165 Smith St
Peekskill, NY 10566
- 3 Beds
- 2 Baths
- 1,578 sqft
3 Beds
2 Baths
1,578 sqft
Home Value
Trulia Estimate
$570KSince 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
| Month | Estimated 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
-- mins to
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
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Heating & Cooling Heating: Natural GasHeating Fuel: Natural Gas |
Appliances & Utilities Cable Ready |
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Year Built Year Built: 1918 |
Property Type / Style Property Type: Multi Family |
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Exterior Home Features DeckPatio |
Price and Tax history
| Date | Event | Price |
|---|---|---|
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 |
Aug 25, 2018 Source: Agent Provided | Pending | $319,000 |
Jul 28, 2018 Source: Agent Provided | Listed For Sale | $319,000 |
Aug 1, 2005 Source: N/A | Sold | $250,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | Unavailable | $377,193 |
Home facts updated by county records
Market trends in Peekskill
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
70
8MoM
Around this home
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.
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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.

