Suburban Realty

Getting you the home you want in Rockland & Orange County, New York

  • Rockland County
  • Search By School District
  • Blog
  • Contact
You are here: Home / 102 Pleasant Hill Road, New Windsor, NY 12553 (MLS # 1058072)

102 Pleasant Hill Road, New Windsor, NY 12553 (MLS # 1058072)

Request More Info Schedule a Showing Share Print
View Virtual Tour
Price $1,050,000
Status Active
Beds 5
Baths 4.5 Baths
Home size 4,499 sqft
Lot Size 1.90 ac
Days on Market 1
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!
Property Type(s): Single Family
Last Updated 10/21/2026 Year Built 1833
Garage Spaces 3.0 County Orange

SCHOOLS

Elementary School Cornwall Elementary School
Jr. High School Cornwall Middle School
High School Cornwall Central High School

Additional Details

AIR Wall/Window Unit(s)
AIR CONDITIONING Yes
APPLIANCES Dishwasher, Gas Cooktop, Gas Oven, Microwave, Stainless Steel Appliance(s), Washer, Water Softener Owned
BASEMENT Full
CONSTRUCTION Stone
EXTERIOR Garden, Rain Gutters
FIREPLACE Yes
GARAGE Yes
HEAT Oil
INTERIOR Beamed Ceilings, Breakfast Bar, Built-in Features, Eat-in Kitchen, Entrance Foyer, High Ceilings, Kitchen Island, Storage
LOT 1.9 acre(s)
LOT DESCRIPTION Back Yard, Garden, Landscaped, Secluded
PARKING Driveway, Garage, Garage Door Opener, Heated Garage
POOL Yes
POOL DESCRIPTION In Ground, Salt Water, Private
SEWER Septic Tank
STORIES 3+
STYLE Colonial
TAXES 25138.25
UTILITIES Electricity Connected, Propane
VIEW Yes
VIEW DESCRIPTION Mountain(s)
WATER Private, Well

Location

 

Contact us about this Property

 / 
We respect your online privacy and will never spam you. By submitting this form with your telephone number you are consenting for Janet Eisenberg to contact you even if your name is on a Federal or State "Do not call List".

Listed with Howard Hanna Rand Realty
HGMLS logo Copyright 2026 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.
The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than Suburban Realty are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. Information deemed reliable but not guaranteed.
Date Last Updated: 10/22/26 7:25 AM PDT

This IDX solution is (c) Diverse Solutions 2026.

Share on Twitter Twitter
Share on Facebook Facebook
Share by Email Email
Email a Friend

Share this:

  • Click to share on Facebook (Opens in new window)
  • Click to share on Twitter (Opens in new window)
  • Click to share on Pinterest (Opens in new window)
  • Click to email a link to a friend (Opens in new window)
  • Click to print (Opens in new window)
  • More
  • Click to share on LinkedIn (Opens in new window)
  • Click to share on Reddit (Opens in new window)
  • Click to share on Tumblr (Opens in new window)

Real Estate Search

Calculate Mortgage Payments

mortgage calculator

About Janet

I have been a Realtor since 1982, and loving it. Serving Rockland County, New York, as well as Bergen County, New Jersey. I am with you every step of the way.

  • Email
  • Facebook
  • Phone

Janet Eisenberg

Licensed Real Estate Broker in
New York, & New Jersey

31 Drexel Court
New City, NY 10956

info@suburban-realty.com
Phone: (845) 425-3379
Cell: (914) 714-2004

Standard Operating Procedures (SOP)

Affiliations


Equal Housing


Member of the Realtor Association


MLS

Janet Eisenberg – Broker at Suburban Realty Inc.

My Promise

Whether you are listing your property or looking for your new home, we make the process easy. 30+ years of experience and many happy clients make us a trusted partner in a life-changing event. We are looking forward to your call.