88 properties 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

Welcome to Wilbor Farmhouse, a circa 1875 Victorian on 1.4 acres in the historic hamlet of Old Chatham. A wraparound covered porch, decorative wood brackets, and custom shutters give the house its period charm, and original wide-plank pine floors carry that history inside. Fully restored from top to bottom, it offers three bedrooms, 2.5 baths, and a large yard. A wood stove warms the sitting room, and the all-new kitchen, with energy-efficient appliances and custom solid wood cabinetry, opens to a deck for summer dinners. Once a bed and breakfast, the house is a short walk from the Old Chatham Country Store, ten minutes from Chatham's thriving arts scene, and thirty minutes from vibrant Hudson, with Amtrak service to New York City

Welcome to Wilbor Farmhouse, a circa 1875 Victorian on 1.4 acres in the historic hamlet of Old Chatham. A wraparound covered porch, decorative wood brackets, and custom shutters give the house its period charm, and original wide-plank pine floors carry that history inside. Fully restored from top to bottom, the 2,267-square-foot home offers three bedrooms, 2.5 baths, and a large yard, ready for full-time living or long country weekends. Deep bay windows pour light into the formal living room, and the dining room opens to a sitting room warmed by a wood stove, a space that could easily become a first-floor primary bedroom. The new kitchen is built around a farmhouse sink and a Wolf range, with Bosch appliances, quartz counters, and custom solid wood cabinetry, and it steps out to a new deck for summer dinners. Upstairs, the primary bedroom looks toward the back of the property for privacy, and a walk-in dressing room leads to a generous bath with a soaking tub and walk-in shower. A seco

Tucked away on 5 acres in the heart of Old Chatham, 14 Depot Lane is a one-of-a-kind private retreat shaped by stone, water and the character of an old house that has evolved over time. Set along a wooded ridgeline, the home is surrounded by rock outcroppings, mature trees and natural landscaping, with a creek and waterfall forming a natural border of the property. It all feels wonderfully secluded yet connected to the community around it. Inside, 2,600+ sq ft is filled with warmth, texture and unique architectural details. The eat-in kitchen is a standout with wood cabinetry, tiled countertops, terracotta floors, exposed beams and a wood-burning fireplace hearth. An oversized picture window frames the rock garden, bringing the natural setting in. The dining room has its own fireplace and barrel-shaped ceiling, with doors from both the kitchen and dining room opening to a large rear deck nestled among the treetops. A spacious living room with vaulted ceiling flows into an open study, w

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

Almost completely-refinished 3BR/2BA home on two acres within walking distance of Old Chatham Square. There are a few things on the punch list remaining inside and out, but this 1870 two story plus walk-out basement home is now effectively a 2020s home. After being brought down to the studs, it was rewired, replumbed, and finished with new windows and doors. Foam insulation was installed before the sheetrock went up, ensuring a tight home keeping sound out (I90 is nearby) and heating and cooling in (home comes with a central air compressor awaiting installation) All flooring, tiling, appliances and lighting as well as the gas furnace is less than five years old. Buyer will need to arrange for final inspections from the town building department to get a Certificate of Occupancy but, the extra effort will be well worth it

Charming ranch set on a level lot along County Route 32 in North Chatham. This 3-bedroom, 1-bath home offers hardwood floors throughout the main living areas, a bright living room that flows into a formal dining room, and a functional eat-in kitchen with ample oak cabinetry. Three comfortable bedrooms and a full bath round out the main level. Enjoy the outdoors from the deck overlooking the backyard, complete with a screened gazebo. Perfect for morning coffee or evening entertaining. An attached two-car garage and full unfinished basement provide plenty of storage and potential for future finished space. Recent updates include a whole-house water softener and filtration system (2025) and brand-new water heater(2026). Set on just under an acre, this is a solid opportunity in the Hudson Valley, minutes to shopping, dining, and the Taconic State Parkway

Historic Charm, Flexible Opportunity in North Chatham. Discover the character and possibilities of this charming three-bedroom, two-bath home, dating to approximately 1830 and set on a little over two acres in the picturesque hamlet of North Chatham, NY. Offering a unique blend of historic appeal, usable land, and flexible space, this property presents an opportunity for both residential living and income potential. Currently, 200 square feet of the house is leased to the U. S. Post Office, creating an established rental component while leaving the main three-bedroom residence available for additional rental space or personal use. For those seeking a full-time residence, there is also the opportunity to reimagine the entire property as a private primary home, subject to any applicable approvals. Whether you're looking for an investment property, a home with supplemental income, or a distinctive country residence with room to make it your own, this North Chatham property offers a rare c

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 open studio w/loft w/half-bath 850 dollars/mth. All photos pre-occupancy. No interior liquor store photos. Tenants must approve all showings and give access. 48HR notice minimum. By appt only. Agents pls use ShowingTime

Room to Spread Out in a Country Setting Priced $95 K below Assessed Value for a Quick Sale! Making it a great opportunity/investment This inviting home offers four bedrooms, two full baths, and flexible space for an in-law setup. A main-floor bedroom ensuite adds convenience, living room attaches to the oversized kitchen, that opens to the dining room, & walk out the back deck and enjoy views of the spacious backyard. Downstairs, a cozy living room with a fireplace creates a welcoming place to unwind, or walk out and gaze over your sprawling back patio. Take a few more steps down and enjoy the In-Apartment with three more bedrooms and a full bath, kitchen and Laundry The property features 3 yr old electric split-system heating/ AC, 4 car garage and is conveniently located near Lebanon Valley Speedway. Close the Berkshires and the Capital District with easy access to shopping and work

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

Historic Charm, Flexible Opportunity in North Chatham! Discover the character and possibilities of this charming three-bedroom, two-bath home, dating to approximately 1830 and set on a little over two acres in the picturesque hamlet of North Chatham, NY. Offering a unique blend of historic appeal, usable land, and flexible space, this property presents an opportunity for both residential living and income potential. Currently, approximately 200 square feet is leased to the U. S. Post Office, creating an established rental income while leaving the main three-bedroom residence available for rental or personal use. For those seeking a full-time residence, there is also the opportunity to reimagine the entire property as a private primary home, subject to any applicable approvals. Whether you're looking for an investment property, a home with supplemental income, or a distinctive country residence with room to make it your own, this North Chatham property offers a rare combination of histo

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 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

Seven vehicle spaces, over five acres, and your own private retreat: Car enthusiasts, hobbyists, and anyone craving room to spread out, this unique property deserves a closer look! Set on approximately 5.3 picturesque acres, this one-of-a-kind property offers a rare combination of garage space, flexible living areas, and outdoor amenities that make everyday living feel like a getaway! The standout feature? Exceptional vehicle capacity, including an attached garage and a substantial detached, insulated garage with electricity, ideal for those who need space for vehicles, equipment, projects, or hobbies! And there's so much more. Enjoy summer days by the inground pool, entertain poolside, or simply unwind surrounded by beautiful, mature landscaping. The grounds feature a greenhouse, fruit trees, grape arbor, pool house, and basketball court, offering plenty of room to enjoy the outdoors. Inside, cathedral ceilings and flexible living spaces offer room to work, create, relax, and make the

East Chatham (Canaan) Starter Home with all the I wants! Sop Close to the Berkshires Ski Resorts, Takonic PKWY Lee Ma, Remodeled 3 Bedrooms 1.5 Baths w/ Open Bright Spacious Living Space, Enclosed Heated Rear Porch w/Laundry Washer & Dryer All New Appliances, Beautiful Lighting, Full Basement New Roof Windows, Electrical Box, Septic System, Bathrooms & Kitchen, Come Home Relax on this Country Style Front Porch! Enjoy Life! 22 Mins to Albany & 23 mins to Lee Mass 1st Exit Off Taconic in Canaan NY Enjoy this Country Charmer for many years

A rare opportunity to own two residences on 42.73 beautiful acres! Enjoy a park-like setting with a picturesque pond, abundant wildlife and plenty of privacy. The 1,800+ sq ft main home offers 2 bedrooms, 2 full baths and an inviting great room with vaulted ceilings, wood-burning fireplace and wide-plank hardwood floors. The open layout flows into the kitchen with cherry cabinetry, dining area and light-filled solarium. Relax on the deck overlooking the pond or enjoy a snowy morning with coffee in the sun porch. Large 2 car garage and large full basement. Tucked away in the back of the property is a second, private residence featuring 1 bedroom plus an office. Ideal for multigenerational living, in-law residence, guests or rental income potential of 1,300+/month! It has also the potential to be used for a home business. The main parcel consists of 4.16 acres, with an additional 38.57-acre separately deeded building lot included (Tax Map #221.6-13.11). Keep the acreage together for your

Tucked away in a peaceful, private setting surrounded by woods, this charming 3 bedroom home offers the simplicity of one level living and a wonderful place to call home. Hardwood flooring flows throughout, while the spacious bedrooms and eat-in kitchen offer comfortable everyday living. At the heart of the home is a beautiful double sided fireplace shared between the kitchen and living room, creating a warm and inviting space to gather. Surrounded by nature, the property offers a sense of peace and tranquility, your own little oasis away from the hustle and bustle. A large unfinished basement and attached one-car garage provide additional space and convenience. While the home could benefit from some updating, it has great bones, plenty of character, and so much potential. A home that has been enjoyed over the years, now ready for its next chapter and someone new to make it their own. Improvements include a Generac generator (2020), 275-gallon oil tank (2019), Bilco door (2019), plumbi

Welcome to this charming 1850 post-and-beam country retreat set on 5 peaceful acres in the heart of East Chatham. Rich with character and surrounded by nature, this inviting 2-bedroom home blends historic warmth with flexible modern living-perfect for full-time residents, weekenders, and anyone seeking a creative escape minutes from the Berkshires. Inside, exposed beams, wide plank floors, and sunlit rooms create an atmosphere that feels instantly grounding. The layout offers comfortable everyday living with opportunities to personalize through light cosmetic updates, allowing buyers to add their own style without taking on major renovation projects. A standout feature of this property is the detached, heated'bungalow/flex space', equipped with 50-amp service and electric baseboard heat. This versatile building is ideal for an art studio, private office, home gym, wellness space, or a remote-work retreat-a rare amenity that expands how you live, create, and work. Outside, the acreage o

This property, located just outside Chatham Village presents an opportunity for a new owner. The half. Acre parcel borders Borden Pond Land Conservation Area and there is the potential to either renovate the existing home or build a new one. The house is being sold'AS IS. The property includes a well, and the septic system was replaced in May 2023

Excellent opportunity to own a mixed use property in a highly visible location on Route 20 in the Village of Nassau. Offering great exposure and easy access, this property is ideal for a variety of retail or service businesses, and includes 2 apartments as well. The building was extensively rehabbed in 2008 and features both an upstairs and downstairs income-producing apartment, providing an excellent opportunity for additional rental income. Why pay rent when you can own your own business location, build equity, and generate rental income at the same time? A great opportunity for an entrepreneur or investor looking to make a smart move!

Cedar hill. Architectural Country Living at its Finest. Is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York's historic Hudson Valley. The home engages seamlessly with its natural surroundings through walls of glass that draw in the changing seasons. From spring's first blooms and summer's golden light to autumn's rich palette and the quiet beauty of snow-covered peaks. Abundant natural light and warm finishes create interiors that balance architectural precision with a sense of comfort and ease. The grounds include a 50-foot heated in-ground Gunite salt-water pool and spa, surrounded by expansive bluestone patios. Thoughtfully positioned just beyond, a cedar-clad spa pavilion. With sauna and custom sleek st

First time Homebuyers will love this home. On a Valatie Village street you will find this two story house with two bedrooms on the upper floor, open kitchen, dining area/living room and a full bath. The lower floor has a home office or a den/guest room, half bath, utility room and a two car garage. Then you walk out the back door and you are in a different place. Full two story deck/porch looks over the private back yard with barn and sheds. Village water and sewer. Take a walk on the village sidewalks to the ballfield and all the shops and restaurants

Cedar hill. Architectural Country Living at its Finest. Is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York's historic Hudson Valley. The home engages seamlessly with its natural surroundings through walls of glass that draw in the changing seasons. From spring's first blooms and summer's golden light to autumn's rich palette and the quiet beauty of snow-covered peaks. Abundant natural light and warm finishes create interiors that balance architectural precision with a sense of comfort and ease. The grounds include a 50-foot heated in-ground Gunite salt-water pool and spa, surrounded by expansive bluestone patios. Thoughtfully positioned just beyond, a cedar-clad spa pavilion. With sauna and custom sleek st

Spacious 4 bedroom, 2.5 bath, 2240 square foot Colonial sitting on just under an acre in the Bonnie Lea Estates neighborhood of Valatie. At the heart of the home is a large sunny renovated kitchen featuring butcher block countertops, an induction range and stainless appliances. A peninsula breakfast bar divides the kitchen and a cozy sitting room, anchored by a brick wood burning fireplace. This is exactly where everyone will want to gather. Glass door leads out to the patio where there's plenty of space for your grill and smoker plus a dining area under the gazebo. Beyond the patio is a large backyard with tall hedgerows on 2 sides providing privacy. Fenced garden, a fire pit circle and still plenty of space to add a pool. Back inside, a formal dining room sits on the other side of the kitchen which flows around to the spacious living room in the front of the house. Rounding out the main level is a foyer, laundry room with half bath, and an attached two car garage. Hardwood floors thr