165 Smith St, Peekskill, NY 10566
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Property image
OFF MARKET

165 Smith St
Peekskill, NY 10566

  • 3 Beds
  • 2 Baths
  • 1,578 sqft

$569,800

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $3,689/mo*

$569,800

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $3,689/mo*
3 Beds
2 Baths
1,578 sqft

Home Value

Trulia Estimate
$570K
Since last month
Increased$3K (+0.6%)
Since last year
Increased$30K (+5.5%)
Since last sale
Increased$252K (+79.1%)
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 +143% in the last 10 years
MonthEstimated value
2026
August 2026$571K
July 2026$569K
June 2026$568K
May 2026$558K
April 2026$549K
March 2026$548K
February 2026$540K
January 2026$537K
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
0.19
Multi-Family Home
$600,611
06/12/26
2
2
1,686
0.39
Multi-Family Home
$505,000
10/02/25
3
2
1,360
0.27
Multi-Family Home
$665,000
05/28/26
4
2
2,085
0.45
Multi-Family Home
$588,000
06/05/26
4
3
2,010
0.80
Multi-Family Home
$549,000
04/29/26
6
2
2,255
0.83
Multi-Family Home
$725,000
01/16/26
4
3
2,000
0.27
Multi-Family Home
$1,105,000
04/02/26
8
4
4,000
0.68
Multi-Family Home
$962,500
02/09/26
6
4
3,024
0.60
Multi-Family Home
$599,900
12/08/25
3
2,800
0.49
Multi-Family Home
$675,000
10/10/25
7
3
-

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
0.02
$299,999
-
-
-
For Sale
0.06
$767,600
Studio
-
2,500
Off Market
0.11
$724,800
3
2
1,921
Off Market
0.11
$531,500
2
1
940
Off Market
0.11
$894,900
6
3.5
3,425
Off Market
0.14
$517,400
3
1
1,400
Off Market
0.15
$872,500
6
4.5
3,300
Off Market
0.17
$1,077,900
7
3
4,715
Off Market
0.15
$456,300
4
2
1,500
Off Market
0.16
$706,700
3
2
2,092
Off Market
0.18
$697,800
4
2
-
Off Market
0.19
$821,200
3
2
2,688
Off Market

Local Information

  • Map ViewExplore the area around 165 Smith St.
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1918
Living Area
1,578 sqft
Price/Sqft
$361

About this House

Fantastic 2-family investment opportunity just a few blocks from downtown Peekskill, the Peekskill train station, and the scenic Hudson River. This nicely updated and well-maintained property front porch home with new composite deck offers a 2-bedroom apartment on the main level with hardwood flooring, complete with two entrances for added convenience, and a 1-bedroom apartment upstairs. Both units feature separate gas and electric meters, with tenants responsible for their own heat, electric, and hot water, making this a low-maintenance investment. Recent upgrades include a new roof, driveway, and durable vinyl siding for long-term, hassle-free upkeep. The property also includes a detached 2-car garage, currently rented at $450/month, and a small private backyard for outdoor relaxation. With easy access to bus lines, shops, and restaurants, this home offers both comfort and convenience for tenants. Security cameras are installed on the premises for added peace of mind. Don't miss this turn-key, income-generating property in the heart of Peekskill! Additional Information: ParkingFeatures:2 Car Detached,
165 Smith St, Peekskill, NY 10566 is a 3 bedroom, 2 bathroom, 1,578 sqft multi-family built in 1918. It last sold for $319,000 on Dec 14, 2018 (46% below the $590,000 asking price). It is currently off market. The Trulia Estimate is $569,800, with a rent estimate of $3,879/month.
Contact this Building

Home Details for 165 Smith St

Interior Features

Heating & Cooling
Heating: Natural GasHeating Fuel: Natural Gas
Appliances & Utilities
Cable Ready

Property Information

Year Built
Year Built: 1918
Property Type / Style
Property Type: Multi Family

Exterior Features

Exterior Home Features
DeckPatio

Price and Tax history

DateEventPrice
Dec 27, 2024
Source: BHHS broker feed #H6335588
ListingRemoved
$590,000
Dec 4, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6335588
PriceChange
$590,000
Price increased by 4%
Nov 8, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6335588
Listed For Sale
$570,000
Dec 14, 2018
Source: OneKey® MLS as distributed by MLS GRID #H4832979
Sold
$319,000
Aug 25, 2018
Source: Agent Provided
ListingRemoved
$319,000

Market trends in Peekskill

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
70
8
MoM
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Around this home

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 Peekskill

At least 317 Trulia users voted on each feature.
  • 81 % Say it's dog friendly

  • 78 % Say there are sidewalks

  • 76 % Say car is needed

  • 73 % Say it's walkable to restaurants

  • 72 % Say there's holiday spirit

  • 71 % Say yards are well-kept

  • 68 % Say parking is easy

  • 66 % Say it's walkable to grocery stores

  • 66 % Say kids play outside

  • 63 % Say people would walk alone at night

  • 61 % Say streets are well-lit

  • 59 % Say neighbors are friendly

  • 58 % Say it's quiet

  • 56 % Say there's wildlife

  • 55 % Say they plan to stay for at least 5 years

  • 47 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Alex Hudgins
    "Great commuter train service. Close to shopping very good neighborhood. Prices going up fast. Move in soon. "
  • Cassie01616
    "Some areas no sidewalks. Make sure parents speak up for kids in school and show support. Good sense of community. "
  • Alexandercolby
    "This neighborhood is idyllic. Wonderful diversity of cultures mixing together with appreciation of differences and and understanding of sameness. So much to do, and such a great place to raise a family. You can't beat the commute; a beautiful ride up the Hudson on the Metro-north and you're well away from the din and dirt of the city. Or if you need a little culture, you're in the heart of Manhattan in under an hour. Moving here was the best decision. "
  • Lindsay
    "I’ve lived here for 1 year. It’s a very dog friendly community and everyone speaks in the neighborhood which is very welcoming. "
  • Diann.egan1@gmail.com
    "Great dining, beautiful area parks, well maintained homes, beautiful water front, farmers markets, nice neighborhoods. "
  • Nicole P.
    "I drive, traffic isn’t terrible. Summer there is less traffic on 9 to Ossining. When school is in session traffic tends to be worse."
  • Rachel S.
    "There is so much to do in this town! It has hikes, shops, amazing restaurants, and the beautiful waterfront. "
  • Alan A. S. J.
    "It’s a short drive from my apt to my job. It’s a 10 min drive or a 45 min walk of I couldn’t drive for any reason"
  • Willartiles12
    "Very quite area, extremely diverse by having all sorts of different race and color. People are very friendly and helpful in Peekskill "
  • Millie P.
    "Very diverse neighborhood and local grocery stores and restaurants are within walking distance. Beautiful view by the water front and amazing sunsets. Metro north train that takes you straight into the city."
  • Nvrltgo
    "Very easy to get to the train and restaurants are amazing the ppl are nice very family friendly and helpful neighbors cab service very fast and reliable "
  • Millie P.
    "Very Diverse group of people and within walking distance to local stores. Family friendly local people and within walking distance to the water front."
  • Johnathan M.
    "The overall commute is fair but if you have a vehicle it’s great. The beeline and metro north are easily accessible. Their schedules are usually spot on and rarely ever any delays. "
  • David G.
    "I lived here now for the past three years. My neighbors are extremely friendly and we all help each other out and get along with each other."
  • Mark B.
    "They do a great job with the Peekskill waterfront events and great restaurants in downtown Peekskill. "
  • Jeanee T.
    "Central location, close to everything. My job is literally a 5 minute walk or a minute drive, with a great coffee house to grab a quick cup on the way into the office "
  • Adesai
    "I use public transportation to commute to work. Number 17 express bus to white plains is only an hour and cost 2.75/trip"
  • Marie M.
    "It’s so friendly, has an art community, has character and stunning views of the best part of the Hudson River. "
  • Roxana R.
    "It’s still in good prices for rent and yes have very nice parks areas, its getting better than years ago. "
  • Mary L. C.
    "A lot of Landlords don’t accept pets so it’s hard to find a decent apartment that allows you to have dogs"
  • Leslie F.
    "I enjoy the diverse restaurants and activities brought by the restaurants owners. It’s a wonderful place to leave and raise a family. "
  • Leslie F.
    "Unfortunately work doesn’t allow me to know what activities my community has to offer. Maybe soon I’ll look into this "
  • Ralph E.
    "keeping the focus on our prized possessions, our young. create programs that help mold the future of our country, at an early age. Nurture them, in all phases of development.. Integrate using an intelligent approach, which will allow our future to reach their maximum potential. "
  • Trulia User
    "Great community and awesome activities for family. Schools are good. Environment is safe. I will recommend Peekskill "
  • MRL
    "Tons of fun riverfront events, movies, art galleries and shows, coffeehouse music, church activities. "
  • jack
    "Great and safe neighborhood. Quiet and very respectful people. Not in all areas like that but certainly up here on mortgage hill."
  • Ashanty1025
    "i’ve lived in this neighborhood for two years it good. People are really friendly around here and it’s a well maintained city "
  • Alamopaula
    "The education is good for all grades and people are friendly. People look after them selfs. Most things are in walking distance from wherever you live in Peekskill. Everyone knows everyone it’s a small world/town. Most busiest part of peekskill is downtown/Main Street. "
  • Sarah H.
    "very dog friendly! lots of places to take them out between dog parks and hiking trails and the riverfront "
  • Chris B.
    "block party in the center of town. Surrounded by bars and restaurants that give nightlife to this town0"

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Homes for sale near 165 Smith St

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Off Market Homes Near 165 Smith St

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Frequently asked questions about 165 Smith St

  • What is 165 Smith St estimated to be worth?
    Trulia's estimated value for 165 Smith St in Peekskill, NY is $569,800.
  • What is the price history for 165 Smith St?
    165 Smith St in Peekskill, NY last sold for $319,000 in December 2018.
  • Is Peekskill a buyer's or seller's market?
    Peekskill is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Peekskill?
    Residents describe Peekskill, NY as dog-friendly, pedestrian-friendly, and walkable to restaurants. See recently sold homes in Peekskill, NY.