Chatham Massachusetts Real Estate & Homes For Sale

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$579,000
2bd
2ba
1050sqft

15 Balfour Lane
Chatham, Massachusetts 02633

Helen Malone
William Raveis Real Estate & Home Services
Beach Righs to White Pond! Own in time for summer enjoyment. Your dream condo is waiting for your ownership. This second floor unit of a 7-unit condo community provides everything you could want with fine craftsmanship evident in the special touches throughout.
$1,675,000
4bd
4ba
2668sqft
40,473Sqft

268 Sam Ryder Road
Chatham, Massachusetts 02633

Jason P Saphire
www.HomeZu.com
Large, exquisite home offered fully furnished! This design masterpiece set on .92 acres features a 4 BR septic system and over 4,000' of living space. Plenty of land for expansion ideas such as pool, detached garage/ apartment addition, tennis court or fire pit.
$625,000
2bd
1ba
966sqft
13,504Sqft

161 Shane Drive
Chatham, Massachusetts 02633

Gervais Group
Keller Williams Realty
This lovely ranch sits up on a raised lot in a sought-after Chatham neighborhood. There are lots of mature plantings that are awaiting your green thumb. The sunlit living room features a wood-burning fireplace and oak floors that continue through the dining room, hallway, and bedrooms. The open kitchen features a sliding glass door that opens to a large deck overlooking the private rear yard.
$229,000
720sqft
21,344Sqft

880 Main Street # A
Chatham, Massachusetts 02633

Nat S Santoro
Kinlin Grover Compass - Commercial
Spacious office unit or retail space available located on Main street in the heart of Chatham. Excellent exposure with a large street sign and proximity to the intersection of Route 28, Crowell Road, Queen Ann Road, and Depot Road. Convenient to everything Old Chatham Village has to offer such as art studios, restaurants, local markets, town offices and more.
$699,000
15,500Sqft

0 Taylor's Pond Road
Chatham, Massachusetts 02633

Amy L Harbeck
Kinlin Grover Compass
Located directly opposite the Town Landing and dock on Taylors Pond in South Chatham! This 1/3 acre lot boasts 195 ft of road frontage.
$1,650,000
3bd
2ba
3852sqft
37,026Sqft

355 Training Field Road
Chatham, Massachusetts 02633

Harry M Cutts
William Raveis Real Estate & Home Services
Enjoy a private setting in this move in ready home.! This comfortable 3852 square foot home including lower level features high ceilings and an open floor plan, granite countertops in a large kitchen and dining area. Additionally includes very adequate living room w/fireplace, primary bedroom with en suite bath, and a den, tv room or home office and half bath all on the first floor.
$599,000
2bd
1ba
869sqft

109 Misty Meadow Lane # 4
Chatham, Massachusetts 02633

Tony Guthrie
Berkshire Hathaway HomeServices Robert Paul Properties
Perfectly nestled on a quiet street this lovely second floor unit offers bright and sun drenched spaces that are warm, comfortable and inviting. A perfect home if you are just starting out or maybe if you need less living space.
$1,295,000
3bd
2ba
2797sqft
18,731Sqft

70 Uncle Deane's Road
South Chatham, Massachusetts 02659

David C Carter
Compass Massachusetts, LLC
A beautiful display of wood in this Post and Beam style home which includes 3 bedrooms 2 1/2 baths. Originally designed and built by its owner in 1980 with emphasis on detail. A significant plus is the 844 SF of finished space in the walkout basement along with lots of storage, an artist studio and much more.
$4,750,000
5bd
5ba
4000sqft
20,473Sqft

356 Stage Harbor Road
Chatham, Massachusetts 02633

Chris Rhinesmith
Compass Massachusetts, LLC
Affording coastal luxury and quality of design, this new construction residence takes advantage of an exceptional location along '' the Chatham loop'' and is also moments to the Village and Oyster Pond Beach. Meticulous choice of finishes combined with spacious proportions and a light filled open layout create an ambiance of tranquility.
$774,900
3bd
1ba
1166sqft
15,682Sqft

689 Orleans Road
North Chatham, Massachusetts 02650

Janice Alex
Christie's International Real Estate Atlantic Brokerage
Immaculate bungalow in North Chatham. This turnkey home has 3 bedrooms, 1 full bathroom, a first-floor laundry, and an open floor plan for entertaining. Updated kitchen with granite counter tops, stainless steel appliances and a gas range. Beautiful wood floors and period character throughout. Don't forget the expansive porch that runs along the front of the home.
$3,250,000
4bd
3ba
3532sqft
16,988Sqft

5 Hillcrest Lane
Chatham, Massachusetts 02633

Kathleen Phelan
Compass Massachusetts, LLC
Water views of the North cut in North Chatham. This timeless residence was renovated by Rick Roy construction. Open floor plan living combines with 4 Bedrooms, 3.5 baths, an office and a music room to offer all the space you would wish for in this iconic location in North Chatham.
$589,900
2bd
2ba
1508sqft

912 Main Street # X306
Chatham, Massachusetts 02633

Ella Leavitt
Kinlin Grover Compass
This exceptional end unit at Park Place has tree top views of the landscaped gardens below from its private deck. As one of the larger apartments in the complex, unit 306 has been nicely renovated and offers two bedrooms/two full baths, a separate laundry room and a separate dining room off the kitchen.
$1,569,000
5bd
6ba
11000sqft
119,354Sqft

558 Fox Hill Road
Chatham, Massachusetts 02633

John dePreaux
Corcoran Property Advisors
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.
$1,675,000
3bd
3ba
3428sqft
15,682Sqft

98 Orleans Road
North Chatham, Massachusetts 02650

Jason P Saphire
www.HomeZu.com
Location, location, location! Designer masterpiece, offered fully furnished for turnkey occupancy! This amazing central location in North Chatham is just steps away from lovely Cow Yard Beach and a short walk to the Fish Pier, Chatham Bars Inn and A's field. Stroll into town for dining, shopping, parades or band concerts.
$2,950,000
3bd
3ba
3444sqft
17,424Sqft

87 Squanto Drive
Chatham, Massachusetts 02633

Nancy E Griffin
Advisors Living, LLC
Welcome to your boater's paradise, where every day unfolds against the backdrop of sweeping marsh and Oyster Pond views, complemented by the picturesque Chatham Yacht Basin. Custom-built in 2010, this meticulously crafted residence has been thoughtfully updated, boasting a new roof installed in 2023 and solar panels added for eco-friendly living.
$1,695,000
3bd
2ba
1840sqft
16,553Sqft

371 Cedar Street
Chatham, Massachusetts 02633

Hilary Bovey
Coldwell Banker Realty
Welcome to this exciting and special property! Dramatic night-lit hardscaping & thoughtful plantings encompass a light & bright home with peaceful conservation views and privacy. On the coveted ''LOOP'' location, sidewalks will take you to the village center & the sandy beaches of Chatham.
$4,195,000
4bd
4ba
3915sqft
50,094Sqft

98 Attucks Trail
Chatham, Massachusetts 02633

Fisher + Marks
Berkshire Hathaway HomeServices Robert Paul Properties
Welcome to 98 Attucks Trail... nestled amidst picturesque estates, this meticulously crafted home offers a rare opportunity to experience the epitome of coastal Atlantic living. Situated on Morris Island, one of the most coveted locations on Cape Cod, this property defines unrivaled exclusivity. Embrace the serenity of the surroundings as you step into the meticulously landscaped 1.15 acres.
$1,075,000
5bd
3ba
1968sqft
24,829Sqft

108 Island View Lane
South Chatham, Massachusetts 02659

Lori Jurkowski
Kinlin Grover Compass
This lovely Cape-style ranch on a quiet dead end side street overlooks Conservation, and is only 8/10 mile to Cockle Cove Beach. An ideal investment property, benefit from a lucrative rental history including many repeat rentals in place for 2024. The first floor offers a sun-filled kitchen & adjacent dining area with oversized windows.
$229,000
1bd
1ba
450sqft

33 Cross Street
Chatham, Massachusetts 02633

Eve Lorenz
William Raveis Real Estate & Home Services
Chatham House Co-Op opportunity in Chatham center. Spacious sunny one bedroom, one bath unit on ground level with small deck.Walk to shops, restaurants and beach. Please inquire for more information on the co-op. Have documents in hand to share.
$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.
$2,995,000
3bd
4ba
4102sqft
20,909Sqft

37 Jessies Landing
Chatham, Massachusetts 02633

Jeffrey E Cusack
Cove Road Real Estate
This impeccable custom-built Eastward home is just a short jaunt to Harding's Beach and in better-than-new condition thanks to the remarkable refinements of the current owner-designers. 4000 sq ft of flawless composition on three levels with every space offering artful finishes, heirloom quality fixtures and custom millwork and built-ins.
$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
1850sqft
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.
$9,800,000
8bd
6ba
4615sqft
128,066Sqft

504 Old Harbor Road
North Chatham, Massachusetts 02650

The Nickerson Power Group
Kinlin Grover Compass
''Turntide'' is a spectacular quintessential Cape Cod estate featuring elevated breathtaking panoramic vistas of Chatham Harbor & Atlantic. From this 8 BED/5.5BA mansion you will enjoy unsurpassed sunrises and romantic nights watching the moon rise over the Outer Beach. You will never want to leave.
$5,995,000
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.
$899,000
3bd
2ba
1786sqft
10,890Sqft

25 Greenwood Lane
Chatham, Massachusetts 02633

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.
$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.
$7,495,000
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.
$3,900,000
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.
$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.
$2,100,000
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 this June. Custom builder Sears Point Residential is building another stunning Chatham home. This in-town four-bedroom, three full and two half baths, 3,298 sq ft home includes a finished lower level and exquisite private outdoor living space with a swimming pool and whole house generator. This brand-new home will be move-in ready for mid-June 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.
$2,995,000
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.
$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.
$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.
$6,250,000
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.
$6,500,000
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.
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