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$1,650,000

Set on 50 acres of complete privacy, this 1930's Colonial sits alone with sweeping views to the Berkshires. The home offers country living with a Livingroom with a fireplace, Diningroom with French doors opening to a porch. There is a heated sunroom to enjoy the quiet outside. The primary suite includes its own bathroom and a balcony perfect for morning coffee or stargazing. For added space, the third floor has been made into a yoga/workout room, along with an office and a bath. There are additional two bedrooms and 1 1/2 baths. Outside, sits a charming gazebo overlooking a tranquil pond perfect for nature watching. Also, there is a two car garage and an additional barn for a workshop or studio. Some updates are needed.

3 Beds ⋅ 4 Baths ⋅ 1049798 MLS

Set on 50 acres of complete privacy, this 1930's Colonial sits alone with sweeping views to the Berkshires. The home offers country living with a Livingroom with a fireplace, Diningroom with French doors opening to a porch. There is a heated sunroom to enjoy the quiet outside. The primary suite includes its own bathroom and a balcony perfect for morning coffee or stargazing. For added space, the third floor has been made into a yoga/workout room, along with an office and a bath. There are additional two bedrooms and 1 1/2 baths. Outside, sits a charming gazebo overlooking a tranquil pond perfect for nature watching. Also, there is a two car garage and an additional barn for a workshop or studio. Some updates are needed.

81 Tinker Hill Road, Pine Plains

$450,000

Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted ceiling that's well suited for year-round living. The flexible layout allows you to use the home as either a one- or two-bedroom, depending on your needs. Imagine enjoying dinner every evening with the lake as your backdrop or unwinding on the rear deck while taking in the beautiful water views. From morning coffee at sunrise to relaxing evenings by the water, this home offers a peaceful place to create lasting memories with loved ones and friends. You will enjoy the benefit a spacious basement and a detached one-car garage, providing plenty of storage for outdoor equipment, seasonal items, or hobbies. Situated on nearly half an acre with mature trees for an added buffer of privacy, there's ample room for outdoor activities, entertaining, gardening, or simply enjoying the open space. Whether you're looking for a full-time residence or a weekend retreat this oasis offers the comfort, charm, and lifestyle that make lakefront living so special. It all awaits you! Make it yours today. Please do not go on the property without a confirmed appointment. Schedule a tour today.

1 Beds ⋅ 1 Baths ⋅ 1036155 MLS

Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted ceiling that's well suited for year-round living. The flexible layout allows you to use the home as either a one- or two-bedroom, depending on your needs. Imagine enjoying dinner every evening with the lake as your backdrop or unwinding on the rear deck while taking in the beautiful water views. From morning coffee at sunrise to relaxing evenings by the water, this home offers a peaceful place to create lasting memories with loved ones and friends. You will enjoy the benefit a spacious basement and a detached one-car garage, providing plenty of storage for outdoor equipment, seasonal items, or hobbies. Situated on nearly half an acre with mature trees for an added buffer of privacy, there's ample room for outdoor activities, entertaining, gardening, or simply enjoying the open space. Whether you're looking for a full-time residence or a weekend retreat this oasis offers the comfort, charm, and lifestyle that make lakefront living so special. It all awaits you! Make it yours today. Please do not go on the property without a confirmed appointment. Schedule a tour today.

31 Lake Shore Drive, Pine Plains

$359,000

Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed.

3 Beds ⋅ 1 Baths ⋅ 1028565 MLS

Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed.

2795 Church Street, Pine Plains

$1,695,000

Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and Millerton, and 20 minutes to Millbrook.

3 Beds ⋅ 3 Baths ⋅ 1010636 MLS

Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and Millerton, and 20 minutes to Millbrook.

1504 Route 83, Pine Plains

$1,495,000

Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.

3 Beds ⋅ 3 Baths ⋅ 987176 MLS

Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.

617 BEAN RIVER Road, Pine Plains

$3,895,000

Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard siding and a welcoming front porch set the stage for a home that seamlessly blends 19th-century soul with modern amenities. Step onto original wide-plank flooring and admire the stunning, exposed hand-hewn beams. An oversized living room features a wood-burning fireplace and panoramic views from three exposures, with French doors leading to the expansive property. The formal dining room boasts an additional fireplace and two large china closets. The professionally equipped kitchen includes dual sinks, a premium professional range, a built-in refrigerator, and a sunny, south-facing breakfast room with pastoral views. A convenient butler’s pantry and powder room are also included on this level. Head upstairs to four bedrooms (two with fireplaces) and three bathrooms. The main house includes a fully equipped 3-bedroom apartment with a separate entrance—perfect for guests or staff. The property is a true compound, designed for both entertainment and flexibility. A fully outfitted barn includes a 3-bedroom apartment, a gym with a sauna, laundry, a workshop and a very large storage room which can easily be converting into more living space. Other buildings include another barn/workshop, a yoga studio, a 2-car detached garage with a storage loft, and a 60' equipment shed. This parcel offers endless potential for hobby farming, horses/livestock, or creating a private, quiet home office. Located in the desirable Shekomeko Valley, this property offers a rare mix of secluded tranquility and easy access to nearby towns.

10 Beds ⋅ 7 Baths ⋅ 953909 MLS

Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard siding and a welcoming front porch set the stage for a home that seamlessly blends 19th-century soul with modern amenities. Step onto original wide-plank flooring and admire the stunning, exposed hand-hewn beams. An oversized living room features a wood-burning fireplace and panoramic views from three exposures, with French doors leading to the expansive property. The formal dining room boasts an additional fireplace and two large china closets. The professionally equipped kitchen includes dual sinks, a premium professional range, a built-in refrigerator, and a sunny, south-facing breakfast room with pastoral views. A convenient butler’s pantry and powder room are also included on this level. Head upstairs to four bedrooms (two with fireplaces) and three bathrooms. The main house includes a fully equipped 3-bedroom apartment with a separate entrance—perfect for guests or staff. The property is a true compound, designed for both entertainment and flexibility. A fully outfitted barn includes a 3-bedroom apartment, a gym with a sauna, laundry, a workshop and a very large storage room which can easily be converting into more living space. Other buildings include another barn/workshop, a yoga studio, a 2-car detached garage with a storage loft, and a 60' equipment shed. This parcel offers endless potential for hobby farming, horses/livestock, or creating a private, quiet home office. Located in the desirable Shekomeko Valley, this property offers a rare mix of secluded tranquility and easy access to nearby towns.

1515-1517 Route 83, Pine Plains

$698,000

A Distinctive Commercial Opportunity in the Heart of Pine Plains Once a cherished church, this remarkable building has been thoughtfully transformed into a dynamic commercial space—ideal for retail, studio, gallery, or a variety of creative ventures. Positioned right on Main Street among beloved local businesses, it offers unmatched charm and visibility. A grand entrance awaits with wide stone steps and iconic yellow doors that open into a welcoming lobby. From here, explore the soaring main hall, the spacious lower level, or the airy loft. The main floor captivates with its dramatic cathedral ceilings, sweeping open layout, and abundant natural light pouring through oversized windows. Original wide-board hardwood floors lend historic character, while ceiling fans and versatile track lighting enhance comfort and ambiance. The loft overlooks this inspiring space, perfect for display, seating, or additional workspace. Downstairs, the lower level offers generous square footage with tall ceilings and bright natural light from ground-level windows. A built-in bar, worktables, and a convenient half bath make this level highly functional and full of potential. Pine Plains is a thriving hub within the Hudson Valley, drawing both locals and visitors traveling along Route 199 between Connecticut, Dutchess County, and the river towns of Hudson and Kingston. Just two hours from NYC, the area benefits from a strong mix of residents, tourists, and second-home owners—supporting a lively business environment. Endless possibilities await in this one-of-a-kind commercial property. Create your next venture in a space that truly stands apart.

938910 MLS

A Distinctive Commercial Opportunity in the Heart of Pine Plains Once a cherished church, this remarkable building has been thoughtfully transformed into a dynamic commercial space—ideal for retail, studio, gallery, or a variety of creative ventures. Positioned right on Main Street among beloved local businesses, it offers unmatched charm and visibility. A grand entrance awaits with wide stone steps and iconic yellow doors that open into a welcoming lobby. From here, explore the soaring main hall, the spacious lower level, or the airy loft. The main floor captivates with its dramatic cathedral ceilings, sweeping open layout, and abundant natural light pouring through oversized windows. Original wide-board hardwood floors lend historic character, while ceiling fans and versatile track lighting enhance comfort and ambiance. The loft overlooks this inspiring space, perfect for display, seating, or additional workspace. Downstairs, the lower level offers generous square footage with tall ceilings and bright natural light from ground-level windows. A built-in bar, worktables, and a convenient half bath make this level highly functional and full of potential. Pine Plains is a thriving hub within the Hudson Valley, drawing both locals and visitors traveling along Route 199 between Connecticut, Dutchess County, and the river towns of Hudson and Kingston. Just two hours from NYC, the area benefits from a strong mix of residents, tourists, and second-home owners—supporting a lively business environment. Endless possibilities await in this one-of-a-kind commercial property. Create your next venture in a space that truly stands apart.

3007 Church Street, Pine Plains

$485,000

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!

4 Beds ⋅ 3 Baths ⋅ 924504 MLS

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!

82 Lake Road, Pine Plains