165 Smith St, Peekskill, NY 10566
OFF MARKET

165 Smith St
Peekskill, NY 10566

  • 3 Beds
  • 2 Baths
  • 1,578 sqft

$556,200

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,465/mo*

$556,200

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,465/mo*
3 Beds
2 Baths
1,578 sqft

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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,
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.
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Home Highlights

Parking
No Info
Outdoor
Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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 History for 165 Smith St

DatePriceEventSource
12/27/2024$590,000ListingRemovedBHHS broker feed #H6335588
12/04/2024$590,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6335588
11/08/2024$570,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6335588
12/14/2018$319,000Sold
OneKey® MLS as distributed by MLS GRID #H4832979
08/25/2018$319,000ListingRemovedAgent Provided
08/25/2018$319,000PendingAgent Provided
07/28/2018$319,000Listed For SaleAgent Provided
08/01/2005$250,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$377,193
Home facts updated by county records

Comparable Sales for 165 Smith St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.39
Multi-Family Home
$505,000
10/02/25
3
2
1,360
0.27
Multi-Family Home
$569,000
10/24/25
4
2
2,085
0.80
Multi-Family Home
$549,000
02/12/26
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
-
1.03
Multi-Family Home
$810,000
05/07/26
5
3
3,040
1.23
Multi-Family Home
$635,000
09/25/25
5
3
2,000

Assigned Schools

These are the assigned schools for 165 Smith St.
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 316 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

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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165 Smith St, Peekskill, NY 10566 is a 3 bedroom, 2 bathroom, 1,578 sqft multi-family built in 1918. This property is not currently available for sale. 165 Smith St was last sold on Dec 14, 2018 for $319,000 (46% lower than the asking price of $590,000). The current Trulia Estimate for 165 Smith St is $556,200.