16 Overlook Rd, Ossining, NY 10562
OFF MARKET

16 Overlook Rd
Ossining, NY 10562

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

$1,149,900

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $7,166/mo*
Refinance Your Home

$1,149,900

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $7,166/mo*
Refinance Your Home
3 Beds
3 Baths
2,659 sqft
(on 1.01 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 16 Overlook Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Other, OtherAir 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 History for 16 Overlook Rd

DatePriceEventSource
10/02/2020$767,000Sold
OneKey® MLS as distributed by MLS GRID #H6047148
07/10/2020$749,000PendingAgent Provided
06/25/2020$749,000Listed For SaleAgent Provided
02/05/2020$779,000ListingRemovedAgent Provided
09/18/2019$779,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax
Assessment$145,000
Home facts updated by county records

Comparable Sales for 16 Overlook Rd

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
9 Possum Road, Ossining, NY
0.58
Single-Family Home
$721,000
02/27/26
3
2
1,528
25 Highview Road, Ossining, NY
0.87
Single-Family Home
$827,000
07/03/25
4
2.5
2,460
18 Adams Road, Ossining, NY
0.66
Single-Family Home
$816,000
04/22/26
3
2
1,658
196 Pinesbridge Road, Ossining, NY
0.42
Single-Family Home
$999,000
07/16/25
4
4
2,700
83 McDonald Road, Ossining, NY
0.52
Single-Family Home
$1,075,000
10/15/25
5
3
3,972
90 Shingle House Road, Millwood, NY
0.87
Single-Family Home
$850,000
09/12/25
4
3
2,318
83 Inningwood Road, Millwood, NY
0.83
Single-Family Home
$1,090,000
10/15/25
4
2
1,874
16 Gregory Lane, Millwood, NY
1.02
Single-Family Home
$1,200,000
07/31/25
4
2.5
2,251
58 Hidden Hollow Lane, Millwood, NY
0.98
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 16 Overlook 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 370 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
    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."
    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
    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

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16 Overlook Rd, Ossining, NY 10562 is a 3 bedroom, 3 bathroom, 2,659 sqft single-family home built in 1949. This property is not currently available for sale. 16 Overlook Rd was last sold on Oct 2, 2020 for $767,000. The current Trulia Estimate for 16 Overlook Rd is $1,149,900.