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MLS ID KEY1058072Last updated Oct 22, 2026

Single Family

102 Pleasant Hill Road

Active · New Windsor · Orange County, NY 12553

Bedrooms
5 Beds
Bathrooms
5 Baths
Year built
1833
Est. monthly taxes
$2,094.85
Property gallery0 / 47
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About this home

An 1833 Georgian Colonial, Beautifully Preserved and Fully Reimagined Built in 1833 and set on nearly two acres of terraced, tree-lined grounds, this 4,500-square-foot Georgian colonial is a rare marriage of historic character and flawless modern living. Meticulously maintained and thoughtfully updated, it offers five bedrooms across three levels without sacrificing a single bit of its original charm. Step through the front door and the home opens in one sweeping line of sight, straight through to sliding doors and the bluestone patio beyond. Original hardwood floors run throughout most of the home, grounding every room in its history. At the heart of the home, the sunlit eat-in kitchen is a true chef’s space, featuring an 8-burner Wolf range, 48" Sub-Zero refrigerator, double oven, oversized island, silestone countertops, and a dedicated beverage station. It flows seamlessly into the formal dining room, where a fireplace sets an elegant tone, and into the living room with its handsome built-ins. A first-floor office with a private entrance, fireplace, and full bath is ideal for working from home or hosting guests in total privacy. Finishing off the first floor is the laundry area and a powder room. Upstairs, the second floor offers three bedrooms and two full baths, featuring generous closets and abundant storage. The primary suite includes an ensuite bath and updated closets. The third bedroom has its own fireplace and direct access to the hall bathroom. The recently renovated third floor adds two more bedrooms and a newly updated bath, with additional closet and storage space. The grounds are as memorable as the house. Perennial gardens, specimen trees, and natural stone walls define the property, all enclosed by a stockade fence for privacy. The lawn was terraced in the 1940s to host a wedding reception, and those graceful tiers remain today, creating distinct outdoor rooms for entertaining. In the back corner, a heated saltwater in-ground pool completes the setting. Practical luxuries abound: a three-car garage (two bays heated and currently used as a home gym), a full basement with a workbench and new Bilco doors, a whole-house generator, 200-amp electric service, a 300-foot well with a water softener, a Vermont slate roof, and a boiler just ten years old. Easy access to commuter train to the city, located in the Cornwall School District. A one-of-a-kind offering that delivers history, privacy, and every modern comfort. A must-see!

Listing snapshot

Days on site
17 days
Listed on MLS
Oct 22, 2026
Full baths
4
Half baths
1
Annual property tax (MLS)
$25,138.25
Tax year
2026
Area source (MLS)
Public Records
Listing brokerage
Howard Hanna Rand Realty
MLS ID
KEY1058072
Last updated
Oct 22, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1833
Garage
Yes
Garage spaces
3
Total parking
8
Parking
Driveway, Garage, Garage Door Opener, Heated Garage
Water source
Well
Sewer
Septic Tank
Utilities
Electricity Connected, Propane, Trash Collection Private

Interior features

Basement
Bilco Door(s), Full
Heating
Oil
Cooling
Wall/Window Unit(s)
Interior
First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Breakfast Bar, Built-in Features, Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Ceilings, Kitchen Island, Original Details, Primary Bathroom, Storage, Washer/Dryer Hookup
Appliances
Dishwasher, Gas Cooktop, Gas Oven, Microwave, Stainless Steel Appliance(s), Washer, Water Softener Owned
Flooring
Hardwood, Other
Fireplace
Yes
Fireplaces
4

Exterior features

Architectural style
Colonial
Construction materials
Stone
Exterior
Garden, Mailbox, Rain Gutters
Private pool
Yes

Schools (MLS)

Elementary school
Cornwall Elementary School
Elementary school district
Cornwall
Middle school
Cornwall Middle School
Middle school district
Cornwall
High school
Cornwall Central High School
High school district
Cornwall

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. MLS status changed
  3. First seen on this site

Location

New Windsor · Orange County, NY 12553Show interactive map
102 Pleasant Hill Road

New Windsor · Orange County, NY 12553

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
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Monthly property taxNot provided

Monthly association / maintenance feesNot provided

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Listing data is supplied by the MLS and may change without notice.