Twin Pond Ridge - Pool, Views, Games

Enjoy a luxe retreat with a formal game room and bar, secret movie theater, pool, tennis court, and gym. This classic lodge style home features a private setting, pond, and 2 stone fireplaces, along with comfortable guest rooms and plenty of room for your group to gather. This home has everything you need for a peaceful getaway.

Nearby towns: Millbrook (10mins), Amenia (15mins), Millerton (25mins), Sharon, CT (20 mins) Pawling (25mins)

Twin Pond Ridge is a luxurious Dutchess County estate, set on a hillside with long views of the Hudson Valley. The home is defined by classic Northeast lodge design, with cedar shake siding,
exposed timber beams, rich wood accents, and wide-plank dark flooring. This home features a pool, tennis courts, formal game room and movie theater, and plenty of space for your group to gather and enjoy an upstate getaway.

At the top of the long, private drive, enter through the mudroom which leads to the kitchen and dining room beyond. The kitchen features classic shaker-style cabinetry, black stone countertops and a breakfast bar, along with a welcoming dining room framed by windows overlooking the pond. The living area offers a striking floor-to-ceiling stone fireplace, and french doors on either side, opening to a stone patio on the front of the home, and a grill and lounge area in the back.

Beyond the spacious living room, find two additional bedrooms, one with two twin beds and the other with a queen, sharing a bathroom with a tub/shower combo. The primary bedroom is also on this level, where a king-size bed and mountain views create a serene retreat. This suite includes a walk-in closet, private access to the outdoors, and an ensuite bathroom with a walk-in shower. Another bathroom with a tub/shower combo is located on this level between the office and the stairs to the second floor for added convenience.

Upstairs, two more guest bedrooms offer flexible sleeping arrangements: one with two sets of built-in bunk beds ideal for kids, and the other with a queen bed. These rooms share a bathroom with a walk-in shower.

This level also features the formal game room and bar with a pool table, window seat overlooking beautiful views, a stone fireplace and TV. Push through the elegant wainscoting to reveal a hidden theater room with projector and comfortable sectional couch and beanbag chairs.

The basement provides an additional multipurpose space. Work from home from the office space, unwind on the sectional, play a round of foosball or air hockey, or fit in a workout on the rowing machine.

Outdoors, the in-ground pool presents a stunning oasis framed by a generous stone patio with comfortable loungers and an oversized umbrella surrounded by lush greenery. Wander the grounds to discover a tennis/basketball court, a tranquil pond, and a hammock.

Twin Pond Ridge is ideal for summer stays, family gatherings, or peaceful weekend retreats offering privacy, comfort, and natural beauty just steps from your door.

Staying at Twin Pond Ridge means experiencing some of Hudson Valley’s best spots just minutes away.

Start your morning with a flaky croissant from Babette’s Kitchen or a perfectly brewed coffee at All That Java. Spend a peaceful afternoon wandering the stunning landscapes at Wethersfield Garden, widely regarded as one of the finest classical gardens in the country.

For a taste of local life, browse seasonal produce and artisanal goods at the Millbrook Farmers Market. Book lovers shouldn’t miss Merritt Bookstore, while treasure hunters can spend hours exploring the Millbrook Antique Mall.

Looking for something unique? Try clay target shooting at Orvis Sandanona, the oldest registered shooting preserve in the country. In the evening, unwind with a glass at Mill Wine, then settle in for dinner at Barbaro, Les Baux, or Charlotte’s.

Twin Pond Ridge is just 2 hours from New York City. A car is essential for getting there and exploring the area. The main access routes are the Taconic State Pkway, Sprain Brook Pkway S and I-87 S. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.

Please note that the pool closes every year seasonally, just around Labor Day, and reopens typically around Memorial Day.

** The pool is not heated. **