Buyer to verify all information and conduct their own due diligence.
This sought after North Chatham location offers 16,117 Sq ft lot with a vintage 1960's, 1375 SF ranch on secluded private lane of " Look Out Hill". Bring your imagination and TLC to make it a wonderful home convenient to Cow Yard Landing or North Chatham amenities, close to town center too...The home has original hardwood floors, a cozy living/dining room with fireplace, a sun room addition with skylights overlooking woodlands & one car garage under. The property is being sold AS IS for new owner to make enhancements as they choose. Title V passed for a 2 bedrooms. R40 zoning, lot is under 20,000 sq. With Board of Health review and variance a new 3 bedroom IA septic system may be possible, with deed restriction: no short term rentals. Information deemed to be accurate but not guaranteed, Buyer and buyer agent to do due diligence for expansion questions. Interesting provenance :Home owned in the 1960's by Award winning American Actress, Shirley Booth " Hazel"TV sitcom 1960's
Tucked within a coveted North Chatham setting of Harbor Coves and offering access to a private association beach, this exceptional Gambrel-style residence currently under construction with Harbor Builders presents a sophisticated coastal retreat.The property offers generous indoor and outdoor living spaces on a half an acre. The main level features an inviting open floor plan where a well-appointed kitchen that flows seamlessly into a spacious great room with living and dining areas. An elegant first floor primary bedroom with en suite bath, laundry, and mudroom complete the first floor. Above, there are two additional luxurious en suite bedrooms. The second level is anchored by a family room with a full bath, office and a versatile loft that provides ideal accommodations for family and guests. The lower level has the opportunity for an entertainment room, exercise space, and full bath, offering additional flexibility. The grounds are equally impressive, featuring a spa-like pool.
Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha’s Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool area. The main living spaces balance comfort and sophistication with warm wood floors, curated finishes, and multiple gathering areas, including a lower level with a glass-enclosed wine room, custom bar, game area, and media lounge. The kitchen features sleek cabinetry, open shelving, and picture windows overlooking the landscape, while bedrooms serve as private retreats complemented by spa-quality baths. Outside, panoramic water views unfold as a private stairway leads to the shoreline. A detached two-car garage with a guest suite above adds flexibility, completing this exceptional offering.
Courtesy: Christie's International Real Estate Atlantic Brokerage
508-228-6000
A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring a chef's kitchen with a butler's pantry, a formal dining room, and a sunlit breakfast nook. The great room is anchored by a gas fireplace, custom built-ins, and striking beamed ceilings, creating a warm and sophisticated gathering space. A first-floor primary suite provides a private retreat, complete with a walk-in closet and its own gas fireplace. Upstairs, two en-suite bedrooms offer comfort and privacy, including a separate suite above the garage and another with a private balcony. A versatile loft with a full bath adds additional living flexibility. The finished lower level is designed for entertaining, featuring a wet bar and full bath. Outdoors, the property is equally impressive with a heated Gunite pool and spa, professionally landscaped grounds with irrigation, and an outdoor shower--perfect for embracing the Cape Cod lifestyle. Additional amenities include a two-car garage, central vacuum, alarm system, and town sewer connection. A rare opportunity to own new construction of this caliber in one of Chatham's most desirable in-town locations.
Ideally situated just moments from Chatham's Village boutiques and restaurants, this exceptional three bedroom,two bath residence captures the essence of Chatham coastal living. Privately set on a private dead-end street, the property offers tranquility and also convenience in one of Chatham's most desirable settings. Thoughtfully designed for effortless single-level living, the main floor features a living room anchored by a wood-burning fireplace, and a charming kitchen with honed countertops that opens seamlessly to the dining area. A sunken entertainment room extends the living space and flows directly to the patio, creating an inviting private oasis. The backyard and outdoor shower complete the quintessential Cape residence. Two highlights include an oversized two-car garage and generous expansion potential on the second floor providing an opportunity to further elevate the home's footprint and value.
Elevated on a .57 acre lot in a serene North Chatham setting within Ryder's Cove Landing Association, this privately situated 3 bedroom, 3.5 bath home offers three levels of living. The main level features an inviting eat-in kitchen with island, a welcoming living room with fireplace, and a three-season sunroom with TV overlooking peaceful surroundings. The primary suite includes a private bath and access to a deck, and a second full bath completes the first floor. Upstairs are two spacious bedrooms, one with an oversized closet and a shared full bath. The finished walkout lower level offers flexibility with a bonus/entertainment room, half bath, mudroom with laundry and a converted garage currently used as a billiards room. Association amenities include a pool, pickleball courts, private saltwater dock, and kayak/paddleboard storage with direct access to Ryder's Cove and Pleasant Bay.
Courtesy: Christie's International Real Estate Atlantic Brokerage
508-228-6000
Welcome to this beautifully crafted residence in Jessie's Landing, an exclusive Eastward Companies development, ideally located just a short walk to Harding's Beach. Set on nearly a half-acre and outside the flood zone, this thoughtfully designed home offers the perfect blend of Cape Cod charm, modern comfort, and peace of mind. The open floor plan is ideal for everyday living and entertaining, featuring an oversized chef's kitchen with a large center island, a dining area, and an inviting living room with a gas fireplace. The main-level primary suite offers a walk-in closet and an elegant bath, along with the convenience of a first-floor laundry. The second level includes two spacious bedrooms, a full bath, and a separate bonus room perfect for guests, a home office, or media space. Outdoor living is exceptional, with an expanded paver patio, custom pergola, mature landscaping, and professionally designed landscape lighting. Additional highlights include a full-house generator, central vacuum, security system with cameras, Hunter Douglas window treatments, and an expansive unfinished basement offering excellent storage and future potential. With its private setting, timeless curb appeal, and turnkey condition, this home offers a rare opportunity to enjoy the very best of Cape Cod living close to beaches, town landing, and local amenities.
Courtesy: Christie's International Real Estate Atlantic Brokerage
508-256-6000
This charming Cape-style home is located in Eastward Point, one of Chatham's most coveted coastal enclaves, near the eastern end of Fox Hill Road. Membership in the homeowners association grants access to private sandy beaches as well as use of a shared deep water dock on Crows Pond - leading to Pleasant Bay and the Atlantic.The thoughtful renovation, performed by Polhemus and Savory, seamlessly blends the classic Cape style charm of the living room and dining room with the contemporary open architecture of the kitchen and family room including tray ceiling, skylight, and bay window which overlooks the deck and gardens.The first floor primary bedroom suite allows easy living on one level, while guests can enjoy staying in the two large bedrooms on the second level.Entering through the front door, buyers will be delighted with the living room's large picture window which captures morning sunlight, as well as a handsome over-sized fireplace. An unfinished area above the attached two car garage offers expansion potential such as a studio or office.With beaches, boating, golf and village shopping near by, this may be the peaceful, charming Chatham home you have dreamed about.
Stunning brand new construction from The Young Companies at 230 Barcliff Ave is well underway and ready for Summer 2026. Architecturally pleasing 4BR 5.5 bath shingled home will offer impeccable details ,finish work, detached two car garage and unbeatable walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn. The 5300 sf home will offer the best new new amenities with a nod to the shingled coastal cottage estates of times past. The open interior as both a welcoming front porch as well as a rear screened porch. The magic continues with high ceilings, centrally located great room with fireplace that opens to a well designed kitchen and adjacent dining room with butler's pantry. A robust primary ensuite , private study and three additional bedrooms grace the second floor. Expansive lower level for use as media room/playroom or gym? You decide! Room for a pool!
Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.
Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the Cape Cod lifestyle. Situated in the sought-after Quitnesset community, this property is perfect for making lasting memories. Step into a the foyer with a stunning double curved staircase, leading to a vaulted living room with a cozy fireplace and a chef's kitchen designed for entertaining. Enjoy casual meals in the breakfast room overlooking a private backyard or host formal gatherings in the dining room. A convenient mudroom and first-floor laundry room makes for easy living. The first-floor primary suite features a walk-in closet and private bath, while the sunroom and wood-paneled den offer peaceful retreats. Upstairs are four guest bedrooms and a charming hideaway accessed by a spiral staircase. A back staircase off the kitchen and two-car garage leads to a large office with expansion potential, while the lower level with a full bath. Deeded Beach Rights.
Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style & includes extra 20,737 Sq ft building lot. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas FP & wet bar for relaxed moments overlooking koi pond& stone walls. The chef's kitchen has granite countertops, a generous 6 seat center island, a cooking fireplace and skylit seating area, which flows to the tranquil stone patio for outdoor dining, BBQ.1st FL primary suite with access to patio, is a private retreat with adjacent sitting room/ home office & a spa- like bath. 2nd FL has 2 large bedrooms &1 bath with large attic ready for expansion. Completing the plan is lower level room, 2 car garage, AC, generator, gas heat, shed, irrigation. Buyer to install new Title V septic
Set within the prestigious Harbor Coves enclave of Oyster Harbors, overlooking Ryders Cove, this spectacular North Chatham waterfront residence offers refined coastal living. A dramatic entry opens to a showstopping living room with cathedral ceilings and walls of glass framing panoramic water views. Light-filled interiors flow seamlessly for entertaining and everyday living. The kitchen features premium appliances, stone countertops, casual dining, and a bar with beverage and wine refrigeration, including Wolf and Sub-Zero, and opens to the patio and gardens. The main level includes a great room with gas fireplace and built-ins, inviting porch, private den, and mudroom with laundry and direct access to the three-car garage. The primary suite offers sweeping water views and a luxurious en-suite bath. Four additional en-suite bedrooms plus a sixth bedroom currently used as an exercise room complete the upper level. Meticulously landscaped grounds complete this rare waterfront offering.
Courtesy: Compass Massachusetts, LLC
508-945-1186
Set on nearly an acre in one of Chatham's most coveted enclaves, this Stage Island residence offers an extraordinary combination of refined craftsmanship and sweeping Stage Harbor views. The welcoming foyer opens to a dramatic living room with walls of glass framing the water, filling the space with natural light. A stylish kitchen with center island and dining area extends to an expansive deck, creating effortless flow between indoors and outdoors. The first floor also features a private ensuite bedroom, cozy den, and laundry area--providing flexibility for both guests and single-level living. Upstairs, three additional ensuite bedrooms include a serene primary suite with panoramic views, a spa-like bath, and spacious walk-in closet. With generous gathering areas and thoughtful details throughout, the home captures the essence of coastal luxury.
Set on nearly an acre with commanding views of Stage Harbor, this Stage Island residence combines timeless elegance with modern comfort. The foyer opens to a dramatic living room framed by expansive windows and a stylish kitchen with an island and dining area that extends to a generous deck—perfect for entertaining. The main level also offers a private ensuite bedroom, den, and laundry. Upstairs are three ensuite bedrooms with walk-in closets, including a harbor-view primary suite with a spa-like bath. The walkout lower level provides a spacious family room, fitness area, mudroom, and powder room. Outdoors, granite walkways, patios, and a built-in marine grill create seamless indoor-outdoor living. With refined craftsmanship, custom finishes, and one of Chatham’s most coveted addresses, this rare offering captures the essence of coastal luxury.
Located in the sought after neighborhood of Countryside Estates. Sitting on a knoll this home offers an open concept with gleaming hardwood floors. The soaring cathedral ceilings in the kitchen and family room makes this home light and bright ! All stainless appliances are almost brand new and the oil tank has just been upgraded to double wall meeting today's regulation. There is natural gas and town water in the road, The wood burning fireplace creates ambiance when sitting in the family while relaxing with a good book or watching TV. The yard is filled with beautiful perennials that explode throughout spring and summer. The septic has been inspected and failed. The seller has contracted for the engineering and permitting for a new septic but the buyer will be responsible for the new septic.Directions: Old Queen Anne Rd to Captain Kendrick. Countryside Dr to Duck Marsh.
NEW CONSTRUCTION - NORTH CHATHAM, 02650. Zillow’s February 2026 data showed just 6 homes for sale in the coveted 02650 North Chatham market, with 50% higher average home values at $1,933,566, compared to 29 homes for sale and a 50% lower average home value of $1,282,193 in 02633. As someone who lives and works in Chatham, I can tell you this kind of difference matters. Buyers at the luxury level are not just purchasing a home. They are investing in location, lifestyle, privacy, and the rare opportunity to own in one of Cape Cod’s most sought-after settings. I’m proud to say I represent one of the 6 homes currently for sale in North Chatham: 83 Old Mail Road. Offered at $3,999,900, this newly built luxury residence offers refined coastal living in a setting that feels both elegant and effortlessly connected to everything that makes Chatham so special.
Courtesy: Compass
508-945-1856
Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated with hardwood throughout, this 3 bedroom, 2.5 bath home offers a comfortable floor plan including a first floor primary ensuite bedroom and 2 large guest bedooms and bath on the second level. In addition to the inviting living room and dining room, adjacent to well apppointed eat-in kitchen, the den with sliders to the deck will be where you'll spend many enjoyable hours relaxing or entertaining. Low maintenance perennial gardens form a delightful border in the backyard surrounding the deck and fire pit. A whole house generator, security system and a water purification system are only a few of the many upgrades that will impress. Close proximity to fresh water ponds, walking trails, south side beaches and downtown Chatham.
Courtesy: The Greene Realty Group
860-560-1006
Riverbay, Chatham... True One Level living with Garage/parking on home level. 8 room custom built ranch with side loading garages, high profile roofline, integrated front porch. Inside, abundant common areas and living space. entrance hallway opens to the living and dining rooms, and two hallways leading to the 3 bedrooms. At the back of the home- 3 additional rooms: a fireplaced family room, an eat-in kitchen with bay window, and a private office. In addition, a walk-in pantry off the kitchen and a main floor laundry room on the main floor. Basement stairs located off the interior garage entry and the exterior side door. The home sits atop a hill, providing curb appeal, excellent drainage and a dry basement. The elevation would be best suited to an AWD vehicle for the occasional snowy day. Outside, there are set down areas in both front and back of the house with total privacy. Back inside, there are wood floors throughout, even in the kitchen. The 2 bathrooms are original, reflected in the price. Most furniture/furnishings convey. New 96% HE gas furnace with AC coil Oct 2020, Certainteed roof March 2022,Garage Door Sept 2022, Hot water heater June 2025.
Professional photos coming soon! Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living.This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted setting within a friendly association that features an association dock on Bucks Creek, complete with kayak storage and a picnic area—ideal for effortless days on the water. The home is enhanced by EV charging station and owned solar, offering exceptional energy efficiency and savings. Thoughtfully designed, light-filled, and meticulously cared for, it is truly a delight to show. Come experience the charm, serenity, and coastal lifestyle this Bucks Creek gem has to offer. An abutting property, 78 Indian Trail, is availbale for sale at $2,800,000.
Professional photos coming soon! Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in spectacular water views and unforgettable sunsets, with private stairs leading down to the water’s edge of Bucks Creek for easy access and serene enjoyment. Inside, the home is a pleasure to show, highlighted by a wonderful sunroom that captures the light and scenery year-round. A rare opportunity to enjoy Chatham living at its best. An abutting property, 92 Indian Trail, is available for $3,200,000.
Co-ownership opportunity. Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a thoughtful floorplan includes 5+ ensuite bedrooms and 3 full floors of living spaces, each accessible by elevator. The large family room features a stone fireplace, window seats, coffered ceilings and direct access to expansive deck overlooking the water. A gorgeous chef's kitchen with 14ft island is the heart of the home with top of the line appliances, Wolf range and a pantry. Spacious primary suite with adjacent octagonal office complements this rare coastal offering. Resort like amenities include a lower level game room, sauna, gym, kitchen, cabana, and heated pool with integrated hot tub.
Nestled above Bumbula “It’s All About Me,” Unit D at 425 Main Street offers a rare blend of privacy, comfort, and true in-town living. One of only two residences on the second floor, it features a discreet private entrance and an open, light-filled layout with recent upgrades, including luxury vinyl flooring and refreshed finishes. The well-appointed kitchen flows into a spacious living and dining area, while the flexible bedroom provides generous storage and year-round functionality. Additional conveniences include a dedicated parking space behind the building and membership in a small, owner-managed four-unit HOA with low fees. Set in the heart of Chatham’s iconic Main Street district, the property offers unmatched walkability to shops, dining, beaches, and year-round attractions. With a low tax rate, strong seasonal economy, and limited inventory, this turnkey unit presents a rare opportunity to secure a refined home in one of New England’s most desirable coastal towns.
** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms—four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room with fireplace, first-floor bedroom currently used as a sitting room, foyer with unique herringbone brick floor, laundry room, plus finished basement. Upstairs, the primary suite offers full bath and three closets, plus two additional bedrooms with full bath. Enjoy picturesque front and back porches, mature plantings, a stone deck, a private back yard with firepit, and space for a swimming pool or tennis court. On the Chatham walking loop, just steps to downtown, Oyster Pond, and Battlefield Landing. Don't miss this exceptional opportunity!
Chatham is located in Massachusetts. Chatham, Massachusetts has a population of 6,554. Chatham is less family-centric than the surrounding county with 11.03% of the households containing married families with children. The county average for households married with children is 19.97%.
The median household income in Chatham, Massachusetts is $88,750. The median household income for the surrounding county is $82,619 compared to the national median of $69,021. The median age of people living in Chatham is 62.5 years.
The average high temperature in July is 77.7 degrees, with an average low temperature in January of 23.4 degrees. The average rainfall is approximately 47.6 inches per year, with 23.2 inches of snow per year.
