Chatham, MA Homes

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  /50

  $1,775,000 Sold Aug 27, 2025

  • 3,404 Sq Ft
  • $521/SF
  • 57 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  331 Riverview Dr, Chatham, MA 02633

  Discover this stunning Riverbay residence remodeled to perfection. Boasting unique design elements such as shiplap and extensive moldings throughout, including soaring ceilings and a serene backyard. This turnkey three-level home with an expansive farmer's porch and an oversized two-car garage has everything you need and more. Step inside to find a chef's kitchen that will inspire your culinary

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  331 Riverview Dr, Chatham, MA 02633
• 

  

  

  /78

  Est $3,540,964 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,048 Sq Ft

  155 Inlet Rd, Chatham, MA 02633

  155 Inlet Rd, Chatham, MA 02633
• 

  

  

  /49

  $3,200,000

  • 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
• 

  

  

  /58

  $1,244,000 Sold Aug 26, 2025

  • 3,080 Sq Ft
  • $404/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  21 Gramps Way, South Chatham, MA 02659

  A REAL GEM - Only 2 owners have had the privilege of calling this property home since it was custom built in 1987. Don't miss your chance to be the 3rd owner! Lovingly maintained throughout the years, recent updates include kitchen, bathrooms, windows and a large finished basement. One floor living at its finest. There are 3 generous bedrooms, including a primary bedroom with private bath, 2nd

  Cheryle Young Today Real Estate

  21 Gramps Way, South Chatham, MA 02659
• 

  

  

  /40

  Est $3,809,314 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,915 Sq Ft

  98 Attucks Trail, Chatham, MA 02633

  98 Attucks Trail, Chatham, MA 02633
• 

  

  /42

  $1,225,000

  • 3 Beds
  • 2.5 Baths
  • 1,942 Sq Ft

  597 Orleans Rd, North Chatham, MA 02650

  Set on over an acre and a half of beautifully landscaped grounds, this 3-bedroom contemporary home is flooded w/natural light and offers stunning water views, a flexible floor plan and impressive finishes.The welcoming living room offers walls of windows, cathedral ceilings, a focal fireplace and skylights. A white chef’s kitchen has granite counters, stainless appliances and is open to the

  Cape Cod Power of Two Compass

  597 Orleans Rd, North Chatham, MA 02650
• 

  

  /16

  $830,000 Sold Aug 22, 2025

  • 1,810 Sq Ft
  • $459/SF
  • 3 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1955

  131 Forest Beach Rd, South Chatham, MA 02659

  Fabulous 4 Bedroom home within a short walk to Forest and Nantucket Sound beaches. Has been in the family since new in 1955... Oversized lot for all backyard activities and games...Town Tennis court just a block away.... Bedrooms on both first and second floors for easy access...Midway between Chatham and Harwich Port centers for restaurants, shopping, golf and everything Cape Cod has to

  John Burke William Raveis Real Estate & Home Services

  131 Forest Beach Rd, South Chatham, MA 02659
• 

  

  /69

  Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 5,619 Sq Ft

  513 Stage Harbor Rd, Chatham, MA 02633

  513 Stage Harbor 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
• 

  

  /42

  $1,050,000 Sold Aug 21, 2025

  • 1,636 Sq Ft
  • $642/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  31 Joshua Jethro Rd, Chatham, MA 02633

  NEW PRICECasual living describes this charming 3 Bedroom, 2 Full Bath, 1-car garage under Ranch-style home in lovely Riverbay Estates. Set back from the road on a slight rise, this .47 acre lot abounds with privacy as backyard is completely enclosed by stockade fencing concealed with lovely trees and shrubbery. Relaxing couldn't be easier on the deck right off the kitchen which overlooks a

  Julie Chapin William Raveis Real Estate & Home Services

  31 Joshua Jethro Rd, Chatham, MA 02633
• 

  

  /38

  Est $3,219,202 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,199 Sq Ft

  137 Strong Island Rd, Chatham, MA 02633

  137 Strong Island Rd, 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
• 

  

  /11

  $345,000 Sold Aug 15, 2025

  • 604 Sq Ft
  • $571/SF
  • 1 Day On Market

  • 1 Bed
  • 1 Bath
  • Built 1985

  281 Orleans Rd Unit 5, Chatham, MA 02633

  Great location for this afordable 1 bdr condo! Many amenities within walking distance. Chatham Perk, the Fish Pier, Chatham Seaside Links, Chatham Bars Inn and Chatham Works. Close to downtown with shopping and dinning. Now is a great time to come be a part of the Chatham community!

  Isaac Sargent Compass Massachusetts, LLC

  281 Orleans Rd Unit 5, Chatham, MA 02633
• 

  

  /84

  Est $5,020,171 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,142 Sq Ft

  146 Strong Island Rd, Chatham, MA 02633

  146 Strong Island Rd, 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
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  /44

  $1,520,000 Sold Aug 15, 2025

  • 3,027 Sq Ft
  • $502/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  457 Training Field Rd, Chatham, MA 02633

  This stunning and professionally landscaped Cape-style home offers the perfect blend of comfort and amenities in a private setting. This impressive residence offers 3.024 square feet of living space on a generous 22,651 square foot lot and lovely oak hardwood floors. The front foyer leads into a spacious living room with custom built-ins & gas fireplace. A cozy den with built-ins provides a quiet

  Shane Masaschi Compass

  457 Training Field Rd, Chatham, MA 02633
• 

  

  /25

  Est $4,011,802 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,514 Sq Ft

  192 Eastward Rd, Chatham, MA 02633

  192 Eastward Rd, 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
• 

  

  /41

  $1,599,000 Sold Aug 15, 2025

  • 2,344 Sq Ft
  • $682/SF
  • 2 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1930

  751 Crowell Rd, North Chatham, MA 02650

  Looking for a Chatham retreat you can enjoy from day one that also includes a delightful cottage ideal for in-laws, friends, or rental income? This special circa-1930s residence was artfully restored by a master Craftsman in 2020 and is truly one-of-a-kind. There is an abundance of charm combined with comfortable living spaces in both homes. A showpiece of beamed cathedral and coffered ceilings;

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  751 Crowell Rd, North Chatham, MA 02650
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  /43

  Est $2,436,181 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,406 Sq Ft

  30 Pine Ln, North Chatham, MA 02650

  30 Pine Ln, North Chatham, MA 02650
• 

  

  /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
• 

  

  /12

  $415,000 Sold Aug 14, 2025

  • 836 Sq Ft
  • $496/SF
  • 3 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1982

  44 Misty Meadow Ln Unit 5, North Chatham, MA 02650

  Welcome to 44 Misty Meadow Lane #5, a beautifully renovated, furnished, and air-conditioned 1-bedroom, 1.5-bath condo in North Chatham. This move-in-ready home is perfect for enjoying the best of the summer season ahead. With 836 sq. ft. of smartly designed space, the updated condo has a spacious living-dining area perfect for entertaining. The modern kitchen offers ample cabinetry, granite

  Jack Farrell Compass

  44 Misty Meadow Ln Unit 5, North Chatham, MA 02650
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  /47

  Est $2,591,520 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,996 Sq Ft

  74 Frost Fish Rd, North Chatham, MA 02650

  74 Frost Fish Rd, North Chatham, MA 02650
• 

  

  /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

  $690,900 Sold Aug 07, 2025

  • 1,008 Sq Ft
  • $685/SF
  • 54 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1964

  99 Heritage Ln, Chatham, MA 02633

  What's on your wish list? A primary or vacation home that you can walk to downtown Chatham from with its fine dining, shopping and galleries...or to the bike path & pickleball? Look no further! 99 Heritage Ln is only 2/3 mile to Oyster Pond Beach and minutes away from the many beautiful south side beaches. Enjoy this comfortable 3-bedroom home with a large fenced-in backyard. Recent renovations

  Ella Leavitt Compass

  99 Heritage Ln, Chatham, MA 02633
• 

  

  /25

  Est $461,410 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,038 Sq Ft

  409 Orleans Rd Unit A, North Chatham, MA 02650

  409 Orleans Rd Unit A, North Chatham, MA 02650
• 

  

  /36

  $7,200,000

  • 5 Beds
  • 2.5 Baths
  • 1,896 Sq Ft

  238 Cranberry Ln, Chatham, MA 02633

  This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

  John Burke William Raveis Real Estate & Home Services

  238 Cranberry Ln, Chatham, MA 02633
• 

  

  /41

  $950,000 Sold Aug 07, 2025

  • 2,399 Sq Ft
  • $396/SF
  • 137 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 2015

  1082 Main St Unit 1082, Chatham, MA 02633

  Motivated sellers! Come take a look at this turn key, end unit townhome in beautiful Chatham! This serene setting overlooks Perch Pond where nature abounds.This 3 level townhome has an attached garage and private driveway, an extra "flex space" room on the 2nd level (could be an office, art studio, gym, 3rd bedroom, etc) and a finished lower level w/ large great room & full bath. This complex is

  Kristin Coletti William Raveis R.E. & Home Services

  1082 Main St Unit 1082, Chatham, MA 02633
• 

  

  /18

  Est $488,103 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,013 Sq Ft

  407 Orleans Rd Unit B, North Chatham, MA 02650

  407 Orleans Rd Unit B, North Chatham, MA 02650
• 

  

  /4

  $315,000

  • Land
  • 1.07 Acres
  • $294,393 per Acre

  2386 Main St, South Chatham, MA 02659

  This 1.069 acre lot is zoned R20 and partially R60. Great location close to the beach and bike trail. Buyer and their agent to do their own due diligence. Please verify all information contained herein.

  Judith Smith John C Ricotta & Assoc.

  2386 Main St, South Chatham, MA 02659
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  /34

  $700,000 Sold Aug 04, 2025

  • 600 Sq Ft
  • $1,167/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1948

  89 Ocean Port Ln, Chatham, MA 02633

  Welcome to this 2 bedroom cottage in a wonderful south of rte 28 location close to Hardings Beach. This 4 room cottage is year round with newer mechanicals and windows. It is in a neighborhood of larger homes, with easy access (walkable) to Barn Hill town landing and Hardings Beach. The current owners have plans available for a re-build of a larger home on the lot if that is desired. Excellent

  Kathleen Phelan Compass Massachusetts, LLC

  89 Ocean Port Ln, Chatham, MA 02633
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  /27

  Est $637,307 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft

  108 Misty Meadow Ln Unit B, North Chatham, MA 02650

  108 Misty Meadow Ln Unit B, North Chatham, MA 02650
• 

  

  /38

  $5,995,000

  • 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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  /27

  $1,189,000 Sold Jul 31, 2025

  • 1,384 Sq Ft
  • $859/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  32 Bishops Terrace, Chatham, MA 02633

  This beautifully renovated 3-bed, 2-bath home sits on .37 acres in a convenient, near-town location, about a mile from Main Street Chatham. The home embodies easy indoor/outdoor single floor living with a resort feel. The main living room connects to the well-appointed kitchen with eat-in dining area and oversized island. On one side of the home, you will find two sun filled guest bedrooms and

  Justin Blair Monomoy Properties Group LLC

  32 Bishops Terrace, Chatham, MA 02633
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  /26

  Est $406,164 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 836 Sq Ft

  36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

  36 Misty Meadow Ln Unit 1, North Chatham, MA 02650
• 

  

  /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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  /53

  $870,000 Sold Jul 31, 2025

  • 1,362 Sq Ft
  • $639/SF
  • 65 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  40 Florence Dr, South Chatham, MA 02659

  South of 28 Chatham 3BR home just 0.3 miles from Forest Beach on the ocean! Great rental income potential. Renovated in 2002 with a vaulted ceiling living room addition that doubles as a sunroom & opens to a large dining area that can fit all your guests around a big table. Hardwood floors in all 3 bedrooms, living room/sunroom & dining room. First-floor bathroom updated in 2009 with walk-in

  Melanie Cauchon Melanie Cauchon Real Estate

  40 Florence Dr, South Chatham, MA 02659
• 

  

  /29

  Est $1,099,167 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft

  56 Meadowbrook Rd, North Chatham, MA 02650

  56 Meadowbrook Rd, North Chatham, MA 02650
• 

  

  /7

  $315,000

  • Land
  • 0.47 Acre
  • $670,213 per Acre

  0 Tirrells Way, Chatham, MA 02659

  Building lot available! Located at the end of a cul-de-sac and abutting the Town Forest. Water Department has an easement for a road over the property at the edge of the lot boundary. All due diligence required for building allowances and restrictions are responsibility of the buyer. No engineering, perc tests or verification of available utilities have been performed.

  Kathy Doyle Gibson Sotheby's International Realty

  0 Tirrells Way, Chatham, MA 02659
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  /55

  $650,000 Sold Jul 31, 2025

  • 1,813 Sq Ft
  • $359/SF
  • 93 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  1996 Main St, Chatham, MA 02633

  Welcome to 1996 Main Street in the picturesque town of Chatham, MA! This charming 3-bedroom, 2-bathroom ranch style home spans 1,813 square feet and is ready for your vision and creativity. With several essential updates already in place, including a new roof, fresh shingles, and a newer gas heating system, you can focus on adding your personal touch to make this house your dream retreat. The

  Shane Masaschi Compass

  1996 Main St, Chatham, MA 02633

Showing Results 161 - 200, Page 5 of 18