103 houses for sale in Old Chatham

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

A Grand Dame in Old Chatham. Discover the joy in bringing back a classic. All the bones are solid. Five bedrooms in that rambling feel that makes farmhouses so lovable. The great room fireplace combines stone and real wood panels with views of the pond out the windows. A formal dining with wainscoting leads to a kitchen that leads out back. A second living room that could be it's own apartment. Finish the primary and create a vaulted masterpiece. The land runs over 15 acres of forest with a magnificent pond. There's a garge at the house. Then there's a 40'x60' garage/workshop is perfect for the hobbiest

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers generous space to gather and unwind with family and friends. At its center, the kitchen and living areas are designed for connection. The open kitchen and dining space flows easily into the main living room, where a stone fireplace anchors the room and creates a natural place to come together after a day outdoors. Stainless steel appliances and ample workspace make the kitchen as functional as it is welcoming, equally suited to large weekend meals or quiet mornings overlooking the landscape. Windows throughout frame views of pasture, pond, and sky, keeping the surrounding land present from nearly ev

Open house sumday. June 28th from 2-4. Please come! If you are looking for a move-in ready village farmhouse in Hudson Valley's Columbia County, you have found it! This gut-renovated home in charming and desirable Old Chatham is perfect for a weekend or full-time residence. There are 3 bedrooms, 2 ½ retiled, replumbed and rebuilt bathrooms, a huge dressing room with custom built shelves and clothes racks, a wood burning stove, formal dining room, gourmet kitchen and closets everywhere. The new clothes washer and dryer are conveniently located on the 2nd floor. This home features a brand-new Wolf Stove, Bosch refrigerator and dishwasher, quartz kitchen countertops and gorgeous custom solid wood cabinets, farmhouse sink, thermally efficient windows, new wrap around deck and site-specific water filtration system. The hardwood floors have been stripped, sealed and coated throughout the entire house. The entire exterior of house was stripped, sanded and painted in 2025. The roof was repaire

Timeless farmhouse charm meets modern luxury in the heart of Old Chatham. Set on 1.4 picturesque acres, this beautifully renovated 1875 home has been thoughtfully restored from top to bottom, blending historic character with contemporary comfort. Inside, you'll find sun-filled living spaces, gleaming hardwood floors, a gourmet kitchen featuring a Wolf range, Bosch appliances, quartz countertops, and custom solid wood cabinetry, plus three spacious bedrooms, 2.5 designer baths, and an oversized dressing room. Outside, enjoy a brand-new wraparound porch overlooking peaceful grounds that invite morning coffee, evening cocktails, and everything in between. Whether you're searching for a full-time residence or the perfect Hudson Valley weekend escape, this move-in-ready home offers the rare combination of classic farmhouse warmth, exceptional craftsmanship, and effortless living in one of Columbia County's most charming villages

Nestled within the serene hamlet of Old Chatham, this exceptional country home offers 43 private acres with stream frontage and abundant wildlife. Thoughtfully renovated and impeccably maintained, the residence seamlessly blends timeless rural character with modern comfort. Recent enhancements include a beautifully redesigned kitchen and bath, upgraded sound attenuation for enhanced privacy, a standing seam metal roof, updated electrical wiring with a 200-amp panel, HVAC with central air conditioning, whole-house water treatment with reverse osmosis, and a new well pump. Designed for those seeking an escape immersed in nature, the property invites effortless, low-maintenance indoor-outdoor living. Spend quiet mornings on the porch overlooking the landscape, start a garden, blaze trails through the natural corridors, or unwind beside the soothing sounds of the stream that borders the property. A secluded natural pond tucked along the southern edge further enriches the home's sense of tr

2-Storyu002F5-Apartmentu002F9BRu002F6BA building PLUS 2BRu002F1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snowu002Ftrash removal, wateru002Fsewer, off-street parking, fridgeu002Fstove each unit. 2 SBL lot numbers. Properties not sold separately. Assessmentu002Ftax figures herein reflect total due for both properties. Photos incl Ranch house and 2 apartments pre-occupancy. 48-72 hour notice required to show. Buyeru002FCoop brokers must attend all appointments. Thank you for your interest

Experience the perfect blend of historic settlement and pastoral tranquility, enhanced by the abounding Valatie Kill on the property in the coveted hamlet of North Chatham. This is a rare opportunity to own a home in a nationally recognized Historic District, where 18th-century charm meets the modern desire for space and serenity. This very sweet 3200 square foot 4 bedroom 2.5 bathroom home comes to the market for the first time in nearly 50 years and preserves its colloquial charm throughout. Featuring an eat in kitchen and gracious dining room, it is a wonderful gathering spot. A downstairs primary en suite bedroom is coupled with a living room with fireplace and a seasonal sunroom with a herringbone patterned red brick floor, creating a heart and hearth with plenty of rooms to congregate. Add to the main house a two story barn and a car garage making this offering a workable home for many folks. North Chatham NY is a close knit community and a collection of perfectly charming 18th a

1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High visibility on main NY-MA artery. Fantastic location for studio or professional spaces incl massage, acupuncture, attorney, chiropractor, accountant. Centrally located Columbia/Albany/Berkshire counties. Fully rented: 1st flr tenant 1100 dollars/mth; 2nd flr tenant 1750 dollars/mth. 24-48hr notice required to show. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company

Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/ I90/ Berkshire Spur, 15 minutes to Lenox/ Tanglewood, 30 minutes Albany/ Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased for 2,300 dollars/MTH til 8/31/26. 2nd bldg is East Chatham Wine & Spirits store w/half-bath currently 1541 dollars/MTH-to-mth. 3rd bldg currently a funeral parlor/office w/half-bath 850 dollars/MTH til 4/30/26 All photos pre-occupancy. All units occupied. No interior liquor store photos. Tenants must approve all showings and provide access. 48HR notice minimum

Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/I90/Berkshire Spur, 15 minutes to Lenox/Tanglewood, 30 minutes Albany/Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased for 2,300 dollars/MTH til 8/31/26. 2nd bldg is East Chatham Wine & Spirits store w/half-bath currently 1541 dollars/MTH-to-mth. 3rd bldg currently a funeral parlor/office w/half-bath 850 dollars/MTH til 4/30/26 All photos pre-occupancy. All units occupied. No interior liquor store photos. Tenants must approve all showings and provide access. 48HR notice minimum. By appt only

Welcome to the original early 1800's John Jay van Valkenburgh home in the quaint and historic hamlet of Chatham Center. This three bedroom, charming two-story colonial farmhouse on 1.6 acres features original wood beams, a working fireplace with wood stove insert in the large open living room, hardwood floors and an adjoining dining room with a cast iron wood stove. A modern kitchen with stainless appliances, quartz countertops and washer/dryer adds to the conveniences. There is a cozy den/office with a half-bath adjoining the kitchen. Upstairs, there are 3 bedrooms with ample closet/storage space and a full bath. The property is surrounded by mature plantings, stone walkways and a barn with workbench and a potting shed. The side yard features a 16 x36 in-ground heated pool with lush plantings. The backyard features a vegetable garden and a beautiful sitting area with expansive lawn and large crabapple trees. The property is beautifully hidden as you come up the driveway, surrounded by

Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6 spacious bedrooms and 5 bathrooms, including an ideal in-law suite or private apartment setup for extended family, guests, or potential additional living space. The heart of the home is the incredible chef's kitchen-thoughtfully designed with generous work space, high-end finishes, and the kind of layout any chef or aspiring cook would absolutely love. Step outside to enjoy the wrap around deck overlooking the built-in saltwater pool and serene grounds, creating the perfect setting for entertaining or simply relaxing into total privacy. A 3-car garage plus an additional garage beneath the residence pro

2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers. Properties not sold separately. Assessment/tax figures herein reflect total due for both properties. Photos incl Ranch house and 2 apartments pre-occupancy. 48-72 hour notice required to show. Buyer/Coop brokers must attend all appointments. Thank you for your interest

Offered for the very first time in 63 years, this exceptionally well-maintained ranch is a rare opportunity to own a beloved property that has been carefully cared for by its original owner. Set on an impressive 14.9 acres in the picturesque hamlet of Malden Bridge, this 3-bedroom, 2-bath home combines comfort, privacy, recreation, and future potential in one remarkable package. Inside, you'll immediately appreciate the pride of ownership throughout. The spacious living room is warm and inviting, featuring a wood stove that creates the perfect gathering place during the cooler months. A formal dining room with beautiful built-ins offers timeless character and an ideal setting for holiday meals and entertaining. Gleaming wood floors add warmth and charm throughout much of the home, while the stunning main bathroom showcases a granite-topped vanity and thoughtful updates. The layout is practical and comfortable, providing easy one-level living with generous room sizes. The lower level ad

Once a true fixer-upper, this property has already begun its transformation. The current owner started renovations and updates (New mini splits (heating and cooling), propane heaters, insulated attic, sealed roof, full kitchen, flooring, plumbing, and back deck replaced) creating a strong foundation for the next buyer to complete the vision. The main level offers two bedrooms, and bathrooms on the main level providing a functional and desirable layout. Step outside to a newly build deck overlooking the backyard. Perfect for relaxing or entertaining. A detached garage adds convenience and extra storage. With several improvements already in place, this home presents and excellent opportunity for investors or owner-occupants to finish the project and build instant equity

Fantastic colonial fixer upper with 5-bedrooms and one bath located in Chatham School District. Plenty of room for everyone. Light & bright kitchen with fir floors. Bedroom on first floor. Big back yard. Ready to make it your own

Sitting on almost an acre with a stream in back, this beautifully maintained Colonial has a ton to offer. Pulling up to the property you have a two car garage and she-shed (with electricity), a fenced in yard surrounding the oversized new back deck and pool. Walking inside, a mudroom with an office and a dining room lead into the living room with a gas fireplace. The kitchen and baths are all updated. Upstairs you have three full size bedrooms and laundry. Come enjoy this home inside and out

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank