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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

$1,625,000

Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential. The light-filled home is defined by soaring 30-foot ceilings and a dramatic sense of volume with Greek revival motifs throughout. The grand entry to the main level flows into an open kitchen area leading to the great room, with a stunning granite fireplace and adjacent open dining area and a generous greenhouse/sunroom which extends the living space. A balcony off the dining-room anchors both sides of the house and offers a sheltered outdoor respite for coffee or cocktails overlooking the peaceful wooded landscape. The other side leads into the guest bedroom and bath, as well as the primary bedroom suite, featuring a dressing area and walk in closet. Separate loft spaces in each bedroom can be enjoyed as open galleries, sleeping areas or reimagined as another floor to expand the interior square footage. Constructed with quarried bluestone and granite, I-beams, a seamless steel roof, custom millwork, and French limestone and oak floors, the house reflects a focus on longevity and craftsmanship. Below, a large cellar is well-suited for a workshop or studio and includes multiple storage rooms including one for wine. This level also offers flexibility for conversion into additional living space. An approximately 1,000-square-foot, four-bay garage provides substantial parking and storage. Additional on-site materials, including granite pavers, brick pavers, a granite bench, and a granite lamp post base, are included in the sale and offer opportunities for future landscape or hardscape projects. The grounds are anchored by a private garden with a granite pathway encircling a grand Robinson iron fountain featuring cranes. A spring-fed brook runs along the southern border of the property, enhancing the natural setting. Approximately 20 acres on the eastern side of the property offer development potential and the possibility of creating additional vantage points. Less than 2 hours from New York City, this Millbrook estate property combines solid architectural pedigree, superior construction and significant landholding in a much sought-after Hudson Valley location, with convenient access to the amenities of Millbrook Village, Dutchess Day School, and the wider Hudson Valley region. *Some photos virtually staged.

3 Beds ⋅ 2 Baths ⋅ 1011800 MLS

Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential. The light-filled home is defined by soaring 30-foot ceilings and a dramatic sense of volume with Greek revival motifs throughout. The grand entry to the main level flows into an open kitchen area leading to the great room, with a stunning granite fireplace and adjacent open dining area and a generous greenhouse/sunroom which extends the living space. A balcony off the dining-room anchors both sides of the house and offers a sheltered outdoor respite for coffee or cocktails overlooking the peaceful wooded landscape. The other side leads into the guest bedroom and bath, as well as the primary bedroom suite, featuring a dressing area and walk in closet. Separate loft spaces in each bedroom can be enjoyed as open galleries, sleeping areas or reimagined as another floor to expand the interior square footage. Constructed with quarried bluestone and granite, I-beams, a seamless steel roof, custom millwork, and French limestone and oak floors, the house reflects a focus on longevity and craftsmanship. Below, a large cellar is well-suited for a workshop or studio and includes multiple storage rooms including one for wine. This level also offers flexibility for conversion into additional living space. An approximately 1,000-square-foot, four-bay garage provides substantial parking and storage. Additional on-site materials, including granite pavers, brick pavers, a granite bench, and a granite lamp post base, are included in the sale and offer opportunities for future landscape or hardscape projects. The grounds are anchored by a private garden with a granite pathway encircling a grand Robinson iron fountain featuring cranes. A spring-fed brook runs along the southern border of the property, enhancing the natural setting. Approximately 20 acres on the eastern side of the property offer development potential and the possibility of creating additional vantage points. Less than 2 hours from New York City, this Millbrook estate property combines solid architectural pedigree, superior construction and significant landholding in a much sought-after Hudson Valley location, with convenient access to the amenities of Millbrook Village, Dutchess Day School, and the wider Hudson Valley region. *Some photos virtually staged.

46 Hoxie Road, Millbrook

$729,000

Charming country Cape Cod style home located minutes from the Village of Millbrook. This home offers an open floor plan with wood flooring, custom built kitchen cabinets, granite countertops, and stainless steel appliances. Dining room has slider to deck. Primary bedroom on first floor with full bath, including washer & dryer. Two large bedrooms are located on the second floor with a second full bath. The basement is finished into a family/game room with walk out slider to yard. The back yard features an in-ground, heated swimming pool and wrap around patio. Whether you are seeking a weekend retreat or a full-time residence, this property offers the perfect blend of easy living and rural charm!

3 Beds ⋅ 2 Baths ⋅ 1007796 MLS

Charming country Cape Cod style home located minutes from the Village of Millbrook. This home offers an open floor plan with wood flooring, custom built kitchen cabinets, granite countertops, and stainless steel appliances. Dining room has slider to deck. Primary bedroom on first floor with full bath, including washer & dryer. Two large bedrooms are located on the second floor with a second full bath. The basement is finished into a family/game room with walk out slider to yard. The back yard features an in-ground, heated swimming pool and wrap around patio. Whether you are seeking a weekend retreat or a full-time residence, this property offers the perfect blend of easy living and rural charm!

580 Oak Summit Road, Millbrook

$4,495,000

**TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort, functionality, and elegant entertaining. Designed for today’s lifestyle, the floor plan includes stunning 2-story great room and foyer, floating staircase, oversized aluminum clad windows throughout, first floor expansive primary suite with his and hers walk-in closets, guest room with en suite full bath, a dedicated home office/flex space and mud room. Custom chef's kitchen is sure to impress with custom in lay cabinetry, Quartz countertops, 5x11 island, 48" range, serving room with additional range and dishwasher and walk-in pantry. Upstairs you will find 2 additional well sized bedrooms with en suite baths, a game room, play room and gym/bonus room, creating flexible spaces for work, wellness, and recreation. The full walk-out basement, complete with 9-foot ceilings, offers endless possibilities for future finishing and additional living space. The exterior showcases striking Hardie Plank board-and-batten siding, while inside, quality construction and energy efficiency take center stage. Premium building materials, spray foam insulation, recessed lighting throughout, and high-efficiency heat pumps for heating and cooling provide year-round comfort and long-term savings. Step outside to your own private retreat, highlighted by a custom gunite saltwater heated pool surrounded by mature landscaping, hardscape and the tranquility and natural beauty of the property. Whether enjoying quiet mornings overlooking the acreage or hosting gatherings with family and friends, this remarkable setting offers the perfect blend of luxury, privacy, and convenience—just moments from the charming village of Millbrook. A rare opportunity to own a newly crafted estate where exceptional design, modern efficiency, and unparalleled privacy come together in one of the Hudson Valley’s most sought-after locations. Builder is offering generous builder specs and allowances. **PHOTOS ARE RENDERINGS OF A SIMILAR MODEL**

4 Beds ⋅ 5 Baths ⋅ 1006093 MLS

**TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort, functionality, and elegant entertaining. Designed for today’s lifestyle, the floor plan includes stunning 2-story great room and foyer, floating staircase, oversized aluminum clad windows throughout, first floor expansive primary suite with his and hers walk-in closets, guest room with en suite full bath, a dedicated home office/flex space and mud room. Custom chef's kitchen is sure to impress with custom in lay cabinetry, Quartz countertops, 5x11 island, 48" range, serving room with additional range and dishwasher and walk-in pantry. Upstairs you will find 2 additional well sized bedrooms with en suite baths, a game room, play room and gym/bonus room, creating flexible spaces for work, wellness, and recreation. The full walk-out basement, complete with 9-foot ceilings, offers endless possibilities for future finishing and additional living space. The exterior showcases striking Hardie Plank board-and-batten siding, while inside, quality construction and energy efficiency take center stage. Premium building materials, spray foam insulation, recessed lighting throughout, and high-efficiency heat pumps for heating and cooling provide year-round comfort and long-term savings. Step outside to your own private retreat, highlighted by a custom gunite saltwater heated pool surrounded by mature landscaping, hardscape and the tranquility and natural beauty of the property. Whether enjoying quiet mornings overlooking the acreage or hosting gatherings with family and friends, this remarkable setting offers the perfect blend of luxury, privacy, and convenience—just moments from the charming village of Millbrook. A rare opportunity to own a newly crafted estate where exceptional design, modern efficiency, and unparalleled privacy come together in one of the Hudson Valley’s most sought-after locations. Builder is offering generous builder specs and allowances. **PHOTOS ARE RENDERINGS OF A SIMILAR MODEL**

101 N Tower Hill Road, Millbrook

$385,000

Estate property being sold AS, including contents. 5+/-acre parcel of lovely land with meadows, views of rolling hill tops and majestic trees. There is an old growth of grape vines and an orchard with various fruit trees. A truly special piece of property conveniently located to communte to NYC either by car or train. Just the land and improvements alone proof the value of this offering. The winding driveway leads to newly constructed, oversized garage (25'9x26'5) and an existing one bedroom house. The house was built to be energy efficient- a good portion of the living space is built into a hill. There is underground electric to the house, which is 200 amps, as well as a separate 100 amp service in the garage House is in need of significant rehab, or tear down. Could be a great project.

2 Beds ⋅ 1 Baths ⋅ 1006396 MLS

Estate property being sold AS, including contents. 5+/-acre parcel of lovely land with meadows, views of rolling hill tops and majestic trees. There is an old growth of grape vines and an orchard with various fruit trees. A truly special piece of property conveniently located to communte to NYC either by car or train. Just the land and improvements alone proof the value of this offering. The winding driveway leads to newly constructed, oversized garage (25'9x26'5) and an existing one bedroom house. The house was built to be energy efficient- a good portion of the living space is built into a hill. There is underground electric to the house, which is 200 amps, as well as a separate 100 amp service in the garage House is in need of significant rehab, or tear down. Could be a great project.

884 Camby Road, Millbrook

$575,000

Owner listening to all offers. Welcome to this warm and inviting 3-bedroom, 1.5-bath home nestled in the heart of Dutchess County, just minutes from the Village of Millbrook and the Taconic State Parkway. From the moment you step into the entry foyer, you'll feel the character and comfort this home has to offer. The sun-filled living room impresses with a beamed ceiling and wood-burning fireplace — the perfect gathering spot on cool Hudson Valley evenings. The farm-style kitchen flows seamlessly into a charming dining area and sunroom, creating a bright, open space ideal for everyday living and entertaining. A first-floor bedroom and full bathroom offer flexibility for guests, a home office, or single-level living. The expansive bonus room with vaulted ceiling adds generous space for relaxing, with a possible den/office/mother/daughter area, half bath, and laundry area complete the main level. Upstairs, two additional bedrooms provide comfortable private retreats. Step outside to your own backyard oasis — a stunning bluestone patio with fireplace sets the stage for al fresco entertaining, while the privacy-fenced heated saltwater pool with deck, patio, and pool house makes every summer day feel like a vacation. A detached 1-car garage and large driveway round out this exceptional property. All of this in a coveted Millbrook location, close to top equestrian facilities, fine dining, wineries, and everything the Hudson Valley has to offer.

3 Beds ⋅ 2 Baths ⋅ 968366 MLS

Owner listening to all offers. Welcome to this warm and inviting 3-bedroom, 1.5-bath home nestled in the heart of Dutchess County, just minutes from the Village of Millbrook and the Taconic State Parkway. From the moment you step into the entry foyer, you'll feel the character and comfort this home has to offer. The sun-filled living room impresses with a beamed ceiling and wood-burning fireplace — the perfect gathering spot on cool Hudson Valley evenings. The farm-style kitchen flows seamlessly into a charming dining area and sunroom, creating a bright, open space ideal for everyday living and entertaining. A first-floor bedroom and full bathroom offer flexibility for guests, a home office, or single-level living. The expansive bonus room with vaulted ceiling adds generous space for relaxing, with a possible den/office/mother/daughter area, half bath, and laundry area complete the main level. Upstairs, two additional bedrooms provide comfortable private retreats. Step outside to your own backyard oasis — a stunning bluestone patio with fireplace sets the stage for al fresco entertaining, while the privacy-fenced heated saltwater pool with deck, patio, and pool house makes every summer day feel like a vacation. A detached 1-car garage and large driveway round out this exceptional property. All of this in a coveted Millbrook location, close to top equestrian facilities, fine dining, wineries, and everything the Hudson Valley has to offer.

6 Route 343, Millbrook

$749,000

Charming Cape Cod style home with thoughtful updates and wonderful natural light throughout. The first floor features a fully renovated kitchen with a cheerful breakfast bar, a living room with wood-burning fireplace, a sunroom overlooking the lovely backyard, a full bathroom, a bedroom, and an office. Upstairs, you will find another well-proportioned bedroom, a second full bath and a large family room providing a comfortable place for relaxation. The lowest level includes a laundry area and plenty of storage space. Additional highlights include a spacious, sun-drenched deck, a one-car garage, a gardening shed, and a wood storage shed. The beautiful yard creates a wonderful space for entertaining, relaxing, and play. Ideally located within easy walking distance to all the Village of Millbrook amenities. A fantastic opportunity to enjoy comfort, style, and convenience in a small, walkable, vibrant Village. Move in and enjoy all that summer brings including the Millbrook Farmers and Makers Market, local wineries and breweries, rail trails for hiking and biking, equestrian events and County Fairs. The Hudson Valley is a great respite for weekenders and full time residents alike!

3 Beds ⋅ 2 Baths ⋅ 995852 MLS

Charming Cape Cod style home with thoughtful updates and wonderful natural light throughout. The first floor features a fully renovated kitchen with a cheerful breakfast bar, a living room with wood-burning fireplace, a sunroom overlooking the lovely backyard, a full bathroom, a bedroom, and an office. Upstairs, you will find another well-proportioned bedroom, a second full bath and a large family room providing a comfortable place for relaxation. The lowest level includes a laundry area and plenty of storage space. Additional highlights include a spacious, sun-drenched deck, a one-car garage, a gardening shed, and a wood storage shed. The beautiful yard creates a wonderful space for entertaining, relaxing, and play. Ideally located within easy walking distance to all the Village of Millbrook amenities. A fantastic opportunity to enjoy comfort, style, and convenience in a small, walkable, vibrant Village. Move in and enjoy all that summer brings including the Millbrook Farmers and Makers Market, local wineries and breweries, rail trails for hiking and biking, equestrian events and County Fairs. The Hudson Valley is a great respite for weekenders and full time residents alike!

22 Haight Avenue, Millbrook

$1,400,000

This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring ceilings, and striking architectural details that create a unique backdrop for a wide range of uses—whether hospitality, creative ventures, or professional space. Complementing the generous interior, outdoor gardens and landscaped grounds provide space for events or a serene setting for relaxation. Above the main level, a private three-bedroom apartment offers comfortable living with a deck overlooking the surrounding countryside. This rare combination of historic charm, substantial square footage, and adaptable layout makes the property ideal for a live/work arrangement, an investment opportunity, or a visionary redevelopment. With its rich character and flexible design, it presents a truly exceptional opportunity in one of the Hudson Valley’s most desirable locations.

3 Beds ⋅ 8 Baths ⋅ 996782 MLS

This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring ceilings, and striking architectural details that create a unique backdrop for a wide range of uses—whether hospitality, creative ventures, or professional space. Complementing the generous interior, outdoor gardens and landscaped grounds provide space for events or a serene setting for relaxation. Above the main level, a private three-bedroom apartment offers comfortable living with a deck overlooking the surrounding countryside. This rare combination of historic charm, substantial square footage, and adaptable layout makes the property ideal for a live/work arrangement, an investment opportunity, or a visionary redevelopment. With its rich character and flexible design, it presents a truly exceptional opportunity in one of the Hudson Valley’s most desirable locations.

4258 Route 44, Millbrook

$1,495,000

Set along a country road just beyond the Village of Millbrook, this cedar-sided traditional overlooks a serene, spring-fed pond and unfolds across 23 acres of rolling fields, mature trees, and thoughtfully kept grounds. The setting feels both expansive and private, with long views and a true sense of escape. The 3,200+ square foot home offers a spacious and flexible layout, with four bedrooms, three full baths, central air, and a gas fireplace. The main level is centered around an open living and dining area that flows seamlessly to a large deck, perfect for entertaining or simply taking in the landscape. The kitchen is well positioned for everyday ease, while two guest bedrooms share a full bath. The primary suite is tucked away for privacy and opens into a sun-filled sitting room overlooking the pond, a peaceful space for morning coffee or quiet afternoons. The finished lower level expands the living space with a generous family room, a screened porch, and direct access to the attached two-car garage. Outdoors, the property invites exploration, with private walking trails winding through the land and a tucked-away tea house offering a quiet place for reflection. The pond, open fields, and wooded areas create a dynamic and ever-changing backdrop throughout the seasons. Located on a town-maintained gravel road along a historic scenic route, the property offers a rare balance of seclusion and accessibility, minutes to Millbrook’s shops, dining, and amenities, and approximately two hours from NYC by car or train. Additional adjacent acreage may be available for those seeking to expand their footprint.

4 Beds ⋅ 3 Baths ⋅ 994161 MLS

Set along a country road just beyond the Village of Millbrook, this cedar-sided traditional overlooks a serene, spring-fed pond and unfolds across 23 acres of rolling fields, mature trees, and thoughtfully kept grounds. The setting feels both expansive and private, with long views and a true sense of escape. The 3,200+ square foot home offers a spacious and flexible layout, with four bedrooms, three full baths, central air, and a gas fireplace. The main level is centered around an open living and dining area that flows seamlessly to a large deck, perfect for entertaining or simply taking in the landscape. The kitchen is well positioned for everyday ease, while two guest bedrooms share a full bath. The primary suite is tucked away for privacy and opens into a sun-filled sitting room overlooking the pond, a peaceful space for morning coffee or quiet afternoons. The finished lower level expands the living space with a generous family room, a screened porch, and direct access to the attached two-car garage. Outdoors, the property invites exploration, with private walking trails winding through the land and a tucked-away tea house offering a quiet place for reflection. The pond, open fields, and wooded areas create a dynamic and ever-changing backdrop throughout the seasons. Located on a town-maintained gravel road along a historic scenic route, the property offers a rare balance of seclusion and accessibility, minutes to Millbrook’s shops, dining, and amenities, and approximately two hours from NYC by car or train. Additional adjacent acreage may be available for those seeking to expand their footprint.

508 Woodstock Road, Millbrook

$575,000

Welcome to this Contemporary Raised Ranch set on 1.52 acres in the Millbrook area, just minutes to the Village. Offering 2,480 finished square feet, the home has been thoughtfully updated to combine modern finishes with a practical, well-designed layout that flows with ease. The main level features a bright, inviting living area enhanced by a fresh coat of paint throughout, an updated kitchen with newer appliances, and a dining space that works just as well for everyday living as it does for entertaining. The home includes 3 bedrooms and 2.5 bathrooms, including a primary suite with a walk in closet and its own full bath. The finished lower level adds valuable flexibility, with an additional room ideal for an office or den, a half bathroom, family room and a dedicated laundry area. Recent improvements include a brand new well tank and boiler, along with a built-in Vivint security system for added convenience. Set in a location close to local shops, dining, and everyday amenities, and within the Millbrook School District, this move-in ready home presents a great opportunity in a sought-after area.

3 Beds ⋅ 3 Baths ⋅ 973983 MLS

Welcome to this Contemporary Raised Ranch set on 1.52 acres in the Millbrook area, just minutes to the Village. Offering 2,480 finished square feet, the home has been thoughtfully updated to combine modern finishes with a practical, well-designed layout that flows with ease. The main level features a bright, inviting living area enhanced by a fresh coat of paint throughout, an updated kitchen with newer appliances, and a dining space that works just as well for everyday living as it does for entertaining. The home includes 3 bedrooms and 2.5 bathrooms, including a primary suite with a walk in closet and its own full bath. The finished lower level adds valuable flexibility, with an additional room ideal for an office or den, a half bathroom, family room and a dedicated laundry area. Recent improvements include a brand new well tank and boiler, along with a built-in Vivint security system for added convenience. Set in a location close to local shops, dining, and everyday amenities, and within the Millbrook School District, this move-in ready home presents a great opportunity in a sought-after area.

50 Horseshoe Road, Millbrook

$639,000

Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway. Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living. Upstairs includes full, eat in kitchen, dining room, access to deck, living room, three bedrooms and full bath.

4 Beds ⋅ 2 Baths ⋅ 983261 MLS

Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway. Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living. Upstairs includes full, eat in kitchen, dining room, access to deck, living room, three bedrooms and full bath.

3875 Route 82, 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

$850,000

Discover a truly unique Millbrook estate set on over 6 acres with a private pond, fruit trees, and beautiful natural surroundings. This expansive stone and brick residence offers remarkable craftsmanship and imported finishes, including marble and other materials brought in directly from Italy. Designed for both elegance and comfort, the home features multiple kitchens, two formal dining rooms, and seven bathrooms, creating an ideal setting for hosting and entertaining. A spacious three-car garage provides ample parking and storage. Inside and out, the property is filled with thoughtful details and timeless character. Sustainable living is supported by solar panels, while the grounds include assorted fruit trees and other plantings that enhance the serene atmosphere. Whether gathering indoors or enjoying the acreage outdoors, this estate blends practicality, beauty, and old-world charm in a rare Millbrook offering.

4 Beds ⋅ 7 Baths ⋅ 918644 MLS

Discover a truly unique Millbrook estate set on over 6 acres with a private pond, fruit trees, and beautiful natural surroundings. This expansive stone and brick residence offers remarkable craftsmanship and imported finishes, including marble and other materials brought in directly from Italy. Designed for both elegance and comfort, the home features multiple kitchens, two formal dining rooms, and seven bathrooms, creating an ideal setting for hosting and entertaining. A spacious three-car garage provides ample parking and storage. Inside and out, the property is filled with thoughtful details and timeless character. Sustainable living is supported by solar panels, while the grounds include assorted fruit trees and other plantings that enhance the serene atmosphere. Whether gathering indoors or enjoying the acreage outdoors, this estate blends practicality, beauty, and old-world charm in a rare Millbrook offering.

3534 Route 82, Millbrook

$5,500,000

Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined weekend retreat. Designed by an award winning luxury hotelier and designer, every element of this 2022-built home reflects an extraordinary level of vision, craftsmanship, and artistry. Tasteful finishes, custom millwork, and hand-crafted cabinetry enrich the home's generous proportions and stunning open floor plan. An elegant entrance welcomes you into a gracious foyer and a grand living room anchored by a wood-burning fireplace, overlooking sweeping westerly sunset views over the foothills of the Catskills. Slide open the oversized doors to the pool area for seamless indoor-outdoor living at its finest. The chef’s kitchen is a work of art, featuring a four-door Samsung refrigerator, Bertazzoni free-standing vintage range, steam and multi-wall ovens, a microwave, warming drawer, and an integrated hood set against a hand-made Zellige tile backsplash. The adjacent dining area features custom deVOL cabinetry and a full bar, creating a natural separation to a cozy office/den and a fitness room at the rear of the home. The luxurious first-floor primary suite wing enjoys spectacular sunset views and features a fireplace, dual walk-in closets, and a spa-inspired bathroom with inlaid marble floors, a deep freestanding tub, an oversized walk-in shower, and a state-of-the-art Toto toilet. Also on the first floor are a stylish deVOL-designed laundry room, a jewel box powder room, a mudroom, a two-car garage, and additional bonus spaces. Upstairs, three generous ensuite bedrooms, including a second luxurious primary, each feature walk-in closets and perfectly framed vistas. A media room, which doubles as a fifth bedroom, offers even more flexibility, complete with an adjacent full bathroom. The outdoor spaces are nothing short of spectacular, including a built-in outdoor kitchen with a BBQ and gas line hook-up, a bluestone patio, and multiple entertaining and lounging areas framed by French lavender gardens. A separate studio building with a kitchenette and bath provides a home office or an artist’s retreat. Rounding out the estate are a full, dry basement with a temperature-controlled wine room, and a spacious walk-up attic with soaring ceilings, offering ultimate recreation and storage opportunities. Protected by surrounding majestic farmland yet located just moments from the Village of Millbrook, this turn-key modern farmhouse delivers an unparalleled lifestyle of quiet luxury, beauty, and timeless sophistication in the heart of the Hudson Valley.

4 Beds ⋅ 6 Baths ⋅ 854229 MLS

Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined weekend retreat. Designed by an award winning luxury hotelier and designer, every element of this 2022-built home reflects an extraordinary level of vision, craftsmanship, and artistry. Tasteful finishes, custom millwork, and hand-crafted cabinetry enrich the home's generous proportions and stunning open floor plan. An elegant entrance welcomes you into a gracious foyer and a grand living room anchored by a wood-burning fireplace, overlooking sweeping westerly sunset views over the foothills of the Catskills. Slide open the oversized doors to the pool area for seamless indoor-outdoor living at its finest. The chef’s kitchen is a work of art, featuring a four-door Samsung refrigerator, Bertazzoni free-standing vintage range, steam and multi-wall ovens, a microwave, warming drawer, and an integrated hood set against a hand-made Zellige tile backsplash. The adjacent dining area features custom deVOL cabinetry and a full bar, creating a natural separation to a cozy office/den and a fitness room at the rear of the home. The luxurious first-floor primary suite wing enjoys spectacular sunset views and features a fireplace, dual walk-in closets, and a spa-inspired bathroom with inlaid marble floors, a deep freestanding tub, an oversized walk-in shower, and a state-of-the-art Toto toilet. Also on the first floor are a stylish deVOL-designed laundry room, a jewel box powder room, a mudroom, a two-car garage, and additional bonus spaces. Upstairs, three generous ensuite bedrooms, including a second luxurious primary, each feature walk-in closets and perfectly framed vistas. A media room, which doubles as a fifth bedroom, offers even more flexibility, complete with an adjacent full bathroom. The outdoor spaces are nothing short of spectacular, including a built-in outdoor kitchen with a BBQ and gas line hook-up, a bluestone patio, and multiple entertaining and lounging areas framed by French lavender gardens. A separate studio building with a kitchenette and bath provides a home office or an artist’s retreat. Rounding out the estate are a full, dry basement with a temperature-controlled wine room, and a spacious walk-up attic with soaring ceilings, offering ultimate recreation and storage opportunities. Protected by surrounding majestic farmland yet located just moments from the Village of Millbrook, this turn-key modern farmhouse delivers an unparalleled lifestyle of quiet luxury, beauty, and timeless sophistication in the heart of the Hudson Valley.

3585 Route 82, Millbrook