Photos by Tim Lee, courtesy of Houlihan Lawrence

An 85-acre estate with one of the best equestrian facilities in Dutchess County is on the market for $3.95 million. Not only is the property at 23 Altamont Road in Millbrook a haven for horse lovers, but part of it also once belonged to late actress Mary Tyler Moore. Now known as Grace Hill Farm, the estate includes a barn with an indoor heated arena, a 14-stall stable, a viewing lounge, an outdoor jumping area and field, as well as a four-bedroom farmhouse.

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All photos courtesy of Compass

It’s hard to believe this stunning home is asking under $1 million, but it’s even more surprising that it’s available for the first time in over a century. Located in the Dutchess County hamlet of New Hamburg, the Victorian home was built in 1860 and underwent a full restoration in 2003. In addition to its great location, wrap-around porch, and tons of preserved historic details, the property comes with a separate guest cottage that’s just as lovely.

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All listing photos courtesy of Houlihan Lawrence

Two hours north of the city in the Dutchess County town of Wassaic, you can own an entire 125-acre farm for the price of a three-bedroom Manhattan condo. Known as Avalon Farm, the $2,950,000 property has a nearly 3,000-square-foot contemporary main house, along with a fully functional barn, an in-ground pool and adjacent log cabin pool house, tennis court, and its own stream. It’s definitely secluded, but the farm is a quick drive to downtown Amenia, which is full of restaurants, antique shops, and even a drive-in movie theater.

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While many vacation homes are the result of an elaborate design process and lengthy construction, this house located in rural New York was designed and then built using prefabricated elements in just a couple of days. The U.S. firm Desai Chia Architecture is responsible for the single-story rectilinear space, also known as LM Guest House. The 2,000-square-foot prefab oasis is located in Dutchess County (about two hours north of Manhattan) and situated on a rocky outcrop of land that overlooks a trout pond and farm.
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If you owned this Dutchess County home, you’d never need to stay in a cute country inn; the historic Hyde Park/Pleasant Valley four-bedroom house resembles a quaint B&B from its outbuildings and pond to its cozy interiors (h/t CIRCA). Currently on the market for $525,000, 45 Marshall Road is about the most textbook example of an uncomplicated country home that we’ve seen in a while. And it might be just the thing for next year’s Christmas card photo.

Explore the simple life

Have you spent the summer dreaming about where you want to escape to in upstate New York? This listing won’t make you feel any better. Called the Mission House, it is a beautiful modern mansion located in East Fishkill, a charming town on the southern border of Dutchess County, New York. The house itself is gorgeous, with stunning landscaping, modern design, and tons of space. Get this: the house covers 4,000 square feet, with an additional 2,400 square feet of decks. Of course, it isn’t cheap, but you’ll still get more bang for your buck up here than down in Manhattan—for the whole mansion, the asking price is $1.4 million, cheaper than many NYC apartments. (And keep reading for a way to stay here without forking over all that cash.)

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Located in Tivoli, a village in Dutchess County, this charming rustic barn has everything you would want in a home: There are cozy wooden interiors, it’s surrounded by gardens, it has its own pond, there’s small yoga deck right next to a stream, and there’s even a cozy deck at the back. While you may think a home like this will forever be out of your reach, think again. This beauty is up for rent, and it’s just two hours north of the city.

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With fall inching closer, thoughts of sitting fireside with a cup of tea have started to fill our heads. And while the city is a splendid place in the autumn, nothing beats taking in the country air and the crunch of leaves beneath ones feet.

Now up for auction is this perfect fall escape (or full time home)—an incredible property located in the town of Amenia in Dutchess County. The sprawling 17-acre property, a.k.a. Meri-Mac Farm, comes with four bedrooms, 8,500-square-foot farmhouse, a three-stall stable, a horse pasture, pool, poolhouse and a separate guest house with two-bedrooms. Another fun bonus? You can claim one degree of Kevin Bacon—and Meryl Streep—who live nearby.

Explore the beautiful country home and farm