From the outside, 159/161 Chappaqua Road presents as a charming farmhouse—but it offers far more than its picturesque post-and-rail fence suggests. Set on 1.29 acres, with a newly renovated guest house Cottage, this 19th-century compound seamlessly blends historic character with modern luxury, featuring a four-bedroom, 3.1-bath Colonial-style Main House. A bluestone walkway leads to the stately entry hall of the main home, where approximately 3,000 square feet of living space highlights original antique flooring, exposed brick and beams, sawn wood paneling, marble fireplace, multiple porches and balconies, French doors, and classic built-ins. These timeless details are thoughtfully complemented by contemporary upgrades, including granite countertops, stainless steel appliances, marble baths, two-zone central air, a security system, hot tub and generator. The main residence includes a spacious primary suite, three additional bedrooms, a home office, and a fully renovated kitchen with a butler’s pantry and mudroom. Recent enhancements feature an oversized sliding French door opening to a two-tiered stone porch complete with a luxury hot tub and firepit. The guest house Cottage offers exceptional versatility, with a living and dining area, full kitchen, powder room, a primary bedroom with a spa-like bath, and an additional ensuite bedroom with a separate sitting area—ideal for guests, extended family, or rental potential. Additional amenities include a detached garage and an oversized shed.
Single-familyProperty Type
1820Year Built
0.89 acresLot Size
$649Price/Sq.Ft.
1 garage spacesParking
Listing by Marcene Hedayati• Corcoran Legends Realty
Est. $4,585 per month, based on comparable rentals
Sale and tax history for 159-161 Chappaqua Rd
Sale History
Tax History
Date
Event
Price
OneKey® MLS as Distributed by MLS Grid #984968
Jul 14, 2026
Sold
$2,000,000
$649/sq ft
May 13, 2026
Pending
—
Apr 27, 2026
Listed
$1,975,000
$641/sq ft
OneKey® MLS as Distributed by MLS Grid #H6131290
Nov 12, 2021
Sold
$1,083,800
$352/sq ft
Sep 6, 2021
Pending
—
Jul 16, 2021
Listed
$1,165,000
$378/sq ft
From the outside, it may look like a charming farm house but 159/161 Chappaqua Rd. is far more than just the post and rail fence that surrounds it. Set on 1.35 acres this 19th century compound, with a colonial “main house” and “guest house,” features the best of old world charm and modern luxury. Up the bluestone walkway into the main house’s stately entry hall, 3,000 sqft of antique original flooring, exposed brick and beams, sawn wood paneling, tiled fireplaces, screened porches, French doors and classic built-ins are contrasted with granite countertops and stainless steel appliances, wine bar and fridge, marble baths, 2-zone AC, security system and a generator;primary suite, 3 additional bedrooms, office and a totally renovated kitchen, butler’s pantry and mudroom. New utilities include oil tank, hot water tank, AC system, LED lighting and foam insulation. The Guest House, recently rebuilt has a living room, kitchen, 2 bedrooms and 2 baths and is the perfect rental, in-law cottage. Additional Information: Amenities:Guest Quarters,HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,
Middle Or Junior School: Anne M Dorner Middle School
Middle Or Junior School District: Ossining
High School: Ossining High School
High School District: Ossining
Location Information
Village: Briarcliff Manor
Directions: Rte 9A to Chappaqua Road to # 159-161
County Or Parish: Westchester County
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 0.35 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Westchester County
APN: 554289A09001800020960000000
Home facts updated by county records on Aug 10, 2026
Around this home
Schools
Brookside School
Public 1-2 • Assigned • 0.9mi
Anne M Dorner Middle School
Public 6-8 • Assigned • 1.7mi
6/10
Ossining High School
Public 9-12 • Assigned • 1.5mi
4/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 99° expected this year, 15 days in 30 years
6/10 Wind Factor
27% chance of strong winds in next 30 years
4/10 Air Factor
4 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Briarcliff Manor, NY • 10510
Average low and high temperatures (°F)
34
22
38
24
54
35
63
44
71
53
82
64
87
69
81
61
76
58
67
48
54
39
40
27
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
95/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 8% for direct sun exposure in Briarcliff Manor. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10 hrs
6.4 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.85M – $2.23M
Reach more buyers when you sell with Redfin. Plus, you'll save $19,420 in fees.