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$785,000

Rich in history and character this 1820 farmhouse offers 5 bedrooms and three and a half baths a total of 4616 finished square feet in the main residence. Gorgeous wide plank floors, many windows, 2 staircases, tucked away rooms add to the charm and coziness of this home. Throughout the house the historic details add to the welcoming feeling, however thoughtful renovations including all the bathrooms and the attentive and continual maintenance including the addition of insulation in the walk-up attic and the basement the 10,000-watt whole house generator create a sense of modern comfort. A private and versatile east wing can be closed off from the house creating an ideal guest suite complete with a living/family room, bedroom and full bath. This area has three skylights, a propane stove, private entrance and a door to the private deck and back yard. In addition to the main home there is a self-contained 2 bedroom, 1. 5 bath apartment. This space can be accessed through an enclosed hallway from the house and also through an independent door. Originally finished in 1994 this 1000 finished square feet apartment has been recently renovated with radiant heat, new boiler in 2024, a washer/ dryer and the metal roof was repainted in 2025. The countertops are new and tile was installed in the full bath. This is a great space for, extended family, guests, a nanny or as an income producing opportunity. Outside the impressive three bay barn is a destination in itself. Equipped with electricity, water and a second floor it offers endless possibilities for hobbyists, artists, or storage. As a delightful conversation piece, the barn’s striking oversized front windows was salvaged from the legendary James Cagney Stage Stop Restaurant, adding another unique chapter to this remarkable property’s story. The 1.11-acre property is a lovey combination of open, mostly level yard, trees and gardens enhanced by private decks to the back and side of the property. Surrounded by the beauty of the Hudson Valley and tucked just beyond farmland, it is conveniently located with easy access to the Taconic Parkway and effortless travel just a short distance from the regions many farm markets, wineries, cultural attractions and charming villages.

5 Beds ⋅ 4 Baths ⋅ 1025832 MLS

Rich in history and character this 1820 farmhouse offers 5 bedrooms and three and a half baths a total of 4616 finished square feet in the main residence. Gorgeous wide plank floors, many windows, 2 staircases, tucked away rooms add to the charm and coziness of this home. Throughout the house the historic details add to the welcoming feeling, however thoughtful renovations including all the bathrooms and the attentive and continual maintenance including the addition of insulation in the walk-up attic and the basement the 10,000-watt whole house generator create a sense of modern comfort. A private and versatile east wing can be closed off from the house creating an ideal guest suite complete with a living/family room, bedroom and full bath. This area has three skylights, a propane stove, private entrance and a door to the private deck and back yard. In addition to the main home there is a self-contained 2 bedroom, 1. 5 bath apartment. This space can be accessed through an enclosed hallway from the house and also through an independent door. Originally finished in 1994 this 1000 finished square feet apartment has been recently renovated with radiant heat, new boiler in 2024, a washer/ dryer and the metal roof was repainted in 2025. The countertops are new and tile was installed in the full bath. This is a great space for, extended family, guests, a nanny or as an income producing opportunity. Outside the impressive three bay barn is a destination in itself. Equipped with electricity, water and a second floor it offers endless possibilities for hobbyists, artists, or storage. As a delightful conversation piece, the barn’s striking oversized front windows was salvaged from the legendary James Cagney Stage Stop Restaurant, adding another unique chapter to this remarkable property’s story. The 1.11-acre property is a lovey combination of open, mostly level yard, trees and gardens enhanced by private decks to the back and side of the property. Surrounded by the beauty of the Hudson Valley and tucked just beyond farmland, it is conveniently located with easy access to the Taconic Parkway and effortless travel just a short distance from the regions many farm markets, wineries, cultural attractions and charming villages.

2327 Salt Point Turnpike, Clinton Corners

$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

$720,000

This cozy shingle style cottage is set on top of a daffodil freckled hill in the middle of the Millbrook hunt country. It has been remodeled giving it a more modern feel, increased light and views of hills, valley and farms. All the windows on the first floor have been replaced as has the roof, furnace, water heater and UV system. The terrace has been re-pointed and and an enclosed garden with raised beds and a multitude of fruit trees have been added. One can enter through a generous mud room and then into an open plan including the living and dining area anchored by a stone wood burning fireplace. There are two bedrooms and two full baths on the first floor and two bonus rooms with full bath downstairs that could be used for offices, work out room, media room etc. Also downstairs is a full laundry room with sink and an immaculate mechanical room with ample storage. A generator is included. Centrally located to local farms stands and the towns Millbrook, Amenia, North East and Stanfordville for shopping and dining. The train is but 13 miles a way making a commute possible.

2 Beds ⋅ 3 Baths ⋅ 1001713 MLS

This cozy shingle style cottage is set on top of a daffodil freckled hill in the middle of the Millbrook hunt country. It has been remodeled giving it a more modern feel, increased light and views of hills, valley and farms. All the windows on the first floor have been replaced as has the roof, furnace, water heater and UV system. The terrace has been re-pointed and and an enclosed garden with raised beds and a multitude of fruit trees have been added. One can enter through a generous mud room and then into an open plan including the living and dining area anchored by a stone wood burning fireplace. There are two bedrooms and two full baths on the first floor and two bonus rooms with full bath downstairs that could be used for offices, work out room, media room etc. Also downstairs is a full laundry room with sink and an immaculate mechanical room with ample storage. A generator is included. Centrally located to local farms stands and the towns Millbrook, Amenia, North East and Stanfordville for shopping and dining. The train is but 13 miles a way making a commute possible.

3881 ROUTE 44, 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

$1,250,000

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

$65,000,000

The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer retreat from New York City, 1 ½ hours’ drive away, Millbrook has long been a destination for peaceful weekends and summer escapes. This vast estate has been in the hands of a single owner for the past 60 years with only 2 owners in between the first and last. It is rare and valuable and offers many different uses. It has been maintained and cared for through the years. For now it is farmed self-sufficiently with extensive hay fields providing hay for the cattle farm. The stone farm buildings, updated over the years, are the same ones built and used by the first owner from over a century ago. The 2078 acres of prime land is in a prime location, wooded and open with 2 large lakes (45 and 60 acres) and other ponds. The rectangular shape of the land has frontage on 4 roads. There are 2 major main houses. The restored main Mansion, on its own deed, is 14,706 sq ft designed by James E. Ware in the late 1800’s and the guest house, called the Bungalow, is 10,000 sq ft, was designed by Addison Mizner in 1912. There is a stone Bowling Alley and a fanciful Gate House both built in Bavarian style, a 3 bedroom Cottage, a Carriage house with 2 apartments. 2 Farmhouses, Barns and former Tennis pavilion. Altogether a complete and desirable many faceted domain. Additional Information: HeatingFuel:Oil Above Ground,

10 Beds ⋅ 8 Baths ⋅ H6314256 MLS

The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer retreat from New York City, 1 ½ hours’ drive away, Millbrook has long been a destination for peaceful weekends and summer escapes. This vast estate has been in the hands of a single owner for the past 60 years with only 2 owners in between the first and last. It is rare and valuable and offers many different uses. It has been maintained and cared for through the years. For now it is farmed self-sufficiently with extensive hay fields providing hay for the cattle farm. The stone farm buildings, updated over the years, are the same ones built and used by the first owner from over a century ago. The 2078 acres of prime land is in a prime location, wooded and open with 2 large lakes (45 and 60 acres) and other ponds. The rectangular shape of the land has frontage on 4 roads. There are 2 major main houses. The restored main Mansion, on its own deed, is 14,706 sq ft designed by James E. Ware in the late 1800’s and the guest house, called the Bungalow, is 10,000 sq ft, was designed by Addison Mizner in 1912. There is a stone Bowling Alley and a fanciful Gate House both built in Bavarian style, a 3 bedroom Cottage, a Carriage house with 2 apartments. 2 Farmhouses, Barns and former Tennis pavilion. Altogether a complete and desirable many faceted domain. Additional Information: HeatingFuel:Oil Above Ground,

45 Hitchcock Lane, Millbrook