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
0 of 47 photos ready
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
- Listing updated from MLS
- MLS status changed
- First seen on this site
Location
Estimate monthly payment
Estimated monthly principal & interest—
Monthly property taxNot provided
Monthly association / maintenance feesNot provided
Estimated monthly total of entered costs—
Listing data is supplied by the MLS and may change without notice.
