20 Orchard Hill Dr

Millbrook NY 12545

5486 sq. ft.

549727 sq. ft.

Single-Family

Last sold for $2,650,000

Kathyrn Johnson, last sold this property on 24 April 2026 after 813 days on market.

Overview

Modern Country Retreat with Iconic Hudson Valley Views Proven Investment or Private Escape Seconds from Millbrook Experience refined country life in this beautifully updated Hudson Valley home, nestled on 12+ private acres with sweeping views of the Catskill Mountains. Surrounded by lush lawns, open meadows and a fenced paddock, the property offers a sense of serenity, space, and elevated living— Designed with both comfort and style in mind, the main floor welcomes you with a sun-filled foyer and elegant curved staircase. A spacious living room with a wood-burning fireplace, formal dining room, and expansive deck set the stage for effortless entertaining. The chef’s kitchen is a true focal point—featuring a second fireplace, pantry, and French doors that lead to an additional private deck for morning coffee or evening cocktails surrounded by nature. Upstairs, the second-floor primary suite offers a peaceful escape, complemented by two additional bedrooms and a guest suite. The third floor includes a flexible bonus room with full bath—perfect for a home office, gym, or studio. The lower level features two additional bedrooms, a rec room, and walkout access—ideal for guests or multi-generational living. Ideal for animal lovers too, the property features 2 paddocks and 3 run in sheds equipped with water and electricity, perfect for summer turnout! A heated gunite pool with Bluestone terrace offers a resort-like feel, while the surrounding landscape creates an ever-changing backdrop of color and light throughout the seasons. Meticulously renovated this home features a new roof, HVAC, and all updated mechanicals, offering a seamless move-in-ready experience. With a proven short-term rental history and impressive revenue, this home also presents an exceptional investment opportunity. Its strong rental income make it ideal for those looking to offset ownership costs or build long term value. The location, only 90 minutes to NYC and just a few minutes to the Village of Millbrook, makes for the perfect balance of privacy and accessibility. In a region celebrated for its beauty, lifestyle appeal and climate resilience, this is a home that offers not only luxury-- but lasting value.

Features

7 bedrooms

7 bathrooms

3 carspaces

3 garage spaces

5486 sq. ft. floor area

549727 sq. ft. lot size

Single-Family

Estimated Value

We need at least 3 similar 7 bedroom single-family properties sold in Millbrook over the last 12 months.

Property history for 20 Orchard Hill Dr

2026

Sold

$2,650,000

24 Apr 2026 by Kathyrn Johnson, of William Pitt Sothebys Int Rlty

2016

Sold

$785,000

05 Aug 2016 by Neil Charles, of Neil Charles Real Estate, LLC

Happy sellers in Millbrook

We have insufficient information to provide an overview of customer satisfaction for Millbrook. Viewing the agent profiles, reviews and sales for Millbrook can provide insights for this location.