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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.

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

$1,125,000

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.

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

$325,000

Welcome to Queechy Lake Cottage, a vintage Hudson Valley retreat in a private community in Northern Columbia County. Built in the 1930s and renovated in 2017/18, this charming three bedroom cottage offers indoor-outdoor living perfect for a family with a large deck, screened-in porch, fire pit, and rare beach lake access. The open living area has vaulted ceilings and the large, lovely screened porch with mahogany wood floors extends the living area. Outside is a spacious deck for bbqing, entertaining or unwinding after a day at the lake. As a member of the Queechy Shores Association, this three-season cottage includes access to a private beach just a five-minute walk away, plus pontoon boat docking and mooring rights. Less than 2.5 hours from New York City, homes in this community are often passed down through generations.

3 Beds ⋅ 1 Baths ⋅ 202611576 MLS

Welcome to Queechy Lake Cottage, a vintage Hudson Valley retreat in a private community in Northern Columbia County. Built in the 1930s and renovated in 2017/18, this charming three bedroom cottage offers indoor-outdoor living perfect for a family with a large deck, screened-in porch, fire pit, and rare beach lake access. The open living area has vaulted ceilings and the large, lovely screened porch with mahogany wood floors extends the living area. Outside is a spacious deck for bbqing, entertaining or unwinding after a day at the lake. As a member of the Queechy Shores Association, this three-season cottage includes access to a private beach just a five-minute walk away, plus pontoon boat docking and mooring rights. Less than 2.5 hours from New York City, homes in this community are often passed down through generations.

127 Queechy Shores, Canaan

$1,900,000

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.

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

$130,000

Opportunity awaits. This 3 bedroom, 1.1 bath Dutch Colonial home offers 1372sf of living space and is ready for it's next chapter. Home needs fair amount of renovation and will be cash only, sold ''as-is.'' Good sized living room with separate dining space, kitchen with good space , first floor bathroom is a full bath. Enclosed rear porch, and nice front porch. 2nd floor has 3 bedrooms, with primary containing 2 walk in closets. Half bath on 2nd floor could be expanded to full bath. Water shut off for winter. Garage is a tear down. Sweat equity could go a long way on this home. Septic in need of replacement

3 Beds ⋅ 2 Baths ⋅ 202615159 MLS

Opportunity awaits. This 3 bedroom, 1.1 bath Dutch Colonial home offers 1372sf of living space and is ready for it's next chapter. Home needs fair amount of renovation and will be cash only, sold ''as-is.'' Good sized living room with separate dining space, kitchen with good space , first floor bathroom is a full bath. Enclosed rear porch, and nice front porch. 2nd floor has 3 bedrooms, with primary containing 2 walk in closets. Half bath on 2nd floor could be expanded to full bath. Water shut off for winter. Garage is a tear down. Sweat equity could go a long way on this home. Septic in need of replacement

1169 State Route 295, Canaan

$675,000

Modern Country Home on Nearly 14 Acres A refined country haven offering privacy in an exceptional location between the Berkshires and Hudson--perfectly positioned for enjoyment of everything in between. This modern farmhouse blends volume, light, and quiet luxury. The cathedral-ceiling living room opens to a beautifully appointed kitchen and breakfast area, creating an effortless flow for daily living. The first-floor primary ensuite is a private sanctuary with a walk-in closet, double vanity, Jacuzzi soaking tub, separate shower, and enclosed water closet. Guest quarters are thoughtfully placed on the second floor, featuring a loft library, two generous bedrooms, a full bath, and an expansive studio or creative space. The finished walk-out lower level offers remarkable versatility for work, wellness, or recreation. Outdoors, the low-maintenance acreage unfolds with open land, wooded edges, and a meandering brook. Additional acreage available. Preview by appointment only. Exclusively offered at 695,000 dollars. Sunday showings are not preferred and, if necessary, limited to 10 am-12 pm Reproduction French train-station clock excluded from sale. 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.

3 Beds ⋅ 3 Baths ⋅ 202526629 MLS

Modern Country Home on Nearly 14 Acres A refined country haven offering privacy in an exceptional location between the Berkshires and Hudson--perfectly positioned for enjoyment of everything in between. This modern farmhouse blends volume, light, and quiet luxury. The cathedral-ceiling living room opens to a beautifully appointed kitchen and breakfast area, creating an effortless flow for daily living. The first-floor primary ensuite is a private sanctuary with a walk-in closet, double vanity, Jacuzzi soaking tub, separate shower, and enclosed water closet. Guest quarters are thoughtfully placed on the second floor, featuring a loft library, two generous bedrooms, a full bath, and an expansive studio or creative space. The finished walk-out lower level offers remarkable versatility for work, wellness, or recreation. Outdoors, the low-maintenance acreage unfolds with open land, wooded edges, and a meandering brook. Additional acreage available. Preview by appointment only. Exclusively offered at 695,000 dollars. Sunday showings are not preferred and, if necessary, limited to 10 am-12 pm Reproduction French train-station clock excluded from sale. 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.

3124-3100 County Route 9, Canaan

$710,000

This historic home was constructed by Thomas Bishop, a veteran of the War of 1812 in the early 1800's and was once known as Bishop's Tavern. It began as an inn and tavern on what was once, the Stockbridge and Hudson stagecoach line. Since then it has been lovingly tended and updated with an eye to preservation. Located on a quiet country road in Red Rock and surrounded by mature gardens and stately trees this property has much to offer. The front of the house has access to two covered porches, one on each floor that offer seating and views of the pasture and hill beyond. Entering the home from the side, this open porch entry brings you into a large parlor that stretches across the length of the main house. A newly built fireplace is flanked by floor to ceiling windows giving light to the original ceiling beams and wide board flooring. A full bath and pantry are set off this room. To the rear of the house is a combination kitchen and sitting room with access to the wrap around stone terrace through two sets of French doors. This room is a light and airy space with its generous windows and a propane stove for winter warmth. On the second floor there are three comfortable bedrooms; one with a working fireplace, one with a Juliette balcony and culminating in the main bedroom with a vaulted ceiling and a Palladian window overlooking the gardens and the two story barn/garage. The house and barn are set on one acre of land with a half acre parcel and a small pond across the road for view protection. More land available across the street of six acres Listing # 20254357. Queechy lake rights for swimming, boating and ice fishing just up the road. Come step into history and become part of the story of this unique property.

3 Beds ⋅ 2 Baths ⋅ 202525941 MLS

This historic home was constructed by Thomas Bishop, a veteran of the War of 1812 in the early 1800's and was once known as Bishop's Tavern. It began as an inn and tavern on what was once, the Stockbridge and Hudson stagecoach line. Since then it has been lovingly tended and updated with an eye to preservation. Located on a quiet country road in Red Rock and surrounded by mature gardens and stately trees this property has much to offer. The front of the house has access to two covered porches, one on each floor that offer seating and views of the pasture and hill beyond. Entering the home from the side, this open porch entry brings you into a large parlor that stretches across the length of the main house. A newly built fireplace is flanked by floor to ceiling windows giving light to the original ceiling beams and wide board flooring. A full bath and pantry are set off this room. To the rear of the house is a combination kitchen and sitting room with access to the wrap around stone terrace through two sets of French doors. This room is a light and airy space with its generous windows and a propane stove for winter warmth. On the second floor there are three comfortable bedrooms; one with a working fireplace, one with a Juliette balcony and culminating in the main bedroom with a vaulted ceiling and a Palladian window overlooking the gardens and the two story barn/garage. The house and barn are set on one acre of land with a half acre parcel and a small pond across the road for view protection. More land available across the street of six acres Listing # 20254357. Queechy lake rights for swimming, boating and ice fishing just up the road. Come step into history and become part of the story of this unique property.

605 County Route 24, Canaan

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