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$1,975,000

The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era - while still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn’t forget the beautiful, wide-plank wood floors. On the ground floor, you’ll find a large boot room with plenty of storage, a formal dining room, a cozy living room, a wallpapered powder, and the beating heart of the home - the monumental kitchen; a light-filled and dreamy space perfect for entertaining. The second floor has two large bedroom suites with a full bath each, three additional bedrooms, and another full bath. Each bedroom has a subtle but charming color palette, more extraordinary woodwork, and two of the bedrooms have fireplaces. The proportions of the rooms and the layout are well suited to a large family or those with frequent guests, with the two en suites each occupying their own corner of the house, and the three bedrooms and last bathroom in their own wing. The Grounds: Outside, the farmhouse has two ‘faces’ and two beautiful porches. Additionally, a large dining terrace bordered by stone walls sits conveniently off the kitchen. Strolling away from the main house, you’ll find a wrought-iron greenhouse structure and a French parterre garden planted with herbs, lavender, and flowers. The Barn: The Hammertown barn, built in the early 1800s by the founding family of the property, has lived many exciting lives - from being home to elephants from the Barnum Bailey Circus in the early 1900s to its most recent iteration as the main outpost of a beloved furnishings and antiques brand. The barn’s soaring beams and incredible staircase welcome you into the structure, where multiple rooms serve various purposes - including plenty of living space (the perfect place for a home theater), open, sprawling areas with soaring ceilings ideal for hosting large groups, and an abundance of utility, office, and storage space. The barn is fully serviced with electric, air conditioning and heat, and plumbing (including a bathroom). The Guest House: The two-bedroom, two-bath guest cottage was built to elegantly blend with the property's historic character and features multiple fireplaces and detailed millwork. The double-height great room’s arched window floods the house with warm light, and French doors lead to the cottage’s sweet outdoor terrace. The Surroundings: Hammertown is just minutes from Pine Plains, less than fifteen minutes from Millerton and the Connecticut border, and two hours from New York City. The area is defined by some of the most beautiful country landscapes in the region, and is full of hiking trails, thriving local farms, and wonderful small towns and communities. As a marvelously well-serviced compound, Hammertown has incredible potential for those who also wish to explore live-work opportunities, having been home to multiple tasteful commercial ventures and events over the past several decades.

7 Beds ⋅ 6 Baths ⋅ 1022023 MLS

The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era - while still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn’t forget the beautiful, wide-plank wood floors. On the ground floor, you’ll find a large boot room with plenty of storage, a formal dining room, a cozy living room, a wallpapered powder, and the beating heart of the home - the monumental kitchen; a light-filled and dreamy space perfect for entertaining. The second floor has two large bedroom suites with a full bath each, three additional bedrooms, and another full bath. Each bedroom has a subtle but charming color palette, more extraordinary woodwork, and two of the bedrooms have fireplaces. The proportions of the rooms and the layout are well suited to a large family or those with frequent guests, with the two en suites each occupying their own corner of the house, and the three bedrooms and last bathroom in their own wing. The Grounds: Outside, the farmhouse has two ‘faces’ and two beautiful porches. Additionally, a large dining terrace bordered by stone walls sits conveniently off the kitchen. Strolling away from the main house, you’ll find a wrought-iron greenhouse structure and a French parterre garden planted with herbs, lavender, and flowers. The Barn: The Hammertown barn, built in the early 1800s by the founding family of the property, has lived many exciting lives - from being home to elephants from the Barnum Bailey Circus in the early 1900s to its most recent iteration as the main outpost of a beloved furnishings and antiques brand. The barn’s soaring beams and incredible staircase welcome you into the structure, where multiple rooms serve various purposes - including plenty of living space (the perfect place for a home theater), open, sprawling areas with soaring ceilings ideal for hosting large groups, and an abundance of utility, office, and storage space. The barn is fully serviced with electric, air conditioning and heat, and plumbing (including a bathroom). The Guest House: The two-bedroom, two-bath guest cottage was built to elegantly blend with the property's historic character and features multiple fireplaces and detailed millwork. The double-height great room’s arched window floods the house with warm light, and French doors lead to the cottage’s sweet outdoor terrace. The Surroundings: Hammertown is just minutes from Pine Plains, less than fifteen minutes from Millerton and the Connecticut border, and two hours from New York City. The area is defined by some of the most beautiful country landscapes in the region, and is full of hiking trails, thriving local farms, and wonderful small towns and communities. As a marvelously well-serviced compound, Hammertown has incredible potential for those who also wish to explore live-work opportunities, having been home to multiple tasteful commercial ventures and events over the past several decades.

85 Hammertown Road, Pine Plains

$845,000

Look at this wonderful opportunity to own a beloved Hudson Valley restaurant and event venue with breathtaking Stissing Mountain views. Formerly a very successful Italian American restaurant, this 3,538 sq. ft. establishment on 3.1 acres features a spacious bar and tavern, separate dining room with double fireplace, and a 900 sq. ft. fully equipped kitchen. Enjoy sunsets from the tented patio or host private events in the newly renovated bridal suite with kitchenette and bath. Sealed concrete floors, ample parking, and thoughtful layout make this a turnkey opportunity for an experienced restaurateur or entrepreneur. Locals and visitors alike would love to see this Pine Plains landmark come back to life!

930663 MLS

Look at this wonderful opportunity to own a beloved Hudson Valley restaurant and event venue with breathtaking Stissing Mountain views. Formerly a very successful Italian American restaurant, this 3,538 sq. ft. establishment on 3.1 acres features a spacious bar and tavern, separate dining room with double fireplace, and a 900 sq. ft. fully equipped kitchen. Enjoy sunsets from the tented patio or host private events in the newly renovated bridal suite with kitchenette and bath. Sealed concrete floors, ample parking, and thoughtful layout make this a turnkey opportunity for an experienced restaurateur or entrepreneur. Locals and visitors alike would love to see this Pine Plains landmark come back to life!

7685 Route 82, Pine Plains

$639,000

Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.

3 Beds ⋅ 3 Baths ⋅ 1006576 MLS

Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.

553 Lake Road, Pine Plains

$549,000

Enjoy nature on your own 43 scenic acres located on Hicks Hill Road and additional access from Knob Hill Road, which is across from 600 acres of protected land that can not be developed offering exceptional long term privacy. A versatile existing barn provides potential for a variety of uses. With over 1,400 feet of road frontage on Hicks Hill Road and electric available on the property, this parcel is well suited for estate living or development. Convenient to the Taconic Parkway and popular towns of Red Hook, Rhinebeck, Millbrook and only 90 minutes to NYC. Come enjoy country living at its best! Please note there are two parcels combined to comprise the acreage, Lot 732572 with 43.25 acres and Lot 71506 with .44 of an acre with barn. Taxes and assessment reflect the two parcels

951158 MLS

Enjoy nature on your own 43 scenic acres located on Hicks Hill Road and additional access from Knob Hill Road, which is across from 600 acres of protected land that can not be developed offering exceptional long term privacy. A versatile existing barn provides potential for a variety of uses. With over 1,400 feet of road frontage on Hicks Hill Road and electric available on the property, this parcel is well suited for estate living or development. Convenient to the Taconic Parkway and popular towns of Red Hook, Rhinebeck, Millbrook and only 90 minutes to NYC. Come enjoy country living at its best! Please note there are two parcels combined to comprise the acreage, Lot 732572 with 43.25 acres and Lot 71506 with .44 of an acre with barn. Taxes and assessment reflect the two parcels

TBD Hicks Hill Road, Pine Plains

$394,000

Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise. Laundry room off the kitchen for convenience. Back off the living room is your primary suite, room for all your furniture and has a massive ensuite bathroom with soaking tub and shower, skylights bathe the room in sunlight. Off the dining room is a large living room with room for all. Two guest bedrooms stretch off the living room. Full guest Bathroom with tub on this wing of the home. High efficiency Split Units keep the home cool and supplement heat. Outside there is a world of possibilities for the craftsman, car enthusiast, or artist or artisan for Studio space, with an oversized two car garage with lofted storage, heat and electric in here. Then enter the massive 1287 square foot Garage with space for all your needs, storage or uses. In there there is electric, heat, and water. Additional Shed outside for storage,. Yard is perfect for all your needs, and is already outfitted with an invisible fence for your Furry family members. In the heart of Pulvers Corner, 5 minutes to Pine Plains Village, 10 minutes to Stanfordville and Millerton this is a fabulous location.

3 Beds ⋅ 2 Baths ⋅ 988822 MLS

Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise. Laundry room off the kitchen for convenience. Back off the living room is your primary suite, room for all your furniture and has a massive ensuite bathroom with soaking tub and shower, skylights bathe the room in sunlight. Off the dining room is a large living room with room for all. Two guest bedrooms stretch off the living room. Full guest Bathroom with tub on this wing of the home. High efficiency Split Units keep the home cool and supplement heat. Outside there is a world of possibilities for the craftsman, car enthusiast, or artist or artisan for Studio space, with an oversized two car garage with lofted storage, heat and electric in here. Then enter the massive 1287 square foot Garage with space for all your needs, storage or uses. In there there is electric, heat, and water. Additional Shed outside for storage,. Yard is perfect for all your needs, and is already outfitted with an invisible fence for your Furry family members. In the heart of Pulvers Corner, 5 minutes to Pine Plains Village, 10 minutes to Stanfordville and Millerton this is a fabulous location.

3838 Route 199, Pine Plains

$300,000

Nestled on a peaceful corner lot spanning nearly an acre, this 4 bedroom 2 bath ranch offers the perfect blend of privacy, tranquility, and convenience. Located in a quiet, well-establish neighborhood, you’ll enjoy a serene setting while remaining just minutes from local restaurants, shops, and schools. The home features a spacious single-level layout with endless potential for those looking to make it their own. Whether you’re an investor, renovator, or buyer eager to create your dream home, this property is a fantastic opportunity to build equity in a desirable location. Highlight features include a living room with a fireplace, oversized windows for natural light, an above ground pool that just needs a liner, and a spacious deck overlooking an expansive yard. There is plenty of storage in the full basement with garage access.

4 Beds ⋅ 2 Baths ⋅ 1015763 MLS

Nestled on a peaceful corner lot spanning nearly an acre, this 4 bedroom 2 bath ranch offers the perfect blend of privacy, tranquility, and convenience. Located in a quiet, well-establish neighborhood, you’ll enjoy a serene setting while remaining just minutes from local restaurants, shops, and schools. The home features a spacious single-level layout with endless potential for those looking to make it their own. Whether you’re an investor, renovator, or buyer eager to create your dream home, this property is a fantastic opportunity to build equity in a desirable location. Highlight features include a living room with a fireplace, oversized windows for natural light, an above ground pool that just needs a liner, and a spacious deck overlooking an expansive yard. There is plenty of storage in the full basement with garage access.

18 Wicks Avenue, Pine Plains

$110,000

This parcel is your blank canvas and ready for you to create your dream. Conveniently located to the villages of Pine Plains and Millerton. This great lot facing south awaits the perfect house or just a picnic. The land is partially cleared and easy to see. Located amongst beautiful farm land and many local farm stands.

1015122 MLS

This parcel is your blank canvas and ready for you to create your dream. Conveniently located to the villages of Pine Plains and Millerton. This great lot facing south awaits the perfect house or just a picnic. The land is partially cleared and easy to see. Located amongst beautiful farm land and many local farm stands.

Rt-199, Pine Plains

$107,750

Opportunity awaits in the heart of Pine Plains! This 3-bedroom, 1-bath manufactured home, built in 1976, is set on a spacious 0.53-acre lot within the Pine Plains Central School District. Offering 792 square feet of living space, the property presents a wonderful opportunity for a buyer or investor looking to update and personalize a home to suit their vision. The generous lot provides space to enjoy the outdoors while the convenient location offers easy access to local schools, village amenities, dining, shopping, and the surrounding Hudson Valley countryside. Whether you're looking for a project, an investment, or a chance to create a home in a charming community, this property offers plenty of potential.

3 Beds ⋅ 1 Baths ⋅ 1038221 MLS

Opportunity awaits in the heart of Pine Plains! This 3-bedroom, 1-bath manufactured home, built in 1976, is set on a spacious 0.53-acre lot within the Pine Plains Central School District. Offering 792 square feet of living space, the property presents a wonderful opportunity for a buyer or investor looking to update and personalize a home to suit their vision. The generous lot provides space to enjoy the outdoors while the convenient location offers easy access to local schools, village amenities, dining, shopping, and the surrounding Hudson Valley countryside. Whether you're looking for a project, an investment, or a chance to create a home in a charming community, this property offers plenty of potential.

7 Woodside Street, Pine Plains