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$495,000

The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s Dream Escape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and serene surroundings establish a sense of total privacy. Inside, the home features 3 spacious bedrooms and 2 full baths, framed by striking A-frame commercial-grade windows that flood the main living spaces with beautiful natural light. Designed for total self-sufficiency and year-round comfort, the property features a top-of-the-line Central Boiler E-Classic outdoor wood furnace, which handles the home's heating by efficiently piping heat through the main furnace to control the lower-level baseboard system—allowing you to heat your home using the land's abundant natural timber. The main home also features central air, a central vacuum system, a water purification system, and a peaceful 3-season room perfect for taking in the wooded views. The basement features a walk-out to the lower level, offering plenty of storage. For absolute peace of mind, a premium Generac backup generator protects the property—fully connected to provide uninterrupted power to both the main home and the detached garage. For the car enthusiast, mechanic, hobbyist, or entrepreneur, the crown jewel of this property is the detached, commercial-grade 3-car garage. Fully equipped with a 4-post lift, a dedicated workshop space, and a compressor.. Combined with the attached 2-car garage on the main house, you have sheltered space for 5+ vehicles and endless projects that can continue seamlessly through any storm. Whether you are launching a business, restoring classics, or seeking a private, high-efficiency homestead, 176 Downing Road offers a lifestyle without limits. ***The personal property is being cleared every day so some pictures may be different.

3 Beds ⋅ 2 Baths ⋅ 1006885 MLS

The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s Dream Escape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and serene surroundings establish a sense of total privacy. Inside, the home features 3 spacious bedrooms and 2 full baths, framed by striking A-frame commercial-grade windows that flood the main living spaces with beautiful natural light. Designed for total self-sufficiency and year-round comfort, the property features a top-of-the-line Central Boiler E-Classic outdoor wood furnace, which handles the home's heating by efficiently piping heat through the main furnace to control the lower-level baseboard system—allowing you to heat your home using the land's abundant natural timber. The main home also features central air, a central vacuum system, a water purification system, and a peaceful 3-season room perfect for taking in the wooded views. The basement features a walk-out to the lower level, offering plenty of storage. For absolute peace of mind, a premium Generac backup generator protects the property—fully connected to provide uninterrupted power to both the main home and the detached garage. For the car enthusiast, mechanic, hobbyist, or entrepreneur, the crown jewel of this property is the detached, commercial-grade 3-car garage. Fully equipped with a 4-post lift, a dedicated workshop space, and a compressor.. Combined with the attached 2-car garage on the main house, you have sheltered space for 5+ vehicles and endless projects that can continue seamlessly through any storm. Whether you are launching a business, restoring classics, or seeking a private, high-efficiency homestead, 176 Downing Road offers a lifestyle without limits. ***The personal property is being cleared every day so some pictures may be different.

176 Downing Road, Pleasant Valley

$799,999

7 Bay Auto body shop available for sale. Tons of storage inside and outside. Mass exposure off state road route 44. Spray booth, bathroom, waiting room and office inside. Minutes from Taconic State Parkway. Seller financing available.

1006702 MLS

7 Bay Auto body shop available for sale. Tons of storage inside and outside. Mass exposure off state road route 44. Spray booth, bathroom, waiting room and office inside. Minutes from Taconic State Parkway. Seller financing available.

1777 Route 44, Pleasant Valley

$549,000

This is a 2 BR PLUS an additional dedicated office. Circular driveway to an All new renovation in beautiful Gretna Hill wooded neighborhood, elegant farms beyond. Mahogany full glass door entry on to black marble foyer. Spacious living/dining room, mahogany doors and trim. Full glass exterior door to 12' x 18' Japanese cedar deck. Hardwood floors throughout. Natural wood and marble kitchen with artisanal details, huge quartz worktop, new appliances. Large closet on back porch. First floor marble half bath and laundry. Primary bedroom with12' long mahogany closet, in-suite white marble and glass shower bath. Second Carrera marble with tub bathroom next to second bedroom with triple mahogany closet. Office with huge windows. 14' x 4' front porch. Perennial gardens, stone columns, steps, borders and walkway. Cedar siding. New windows. This property is self sustaining with private well and septic, clear south facing roof for possible future solar. Spray foam insulation, new heat pump mini split H&C. Minutes east to the Taconic Parkway, minutes west to Poughkeepsie shopping.

2 Beds ⋅ 3 Baths ⋅ 1004244 MLS

This is a 2 BR PLUS an additional dedicated office. Circular driveway to an All new renovation in beautiful Gretna Hill wooded neighborhood, elegant farms beyond. Mahogany full glass door entry on to black marble foyer. Spacious living/dining room, mahogany doors and trim. Full glass exterior door to 12' x 18' Japanese cedar deck. Hardwood floors throughout. Natural wood and marble kitchen with artisanal details, huge quartz worktop, new appliances. Large closet on back porch. First floor marble half bath and laundry. Primary bedroom with12' long mahogany closet, in-suite white marble and glass shower bath. Second Carrera marble with tub bathroom next to second bedroom with triple mahogany closet. Office with huge windows. 14' x 4' front porch. Perennial gardens, stone columns, steps, borders and walkway. Cedar siding. New windows. This property is self sustaining with private well and septic, clear south facing roof for possible future solar. Spray foam insulation, new heat pump mini split H&C. Minutes east to the Taconic Parkway, minutes west to Poughkeepsie shopping.

17 Gretna Hill Road, Pleasant Valley

$475,000

Welcome to 47 Mountain View Drive a privately situated 4-bedroom, 2.5 bath raised ranch nestled on a quiet 1-acre lot in Pleasant Valley, NY. The heavy lifting is already done here. Major mechanical upgrades are complete including a new electrical panel, new PVC and copper plumbing lines, a new furnace, a water softener, and a newer water well pressure tank — giving you a rock-solid foundation that most homes at this price point simply can't offer. The remodeled kitchen features hickory cabinets, quartz countertops, and stainless steel appliances, while hardwood flooring flows throughout much of the home. The primary bedroom includes a fully remodeled ensuite bath, all across 2,912 sq ft of well-proportioned living space. Step outside to a large deck, balcony, and private yard on over an acre — all minutes from Route 55, the Taconic State Parkway, Arlington schools, shopping, and the Poughkeepsie train station. The bones are exceptional and the upside is real. Schedule your private showing today — opportunities like this don't last long.

4 Beds ⋅ 3 Baths ⋅ 1003202 MLS

Welcome to 47 Mountain View Drive a privately situated 4-bedroom, 2.5 bath raised ranch nestled on a quiet 1-acre lot in Pleasant Valley, NY. The heavy lifting is already done here. Major mechanical upgrades are complete including a new electrical panel, new PVC and copper plumbing lines, a new furnace, a water softener, and a newer water well pressure tank — giving you a rock-solid foundation that most homes at this price point simply can't offer. The remodeled kitchen features hickory cabinets, quartz countertops, and stainless steel appliances, while hardwood flooring flows throughout much of the home. The primary bedroom includes a fully remodeled ensuite bath, all across 2,912 sq ft of well-proportioned living space. Step outside to a large deck, balcony, and private yard on over an acre — all minutes from Route 55, the Taconic State Parkway, Arlington schools, shopping, and the Poughkeepsie train station. The bones are exceptional and the upside is real. Schedule your private showing today — opportunities like this don't last long.

47 Mountain View Drive, Pleasant Valley

$1,470,000

Tucked away off the well-traveled path and largely unnoticed, this remarkable 76± acre private parcel offers breathtaking distant and valley views in the heart of the Hudson Valley, just a short drive from sought-after destinations such as Rhinebeck and Millbrook. Currently operating as a successful apple orchard, the property features approximately 50 acres planted with 5 varieties of mature apple trees, supported by years of proven production. This versatile offering presents an exceptional opportunity to continue the orchard operation or explore alternative agricultural uses such as Christmas trees, nursery stock, or additional fruit varieties. Multiple potential homesites throughout the property capture stunning panoramic views of the surrounding countryside and valleys. A large scenic pond, stocked with bass and utilized for irrigation, enhances both the beauty and functionality of the land. Additional improvements include an extensive irrigation system servicing the orchard, two wind machines for frost protection, a substantial metal equipment barn, and a ranch-style camp building used seasonally during harvest. Combining productive farmland, natural beauty, privacy, and extraordinary views, this property offers unparalleled peace and quiet in one of the Hudson Valley’s most desirable regions.

1003510 MLS

Tucked away off the well-traveled path and largely unnoticed, this remarkable 76± acre private parcel offers breathtaking distant and valley views in the heart of the Hudson Valley, just a short drive from sought-after destinations such as Rhinebeck and Millbrook. Currently operating as a successful apple orchard, the property features approximately 50 acres planted with 5 varieties of mature apple trees, supported by years of proven production. This versatile offering presents an exceptional opportunity to continue the orchard operation or explore alternative agricultural uses such as Christmas trees, nursery stock, or additional fruit varieties. Multiple potential homesites throughout the property capture stunning panoramic views of the surrounding countryside and valleys. A large scenic pond, stocked with bass and utilized for irrigation, enhances both the beauty and functionality of the land. Additional improvements include an extensive irrigation system servicing the orchard, two wind machines for frost protection, a substantial metal equipment barn, and a ranch-style camp building used seasonally during harvest. Combining productive farmland, natural beauty, privacy, and extraordinary views, this property offers unparalleled peace and quiet in one of the Hudson Valley’s most desirable regions.

641 North Avenue, Pleasant Valley

$950,000

Welcome to Rombout Retreat! A spacious four bedroom, three bath home offering over 3,000 square feet of beautifully maintained living space on two private acres surrounded by protected agricultural land. This thoughtfully designed home offers multiple living spaces, each with its own warm and inviting atmosphere, with fireplaces in every sitting room as well as an additional fireplace in the primary suite. Blending traditional charm with a contemporary feel, the home offers an easy, comfortable flow throughout that feels both timeless and move-in ready. The first floor opens to a spacious deck perfect for entertaining and enjoying the peaceful surroundings, overlooking lush gardens, a tranquil water feature, and a heated in-ground pool that creates a true retreat- like setting. The outdoor space is equipped with a pool house that provides convenient storage for pool equipment and additional outdoor essentials, while a large front yard further enhances the property's expansive and private setting. The oversized primary suite boasts two walk-in closets and ample space, along with a bright en suite bathroom filled with natural light. Three additional upstairs bedrooms are serviced by a full shared hallway bathroom, while a conveniently located half bath is situated on the first floor. A finished basement provides additional flexible space ideal for a gym, rec room, or playroom. Additional highlights include an attached garage, central air, a water softener system, and meticulously maintained mechanicals throughout. Conveniently located just minutes from Millbrook, Eastdale Village, the Taconic State Parkway, Millbrook Vineyards & Winery, and Adams Fairacre Farms, this truly unique property offers the perfect balance of privacy, convenience, and lifestyle.

4 Beds ⋅ 3 Baths ⋅ 1000852 MLS

Welcome to Rombout Retreat! A spacious four bedroom, three bath home offering over 3,000 square feet of beautifully maintained living space on two private acres surrounded by protected agricultural land. This thoughtfully designed home offers multiple living spaces, each with its own warm and inviting atmosphere, with fireplaces in every sitting room as well as an additional fireplace in the primary suite. Blending traditional charm with a contemporary feel, the home offers an easy, comfortable flow throughout that feels both timeless and move-in ready. The first floor opens to a spacious deck perfect for entertaining and enjoying the peaceful surroundings, overlooking lush gardens, a tranquil water feature, and a heated in-ground pool that creates a true retreat- like setting. The outdoor space is equipped with a pool house that provides convenient storage for pool equipment and additional outdoor essentials, while a large front yard further enhances the property's expansive and private setting. The oversized primary suite boasts two walk-in closets and ample space, along with a bright en suite bathroom filled with natural light. Three additional upstairs bedrooms are serviced by a full shared hallway bathroom, while a conveniently located half bath is situated on the first floor. A finished basement provides additional flexible space ideal for a gym, rec room, or playroom. Additional highlights include an attached garage, central air, a water softener system, and meticulously maintained mechanicals throughout. Conveniently located just minutes from Millbrook, Eastdale Village, the Taconic State Parkway, Millbrook Vineyards & Winery, and Adams Fairacre Farms, this truly unique property offers the perfect balance of privacy, convenience, and lifestyle.

136 Rombout Road, Pleasant Valley

$595,000

Welcome to Turtle Pond Gully, a delightful property in the Hudson Valley. Enjoy country life in this sweet colonial farmhouse located in the town of Pleasant Valley. This 1930s cottage offers immense charm and is the perfect retreat for weekenders or year-round residents. The light-filled home offers a cozy and comfortable interior with beautiful wood floors. Many original details have been preserved and the home has been updated and is well maintained. It has a wonderful dining room with a pellet stove and a French door to a peering porch and another to a lovely sunroom; a stylish kitchen with tin ceiling; a living room with a French door to an attractive side porch. Many recent improvements, including new metal roof, new siding, and an automatic Generac generator. The grounds, with fine plantings, a pond and stone wall borders, have a lovely park-like feel. There is a detached two car barn style garage with a large game room and woodshop. Centrally located in Dutchess County this is a convenient location, within a mile to the Taconic Parkway, 10 miles to Poughkeepsie train station and only a 12 minute drive to Millbrook.

2 Beds ⋅ 2 Baths ⋅ 995827 MLS

Welcome to Turtle Pond Gully, a delightful property in the Hudson Valley. Enjoy country life in this sweet colonial farmhouse located in the town of Pleasant Valley. This 1930s cottage offers immense charm and is the perfect retreat for weekenders or year-round residents. The light-filled home offers a cozy and comfortable interior with beautiful wood floors. Many original details have been preserved and the home has been updated and is well maintained. It has a wonderful dining room with a pellet stove and a French door to a peering porch and another to a lovely sunroom; a stylish kitchen with tin ceiling; a living room with a French door to an attractive side porch. Many recent improvements, including new metal roof, new siding, and an automatic Generac generator. The grounds, with fine plantings, a pond and stone wall borders, have a lovely park-like feel. There is a detached two car barn style garage with a large game room and woodshop. Centrally located in Dutchess County this is a convenient location, within a mile to the Taconic Parkway, 10 miles to Poughkeepsie train station and only a 12 minute drive to Millbrook.

145 Drake Road, Pleasant Valley

$669,900

Be settled in your new home by the start of the school year! Offered for sale by the original owners, this attractive, 4 BR, 2.5 Bth home, on 1.3 private acres, is located in a quiet, no-thru traffic neighborhood just 7 minutes from the Taconic Parkway. The kitchen is open to the family room and features a fireplace and sliding glass door to a recently replaced deck. There are formal living and dining rooms, an oversized laundry area, a half bath and a convenient breezeway where everyone can drop their muddy shoes. Upstairs are 4 spacious bedrooms and 2 full baths. There is also a full attic and walk-out basement so storage will never be an issue. A favorite feature is the 42’ front porch. It’s a great place to read and relax, say hi to your neighbors, or safely enjoy the drama of a summer thunderstorm. Recent improvements include a new, high efficiency boiler, deck, water heater, garage door and openers, carpet in the MBR and guest bedroom, finished hardwood floors and generator hookup. If your kids are into extracurricular activities requiring multiple trips back and forth to the school, you will appreciate that the elementary school is 5 minutes away and the high school less than 8 minutes away. Shopping, the library and James Baird Park are also just minutes away.

4 Beds ⋅ 3 Baths ⋅ 996478 MLS

Be settled in your new home by the start of the school year! Offered for sale by the original owners, this attractive, 4 BR, 2.5 Bth home, on 1.3 private acres, is located in a quiet, no-thru traffic neighborhood just 7 minutes from the Taconic Parkway. The kitchen is open to the family room and features a fireplace and sliding glass door to a recently replaced deck. There are formal living and dining rooms, an oversized laundry area, a half bath and a convenient breezeway where everyone can drop their muddy shoes. Upstairs are 4 spacious bedrooms and 2 full baths. There is also a full attic and walk-out basement so storage will never be an issue. A favorite feature is the 42’ front porch. It’s a great place to read and relax, say hi to your neighbors, or safely enjoy the drama of a summer thunderstorm. Recent improvements include a new, high efficiency boiler, deck, water heater, garage door and openers, carpet in the MBR and guest bedroom, finished hardwood floors and generator hookup. If your kids are into extracurricular activities requiring multiple trips back and forth to the school, you will appreciate that the elementary school is 5 minutes away and the high school less than 8 minutes away. Shopping, the library and James Baird Park are also just minutes away.

76 Rockledge Drive, Pleasant Valley

$695,000

Welcome to 41 Meddaugh Road, a beautifully transformed 4 bedroom, 2.5 bathroom contemporary home with Hudson Valley historic farmhouse charm. Setback from the road, this turnkey home is sited on 1.84 acres and has undergone an extensive ground-up renovation. This property was previously under contract. The buyer was unable to close due to a contingency on their own home sale — not any issue with this property. During that period, sellers completed a full roof rebuild (new sheathing, 30-year warranty) and additional basement improvements. The home is fully move-in ready and priced to reflect these completed upgrades. Nearly all major systems, structural components, and finishes were replaced or upgraded during this full gut renovation. Inside, the home has been completely reimagined with a bright, airy open-concept layout designed for effortless everyday living. Cozy up by the wood-burning fireplace in the spacious living room, or host gatherings in the stunning, brand-new kitchen featuring a large island and updated appliances. From there, sliding glass doors lead directly to a beautiful stone patio—your perfect spot for morning coffee or casual weekend barbecues. Upstairs, there are four comfortable bedrooms, including a spa-inspired primary suite with an oversized walk-in shower and a double vanity. The home also offers interior access to the attached garage and full unfinished basement. Located in the Town of LaGrange with a Pleasant Valley postal address and within the Arlington Central School District, the property is approximately 5 minutes to the Taconic State Parkway and 20 minutes to the Poughkeepsie Train Station. Looking for outdoor adventures in the area? Visit the scenic trails at the nearby James Baird State Park or take a peaceful walk through the Taconic Hereford Multiple Use Area. Every major structural, heating, and cooling element of this home has been newly upgraded (including a high-efficiency Bosch heat pump system and a brand-new roof) to ensure total peace of mind for its next owner. It is entirely move-in ready and waiting for you to start your next chapter.

4 Beds ⋅ 3 Baths ⋅ 996853 MLS

Welcome to 41 Meddaugh Road, a beautifully transformed 4 bedroom, 2.5 bathroom contemporary home with Hudson Valley historic farmhouse charm. Setback from the road, this turnkey home is sited on 1.84 acres and has undergone an extensive ground-up renovation. This property was previously under contract. The buyer was unable to close due to a contingency on their own home sale — not any issue with this property. During that period, sellers completed a full roof rebuild (new sheathing, 30-year warranty) and additional basement improvements. The home is fully move-in ready and priced to reflect these completed upgrades. Nearly all major systems, structural components, and finishes were replaced or upgraded during this full gut renovation. Inside, the home has been completely reimagined with a bright, airy open-concept layout designed for effortless everyday living. Cozy up by the wood-burning fireplace in the spacious living room, or host gatherings in the stunning, brand-new kitchen featuring a large island and updated appliances. From there, sliding glass doors lead directly to a beautiful stone patio—your perfect spot for morning coffee or casual weekend barbecues. Upstairs, there are four comfortable bedrooms, including a spa-inspired primary suite with an oversized walk-in shower and a double vanity. The home also offers interior access to the attached garage and full unfinished basement. Located in the Town of LaGrange with a Pleasant Valley postal address and within the Arlington Central School District, the property is approximately 5 minutes to the Taconic State Parkway and 20 minutes to the Poughkeepsie Train Station. Looking for outdoor adventures in the area? Visit the scenic trails at the nearby James Baird State Park or take a peaceful walk through the Taconic Hereford Multiple Use Area. Every major structural, heating, and cooling element of this home has been newly upgraded (including a high-efficiency Bosch heat pump system and a brand-new roof) to ensure total peace of mind for its next owner. It is entirely move-in ready and waiting for you to start your next chapter.

41 Meddaugh Road, Pleasant Valley

$565,000

Welcome to 66 Gretna Road — a beautifully spacious home filled with character and natural light, featuring soaring ceilings, oversized windows, a welcoming rocking chair front porch, and a rear deck off the kitchen overlooking the expansive backyard. This move-in ready residence offers a combination of space, flexibility, and convenience within the Arlington School District. The kitchen has wood cabinets, new stainless steel appliances, tile backsplash and a walk-in pantry. Oak hardwood floors are throughout the main living level. The primary ensuite has a spacious walk-in closet and a large double-sink vanity. Updated central air conditioning will keep you cool all summer long. The adaptable floor plan includes a walk-out basement and a full walk-up attic, creating endless opportunities for a fitness area, storage, media room, or playroom. A two-car garage completes this wonderful property. Conveniently located just minutes from the Taconic State Parkway, this home is ideally suited for commuters while also offering easy access to outdoor recreation and local amenities. Priced to sell as owners are relocating.

3 Beds ⋅ 3 Baths ⋅ 993060 MLS

Welcome to 66 Gretna Road — a beautifully spacious home filled with character and natural light, featuring soaring ceilings, oversized windows, a welcoming rocking chair front porch, and a rear deck off the kitchen overlooking the expansive backyard. This move-in ready residence offers a combination of space, flexibility, and convenience within the Arlington School District. The kitchen has wood cabinets, new stainless steel appliances, tile backsplash and a walk-in pantry. Oak hardwood floors are throughout the main living level. The primary ensuite has a spacious walk-in closet and a large double-sink vanity. Updated central air conditioning will keep you cool all summer long. The adaptable floor plan includes a walk-out basement and a full walk-up attic, creating endless opportunities for a fitness area, storage, media room, or playroom. A two-car garage completes this wonderful property. Conveniently located just minutes from the Taconic State Parkway, this home is ideally suited for commuters while also offering easy access to outdoor recreation and local amenities. Priced to sell as owners are relocating.

66 Gretna Road, Pleasant Valley

$179,900

Build your dream home on this beautiful 5-acre Board of Health approved parcel in Pleasant Valley, where privacy, natural beauty, and opportunity come together. This exceptional property offers a rare chance to create a custom home or private retreat in a peaceful Hudson Valley setting. Surrounded by mature trees and scenic countryside, the land provides the perfect backdrop for your vision. With five expansive acres, there is ample room for a custom residence, outdoor living spaces, gardens, or recreational enjoyment. The generous acreage offers both flexibility and privacy, ideal for those seeking space and tranquility. Board of Health approval adds significant value and makes the path to building even easier. Whether you envision a weekend escape or forever home, this parcel is ready to bring your plans to life. Located in desirable Pleasant Valley, enjoy the charm of country living while remaining close to local shops, dining, parks, and everyday conveniences. Explore nearby farms, hiking trails, and all the natural beauty the Hudson Valley has to offer, with easy access to commuter routes and the Taconic State Parkway. Rarely does an opportunity like this come along—buildable acreage in a sought-after location with Board of Health approval already in place. Create the lifestyle you’ve been dreaming of on this remarkable property and enjoy the peace, space, and beauty of country living while staying connected to everything the Hudson Valley offers.

981346 MLS

Build your dream home on this beautiful 5-acre Board of Health approved parcel in Pleasant Valley, where privacy, natural beauty, and opportunity come together. This exceptional property offers a rare chance to create a custom home or private retreat in a peaceful Hudson Valley setting. Surrounded by mature trees and scenic countryside, the land provides the perfect backdrop for your vision. With five expansive acres, there is ample room for a custom residence, outdoor living spaces, gardens, or recreational enjoyment. The generous acreage offers both flexibility and privacy, ideal for those seeking space and tranquility. Board of Health approval adds significant value and makes the path to building even easier. Whether you envision a weekend escape or forever home, this parcel is ready to bring your plans to life. Located in desirable Pleasant Valley, enjoy the charm of country living while remaining close to local shops, dining, parks, and everyday conveniences. Explore nearby farms, hiking trails, and all the natural beauty the Hudson Valley has to offer, with easy access to commuter routes and the Taconic State Parkway. Rarely does an opportunity like this come along—buildable acreage in a sought-after location with Board of Health approval already in place. Create the lifestyle you’ve been dreaming of on this remarkable property and enjoy the peace, space, and beauty of country living while staying connected to everything the Hudson Valley offers.

Creek Rd, Pleasant Valley

$1,200,000

Beautiful farming land, currently 2 adjoining tax lots with creek running through one parcel. Currently enrolled in Conservation Easement with designated building envelope. 80-90% tillable.

976894 MLS

Beautiful farming land, currently 2 adjoining tax lots with creek running through one parcel. Currently enrolled in Conservation Easement with designated building envelope. 80-90% tillable.

2010 Salt Point Turnpike, Pleasant Valley

$68,000

Board of Health approved lot in beautiful Pleasant Valley. Just minutes to the Lagrange Town Center, and to the Taconic State Parkway. This is a fantastic location to build a home in the heart of Dutchess County.

978887 MLS

Board of Health approved lot in beautiful Pleasant Valley. Just minutes to the Lagrange Town Center, and to the Taconic State Parkway. This is a fantastic location to build a home in the heart of Dutchess County.

Frost Hill Road, Pleasant Valley

$600,000

Endless Possibilities Await! This rare property zoned High Density Residential spans 4.63 acres with exceptional road frontage and visibility on Route 44—a prime location for your next investment. The property features a charming 1915 Colonial full of character and potential, ready for restoration. Out back, enjoy a Gunite pool overlooking the serene Wappingers Creek, with over 600 feet of water frontage—a perfect setting for relaxation or future development. In addition to the main house, the property includes: An office building with a 2-bedroom, 2-bath apartment above , currently renting for $1650 and A double-wide home offering additional rental income of $1900 . This property needs a start fresh—tear down or work with what you have and reimagine the site as you wish. Whether you’re looking to invest, develop, or create a live/work space, this property is a blank canvas with incredible potential. Bring your vision and your buyers—this is the opportunity you’ve been waiting for!

966628 MLS

Endless Possibilities Await! This rare property zoned High Density Residential spans 4.63 acres with exceptional road frontage and visibility on Route 44—a prime location for your next investment. The property features a charming 1915 Colonial full of character and potential, ready for restoration. Out back, enjoy a Gunite pool overlooking the serene Wappingers Creek, with over 600 feet of water frontage—a perfect setting for relaxation or future development. In addition to the main house, the property includes: An office building with a 2-bedroom, 2-bath apartment above , currently renting for $1650 and A double-wide home offering additional rental income of $1900 . This property needs a start fresh—tear down or work with what you have and reimagine the site as you wish. Whether you’re looking to invest, develop, or create a live/work space, this property is a blank canvas with incredible potential. Bring your vision and your buyers—this is the opportunity you’ve been waiting for!

1380 Route 44, Pleasant Valley

$1,195,000

Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind residence and companion pool house, creating a private retreat unlike anything else available in the Hudson Valley. From the moment you arrive, the home’s timeless architecture tells a story. Inside, soaring vaulted ceilings, original hand-hewn beams, wide-plank floors, and authentic post-and-beam construction showcase the craftsmanship of a bygone era while providing the comfort and functionality today’s buyers expect. Expansive walls of glass flood the interior with natural light and frame views of the surrounding countryside, creating a seamless connection between indoor and outdoor living. The main residence offers warm, inviting living spaces designed for both everyday living and entertaining. Rich architectural details, exposed timber framing, and carefully preserved historic elements create a sense of authenticity rarely found in modern construction. Every room balances rustic elegance with refined finishes, resulting in a home that feels both sophisticated and welcoming. Complementing the main residence is a beautifully converted barn pool house, providing exceptional flexibility for guests, entertaining, creative pursuits, or a private wellness retreat. The outdoor spaces are equally impressive, offering a peaceful setting to relax, gather, and enjoy the natural beauty of Dutchess County. Located just minutes from Millbrook, Rhinebeck, Poughkeepsie, and the region’s renowned farms, wineries, restaurants, and outdoor recreation, this property delivers the best of Hudson Valley living while remaining easily accessible to New York City. Whether you’re searching for a luxury barn conversion, a post-and-beam home, a historic country estate, or a weekend retreat in the Hudson Valley, 101 Drake Road represents a truly rare offering where history, architecture, and modern comfort come together in perfect balance.

3 Beds ⋅ 3 Baths ⋅ 951502 MLS

Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind residence and companion pool house, creating a private retreat unlike anything else available in the Hudson Valley. From the moment you arrive, the home’s timeless architecture tells a story. Inside, soaring vaulted ceilings, original hand-hewn beams, wide-plank floors, and authentic post-and-beam construction showcase the craftsmanship of a bygone era while providing the comfort and functionality today’s buyers expect. Expansive walls of glass flood the interior with natural light and frame views of the surrounding countryside, creating a seamless connection between indoor and outdoor living. The main residence offers warm, inviting living spaces designed for both everyday living and entertaining. Rich architectural details, exposed timber framing, and carefully preserved historic elements create a sense of authenticity rarely found in modern construction. Every room balances rustic elegance with refined finishes, resulting in a home that feels both sophisticated and welcoming. Complementing the main residence is a beautifully converted barn pool house, providing exceptional flexibility for guests, entertaining, creative pursuits, or a private wellness retreat. The outdoor spaces are equally impressive, offering a peaceful setting to relax, gather, and enjoy the natural beauty of Dutchess County. Located just minutes from Millbrook, Rhinebeck, Poughkeepsie, and the region’s renowned farms, wineries, restaurants, and outdoor recreation, this property delivers the best of Hudson Valley living while remaining easily accessible to New York City. Whether you’re searching for a luxury barn conversion, a post-and-beam home, a historic country estate, or a weekend retreat in the Hudson Valley, 101 Drake Road represents a truly rare offering where history, architecture, and modern comfort come together in perfect balance.

101 Drake Road, Pleasant Valley

$1,750,000

Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: Sarah famously sent cheese from her dairy to George Washington's encampment nearby. Over the years, the home has flown both British and American flags, bearing witness to centuries of change. Set on approximately 18 serene acres with subdivision potential for three 3.5-acre lots, the estate includes a beautifully restored 6-bedroom, 4-bathroom residence. Carefully updated to preserve its character, the home features original wide-plank hardwood floors, massive Dutch doors with original hardware, six corner Rumford fireplaces, designer lighting, crown molding, and a fully renovated chef’s kitchen with an eat-in area. Enjoy formal and casual living spaces, including a dining room, living room, and family room. Modern upgrades include new central air, central vacuum, and oil heating with an above-ground tank. Additional amenities include a soaking tub, stall shower, and dedicated dressing area. Property taxes have been lowered for the 2025 tax season, offering immediate financial relief—and there is further potential for tax breaks should the new owner choose to start a small farm operation. Outdoors, unwind on the 50-foot veranda overlooking a tranquil pond and rolling pastures. A charming tiny house by a seasonal brook offers extra retreat space, while two large barns serve various purposes—one equipped with horse stalls and a commercial woodworking shop, the other perfect for additional stabling or storage. An outdoor cabana adds another space for relaxation or entertaining. This estate is being sold as-is by motivated sellers who have poured love and care into its restoration. Whether you're an equestrian, a history enthusiast, or a visionary investor, this property offers endless potential—from farming (which may bring additional tax benefits) to development or simply enjoying the luxury of rural elegance.

6 Beds ⋅ 4 Baths ⋅ 886347 MLS

Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: Sarah famously sent cheese from her dairy to George Washington's encampment nearby. Over the years, the home has flown both British and American flags, bearing witness to centuries of change. Set on approximately 18 serene acres with subdivision potential for three 3.5-acre lots, the estate includes a beautifully restored 6-bedroom, 4-bathroom residence. Carefully updated to preserve its character, the home features original wide-plank hardwood floors, massive Dutch doors with original hardware, six corner Rumford fireplaces, designer lighting, crown molding, and a fully renovated chef’s kitchen with an eat-in area. Enjoy formal and casual living spaces, including a dining room, living room, and family room. Modern upgrades include new central air, central vacuum, and oil heating with an above-ground tank. Additional amenities include a soaking tub, stall shower, and dedicated dressing area. Property taxes have been lowered for the 2025 tax season, offering immediate financial relief—and there is further potential for tax breaks should the new owner choose to start a small farm operation. Outdoors, unwind on the 50-foot veranda overlooking a tranquil pond and rolling pastures. A charming tiny house by a seasonal brook offers extra retreat space, while two large barns serve various purposes—one equipped with horse stalls and a commercial woodworking shop, the other perfect for additional stabling or storage. An outdoor cabana adds another space for relaxation or entertaining. This estate is being sold as-is by motivated sellers who have poured love and care into its restoration. Whether you're an equestrian, a history enthusiast, or a visionary investor, this property offers endless potential—from farming (which may bring additional tax benefits) to development or simply enjoying the luxury of rural elegance.

11 Brown Road, Pleasant Valley

$899,000

This rare two-for-one property, owned by the same family for nearly 40 years, offers an exceptional opportunity in a highly visible, high-traffic corner location. The main building is a spacious, two-story retail/warehouse structure, previously used as a feed store, offering flexible commercial space ideal for retail, offices, warehousing, or light industrial uses. The warehouse includes a loading and unloading area for added convenience. Just steps away, a charming 3-bedroom, 1-bath colonial-style home, set back from the road and surrounded by mature trees and perennial flowers, provides a peaceful living space. This property is perfect for live/work arrangements, with a detached 2-car garage offering ample storage. With both residential and commercial zoning, the possibilities are endless in this desirable location.

873874 MLS

This rare two-for-one property, owned by the same family for nearly 40 years, offers an exceptional opportunity in a highly visible, high-traffic corner location. The main building is a spacious, two-story retail/warehouse structure, previously used as a feed store, offering flexible commercial space ideal for retail, offices, warehousing, or light industrial uses. The warehouse includes a loading and unloading area for added convenience. Just steps away, a charming 3-bedroom, 1-bath colonial-style home, set back from the road and surrounded by mature trees and perennial flowers, provides a peaceful living space. This property is perfect for live/work arrangements, with a detached 2-car garage offering ample storage. With both residential and commercial zoning, the possibilities are endless in this desirable location.

1-7 West Road, Pleasant Valley