Skip to content
102 Pleasant Hill Road, New Windsor, photo 1
Coming Soon
View all 12 photos
102 Pleasant Hill Road, photo 2
102 Pleasant Hill Road, photo 3
102 Pleasant Hill Road, photo 4
102 Pleasant Hill Road, photo 5
102 Pleasant Hill Road, photo 6
102 Pleasant Hill Road, photo 7
102 Pleasant Hill Road, photo 8
102 Pleasant Hill Road, photo 9
102 Pleasant Hill Road, photo 10
102 Pleasant Hill Road, photo 11
102 Pleasant Hill Road, photo 12

102 Pleasant Hill Road

$1,050,000

Est. $7,467/mo

New Windsor, NY 12553 · Orange County

Beds
5
Baths
4.5
Sqft
4,499
Status
Coming Soon
On site
Today

Know your budget before you tour. Get pre-qualified

About this home

An 1833 Georgian Colonial, Beautifully Preserved and Fully Reimagined COMING SOON! Showings begin 10/22/26. 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! Interior photos to be added soon.

Listed with Howard Hanna Rand Realty · Deidre McGinty · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Oct 15, 2026, 10:08 AM ET. ©2026 One Key MLS.

Estimate your monthly payment

Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and private mortgage insurance.

$7,466.86Total / mo

Estimated monthly payment

Principal & interest
$5,172.02(69.3%)
Taxes
$2,094.83(28.1%)
Insurance
$200.00(2.7%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

Never miss a property

Be the first to know when an Orange County home hits the market.

Save this search

Market insights

The market around New Windsor, NY

Current listings

New in the last 30 days

38

Oct 2026

Average price

Active listings

$609,402

Oct 2026

Average days on market

Active listings

130 days

Oct 2026

Computed from 147 active OneKey MLS listings in New Windsor, NY.

Similar homes in Orange County

See all 459
71 Peale Place, Montgomery, $1,100,000
71 Peale Place, Montgomery, NY
Photo 1 of 40
Coming SoonNew

$1,100,000

4 Bed • 2.5 Bath • 2,639 Sq. Ft.

71 Peale Place

Montgomery, NY 12549

Listed with Keller Williams Realty

1964 State Route 32, New Windsor, $795,000
1964 State Route 32, New Windsor, NY
Photo 1 of 4
Coming SoonNew

$795,000

4 Bed • 3 Bath • 3,160 Sq. Ft.

1964 State Route 32

New Windsor, NY 12553

Listed with RE/MAX Benchmark Realty Group

1150 E Mombasha Road, Monroe, $775,000
1150 E Mombasha Road, Monroe, NY
Photo 1 of 50
New

$775,000

4 Bed • 3 Bath • 3,212 Sq. Ft.

1150 E Mombasha Road

Monroe, NY 10950

Listed with RE/MAX Benchmark Realty Group