27 Underhill Rd, Ossining, NY 10562
Property image
Property image
OFF MARKET

$974,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,370 sqft

27 Underhill Rd, Ossining, NY 10562

Est. Refi. Payment $6,259/mo*
Refinance Your Home
Currently Off Market - Sold Jul 22, 2014 for $568,000

Home Value

Trulia Estimate
$974K
Since last month
Increased$4K (+0.4%)
Since last year
Increased$43K (+4.6%)
Since last sale
Increased$409K (+71.9%)
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 +67% in the last 10 years
MonthEstimated value
2026
August 2026$977K
July 2026$972K
June 2026$984K
May 2026$958K
April 2026$945K
March 2026$939K
February 2026$909K
January 2026$929K
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
59 Watson Avenue, Ossining, NY
0.23
Single-Family Home
$649,222
05/08/26
3
2
1,730
5 Cedar Place, Ossining, NY
0.30
Single-Family Home
$699,000
12/19/25
3
3
2,272
3 Birch Court, Ossining, NY
0.14
Single-Family Home
$955,000
08/11/26
3
2.5
2,596
15 Prospect Avenue, Ossining, NY
0.51
Single-Family Home
$600,000
06/25/26
3
2
1,520
39 Hamilton Avenue, Ossining, NY
0.72
Single-Family Home
$540,000
03/23/26
3
1.5
2,198
2 Oak Hill Terrace, Ossining, NY
0.06
Single-Family Home
$995,000
01/30/26
4
3.5
3,300
8 Eldridge Avenue, Ossining, NY
0.40
Single-Family Home
$625,000
02/18/26
3
1.5
1,610
41 Clinton Avenue, Ossining, NY
0.36
Single-Family Home
$750,000
07/29/26
3
3
1,668
7 Fuller Road, Ossining, NY
0.42
Single-Family Home
$625,000
09/02/25
4
2
1,692
39 Washington Avenue, Ossining, NY
0.52
Single-Family Home
$825,000
05/06/26
4
2
2,521

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
1 Noel Drive, Ossining, NY 10562
0.05
$860,000
4
2.5
3,551
Recently Sold
2 Oak Hill Terrace, Ossining, NY 10562
0.06
$995,000
4
3.5
3,300
Recently Sold
25 Wolden Road, Ossining, NY 10562
0.11
$756,900
3
2.5
1,723
Off Market
21 Overton Road, Ossining, NY 10562
0.11
$767,300
3
3
2,274
Off Market
33 Noel Drive, Ossining, NY 10562
0.17
$1,098,500
5
4
3,070
Off Market
25 Birch Court, Ossining, NY 10562
0.11
$1,083,000
3
3.5
3,339
Off Market
49 Wolden Road, Ossining, NY 10562
0.20
$652,000
2
2
1,412
Off Market
3 Birch Court, Ossining, NY 10562
0.14
$955,000
3
2.5
2,596
Recently Sold
61 Underhill Road, Ossining, NY 10562
0.15
$950,000
4
2.5
3,378
For Sale
59 Ellis Place, Ossining, NY 10562
0.17
$626,700
3
2
1,432
Off Market
11 Birch Court, Ossining, NY 10562
0.16
$1,063,500
4
3.5
3,878
Off Market
4 Linden Avenue, Ossining, NY 10562
0.17
$660,100
3
1.5
1,700
Off Market

Local Information

  • Map ViewExplore the area around 27 Underhill 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
1927
Living Area
2,370 sqft
Price/Sqft
$411

About this House

This single-family home is located at 27 Underhill Rd, Ossining, NY. 27 Underhill Rd is in Ossining, NY and in ZIP code 10562. This property has 3 bedrooms, 2 bathrooms and approximately 2,370 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1927.
27 Underhill Rd, Ossining, NY 10562 is a 3 bedroom, 2 bathroom, 2,370 sqft single-family home built in 1927. It last sold for $568,000 on Jul 22, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $974,000, with a rent estimate of $4,232/month.

Home Details for 27 Underhill Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 7
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: OtherExterior: Stucco
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1927
Property Type / Style
Property Type: Single Family HomeArchitecture: Tudor

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price and Tax history

DateEventPrice
Jul 22, 2014
Source: OneKey® MLS as distributed by MLS GRID #H3405378
Sold
$568,000
Mar 29, 2014
Source: Agent Provided
PriceChange
$578,000
Price decreased by 2%
Mar 3, 2014
Source: Agent Provided
Listed For Sale
$588,000
Sep 28, 1998
Source: N/A
Sold
$308,000

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

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Afay69
    "All historical towns in Hudson valley are beautiful and unique and town of Ossining are bee one of them."
    0
    Flag
  • SEONGUK LIM
    "The roads are bad with potholes, and the school district is not good. North Ossining can be somewhat unsafe."
    1
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 27 Underhill Rd

  • What is 27 Underhill Rd estimated to be worth?
    Trulia's estimated value for 27 Underhill Rd in Ossining, NY is $974,000.
  • What is the price history for 27 Underhill Rd?
    27 Underhill Rd in Ossining, NY last sold for $568,000 in July 2014.
  • Is Ossining a buyer's or seller's market?
    Ossining is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Ossining?
    Residents describe Ossining, NY as dog-friendly, pedestrian-friendly, and well-kept. See recently sold homes in Ossining, NY.
  • Does 27 Underhill Rd have air conditioning?
    Yes, 27 Underhill Rd in Ossining, NY has air conditioning.
  • Does 27 Underhill Rd have laundry facilities?
    Yes, 27 Underhill Rd in Ossining, NY has in-unit laundry.

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Off Market Homes Near 27 Underhill Rd

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