$329,000
Original price: $349,000
- 3 Beds
- 1.5 Baths
- 1,300 sqft
158 Rolling Way, Peekskill, NY 10566
Est. Mortgage $2,300/mo*
Get Pre-QualifiedHome Highlights
Condo
Built in 1968
$253/sqft
2 Parking Spaces
HOA $133/mo
Local Information
-- mins to
About this House
Welcome to 158 Rolling Way--a spacious and inviting condo that offers comfort and the feel of a single-family home with the ease of low-maintenance living. Enter into a bright eat-in kitchen, convenient powder room and a spacious open concept living and dining area. Sliding glass doors lead to a private deck, creating the perfect setting for morning coffee, outdoor dining, or relaxing at the end of the day. The lower level offers valuable additional space ideal for a home office, fitness area, recreation room, storage, or hobby space. Laundry is conveniently located on this level, along with direct access to a private backyard area. Upstairs, the generously sized primary bedroom is complemented by two additional bedrooms, a full bathroom and abundant closet space throughout. Conveniently located near transportation, shopping, restaurants, parks and everyday amenities, 158 Rolling Way offers comfort, versatility and convenience in one desirable package. Whether you are looking for extra space, functional living areas, or a home that can adapt to your needs, this property is ready to welcome its next owner. Schedule your private showing today!.
Last check for updates: about 23 hours ago
Listing by: RE/MAX Prestige Properties, (914) 831-3090
Maria O'Connor, (914) 980-4274
RE/MAX Prestige Properties, (914) 831-3090
Rachel F. Chason, (914) 260-9896
Source: OneKey® MLS as distributed by MLS GRID, MLS#996096

Also Listed on OneKey® MLS as distributed by MLS GRID.
Home Details for 158 Rolling Way
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Interior Details Basement: Full,Storage SpaceNumber of Rooms: 5 |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 1300 Square Feet |
Appliances & Utilities Utilities: Electricity Connected, Sewer ConnectedAppliances: Dishwasher, Dryer, Electric Oven, Electric Range, Refrigerator, WasherDishwasherDryerLaundry: In BasementRefrigeratorWasher |
Heating & Cooling Heating: Baseboard,ElectricHas CoolingAir Conditioning: Wall/Window Unit(s)Has HeatingHeating Fuel: Baseboard |
Fireplace & Spa No Fireplace |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Common Walls: 2+ Common Walls |
Levels, Entrance, & Accessibility Levels: Three Or MoreAccessibility: Accessible Hallway(s), Accessible Stairway, Stair Lift |
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Parking & Garage No CarportNo GarageParking Spaces: 2Parking: Assigned |
Frontage Road Frontage: Private RoadResponsible for Road Maintenance: Private Maintained Road |
Water & Sewer Sewer: Public Sewer |
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Cumulative Days on Market: 46Days on Market: 122 |
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Year Built Year Built: 1968 |
Property Type / Style Property Type: ResidentialProperty Subtype: Condominium, ResidentialArchitecture: Garden |
Building Construction Materials: Brick, Wood SidingAttached To Another Structure |
Property Information Parcel Number: 1200023018000010000008 |
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Price List Price: $329,000Price Per Sqft: $253 |
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MLS Status: Active |
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Direction & Address City: PeekskillCommunity: Hillcrest Park |
School Information Elementary School: HillcrestJr High / Middle School: Peekskill Middle SchoolHigh School: Peekskill High SchoolHigh School District: Peekskill |
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Listing Agent Listing ID: 996096 |
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Building Area Building Area: 1300 Square Feet |
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Not Senior Community |
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HOA Fee Includes: Common Area Maintenance, Snow Removal, TrashHOA Name: Self ManagedHas an HOAHOA Fee: $400/Quarterly |
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Lot Area: 2812 sqft |
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Special Conditions: None |
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Listing Agreement Type: Exclusive Right To Sell |
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BasementMls Number: 996096Attic: NoneAttribution Contact: 914-831-3090Showing Requirements: Appointment Only |
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HOA Amenities: Maintenance Grounds,Snow Removal,Trash |
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.
Market trends in Peekskill
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
—
Available listings
70
8MoM
Home Value
Trulia Estimate
$328KSince last month
Decreased$23K (-6.6%)Since last year
Decreased$94K (-22.3%)Since last sale
Increased$58K (+21.4%)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 +26% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $328K |
| August 2026 | $328K |
| July 2026 | $351K |
| June 2026 | $355K |
| May 2026 | $364K |
| April 2026 | $409K |
| March 2026 | $432K |
| February 2026 | $415K |
| January 2026 | $413K |
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 |
|---|---|---|---|---|---|---|---|
0.08 | Condo | $279,000 | 09/24/25 | 2 | 1 | 900 | |
0.10 | Condo | $290,000 | 01/27/26 | 2 | 1 | 900 | |
0.08 | Condo | $310,000 | 11/03/25 | 2 | 1 | 900 | |
0.22 | Condo | $264,900 | 08/05/26 | 2 | 1 | 900 | |
0.11 | Condo | $255,000 | 03/09/26 | 1 | 1 | 750 | |
0.08 | Condo | $245,000 | 09/19/25 | 1 | 1 | 697 | |
0.07 | Condo | $212,500 | 04/24/26 | 1 | 1 | 750 | |
0.10 | Condo | $229,000 | 03/11/26 | 1 | 1 | 750 | |
0.08 | Condo | $245,000 | 10/07/25 | 1 | 1 | 713 | |
0.07 | Condo | $218,000 | 11/04/25 | 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 |
|---|---|---|---|---|---|---|
0.03 | $266,400 | 2 | 1 | 900 | Off Market | |
0.06 | $454,000 | 3 | 1.5 | 2,100 | Off Market | |
0.07 | $212,500 | 1 | 1 | 750 | Recently Sold | |
0.07 | $215,100 | 1 | 1 | 700 | Off Market | |
0.07 | $295,900 | 2 | 1 | 900 | For Sale | |
0.07 | $291,100 | 2 | 1 | 900 | Off Market | |
0.07 | $248,400 | 2 | 1 | 900 | Off Market | |
0.07 | $239,900 | 1 | 1 | 700 | For Sale | |
0.07 | $232,500 | 1 | 1 | 700 | Off Market | |
0.08 | $304,200 | 2 | 1 | 900 | Off Market | |
0.08 | $299,700 | 2 | 1 | 900 | Off Market |
Price and Tax history
| Date | Event | Price |
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Aug 26, 2026 Source: OneKey® MLS as distributed by MLS GRID #996096 | PriceChange | $329,000 Price decreased by 6% |
Jun 19, 2026 Source: OneKey® MLS as distributed by MLS GRID #996096 | Pending | $349,000 |
May 8, 2026 Source: OneKey® MLS as distributed by MLS GRID #996096 | Listed For Sale | $349,000 |
Apr 14, 2005 Source: N/A | Sold | $270,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | Unavailable | $236,184 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Maria O'Connor, RE/MAX Prestige Properties, (914) 831-3090
Agent Phone: (914) 980-4274

Based on information submitted to the MLS GRID as of 2026-09-06 07:33:13 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
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Frequently asked questions about 158 Rolling Way
- What is the estimated monthly payment for 158 Rolling Way?Based on a $329,000 list price with 20% down at today's rates, the estimated monthly payment for 158 Rolling Way in Peekskill, NY is approximately $2,212 (about $1,707 principal & interest, $430 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Peekskill?Residents describe Peekskill, NY as dog-friendly, pedestrian-friendly, and walkable to restaurants. See homes for sale in Peekskill, NY.
- What are the closest schools to 158 Rolling Way?The closest schools to 158 Rolling Way in Peekskill, NY are Hillcrest School (Elementary, rated 6/10), Oakside School (Elementary, rated 3/10), Peekskill High School (rated 3/10).
- Does 158 Rolling Way have air conditioning?Yes, 158 Rolling Way in Peekskill, NY has air conditioning.
- Does 158 Rolling Way have laundry facilities?Yes, 158 Rolling Way in Peekskill, NY has in-unit laundry.
- Does 158 Rolling Way have parking?Yes, 158 Rolling Way in Peekskill, NY has on-site parking.
158 Rolling Way, Peekskill, NY 10566 is a 3 bedroom, 2 bathroom, 1,300 sqft condo built in 1968. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on May 8, 2026. The MLS # for this home is MLS# 996096.

