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Seven vehicle spaces, over five acres, and your own private retreat: Car enthusiasts, hobbyists, and anyone craving room to spread out, this unique property deserves a closer look! Set on approximately 5.3 picturesque acres, this one-of-a-kind property offers a rare combination of garage space, flexible living areas, and outdoor amenities that make everyday living feel like a getaway! The standout feature? Exceptional vehicle capacity, including an attached garage and a substantial detached, insulated garage with electricity, ideal for those who need space for vehicles, equipment, projects, or hobbies! And there's so much more... Enjoy summer days by the inground pool, entertain poolside, or simply unwind surrounded by beautiful, mature landscaping. The grounds feature a greenhouse, fruit trees, grape arbor, pool house, and basketball court, offering plenty of room to enjoy the outdoors. Inside, cathedral ceilings and flexible living spaces offer room to work, create, relax, and make the property your own. Whether you're searching for a country escape, a property that accommodates your automotive passions, or a place where you can spread out and enjoy a little more freedom, the possibilities here are worth exploring! If you've been searching for garage space that's hard to find, room for your hobbies, and a property that offers more than the ordinary, this could be the one- Come see the possibilities for yourself!

3 Beds ⋅ 1 Baths ⋅ 202628649 MLS

Seven vehicle spaces, over five acres, and your own private retreat: Car enthusiasts, hobbyists, and anyone craving room to spread out, this unique property deserves a closer look! Set on approximately 5.3 picturesque acres, this one-of-a-kind property offers a rare combination of garage space, flexible living areas, and outdoor amenities that make everyday living feel like a getaway! The standout feature? Exceptional vehicle capacity, including an attached garage and a substantial detached, insulated garage with electricity, ideal for those who need space for vehicles, equipment, projects, or hobbies! And there's so much more... Enjoy summer days by the inground pool, entertain poolside, or simply unwind surrounded by beautiful, mature landscaping. The grounds feature a greenhouse, fruit trees, grape arbor, pool house, and basketball court, offering plenty of room to enjoy the outdoors. Inside, cathedral ceilings and flexible living spaces offer room to work, create, relax, and make the property your own. Whether you're searching for a country escape, a property that accommodates your automotive passions, or a place where you can spread out and enjoy a little more freedom, the possibilities here are worth exploring! If you've been searching for garage space that's hard to find, room for your hobbies, and a property that offers more than the ordinary, this could be the one- Come see the possibilities for yourself!

25 Hawthorne Hill Road, New Lebanon

$735,000

Welcome to Wilbor Farmhouse, a circa 1875 Victorian on 1.4 acres in the historic hamlet of Old Chatham. A wraparound covered porch, decorative wood brackets, and custom shutters give the house its period charm, and original wide-plank pine floors carry that history inside. Fully restored from top to bottom, it offers three bedrooms, 2.5 baths, and a large yard. A wood stove warms the sitting room, and the all-new kitchen, with energy-efficient appliances and custom solid wood cabinetry, opens to a deck for summer dinners. Once a bed and breakfast, the house is a short walk from the Old Chatham Country Store, ten minutes from Chatham's thriving arts scene, and thirty minutes from vibrant Hudson, with Amtrak service to New York City.

3 Beds ⋅ 3 Baths ⋅ 202628565 MLS

Welcome to Wilbor Farmhouse, a circa 1875 Victorian on 1.4 acres in the historic hamlet of Old Chatham. A wraparound covered porch, decorative wood brackets, and custom shutters give the house its period charm, and original wide-plank pine floors carry that history inside. Fully restored from top to bottom, it offers three bedrooms, 2.5 baths, and a large yard. A wood stove warms the sitting room, and the all-new kitchen, with energy-efficient appliances and custom solid wood cabinetry, opens to a deck for summer dinners. Once a bed and breakfast, the house is a short walk from the Old Chatham Country Store, ten minutes from Chatham's thriving arts scene, and thirty minutes from vibrant Hudson, with Amtrak service to New York City.

23 Frog Alley, Chatham

$339,800

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.

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

$495,000

Welcome to the Taconic Wayside Inn, a roadside tavern and boarding house dating to 1856, set on 1.2 acres in Copake Falls at the edge of Taconic State Park. The 5,512-square-foot main building holds a commercial kitchen, a tavern with a wraparound bar, 3 dining rooms, 5 guest rooms, and 3 apartments, with a large pole barn and additional outbuildings. Babe Ruth was a regular here, and for more than fifty years, under one family's care, the inn played host to weddings, reunions, and local bands. Commercial, agricultural, and residential zoning supports a restaurant, boutique inn, mixed-use investment, or private residence. The Taconic Wayside Inn stands ready to become the gathering place of Copake Falls once again, and a destination for the whole region.

6 Baths ⋅ 202628204 MLS

Welcome to the Taconic Wayside Inn, a roadside tavern and boarding house dating to 1856, set on 1.2 acres in Copake Falls at the edge of Taconic State Park. The 5,512-square-foot main building holds a commercial kitchen, a tavern with a wraparound bar, 3 dining rooms, 5 guest rooms, and 3 apartments, with a large pole barn and additional outbuildings. Babe Ruth was a regular here, and for more than fifty years, under one family's care, the inn played host to weddings, reunions, and local bands. Commercial, agricultural, and residential zoning supports a restaurant, boutique inn, mixed-use investment, or private residence. The Taconic Wayside Inn stands ready to become the gathering place of Copake Falls once again, and a destination for the whole region.

108 NY-344, Copake

$445,000

Welcome to 88 County Route 26A, a timeless Stuyvesant retreat where classic charm meets comfortable country living. This beautifully maintained home is in mint condition and truly move in ready, offering a peaceful sense of space and privacy while remaining conveniently connected to the surrounding area. Ideally located just 10 minutes from Kinderhook Shopping Center and within easy reach of Schodack Island State Park, you can enjoy the best of both convenience and nature. Featuring new appliances and three additional bonus rooms, this home offers endless possibilities to create spaces tailored to your lifestyle. Whether you envision a home office, studio, gym, guest space, hobby room, or something entirely your own, these versatile rooms give you the freedom to make the home uniquely yours. With its timeless appeal, flexible layout, and tranquil setting, 88 County Route 26A is a rare opportunity to enjoy comfortable country living in a home that is ready for you to move in and make your own.

3 Beds ⋅ 3 Baths ⋅ 202627553 MLS

Welcome to 88 County Route 26A, a timeless Stuyvesant retreat where classic charm meets comfortable country living. This beautifully maintained home is in mint condition and truly move in ready, offering a peaceful sense of space and privacy while remaining conveniently connected to the surrounding area. Ideally located just 10 minutes from Kinderhook Shopping Center and within easy reach of Schodack Island State Park, you can enjoy the best of both convenience and nature. Featuring new appliances and three additional bonus rooms, this home offers endless possibilities to create spaces tailored to your lifestyle. Whether you envision a home office, studio, gym, guest space, hobby room, or something entirely your own, these versatile rooms give you the freedom to make the home uniquely yours. With its timeless appeal, flexible layout, and tranquil setting, 88 County Route 26A is a rare opportunity to enjoy comfortable country living in a home that is ready for you to move in and make your own.

88 County Route 26A, Stuyvesant

$259,500

Opportunity awaits as this super cozy year-round unique 3bedroom 1.5 bath traditional retreat with an awesome huge deck which overlooks the High Falls State Conservation Area and Ogowamuck creak hits the market! This home features a large cozy family with hardwood floors, large eat in kitchen, huge 3 season sun porch, living room with custom bar, laundry room, den! Centrally located to everything including the Conservation area features hiking trails, trout fishing and Waterfall! A must see!

3 Beds ⋅ 2 Baths ⋅ 202627397 MLS

Opportunity awaits as this super cozy year-round unique 3bedroom 1.5 bath traditional retreat with an awesome huge deck which overlooks the High Falls State Conservation Area and Ogowamuck creak hits the market! This home features a large cozy family with hardwood floors, large eat in kitchen, huge 3 season sun porch, living room with custom bar, laundry room, den! Centrally located to everything including the Conservation area features hiking trails, trout fishing and Waterfall! A must see!

57 Main Street, Philmont

$409,900

Enjoy living on a quiet side road in Kinderhook Village. Lived in by the current owners for fifty years. There is a four season sun room across the back of the house which leads to a deck and fenced in yard. Many extras come with this house , whole house generator, four split systems for cooling and hardwood floors under the carpets. The lower floor in the house has a nice size den and a home office . The laundry room shares space with a half bath. Hop on the rail trail and explore the great outdoors.

3 Beds ⋅ 2 Baths ⋅ 202626028 MLS

Enjoy living on a quiet side road in Kinderhook Village. Lived in by the current owners for fifty years. There is a four season sun room across the back of the house which leads to a deck and fenced in yard. Many extras come with this house , whole house generator, four split systems for cooling and hardwood floors under the carpets. The lower floor in the house has a nice size den and a home office . The laundry room shares space with a half bath. Hop on the rail trail and explore the great outdoors.

4 Orchard Drive, Kinderhook

$1,300,000

Welcome to Bons Reves House, a beautifully designed escape on nearly seven acres in the Austerlitz hills. Built in 1985 and meticulously renovated and expanded in 2012 and 2025, this 4-bedroom, 3.5-bath contemporary feels like a luxury treehouse hidden among mature hardwoods. Custom millwork, natural stone and wood surfaces, bespoke plaster treatments, and a true country kitchen give the gracious, flowing layout real character. A four-season sunroom, wraparound Trex deck, and professionally landscaped grounds extend living outdoors. Just 15 minutes from Chatham, 20 to Great Barrington, MA, and 35 minutes to Hudson, this is a home built as much for weekend entertaining as it is for quiet days spent resting and recharging.

4 Beds ⋅ 4 Baths ⋅ 202625723 MLS

Welcome to Bons Reves House, a beautifully designed escape on nearly seven acres in the Austerlitz hills. Built in 1985 and meticulously renovated and expanded in 2012 and 2025, this 4-bedroom, 3.5-bath contemporary feels like a luxury treehouse hidden among mature hardwoods. Custom millwork, natural stone and wood surfaces, bespoke plaster treatments, and a true country kitchen give the gracious, flowing layout real character. A four-season sunroom, wraparound Trex deck, and professionally landscaped grounds extend living outdoors. Just 15 minutes from Chatham, 20 to Great Barrington, MA, and 35 minutes to Hudson, this is a home built as much for weekend entertaining as it is for quiet days spent resting and recharging.

351 Dugway Road, Austerlitz

$499,000

Move-In Ready Colonial style home on 1.6 private acres in one of Valatie's most desirable neighborhoods! This is a must see property with plenty of space. 1889 sq. feet plus a full basement. Two car attached garage with additional overhead storage. The spacious eat in kitchen opens up to a step down family room with gas stove and sliding glass doors that open to the deck & overlook the private back yard. There is a large living & formal dining room that can be used for extra space to entertain or possible office. Outside there is plenty of room for gatherings, gardening, or just enjoy the peace and quiet while sitting on your deck. The spacious two story outbuilding with electrical gives you multiple options: Workshop, studio, home business or just an abundance of extra storage for outdoor equipment or recreational toys. You will love the location of this tree lined cul-de-sac neighborhood. Explore the vast history & activities surrounding this area. Access to the Albany-Hudson Electric Trail is right around the corner. Super convenient location for traveling to the Capital Region, NYC or Massachusetts. Pride in ownership shines through. If you need a home that is spotless, private and move-in condition, here it is....You're Welcome! Some room photos are virtually staged.

3 Beds ⋅ 2 Baths ⋅ 202625134 MLS

Move-In Ready Colonial style home on 1.6 private acres in one of Valatie's most desirable neighborhoods! This is a must see property with plenty of space. 1889 sq. feet plus a full basement. Two car attached garage with additional overhead storage. The spacious eat in kitchen opens up to a step down family room with gas stove and sliding glass doors that open to the deck & overlook the private back yard. There is a large living & formal dining room that can be used for extra space to entertain or possible office. Outside there is plenty of room for gatherings, gardening, or just enjoy the peace and quiet while sitting on your deck. The spacious two story outbuilding with electrical gives you multiple options: Workshop, studio, home business or just an abundance of extra storage for outdoor equipment or recreational toys. You will love the location of this tree lined cul-de-sac neighborhood. Explore the vast history & activities surrounding this area. Access to the Albany-Hudson Electric Trail is right around the corner. Super convenient location for traveling to the Capital Region, NYC or Massachusetts. Pride in ownership shines through. If you need a home that is spotless, private and move-in condition, here it is....You're Welcome! Some room photos are virtually staged.

40 Knollwood Drive, Valatie

$735,000

Welcome to Carlin Cottage, a turn-of-the-century residence in the heart of Historic Hudson, pairing original charm with designer updates. This three-bedroom, two-bath home offers all-new systems, premium finishes, a private, fenced backyard, and off-street parking, with the option to purchase fully furnished. Custom soapstone countertops, a striking AGA range, and Moroccan Zellige tilework reflect the high-end materials throughout, all restored by renowned designer Christina Salway. Set on a quiet one-way street, Carlin Cottage puts Warren Street's galleries, restaurants, and shops just a short walk away. Grab coffee or a cocktail at The Maker, catch a show at Basilica Hudson, or take in river views from Promenade Hill Park. Carlin Cottage offers a sweet opportunity to put down roots in vibrant Hudson.

3 Beds ⋅ 2 Baths ⋅ 202624817 MLS

Welcome to Carlin Cottage, a turn-of-the-century residence in the heart of Historic Hudson, pairing original charm with designer updates. This three-bedroom, two-bath home offers all-new systems, premium finishes, a private, fenced backyard, and off-street parking, with the option to purchase fully furnished. Custom soapstone countertops, a striking AGA range, and Moroccan Zellige tilework reflect the high-end materials throughout, all restored by renowned designer Christina Salway. Set on a quiet one-way street, Carlin Cottage puts Warren Street's galleries, restaurants, and shops just a short walk away. Grab coffee or a cocktail at The Maker, catch a show at Basilica Hudson, or take in river views from Promenade Hill Park. Carlin Cottage offers a sweet opportunity to put down roots in vibrant Hudson.

225 Robinson Street, Hudson

$699,000

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!

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

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.

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

$529,988

NOW PRICED TO SELL! REBUILT IN 2026. TWO BEDROOM SUITES. WALK TO HUDSON. Your full-time home, Hudson Valley weekend escape, or potential vacation rental—with the work already done! Located in Greenport with a Hudson mailing address, minutes from Warren Street's shops, restaurants, galleries, and Amtrak. • TWO BEDROOM SUITES—First-floor suite with a walk-in closet and private bath with walk-in shower. Upstairs suite features white shiplap walls and ceilings, custom closet shelving, and a stylish full bath. • BEAUTIFUL KITCHEN & OPEN LIVING—White shaker cabinetry, granite countertops, stainless steel appliances, red oak hardwood floors, recessed lighting, and inviting spaces to gather. • EXTENSIVE 2026 UPDATES—New roof, Pella windows and doors, plumbing, electrical, flooring, fixtures, and appliances. Energy-efficient heat pumps provide heating and air conditioning. • ROOM TO EXPAND—Unfinished basement offers potential for additional finished space, subject to permits and approvals. • INVITING OUTDOOR SPACE—Rear deck with modern pergola overlooks the landscaped backyard. Add a fire pit and barbecue for outdoor entertaining. Newly planted trees will provide greater screening and privacy as they mature. • QUALITY FINISHES—Custom trim, Hardie® shingle siding, welcoming front porch, and newly paved driveway. • VACATION RENTAL POTENTIAL—Two private suites, updated systems, and proximity to Hudson offer appeal for a potential Airbnb or weekend rental. Buyers must verify Town of Greenport short-term rental regulations, permits, and property eligibility. Rental approval and income are not guaranteed. Move right in and start enjoying the Hudson Valley!

2 Beds ⋅ 2 Baths ⋅ 202622433 MLS

NOW PRICED TO SELL! REBUILT IN 2026. TWO BEDROOM SUITES. WALK TO HUDSON. Your full-time home, Hudson Valley weekend escape, or potential vacation rental—with the work already done! Located in Greenport with a Hudson mailing address, minutes from Warren Street's shops, restaurants, galleries, and Amtrak. • TWO BEDROOM SUITES—First-floor suite with a walk-in closet and private bath with walk-in shower. Upstairs suite features white shiplap walls and ceilings, custom closet shelving, and a stylish full bath. • BEAUTIFUL KITCHEN & OPEN LIVING—White shaker cabinetry, granite countertops, stainless steel appliances, red oak hardwood floors, recessed lighting, and inviting spaces to gather. • EXTENSIVE 2026 UPDATES—New roof, Pella windows and doors, plumbing, electrical, flooring, fixtures, and appliances. Energy-efficient heat pumps provide heating and air conditioning. • ROOM TO EXPAND—Unfinished basement offers potential for additional finished space, subject to permits and approvals. • INVITING OUTDOOR SPACE—Rear deck with modern pergola overlooks the landscaped backyard. Add a fire pit and barbecue for outdoor entertaining. Newly planted trees will provide greater screening and privacy as they mature. • QUALITY FINISHES—Custom trim, Hardie® shingle siding, welcoming front porch, and newly paved driveway. • VACATION RENTAL POTENTIAL—Two private suites, updated systems, and proximity to Hudson offer appeal for a potential Airbnb or weekend rental. Buyers must verify Town of Greenport short-term rental regulations, permits, and property eligibility. Rental approval and income are not guaranteed. Move right in and start enjoying the Hudson Valley!

3 Milo Street, Greenport

$659,000

Open House Saturday 9/10 11-1:00 pm. New Lower Price! BONNIE LEA ESTATES! Welcome to an unrivaled 3,000+ sq ft Colonial masterpiece set on 1.27 acres with jaw-dropping pastoral views in the highly desired Ichabod Crane S.D. Immaculately maintained and artfully upgraded, this 5+ Bedroom and 2.5 bathroom residence blends custom craftsmanship and a breathtaking outdoor sanctuary in one of the locals' favorite walkable neighborhoods! Step inside to pristine hardwood floors throughout, central AC, livingroom, office space and a showstopping family room featuring radiant-heated custom slate floors, a wood burning fireplace w/newer exhaust liner, storage closets & a 1st flr washer & dryer ~ a massive, expanded addition tailored for your cozy family gatherings. A perfect space for your holiday dining table seating 24+ guests! The remodeled eat-in kitchen showcases custom wood cabinetry, solid granite counters & stainless steel appliances. Upstairs a large primary bedroom & bathroom share in the spectacular views. A refinshed bonus room boasts efficient mini-splits, LVP flooring & gorgeous wood accent walls--and includes abundant eaves storage. A dry basement adds more incredible storage plus a 2nd washer & dryer & utility sink. There's more...relax with your morning coffee or evening wine with the gorgeous views in the glass-enclosed 3-season sunroom or step outside to several bluestone patios and a full-length covered front porch. The botanical paradise boasts a wildlife-proof vegetable garden (galvanized steel fence dug 12'' deep), rich perennial gardens w/hibiscus, rhododendrons, forsythia, daffodils, black-eyed Susans, flowering peach, peonies, lilacs, & irises and surrounded by black walnut, oak, spruce, apple & mulberry trees. Complete w/a 10-yr young roof, 2-car garage, oversized paved driveway, 2 newer sheds (20x12 & 4x8), and tiled bathrooms. A rare, high-end home in a top-notch community that any family would definitely love and enjoy for years to come.

5 Beds ⋅ 3 Baths ⋅ 202622277 MLS

Open House Saturday 9/10 11-1:00 pm. New Lower Price! BONNIE LEA ESTATES! Welcome to an unrivaled 3,000+ sq ft Colonial masterpiece set on 1.27 acres with jaw-dropping pastoral views in the highly desired Ichabod Crane S.D. Immaculately maintained and artfully upgraded, this 5+ Bedroom and 2.5 bathroom residence blends custom craftsmanship and a breathtaking outdoor sanctuary in one of the locals' favorite walkable neighborhoods! Step inside to pristine hardwood floors throughout, central AC, livingroom, office space and a showstopping family room featuring radiant-heated custom slate floors, a wood burning fireplace w/newer exhaust liner, storage closets & a 1st flr washer & dryer ~ a massive, expanded addition tailored for your cozy family gatherings. A perfect space for your holiday dining table seating 24+ guests! The remodeled eat-in kitchen showcases custom wood cabinetry, solid granite counters & stainless steel appliances. Upstairs a large primary bedroom & bathroom share in the spectacular views. A refinshed bonus room boasts efficient mini-splits, LVP flooring & gorgeous wood accent walls--and includes abundant eaves storage. A dry basement adds more incredible storage plus a 2nd washer & dryer & utility sink. There's more...relax with your morning coffee or evening wine with the gorgeous views in the glass-enclosed 3-season sunroom or step outside to several bluestone patios and a full-length covered front porch. The botanical paradise boasts a wildlife-proof vegetable garden (galvanized steel fence dug 12'' deep), rich perennial gardens w/hibiscus, rhododendrons, forsythia, daffodils, black-eyed Susans, flowering peach, peonies, lilacs, & irises and surrounded by black walnut, oak, spruce, apple & mulberry trees. Complete w/a 10-yr young roof, 2-car garage, oversized paved driveway, 2 newer sheds (20x12 & 4x8), and tiled bathrooms. A rare, high-end home in a top-notch community that any family would definitely love and enjoy for years to come.

74 Hawthorne Drive, Valatie

$469,000

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.

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

$295,000

Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and three bedrooms and a full bath above. The unfinished walk-out basement adds approximately 360 square feet of flexible additional space, and is ready to be finished to your own specifications. Ideal as a home office, guest quarters, home gym, or creative studio. A brand new heating system completes a renovation that leaves little to do but move in. Philmont is a small Columbia County village with a growing creative community and a genuine historic fabric. Hawthorne Valley School and its beloved farm store are nearby, as is the High Falls Conservation Area, where trails wind through hemlock ravines to Columbia County's highest waterfall. Local 111 and other village favorites are close at hand for dining. Hudson's Warren Street galleries, restaurants, and Amtrak station are eighteen minutes away, Chatham is fifteen minutes, and New York City is two and a half hours by car. The farm stands, hiking trails, and country roads that define life in this part of the valley are all within easy reach.

3 Beds ⋅ 2 Baths ⋅ 202616964 MLS

Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and three bedrooms and a full bath above. The unfinished walk-out basement adds approximately 360 square feet of flexible additional space, and is ready to be finished to your own specifications. Ideal as a home office, guest quarters, home gym, or creative studio. A brand new heating system completes a renovation that leaves little to do but move in. Philmont is a small Columbia County village with a growing creative community and a genuine historic fabric. Hawthorne Valley School and its beloved farm store are nearby, as is the High Falls Conservation Area, where trails wind through hemlock ravines to Columbia County's highest waterfall. Local 111 and other village favorites are close at hand for dining. Hudson's Warren Street galleries, restaurants, and Amtrak station are eighteen minutes away, Chatham is fifteen minutes, and New York City is two and a half hours by car. The farm stands, hiking trails, and country roads that define life in this part of the valley are all within easy reach.

152 Main Street, Philmont

$2,150,000

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep to keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

3 Beds ⋅ 3 Baths ⋅ 202616466 MLS

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the beautiful Catskills. Stepping through the front door of a wide covered front porch, you'll find an open plan kitchen, dining & living room - the heart of the home, made cozy in winter by an efficient wood stove. The first floor also includes a mud room, office, powder room, laundry room and den. However, it is the 600 sq ft ''Great Room'', with windows on 3 sides that immerse you in the ever-shifting displays of nature and the Catskill range. Upstairs you'll find 3 generous sized bedrooms and 2 full baths including a primary suite with walk-in closet room. The pond, designed by famed UK pool master Anthony Archer-Wills, provides an unparalleled natural swimming experience, set among a chorus of frogs and dragonfly's dancing across the water. A variety of colorful waterlilies and other pond plantings keep to keep the water fresh and inviting. Renovated throughout in 2024-2025, this solar powered home offers you privacy, comfort and jaw dropping sunsets. Conveniently located 10 minutes from Chatham, 30 minutes to the train in Hudson, 40 minutes to the Albany Airport and 25 minutes to Great Barrington & all the culture and fun that our neighboring Berkshires offer. Broker Owned.

53 May Lane, Austerlitz

$599,000

Move right in! Enjoy the best of both worlds at 22 Van Winkle Road -- a sophisticated retreat tucked away in the serene ''Silent Zone'' of Hudson's sought-after Academy Hill community. This spacious 4-bedroom plus den, 3 full bath townhome offers stunning Hudson River and mountain views, blending peaceful suburban privacy with convenient access to the vibrant energy of nearby Warren Street's acclaimed dining, breweries, art galleries, and boutiques.

4 Beds ⋅ 3 Baths ⋅ 202615994 MLS

Move right in! Enjoy the best of both worlds at 22 Van Winkle Road -- a sophisticated retreat tucked away in the serene ''Silent Zone'' of Hudson's sought-after Academy Hill community. This spacious 4-bedroom plus den, 3 full bath townhome offers stunning Hudson River and mountain views, blending peaceful suburban privacy with convenient access to the vibrant energy of nearby Warren Street's acclaimed dining, breweries, art galleries, and boutiques.

22 Van Winkle Road, Hudson

$10,995,000

DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep ''southern-style'' covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator.

4 Beds ⋅ 6 Baths ⋅ 202614668 MLS

DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep ''southern-style'' covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator.

199 Eichybush Road, Kinderhook

$1,650,000

Spectacularly renovated and offered for the first time since its complete transformation, this exceptional pondfront residence overlooks Maiden Lake in the highly sought-after Fern Hill community. Designed for refined living with privacy and effortless indoor-outdoor flow, the home is clad in warm natural cedar siding that blends seamlessly with the surrounding landscape. Maiden Lake is a shared pond maintained by the Fern Hill HOA with private swimming access. Set on a quiet country road just outside the Hawthorne Valley hamlet, the property is minutes to Great Barrington, close to respected private schools, and offers easy access to the Taconic Parkway and Albany International Airport. The thoughtfully designed interior features multiple private bedroom suites, lofted ceilings, and expansive light-filled living spaces. High-quality natural materials and craftsmanship are showcased throughout, including white oak flooring, cherry cabinetry, soapstone kitchen countertops, French oak stairs, and a custom single-stringer staircase with black steel detailing. Bedrooms feature maple flooring, while the loft or studio offers wide-board pine floors. The open main living area centers on a chef's kitchen with an oversized island and premium appliances by Bosch, Thermador, Fisher & Paykel, KitchenAid, and Zephyr. Bathrooms feature classic subway tile, marble countertops, and rain and hand-shower fixtures. Comfort and efficiency include Marvin triple-pane windows, automated skylights, radiant heated floors, heat pump heating and cooling, gas fireplace, whole-house generator, 400-amp service, updated systems, and ethernet throughout. A cherry-appointed laundry room and sun-filled mudroom add function and charm. The landscaped grounds include perennial gardens, bluestone walkways, raised beds, selective fencing, a charming barn with luxury sauna, wraparound Brazilian walnut deck, gazebo, additional pond-facing deck, and private dock. Nearby are Hudson cultural destinations.

3 Beds ⋅ 3 Baths ⋅ 202612013 MLS

Spectacularly renovated and offered for the first time since its complete transformation, this exceptional pondfront residence overlooks Maiden Lake in the highly sought-after Fern Hill community. Designed for refined living with privacy and effortless indoor-outdoor flow, the home is clad in warm natural cedar siding that blends seamlessly with the surrounding landscape. Maiden Lake is a shared pond maintained by the Fern Hill HOA with private swimming access. Set on a quiet country road just outside the Hawthorne Valley hamlet, the property is minutes to Great Barrington, close to respected private schools, and offers easy access to the Taconic Parkway and Albany International Airport. The thoughtfully designed interior features multiple private bedroom suites, lofted ceilings, and expansive light-filled living spaces. High-quality natural materials and craftsmanship are showcased throughout, including white oak flooring, cherry cabinetry, soapstone kitchen countertops, French oak stairs, and a custom single-stringer staircase with black steel detailing. Bedrooms feature maple flooring, while the loft or studio offers wide-board pine floors. The open main living area centers on a chef's kitchen with an oversized island and premium appliances by Bosch, Thermador, Fisher & Paykel, KitchenAid, and Zephyr. Bathrooms feature classic subway tile, marble countertops, and rain and hand-shower fixtures. Comfort and efficiency include Marvin triple-pane windows, automated skylights, radiant heated floors, heat pump heating and cooling, gas fireplace, whole-house generator, 400-amp service, updated systems, and ethernet throughout. A cherry-appointed laundry room and sun-filled mudroom add function and charm. The landscaped grounds include perennial gardens, bluestone walkways, raised beds, selective fencing, a charming barn with luxury sauna, wraparound Brazilian walnut deck, gazebo, additional pond-facing deck, and private dock. Nearby are Hudson cultural destinations.

119 Fern Hill Road, Ghent

$599,000

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.

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

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