Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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4
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Bathrooms
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4
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House Rules
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-
Pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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8
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Property Id
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3390017
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Summary:
Whimsy Woods, where contemporary design meets country escape, is a private getaway just minutes from the village of Millbrook. Approaching the property, you’ll feel the rich equestrian history of this historic hamlet, with paddocks and stables, sprawling meadows, and lush lawns. Through the wooden gate, find this uber-private 14-acre estate. The landscape features a mixture of manicured lawns and mature woodlands with walking trails.
The Space:
MAIN HOUSE:
Enter to a light-filled foyer with vaulted ceilings and a stunning chandelier. The glass-paneled stairway and open spaces invite you to explore. A minimalist office with built-in bookcases flows into a formal living room centered around a wood-burning fireplace. Fling open the French doors and invite the breeze while enjoying cocktail hour, or your morning paper.
The opposite side of the main floor is occupied by the kitchen and dining room, with ample seating. The space is open, allowing guests to mingle and pitch in, while you take advantage of the chef’s appliances and generous counter space to conjure a memorable meal. When the weather is right, the patio accessed by French doors off the back is another lovely dining location, with an additional 10-seat dining table under a wisteria-covered pergola and chain of fairy lights.
The main house hosts three bedrooms on the second floor. The primary suite spans one-half of the floor, vaulted ceilings rising to the peak of the roof, separating the bedroom from the expansive primary bath. Light streams through, with a row of glass panels dividing the bed and bath, and windows across both sides of the home. The en-suite bathroom has dual sinks, a walk-in shower, and a lovely soaking tub overlooking the grounds. On the other side of the floor are two guest bedrooms, one with a queen-sized bed, and the other with a pair of single beds and its own dedicated workspace. They share a connected full bathroom between them with a tub/shower.
The basement is a great place to send the kids, or relax for a low-key movie or game night. The media room with built-in bookshelves has a smart TV, comfy couches, a pull out sofa, and a game table. Rounding out the myriad amenities of this home is a home gym with a Peloton bike, treadmill, and assortments of weights and equipment.
GUEST HOUSE:
When you have a full house, take advantage of the guest suite for two above the garage. The open concept suite is divided by a half wall and features a queen bed overlooking the pool, and its own kitchenette. With a sitting area, bistro table and full bath with a walk-in shower this additional space completes Whimsy Wood’s capacity for 8 guests to stay in comfort and style.
Truly, the outdoor spaces set this home apart. The natural cathedral of mature trees surrounding the property gives a sense of total privacy. Wander the trails cut through the woods, and take the kayak out to birdwatch at either of two ponds on the property. The gunite pool surrounded by bluestone patio is an irresistible summer escape. Lounge the day away into the night — the pool is heated — and the propane fire pit will take the edge off an evening chill.
If you can muster the willpower to leave this idyllic property, the town of Millbrook, in the heart of the Hudson Valley, is equally positioned between iconic towns like Rhinebeck and Millerton (both under 30 minutes), and western Litchfield County towns.
Guest Access:
Guests have unrestricted access to the whole property and can enjoy the privacy Whimsy Woods has to offer.
The Neighborhood:
Whimsy Woods is located only 5 minutes away from the Village of Millbrook on one of the town’s most scenic settings, Woodstock Road.
Truly, the outdoor spaces set this home apart. The natural cathedral of mature trees surrounding the property gives a sense of total privacy. Wander the trails cut through the woods, and take the kayak out to birdwatch at either of two ponds on the property. The saline gunite pool surrounded by bluestone patio is an irresistible summer escape. Lounge the day away into the night — the pool is heated — and the propane fire pit will take the edge off an evening chill. A functioning animal farm offering fresh products for purchase as well as a horseback riding school set on beautiful grounds are neighboring the property.
If you can muster the willpower to leave this idyllic property, the town of Millbrook, in the heart of the Hudson Valley, is equally positioned between iconic towns like Rhinebeck and Millerton (both under 30 minutes), and western Litchfield County towns.
Getting Around:
The property is set behind a long winding driveway. Ample parking on property. Guests can easily visit the Village of Millbrook via car or bicycle.
Other Things to Note:
* Please note the pool opens from mid-to-late May until mid-to-late September. Please inquire regarding specific opening and closing dates.
* The pool is heated up to 75 degrees, complimentary. If you desire additional heating, there is a fee, please inquire for more information. There is a minimum of 2 nights charge for pool heating and the cost ranges from $200-$300 total for pool heating.
*One well-behaved dog is welcome at the property (with an additional pet fee). Sorry, cats are not permitted.
Interaction with Guests:
Host will be at guests’ disposal throughout the stay. The guests’ will be supported by local staff to ensure a seamless stay.
Millbrook is home to this vacation home. Millbrook Vineyards and Winery and Clinton Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Buttercup Farm Audubon Sanctuary and James Baird State Park. Innisfree Garden and Trevor Zoo are also worth visiting.
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