Chatham Massachusetts Real Estate & Homes For Sale

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$1,275,000
3bd
2ba
2393sqft
10,454Sqft

32 Wells Hollow Road
North Chatham, Massachusetts 02650

Leo Doyle
Oceanside Realty Group
Come see this Well Built and Beautifully Maintained Colonial in North Chatham. It's tucked away on a peaceful dead end road, but is just minutes from Chatham's beloved Main Street and Lighthouse Beach. A Fantastic Layout provides a first floor Primary Bedroom and Bath, plus another half bath, living room, dining room, and a kitchen that's open to a Generous Sized Family Room with fire place.
$955,000
4bd
2ba
1572sqft
12,180Sqft

16 Sulphur Springs Road
Chatham, Massachusetts 02633

Ella Leavitt
Kinlin Grover Compass
Welcome to 16 Sulphur Springs Rd where you can stroll to West Chatham Village center, access the bike trail or take a neighborhood path to Ridgevale Beach. Hardings Beach is just minutes away by car, bike or foot. This four bedroom, two bath expanded ranch has been tastefully renovated to meet the needs of today's lifestyle living.
$1,695,000
3bd
2ba
2630sqft
37,026Sqft

55 Eldredge Square S
Chatham, Massachusetts 02633

Jessica Metzler
Compass Massachusetts, LLC
This Cape Cod Style home is tucked away in a private enclave minutes to Chatham Village, the Fish Pier and the Chatham A's ballfield. The first floor open layout features a fireplaced living room and family room that transitions to a backyard private patio and a deck overlooking conservation land.
$2,600,000
2368sqft
52,708Sqft

31 Meetinghouse Road
South Chatham, Massachusetts 02659

Amy L Harbeck
Kinlin Grover Compass
Amazing combination of pristine office space, an attractive Doctor's en suite, and a separate 3,344 sqft building with 7 warehouse bays and a huge unfinished room above in a highly visible location! The 2368 sqft front building (3 levels) was rebuilt from the slab up in 2012 with high-quality finishing and appointments thru-out.
$875,000
3bd
2ba
1540sqft
28,750Sqft

312 Round Cove Road
Chatham, Massachusetts 02633

Michael Ulrich
Cape Cod Associates R E
Fantastic opportunity to own in River Bay. Home needs some updates, but beautiful large lot with home set back off the road make this an ideal spot to call home.
$5,495,000
2bd
2ba
4786sqft
62,726Sqft

99 Uncle Alberts Drive Extension
Chatham, Massachusetts 02633

Rick Smith
Gibson Sotheby's International Realty
Tucked away in a very private setting in Chatham, this historic 1.4 acre Waterfront estate property offers a blend of luxury and legacy. Previously part of Chatham Bars Inn's farm, it's been in one family for more than 70 years, promising a serene coastal retreat. The south-facing lot overlooks Oyster Pond and Oyster River, ideal for a custom 4-bedroom home with panoramic views.
$779,000
2bd
2ba
1356sqft
16,117Sqft

2 Uncle Zlotis Road
Chatham, Massachusetts 02633

Timothy P Bailey
John C Ricotta & Assoc.
Very cute and private 2-bedroom 2 bath Ranch with new Primary bedroom addition constructed by Rob Stello. Hardwood and tile throughout. Vaulted ceiling in living room.
$6,500,000
5bd
6ba
5143sqft
33,977Sqft

4 Ministers Lane
North Chatham, Massachusetts 02650

Chris Rhinesmith
Compass Massachusetts, LLC
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.
$6,150,000
3bd
3ba
4142sqft
31,823Sqft

146 Strong Island Road
North Chatham, Massachusetts 02650

Dillan W Hoyt
Greer Real Estate, LLC
Modern elegance and unparalleled luxury encompass 146 Strong Island Road. Lavishly appointed details from floor to ceiling complement the water views.
$995,000
2bd
2ba
1786sqft
10,890Sqft

25 Greenwood Lane
South Chatham, Massachusetts 02659

Lori L Fanning Smith
Compass Massachusetts, LLC
Chatham Beach house is calling! Enjoy Chatham from this casual home with flexible floor plan located south of RT 28.....This house lives large with two bedrooms , office, two family rooms, and living room with fireplace. This one level home with beach vibe also offers an updated kitchen with new appliances and granite center island.
$719,000
3bd
3ba
1196sqft
15,246Sqft

158 Holly Drive
South Chatham, Massachusetts 02659

Cape Cod Power of Two
William Raveis Real Estate & Home Services
Here is your chance to own in South Chatham. This is currently one of the only single-family properties in Chatham listed for under $720k. Come discover this lovely sunlit ranch located conveniently between Forest Beach/Rt 28 and East Harwich Center.
$899,000
2bd
1ba
710sqft
20,473Sqft

20 Cedar Swamp Lane
Chatham, Massachusetts 02633

Reciprocal Agent
Reciprocal Office
Waterfront, renovated & an unbeatable location! With unobstructed views of the tidal inlet off Stage Harbor, this property is the perfect blend of privacy & convenience. Situated only 0.
$769,000
3bd
1ba
1890sqft
19,602Sqft

8 Uncle Zlotis Road
Chatham, Massachusetts 02633

The Nickerson Power Group
Kinlin Grover Compass
Prepare to be surprised by the spacious open floor plan of this ranch-style home. Upon entering you'll be greeted by beamed living room with cozy fireplace, bow window and bookcase. The open dining area flows seamlessly into the bright white kitchen, bathed in natural light by a big skylight.
$849,000
2bd
3ba
1368sqft
21,954Sqft

199 Crowell Road
Chatham, Massachusetts 02633

Brennan Finnegan
William Raveis Real Estate & Home Services
Elegant and spacious 2-bedroom, 3-bath free-standing condo in the heart of Chatham. This unit features an open floor plan with abundant natural light, a large kitchen with island and granite countertops, and a full first floor bathroom. The second floor features two ensuite bedrooms, each with full bathrooms.
$4,900,000
5bd
6ba
5578sqft
90,169Sqft

67 Uncle Alberts Drive
Chatham, Massachusetts 02633

W&W Boston/Cape Cod Connection
Compass Massachusetts, LLC
Welcome to 67 Uncle Alberts Drive, a charming Cape Cod home nestled in the picturesque town of Chatham, MA. This outstanding property offers a perfect blend of classic Cape Cod architecture and modern design. The design is perfect for entertaining with an open first floor concept, a play room on the second floor and a finished lower level as well.
$3,700
4Room(s)
2631sqft
15,682Sqft

403 Main Street
Chatham, Massachusetts 02633

The Caron Group
Christie's International Real Estate Atlantic Brokerage
Rare opportunity to lease a recently updated and charming commercial space on Chatham's Main Street in the coveted downtown historical district.The structure, which was originally built in 1770 on Nantucket, boasts approximately 1,245 square feet of first floor space, a half bathroom, a deck, and private parking lot.
$2,850,000
3bd
5ba
4197sqft
20,038Sqft

21 Hunter Rise
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
This beautifully designed Eastward Companies home resides at the entrance of Hunter Rise just moments to Barn Hill Landing and 1/2 mile to Hardings Beach. Blending a classic coastal style aesthetic with a flowing open layout, the home impresses with a multitude of custom finishes like cabinetry, tile work and wall and ceiling shiplap.
$8,495,000
5bd
2ba
2992sqft
30,492Sqft

70 Sears Pt Lane
Chatham, Massachusetts 02633

Lori L Fanning Smith
Compass Massachusetts, LLC
Overlooking the iconic Stage Harbor Lighthouse, this picturesque property is unrivaled with over 200 feet of beachfront, a deep water dock, and ever changing views of Oyster River,Nantucket Sound,Stage Harbor and the Atlantic beyond. Boaters will relish the easy access into Nantucket Sound for fishing.
$4,199,999
5bd
5ba
4048sqft
29,621Sqft

155 Inlet Road
Chatham, Massachusetts 02633

Janice Alex
Christie's International Real Estate Atlantic Brokerage
It's a pleasure to offer this exceptional home located on the iconic ''Loop'' that showcases some of the most picturesque views and impressive neighborhoods in town. This 4,000 sf, 5-bedroom residence is set on a .68-acre lot. Offering an outstanding location, deeded access to Mitchell River, and panoramic views from the roof top deck of the ocean, sound and beyond.
$535,975
2bd
2ba
1075sqft

53 Toms Way
Chatham, Massachusetts 02633

Pauline F Teas
Christie's International Real Estate Atlantic Brokerage
Come enjoy easy low-maintenance one-level living in Chatham! This beautifully refurbished 2 bedroom, 2 bath end unit condominium is ready to move in. You will love the beach feel in your new home with the coastal theme colors of white and blue kitchen cabinets, driftwood inspired flooring and Dove White paint throughout. The kitchen is also equipped with brand-new stainless-steel appliances.
$1,795,000
3bd
2ba
2430sqft
16,969Sqft

70 Lantern Lane
South Chatham, Massachusetts 02659

Judith L Smith
John C Ricotta & Assoc.
Incredible spot...Tucked away at the end of a private lane and only a short distance to Cockle Cove beach, 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 guests.
$1,569,000
5bd
6ba
11000sqft
119,354Sqft

558 Fox Hill Road
Chatham, Massachusetts 02633

Meg Andrews
Compass Massachusetts, LLC
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.
$2,150,000
6bd
3ba
4313sqft
101,495Sqft

580 Meetinghouse Road
South Chatham, Massachusetts 02659

David C Petrasko
Cape Harbor Realty
4,313 Sq. Ft. Finished Living Area (2,813 1st FL, 1,500 LL) & 2.3 Acres with access to & ownership of Ministers Pond.(kayak, fish, trout stocked. Ideal for weddings, gatherings, or seasonal rentals. Consistently high rental history with bookings of $70 K for 2024 in place. Early buyers may have option to waive rentals. Walking paths leading to conservation trails & Goose Pond.
$1,600,000
58,333Sqft

13 Captain Knowles Way
Chatham, Massachusetts 02633

Timothy P Bailey
John C Ricotta & Assoc.
Fabulous Oyster River 1.34 acre waterfront lot with 180'+ of water frontage located in one of Chatham's most desirable neighborhoods. Imagine building your dream home on this private elevated lot with deep water access to Nantucket Sound and the Atlantic Ocean.
$950
480sqft
10,454Sqft

30 Market Place # B
Chatham, Massachusetts 02633

Tracy S Grattan
Christie's International Real Estate Atlantic Brokerage
For Rent - A first-floor professional office/business space is available for immediate occupancy. This bright sunny unit is located on the first floor to the left upon entrance of the commercial building at 30 Market Place. Central Chatham location South of Route 28 at the end of a cul de sac. Plenty of parking directly in front of the building.
$2,200,000
7bd
4ba
3022sqft
10,890Sqft

812 Main Street
Chatham, Massachusetts 02633

A Cape Life
Today Real Estate
Unique opportunity to own in popular downtown Chatham with all the amenities including shopping, restaurants, local beaches and more! Follow the brick walkway to your outdoor patio area or your four season porch that offers natural lighting and views onto Main Street.
$3,795,000
4bd
3ba
3298sqft
10,019Sqft

184 Barcliff Avenue
Chatham, Massachusetts 02633

The Bohman Hartung Group
Gibson Sotheby's International Realty
Brand New Construction - Move In for Summer 2024. Custom builder Sears Point Residential is building another stunning Chatham home. This in-town 4 bedroom, 3 full and 2 half baths, 3,298 sq ft home includes a finished lower level and exquisite private outdoor living space with a swimming pool. This brand-new home will be move-in ready for mid-summer 2024.
$2,295,000
3bd
2ba
2020sqft
43,700Sqft

17 Geranium Drive
Chatham, Massachusetts 02633

Cheryle W Young
Today Real Estate
PEACEFUL PRIVACY and WATER VIEWS - Beautifully landscaped one acre lot offers tranquility at this idyllic Cape Cod property which must be seen to be truly appreciated. Exemplifies charm and character. Entertain or just relax on the oversized mahogany deck with breathtaking, southwesterly views over the marsh, Sequanset Cove and out to Nantucket Sound.
$3,250,000
4bd
5ba
3415sqft
10,890Sqft

26 Seaview Street
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Nestled right in the heart of Chatham Village, this four bedroom five and half bath residence exudes charm and a perfect Cape Cod lifestyle with all of Chatham's restaurants, boutiques and Oyster Pond Beach moments away. The home is characterized by its timeless Greek Revival architecture, red cedar roof and intricate outdoor stonework.
$1,775,000
3bd
3ba
2646sqft
61,420Sqft

1934 Main Street
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
New Construction in Chatham! Just a short drive to Ridgevale Beach, Hardings, South Chatham shoreline beaches, restaurants and Chatham Rail Trail access. Nestled off of Main Street, this home can also offer a compound opportunity with the abutting new construction property. The interior features an open living great room with dining area that faces a large stone patio with saltwater pool.
$8,250,000
4bd
6ba
6128sqft
20,473Sqft

30 Fairway Drive
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
This architectural masterpiece perched above Chatham Seaside Links in a highly coveted Village enclave offers an incredible array of breathtaking vistas with easterly views of Chatham Harbor. The home embodies elegant coastal style with showpiece finishes, custom detailing and countless amenities.
$325,000
1284sqft

26 George Ryder Rd Road
Chatham, Massachusetts 02633

Bradford Kuhrtz
Commercial Realty Advisors, Inc.
Chatham Professional Building - Units 1 & 2 For Sale - join other professionals in this high end office building located just off of Route 28 in West Chatham. A short drive to down town and convenient to all Lower Cape Points. Units 1 & 2 total +/- 1,284 sq. ft. of first floor space which consists of 3 private offices, 3 administrative support offices, and a conference room.
$3,600,000
8bd
4ba
4413sqft
76,230Sqft

111 Barcliff Avenue
Chatham, Massachusetts 02633

Kimberly A Robbins
Compass Massachusetts, LLC
Sitting on 1.74 acres on Black Pond, this is a truly unique and meticulously maintained Chatham compound that offers a variety of possibilities. Whether you're looking for an investment property, a retirement home, a second home, or the potential for expansion, this property has it all. The main home features 4 bedrooms and 4.5 bathrooms.
$6,500,000
9bd
9ba
6688sqft
23,974Sqft

326 + 324 Main Street
Chatham, Massachusetts 02633

The Bohman Hartung Group
Gibson Sotheby's International Realty
Landmark Main Street Chatham mid-19th century Victorian thoughtfully restored inside and out by renowned architects and builders Polhemus Savory DaSilva.
$1,500,000
5bd
4ba
2400sqft
65,340Sqft

2388 Main Street
South Chatham, Massachusetts 02659

W&W Boston/Cape Cod Connection
Compass Massachusetts, LLC
Rare opportunity featuring a legal 2 family even though it is currently functioning as a single family home. With 5 bedrooms, 4 full baths, and a host of impressive features, this home offers the perfect blend of elegance and functionality.Step into a world of culinary delight with a gorgeous kitchen, complete with a custom walk-in pantry, catering to your every need.
$1,200,000
2040sqft
10,890Sqft

71 Crowell Road
Chatham, Massachusetts 02633

Bradford Kuhrtz
Commercial Realty Advisors, Inc.
Chatham Village For Sale - renovated, turn- key cafe & bakery. Longtime home to the Chatham Village Bakery and most recently EmmaBelle's, this prime location is available for a new operator. Centrally located on Crowell Road, the property is convenient to all Chatham and Lower Cape points.
$995,000
2bd
2ba
1977sqft
23,958Sqft

31 Great Hill Road
Chatham, Massachusetts 02633

Judith L Smith
John C Ricotta & Assoc.
Come view this two bedroom two bath home with an office perfect for those working from home. Lots of living space for family and friends - living room with fireplace and family room overlooking the back yard. Close to bike trail, basketball, and tennis courts. Wonderful sunroom, screened porch and enormous deck leading out to woodburning fire pit. Large lot with expansion possibilities.
$6,895,000
2bd
2ba
2214sqft
79,715Sqft

372 Fox Hill Road
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom, two bath waterfront home that feels like a private sanctuary exuding a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club.
$1,695,000
6bd
5ba
2572sqft
26,572Sqft

72 Forest Beach Road
Chatham, Massachusetts 02633

Michael Magner
Berkshire Hathaway HomeServices Robert Paul Properties
Investors & family compound seekers take notice! Completely renovated and offered fully furnished. Located south of Route 28 and 4/10 of a mile to Nantucket Sound, this one time motel has been meticulously renovated and is awaiting its new owner. This 6 bedroom, 5 full bath property would make the perfect compound or short term rental unicorn.
$6,995,000
5bd
4ba
4000sqft
88,427Sqft

270 Stage Island Road
Chatham, Massachusetts 02633

Sharon Mabile
Berkshire Hathaway HomeServices Robert Paul Properties
A captivating coastal gem, nestled on the crest of Stage Island and surrounded by the scenic waters of Nantucket Sound, this picturesque setting offers a serene and idyllic backdrop for nature enthusiasts and beachgoers alike.
$5,495,000
5bd
7ba
5519sqft
37,462Sqft

21 Captains Cove Lane
North Chatham, Massachusetts 02650

Shane K Masaschi
Kinlin Grover Compass
This exceptional 5 bedroom coastal retreat & boater's delight offers the best of waterfront living; complete with a private deep water dock on Ryder's Cove! Beautifully constructed by Eastward Homes, the home is nestled in a private cul-de-sac and positioned to provide stunning water views from nearly every room.
$1,150,000
15,040Sqft

287 Cedar Street
Chatham, Massachusetts 02633

Shane K Masaschi
Kinlin Grover Compass
Lot is cleared & building permit is in hand! Design & build the home of your dreams 'on the loop' with town sewer in the near future! Walk to the village, the ocean, fabulous restaurants, and the movie theatre, take in a baseball game and enjoy the shops. This .35 acre lot features 128' of frontage.
$299,000
31,167Sqft

0 George Ryder Road
Chatham, Massachusetts 02633

Shane K Masaschi
Kinlin Grover Compass
Lot has been filled in! 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, with approvals a 4-bedroom may be possible. Buyer's & buyer brokers verify sewer regulations with Board of Health as rules continue to change. The water, gas, electric, cable and sewer are on George Ryder Road.
$1,124,999
3bd
3ba
2400sqft
21,780Sqft

34 Horizon Drive
Chatham, Massachusetts 02633

Doug Grattan
Christie's International Real Estate Atlantic Brokerage
What a great place to spend the summer! Part of the Great Hill Estates neighborhood of Chatham, this 3-level home enjoys Southern exposure, tree top views and deeded access to Lover's Lake. Nantucket Sound beaches and downtown Chatham's shops and restaurants are just a few minutes away. Spanning over 2,400 sf on 3 levels, the home is sure to be a hit with family and friends.
$749,000
2bd
2ba
1884sqft
20,473Sqft

41 Edgewood Circle
Chatham, Massachusetts 02633

Shane K Masaschi
Kinlin Grover Compass
Nestled in a private neighborhood at the end of a cul-de-sac don't miss this move-in ready Chatham get-away! This comfortable 1,884 square foot home features space to live with a large kitchen w/breakfast bar & dining area, a dining room, living room w/fireplace, den or home office and full bath all on the first floor.
$829,000
4bd
2ba
2212sqft
10,860Sqft

23 Malabar Road
Chatham, Massachusetts 02633

The Bohman Hartung Group
Gibson Sotheby's International Realty
Wonderfully unique opportunity in Chatham to purchase a virtually turn-key four-bedroom, two-bath home with a sweet backyard. The 8 room house totals 2,212 sq ft of finished living space with 1,547 sq ft on the first two floors and 665 sq ft of finished basement.
$315,000
46,609Sqft

2386 Main Street
South Chatham, Massachusetts 02659

Judith L Smith
John C Ricotta & Assoc.
Build your new Chatham home on this1.07 acre lot. It 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.
$4,995,000
6bd
4ba
2919sqft
64,469Sqft

189 Moonpenny Lane
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Perfectly sited on 1.4 acres directly on Oyster Pond River, this spectacular waterfront six bedroom property overlooks one of Chatham's most coveted vistas of the iconic Stage Harbor Lighthouse. From every vantage point, there are sweeping views of the waterfront with beautiful sunsets, swimming, clamming and relaxing at the beach right outside your door.
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