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Off market
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  • $2,342,000

    291 Roaring Brook Rd, Chappaqua, NY 10514

    4beds
    4,644sqft
    SingleFamily
    Built in 1750
    2.19 Acres Lot
    $2,342,000 Zestimate®
    $504/sqft
    $12,971 Estimated rent

    Home value

    $2,342,000

    $2.13M - $2.58M

    $12,971/mo

    Zestimate® history
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    $12,971/mo

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    $15,726/mo

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    $15,726/mo

    Est. payment

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    What's special

    Welcome to the Jonathan Tompkins House, a true New Castle landmark dating back to 1750 where history and modern living intertwine. Ideally situated in the heart of Chappaqua and located within the award-winning Chappaqua School District, this fully furnished rental weaves centuries of New Castles past into its walls. Original hand-hewn beams and stained glass evoke timeless old-world charm, seamlessly blended with the modern conveniences of today.Step inside the original Dutch door into the dramatic main living area featuring soaring 17-foot ceilings and stained glass windows. The main living space transitions into the oldest area of the home, the dining room, where exposed weathered beams lead into the beautifully updated chefs kitchen, complete with Viking and Sub-Zero stainless-steel appliances, generous storage, and a breakfast nook. Also conveniently located on the first floor are a half bath and full laundry room.The second level, accessible from both the dining room and main living area, includes four bedrooms, highlighted by a spacious primary suite with an ensuite bath and a hidden secret passage leading to a flexible bonus space ideal for a home office or library. Additional features include two more bathrooms, a second large living area, and a loft with balcony that can serve as a playroom or fifth bedroom.Set across two storybook acres, the homes timeless proportions are thoughtfully grounded in the landscape. A double portico entrance, two-car garage, and Tesla charging station enhance the stately Greek Revival facade, while discreet solar panels and an energy-efficient heat pump support comfortable, low-maintenance living. A generous flat patio and two-story fenced playground provide exceptional outdoor spaces designed for both everyday enjoyment and effortless entertaining.Conveniently located near Chappaqua Crossings, town, top-rated schools, dining, and just three miles from the Metro-North station, this beautifully fully furnished historic residence delivers privacy, charm, and modern living in one unforgettable setting. 2026-04-23

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Zillow last checked:

    Listing updated:

    Source: Zillow Rentals

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 4
    • Full bathrooms: 3
    • 1/2 bathrooms: 1
    Heating
    • Heat Pump, Fireplace
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Dryer, Freezer, Microwave, Range Oven, Refrigerator, Washer
    • Laundry: In Unit
    Features
    • Flooring: Hardwood
    • Has fireplace: Yes
    Interior area
    • Total interior livable area: 4,644 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Other
    • Details: Contact manager
    Features
    • Patio & porch: Patio
    • Exterior features: Architecture Style: Colonial, Garden, High-speed Internet Ready, Shingle
    Lot
    • Size: 2.19 Acres
    Details
    • Parcel number: 55360092839

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Colonial
    • Property subtype: SingleFamily
    Condition
    • Year built: 1750

    Community & neighborhood

    Location
    • Region: Chappaqua

    Price history

    DateEventPrice
    4/24/2026Listing removed$11,500$2/sqft
    Source: Zillow Rentals Report a problem
    2/11/2026Listed for rent$11,500$2/sqft
    Source: Zillow Rentals Report a problem
    4/22/2022Sold$1,950,000+1.3%$420/sqft
    Source: OneKey® MLS as distributed by MLS GRID #H6159217 Report a problem
    2/16/2022Pending sale$1,925,000$415/sqft
    Source: OneKey® MLS as distributed by MLS GRID #H6159217 Report a problem
    2/15/2022Listed for sale$1,925,000-10.5%$415/sqft
    Source: OneKey® MLS as distributed by MLS GRID #H6159217 Report a problem
    12/30/2021Listing removed--
    Source: William Raveis Real Estate, Mortgage & Insurance Report a problem
    10/26/2021Listed for sale$2,150,000+372.5%$463/sqft
    Source: OneKey® MLS as distributed by MLS GRID #H6149260 Report a problem
    5/5/1997Sold$455,000$98/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025-- $172,950
    2024-- $172,950
    2023-- $172,950 +2.2%
    2022-- $169,250
    2021-- $169,250
    2020-- $169,250
    2019-- $169,250
    2018-- $169,250
    2017-- $169,250
    2016-- $169,250 -26.4%
    2015-- $230,000
    2014-- $230,000
    2013-- $230,000
    2012-- $230,000
    2011-- $230,000
    2009-- $230,000
    2008-- $230,000
    2007-- $230,000 +12.7%
    2006-- $204,000
    2005-- $204,000 +2%
    2004-- $200,000
    2003-- $200,000
    2002-- $200,000
    2001-- $200,000
    2000-- $200,000 +5.3%
    1999-- $190,000

    Find assessor info on the county website

    Neighborhood: 10514

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $2,342,000
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    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $2,342,000