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$500,000
5 Beds 2 Baths 202621961 MLS
Extensively renovated in 2024, this exceptional year-round Queechy Lake retreat offers a rare combination of lifestyle, privacy, and income potential with a very active summer and winter activities in the lake or on the ice! Spanning three finished levels, the property features a total of 5 bedrooms and 2 full bathrooms. Thoughtful renovations throughout deliver a truly move-in-ready home with modern updates, quality finishes, and brand-new furnishings included. Designed for flexibility, the home offers versatile multi-unit living with two kitchens and separate owner or guest access—ideal for rental income, multi-generational living, or use as a single five-bedroom residence. The first-floor unit includes two bedrooms, one full bath, and a fireplace, while the second and third floors comprise a spacious three-bedroom, one-bath unit. Enjoy deeded private beach and boat launch access for easy lake living, all in a high-demand, year-round location just minutes from Jiminy Peak. Ideally situated less than 15 minutes from Chatham and a short drive to Hudson, offering dining, shopping, Warren Street attractions, and Amtrak access to New York City.Approximately a 30-minute drive to Pittsfield, Lenox, Stockbridge, Tanglewood, and the Norman Rockwell Museum, with much more to explore in the area. Virtual tour available. An outstanding opportunity for full-time living, weekend retreats, or investment use.

105 McNamee Road

$937,000
6 Beds 6 Baths 202621701 MLS
Spacious 3-Story Berkshire Mountain Retreat Sleeps 16 Fully Furnished Family Home/Turnkey Airbnb Investment. Panoramic views and exceptional space for large families, group getaways, or a turnkey short-term rental investment. Move-in ready. The light-filled main living area features a dramatic wall of windows showcasing the mountain views, a soaring stone fireplace, an open-concept floor plan perfect for entertaining. The kitchen is equipped with granite countertops, custom cherry cabinetry, newer appliances, & a large dining area where everyone can gather. The first-floor primary suite offers comfort and privacy with an oversized bathroom featuring a soaking tub, walk-in shower, bidet, and walk-in closets. An additional first-floor bedroom/office includes a closet, full bath, and sleeper couch. Upstairs you'll find two generous bedrooms with a shared bath, along with an open balcony overlooking the living and dining area below. The finished lower level boasts impressive 12-foot ceilings, two additional bedrooms, two full bathrooms, a large family room, and a recreation area-ideal for guests or extended family. Step outside onto the expansive trex deck and enjoy stunning Berkshire sunsets, entertain around the outdoor fire pit, or take advantage of the large cleared backyard with plenty of room for a future tennis court or in-ground pool. This home is being sold fully furnished and includes numerous extras: Backup generator Two game rooms with handcrafted checkers table, and backgammon, for the adults. And a second room for the kids with basketball shooting and a foosball table among other games. All with a private bathroom. Garage with extra refrigerator, mini refrigerator, air comp portable power tools, radial arm saw, and more. 220-volt outlet for convenient EV. Located just minutes from Queechy Lake, with lake access, excellent restaurants, Tanglewood, Lenox, Stockbridge, Chatham, Williamstown, Hudson & TSP, I90

35 Whitetail Trace

$799,000
3 Beds 1 Baths 202620821 MLS
Discover the perfect blend of privacy, space, and versatility with this custom-built 2,400 sq. ft. home nestled on 5.5 scenic acres. Featuring 3 bedrooms, 1 bath, and soaring cathedral ceilings, this one-of-a-kind property offers comfortable living with exceptional indoor and outdoor amenities. Step outside to your own private retreat, complete with an inground pool, pool house, greenhouse with a newer metal roof, basketball court, and beautifully landscaped grounds. Enjoy the beauty of mature plum, apple, pear, and mimosa trees, stunning Japanese maples, and a charming grape arbor that creates a peaceful setting for relaxing or entertaining. Ideal for car enthusiasts, hobbyists, or small business owners, the property includes an attached 4-car garage plus a separate insulated building with electric that accommodates up to three additional vehicles. The upper level offers a dedicated home office and a second finished room perfect for a gym, art studio, guest space, hobby room, or private retreat. Whether you're dreaming of a hobby farm, home-based business, workshop, studio, or simply a peaceful country escape with room to grow, this exceptional property offers endless possibilities. The combination of acreage, multiple outbuildings, abundant storage, recreation, and mature landscaping makes this a rare opportunity. Conveniently located while offering the privacy and tranquility of country living, this is more than a home--it's a lifestyle. Schedule your private showing today and experience everything this remarkable property has to offer. Virtual tour https://walkthruphoto.info/Public/25-Hawthorne-Hill-Rd-6-29-26/25-Hawthorne-Hill-Rd-6-29-26.mp4 3D tour https://youriguide.com/25-Hawthorne-Hill-Rd-6-29-26/

25 Hawthorne Hill Road

$1,599,000
6 Beds 5 Baths 202617663 MLS
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 provide plenty of room for tractor, hobbies, and storage. This one-of-a-kind Chatham retreat combines elegant country living with modern convenience, all just a short drive to the charming villages, restaurants, and culture the Hudson Valley is known for.

20 Stony Knoll

$575,000
2 Beds 1 Baths 202617493 MLS
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 tranquility and discovery. Moments away lies the historic heart of Old Chatham, including the beloved Jackson's Old Chatham House, a landmark tavern cherished for generations. Surrounded by Columbia County's celebrated equestrian estates, historic farms, and scenic country roads, the property also enjoys convenient access to the cultural, culinary, and boutique destinations of Chatham, Hudson, and Ghent. As an extra perk, the bee hive colony with electric fencing (further away from the home), furnishings, kayaks, and more are available if the buyer desires.

896 County Route 13

$825,000
4 Beds 3 Baths 202614998 MLS
This home is perfect for entertaining, with multiple indoor and outdoor spaces. The custom-designed kitchen, complete with an ice maker, two separate ovens, and a gas stove, is ideal for hosting large holiday gatherings. The open living room and kitchen layout make it easy for conversation to flow. Upstairs, you'll find three oversized bedrooms, including a master suite with a newly remodeled bath featuring a jetted tub, walk-in tiled shower, and a customized walk-in closet. The secondary upstairs bath has also been updated. The basement offers a cozy finished area, and with its high ceilings, there's great potential to expand the space further. Outside, the bluestone patio with a fire pit and the expansive yard offer endless possibilities. The long driveway provides the privacy and seclusion you desire yet just 30 minutes to the Wassaic train station or Hudson Amtrak. Extras include a whole house generator and covered front porch perfect for morning coffee. Photos have been virtually staged.

521 Hall Hill Road

$275,000
202613680 MLS
31.5± Acres on Old Gale Hill Road, New Lebanon, NY Discover the perfect blend of peace, privacy, and possibility on this 31.5± acre wooded parcel in the heart of Columbia County. Tucked away on a quiet country road, this exceptional property offers a serene setting ideal for building your dream home, enjoying weekend getaways, or exploring recreational and hunting opportunities. A portion of the land may offer distant views of surrounding mountains and open fields, adding to the property's charm and potential. Located just minutes from the Hand Hollow Conservation Area outdoor enthusiasts will find endless options to connect with nature. All of this, yet conveniently located near the cultural and recreational amenities of the Berkshires,

L30.4 Gale Hill Road

$599,000
202611347 MLS
Rare opportunity to acquire 144+ acres of exceptional countryside spanning the Columbia-Rensselaer County border within the Townships of Stuyvesant and Schodack Landing. Offered as a combined purchase of the Ridge Road (93+ acres) and River Road (50+ acres) listings, this expansive property features extensive road frontage, mountain views, open farmland, wooded privacy, and a scenic meandering stream—creating a truly versatile land offering. The Ridge Road parcels include approximately 93+ acres across four parcels, with about 62 acres of actively cultivated hay fields benefiting from an agricultural tax exemption, along with wooded areas and a stream ideal for recreation and wildlife. The River Road parcels comprise approximately 50+ acres across two parcels, highlighted by a 2.2-acre building lot with 816 feet of road frontage and access to municipal sewer, plus an 80-foot private right-of-way over the rail tracks leading to the remaining acreage. Approximately 20 acres are currently farmed for hay, with a mix of open and wooded land beyond. Whether envisioned as a private estate, multi-home development, working farm, equestrian or livestock property, recreational or hunting retreat, or long-term investment, this combined offering provides rare scale, flexibility, and infrastructure in a peaceful rural setting. Ideally located just 15 minutes to downtown Albany, 40 minutes to Hudson, and approximately 2.5 hours from NYC, this is a unique opportunity to secure a large contiguous acreage with both privacy and accessibility.

L29A Ridge Road

$840,000
4 Beds 3 Baths 202610083 MLS
Discover your own private sanctuary nestled in the woods, with a breathtaking Queechy Lake view from every level of the home. Fully furnished, move in ready. Relax or entertain on expansive multi-level decks that overlook the water, perfect for a weekend retreat or full-time lakeview living. The open floor plan and walls of windows flood the main living area with natural light and stunning views in every season. The home offers three comfortable bedrooms and a full bath on the lower level, plus a private main bedroom en-suite on the top floor, along with an additional office or reading room ideal for work or quiet relaxation. An outdoor shower on the deck adds a special touch, allowing you to rinse off while taking in the lake scenery. A one-car garage with an attached workout or yoga room provides even more flexible space for hobbies and wellness. This custom-built 1980s home sits in a wooded compound that includes access to a tennis court and is just a short drive to premier Berkshire skiing and the rich cultural attractions of the region, including theaters, music, and museums

308 Shaker Ridge Drive

$719,000
5 Beds 4 Baths 202518112 MLS
Welcome to your private retreat in the Taconic Hills School District! Set on 8 serene acres, this beautifully renovated home offers the perfect balance of comfort, style, and versatility. With 5 bedrooms and 4 full baths, there's plenty of space for family, friends, or guests. The sun-drenched great room is the heart of the home, featuring vaulted ceilings and dual stone fireplaces that create a warm, inviting atmosphere. The updated kitchen is both functional and stylish, complete with new cabinetry, butcher block countertops, and a spacious walk-in pantry. The finished lower level offers 2 additional bedrooms, a full bath, a family room, and a walkout, making it an ideal setup for guests, in-laws, or even rental potential. An oversized 2-car garage provides ample storage, while the open, peaceful grounds invite you to enjoy nature and outdoor living. Perfectly located—just 20 minutes to Catamount Ski Resort, Hudson, and Lake Taghkanic, and only an hour to Hunter and Windham—this property is ideal as a primary residence, weekend escape, or a high-potential short-term rental. Don't miss the chance to make this versatile and beautifully updated property yours!

100 Schnackenberg Road

$179,000
202513766 MLS
WHAT A FIND - OK GO! Build your Hudson Valley dream home in Kinderhook on this private 8 acre wooded parcel with a pond view (some deer too!). Location just off 9H; less than 10 minutes from the Historic Village area of Kinderhook (historic properties, restaurants, theatres, art galleries, orchards, farms, etc.), 10 minutes to Columbia County Airport, 20 minutes to Hudson/Amtrak to NYC, 30 minutes to Albany/Airport; Ichabod Crane School District. Many large mature oak, pockets of pine, also hemlock trees (some oak may hold value for selling/lumbering). USDA mortgage eligible location, zoned 02 for single family, most of pond is off property. Please do not trespass, scheduled appts only. Walk the property showing where you are in real time using a free app/parcel file provided. Flagging/Maps are approximate. SE corner monument that is a stone pile with Rebar was flagged along with a stake . A stake w/flagging was placed at the approximate SW and NW corners. Old low stone wall remnants were found along the south and east property boundaries. The west boundary shares the ROW with Fischer Road. LA has flagged along Fischer Rd to show approx. west side boundaries. See documents for details. Best place to park is beyond 505 Fischer Rd on right off Rd. Easiest to walk in near the FOR SALE sign. PROPERTY ON LEFT between 562 and 505 Fischer Rd Homes. Electric at road. Property has been in family for years. No perc or well tests have been done. Homes in the area have well and septic systems. Highest point of property is at the tip of the triangle. The mid-lower end of the triangle affords many opportunities for home placement and driveway options. DON'T MISS WEBSITE!

L25 Fischer Road

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