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For sale
    • $1,050,000

    102 Pleasant Hill Road, New Windsor, NY 12553

    5beds
    4,499sqft
    Single Family Residence, Residential
    Built in 1833
    1.9 Acres Lot
    $-- Zestimate®
    $233/sqft
    $-- HOA

    What's special

    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!
    11 days
    845
    123

    Zillow last checked:

    Listing updated:

    Listed by:

    Howard Hanna Rand Realty 845-294-3100,

    Deidre McGinty 201-492-2128

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1058072MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Primary bedroom
      • Description: Primary bedroom with large closets and ensuite
      • Level: Second
      Bedroom 1
      • Description: Being used as office; Access to back patio and private bathroom
      • Level: First
      Bedroom 3
      • Description: Access to hall full bath
      • Level: Second
      Bedroom 4
      • Level: Third
      Bedroom 5
      • Level: Third
      Primary bathroom
      • Description: Walk in shower
      • Level: Second
      Bathroom 1
      • Description: Full bath accessible from office
      • Level: First
      Bathroom 2
      • Description: Powder room
      • Level: First
      Bathroom 3
      • Description: Full bath accessible from hall and third bedroom
      • Level: Second
      Bathroom 5
      • Level: Third
      Den
      • Level: Second
      Dining room
      • Description: Formal dining room with fireplace
      • Level: First
      Kitchen
      • Description: Eat in kitchen with large island and beverage station
      • Level: First
      Living room
      • Description: Formal dining room room with built-ins
      • Level: First
      Heating
      • Oil
      Cooling
      • Wall/Window Unit(s)
      Appliances
      • Included: Dishwasher, Gas Cooktop, Gas Oven, Microwave, Stainless Steel Appliance(s), Washer, Water Softener Owned
      • Laundry: Washer/Dryer Hookup
      Features
      • 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
      • Flooring: Hardwood, Other
      • Basement: Bilco Door(s),Full
      • Attic: Dormer
      • Number of fireplaces: 4
      • Fireplace features: Bedroom, Decorative, Wood Burning
      Interior area
      • Total structure area: 4,499
      • Total interior livable area: 4,499 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 8
      • Parking features: Driveway, Garage, Garage Door Opener, Heated Garage
      • Garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: Three Or More
      • Patio & porch: Patio
      • Exterior features: Garden, Mailbox, Rain Gutters
      • Has private pool: Yes
      • Pool features: In Ground, Salt Water
      • Fencing: Back Yard,Fenced,Wood
      • Has view: Yes
      • View description: Mountain(s)
      Lot
      • Size: 1.9 Acres
      • Features: Back Yard, Garden, Landscaped, Secluded
      Details
      • Parcel number: 3324890300000001068.0000000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence, Residential
      Materials
      • Stone
      • Foundation: Stone
      Condition
      • Updated/Remodeled
      • Year built: 1833

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Electricity Connected, Propane, Trash Collection Private

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: New Windsor

      Financial & listing details

      • Price per square foot: $233/sqft
      • Tax assessed value: $637,500
      • Annual tax amount: $25,138
      • Date on market: 10/22/2026
      • Listing agreement: Exclusive Right To Sell
      • Exclusions: Dining room chandelier, gym equipment
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        10/22/2026Listed for sale$1,050,000+76.5%$233/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1058072 Report a problem
        3/24/2021Listing removed--
        Source: Owner Report a problem
        10/13/2014Listing removed$595,000$132/sqft
        Source: Owner Report a problem
        7/15/2014Listed for sale$595,000+1.7%$132/sqft
        Source: Owner Report a problem
        8/27/2009Sold$585,000-17.7%$130/sqft
        Source: Public Record Report a problem
        1/12/2006Sold$711,000+84.7%$158/sqft
        Source: Public Record Report a problem
        2/4/1999Sold$385,000+32.8%$86/sqft
        Source: Public Record Report a problem
        2/20/1997Sold$290,000$64/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $637,500 +4.9%
        2024-- $607,500
        2023-- $607,500
        2022-- $607,500
        2021-- $607,500
        2020-- $607,500
        2019-- $607,500
        2018-- $607,500
        2017$18,531 $607,500 +57.8%
        2016-- $385,000
        2015-- $385,000
        2014-- $385,000
        2013-- $385,000
        2012-- $385,000
        2011-- $385,000
        2010-- $385,000
        2009-- $385,000
        2007-- $385,000
        2006-- $385,000
        2005-- $385,000
        2004-- $385,000
        2002-- $385,000
        2001-- $385,000
        2000-- $385,000
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 12553

        Getting around

        0 / 100
        Car-Dependent

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Cornwall Elementary School
        • Middle: Cornwall Middle School
        • High: Cornwall Central High School

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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