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

$1,385,400

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 4,200 sqft (on 2 acres)

50 Overlook Rd, Ossining, NY 10562

Est. Refi. Payment $9,232/mo*
Refinance Your Home
Currently Off Market - Sold Sep 29, 2000 for $465,000

Home Value

Trulia Estimate
$1.39M
Since last month
Increased$30K (+2.2%)
Since last year
Increased$206K (+17.5%)
Since last sale
Increased$920K (+197.9%)
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 +93% in the last 10 years
MonthEstimated value
2026
September 2026$1.39M
August 2026$1.37M
July 2026$1.36M
June 2026$1.37M
May 2026$1.34M
April 2026$1.3M
March 2026$1.23M
February 2026$1.21M
January 2026$1.16M
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
83 McDonald Road, Ossining, NY
0.26
Single-Family Home
$1,075,000
10/15/25
5
3
3,972
352 Croton Dam Road, Ossining, NY
0.61
Single-Family Home
$1,450,000
08/19/26
4
3.5
4,290
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
0.39
Single-Family Home
$721,000
02/27/26
3
2
1,528
1364 Spring Valley Road, Ossining, NY
0.74
Single-Family Home
$950,000
03/05/26
3
2.5
2,424
6 Ichabod Lane, Ossining, NY
0.61
Single-Family Home
$875,000
03/09/26
3
2.5
2,030
18 Adams Road, Ossining, NY
0.57
Single-Family Home
$816,000
04/22/26
3
2
1,658
320 Illington Road, Ossining, NY
1.02
Single-Family Home
$1,025,000
03/23/26
4
3
2,950
1376 Spring Valley Road, Ossining, NY
0.65
Single-Family Home
$999,000
01/20/26
3
2.5
2,242

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
50 Cloverhill Lane, Ossining, NY 10562
0.17
$2,091,500
5
4.5
5,006
Off Market
83 McDonald Road, Ossining, NY 10562
0.26
$1,156,800
5
3
3,972
Off Market
3 Lake Way, Ossining, NY 10562
0.25
$872,600
2
2.5
1,940
Off Market
1340 Kitchawan Road, Ossining, NY 10562
0.29
$1,117,500
8
6.5
6,500
Off Market
55 Hoags Cross Road, Ossining, NY 10562
0.28
$865,000
3
2
2,292
Recently Sold
56 Twin Ridges Road, Ossining, NY 10562
0.29
$1,271,900
3
3.5
3,679
Off Market
4 Lake Way, Ossining, NY 10562
0.31
$1,372,800
3
2.5
2,732
Off Market
9 Possum Road, Ossining, NY 10562
0.39
$721,000
3
2
1,528
Recently Sold
1305 Grants Lane, Ossining, NY 10562
0.56
$750,000
2
1
1,469
Recently Sold
10 Lakeview Road, Ossining, NY 10562
0.54
$715,000
3
2.5
2,270
Recently Sold
18 Adams Road, Ossining, NY 10562
0.57
$816,000
3
2
1,658
Recently Sold
166 Pinesbridge Road, Ossining, NY 10562
0.55
$943,900
3
2.5
1,598
Off Market

Local Information

  • Map ViewExplore the area around 50 Overlook Rd.
  • Schools1 Preschool School4 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
2 acre lot
4,200 sqft
$330/sqft
Garage

About this House

Gerald Luss, architect of this home where he lived with his family, is best known for his influence on large-scale corporate projects during the unprecedented post–World War II building boom in Manhattan, although his work can be found around the world. He is particularly noted for the innovations he developed for the interiors of the famed Time-Life office building (1959) on Avenue of the Americas in midtown Manhattan – the epitome of midcentury modern skyscraper design in which Time-Life occupied 350,000 square feet of space for its headquarters, commonly recognized today as the backdrop to AMC’s Mad Men series.


50 Overlook Rd, Ossining, NY 10562 is a 5 bedroom, 4 bathroom, 4,200 sqft single-family home built in 1955. It last sold for $465,000 on Sep 29, 2000. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,385,400, with a rent estimate of $7,584/month.

Home Details for 50 Overlook Rd

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Family Room, Laundry Room, Master Bath, Workshop
Heating & Cooling
Heating: Forced Air, Radiant, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Stone, Wood, Cement ConcreteLawn
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Sep 29, 2000
Source: N/A
Sold
$465,000

Market trends in Ossining

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
54
6MoM

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 50 Overlook Rd

  • What is 50 Overlook Rd estimated to be worth?
    Trulia's estimated value for 50 Overlook Rd in Ossining, NY is $1,385,400.
  • What is the price history for 50 Overlook Rd?
    50 Overlook Rd in Ossining, NY last sold for $465,000 in September 2000.
  • 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 50 Overlook Rd have air conditioning?
    Yes, 50 Overlook Rd in Ossining, NY has air conditioning.
  • Does 50 Overlook Rd have laundry facilities?
    Yes, 50 Overlook Rd in Ossining, NY has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 50 Overlook Rd

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