About Property

Discover the ultimate upstate escape at Twin Pond Ridge, a luxurious Dutchess County estate in Dover Plains, New York, situated just two hours from NYC. This stunning retreat is perched on a hillside, offering long, sweeping views of the Hudson Valley and the serene privacy of a classic Northeast lodge design featuring cedar shake siding, exposed timber beams, and rich wood accents.

Designed for gatherings and relaxation, the estate features 5 bedrooms, 5 beds, and 4 bathrooms, comfortably accommodating up to 8 guests. The main level hosts a primary suite with a king-size bed, mountain views, a walk-in closet, and a private ensuite bathroom. Two additional bedrooms—one with a queen bed and another with two twin beds—share a convenient bathroom. The second floor provides flexible sleeping arrangements with a queen bedroom and a room featuring two sets of built-in bunk beds, ideal for children, which share a third bathroom.

The home's interior is a masterclass in lodge style, boasting wide-plank dark flooring and a striking floor-to-ceiling stone fireplace in the living area. The kitchen is equipped with black stone countertops, shaker-style cabinetry, and a breakfast bar, while the adjacent dining room overlooks a tranquil pond. For entertainment, guests can enjoy a formal game room and bar with a pool table and stone fireplace, or slip through elegant wainscoting into a hidden movie theater equipped with a projector and comfortable sectional seating. The basement adds further versatility with an office space and a recreation area featuring a rowing machine, foosball, and air hockey.

Step outside to a stunning oasis featuring an in-ground pool framed by a generous stone patio, as well as a tennis/basketball court and a relaxing hammock.

Located in a prime position for exploring the region, the estate is minutes from Millbrook, Amenia, and Millerton. Guests can enjoy local gems like Wethersfield Garden, Babette’s Kitchen, or the Millbrook Farmers Market.

Practical Information:

• Check-in: 4:00 PM
• Check-out: 11:00 AM
• Pets: Not permitted
• Smoking: Not permitted inside (subject to a $500 fee)
• Primary guest must be 25+ years old
• Note: The pool is not heated and operates seasonally from Memorial Day to Labor Day
• A 4WD vehicle is strongly recommended for winter travel due to local road conditions
• Please adhere to septic rules: only toilet paper may be flushed
• Excessive cleaning fees of $500 may apply for incidents beyond standard turnover

Twin Pond Ridge is the perfect destination for family gatherings or a peaceful weekend retreat, blending natural beauty with sophisticated comfort.

This description is for informational purposes. Please verify all details, including amenities, policies, fees, and availability, on the booking platform before booking.