Chatham, MA Homes for Sale with Basement

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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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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  /38

  $1,549,000

  • 3 Beds
  • 3.5 Baths
  • 3,050 Sq Ft

  46 Juniper Ln W, Chatham, MA 02659

  ''Moongazer'' represents a rare opportunity to purchase a thoughtfully updated, proven income producing property with deeded access to Taylor's Pond where it is a fun and easy kayak or paddle board out to Nantucket Sound and the beach. This 3,150 sf home offers far more living space and room for overflow guests than meets the eye. Upon entering, you will be wowed by the soaring ceilings,

  The Bohman Hartung Group Gibson Sotheby's International Realty

  46 Juniper Ln W, Chatham, MA 02659
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  /21

  $895,000

  • 3 Beds
  • 2 Baths
  • 1,726 Sq Ft

  144 Lakeview Ave, Chatham, MA 02633

  Three bedroom ranch house with two car garage in desirable Riverbay Estates. All bedrooms on the first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area...Brokers and buyers are

  John Burke William Raveis Chatham

  144 Lakeview Ave, Chatham, MA 02633
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  /37

  $4,400,000

  • 3 Beds
  • 3.5 Baths
  • 2,998 Sq Ft

  85 Main St, Chatham, MA 02633

  OFFERED FULLY FURNISHED INCLUDING ALL CONTENTS SO YOU CAN MOVE RIGHT IN! Ideally situated in one of Chatham’s most sought-after enclaves, just steps from iconic Lighthouse Beach, this exceptional home is rich in character and timeless charm. Beautifully maintained, it offers sun-filled, spacious interiors that transition seamlessly between formal elegance and casual comfort. The thoughtfully

  Chris Rhinesmith Compass

  85 Main St, Chatham, MA 02633
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  /58

  $1,750,000

  • 4 Beds
  • 3 Baths
  • 1,990 Sq Ft

  235 Training Field Rd, Chatham, MA 02633

  NEED AN IN-LAW APARTMENT? Tucked away from the road in desirable Riverbay, this comfortable ranch offers easy living with three bedrooms and two full baths. A standout feature is the spacious one-bedroom apartment with its own private entry, a cozy kitchenette, and a fully accessible handicapped bathroom--perfect for guests, extended family, or rental income.The home features a fireplaced living

  Keith Bradley Gibson Sotheby's International Realty

  235 Training Field Rd, Chatham, MA 02633
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  /49

  $1,400,000

  • 4 Beds
  • 3 Baths
  • 2,391 Sq Ft

  68 Chippingstone Rd, Chatham, MA 02633

  Welcome to Riverbay Estates, where year-round living meets the perfect Cape Cod escape! This inviting 4-bedroom, 3-bath home offers water views and direct access to Pickerel Pond, making it an ideal spot for kayaking, paddleboarding, or simply enjoying the natural surroundings. The main level features a desirable first-floor primary suite, while the spacious living and dining areas showcase

  Marcia Thorngate Smith Christie's International Real Estate Atlantic Brokerage

  68 Chippingstone Rd, Chatham, MA 02633
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  /38

  $6,500,000

  • 5 Beds
  • 6.5 Baths
  • 5,143 Sq Ft

  4 Ministers Ln, North Chatham, MA 02650

  MAJESTIC SEASIDE LIVING. This unrivaled oceanfront estate located on prestigious Ministers Point in North Chatham offers grand scale living with dramatic Atlantic Ocean vistas. The meticulously designed cedar shingle and sprawling stone exteriors seamlessly blend the elegant interiors that boast striking architectural details, custom finishes and the highest quality craftsmanship. The 11 rooms

  Chris Rhinesmith Compass Massachusetts, LLC

  4 Ministers Ln, North Chatham, MA 02650
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  /47

  $1,650,000

  • 3 Beds
  • 2.5 Baths
  • 2,430 Sq Ft

  70 Lantern Ln, South Chatham, MA 02659

  Discover your dream home just a short stroll to Cockle Cove Beach! Incredible spot...Tucked away at the end of a private lane, this 3 bedroom 2 1/2 bath home with long leaf yellow pine floors throughout the first floor has plenty of living space for family and friends. Surrounded by an expansive wrap-around deck, the open concept first floor is highlighted by the living room with wood burning

  Judith Smith John C Ricotta & Assoc.

  70 Lantern Ln, South Chatham, MA 02659
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  /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
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  /32

  $1,469,000

  • 5 Beds
  • 10 Baths
  • 11,000 Sq Ft

  558 Fox Hill Rd, Chatham, MA 02633

  New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and

  John DePreaux Corcoran Property Advisors

  558 Fox Hill Rd, Chatham, MA 02633
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  /42

  $1,995,000

  • 1 Bed
  • 1.5 Baths
  • 1,479 Sq Ft

  409 Main St, Chatham, MA 02633

  Location-Location-409 Main St. in Downtown Chatham offers you this very rare and desirable combination of a mixed use building with a 1st floor highly visible commercial space with showcase windows, maximum retail exposure and high foot traffic, as well as a fully renovated spacious apartment on the 2nd floor in the heart of Chatham Village. The property offers 5 private in-town parking spaces

  Rick Smith Gibson Sotheby's International Realty

  409 Main St, Chatham, MA 02633
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  /27

  $1,750,000

  • 1 Bath
  • 2,586 Sq Ft

  231 Crowell Rd, Chatham, MA 2633

  Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

  Judith Smith John C. Ricotta & Associates, Inc.

  231 Crowell Rd, Chatham, MA 2633
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  /43

  $1,850,000

  • 6 Beds
  • 4.5 Baths
  • 2,665 Sq Ft

  14 Squanto Dr, Chatham, MA 02633

  Perched high above the Oyster River with stunning water views and deeded river access for your paddling and boating adventures, 14 Squanto Drive is your new Chatham beach oasis. Offering a relaxed coastal lifestyle, this home boasts open sight lines, sundrenched living spaces, ideal flow for indoor/outdoor entertaining, and an abundance of room for extended families and guests. From sunrise to

  Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

  14 Squanto Dr, Chatham, MA 02633
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  /34

  $7,250,000

  • 10 Beds
  • 10 Baths
  • 8,000 Sq Ft

  150 Cross St, Chatham, MA 02633

  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

  John Ricotta John C Ricotta & Assoc.

  150 Cross St, Chatham, MA 02633
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  /2

  $6,995,000

  • 5 Beds
  • 7 Baths
  • 5,700 Sq Ft

  13 Captain Knowles Way, Chatham, MA 02633

  Experience luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship. Designed for both comfort and entertaining, it offers five spacious bedrooms, each

  Mina O'Keefe Gibson Sotheby's International Realty

  13 Captain Knowles Way, Chatham, MA 02633
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  /10

  $4,399,000 New Construction

  • 4 Beds
  • 6 Baths
  • 5,800 Sq Ft

  230 Barcliff Ave, Chatham, MA 02633

  Stunning brand new construction from The Young Companies at 230 Barcliff Avenue is underway...Architecturally pleasing 4BR 6 bath shingled home will offer impeccable details , finish work and fabulous walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn Resort. The 5800 sf home will offer the best in new amenities with a

  Lori Fanning Smith Compass Massachusetts, LLC

  230 Barcliff Ave, Chatham, MA 02633
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  /31

  $5,295,000 New Construction

  • 4 Beds
  • 6 Baths
  • 4,989 Sq Ft

  14 Pond View Ln, Chatham, MA 02633

  Sears Point Development presents another breathtaking home that could be your new year-round residence or the perfect summer escape for 2026. With panoramic water views of the Oyster Pond and Oyster River and deeded access to the Oyster Pond with mooring potential, this stunning Nantucket-style home boasts 4,989 sf of thoughtfully designed living space, featuring 4 BR and 4/2 Baths on town sewer.

  Jack Bohman Gibson Sotheby's International Realty

  14 Pond View Ln, Chatham, MA 02633
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  $2,195,000 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 4.5 Baths
  • 3,310 Sq Ft

  98 Horizon Dr, Chatham, MA 02633

  A new construction and a great value in Chatham with deeded rights to Lover's Lake for swimming, fishing and boating and room for a future pool. Classic Cape Cod home sited high on Great Hills Estates with over 3000 s.f. with 3 BR's and 4.5 baths. Open floor plan offers great room with vaulted ceilings, fireplace and adjacent cook's kitchen with center breakfast island and high end

  Lori Fanning Smith Compass Massachusetts, LLC

  98 Horizon Dr, Chatham, MA 02633
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  /18

  $799,900 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,356 Sq Ft

  58 Sugar Hill Dr, Harwich, MA 02645

  Elevated site with views of Monomoy River and deeded access for fishing and launching canoes and kayaks out to Pleasant Bay. 2 bedroom, 2 bath ranch with full basement and garage under. Renovated kitchen with granite countertops, custom made stained glass window, living room with natural gas fireplace, and year round sun room overlooking the river. Walk-up finished attic. High end dehumidifier,

  Daniel Michael Main Street Realty

  58 Sugar Hill Dr, Harwich, MA 02645

Showing Results 41 - 65, Page 2 of 2