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$670,000

Privately set on 3.6 acres in Dover Plains, this spacious Colonial offers a unique and versatile layout with plenty of room to make it your own. Built in 2005, the home features 3 legal bedrooms, 3 full bathrooms and 1 half bathroom, with a standout feature being the legal accessory apartment complete with its own private entrance. The main living space offers a traditional Colonial layout with generous room throughout. Upstairs, the primary bedroom features a walk-in closet and private full bathroom, along with 2 additional bedrooms, a hallway full bathroom and a versatile bonus room ideal for a home office or flex space. The legal accessory apartment adds another level of versatility, featuring its own kitchen, living room, bedroom, full bathroom and separate entrance. Whether used for extended household living, guests or simply additional private space, it is a valuable feature that can be difficult to find. Outside, the 3.6-acre setting provides a sense of privacy and separation with plenty of space to enjoy the property. An above-ground pool offers a great spot to spend summer days, while the surrounding acreage provides room for outdoor entertaining, recreation, gardening and more. Located approximately 15 minutes from the Village of Millbrook, the home offers a private country setting while remaining convenient to local shopping, dining and area amenities. With its acreage, flexible floor plan and legal accessory apartment, this property offers a combination of space and possibilities ready for its next owner.

3 Beds ⋅ 4 Baths ⋅ 1049190 MLS

Privately set on 3.6 acres in Dover Plains, this spacious Colonial offers a unique and versatile layout with plenty of room to make it your own. Built in 2005, the home features 3 legal bedrooms, 3 full bathrooms and 1 half bathroom, with a standout feature being the legal accessory apartment complete with its own private entrance. The main living space offers a traditional Colonial layout with generous room throughout. Upstairs, the primary bedroom features a walk-in closet and private full bathroom, along with 2 additional bedrooms, a hallway full bathroom and a versatile bonus room ideal for a home office or flex space. The legal accessory apartment adds another level of versatility, featuring its own kitchen, living room, bedroom, full bathroom and separate entrance. Whether used for extended household living, guests or simply additional private space, it is a valuable feature that can be difficult to find. Outside, the 3.6-acre setting provides a sense of privacy and separation with plenty of space to enjoy the property. An above-ground pool offers a great spot to spend summer days, while the surrounding acreage provides room for outdoor entertaining, recreation, gardening and more. Located approximately 15 minutes from the Village of Millbrook, the home offers a private country setting while remaining convenient to local shopping, dining and area amenities. With its acreage, flexible floor plan and legal accessory apartment, this property offers a combination of space and possibilities ready for its next owner.

250 Highview Road, Dover Plains

$499,000

Tastefully updated 3 bedroom, 2.5 bathroom raised ranch with incredible backyard oasis. Ideal for relaxing or entertaining, this home includes an updated kitchen w/quartz counters & stainless appliances, large living room loaded with natural light and dining room with sliding glass door leading to deck and incredible backyard complete with heated pool & massive patio. Primary bedroom w/ensuite bathroom plus two additional bedrooms and full bathroom on main level. Lower level includes huge family room, laundry room, half bathroom and office/den. New flooring & fresh paint throughout. One car garage for storage. Enjoy the conveniences of 200 amp electric plus a 17kw standby generator. Easy access to local amenities, Wassaic train station, Route 22 and Route 55. Attractively low taxes.

3 Beds ⋅ 3 Baths ⋅ 1043677 MLS

Tastefully updated 3 bedroom, 2.5 bathroom raised ranch with incredible backyard oasis. Ideal for relaxing or entertaining, this home includes an updated kitchen w/quartz counters & stainless appliances, large living room loaded with natural light and dining room with sliding glass door leading to deck and incredible backyard complete with heated pool & massive patio. Primary bedroom w/ensuite bathroom plus two additional bedrooms and full bathroom on main level. Lower level includes huge family room, laundry room, half bathroom and office/den. New flooring & fresh paint throughout. One car garage for storage. Enjoy the conveniences of 200 amp electric plus a 17kw standby generator. Easy access to local amenities, Wassaic train station, Route 22 and Route 55. Attractively low taxes.

45 Nicole Lane, Wingdale

$575,000

Great Colonial home features a wonderful, 40 ft covered front porch, where you can relax and enjoy the lovely view! Spacious Foyer with closet, large, very nice Living Rm with popular LVP flooring, Family Rm with Fireplace & door to deck. The Kitchen features a spacious Dining Area, an Island with a granite top, stainless appliances, propane range. There is also a formal Dining Rm, currently used as an office. Also on the first floor is a pretty half bath and a laundry area. Upstairs, you will find 4 Bedrooms, one of which is the Primary suite. Hall full bath offers a great vanity with a granite top. All bedrooms have ceiling fans! Large 21x23 Two-Car Garage features a very high ceiling. Basement is 24x40. All dimensions are approximate. Siding, Windows, and Roof 2019. Not far from the home are the Dover Schools, Town Library, Dykeman’s Farm and farm stand. Boyce Park in Wingdale offers a playground, baseball field, basketball court and a pavilion. *Metro-North has two nearby train stations, Wingdale and Pawling. Nature lovers will enjoy hiking the Appalachian Trail and exploring the beautiful area of well-known Stone Church in Dover. Short drive to Pawling, where you will find quaint shops, restaurants & pubs, grocery store, gym, medical offices, more.

4 Beds ⋅ 3 Baths ⋅ 1036001 MLS

Great Colonial home features a wonderful, 40 ft covered front porch, where you can relax and enjoy the lovely view! Spacious Foyer with closet, large, very nice Living Rm with popular LVP flooring, Family Rm with Fireplace & door to deck. The Kitchen features a spacious Dining Area, an Island with a granite top, stainless appliances, propane range. There is also a formal Dining Rm, currently used as an office. Also on the first floor is a pretty half bath and a laundry area. Upstairs, you will find 4 Bedrooms, one of which is the Primary suite. Hall full bath offers a great vanity with a granite top. All bedrooms have ceiling fans! Large 21x23 Two-Car Garage features a very high ceiling. Basement is 24x40. All dimensions are approximate. Siding, Windows, and Roof 2019. Not far from the home are the Dover Schools, Town Library, Dykeman’s Farm and farm stand. Boyce Park in Wingdale offers a playground, baseball field, basketball court and a pavilion. *Metro-North has two nearby train stations, Wingdale and Pawling. Nature lovers will enjoy hiking the Appalachian Trail and exploring the beautiful area of well-known Stone Church in Dover. Short drive to Pawling, where you will find quaint shops, restaurants & pubs, grocery store, gym, medical offices, more.

125 Sheldon Road, Wingdale

$899,000

A rare opportunity for the dedicated equestrian, this beautiful gentleman’s farm is set on nearly 9 acres of gently rolling countryside, offering the ideal balance of privacy, usability and convenience. Whether you’re an active competitor, trail rider or simply seeking a peaceful horse property, this special offering provides the setting to pursue your passion. Perfect as a full-time residence or idyllic weekend getaway, the property offers a welcome escape from city life while remaining easily accessible. Horse show enthusiasts will appreciate the convenient proximity to many of the regions’ premier equestrian venues, training facilities and riding opportunities. The nearly 9 acres parcel provides ample space for paddocks, turnout and a sand riding ring. Beyond its equestrian appeal, the property also caters to the automotive enthusiasts. A spacious garage equipped with a vehicle lift provides the ideal place to work on your projects. Adding to the property’s versatility is a legal accessory apartment, perfect for extended family, guests, a caretaker or trainer. Spend your days riding, relaxing and enjoying the beauty of the surrounding countryside, then take advantage of the property’s convenient access to the Harlem Vally-Wingdale train station for seamless travel to and from NYC. Combining the charm for a gentleman’s farm with the lifestyle and conveniences sought by today’s horse owners, car enthusiasts and weekend retreat seekers, this exceptional property is a place where passions can flourish and country living is enjoyed to its fullest.

3 Beds ⋅ 2 Baths ⋅ 1015591 MLS

A rare opportunity for the dedicated equestrian, this beautiful gentleman’s farm is set on nearly 9 acres of gently rolling countryside, offering the ideal balance of privacy, usability and convenience. Whether you’re an active competitor, trail rider or simply seeking a peaceful horse property, this special offering provides the setting to pursue your passion. Perfect as a full-time residence or idyllic weekend getaway, the property offers a welcome escape from city life while remaining easily accessible. Horse show enthusiasts will appreciate the convenient proximity to many of the regions’ premier equestrian venues, training facilities and riding opportunities. The nearly 9 acres parcel provides ample space for paddocks, turnout and a sand riding ring. Beyond its equestrian appeal, the property also caters to the automotive enthusiasts. A spacious garage equipped with a vehicle lift provides the ideal place to work on your projects. Adding to the property’s versatility is a legal accessory apartment, perfect for extended family, guests, a caretaker or trainer. Spend your days riding, relaxing and enjoying the beauty of the surrounding countryside, then take advantage of the property’s convenient access to the Harlem Vally-Wingdale train station for seamless travel to and from NYC. Combining the charm for a gentleman’s farm with the lifestyle and conveniences sought by today’s horse owners, car enthusiasts and weekend retreat seekers, this exceptional property is a place where passions can flourish and country living is enjoyed to its fullest.

73 Lake Ellis Road, Wingdale

$1,250,000

Set on four beautiful acres with sweeping long range views of the foothills and ridges around Litchfield Hills and The Taconic Mountains, this thoughtfully designed contemporary home offers exceptional privacy, tranquility, and quality throughout. Built by the owners for their own use, no expense was spared, with high end materials and meticulous attention to detail. Incredible natural light fills the home, enhanced by oversized windows that capture the surrounding landscape and bring the outdoors in. A gracious front entry welcomes you into the formal living and dining rooms. The living room features a wood-burning fireplace and beautiful views overlooking the backyard and surrounding landscape. The spacious kitchen is designed for both everyday living and entertaining, featuring a large center island, pantry, and sunny eat-in area. The kitchen opens seamlessly to the family room, where oversized windows frame peaceful nature views and fill the space with light. Both rooms open onto a tiered deck overlooking the gardens and distant mountain views, an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The expansive primary suite offers a true retreat with a spacious en-suite bath, walk-in closet, and separate sitting area. A large laundry room is conveniently located off the kitchen and two car garage, while a half bathroom and private office complete the main level. The second floor includes three additional bedrooms, including one with its own en-suite bath, while the remaining two bedrooms share a full bathroom. The lower level offers tremendous flexibility and is currently used as workspace. With large windows and direct exterior access, it presents endless possibilities for future finishing as recreation space, studio, gym, media room, or guest area. A newly built two-story barn is a standout addition to the property, featuring durable Hardie Board siding and superior construction quality. Beautifully landscaped and private, this property offers a rare combination of craftsmanship, comfort, and natural beauty. This property is located in an area of the Hudson Valley known for its scenic beauty, and farm to table restaurants. Less than ten minutes to Metro North Railroad.

4 Beds ⋅ 4 Baths ⋅ 1001139 MLS

Set on four beautiful acres with sweeping long range views of the foothills and ridges around Litchfield Hills and The Taconic Mountains, this thoughtfully designed contemporary home offers exceptional privacy, tranquility, and quality throughout. Built by the owners for their own use, no expense was spared, with high end materials and meticulous attention to detail. Incredible natural light fills the home, enhanced by oversized windows that capture the surrounding landscape and bring the outdoors in. A gracious front entry welcomes you into the formal living and dining rooms. The living room features a wood-burning fireplace and beautiful views overlooking the backyard and surrounding landscape. The spacious kitchen is designed for both everyday living and entertaining, featuring a large center island, pantry, and sunny eat-in area. The kitchen opens seamlessly to the family room, where oversized windows frame peaceful nature views and fill the space with light. Both rooms open onto a tiered deck overlooking the gardens and distant mountain views, an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The expansive primary suite offers a true retreat with a spacious en-suite bath, walk-in closet, and separate sitting area. A large laundry room is conveniently located off the kitchen and two car garage, while a half bathroom and private office complete the main level. The second floor includes three additional bedrooms, including one with its own en-suite bath, while the remaining two bedrooms share a full bathroom. The lower level offers tremendous flexibility and is currently used as workspace. With large windows and direct exterior access, it presents endless possibilities for future finishing as recreation space, studio, gym, media room, or guest area. A newly built two-story barn is a standout addition to the property, featuring durable Hardie Board siding and superior construction quality. Beautifully landscaped and private, this property offers a rare combination of craftsmanship, comfort, and natural beauty. This property is located in an area of the Hudson Valley known for its scenic beauty, and farm to table restaurants. Less than ten minutes to Metro North Railroad.

110 Hillside Avenue, Wingdale

$3,750,000

Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty—three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef’s kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting gatherings. Winding paths traverse a landscape of remarkable diversity—open meadows, mature woodlands, and picturesque waterways—while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation. Just five minutes from Metro-North access in Dover Plains and Ten Mile River, Honey Lane Farm represents a rare convergence of history, scale, and enduring elegance.

7 Beds ⋅ 7 Baths ⋅ 990563 MLS

Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty—three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef’s kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting gatherings. Winding paths traverse a landscape of remarkable diversity—open meadows, mature woodlands, and picturesque waterways—while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation. Just five minutes from Metro-North access in Dover Plains and Ten Mile River, Honey Lane Farm represents a rare convergence of history, scale, and enduring elegance.

151 Benson Hill Road, Dover Plains

$2,475,000

At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a spring-fed pond, orchard, and private hiking trails. The architecture balances tradition and innovation, with a glass breezeway linking the historic structure to a stone and glass master wing—winner of multiple 2025 design awards. Large windows, wide doorways, and a barrier-free layout reflect both aesthetic and practical considerations for modern living and aging in place. Period details like exposed beams, wide-plank floors, and a kitchen fireplace ground the home in its heritage, while updates like solar panels and geothermal temperature control bring it into the future. The kitchen, framed by dark soapstone counters and classic cabinetry, opens to a large screened porch overlooking the backyard and pond. A brick fireplace and custom inset pantry bring both warmth and functionality. The home also includes a temperature-controlled 1,000-bottle wine cellar, ideal for collectors. A two-story barn/garage offers additional workspace or storage. Outdoors, Stone Church Creek winds through the property on its way to the iconic Dover Stone Church Preserve, which directly abuts the rear boundary. This 175-acre protected park features over three miles of well-maintained trails and one of Dutchess County’s most photographed natural features: a dramatic waterfall spilling through a cave carved into ancient stone. With the preserve quite literally at the edge of the property, the connection to nature is immediate and immersive—offering an unmatched sense of privacy and place. Whether as a weekend escape or a full-time homestead, 56 Northrup is a rare blend of design, sustainability, and pastoral beauty—anchored by smart systems, architectural pedigree, and extraordinary surroundings.

4 Beds ⋅ 5 Baths ⋅ 929427 MLS

At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a spring-fed pond, orchard, and private hiking trails. The architecture balances tradition and innovation, with a glass breezeway linking the historic structure to a stone and glass master wing—winner of multiple 2025 design awards. Large windows, wide doorways, and a barrier-free layout reflect both aesthetic and practical considerations for modern living and aging in place. Period details like exposed beams, wide-plank floors, and a kitchen fireplace ground the home in its heritage, while updates like solar panels and geothermal temperature control bring it into the future. The kitchen, framed by dark soapstone counters and classic cabinetry, opens to a large screened porch overlooking the backyard and pond. A brick fireplace and custom inset pantry bring both warmth and functionality. The home also includes a temperature-controlled 1,000-bottle wine cellar, ideal for collectors. A two-story barn/garage offers additional workspace or storage. Outdoors, Stone Church Creek winds through the property on its way to the iconic Dover Stone Church Preserve, which directly abuts the rear boundary. This 175-acre protected park features over three miles of well-maintained trails and one of Dutchess County’s most photographed natural features: a dramatic waterfall spilling through a cave carved into ancient stone. With the preserve quite literally at the edge of the property, the connection to nature is immediate and immersive—offering an unmatched sense of privacy and place. Whether as a weekend escape or a full-time homestead, 56 Northrup is a rare blend of design, sustainability, and pastoral beauty—anchored by smart systems, architectural pedigree, and extraordinary surroundings.

56 Northrup Road, Dover Plains