20 Orchard Hill Drive, Millbrook, NY 12545 (MLS# 20254297)
$2,850,000
Millbrook, NY 12545
MLS# 20254297
Status: Pending
7 beds | 7 baths | 5486 sqft

1 / 42
Property Description
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 very spacious area with full bath and walk in closet. The lower level features two additional bedrooms, a recreational 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 expenses 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.
Details
Contract Information
Listing Agreement: Exclusive Right To Sell
Owner Name: Orchard Hill Holdings LLC
Occupant Type: Owner
Lease Considered YN: No
Current Price: $2,850,000
Original List Price: 2700000
List Price: $2,850,000
Status: Pending
Listing Contract Date: 2025-09-11
Property Sub Type: Single Family Residence
Location, Tax, and Legal
911 Address: Millbrook NY
School District: Millbrook Central School District
General Tax: 7067
School Tax: 19548
Tax Annual Amount: 26616
Assessors Full Market Value: 1651200
Tax Assessed Value: 1227848
Tax Legal Description: 12.62 AC
Parcel Number: 13588900676500003316740000
Tax Lot: 331
Tax Block: 6765
Tax Exemptions YN: No
Zoning: RM3
Directions: Left from Valley Fam
General Property Information
Bathrooms Half: 1
Above Grade Finished Area: 5486
Below Grade Finished Area: 0
Lot Size Acres: 12.62
New Construction YN: No
Garage YN: Yes
Attached Garage YN: Yes
Garage Spaces: 3
Sign On Property YN: No
Basement YN: Yes
List Price/SqFt: 519.5
Bedrooms Total: 7
Bathrooms Total: 7
Bathrooms Full: 6
Living Area: 5486
Year Built: 1993
Remarks and Miscellaneous
Public Remarks: 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 very spacious area with full bath and walk in closet. The lower level features two additional bedrooms, a recreational 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 expenses 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.
Status Change Information
Status Change Timestamp: 2026-01-23
Major Change Timestamp: 2026-01-24T03:23:51Z
Major Change Type: Status Change
Price Change Timestamp: 2025-10-02T22:06:36Z
Purchase Contract Date: 2026-01-23
Appliances
Built-In Gas Oven: 1
Dishwasher: 1
Dryer: 1
Electric Water Heater: 1
Exhaust Fan: 1
Freezer: 1
Gas Oven: 1
Ice Maker: 1
Microwave: 1
Oven: 1
Range Hood: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Vented Exhaust Fan: 1
Washer: 1
Washer/Dryer: 1
Architectural Style
Traditional: 1
Basement
Full: 1
Book Information
Liber/Book: 331
Page: 765
Section: 6
Cooling
Central Air: 1
Pool Features
Gunite: 1
In Ground: 1
Pool Cover: 1
View
Mountain(s): 1
Pasture: 1
Location Tax and Legal
Street Number: 20
Street Name: Orchard Hill
Street Suffix: Drive
County: Dutchess
State: NY
Zip Code: 12545
Town (Taxable): Millbrook
Property Features
Appliances: Built-In Gas Oven; Dishwasher; Dryer; Electric Water Heater; Exhaust Fan; Freezer; Gas Oven; Ice Maker; Microwave; Oven; Range Hood; Refrigerator; Stainless Steel Appliance(s); Vented Exhaust Fan; Washer; Washer/Dryer
Architectural Style: Traditional
Basement: Full
Cooling: Central Air
Pool Features: Gunite; In Ground; Pool Cover
View: Mountain(s); Pasture
Listing Courtesy of William Pitt Sotheby's Interna
Listing Agent: Kathryn Johnson