808 Pinesbridge Rd, Ossining, NY 10562
OFF MARKET

$1,886,900

Trulia Estimate
  • 5 Beds
  • 5.5 Baths
  • 4,966 sqft (on 5 acres)

808 Pinesbridge Rd, Ossining, NY 10562

Kitchawan
Est. Refi. Payment $11,996/mo*
Refinance Your Home
Currently Off Market - Sold Feb 11, 2021 for $890,000

Home Value

Trulia Estimate
$1.89M
Since last month
Increased$8K (+0.4%)
Since last year
Increased$150K (+8.6%)
Since last sale
Increased$1M (+112.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +62% in the last 10 years
MonthEstimated value
2026
August 2026$1.89M
July 2026$1.89M
June 2026$2.06M
May 2026$1.89M
April 2026$1.88M
March 2026$1.73M
February 2026$1.73M
January 2026$1.68M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
36 Overbrook Dr, Millwood, NY
0.30
Single-Family Home
$1,075,000
06/04/26
3
3
3,106
43 Random Farms Circle, Chappaqua, NY
0.89
Single-Family Home
$1,660,000
10/03/25
5
4.5
5,357
73 Random Farms Drive, Chappaqua, NY
0.86
Single-Family Home
$1,800,000
10/09/25
5
4.5
5,089
35 Whitlaw Lane, Chappaqua, NY
0.74
Single-Family Home
$1,775,000
02/20/26
4
3.5
3,732
250 Route 100, Mount Kisco, NY
1.08
Single-Family Home
$1,470,000
03/30/26
5
3.5
4,400
81 Hidden Hollow Lane, Millwood, NY
0.61
Single-Family Home
$1,040,000
11/25/25
4
2.5
2,368
10 Lakeview Road, Ossining, NY
0.72
Single-Family Home
$715,000
08/26/26
3
2.5
2,270
20 Pamela Place, Millwood, NY
0.72
Single-Family Home
$1,436,000
12/05/25
4
2.5
3,103
350 Wooded Hill Court, Chappaqua, NY
1.18
Single-Family Home
$2,260,100
07/15/26
4
4.5
4,681
550 Saw Mill River Road, Millwood, NY
0.57
Single-Family Home
$799,000
04/27/26
3
3
1,692

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
796 Pinesbridge Road, Ossining, NY 10562
0.17
$1,027,100
3
2.5
2,900
Off Market
801 Syska Road, Ossining, NY 10562
0.18
$873,400
2
1.5
1,328
Off Market
800 Syska Road, Ossining, NY 10562
0.23
$874,000
3
2
1,196
Off Market
6 Timberline, Millwood, NY 10546
0.28
$1,068,800
3
3
2,728
Off Market
24 Overbrook Drive, Millwood, NY 10546
0.32
$1,084,400
3
3.5
3,412
Off Market
7 Deer Ridge, Millwood, NY 10546
0.38
$1,119,700
3
3
3,005
Off Market
245A Pinesbridge Road, Ossining, NY 10562
0.37
$1,012,600
3
2.5
2,207
Off Market
15 Deer Ridge, Millwood, NY 10546
0.39
$1,178,800
3
3.5
2,939
Off Market
16 Gregory Lane, Millwood, NY 10546
0.39
$1,303,700
4
2.5
2,251
Off Market
255 Chadeayne Road, Ossining, NY 10562
0.45
$818,700
4
2.5
2,310
Off Market
10 Gregory Lane, Millwood, NY 10546
0.43
$1,919,700
4
3.5
3,422
Off Market
265 Chadeayne Road, Ossining, NY 10562
0.49
$1,288,900
4
2.5
2,392
Off Market

Local Information

  • Map ViewExplore the area around 808 Pinesbridge Rd.
  • Schools1 Preschool School4 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Lot Size
5 acres
Living Area
4,966 sqft
Price/Sqft
$380
Parking
Garage

About this House

Old world classic charm & grandeur meets new world style & updates in this ch colonial. 5 acre setting backs to Aqueduct. A true extended family compound- 5 BR/5.1 Bath main house w/guest wing/separate entry, 3 home offices, gracious FLR/FR/FDR/EIK/Butlers Pantry, Sunroom, Master suite, , additional en-suite BR/baths. 1 BR Guest house/legal rental, 3 story barn, gazebo. Country setting, private yet close to all. Gleaming newly refinished oak flrs, millwork, detail & moldings abound, French drs, high ceilings,3 FPL's. New updates include lighting, plumbing, septic, alarm, interior painting, stainless steel appliances, fixtures, etc.. 3 Car garage, low taxes, impeccable condition. Sophisticated and warm, this striking residence has generously scaled rooms, exceptional design & detail, & radiates light & comfort. Flexible layout for live/work, extended family, plus income producing guest cottage, and barn with potential for artist studio, storage, gym, yoga, imagine the possibilities.
808 Pinesbridge Rd, Ossining, NY 10562 is a 5 bedroom, 6 bathroom, 4,966 sqft single-family home in Kitchawan, built in 1930. It last sold for $890,000 on Feb 11, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,886,900, with a rent estimate of $7,906/month.

Home Details for 808 Pinesbridge Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningCooling System: CentralHeating Fuel: Oil
Interior Details
Number of Rooms: 16Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Lot Information

Lot Area: 5.00 acres

Price and Tax history

DateEventPrice
Feb 11, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6078293
Sold
$890,000
Oct 24, 2020
Source: Agent Provided
Listed For Sale
$885,000
Aug 8, 2019
Source: OneKey® MLS as distributed by MLS GRID #H4905889
Sold
$775,000
May 15, 2019
Source: Agent Provided
Pending
$799,000
Mar 19, 2019
Source: Agent Provided
PriceChange
$799,000
Price decreased by 2%

Market trends in Ossining

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
60

Around this home

Neighborhood Overview

Kitchawan
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 808 Pinesbridge Rd

  • What is 808 Pinesbridge Rd estimated to be worth?
    Trulia's estimated value for 808 Pinesbridge Rd in Ossining, NY is $1,886,900.
  • What is the price history for 808 Pinesbridge Rd?
    808 Pinesbridge Rd in Ossining, NY last sold for $890,000 in February 2021.
  • Is Ossining a buyer's or seller's market?
    Ossining is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 808 Pinesbridge Rd?
    The closest schools to 808 Pinesbridge Rd in Ossining, NY are Anne M Dorner Middle School (rated 6/10), Brookside School (Elementary), Claremont School (Elementary, rated 5/10).
  • Does 808 Pinesbridge Rd have air conditioning?
    Yes, 808 Pinesbridge Rd in Ossining, NY has air conditioning.
  • Does 808 Pinesbridge Rd have laundry facilities?
    Yes, 808 Pinesbridge Rd in Ossining, NY has in-unit laundry.

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Off Market Homes Near 808 Pinesbridge Rd

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