Houses for Sale in 02633

/73
$8,500,000
- 7 Beds
- 6.5 Baths
- 6,521 Sq Ft
44 Buena Vista Rd, Chatham, MA 02633

Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views,

Shane Masaschi

Compass

(508) 400-2035

44 Buena Vista Rd, Chatham, MA 02633
/68
$2,295,000
- 4 Beds
- 3.5 Baths
- 4,072 Sq Ft
55 Winterset Dr, Chatham, MA 02633

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

Tara Schiffmann Brown

Bayview Real Estate

(508) 388-5284

55 Winterset Dr, Chatham, MA 02633
/69
$4,200,000
- 3 Beds
- 4.5 Baths
- 3,640 Sq Ft
287 Cedar St, Chatham, MA 02633

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island

Shane Masaschi

Compass

(508) 290-5337

287 Cedar St, Chatham, MA 02633
/81
$4,900,000
- 4 Beds
- 4.5 Baths
- 2,850 Sq Ft
346 Morris Island Rd, Chatham, MA 02633

Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vista out to Nantucket Sound and beyond. This four bedroom, 4.5 bath residence blends exquisite taste with timeless coastal elegance. Thoughtfully renovated, the home is designed to showcase wide, sweeping views of the harbor from nearly every room. Light-filled interiors pair refined finishes with a relaxed

Barbara Garside

eXp Realty, LLC

(508) 401-8501

346 Morris Island Rd, Chatham, MA 02633
/24
$5,900,000
- 2 Beds
- 2.5 Baths
- 1,850 Sq Ft
99 Uncle Alberts Drive Extension, Chatham, MA 2633

Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

Shane Masaschi

Compass

(508) 400-2035

99 Uncle Alberts Drive Extension, Chatham, MA 2633
/71
$4,750,000
- 4 Beds
- 5.5 Baths
- 5,372 Sq Ft
335 Stage Island Rd, Chatham, MA 02633

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

Jack Bohman Gibson Sotheby's International Realty

335 Stage Island Rd, Chatham, MA 02633
/76
$4,200,000
- 4 Beds
- 5.5 Baths
- 4,908 Sq Ft
45 Meadow View Rd S, Chatham, MA 02633

New construction and a deeded boat slip in the Oyster River Hills private neighborhood marina. Another magnificent home by Sears Point Residential, move-in ready. 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape. The home's axis is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows seamlessly from the living room to the

Jack Bohman Gibson Sotheby's International Realty

45 Meadow View Rd S, Chatham, MA 02633
/71
$6,695,000
- 5 Beds
- 4.5 Baths
- 3,225 Sq Ft
101 Morris Island Rd, Chatham, MA 02633

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated

Jack Bohman Gibson Sotheby's International Realty

101 Morris Island Rd, Chatham, MA 02633
/35
$4,395,000
- 3 Beds
- 3 Baths
- 2,418 Sq Ft
30 Indian Trail, Chatham, MA 02633

Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal masterpiece nestled in Hardings Beach Hills with panoramic views of the marsh and creek. Blending classic Cape vernacular with modern inspiration, the home is defined by extraordinary craftsmanship and architectural detail. The open main level features a curved fireplace wall with v-groove paneling that flows into

Chris Rhinesmith Compass Massachusetts, LLC

30 Indian Trail, Chatham, MA 02633
/42
$3,500,000
- 3 Beds
- 4.5 Baths
- 3,759 Sq Ft
28 Cranberry Ln, Chatham, MA 02633

Perfectly sited in sought-after North Chatham, this new construction home is a masterwork of coastal design. The entryway sets a refined tone, opening to a great room with shiplapped and coffered ceilings that create balance and elegance. At one end, a clean-lined kitchen boasts custom cabinetry, a striking quartz island, and premium Thermador and Fisher & Paykel appliances. A dining area flows

Chris Rhinesmith Compass

28 Cranberry Ln, Chatham, MA 02633
/27
$3,500,000
- 5 Beds
- 5.5 Baths
- 7,396 Sq Ft
450 Main St, Chatham, MA 02633

Welcome to 450 Main Street! A premier mixed-use investment opportunity in the heart of Chatham, MA, Where Cape Cod charm meets Main Street style. Located in the highly desirable GB2 zoning district, this 7,396 sq ft property offers a compelling blend of residential and retail potential. Featuring five well-appointed apartments with solid rental appeal, along with prime street level retail

Ricardo Rodriguez Team Coldwell Banker Realty

450 Main St, Chatham, MA 02633
/28
$3,895,000
- 4 Beds
- 4 Baths
- 3,000 Sq Ft
17 Bucks Ln, Chatham, MA 02633

This Chatham Beach House is calling...hope you answer.... Picture perfect Cape Cod style home with divine views over Nantucket Sound offers the idyllic Chatham beach lifestyle you have been dreaming of.....Steps to the private association beach of Harding's Shores for uncrowded enjoyment and warm water swimming. Classic 4BR 4 bath Cape home with two large decks for al fresco dining or morning

Lori Fanning Smith Compass

17 Bucks Ln, Chatham, MA 02633
/49
$3,399,000
- 3 Beds
- 4.5 Baths
- 4,361 Sq Ft
86 Champlain Rd, Chatham, MA 02633

Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lighthouse and Nantucket Sound. Savor the warm summer breezes from this 3 BR, 4.5 Bath, 4,361 sf home with a private deeded footpath to the sandy shores of Stage Harbor. Thoughtfully designed to capture harbor and wetland views, the house features vaulted ceilings, an abundance of windows, hardwood floors and an

Jack Bohman Gibson Sotheby's International Realty

86 Champlain Rd, Chatham, MA 02633
/49
$4,750,000
- 4 Beds
- 3.5 Baths
- 3,878 Sq Ft
38 Indian Trail, Chatham, MA 02633

BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views stretching to Nantucket Sound, this extraordinary 1.3-acre Chatham property is a true waterfront sanctuary. Designed to embrace its breathtaking natural surroundings, the home features walls of glass and an expansive wraparound deck that blur the line between indoors and out. Spectacular sunsets create a

Chris Rhinesmith Compass Massachusetts, LLC

38 Indian Trail, Chatham, MA 02633
/53
$3,500,000
- 5 Beds
- 3.5 Baths
- 2,659 Sq Ft
92 Barcliff Ave, Chatham, MA 02633

Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical residence was meticulously restored to perfection in 2002, seamlessly blending its storied heritage with the finest modern luxuries. Nestled in a prime yet private locale, the home's enchanting exterior teases with a glimpse of the lush, secluded garden, a serene oasis framed by a stately pergola. The

Chris Rhinesmith Compass Massachusetts, LLC

92 Barcliff Ave, Chatham, MA 02633
/93
$6,750,000
- 5 Beds
- 5.5 Baths
- 5,620 Sq Ft
15 Windy Hill Way, Chatham, MA 02633

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

Tim Bailey John C Ricotta & Assoc.

15 Windy Hill Way, Chatham, MA 02633
/42
$3,495,000
- 4 Beds
- 3.5 Baths
- 4,857 Sq Ft
36 Moonbeam Ln, Chatham, MA 02633

This expansive Cape with timeless curb appeal is located in an exclusive area just 5 minutes to Town and includes deeded rights to the Oyster Pond River. You’ll enjoy 4,857 square feet of casual elegance in a thoughtfully-designed floor plan. This immaculate home offers 4 spacious BRs including a first-floor primary suite. Sunny granite & stainless kitchen opens to the family room w/fireplace.

Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

36 Moonbeam Ln, Chatham, MA 02633
/61
$2,750,000 Open Sun 11AM - 1PM
- 4 Beds
- 4.5 Baths
- 3,603 Sq Ft
290 Old Comers Rd, Chatham, MA 02633

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

Catherine Baran Berkshire Hathaway HomeServices Robert Paul Properties

290 Old Comers Rd, Chatham, MA 02633
/41
$949,000 Open Sun 1PM - 3PM
- 4 Beds
- 2 Baths
- 1,680 Sq Ft
306 Old Queen Anne Rd, Chatham, MA 02633

Cape Cod living made easy in this beautifully updated 4-bedroom, 2-bathroom Cape nestled in the desirable Great Hill Estates neighborhood, less than a mile from downtown Chatham. Thoughtfully renovated throughout, this home blends modern updates with timeless Cape charm. The inviting floor plan features a bright living area, a well-appointed kitchen with quality finishes, and four comfortable

Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

306 Old Queen Anne Rd, Chatham, MA 02633
/55
$1,650,000 Open Sun 1PM - 2:30PM
- 3 Beds
- 4 Baths
- 2,388 Sq Ft
97 Round Cove Rd, Chatham, MA 02633

Welcome to 97 Round Cove Road, a charming Post and Beam home nestled in the heart of Chatham. Set on an expansive and private lot, this residence offers the perfect blend of elegance and character with three generous floors of living space. Ideal for gatherings, this home features a custom kitchen with granite countertops and a center island perfect for entertaining. This home boasts three

Day - Logan Group Kinlin Grover Compass

97 Round Cove Rd, Chatham, MA 02633
/56
$2,375,000 Open Sat 10AM - 12PM
- 3 Beds
- 4 Baths
- 3,226 Sq Ft
94 Ocean Port Ln, Chatham, MA 02633

Built in 2014, this beautifully designed home offers 3 bedrooms, 4 full baths, and over 3,400 sq. ft. of living space, including a finished basement and a bonus room above the detached garage. Hardwood floors flow throughout the open layout, where you'll find a chef ready kitchen, sun-filled living room with coffered ceilings and gas fireplace. The first floor is completed by a full bath, laundry

Jack Bohman Gibson Sotheby's International Realty

94 Ocean Port Ln, Chatham, MA 02633
/47
$8,500,000
- 4 Beds
- 6 Baths
- 4,717 Sq Ft
246 Stage Island Rd, Chatham, MA 02633

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,

Chris Rhinesmith Compass Massachusetts, LLC

246 Stage Island Rd, Chatham, MA 02633
/61
$2,195,000
- 4 Beds
- 4.5 Baths
- 3,069 Sq Ft
6 Stephen Dr, Chatham, MA 02633

Set in one of Chatham's most desirable neighborhoods, just minutes from Hardings and Ridgevale beaches, this residence stands out for its scale, flexibility, and refined design. Sunlight floods the interiors, where expansive windows frame backyard and cranberry bog views and create a bright, welcoming atmosphere.The layout offers four bedrooms plus a versatile office/bonus room and 4.5 baths,

Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

6 Stephen Dr, Chatham, MA 02633
/30
$1,495,000
- 4 Beds
- 2 Baths
- 1,820 Sq Ft
200 Hardings Beach Rd, Chatham, MA 02633

Located just a short stroll to Hardings Beach and close to many favorite local restaurants and conveniences, this classic Cape style two story cottage offers the option of summer or year-round living as well as a a rental investment opportunity. With 4 bedrooms and 2 full baths, the layout is designed for easy living, with bedrooms on both levels and full baths conveniently located adjacent to

Chris Rhinesmith Compass Massachusetts, LLC

200 Hardings Beach Rd, Chatham, MA 02633
/35
$2,449,000
- 3 Beds
- 2.5 Baths
- 1,999 Sq Ft
32 Gladen Ln, Chatham, MA 02633

Effortlessly blending Cape Cod charm with bohemian chic flair, this 3BR 2.5 bath Cape is a serene coastal hideaway tucked into one of Chatham's most desirable neighborhoods. Just moment to town, Chatham Bars Inn, and beaches, this property offers the best of location, style and potential. Enjoy a laid back casual lifestyle, whether your enjoying coffee on the front patio or hosting your

Lori Fanning Smith Compass Massachusetts, LLC

32 Gladen Ln, Chatham, MA 02633
/35
$1,650,000
- 4 Beds
- 3.5 Baths
- 2,843 Sq Ft
207 Horizon Dr, Chatham, MA 02633

Perched high on a private lot in one of Chatham's most sought-after locations, this stunning residence offers over 2,800 sq. ft. of well-designed living space. Featuring 4 spacious bedrooms and 2.5 baths, the home blends timeless style with modern comfort. Step inside to discover gleaming hardwood floors throughout, two full fireplaces for cozy gathers, and sun-filled rooms that invite

Jacquelyn Casey Shore Road Realty

207 Horizon Dr, Chatham, MA 02633
/68
$9,750,000
- 5 Beds
- 8 Baths
- 6,722 Sq Ft
53 Gristmill Ln, Chatham, MA 02633

Wake up to captivating and shimmering water views from nearly every room in this stunning 5BR, 6 full & 2 half bath Little Mill Pond home. Completely rebuilt with exceptional craftsmanship, it blends custom trim, cabinetry & timeless design. Completely and masterfully rebuilt just a few years ago, this residence blends coastal elegance with modern convenience, all within walking distance to the

Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

53 Gristmill Ln, Chatham, MA 02633
/53
$1,570,000 Open Sat 11AM - 2PM
- 3 Beds
- 2 Baths
- 2,307 Sq Ft
73 Joshua Jethro Rd, Chatham, MA 02633

Located in Chatham's highly sought after Riverbay Estates community, this 3-bedroom, 2-bath, 2,307 sq. ft. home blends classic charm with modern comfort. The farmhouse-style kitchen with newer appliances flows to a spacious living room with fireplace, mudroom, and garage entry. A first-floor bedroom and bath offer flexibility, while a dining room and bright eat-in area open to a sunroom with

Paul Borde Christie's International Real Estate Atlantic Brokerage

73 Joshua Jethro Rd, Chatham, MA 02633
/27
$1,399,000 Open Sat 1PM - 3PM
- 3 Beds
- 2 Baths
- 1,702 Sq Ft
93 Orleans Rd, Chatham, MA 02633

Welcome to the meticulous and delightful 93 Orleans Road Chatham. Enter onto the beautiful herringbone-designed brick walkway leading to a relaxing covered front porch with durable Azek flooring-perfect for enjoying the fresh Cape Cod sunshine and ocean breeze. This single-level home offers a true slice of paradise. Completely updated in 2024, the 3-bedroom, 2-bath residence blends modern comfort

Derek Greene The Greene Realty Group

93 Orleans Rd, Chatham, MA 02633
/46
$1,600,000
- 4 Beds
- 3 Baths
- 2,289 Sq Ft
114 Bucks Creek Rd, Chatham, MA 02633

'Float to the ocean with the tide'' Fish, crab kayak, paddleboard and launch off the private association dock. This glorious landing is only two houses away. Offering four spacious bedrooms (including a new primary with ensuite and double showers) and three full baths, this home is sited on a deep lot affording privacy. Lovingly maintained, this custom built one owner home features beamed

Adeline Harrington Berkshire Hathaway HomeServices Robert Paul Properties

114 Bucks Creek Rd, Chatham, MA 02633
/38
$1,599,000
- 4 Beds
- 2 Baths
- 2,392 Sq Ft
56 Skyline Dr, Chatham, MA 02633

Welcome to a quintessential Cape-Cod lifestyle, this updated home is steps away to one of the prettiest private lakes in Chatham. With deeded rights to Lovers Lake for kayaking, canoeing, swimming & fishing and set back on a gracious lot this 3BR plus home offers privacy and nature at every turn. First floor has granite/stainless kitchen w/ breakfast bar and dining area w/ fireplace, a great room

Janet Stuart Coldwell Banker Realty - Concord

56 Skyline Dr, Chatham, MA 02633
/43
$2,200,000
- 3 Beds
- 2.5 Baths
- 2,510 Sq Ft
55 Christopher Harding Ln, Chatham, MA 02633

Step into coastal elegance in this light-filled home, perfectly nestled in a peaceful neighborhood with deeded access to Oyster Pond. Savor your morning coffee in the sun-drenched four-season room, and take in sunset with your favorite beverage on the second-floor deck, where tranquil views set the scene. Inside, you'll find three spacious bedrooms and 2.5 beautifully designed bathrooms offering

Diane Donahue Gibson Sotheby's International Realty

55 Christopher Harding Ln, Chatham, MA 02633
/35
$8,250,000
- 5 Beds
- 3.5 Baths
- 4,307 Sq Ft
127 Wapoos Trail, Chatham, MA 02633

Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water view residence is a rare treasure offering architectural distinction and an intimate connection to Cape Cod's unspoiled coastal beauty. With panoramic views spanning Stage Harbor to the Atlantic shoreline, the home was thoughtfully designed to embrace its extraordinary setting—inviting nature's ever-changing

Dee Sullivan Christie's International Real Estate Atlantic Brokerage

127 Wapoos Trail, Chatham, MA 02633
/44
$1,050,000
- 2 Beds
- 2 Baths
- 1,504 Sq Ft
24 Chickadee Ln, Chatham, MA 02633

Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River with peeks of the water from the main bedroom, screened porch, and huge patio! Completely updated in '23/'24 with new exterior sheathing, siding, windows, doors, and refinished wood floors. The kitchen boasts new cabinetry, counters, and SS appliances. The bathrooms feature new tile floors, vanities, toilets,

Amy Harbeck Kinlin Grover Compass

24 Chickadee Ln, Chatham, MA 02633
/52
$7,999,000
- 5 Beds
- 4.5 Baths
- 4,305 Sq Ft
30 Tisquantum Rd, Chatham, MA 02633

What. A. View! 180 degree panoramic water vistas over The Atlantic Ocean, Chatham Harbor, and picturesque Stage Harbor set the tone for this shingled style home located high on a hill on private Morris Island. Sweeping ocean views and a private association beach combine with 2.33 acres to create a luxurious yet comfortable coastal retreat located in the Quitnesset Association.

Lori Fanning Smith Compass Massachusetts, LLC

30 Tisquantum Rd, Chatham, MA 02633
/60
$7,299,000
- 4 Beds
- 5 Baths
- 4,214 Sq Ft
12 Pond St, Chatham, MA 02633

Custom Home in Chatham Village. 4-bedroom, 5-bathroom residence located steps from Oyster Pond and its sandy beach. This thoughtful home offers open floor plan, high ceilings, hardwood floors and expansive water views. Deeded access to an association dock and mooring field for boating enthusiasts. The gourmet kitchen features stone countertops, large center island with seating, and premium

Tim Bailey John C Ricotta & Assoc.

12 Pond St, Chatham, MA 02633
/43
$4,200,000
- 6 Beds
- 4 Baths
- 3,808 Sq Ft
150 Barcliff Ave, Chatham, MA 02633

Chatham: where hydrangeas meet the sea and harbors merge into the ocean. A place where cherished memories are created and passed on through generations. If you've been dreaming of living in this storybook town, just a short stroll from sandy beaches and its vibrant Village, you've arrived. Welcome to 150 Barcliff Avenue. Tucked along one of Chatham's most picturesque streets, this updated home

Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

150 Barcliff Ave, Chatham, MA 02633
/29
$1,195,000
- 3 Beds
- 3 Baths
- 2,202 Sq Ft
319 Riverview Dr, Chatham, MA 02633

Sited on nearly an acre of land in Riverbay Estates, this spacious 3 bedroom, 3 bath home offers ample privacy and outdoor living space. Built in 1984 with an addition & updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite with gas fireplace, walk in closet, & outdoor access. The kitchen features abundant cabinet space, a

Chris Rhinesmith Compass Massachusetts, LLC

319 Riverview Dr, Chatham, MA 02633
/29
$2,150,000
- 3 Beds
- 4.5 Baths
- 1,834 Sq Ft
292 Stage Harbor Rd, Chatham, MA 02633

Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to the center of Chatham Village sits this exceptional 3 bedroom 4 bath custom Farmhouse with inviting front porch built in 2018. Hardwood floors thruout and, formal dining area, custom kitchen along with an office for those working remotely. Home has central a/c and a gas stove in the Livingroom. The lower

Ward Brown William Raveis Real Estate & Home Services

292 Stage Harbor Rd, Chatham, MA 02633
/35
$2,150,000
- 4 Beds
- 2 Baths
- 1,238 Sq Ft
213 Main St, Chatham, MA 02633

Location! Location! Nestled In the heart of Chatham historic Old Village district, this 1850 Greek Revival has water views of Chatham harbor, with Lighthouse Beach, Main St shopping & dining, band concerts, golf, all nearby! This charming 4 BED/2 BA home has a sunny eat-in family room, beamed ceiling, with sliders to deck, cozy kitchen adjacent and front living room has gas fireplace & warm

Phyllis Power Compass

213 Main St, Chatham, MA 02633

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