16 Overlook Rd, Ossining, NY 10562
Property image
Property image
OFF MARKET

$1,207,300

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,659 sqft (on 1.01 acres)

16 Overlook Rd, Ossining, NY 10562

Est. Refi. Payment $7,703/mo*
Refinance Your Home
Currently Off Market - Sold Oct 2, 2020 for $767,000

Home Value

Trulia Estimate
$1.21M
Since last month
Increased$800 (+0.1%)
Since last year
Increased$133K (+12.3%)
Since last sale
Increased$439K (+57.2%)
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 +115% in the last 10 years
MonthEstimated value
2026
August 2026$1.21M
July 2026$1.21M
June 2026$1.19M
May 2026$1.15M
April 2026$1.13M
March 2026$1.1M
February 2026$1.08M
January 2026$1.07M
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
6 Ichabod Lane, Ossining, NY
0.25
Single-Family Home
$875,000
03/09/26
3
2.5
2,030
55 Hoags Cross Road, Ossining, NY
0.28
Single-Family Home
$865,000
08/04/26
3
2
2,292
10 Lakeview Road, Ossining, NY
0.54
Single-Family Home
$715,000
08/26/26
3
2.5
2,270
9 Possum Road, Ossining, NY
0.58
Single-Family Home
$721,000
02/27/26
3
2
1,528
18 Adams Road, Ossining, NY
0.66
Single-Family Home
$816,000
04/22/26
3
2
1,658
83 McDonald Road, Ossining, NY
0.52
Single-Family Home
$1,075,000
10/15/25
5
3
3,972
20 Highview Road, Ossining, NY
0.83
Single-Family Home
$845,000
06/26/26
3
2
1,672
90 Shingle House Road, Millwood, NY
0.87
Single-Family Home
$850,000
01/15/26
4
3
2,318
83 Inningwood Road, Millwood, NY
0.83
Single-Family Home
$1,090,000
10/15/25
4
2
1,874
352 Croton Dam Road, Ossining, NY
0.60
Single-Family Home
$1,450,000
08/19/26
4
3.5
4,290

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
4 Lake Way, Ossining, NY 10562
0.15
$1,372,800
3
2.5
2,732
Off Market
3 Lake Way, Ossining, NY 10562
0.18
$875,400
2
2.5
1,940
Off Market
166 Pinesbridge Road, Ossining, NY 10562
0.21
$963,900
3
2.5
1,598
Off Market
6 Ichabod Lane, Ossining, NY 10562
0.25
$875,000
3
2.5
2,030
Recently Sold
55 Hoags Cross Road, Ossining, NY 10562
0.28
$865,000
3
2
2,292
Recently Sold
56 Twin Ridges Road, Ossining, NY 10562
0.35
$1,276,400
3
3.5
3,679
Off Market
130 Pines bridge Road, Ossining, NY 10562
0.31
-
-
-
-
Off Market
130 Pinesbridge Road, Ossining, NY 10562
0.32
$1,294,200
4
3
2,644
Off Market
121 Pinesbridge Road, Ossining, NY 10562
0.37
$1,683,100
4
3
4,389
Off Market
196 Pinesbridge Road, Ossining, NY 10562
0.42
$1,087,300
4
4
2,700
Off Market
50 Cloverhill Lane, Ossining, NY 10562
0.52
$2,161,800
5
4.5
5,006
Off Market
114 Pinesbridge Road, Ossining, NY 10562
0.46
$1,004,000
6
1.5
3,339
Off Market

Local Information

  • Map ViewExplore the area around 16 Overlook 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
1949
Lot Size
1.01 acres
Living Area
2,659 sqft
Price/Sqft
$454
Parking
Garage

About this House

Spectacular & Beautifully situated on over one acre of landscaped gardens, this sunny home boasts gorgeous views of Stillwater Lake, giving a year round vacation feel. Entertaining is a delight with an open eat-in kitchen, flowing into a sun-filled great room, leading out to the panoramic deck. The spacious living room/dining room with double height ceiling, wall of windows & wood burning fireplace offers another stunning option. The family room/office/potential fourth bedroom & full bath complete the first floor. The second floor provides an over sized master suite with magnificent lake views & two walk-in closets. There are two family bedrooms & a hall bath, along with a loft/office space. This hidden neighborhood has a private beach, lake privileges & ice skating, providing a fun-filled, built-in year round community. As a New Castle resident, you can park & commute from Chappaqua, along with the benefits of New Castle Rec. Convenient to multiple highways, shopping & restaurants.
16 Overlook Rd, Ossining, NY 10562 is a 3 bedroom, 3 bathroom, 2,659 sqft single-family home built in 1949. It last sold for $767,000 on Oct 2, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,207,300, with a rent estimate of $5,993/month.

Home Details for 16 Overlook Rd

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1949
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.01 acres

Price and Tax history

DateEventPrice
Oct 2, 2020
Source: OneKey® MLS as distributed by MLS GRID #H6047148
Sold
$767,000
Jul 10, 2020
Source: Agent Provided
Pending
$749,000
Jun 25, 2020
Source: Agent Provided
Listed For Sale
$749,000
Feb 5, 2020
Source: Agent Provided
ListingRemoved
$779,000
Sep 18, 2019
Source: Agent Provided
Listed For Sale
$779,000

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 16 Overlook Rd

  • What is 16 Overlook Rd estimated to be worth?
    Trulia's estimated value for 16 Overlook Rd in Ossining, NY is $1,207,300.
  • What is the price history for 16 Overlook Rd?
    16 Overlook Rd in Ossining, NY last sold for $767,000 in October 2020.
  • 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 16 Overlook Rd have air conditioning?
    Yes, 16 Overlook Rd in Ossining, NY has air conditioning.
  • Does 16 Overlook Rd have laundry facilities?
    Yes, 16 Overlook Rd in Ossining, NY has in-unit laundry.

Explore by feature - Pet Friendly

18 pet-friendly rentals in Ossining, NY

Explore by feature - Garage

10 rentals with a garage in Ossining, NY

Explore by feature - Air Conditioning

21 rentals with air conditioning in Ossining, NY

Explore by feature - Pool

8 rentals with a pool in Ossining, NY

Explore by feature - Washer/dryer

21 rentals with a washer/dryer in Ossining, NY

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 16 Overlook Rd

Skip to last item
Skip to first item

Homes for sale near 16 Overlook Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item