Barnstable, MA Homes

/52
$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
/19
$5,000 per month
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
101 Monomoyic Way, Chatham, MA 02633

Available furnished rental November 1- April 30! Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that accentuate the

Steven Cohen Team Keller Williams Realty Boston-Metro | Back Bay

101 Monomoyic Way, 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

/12
Not Listed For Sale
140 Happy Valley Rd, Chatham, MA 02633

140 Happy Valley Rd, 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
/24
$4,500 per month
- 4 Beds
- 2 Baths
- 9,999 Sq Ft
- House for Rent
15 Myrtle Dr, South Chatham, MA 02659

PRICE SHOWN IS AMORTIZED AFTER SPECIAL OFFER. NOW OFFERING 1/2 MONTH FREE LIVING FOR LEASES SIGNED BEFORE 8/1. Don't miss this opportunity to rent this gem in one of Cape Cod's most beloved towns! Tucked away on a cozy side street, this gorgeous home is a walk away from Forest Beach and plenty of incredible restaurants. Step out on to your brand new outdoor deck and patio and enjoy a game of

Sean Anderson Access

15 Myrtle Dr, South Chatham, MA 02659
/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

/30
Not Listed For Sale
- 2 Beds
- 1 Bath
- 772 Sq Ft
25 Bobbie's Ln, Chatham, MA 02659

25 Bobbie's Ln, Chatham, MA 02659

/39
$1,700,000 Open Sat 10:30AM - 12PM
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
9 Bettys Path, Chatham, MA 02633

Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwork! This charming 3-bed, 2-bath home is nestled on a 1.8-acre lot, complete with a stunning kettle pond and a lush pastoral backdrop. Renovated in 2014, the home boasts a fresh roof and all the modern comforts. Step inside to find an inviting living room with a cozy fireplace, a dining room that opens onto a

Shane Masaschi

Compass

(508) 682-4461

9 Bettys Path, 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

/4
Est $3,235,621 Not Listed For Sale
- 3 Beds
- 5.5 Baths
- 4,197 Sq Ft
21 Hunter Rise, Chatham, MA 02633

21 Hunter Rise, Chatham, MA 02633

/6
$250,000
- Land
- 0.72 Acre
- $347,222 per Acre
0 George Ryder Rd Unit 73104629, Chatham, MA 02633

Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

Shane Masaschi

Compass

(508) 691-8324

0 George Ryder Rd Unit 73104629, 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

/54
Est $3,900,956 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,751 Sq Ft
110 Sea Shells Dr, South Chatham, MA 02659

110 Sea Shells Dr, South Chatham, MA 02659

/50
$975,000 Pending
- 2 Beds
- 2 Baths
- 1,340 Sq Ft
67 A Leonard Way, Chatham, MA 02633

Welcome to 67 A Leonard Way, a charming ranch-style 2-bedroom home tucked away on a quiet street just minutes from downtown Chatham. Inside you'll find a beautifully renovated kitchen with granite countertops, stainless steel appliances and custom cabinetry. The open living and dining areas feature a fireplace, built-in shelving, and hardwood floors, creating a warm and inviting atmosphere. With

Shane Masaschi

Compass

(508) 276-7761

67 A Leonard Way, Chatham, MA 02633
/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

/51
Est $3,015,836 Not Listed For Sale
- 6 Beds
- 4 Baths
- 4,449 Sq Ft
114 Main St, Chatham, MA 02633

114 Main St, Chatham, MA 02633

/18
$600,000 Pending
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
19 Stoughton Ln, Chatham, MA 2633

Here is your chance to own a slice of seaside Chatham! This prime location is only a short walk or .02 miles to stunning Ridgevale Beach on pristine Nantucket Sound. Included in the sale is a passing 3 bedroom Title V septic. Seller has building plans for a 3 bedroom, 2 bath, 1356 SF home. Imagine the possibilities of creating your own home on this rare piece of land in this welcoming, quaint

Shane Masaschi

Compass

(508) 400-2035

19 Stoughton Ln, Chatham, MA 2633
/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

/38
Est $2,197,794 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,008 Sq Ft
671 Old Harbor Rd, North Chatham, MA 02650

671 Old Harbor Rd, North Chatham, MA 02650

/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
/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

/37
Est $2,647,459 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,203 Sq Ft
47 Gladen Ln, Chatham, MA 02633

47 Gladen Ln, Chatham, MA 02633

/67
$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
/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

/12
Est $6,022,173 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,286 Sq Ft
486 Shore Rd, Chatham, MA 02633

486 Shore 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
/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

/26
Est $2,044,841 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
393 Main St, Chatham, MA 02633

393 Main St, Chatham, MA 02633

/52
$1,800,000 Pending
- 3 Beds
- 2 Baths
- 2,366 Sq Ft
10 Pursel Dr, North Chatham, MA 02650

WATER-VIEW & DEEDED ACCESS TO RYDERS COVE | ''Summer Wind'' - A Coastal Chatham RetreatNestled in one of Chatham's most cherished neighborhoods, ''Summer Wind'' is a timeless Cape Cod escape offering deeded access to Ryders Cove and a private association beach with direct access to Pleasant Bay. Perched gracefully above the water, this serene retreat delivers breathtaking views, impeccable

Diane Donahue Gibson Sotheby's International Realty

10 Pursel Dr, North Chatham, MA 02650
/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

/26
Est $2,550,621 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,174 Sq Ft
10 Mill Hill Ln, Chatham, MA 02633

10 Mill Hill Ln, 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 - Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva 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 a heated pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated fenced-in lawn. Ownership

Jack Bohman Gibson Sotheby's International Realty

101 Morris Island Rd, Chatham, MA 02633
/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

/44
Est $3,612,731 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,422 Sq Ft
50 Chase St, Chatham, MA 02633

50 Chase St, Chatham, MA 02633

/86
$5,750,000
- 7 Beds
- 3.5 Baths
- 3,734 Sq Ft
58 Oyster Bluff, Chatham, MA 02633

Perched high above Oyster Pond, this generational estate--first known as ''The Beach Plum House'' and later as ''Adsamore''--is one of Chatham's rarest offerings. Set on a remarkable .93-acre parcel with expansive frontage, it offers sweeping views of town and Oyster Pond, a lifestyle at once connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, the home has been

Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

58 Oyster Bluff, Chatham, MA 02633
/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

/59
Est $4,347,347 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,440 Sq Ft
62 Chase St, Chatham, MA 02633

62 Chase St, Chatham, MA 02633

/43
$2,299,999
- 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
/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

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