165 Chappaqua Rd, Ossining, NY 10562
Property image
Property image
OFF MARKET

165 Chappaqua Rd
Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 1,340 sqft (on 0.83 acres)

$898,300

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $5,736/mo*
Refinance Your Home

$898,300

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $5,736/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,340 sqft
(on 0.83 acres)

Local Information

  • Map ViewExplore the area around 165 Chappaqua Rd.
  • Schools1 Preschool School4 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Located in beautiful Briarcliff Manor and set back on almost one acre sits this pristine ranch style property. This home is turn-key offering a beautifully updated kitchen with granite counters, SS appliances, and custom cabinetry that opens to a formal dining room with sliding glass doors to an expansive deck overlooking a serene park-like property. The formal living room with vaulted ceiling, skylights, and a beautiful stone fireplace provides a comfortable, open, and bright setting. At the end of the hall is the master bedroom with an en-suite bath. Two additional bedrooms and an updated hall bath complete the main floor. A few steps down is a welcoming recreation room with a pellet stove, bathroom, large cedar closet, laundry room, and a door to the two-car garage. The 575 SF Basement is not included in the square footage. Easy commute to NYC, close to train and major routes. Minutes to shops & restaurants and a short walk to parks. Taxes are before STAR rebate of $2,144.
165 Chappaqua Rd, Ossining, NY 10562 is a 3 bedroom, 3 bathroom, 1,340 sqft single-family home built in 1980. It last sold for $585,000 on Aug 20, 2020. It is currently off market. The Trulia Estimate is $898,300, with a rent estimate of $5,066/month.

Home Highlights

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

Home Details for 165 Chappaqua Rd

Interior Features

Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 5
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Exterior Features

Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.83 acres

Price History for 165 Chappaqua Rd

DatePriceEventSource
08/20/2020$585,000Sold
N/A
05/30/2020$615,000Listed For SaleAgent Provided

Market trends in Briarcliff Manor

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
35
4MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$779,200
Home facts updated by county records

Comparable Sales for 165 Chappaqua Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
175 Chappaqua Road, Briarcliff Manor, NY
0.07
Single-Family Home
$808,500
12/26/25
3
2.5
2,280
9 Studio Hill Rd, Ossining, NY
0.25
Single-Family Home
$828,000
07/21/25
3
2
1,744
9 Studio Hill Road, Briarcliff Manor, NY
0.25
Single-Family Home
$828,000
07/11/25
3
2
1,796
21 Tappan Terrace, Briarcliff Manor, NY
0.32
Single-Family Home
$747,000
10/15/25
3
2.5
1,385
17 Ridgeview Dr, Ossining, NY
0.20
Single-Family Home
$670,000
09/05/25
2
1
1,854
25 Tappan Terrace, Briarcliff Manor, NY
0.36
Single-Family Home
$577,500
08/07/25
3
2
1,673
74 Hungerford Road, Briarcliff Manor, NY
0.33
Single-Family Home
$925,000
07/02/26
3
2
2,056
6 Leawood Drive, Briarcliff Manor, NY
0.36
Single-Family Home
$625,000
12/22/25
3
2
1,541
19 Donald Lane, Ossining, NY
0.43
Single-Family Home
$675,000
03/26/26
3
1.5
1,408
43 Ganung Drive, Ossining, NY
0.58
Single-Family Home
$850,000
07/11/25
3
2
1,767

Nearby homes

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Assigned Schools

These are the assigned schools for 165 Chappaqua 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 Briarcliff Manor

At least 67 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 88 % Say parking is easy

  • 86 % Say car is needed

  • 83 % Say there's holiday spirit

  • 82 % Say it's quiet

  • 76 % Say yards are well-kept

  • 72 % Say people would walk alone at night

  • 71 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 63 % Say kids play outside

  • 60 % Say neighbors are friendly

  • 56 % Say there are community events

  • 54 % Say it's walkable to restaurants

  • 51 % Say it's walkable to grocery stores

  • 42 % Say streets are well-lit

  • 40 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Bill Richards
    "We all have dogs so it’s all about the dogs. There are plenty of parks as well. A great place to live overall. "
    0
    Flag
  • Adrianna M.
    "It’s a beautiful community with a small town feel. I would highly recommend someone moving here! It’s a great community and you feel very safe within it. "
    4
    Flag
  • Annemarie
    "I grew up in Briarcliff. It’s a pretty quiet neighborhood where I’ve always felt safe, and there seem to be more and more young families moving into the area. At least in my area, a car is definitely needed to get around—no public transit options nearby. For parents considering moving to Briarcliff and looking at the public schools, note that parts of Briarcliff are within the neighboring town (Ossining) school district."
    12
    Flag
  • Whaidjrs
    "Metro North Train Station gets me to Grand Central in 45 minutes. Comfortable affordable ride to work in Midtown Manhattan. "
    0
    Flag
  • FlowerPower
    "Lack of sidewalks and rare street lights makes walk uncomfortable during dark times. The Rockefeller State Park being such a ‘gem’ for dog walks is so close!"
    10
    Flag
  • Eleanor B.
    "Croton aqueduct North county trail Rockefeller state park Hudson River views Safe neighborhood Quiet and peaceful "
    0
    Flag
  • Charly-ann O.
    "Very dog friendly community. Lots of parks and a beautiful river walk where people bring their dogs. "
    1
    Flag
  • Ossining Resident
    "Ossining is a beautifully diverse community with lots of lovely parks, a vibrant Main Street, and a fantastic waterfront. We’ve lived here for 15 years and wouldn’t want to raise our children anywhere else. "
    3
    Flag
  • Monicacmandek
    "Beautiful area, but very limited diversity. There’s two sides to town. 9A divides them. One side is uber wealthy, the other side is dual income families. I lived on the working family side for 29 years. "
    0
    Flag
  • Lyn1103
    "Amazing place to live. Everyone is so friendly. I love how there are many different races here. Everyone is very accepting and kind. This is great place to live"
    6
    Flag
  • Bobohanlon
    "In the Rockwell Era neighbor, most neighbors are friendly and there when you need them. Its a good family neighborhood with lots of kids of all ages "
    1
    Flag
  • cookingforkidswithjim
    "amazing place it is located in beautiful Hudson Valley with lots of woods and friendly rich people"
    4
    Flag
  • rosarioladuca
    "A real community of people that care about one another."
    0
    Flag
  • miotto4home
    "This area in the town of Ossining (unincorporated) has the best of both worlds. Quiet neighborhoods with great safety and yards for young families and accessibility to all major highways within minutes. Up and coming schools and great parks. Wish I could return but our job took our family out of the area a few years back."
    0
    Flag
  • Lvanporter
    "Family neighborhood, no thru street, all houses in good condition."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Pool

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Homes for sale near 165 Chappaqua Rd

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Off Market Homes Near 165 Chappaqua Rd

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