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L53 New York 66, Chatham
$150,000
202623288 MLS
Discover the possibilities on this 15.5-acre parcel in the desirable hamlet of Malden Bridge. Once home to grazing dairy cows, this open and fertile land is ready for its next chapter. Whether you're looking to start a small farm, establish a homestead, raise livestock, grow crops, or simply invest in agricultural land, this property offers plenty of opportunity. The gently rolling landscape provides ample open space with room to bring your vision to life. Conveniently located just minutes from I-90, you'll enjoy easy access to the Capital Region, the Berkshires, and the Hudson Valley, making commuting and transporting equipment a breeze. Please note there is highway noise from nearby I-90, and a cell tower is located close to the property. These factors are reflected in the asking price, creating an excellent value for buyers seeking affordable acreage in a convenient location. Bring your ideas and discover the potential this Columbia County property has to offer.

L53 New York 66, Chatham

140 Presbyterian Hill Road, Stephentown
$229,000
3 Beds ⋅ 2 Baths ⋅ 202620624 MLS
Charming Stephentown Cape Cod: Country Living Near Jiminy Peak! Embrace the peace of country living in this charming 4-bedroom, 2-bathroom Cape Cod home set on over an acre of beautiful land. Inside, you will find warm, inviting knotty pine paneling and a classic country eat-in kitchen. The highly flexible floor plan currently utilizes two bedrooms as a dedicated home office and a convenient laundry room. Step outside to enjoy your private back deck, relax around the firepit, or utilize the two-car garage. Located just minutes from Jiminy Peak Ski Area, Cherry Plain State Park, and the cultural attractions of Western Massachusetts, this property offers the perfect blend of rural tranquility and outdoor adventure. Showings start Monday 6/29 by appointment only.

140 Presbyterian Hill Road, Stephentown

13247 NY-22, Canaan
$295,000
2 Beds ⋅ 1 Baths ⋅ 202619811 MLS
Welcome to ''The Meadow Lodge'' ... Authentic Upstate New York log home living begins here. Set among mature trees, open lawn, andbeautifully improved grounds, this meticulously maintained Canaan retreat is a perfect balance of privacy, character, and convenience. Ideally situated between Hudson and the Berkshires, you'll enjoy easy access to the restaurants, galleries, boutiques, and cultural destinations that have made this region one of the Northeast's most sought-after escapes. Spend the day exploring Hudson's vibrant Warren Street, attending performances in Lenox, strolling the charming streets of Stockbridge, or enjoying the lakes, trails, farm stands, and hidden gems that define Columbia County living. Lovingly cared for and extensively updated, the property has benefited from substantial improvements including a newer metal roof, driveway, drainage and foundation work, exterior re-staining, re-caulking of all log joints, replacement windows, refinished lower-level space, and numerous structural upgrades throughout. A detached barn-style garage with a poured concrete foundation adds tremendous versatility, while the spacious loft above offers exciting potential for an artist's studio, home office, wellness space, workshop, or future expansion. Approximately one acre of overgrowth was cleared to create a more open and inviting landscape, complemented by a handsome stone wall and thoughtfully maintained outdoor spaces. A future outdoor shower hookup is already in place, perfect after a day spent at nearby Queechy Lake. Rich in character and thoughtfully improved, this is the kind of property buyers envision when searching for a refined country retreat. A place where log home charm, natural beauty, and the best of the Hudson Valley and Berkshires come together in one exceptional offering.

13247 NY-22, Canaan

11 Kinderhook Lane, New Lebanon
$325,000
3 Beds ⋅ 2 Baths ⋅ 202617508 MLS
Charming 1980s one-floor ranch set back from a quiet country road. This bright home features an oversized eat-in kitchen, 2-3 bedrooms, (one presently the laundry room) and a main bedroom with a convenient half-bath. The living room is filled with natural light from abundant windows. Vinyl plank flooring throughout most of the home and a huge heated basement provide comfort and flexible space. Outside offers a nice, flat yard with a covered love-seat swing, plus a Generac whole-house generator for peace of mind. Attached 2-car garage is electric/oil heated and accessed via a paved driveway. Location highlights: private country road (not a thoroughfare), close to the Berkshires, Lebanon Valley Speedway, Taconic Park (TSP), and I-90.

11 Kinderhook Lane, New Lebanon

2025 Us Highway 20, Nassau
$133,000
2 Beds ⋅ 3 Baths ⋅ 202610950 MLS
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.

2025 Us Highway 20, Nassau

25 Rockledge Road, Canaan
$1,125,000
3 Beds ⋅ 4 Baths ⋅ 202616604 MLS
Open House 5/30 12:00-2:30!!! Welcome to this one-of-a-kind mountain oasis with breathtaking views of the Taconic Range. Set on 10 private acres, this extraordinary upstate retreat features a stunning 3,768 SF custom lodge-style home, a 3-car garage with a private guest suite, an in-ground pool with pool house, and an additional 2-car garage. The main residence blends rustic elegance with modern comfort, offering 3 bedrooms, including both a first-floor primary suite and a second-floor primary suite, 3.5 baths, a gourmet kitchen, multiple wood-burning fireplaces, and a spacious family/media room designed for both relaxing and entertaining. Step outside to your own resort-style setting complete with sweeping mountain views, a fire pit, koi pond, and in-ground pool -- the perfect backdrop for relaxing or hosting guests year-round. What truly sets this property apart is its incredible versatility and income potential. In addition to the main home, the property includes a fully equipped 2-bedroom guest/pool house and a private 1-bedroom guest suite above the 3-car garage, each featuring its own living space, fireplace and kitchen. Whether you're searching for a multi-generational compound, luxury retreat, or investment opportunity, the possibilities are endless. Perfectly suited for short-term rental opportunities such as Airbnb or VRBO, this unique property offers the ability to offset expenses while enjoying luxury living in one of the region's most scenic settings. To think this property couldn't get any better, it does with Deeded Lake rights to Queechy Lake (8min drive away). Conveniently located just 14 minutes to the Taconic Parkway, 20 minutes to Jiminy Peak Mountain Resort, 24 minutes to Tanglewood, and 18 minutes to Chatham, this exceptional property offers the perfect balance of privacy, convenience, lifestyle, and investment potential. A rare opportunity to own an extraordinary mountain retreat in one of the area's most scenic and sought-after locations.

25 Rockledge Road, Canaan

186 W Hand Hill Road, New Lebanon
$381,500
3 Beds ⋅ 3 Baths ⋅ 202619721 MLS
186 Hand Hill Rd W offers a rare level of privacy and refinement at the end of a quiet, town-maintained road. A private drive leads to a bluestone walkway and understated entry. This Colonial-style residence is thoughtfully sited to capture uninterrupted views of a private pond, with expansive front-facing windows that draw in natural light throughout the day. The landscape shifts beautifully with the seasons, always anchored by the water. The interior is balanced and composed, with two masonry wood-burning fireplaces defining the main living spaces. The layout flows with ease, suited for everyday living. The primary bedroom is oriented toward the pond, creating a quiet, restorative retreat. While the formal dining room offers a perfect gathering space. The rear deck extends into the surrounding woods, enhancing the sense of privacy. The 5-acre parcel includes raised garden beds and established plantings. Directly bordering the 447-acre Hand Hollow Conservation Area, the property offers protected views, lasting privacy, and access to an expansive network of trails and natural landscape. Convenient to Albany, the Berkshires, Tanglewood, and regional skiing. It's all awaiting your visit

186 W Hand Hill Road, New Lebanon

331 Ashley Hill Road, Chatham
$369,900
3 Beds ⋅ 1 Baths ⋅ 202618940 MLS
Welcome to this charming 3-bedroom, 1-bath ranch nestled in the heart of Columbia County. Beautiful flower beds with winding stone pathways and a welcoming front porch create the perfect first impression. Inside, natural sunlight fills the home, highlighting the spacious dining area and inviting living room featuring a cozy wood-burning stove. The kitchen is equipped with an induction cooktop, stainless steel refrigerator, built-in oven, dishwasher & pantry with pull out shelves. Step outside to take in the breathtaking mountain views and endless greenery that surround the property. The expansive 32 ft long deck provides the perfect setting for relaxing or entertaining year-round while enjoying the peaceful scenery. If you've been searching for tranquility, comfort, and stunning views, this is a home you won't want to miss. There are newer Anderson double pane windows, and an awning on the back deck, Schedule your showing today!

331 Ashley Hill Road, Chatham

626 Garfield Road, Stephentown
$670,000
3 Beds ⋅ 3 Baths ⋅ 202613205 MLS
Set amid the rolling countryside of East Nassau, this property presents a rare opportunity to own a private retreat spanning 45 breathtaking acres of fields, woods, and water. Thoughtfully positioned to capture the tranquility of its surroundings, this property offers the perfect balance of comfort, recreation, and natural beauty. The home features 3 bedrooms and 3 full bathrooms, with a full bath on each level, offering flexibility for guests and everyday living. Inside, approximately 2,300 square feet of living space is complemented by a finished walkout basement with a large family room, dedicated office, pantry, utility space with substantial additional storage--ideal for remote work, hobbies, or entertaining. The primary bedroom includes a walk-in closet and first floor laundry. Recent improvements enhance both efficiency and peace of mind, including a new architectural shingle roof installed in 2024 and major system updates completed in 2022. The home is equipped with central air conditioning, a 16kW whole-home generator, and a water softener system, ensuring comfort year-round. Outdoors, the property transforms into a private sanctuary. Spend warm summer days by the 18' x 33' above-ground pool, or unwind in the screened-in gazebo overlooking the serene landscape. The land itself is truly exceptional, featuring two picturesque ponds--one with its own private island--as well as a trout stream, creating a setting that feels more like a nature preserve than a backyard. Additional amenities include a powered shed with 30-amp service and a separate hunting cabin with 100-amp electric and potential septic and water hookups, offering endless possibilities for recreation, guests, or future expansion. Welcoming blueberry bushes and seasonal flowers greet you at the entrance, setting the tone for a property that feels both peaceful and refined.

626 Garfield Road, Stephentown

126 Shaker Ridge Drive, Canaan
$1,900,000
7 Beds ⋅ 6 Baths ⋅ 202529436 MLS
Welcome to Cannondale Compound, a sprawling architectural residence with far-reaching mountain views. Designed for both gathering and privacy, the home features seven bedrooms across two wings, expansive decks and balconies, and both indoor and outdoor pools. A dramatic triple-height great room with fieldstone fireplace anchors the main wing, joined by a chef's kitchen, cozy living spaces, and a primary suite with fireplace and private balcony. The north wing offers an indoor lap pool, studio, and three-car garage. Recent upgrades include a new geothermal system, new flooring, and a new roof. Outdoors, enjoy a hot tub, pool house, garden, and treehouse, plus deeded Queechy Lake rights. Just minutes from Chatham, the Berkshires, and top Hudson Valley destinations.

126 Shaker Ridge Drive, Canaan

161 Horse Heaven Road, Stephentown
$255,000
2 Beds ⋅ 1 Baths ⋅ 202618183 MLS
Don't miss out on this 2 BR, 1 BA home on 11 acres in East Nassau in the Town of Stephentown in New Lebanon School District...a rare find under $250K! Enjoy privacy with wooded views in every direction on this quiet, country road located just 30 min to Albany NY and Pittsfield or Stockbridge in the Berkshires of MA. Jiminy Peak Ski Resort is 20 minutes away. It's less than 3 hrs to NYC, 2.5 hrs to Boston, and 1 hr to Saratoga Springs. Offers a 2 car detached garage, 4 sheds (one with electricity), and beautiful, private lawn spaces. There's lots of room for gardens or animals. This is a terrific property for a gentleman's farm! Features HW flooring in the combined LR/DR, and the eat-in kitchen was remodeled in 2011 including the appliances; the adjoining pantry offers additional storage and leads to the laundry room which has an exit to the back deck. The updated washer & dryer are included. Features built-in storage in both bedrooms, and an updated bathroom sink/vanity in the full bath. Offers a new oil tank in 2025, vinyl siding, updated roof approx 2013, septic tank updated 1981, new leach field in 2008, high speed internet, and a Generac generator. Showings start Sat 5/30.

161 Horse Heaven Road, Stephentown

287 Us-20, New Lebanon
$85,500
202522001 MLS
Discover the potential of this expansive 7.2-acre lot, ideally situated on Route 20 and moments before the Massachusetts line. Previously serving as a non-profit Kennel for dogs, this unique property offers versatility for both commercial and residential development. With a drilled well already in place, the lot is ready for your vision ~ whether you're looking to create a serene residential retreat or a thriving business venture. This property offers all the advantages and benefits of rural living but conveniently located between Albany and Pittsfield. Enjoy the convenience of easy access to major routes while embracing the tranquil surroundings. Don't miss out on this rare opportunity to invest in a property with endless possibilities!

287 Us-20, New Lebanon

15548 State Route 22, Stephentown
$265,000
3 Beds ⋅ 2 Baths ⋅ 202615654 MLS
Enjoy easy one-floor living in this well kept ranch set in a peaceful, scenic area surrounded by picturesque mountain views. This 3 bedroom, 2 full bath home offers a comfortable and functional layout with plenty of space to spread out. The primary suite includes its own full bathroom and double closets for added convenience and privacy. Two additional bedrooms are generously sized and could work well for guests or a home office. The spacious kitchen has been updated and offers plenty of cabinet space, making it practical for everyday cooking and storage. A full, unfinished basement provides great space for a workshop, hobbies, or additional storage. Out back, a covered porch with an awning gives you a comfortable spot to relax and take in the fresh air and surrounding scenery. If you enjoy the outdoors, this location is a great fit--set in a quiet area with mountain views and just a short drive to Jiminy Peak Mountain Resort for skiing and year-round recreation. A solid home in a idyllic setting, with the space and features that make everyday living easy.

15548 State Route 22, Stephentown

L67 Old Ghost Road Lot 6, New Lebanon
$92,500
202425654 MLS
Improved pricing and BOHA! A wonderful 11+ acre parcel sits at the end of a cul-de-sac on a quiet town road in Deer Ridge, off CR 5, whimsically named Old Ghost Road. If scenic country drives & private wooded trails are on your wish list, this secluded paradise could be your future home. The mostly wooded lot already has a driveway & numerous trails cut in, making it easy to explore & choose your ideal building site. With additional clearing, you'll enjoy far-reaching vistas & complete privacy. A seasonal stream & a lovely ravine—tucked far from the road—make for a perfect trail destination. Septic & well install will be the responsibility of the buyer. Electric service is already available on Old Ghost Road at the driveway. Come experience all this area offers.

L67 Old Ghost Road Lot 6, New Lebanon

439 Kelly Road, New Lebanon
$2,560,000
4 Beds ⋅ 3 Baths ⋅ 202522401 MLS
Introducing Mossford Estate, a historic country residence offered for the first time in 40 years. This 1800s Federal-style home sits on 144 acres and features an antique barn, tennis court, five fireplaces, and a private swimming pond. Inside, you'll find a formal living room, a generous dining room, a sunlit modern kitchen, and a dramatic double-height den evoking the warmth of a Ralph Lauren-style Adirondack lodge. Upstairs, the primary suite includes a fireplace and full bath, while a wide hallway with a charming reading nook leads to three spacious bedrooms and a third bath. Every room reflects the owners' meticulous attention to preserving and replicating 19th-century details. A stone patio, vegetable garden, and sweeping pastoral views complete the picture of refined country living.

439 Kelly Road, New Lebanon

28 Greenbrook Drive, Chatham
$575,000
3 Beds ⋅ 3 Baths ⋅ 202524836 MLS
Timeless country elegance best describes this charming custom-built Cape, set on 2.6 acres along the Green Brook in the Town of Chatham, just outside the hamlet of Malden Bridge. Built with craftsmanship and rich character, the home blends tradition with modern comfort, featuring solid wood doors, cherry hardwood floors, custom kitchen and lighting, tiled baths, and a welcoming living room with a fireplace. The residence offers multiple bedroom suites - 3 bedrooms and 3 baths, including a spacious primary suite with walk-in closet and ensuite, a guest bedroom with ensuite, and a flexible third bedroom. A large recreation room and studio above the two-car garage provide space for a home office, yoga, or creative pursuits, while the oversized, dry basement offers abundant storage or room for a gym, game room, or home theater. The kitchen is well appointed with stainless steel appliances, including a brand-new refrigerator, and the home is supported by a top-of-the-line Buderus furnace. Outdoors, mature shade trees and evergreens frame a private yard with a hammock and a trail leading to the creek, creating an ideal setting for quiet reflection or entertaining. Splendid landscaping enhances the natural beauty of the property, while the wooded setting offers both privacy and tranquility. Perfectly situated, the home is minutes from the historic hamlets of Old Chatham and Malden Bridge, with easy access to Hudson, Chatham, Pittsfield, Great Barrington, and the Berkshires. Albany International Airport, the Taconic Parkway, and I-87 provide direct routes to New York City and Boston, each just over two hours away. Year-round recreation abounds, from swimming and summer gatherings to brilliant fall foliage and winter skiing at nearby Catamount, Butternut, and Jiminy Peak. Cultural destinations such as Tanglewood, Jacob's Pillow, and Art Omi are also close at hand. This is a rare opportunity for gracious country living, whether as a full-time residence or a weekend retreat.

28 Greenbrook Drive, Chatham

187 West Street, New Lebanon
$500,000
3 Beds ⋅ 2 Baths ⋅ 202516895 MLS
The Gillet farmhouse, built in 1878, sits proud on the hill above West St, one of the prettiest roads in New Lebanon. They grew Gladiolus from 1935-1953, selling the bulbs world wide. A scrapbook with the history conveys with the house. Facing east, the house is surrounded by mature landscaping, pond, garden, and woods rising behind the house. The 2328 sq ft house has 3 beds/2 baths, + den on the 1st fl that could be a 1st fl bedroom. You'll find original trim, doors, wavy glass, interior shutters, wood floors throughout & antique Acorn stove in the kitchen. Large double parlor living room has a fireplace with wood stove insert. Sunroom and open kitchen have vaulted ceilings, skylights and lots of light. Rear patio, 2 car garage, 2 sheds. 14min to Jiminy Peak, 20min-Chatham, 36min-Albany

187 West Street, New Lebanon

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