Chatham Homes under $600,000

Welcome to Chatham, New York – a charming village nestled in the heart of Columbia County, where community spirit and educational excellence come together to create an ideal environment for families. The Chatham Central School District is renowned for its commitment to fostering a nurturing and stimulating learning atmosphere. With a strong emphasis on academic achievement, the district offers a range of programs designed to meet the diverse needs of its students, from early childhood education to advanced placement courses in high school.

Chatham's dedicated educators and staff work tirelessly to ensure that every child reaches their full potential, making this school district a top choice for families seeking quality education. The district also prioritizes extracurricular activities, providing students with opportunities to explore their interests and develop essential life skills outside the classroom.

For those considering a move to this picturesque area, Chatham offers a variety of homes under $600,000, making it an attractive option for first-time buyers and growing families alike. Whether you're looking for a quaint cottage, a spacious family home, or a charming historic property, the real estate market here has something for everyone.

Living in Chatham means enjoying not only a strong sense of community but also access to beautiful parks, local shops, and delightful dining options. With the stunning backdrop of the Hudson Valley, residents can enjoy outdoor activities year-round, from hiking and biking to winter sports.

Discover the perfect blend of education, community, and natural beauty in Chatham, NY – where your dream home awaits!

Newest Chatham Homes under $600,000

$320,000

4 Beds ⋅ 3 Baths ⋅ 202629658 MLS

**NOT A DRIVE-BY!** Discover the space, privacy, and convenience of Village of Chatham living! Tucked away on a quiet dead-end street, this remarkably spacious 4-bedroom, 3-full-bath home with a den offers so much more than meets the eye. Beautifully maintained and in fantastic condition, the home features a primary suite, newer flooring, granite countertops, stainless steel appliances, and a roof just 5 years young. The versatile floor plan includes a spacious mudroom and a fully finished walkout basement featuring a large family/recreation room plus two additional flexible rooms ideal for home offices, hobbies, or guest accommodations. Enjoy outdoor living on the expansive two-level deck overlooking a lovely yard, plus convenient off-street parking. All this in a desirable Chatham Village location, just minutes from Main Street's charming shops, restaurants, cafés, and local entertainment. Enjoy the peaceful setting of a tucked-away neighborhood with the convenience of village amenities nearby. Located in Columbia County, NY, this move-in-ready home delivers exceptional space, versatility, and location. **Much larger than it appears—this one truly must be seen to be appreciated!** none

15 Maiden Lane, Chatham

$519,000

3 Beds ⋅ 1 Baths ⋅ 202628567 MLS

Modest and unassuming from the front but bright and expansive in the rear, this old mill home dating back to 1878 offers a surprising amount of space across 1800 square feet. Like many old mill homes in the area, this one has been expanded several times over the past 150 years and is now a bright, light filled home with 3 bedrooms, 1 bath, hardwood floors, open kitchen, 1st floor den/office, and 2nd floor flex room. Although there is currently only 1 large bathroom, there is space to add a 2nd bath on the 2nd floor. This home has been meticulously cared for by the same family since 1974 and is ready for its next chapter. You'll enter thru the 3 season porch off the driveway and come into a large tiled foyer/mudroom before stepping down into the open kitchen, dining and living area. An entire corner of windows and skylights fill this space with light. Step out onto the large party deck right off the kitchen and dining room and enjoy the expanded living space in the summer months for dinner parties, BBQs, and stargazing at night. The back yard is private, spacious, mostly level, and gets lots of sun. Plenty of space for a garden and/or a pool. Across the yard, you'll see the large 2 bay garage and 2 story converted barn sitting at the rear of the 1 acre property. This building is insulated, has propane heat and power and was previously used as a workshop but could easily be finished for an office or art studio or even additional living space. An antique outhouse sits behind it. The rear of the property abuts the rail line, but don't let that deter you. There are no crossing nearby, so horns are rare and the trains have to move pretty slowly as they approach the bridge over Pond Hill Rd. Only 1.5 miles to Main Street Chatham with its charming shops, restaurants, Crandell Theatre, the future Shaker Museum and only a 3 minute drive to The Chatham Berry Farm and Greenhouse Cidery in the other direction. 27 minutes to Hudson Amtrak station and 30 minutes to Albany.

42 White Mills Road, Chatham

$339,800

3 Beds ⋅ 2 Baths ⋅ 202628228 MLS

1st Open House Sunday October 18 1-3PM!! 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.

1169 NY-295, Canaan

$549,000

3 Beds ⋅ 3 Baths ⋅ 202627870 MLS

Set on 5 serene acres, this bright 3 bedroom, 3 bath residence offers generous room sizes and a peaceful, private setting within a short bike ride of town. The home features a woodstove fireplace in the dining area and a 3 flue chimney ready for a second fireplace. A full length deck spans the entire home, inviting outdoor living and quiet enjoyment. The substantial 34x24 detached building provides exceptional potential for a studio or additional workspace. A property with light, privacy, and versatile amenities. Presently the young grand daughter is in process of moving .. be ready to see boxes and the like - otherwise an exceptionally beautiful home. Occupants require 24-48 hour notice minimum. Note actual vs AI Enhanced photos. Central A/C and automatic whole-house generator among amenities.

341 White Mills Road, Valatie

$399,000

3 Beds ⋅ 2 Baths ⋅ 202627783 MLS

Move-in ready with a fully renovated interior for under $400K! This beautiful three-bedroom, two-bath ranch on a one-acre lot delivers exceptional value. The interior is completely updated, featuring a bright, modern kitchen with quartz countertops and all-new stainless-steel appliances, plus the everyday convenience of main-floor laundry with a brand-new washer and dryer. Downstairs, an enormous unfinished walkout basement pairs perfectly with the attached oversized two-car garage-both offering incredible storage and potential. Nestled in a highly convenient corridor, this turn-key home is just 10 minutes from the Taconic State Parkway, 15 minutes from downtown Hudson and the Amtrak station, and an easy commute to Albany and the Berkshires. Enjoy the very best of local culture right around the corner. Spend your weekends exploring Art Omi, catching a show at the Ghent Playhouse, or visiting the Hudson-Chatham Winery. Grab morning coffee and fresh scones at the historic Bartlett House, or pick up local goods at the Liberty Farms Organic Farm Store. With the diverse dining and shopping of both Hudson and Chatham just 10 to 15 minutes away, you get the perfect balance of country peace and vibrant town life. Enjoy the peace of mind of an updated home with endless potential and unmatched convenience. All you have to do is move in!

1941 State Route 66, Ghent

$262,900

3 Beds ⋅ 1 Baths ⋅ 202620053 MLS

Imagine a crisp autumn morning, dew still resting on the ground. You step onto your front porch with a warm beverage in hand and take in the peaceful beauty of the surrounding countryside. For a few quiet moments, it's simply you and nature. As the cool air settles in and your drink begins to lose its warmth, you head back inside, where the woodstove keeps the living room cozy and inviting. Wander into the kitchen, finish making breakfast, and settle in to enjoy your morning in the comfort of home. Situated on approximately one acre, this three-bedroom, one-bath home offers the country setting you've been looking for while keeping you within reach of everyday destinations. East Chatham provides convenient access toward the Massachusetts border and the Berkshires, including the Pittsfield and Stockbridge areas, while Albany, Troy, and East Greenbush are also within driving distance. After a long day, pull into the attached basement garage and leave the outside world behind. As you walk up the stairs from the garage into the kitchen, the inviting aroma of the meal you left simmering in the crockpot all day welcomes you home. Relax to the sounds of nature, enjoy a refreshing shower in the updated bath, and settle in for a comfortable evening at home. Whether you're enjoying the brilliant colors of autumn, the warmth of the woodstove on a chilly day, or the peaceful surroundings of your own acre, 43 Frisbee Street offers a place to slow down, settle in, and feel at home. Welcome to 43 Frisbee Street--cozy, comfortable, and close.

43 Frisbee Street, Chatham

$469,000

3 Beds ⋅ 2 Baths ⋅ 202619674 MLS

Surrounded by nature with 21 acres of private trails to roam. This architecturally striking 3BR/2BA home features a soaring cathedral-ceiling great room opening to a wrap deck, plus a lower-level hangout space perfect after a day outdoors. Central air, efficient propane systems, and an oversized 2-car garage make it easy to enjoy in every season. Minutes to Queechy Lake, Chatham, Hudson, the Berkshires, and skiing just 15 miles away. A private retreat with huge redecorating potential -- ideal for year-round adventure or a high-demand AirBnB escape. Short notice showings possible. Fiber optic high speed internet. 35-year architectural shingle guarantee (6-10yrs left). Decks 4-5yrs old. Mailbox end of driveway.

3620 County Route 9, New Lebanon

$259,000

4 Beds ⋅ 2 Baths ⋅ 202615136 MLS

Tenants require 48hour notice to show and only after 10a.m. No Sunday showings preferred. All photos pre-occupancy. Easy living in this low-maintenance, fully renovated income home. Two two-bedroom apartments, each with refrigerator, range/oven, washer/dryer. MUNICIPAL WATER/SEWER. Covered front porch with a second-floor veranda above. Bright, happy home. Cable/High-speed internet available. 3 miles to Chatham Village/schools, 9 to Hudson/Amtrak, and a stroll to town park w/tennis courts, Bartlett House cafe and Dairy Queen. A wonderful small-town feel while being minutes from shopping and popular attractions, including bustling Warren Street, Chatham's Main Street, Omi, Hawthorne Valley Farm Store/School, libraries, MacHaydn and Crandell Theaters. Shown by Appt Only. Tenants require a minimum of 48-72 hours' notice.

2261 State Route 66, Ghent

$475,000

3 Beds ⋅ 2 Baths ⋅ 202613968 MLS

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.

1129 New York 295, Chatham

$289,000

3 Beds ⋅ 2 Baths ⋅ 202613554 MLS

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.

1135 New York 295, Chatham

$599,000

9 Beds ⋅ 6 Baths ⋅ 202610680 MLS

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. 48hour notice required to show. Buyer/Coop brokers must attend all appointments. Thank you for your interest. Tenants must approve and provide access.

1121-1123 New York 295, Chatham

$495,000

3 Beds ⋅ 2 Baths ⋅ 202530207 MLS

PRICE CHANGE!!! Newly remodeled from top to bottom. Well known area top builder is the owner. Beautiful flat lot, protected on one side by a conservancy. Move in and live maintenance free for many years. 3 beds, 2 full baths. One bed and bath on the first floor. Light and bright in every room. Basement fully insulated, whole house is energy efficient. Semi private but close to everything. Skiing, Berkshires, TSP, I90.

263 Old Hudson Turnpike, Canaan

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Chatham Homes under $600,000

Newest Chatham Homes under $600,000

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