R
Landlord's Agent in 2026
Rachel Lacoste
Houlihan Lawrence Inc.
7 in this area
12 Total Sales
291 Roaring Brook Rd Chappaqua, NY 10514
4
Beds
3.5
Baths
4,644
Sq Ft
2.19
Acres Lot
Highlights
- Gourmet Kitchen
- 2.19 Acre Lot
- Viking Appliances
- Horace Greeley High School Rated A+
- Colonial Architecture
- Property is near public transit, schools, and shops
About This Home
As of April 2026Welcome 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 Castle’s 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 chef’s 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 home’s 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.
Last Agent to Rent the Property
Houlihan Lawrence Inc. Brokerage Phone: 914-238-4766 License #10401376398 Listed on: 02/11/2026
Last Renter's Agent
Unrepresented Buyer
Buyer Representation Office
Home Details
Home Type
- Single Family
Year Built
- Built in 1750 | Remodeled in 2007
Lot Details
- 2.19 Acre Lot
- Stone Wall
- Partially Fenced Property
- Landscaped
- Private Lot
- Level Lot
- Partially Wooded Lot
- Garden
Parking
- 2 Car Garage
- Electric Vehicle Home Charger
- Driveway
Home Design
- Mini Estate
- Colonial Architecture
- Entry on the 1st floor
- Frame Construction
- Shingle Siding
- Cedar
Interior Spaces
- 4,644 Sq Ft Home
- Furnished
- Built-In Features
- Woodwork
- Beamed Ceilings
- Cathedral Ceiling
- Recessed Lighting
- 1 Fireplace
- New Windows
- Double Pane Windows
- Blinds
- Entrance Foyer
- Family Room
- Formal Dining Room
- Wood Flooring
Kitchen
- Gourmet Kitchen
- Breakfast Area or Nook
- Gas Oven
- Gas Range
- Microwave
- Freezer
- Dishwasher
- Viking Appliances
- Stainless Steel Appliances
- Marble Countertops
Bedrooms and Bathrooms
- 4 Bedrooms
- En-Suite Primary Bedroom
- Dual Closets
- Walk-In Closet
- Double Vanity
- Soaking Tub
Laundry
- Laundry Room
- Dryer
- Washer
Home Security
- Smart Thermostat
- Fire and Smoke Detector
Outdoor Features
- Balcony
- Patio
- Exterior Lighting
- Playground
- Private Mailbox
Schools
- Roaring Brook Elementary School
- Robert E Bell Middle School
- Horace Greeley High School
Utilities
- Central Air
- Heat Pump System
- Heating System Uses Natural Gas
- Heating System Uses Oil
- Septic Tank
- High Speed Internet
Additional Features
- Solar Heating System
- Property is near public transit, schools, and shops
Community Details
- Building Fire Alarm
Listing and Financial Details
- Rent includes grounds care, trash collection
- 12-Month Minimum Lease Term
- Assessor Parcel Number 3600-092-008-00003-000-0009
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 04/24/2026 04/24/26 | Rented | $14,000 | +21.7% | -- | |
| 02/11/2026 02/11/26 | For Rent | $11,500 | 0.0% | -- | |
| 04/22/2022 04/22/22 | Sold | $1,950,000 | +1.3% | $420 / Sq Ft | View Prior Sale |
| 02/18/2022 02/18/22 | Pending | -- | -- | -- | |
| 02/15/2022 02/15/22 | For Sale | $1,925,000 | -- | $415 / Sq Ft |
Source: OneKey® MLS
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $81,559 | $172,950 | $90,000 | $82,950 |
| 2024 | $29,204 | $172,950 | $90,000 | $82,950 |
| 2023 | $27,569 | $172,950 | $90,000 | $82,950 |
| 2022 | $26,900 | $169,250 | $90,000 | $79,250 |
| 2021 | $26,562 | $169,250 | $90,000 | $79,250 |
| 2020 | $26,150 | $169,250 | $90,000 | $79,250 |
| 2019 | $99,616 | $169,250 | $90,000 | $79,250 |
| 2018 | $27,048 | $169,250 | $90,000 | $79,250 |
| 2017 | $0 | $169,250 | $90,000 | $79,250 |
| 2016 | $27,023 | $169,250 | $90,000 | $79,250 |
| 2015 | -- | $230,000 | $90,000 | $140,000 |
| 2014 | -- | $230,000 | $90,000 | $140,000 |
| 2013 | -- | $230,000 | $90,000 | $140,000 |
Source: Public Records
Agents Affiliated with this Home
-
Rachel Lacoste
-
U
Tenant's Agent in 2026
Unrepresented Buyer
Buyer Representation Office
-
Lori Hoffman-Chlapowski
Seller's Agent in 2022
Lori Hoffman-Chlapowski
Compass Greater NY, LLC
(914) 419-1192
16 in this area
30 Total Sales
-
Usha Subramaniam
Seller Co-Listing Agent in 2022
Usha Subramaniam
Compass Greater NY, LLC
(914) 572-3401
45 in this area
93 Total Sales
Map
Source: OneKey® MLS
MLS Number: 954764
APN: 553600 92.8-3-9
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The data relating to real estate for sale or lease on this web site comes in part from OneKey® MLS. Real estate listings held by brokerage firms other than Ten-X are marked with the OneKey® MLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker.
Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Copyright 2026 OneKey® MLS. All rights reserved.
Based on information submitted to the MLS GRID
Listings courtesy of OneKey® MLS as distributed by MLS GRID
Nearby Homes
- 335 Roaring Brook Rd
- 11 Wallace Way Unit 18
- 2 Dewitt Dr
- 26 Wallace Way
- 4 Wright Dr
- 24 North Way
- 17 Lila Ln
- 1 Hitching Post Ln
- 14 Annandale Rd
- 115 Old Roaring Brook Rd
- 12 Suzanne Ln
- 368 N Greeley Ave Unit 34G
- 22 Petersville Rd
- 86 Seven Bridges Rd
- 39 Mayberry Rd
- 14 Crossways
- 6 Killington St
- 21 Kitchawan Dr
- 20 Cardinal Place
- 110 Marcourt Dr
- 281 Roaring Brook Rd
- 301 Roaring Brook Rd Unit A
- 301 Roaring Brook Rd
- 300 Roaring Brook Rd
- 10 Danny Ln
- 308 Roaring Brook Rd
- 5 Danny Ln
- 315 Roaring Brook Rd
- 10 Kerry Ln
- 316 Roaring Brook Rd
- 20 Kerry Ln
- 10 Paula Place
- 1 Danny Ln
- 1 Hunting Ridge Rd
- 12 Hunting Ridge Place
- 329 Roaring Brook Rd
- 6 Paula Place
- 2 Danny Ln
- 16 Hunting Ridge Place
- 11 Hunting Ridge Place
Your Personal Tour Guide
Ask me questions while you tour the home.