102 Pleasant Hill Road, New Windsor, NY 12553

$1,050,000
  • 102 Pleasant Hill Road, New Windsor, NY 12553 Main Photo

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BEDS5 BATHS4 full 1 partial SQUARE FEET4,499 MLS#1058072
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLCornwall

Property Description

An 1833 Georgian Colonial, Beautifully Preserved and Fully ReimaginedBuilt 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!

102 Pleasant Hill Road | MLS# 1058072

This single family home located at 102 Pleasant Hill Road, New Windsor, NY 12553 is currently listed for sale with an asking price of $1,050,000. This property was built in 1833 and has 5 bedrooms and 4 full and 1 partial baths with 4499 sq. ft. Pleasant Hill Road is located within the Cornwall school district. Search New Windsor real estate on ryanduhaney.century21americanhomes.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Bilco Door(s), Full
Cooling: Wall/Window Unit(s)
Fenced: Yes
Fireplaces: 4
Garage: 3
Heating: Oil
Home Style: Colonial
Lot Size: 1.90 Acres
Taxes: $25,138
Year Built: 1833

Amenities

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
Garden
Mailbox
Rain Gutters

Feature Descriptions

Appliances: Dishwasher, Gas Cooktop, Gas Oven, Microwave, Stainless Steel Appliance(s), Washer, Water Softener Owned
Attic: Dormer
Days on Site: 12
Exclusions: Dining room chandelier, gym equipment
Exterior: Stone
Fencing: Back Yard, Fenced, Wood
Fireplace Features: Bedroom, Decorative, Wood Burning
Fireplace Y/N: Yes
Flooring: Hardwood, Other
Formal Dining: Yes
GarageY/N: Yes
Lot Features: Back Yard, Garden, Landscaped, Secluded
Number Of Kitchens: 1
On Market Date: 2026-10-22
Parcel Number: 332489-030-000-0001-068.000-0000
Parking Features: Driveway, Garage, Garage Door Opener, Heated Garage
Parking Total: 8
Patio And Porch: Patio
Pool Features: In Ground, Salt Water
Rental Term: Monthly
Rooms Total: 9
Sewer: Septic Tank
Special View Info: Mountain(s)
Swimming Pool: Yes
Utilities: Electricity Connected, Propane, Trash Collection Private
Water: Well

Local Schools

High School: Cornwall Central High School
Middle School: Cornwall Middle School
Elementary School: Cornwall Elementary School
School District: Cornwall

Estimate Your Payment

Estimated Payment

$ 4,737.93 per month $2,336.84 Principal & Interest $2,094.83 Property Tax $306.25 Homeowner's Insurance

Change Payment Information

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(Payments are an estimate and may vary by lender)

Listed By / Shown By

Listing By

Agency Name: Howard Hanna Rand Realty
Agency Contact: 845-294-3100

Shown By

Agent Name: Ryan Duhaney
Agent Phone: (718) 395-5626
Agency Title: Century21 American Homes

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