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$3,500,000

Set on 5.85 private acres just under 90 minutes from Manhattan, Three Ponds Estate is a fully remodeled 4 bedroom, 3.5 bath residence designed by the owner and designer behind the award winning Millbrook Inn. That pedigree is felt the moment you arrive and carries through every room, from the bespoke finishes to the way the home is oriented to capture its extraordinary setting. Spanning 3,688 square feet, the home was reimagined from the ground up with an eye for craft that is increasingly rare. The layout centers on not one but two primary suites, each with its own walk in closet, offering a flexibility that suits multigenerational living, hosting weekend guests, or simply claiming a wing of your own. Sweeping views of the Catskills and the property's three tranquil ponds can be taken in all in one breath, a backdrop that shifts beautifully with the seasons. A fireplace anchors the main living space and gives the home its center of gravity through the cooler months. The flow throughout is built for both quiet mornings with coffee and full house entertaining, moving easily between the interior and the grounds beyond. The bathrooms are a design statement in themselves, finished in hand glazed terracotta that brings warmth, texture, and a sense of handmade craft to every corner. These are the details that separate a renovation from a true design vision, and they are present at every turn. The full finished walkout basement is a standout in its own right. A large open space, it holds a wine connoisseur's dream cellar and offers the ideal footprint for an in law suite, a media room, or a private retreat. Because it walks out directly to the grounds, it lives with the same light and connection to the outdoors as the rest of the home rather than feeling like a lower level. Outside, the estate truly comes alive. Unwind in the hot tub as the light fades over the ponds, wander the nearly six acres of open and private land, or simply take in the quiet that defines this corner of the Hudson Valley. A roundabout driveway provides a gracious arrival and leads to a detached two car garage, which together with the two car attached garage gives you four garage spaces in total, a genuine rarity at this level. Three Ponds Estate is a turnkey luxury property in one of the Hudson Valley's most coveted towns, combining the privacy of a country estate with an ease of access to the city that few can match. Beautifully finished, thoughtfully designed, and ready for its next chapter. Nothing to do but move in.

4 Beds ⋅ 4 Baths ⋅ 1014296 MLS

Set on 5.85 private acres just under 90 minutes from Manhattan, Three Ponds Estate is a fully remodeled 4 bedroom, 3.5 bath residence designed by the owner and designer behind the award winning Millbrook Inn. That pedigree is felt the moment you arrive and carries through every room, from the bespoke finishes to the way the home is oriented to capture its extraordinary setting. Spanning 3,688 square feet, the home was reimagined from the ground up with an eye for craft that is increasingly rare. The layout centers on not one but two primary suites, each with its own walk in closet, offering a flexibility that suits multigenerational living, hosting weekend guests, or simply claiming a wing of your own. Sweeping views of the Catskills and the property's three tranquil ponds can be taken in all in one breath, a backdrop that shifts beautifully with the seasons. A fireplace anchors the main living space and gives the home its center of gravity through the cooler months. The flow throughout is built for both quiet mornings with coffee and full house entertaining, moving easily between the interior and the grounds beyond. The bathrooms are a design statement in themselves, finished in hand glazed terracotta that brings warmth, texture, and a sense of handmade craft to every corner. These are the details that separate a renovation from a true design vision, and they are present at every turn. The full finished walkout basement is a standout in its own right. A large open space, it holds a wine connoisseur's dream cellar and offers the ideal footprint for an in law suite, a media room, or a private retreat. Because it walks out directly to the grounds, it lives with the same light and connection to the outdoors as the rest of the home rather than feeling like a lower level. Outside, the estate truly comes alive. Unwind in the hot tub as the light fades over the ponds, wander the nearly six acres of open and private land, or simply take in the quiet that defines this corner of the Hudson Valley. A roundabout driveway provides a gracious arrival and leads to a detached two car garage, which together with the two car attached garage gives you four garage spaces in total, a genuine rarity at this level. Three Ponds Estate is a turnkey luxury property in one of the Hudson Valley's most coveted towns, combining the privacy of a country estate with an ease of access to the city that few can match. Beautifully finished, thoughtfully designed, and ready for its next chapter. Nothing to do but move in.

3531 Route 82, Millbrook

$724,900

Escape to this private retreat sited on 1.5 acres, on a country road, minutes to the Village of Millbrook. Imagine what you could do with this property. The two separate structures offer endless possibilities. The huge barn, with a garage below, which can accommodate 8+ cars, is perfect for a car enthusiast or other hobbyist, also includes a 1900 square foot, three bedroom, two-bath finished living space above. The second structure is a beautifully renovated, three-bedroom ranch home. Tasteful landscaping and fieldstone steps lead to a gorgeous entry staircase. As you step inside, you are welcomed by lovely, refinished hardwood floors bathed in natural light from the sun streaming in through the large picture window. You will love the open floor plan. The generous living room flows into the dining space which offers a wide-open view into the kitchen. The kitchen boasts white shaker cabinetry, granite counters, stainless steel appliances, luxury vinyl plank flooring, subway tile backsplash and a more than ample dine-in area. Down the hallway, you will find three bedrooms and a newly renovated bathroom. The fabulous 3 season room is a great addition to the living space. It includes a woodstove, offers wonderful views of the property and includes a grill deck and stairs down to the level back yard. The roof, windows, siding and boiler are brand new. Conveniently located close to highways, Millbrook Vineyards & Winery, local shops, fine dining and all that the fantastic Hudson Valley has to offer.

6 Beds ⋅ 3 Baths ⋅ 1021063 MLS

Escape to this private retreat sited on 1.5 acres, on a country road, minutes to the Village of Millbrook. Imagine what you could do with this property. The two separate structures offer endless possibilities. The huge barn, with a garage below, which can accommodate 8+ cars, is perfect for a car enthusiast or other hobbyist, also includes a 1900 square foot, three bedroom, two-bath finished living space above. The second structure is a beautifully renovated, three-bedroom ranch home. Tasteful landscaping and fieldstone steps lead to a gorgeous entry staircase. As you step inside, you are welcomed by lovely, refinished hardwood floors bathed in natural light from the sun streaming in through the large picture window. You will love the open floor plan. The generous living room flows into the dining space which offers a wide-open view into the kitchen. The kitchen boasts white shaker cabinetry, granite counters, stainless steel appliances, luxury vinyl plank flooring, subway tile backsplash and a more than ample dine-in area. Down the hallway, you will find three bedrooms and a newly renovated bathroom. The fabulous 3 season room is a great addition to the living space. It includes a woodstove, offers wonderful views of the property and includes a grill deck and stairs down to the level back yard. The roof, windows, siding and boiler are brand new. Conveniently located close to highways, Millbrook Vineyards & Winery, local shops, fine dining and all that the fantastic Hudson Valley has to offer.

676-678 Oak Summit Road, Millbrook

$4,250,000

Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated four or five bedroom, three full and two half bath main residence and a separate two bedroom, two and a half bath guest house. A dramatic formal entry with a 19-foot vaulted ceiling creates a grand first impression. Walnut-stained wood floors run throughout much of the home, leading to beautifully designed living spaces designed for both elegant entertaining and everyday comfort. The spacious living room features a fireplace and four sets of French doors opening to the flagstone terrace, while the formal dining room, family room, and double parlor provide a variety of inviting gathering spaces. The chef's kitchen serves as the heart of the home, showcasing custom Plain & Fancy cabinetry, quartz countertops, a Viking six-burner range with grill, Liebherr refrigerator, Bosch dishwasher, and a brick fireplace. A large pantry and first-floor laundry room add convenience and functionality. Upstairs, the primary suite offers a luxurious retreat with a spa-like bath featuring an oversized shower, double vanities, water closet, and an impressive walk-in closet. Three additional bedrooms, a second-floor family room with fireplace, and a library with built-in shelving provide ample space. A third-floor bonus room offers flexibility for a studio, gym or playroom. The guest house is equally appealing, featuring a two-car garage below and a thoughtfully designed upper level with a great room, kitchen, two bedrooms, two baths, loft space, and private deck. Outdoor living is enhanced by a beautiful flagstone terrace that spans the entire length of the home and extensive new landscaping with approximately 300 salvia and 130 limelight hydrangeas. A pool is to be constructed, adding to amenities. This turnkey Hudson Valley estate is located just minutes from the charming Village of Millbrook.

4 Beds ⋅ 5 Baths ⋅ 1012988 MLS

Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated four or five bedroom, three full and two half bath main residence and a separate two bedroom, two and a half bath guest house. A dramatic formal entry with a 19-foot vaulted ceiling creates a grand first impression. Walnut-stained wood floors run throughout much of the home, leading to beautifully designed living spaces designed for both elegant entertaining and everyday comfort. The spacious living room features a fireplace and four sets of French doors opening to the flagstone terrace, while the formal dining room, family room, and double parlor provide a variety of inviting gathering spaces. The chef's kitchen serves as the heart of the home, showcasing custom Plain & Fancy cabinetry, quartz countertops, a Viking six-burner range with grill, Liebherr refrigerator, Bosch dishwasher, and a brick fireplace. A large pantry and first-floor laundry room add convenience and functionality. Upstairs, the primary suite offers a luxurious retreat with a spa-like bath featuring an oversized shower, double vanities, water closet, and an impressive walk-in closet. Three additional bedrooms, a second-floor family room with fireplace, and a library with built-in shelving provide ample space. A third-floor bonus room offers flexibility for a studio, gym or playroom. The guest house is equally appealing, featuring a two-car garage below and a thoughtfully designed upper level with a great room, kitchen, two bedrooms, two baths, loft space, and private deck. Outdoor living is enhanced by a beautiful flagstone terrace that spans the entire length of the home and extensive new landscaping with approximately 300 salvia and 130 limelight hydrangeas. A pool is to be constructed, adding to amenities. This turnkey Hudson Valley estate is located just minutes from the charming Village of Millbrook.

296-302 Stanford Road, Millbrook

$11,500,000

Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance the pastoral beauty while providing a measure of sustainability. The architect Pietro Cicognani designed a home that harmoniously balances details of comfort, beauty, modernity, and history. West Meadow feels as if it’s been in place for centuries. The spacious great room boasts two 18th century stone fireplaces and floors of limestone tile imported from France. Fresh air and light pour in through six custom French doors facing both east and west. The library opens to a long covered porch and one of many stunning views. A central gathering place for friends and loved ones, the kitchen is warmed by a fireplace with pizza oven. In the summer, a wall of floor-to-ceiling windows and doors opens to fragrant gardens, thyme- and lavender-laced stone terraces, the uninterrupted panorama, and matchless sunsets. Upstairs, the primary suite features vaulted ceiling, large windows, and spacious accommodations for luxurious comfort and self-care, including steam shower and a soaking tub that has its very own view. On the bottom floor, a remarkable two thousand bottle wine cellar and tasting room offers something special for oenophiles and casual wine enthusiasts alike. Also on that level is built-in cedar storage, a full laundry, and a staff bedroom. A long, private drive leads through the natural habitat to every outdoor spot on the estate that has been designed for restful ease, comfort, and beauty. Discreetly set apart from the residence, outbuildings include a caretaker’s home, a two-bedroom guest suite, heated greenhouse, four-stall equipment garage, full shop, office, chicken house, and run-in shed. There is ample room on the property for livestock or a stick and ball polo field. Surrounding the house, the columned porch allows for seating in sun or shade, and panoramic views for watching a storm approach, an eagle cavort, or the sun lower in the painted sky.

5 Beds ⋅ 7 Baths ⋅ 1007235 MLS

Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance the pastoral beauty while providing a measure of sustainability. The architect Pietro Cicognani designed a home that harmoniously balances details of comfort, beauty, modernity, and history. West Meadow feels as if it’s been in place for centuries. The spacious great room boasts two 18th century stone fireplaces and floors of limestone tile imported from France. Fresh air and light pour in through six custom French doors facing both east and west. The library opens to a long covered porch and one of many stunning views. A central gathering place for friends and loved ones, the kitchen is warmed by a fireplace with pizza oven. In the summer, a wall of floor-to-ceiling windows and doors opens to fragrant gardens, thyme- and lavender-laced stone terraces, the uninterrupted panorama, and matchless sunsets. Upstairs, the primary suite features vaulted ceiling, large windows, and spacious accommodations for luxurious comfort and self-care, including steam shower and a soaking tub that has its very own view. On the bottom floor, a remarkable two thousand bottle wine cellar and tasting room offers something special for oenophiles and casual wine enthusiasts alike. Also on that level is built-in cedar storage, a full laundry, and a staff bedroom. A long, private drive leads through the natural habitat to every outdoor spot on the estate that has been designed for restful ease, comfort, and beauty. Discreetly set apart from the residence, outbuildings include a caretaker’s home, a two-bedroom guest suite, heated greenhouse, four-stall equipment garage, full shop, office, chicken house, and run-in shed. There is ample room on the property for livestock or a stick and ball polo field. Surrounding the house, the columned porch allows for seating in sun or shade, and panoramic views for watching a storm approach, an eagle cavort, or the sun lower in the painted sky.

129 W Meadow Lane, Millbrook

$1,250,000

Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on 0.21 acres just steps from Millbrook's boutiques, restaurants, galleries, and everyday conveniences, the property offers an increasingly rare combination of village living and income-producing potential. Originally built in 1910, the main residence was extensively renovated in 2002 with new windows, updated heating systems, a new oil tank, and two-zone central air conditioning, blending modern comfort with historic character. The guest apartment was constructedin 2018 and provides excellent flexibility for rental income, guests, or extended family. The private fenced backyard serves as a peaceful retreat, featuring two bluestone patios ideal for outdoor dining, entertaining, or relaxing. Ideally located near highly regarded public and private schools, summer camps, and premier sporting clubs, including the Millbrook Golf & Tennis Club, Tamarack Preserve, and Mashomack Preserve Club. The region is renowned for its equestrian lifestyle, with access to horse shows, fox hunting, riding trails, and top-tier equestrian facilities. Hiking, fly-fishing, polo, and skiing are all nearby. Millbrook's central location provides convenient access to Rhinebeck, Red Hook, Pine Plains, Millerton, Hudson, Litchfield County, and the Berkshires, home to Tanglewood and a wealth of cultural attractions. Just 1¾ hours from Manhattan by car or via Metro-North Railroad, this unique property offers the perfect blend of village convenience, country charm, and income-producing flexibility.

4 Beds ⋅ 3 Baths ⋅ 967644 MLS

Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on 0.21 acres just steps from Millbrook's boutiques, restaurants, galleries, and everyday conveniences, the property offers an increasingly rare combination of village living and income-producing potential. Originally built in 1910, the main residence was extensively renovated in 2002 with new windows, updated heating systems, a new oil tank, and two-zone central air conditioning, blending modern comfort with historic character. The guest apartment was constructedin 2018 and provides excellent flexibility for rental income, guests, or extended family. The private fenced backyard serves as a peaceful retreat, featuring two bluestone patios ideal for outdoor dining, entertaining, or relaxing. Ideally located near highly regarded public and private schools, summer camps, and premier sporting clubs, including the Millbrook Golf & Tennis Club, Tamarack Preserve, and Mashomack Preserve Club. The region is renowned for its equestrian lifestyle, with access to horse shows, fox hunting, riding trails, and top-tier equestrian facilities. Hiking, fly-fishing, polo, and skiing are all nearby. Millbrook's central location provides convenient access to Rhinebeck, Red Hook, Pine Plains, Millerton, Hudson, Litchfield County, and the Berkshires, home to Tanglewood and a wealth of cultural attractions. Just 1¾ hours from Manhattan by car or via Metro-North Railroad, this unique property offers the perfect blend of village convenience, country charm, and income-producing flexibility.

3311 Franklin Avenue, Millbrook

$895,000

Perfectly situated at the end of a long driveway and enjoying complete privacy is this four bedroom Ranch on 8.94 +/- acres offering a picturesque setting and located only minutes to the Village of Millbrook. The lovely interior features an open floor plan with many fine details throughout such as Anderson windows, custom trim and hardwood floors. The spacious open country Kitchen is fully equipped, perfect for entertaining. There is a wonderful light-filled Living Room with cathedral ceiling and wood stove which leads to a deck in the rear. The well-appointed primary Bedroom Suite with full Bath offers an oversized walk-in shower and soaking tub. There are two additional Bedrooms served by one full Bath. It is presently being used as a mother/daughter with an expansive open floor plan to include a separate entrance, one bedroom and den. On the lower level, there is a fabulous Family Room and Game Room. There is an attached four-car garage with plenty of storage space throughout the basement. In addition, there is a detached expansive three bay Garage with workshop area, car lift and plenty of storage. This property offers a wonderful setting with mature trees, stone walls with pretty views of the property.

4 Beds ⋅ 4 Baths ⋅ 958442 MLS

Perfectly situated at the end of a long driveway and enjoying complete privacy is this four bedroom Ranch on 8.94 +/- acres offering a picturesque setting and located only minutes to the Village of Millbrook. The lovely interior features an open floor plan with many fine details throughout such as Anderson windows, custom trim and hardwood floors. The spacious open country Kitchen is fully equipped, perfect for entertaining. There is a wonderful light-filled Living Room with cathedral ceiling and wood stove which leads to a deck in the rear. The well-appointed primary Bedroom Suite with full Bath offers an oversized walk-in shower and soaking tub. There are two additional Bedrooms served by one full Bath. It is presently being used as a mother/daughter with an expansive open floor plan to include a separate entrance, one bedroom and den. On the lower level, there is a fabulous Family Room and Game Room. There is an attached four-car garage with plenty of storage space throughout the basement. In addition, there is a detached expansive three bay Garage with workshop area, car lift and plenty of storage. This property offers a wonderful setting with mature trees, stone walls with pretty views of the property.

35 Appaloosa Lane, Millbrook