291 Roaring Brook Rd

4,644 Sq. Ft.
$30 / Sq. Ft.
4,644
Sq. Ft.
$30
per Sq. Ft.

Description

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 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...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 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, stained glass windows, and a working fireplace. 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 façade, 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.
  1. Listed by Rachel Lacoste • Houlihan Lawrence Inc.
    P: (914)-238-4766 C: (203)-228-2264 RLacoste@houlihanlawrence.com

Property Details for 291 Roaring Brook Road

City/Township
New Castle
Architectural Style
Colonial, Mini Estate
Garage Spaces
2.00
Waterfront
No
Pets Allowed
No
LISTING UPDATED: 02/11/2026 09:04 AM

Property Details for 291 Roaring Brook Road

StatusActive
MLS #954764
Days on MarketListed Today
Rental Incentives-
Available Date03/27/2026
Lease TermLease Length: 12 Months
FurnishedFully Furnished
Compass TypeSingle Family
MLS TypeSingle Family Residence
Year Built1750
Lot Size2.19 AC / 95,396 SF
CountyWestchester County

Location

Listing Courtesy of Houlihan Lawrence Inc.
Add your commute

Building Information for 291 Roaring Brook Road

Stories-Year Built1750Building Size-Lot Size2.19 AC / 95,396 SF

Property Information for 291 Roaring Brook Road

Summary
Location and General Information
  • Senior Community YN: No
  • Year Built Effective: 2007
  • Property Attached: No
  • Structure Type: false
  • Property Condition: Updated/Remodeled
  • State Or Province: NY
School Information
  • School District: Chappaqua
  • Elementary School District: Chappaqua
  • Elementary School: Roaring Brook
  • Middle Or Junior School District: Chappaqua
  • Middle Or Junior School: Robert E Bell School
  • High School District: Chappaqua
  • High School: Horace Greeley High School
Rental
Rental
  • Lease Term: 12 Months
  • Rent Includes: Grounds Care, Trash Collection
  • RentSpree Y/N: false
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 3600-092-008-00003-000-0009
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Balcony, Beamed Ceilings, Blinds, Built-in Features, Cathedral/Vaulted/High Ceiling, Chefs Kitchen, Colonial, Double Pane Windows, Double Vanity, Entertainment Cabinets, Entrance Foyer, Family Room, Fire Alarm, Formal Dining, Fully Furnished, Garage(s), Garden, Hardwood Floors As Seen, High Ceilings, High Speed Internet, His and Hers Closets, Laundry Room, Lighting, Mailbox, Marble Counters, Mini Estate, Natural Woodwork, New Windows, Original Details, Partial, Patio, Playground, Primary Bathroom, Public, Recessed Lighting, Smart Thermostat, Smoke Detector(s), Soaking Tub, Walk In Closet
  • Furnished: Furnished
  • Interior Features: Beamed Ceilings, Built-in Features, Cathedral Ceiling(s), Chefs Kitchen, Double Vanity, Entertainment Cabinets, Entrance Foyer, Formal Dining, High Ceilings, High Speed Internet, His and Hers Closets, Marble Counters, Natural Woodwork, Original Details, Primary Bathroom, Recessed Lighting, Smart Thermostat, Soaking Tub, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Freezer, Gas Oven, Gas Range, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
  • Total Rooms: 14
  • Attic Description: None
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Family Room
  • Location Amenities: Stainless Steel Appliances, Balcony, Hardwood Floors As Seen, Cathedral/Vaulted/High Ceiling, Chef's Kitchen, Dual Sinks, Entry Foyer, Foyer, Formal Dining Room, High Ceilings, High Speed Internet, Marble Countertops, Original Details, Soacking Tub, Walk In Closet, Garden, Privacy, Brownstone, Patio, Double Paned Windows, New Windows
  • Laundry Features: Laundry Room
  • Security Features: Fire Alarm,Smoke Detector(s)
  • Window Features: Blinds,Double Pane Windows,New Windows
  • Flooring: Hardwood
  • Inclusions: Fully Furnished
  • Living Area: 4,644.00
  • Basement: No
Exterior Features
  • Exterior Features: Balcony, Garden, Lighting, Mailbox, Playground
  • Exterior Property Features: Balcony, Garden, Lighting, Mailbox, Playground, Patio, Driveway, Electric Vehicle Charging Station(s), Garage, Private, Partial, Blinds, Double Pane Windows, New Windows, Landscaped, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Sloped, Stone/Brick Wall
  • Elevation Certificate: No
  • Entry Level: 1
  • Fencing: Partial
  • Patio And Porch Features: Patio
  • Construction Materials: Cedar, Frame, Shingle Siding
  • Road Responsibility: Tenant
  • Other Structures: Garage(s)
  • Pool Private: No
Lot Information
  • Lot Features: Garden, Landscaped, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Sloped, Stone/Brick Wall
  • Site Features: Garden, Landscaped, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Sloped, Stone/Brick Wall
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Electric Vehicle Charging Station(s), Garage, Private
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Heat Pump, Natural Gas, Oil, Solar
  • Heat Fuel Type: Heat Pump, Natural Gas, Oil, Solar
  • Number Of Heating Zones: 3
  • Sewer: Septic Tank
  • Water Source: Public
  • Utilities: Electricity Connected, Trash Collection Public, Water Connected
Green Features
  • Green Features: Blinds, Double Pane Windows, New Windows, Dishwasher, Dryer, Freezer, Gas Oven, Gas Range, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer, Heat Pump, Natural Gas, Oil, Solar, Balcony, Garden, Lighting, Mailbox, Playground

Property History for 291 Roaring Brook Road

DateEvent & SourcePriceAppreciation
Feb 11, 2026

Listed (Active)

ONEKEY #954764

$11,500
Mar 1, 2010

Expired

ONEKEY #H3000393

Jan 23, 2010

Expired

ONEKEY #H2917800

Jan 5, 2010

Listed (Active)

ONEKEY #H3000393

$2,750
Jun 4, 2009

Listed (Active)

ONEKEY #H2917800

$2,850
May 27, 2008

Rented

HGMLS #2811623

$2,850
May 20, 2008

Contract

HGMLS #2811623

Apr 10, 2008

Listed (Active)

HGMLS #2811623

$2,900
Aug 13, 2005

Expired

ONEKEY #H2511251

May 13, 2005

Listed (Active)

ONEKEY #H2511251

$2,800
DateEvent & SourcePrice
02/11/2026

Listed (Active)

ONEKEY #954764

$11,500
03/01/2010

Expired

ONEKEY #H3000393

01/23/2010

Expired

ONEKEY #H2917800

01/05/2010

Listed (Active)

ONEKEY #H3000393

$2,750
06/04/2009

Listed (Active)

ONEKEY #H2917800

$2,850
05/27/2008

Rented

HGMLS #2811623

$2,850
05/20/2008

Contract

HGMLS #2811623

04/10/2008

Listed (Active)

HGMLS #2811623

$2,900
08/13/2005

Expired

ONEKEY #H2511251

05/13/2005

Listed (Active)

ONEKEY #H2511251

$2,800

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 291 Roaring Brook Road

This home is within Chappaqua Central School District.
Rating
School
Type
Grades
Distance
Public - K to 4
Public - 5 to 8
Public - 9 to 12
Public - K to 4
Rating
School
Distance
Roaring Brook School
PublicK to 4

Robert E Bell School
Public5 to 8

Horace Greeley High School
Public9 to 12

Westorchard School
PublicK to 4

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

291 Roaring Brook Road is available for rent in Chappaqua, NY 10514. This property was listed on February 11, 2026 by Houlihan Lawrence Inc., it's currently listed at $11,500. It has been on the market for a total of 0 days and was last rented on May 27, 2008. This listing's school district is Chappaqua Central School District. Nearby schools include Roaring Brook School, Robert E Bell School and Horace Greeley High School. 291 Roaring Brook Road is a 4-bed, 4-bath, 4,644 sqft a property built in 1750.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Houlihan Lawrence Inc.

Based on information submitted to the MLS GRID as of 02/11/2026 09:04 AM. 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. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.