255 Pinesbridge Rd, Ossining, NY 10562
OFF MARKET

255 Pinesbridge Rd
Ossining, NY 10562

  • 34 Beds
  • 2 Baths
  • 2,900 sqft (on 2.25 acres)

$1,083,600

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $6,938/mo*
Refinance Your Home

$1,083,600

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $6,938/mo*
Refinance Your Home
34 Beds
2 Baths
2,900 sqft
(on 2.25 acres)

Local Information

  • Map ViewExplore the area around 255 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
1940
Lot Size
2.25 acres
Living Area
2,900 sqft
Price/Sqft
$374
Parking
Garage

About this House

LIVE AND VACATION IN THE SAME PLACE!!!! UNBELIEVABLE COUNTRY SETTING, YET MINUTES TO NYC. GREAT YORKTOWN SCHOOLS. PARADISE IS HERE!!!
255 Pinesbridge Rd, Ossining, NY 10562 is a 34 bedroom, 2 bathroom, 2,900 sqft single-family home built in 1940. It last sold for $425,000 on Feb 7, 2002. It is currently off market. The Trulia Estimate is $1,083,600, with a rent estimate of $4,192/month.

Home Details for 255 Pinesbridge Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: Stucco
Parking & Garage
GarageParking: Garage Detached

Community

Units in Building: 1

Lot Information

Lot Area: 2.25 acres

Price History for 255 Pinesbridge Rd

DatePriceEventSource
05/30/2008$690,000ListingRemovedAgent Provided
04/30/2008$690,000Listed For SaleAgent Provided
02/07/2002$425,000Sold
N/A

Market trends in Ossining

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
60
9MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$115,500
Home facts updated by county records

Comparable Sales for 255 Pinesbridge Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Adams Road, Ossining, NY
0.24
Single-Family Home
$816,000
04/22/26
3
2
1,658
16 Gregory Lane, Millwood, NY
0.29
Single-Family Home
$1,200,000
07/31/25
4
2.5
2,251
9 Possum Road, Ossining, NY
0.44
Single-Family Home
$721,000
02/27/26
3
2
1,528
801 Syska Road, Ossining, NY
0.49
Single-Family Home
$805,000
08/12/25
2
1.5
1,328
1002 Kitchawan Road, Ossining, NY
0.71
Single-Family Home
$799,000
09/24/25
3
2
2,067
81 Hidden Hollow Lane, Millwood, NY
0.48
Single-Family Home
$1,040,000
11/25/25
4
2.5
2,368
48 Glen Wood Rd, Millwood, NY
0.55
Single-Family Home
$651,000
04/15/26
3
2
1,344
20 Pamela Place, Millwood, NY
0.57
Single-Family Home
$1,436,000
12/05/25
4
2.5
3,103
51 Hidden Hollow Lane, Millwood, NY
0.55
Single-Family Home
$1,325,000
08/07/25
4
2.5
2,665
58 Hidden Hollow Lane, Millwood, NY
0.57
Single-Family Home
$1,225,047
03/04/26
3
2.5
2,144

Nearby homes

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Assigned Schools

These are the assigned schools for 255 Pinesbridge Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Ossining

At least 374 Trulia users voted on each feature.

  • 83 % Say it's dog friendly

  • 75 % Say car is needed

  • 75 % Say there's holiday spirit

  • 71 % Say there are sidewalks

  • 69 % Say yards are well-kept

  • 69 % Say people would walk alone at night

  • 66 % Say streets are well-lit

  • 66 % Say parking is easy

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's walkable to restaurants

  • 63 % Say they plan to stay for at least 5 years

  • 62 % Say kids play outside

  • 60 % Say it's quiet

  • 53 % Say neighbors are friendly

  • 50 % Say there's wildlife

  • 42 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Patricia Carrion
    "I never had any pets and the neighborhood residents are cordial to others. No one has given me any problems "
    0
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  • Katie Scarlett Ninivaggi
    "Concerts are offered in the summer, and the weekend farmer’s market is reliable in the warmer months. "
    0
    Flag
  • Katie
    "People are generally very kind and neighborly. There are many town events and small businesses that make an effort to cultivate community. "
    0
    Flag
  • Stetson Hundgen
    "Best Rivertown to be in. Fantastic diverse community full of great people. Best view on the Hudson. Close to so many great hikes and the city. "
    0
    Flag
  • Justin Lawrence
    "This neighborhood is wonderful. The people look out for one another and it’s safe. Been here for over nine years."
    0
    Flag
  • Brookelynn R.
    "I don't like the green color in the kitchen. For this wall it has to be one color how about cracked pepper or a darker hue. "
    0
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  • Marco Barros
    "It’s a quiet town and our family and friends have been walking late at night around town and the feel safe "
    0
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  • Afay69
    "All historical towns in Hudson valley are beautiful and unique and town of Ossining are bee one of them."
    0
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  • SEONGUK LIM
    "The roads are bad with potholes, and the school district is not good. North Ossining can be somewhat unsafe."
    0
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  • Milton Sandoval
    "I’ve lived in this neighborhood for more than 20 years. Since 2003, I attended AMD and OHS best town."
    6
    Flag
  • Gustavo D. L. P.
    "Plenty of space for having fun with a dog. Walking distance to parks. Little dogs have to be careful of coyotes and foxes. "
    13
    Flag
  • Edit
    "Many families, great parks, close to Hudson and other recreational areas, park school is great. Mostly Latino population; nice people in general. Stores are close and well stock, if you don’t want to leave the town you can find pretty much everything here."
    18
    Flag
  • Lupe G.
    "forest Of fears, river front summer Friday nights, tree lighting, trick-or-treat, culrural festivals, 4th of July fire works, summer street fair. learn and explore weekend sessions. library movie nights. "
    10
    Flag
  • Stetson H.
    "The Ossining Farmers market is one of the best in Westchester. There are several community events throughout the year down by the waterfront. "
    3
    Flag
  • Maramaidhah
    "It is safe and it is full of lights I love it so much. I also like the neighborhood that is around me."
    2
    Flag
  • Jmarques525
    "A lot of activities for kids through the town programs. These is a big sence of community here with diversity. "
    3
    Flag
  • Marco D.
    "I lived in this neighborhood for three years and it’s been lovely. The area is changing and a lot of new upgrades coming to the community. "
    2
    Flag
  • Dave B.
    "Very diverse, right by the water, very close to the train station and an easy ride to NYC. Good food and good people so you can’t go wrong. "
    2
    Flag
  • Dave B.
    "Historical feel, big town but small town feeling, train station right on the water and very quick train ride into NYC "
    0
    Flag
  • Savannah M.
    "It’s a very friendly community without a lot of crowds. It feels very small town and that’s very nice. "
    0
    Flag
  • Veronica A. C.
    "It is a great school district and a nice Town to enjoy in parks, lot of restaurants and a very nice library "
    1
    Flag
  • Daniela .
    "I don’t own a dog, but my neighbor is pet friendly and very clean. All dogs get alone well and owners clean very nicely afterwards. Happy place for everyone. "
    0
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  • Edisonlatin32
    "It’s nice live here it’s quiet no loud music no noises no drogs I love this town but I don’t like the traffic and the police and the taxi drivers "
    1
    Flag
  • Jessica P.
    "Safe. School districts the best in education. Ossining has a big library for kids to study. Open door clinics in ossining and along other close hospital like Phelps "
    2
    Flag
  • Mvportilla
    "Nice town to have family, great schools with very good and humanity teachers. So many parks for kids, beautifull Hudson River view ."
    3
    Flag
  • Vera G.
    "It’s quiet, rural and the neighbors are nice. There is tons of wildlife including birds and deer. It is serene and beautiful."
    0
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  • Stacie A.
    "I’ve lived here for 2 years. It’s quite. Nice neighborhood for people with children. I love the waterfront and seeing people walking their dogs "
    0
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  • Vera G.
    "My neighborhood is quiet and the rural part of town, but within 2 -4 miles of everything. There is plenty of open space"
    5
    Flag
  • Gk4sk
    "It is a very nice place to raise family. It has an easy commute to New York City. Also has lot of parks and play grounds. "
    1
    Flag
  • Gk4sk
    "Ossining has nice school district, large numbers of parks and playgrounds and easy commute to NewYork city."
    1
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 255 Pinesbridge Rd

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Off Market Homes Near 255 Pinesbridge Rd

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