5 Rolling Way, Peekskill, NY 10566
OFF MARKET

5 Rolling Way
Peekskill, NY 10566

  • 2 Beds
  • 1 Bath
  • 900 sqft

$294,800

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $1,944/mo*

$294,800

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $1,944/mo*
2 Beds
1 Bath
900 sqft

Home Value

Trulia Estimate
$295K
Since last month
Increased$500 (+0.2%)
Since last year
Increased$11K (+3.8%)
Since last sale
Increased$35K (+13.4%)
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 +27% in the last 10 years
MonthEstimated value
2026
August 2026$295K
July 2026$296K
June 2026$294K
May 2026$292K
April 2026$287K
March 2026$290K
February 2026$286K
January 2026$283K
2025
2024
2023

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
0.03
Condo
$290,000
01/27/26
2
1
900
0.05
Condo
$279,000
09/24/25
2
1
900
0.22
Condo
$264,900
08/05/26
2
1
900
0.00
Condo
$255,000
03/09/26
1
1
750
0.03
Condo
$229,000
03/11/26
1
1
750
0.04
Condo
$245,500
09/03/25
1
1
700
0.04
Condo
$245,000
09/19/25
1
1
697
0.04
Condo
$240,000
09/03/25
1
1
700
0.05
Condo
$212,500
04/24/26
1
1
750
0.22
Condo
$230,000
06/26/26
1
1
700

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
0.04
$348,600
2
1
900
Off Market
0.04
$342,100
2
1
900
Off Market
0.04
$259,800
1
1
713
Off Market
0.04
$246,900
2
1
900
Off Market
0.04
$353,600
2
1
900
Off Market
0.04
$261,100
1
1
713
Off Market
0.04
$255,000
1
1
700
Off Market
0.04
$258,800
1
1
697
Off Market
0.04
$260,800
1
1
700
Off Market
0.04
$310,000
2
1
900
Recently Sold
0.04
$341,000
2
1
900
Off Market
0.05
$298,900
2
1
900
Off Market

Local Information

  • Map ViewExplore the area around 5 Rolling Way.
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1965
Living Area
900 sqft
Price/Sqft
$328
Parking
1 Parking Spaces
HOA
$723/Monthly

About this House

MOVE-in-READY !!! Welcome to this pristine just renovate 2 Bedroom Condo. The updated Kitchen offers new cabinetry, an elegant granite counter ,new stainless steel appliances. The dining area gives access to a balcony. The living Room is spacious and bright as well as the primary and second bedroom. Newer Bath, new hardwood floors, ample closet space, makes this the place you have been waiting for.
Laundry room on premises.
Peekskill has a lot to offer, proximity to shops, Schools, Houses of Worship, Metro North, major highways and last but not least the beautiful Hudson Riverfront Park. Additional Information: HeatingFuel:Oil Above Ground,
5 Rolling Way, Peekskill, NY 10566 is a 2 bedroom, 1 bathroom, 900 sqft condo built in 1965. It last sold for $259,900 on May 21, 2024 (4% below the $269,900 asking price). It is currently off market. The Trulia Estimate is $294,800, with a rent estimate of $2,716/month.

Home Details for 5 Rolling Way

Interior Features

Interior Details
Number of Rooms: 5
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 900 Square Feet
Appliances & Utilities
Utilities: Trash Collection PrivateAppliances: Microwave, Refrigerator, Oil Water HeaterLaundry: Common AreaMicrowaveRefrigerator
Heating & Cooling
Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Wall/Window Unit(s)Has HeatingHeating Fuel: Baseboard
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Hardwood

Exterior Features

Parking & Garage
No CarportParking Spaces: 1Parking: Assigned,Unassigned
Pool
Pool: Community, In Ground
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1965Year Renovated: 2023
Property Type / Style
Property Type: ResidentialProperty Subtype: Condominium, ResidentialArchitecture: Garden
Building
Construction Materials: Brick, Wood SidingAttached To Another Structure
Property Information
Included in Sale: Light Fixtures, Oven/RangeParcel Number: 120002301800001000006005M

Price & Status

Price
List Price: $269,900
Status Change & Dates
Off Market Date: Tue Feb 20 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: PeekskillCommunity: Hillcrest Park
School Information
Jr High / Middle School: Peekskill Middle SchoolHigh School: Peekskill High SchoolHigh School District: Peekskill

Building

Building Area
Building Area: 900 Square Feet

Community

Community Features: Park, PoolNot Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Maintenance Structure, Heat, Hot Water, Other, Sewer, Snow Removal, Trash, WaterHOA Name: Ferrara ManagementHas an HOAHOA Fee: $723/Monthly

Lot Information

Lot Area: 39 sqft

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

Mls Number: H6285173Attic: NoneAttribution Contact: (914) 962-4900Showing Requirements: Combination Lock Box

Additional Information

HOA Amenities: Park,Trash
Last check for updates: about 9 hours ago
Listed by Margherita Eccleston, (914) 525-8945
Houlihan Lawrence Inc., (914) 962-4900
Bought with: Carolyn Michelle, (845) 546-8388, Keller Williams Realty Partner, (914) 962-0007
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6285173

Price and Tax history

DateEventPrice
May 21, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6285173
Sold
$259,900
Feb 20, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6285173
Pending
$269,900
Jan 19, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6285173
Listed For Sale
$269,900
May 27, 2014
Source: Agent Provided
ListingRemoved
$99,000
May 22, 2014
Source: Agent Provided
Listed For Sale
$99,000

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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Frequently asked questions about 5 Rolling Way

  • What is 5 Rolling Way estimated to be worth?
    Trulia's estimated value for 5 Rolling Way in Peekskill, NY is $294,800.
  • What is the price history for 5 Rolling Way?
    5 Rolling Way in Peekskill, NY last sold for $259,900 in May 2024.
  • 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.
  • Does 5 Rolling Way have air conditioning?
    Yes, 5 Rolling Way in Peekskill, NY has air conditioning.
  • Does 5 Rolling Way have a pool?
    Yes, 5 Rolling Way in Peekskill, NY has a pool.
Based on information submitted to the MLS GRID as of 2026-08-14 00:23:10 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information