Chatham Homes with Level Lot Description

Welcome to Chatham, New York, a charming village nestled in the heart of Columbia County, known for its picturesque landscapes and vibrant community spirit. One of the standout features of the Chatham area is its exceptional school district, which is dedicated to fostering a nurturing and academically rigorous environment for students. The Chatham Central School District prides itself on its commitment to excellence, offering a well-rounded curriculum that includes a variety of extracurricular activities, advanced placement courses, and supportive resources for students of all ages. Parents can feel confident that their children are receiving a top-notch education in a safe and engaging atmosphere.

In addition to its outstanding educational offerings, Chatham boasts an array of beautiful homes, many of which feature level lots—ideal for families looking for outdoor space to play and entertain. These properties provide a perfect canvas for gardening, recreational activities, or simply enjoying the serene surroundings. The level lots make maintenance easier and provide a safe environment for children and pets to roam freely.

Living in Chatham means enjoying the best of both worlds: a close-knit community with a rich history and access to modern amenities. Residents can take advantage of local parks, shops, and cultural events that bring the community together. Whether you’re a first-time homebuyer or looking to settle down in a peaceful area, Chatham offers a unique blend of charm, quality education, and beautiful homes with level lots that make it an ideal place to call home. Come discover the magic of Chatham, where your dream home awaits!

Newest Chatham Homes with Level Lot Description

$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

$3,595,000

6 Beds ⋅ 5 Baths ⋅ 202628091 MLS

A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room--an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished attic and an impressive 4,500-square-foot barn with foosball and ping pong provide additional flexible space for leisure and gathering. Fiber-optic internet and a full-house generator ensure seamless modern living, while the estate's thoughtful infrastructure and meticulous maintenance support effortless year-round ownership. Bellavista stands as a premier private estate, offering a rare combination of total privacy, exceptional amenities, and enduring quality. Just minutes from Chatham, Hudson, and Kinderhook--and a short drive to Lenox, Stockbridge, and Great Barrington--the property is surrounded by acclaimed farm-to-table dining, art galleries, organic markets, and the historic Crandell Theater. Easily accessible via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport, Bellavista is as convenient as it is extraordinary.

147 Rock City Road, Chatham

$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

$699,000

3 Beds ⋅ 3 Baths ⋅ 202623239 MLS

Tucked away at the end of a long approach and surrounded by 13.24 acres of pure Hudson Valley beauty, this exceptional A-frame retreat offers the ultimate escape for those seeking peace, privacy, and a connection to nature. Whether you're searching for a full-time residence or a weekend sanctuary, this property delivers the perfect blend of rustic charm and modern comfort. The dramatic great room is the heart of the home, featuring soaring cathedral ceilings, walls of glass that frame the changing seasons, and a stunning stone fireplace with a wood stove insert that creates the perfect gathering place after a day outdoors. The chef's kitchen is thoughtfully designed with a gas cooktop, built-in double ovens, Hi-Mac solid surface countertops, and generous workspace for entertaining. The adjoining dining area is surrounded by oversized picture windows, bringing the outdoors in with breathtaking woodland views. Convenient first-floor living includes a spacious bedroom, full bath, and laundry/mudroom--ideal after hiking your own trails or tending the property. Upstairs, a loft overlooking the great room makes an inspiring home office, reading retreat, or cozy TV lounge. The private primary suite features an en suite bath and a charming Romeo & Juliet balcony where your morning coffee comes with birdsong and uninterrupted views of nature. The finished walk-out lower level expands the living space with room for guests, recreation, or movie nights, complete with a built-in bar ready for serving craft cocktails after a day of exploring the countryside. Step outside to the expansive wrap-around deck and experience the true magic of this property. Watch deer wander through the trees, listen to the breeze rustle the leaves, and enjoy complete seclusion in every season. A whole-house generator provides peace of mind year-round, while the detached metal garage offers abundant space for vehicles, tractors, outdoor equipment, and hobbies. A must see!

2640 New York 203 Stop 1, Kinderhook

$1,950,000

4 Beds ⋅ 3 Baths ⋅ 202623153 MLS

Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom home captures breathtaking, uninterrupted views of the Catskill Mountains and Hudson Valley, with spectacular sunsets, endless skies, and exceptional stargazing. Designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, butler's bar, and custom cabinetry by renowned Vormer Cabinetry of Hillsdale. High-performance Pella windows frame the panoramic views, while a dramatic stone fireplace with a reclaimed wood mantel anchors the great room. A marble gas fireplace adds warmth to the den. The primary suite enjoys stunning views and includes a spa-inspired bath, laundry, and generous closet space. A spacious two-car garage offers abundant storage for outdoor gear, perfectly complementing the property's proximity to Queechy Lake, Stockbridge Bowl, and year-round recreation. Smart home features include app-controlled security cameras and HVAC. Expansive decks and patios overlook the mountains, complemented by multiple fire pit and grilling areas, a heated saltwater pool, and a charming pool house with its own outdoor kitchen patio. The walkout lower level opens to an additional stone patio and fire pit. Raised garden beds, ornamental gardens, and fenced vegetable gardens with programmable drip irrigation complete the landscape. Flexible living space provides additional guest accommodations, and a whole-house generator offers year-round peace of mind. An additional five-acre parcel is included, offering the opportunity to build a guest house, studio, or office (subject to approvals). Located on privately maintained roads, this exceptional retreat offers privacy just minutes from Chatham, Hudson, and the Berkshires, with easy access to acclaimed dining, shopping, cultural destinations including Tanglewood and Jacob's Pillow, the TSP and NYC.

116 Ridge Road, Canaan

$699,000

202622779 MLS

Imagine serving dinners lakeside or welcoming boaters to one of the docks for a refreshing lemonade!! This is the amazing opportunity that awaits one's vision in reviving the nostalgic Backwater Grill restaurant on beautiful Queechy Lake - one of the most pristine lakes in New York state. Here sits an opportunity to cater to the residents surrounding Queechy Lake or visitors to the Hudson Valley and Berkshires. Architectural drawings are in place showcasing the layout of the kitchen, dining area and lounge. A second-floor space includes additional room for storage and an office. The gem of the design, however, is the outdoor dining deck poised on the edge of the lake. Careful work has been done to design a septic system to handle the needs of the restaurant with special consideration given to the sensitivity of being on the lake. Both DEC and the Columbia County Board of Health have approved the design with estimates for installation in place. With so much of the planning work already completed, it's time to put ''hammer to nail'' and bring an all new Backwater Grill back to the anticipating public. It's also an opportunity to compliment the work and vision taking place up the road at the former Queechy Lake Motel. What a dynamic duo for Canaan and the visiting public has never been so fortunate!

42 Queechy Lake Drive, Canaan

$485,000

202620005 MLS

Buyers don't miss out on this one. If looking to build your dream home or a hunting enthusiast , you have found a private country property located near a quiet historic community . Just minutes to the N.Y.S Thruway & Taconic State Parkway and an easy drive to NYC or a short drive to the Berkshires for all seasonal activities. After storing the recreational vehicles, enjoy the wildlife along side a quiet stream. Both of these tax parcels 102689 47-1-8 ( 43.1 ) & 102689 47-1-9 ( 20 acres ) are to be sold together.

L8 Lower Cady Road, 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

2 Baths ⋅ 202613557 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 NY-295, Chatham

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Chatham Homes with Level Lot Description

Newest Chatham Homes with Level Lot Description

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