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20 Orchard Hill Drive, Millbrook, NY 12545

$2,875,000
Property Type: Residential Bedrooms: 6 Baths: 7 Square Footage: 5,486 Lot Size (sq. ft.): 549,727 Status: Active
Current Price: $2,875,000 List Date: 2/21/2026 Last Modified: 2/28/2026

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.

More Information MLS# 20260696

Contract Information

Listing Agreement: Exclusive Right To Sell Owner Name: Orchard Hill Holdings LLC Occupant Type: Owner Lease Considered YN: No Current Price: $2,875,000 Original List Price: 2875000 List Price: $2,875,000 Status: Active Listing Contract Date: 2026-02-20 Property Sub Type: Single Family Residence

Location, Tax, and Legal

911 Address: Millbrook NY Township: Washington School District: Millbrook Central School District General Tax: 7067 School Tax: 19548 Tax Annual Amount: 24025 Assessors Full Market Value: 1651200 Tax Assessed Value: 812800 Tax Legal Description: Sf residential Parcel Number: 135889-6765-331674 Tax Lot: 331 Tax Block: 6765 Tax Exemptions YN: No Zoning: RM3 Directions: GPS - 20 Orchard Hill Rd.

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: 524.06 Bedrooms Total: 6 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: 2026-02-21 Major Change Timestamp: 2026-02-21T19:46:19Z Major Change Type: New Listing

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
Information deemed reliable but not guaranteed.