For sale

$329,000

Est. $2,474/mo —

•

1,300

sq ft

158 Rolling Way, Peekskill, NY 10566

About this home

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!.

CondoProperty Type

1968Year Built

2,812 sq ftLot Size

$253Price/Sq.Ft.

$133/moHOA Dues

2 spacesParking

Listing by Maria O'Connor • RE/MAX Prestige Properties

Listing by Rachel Chason • RE/MAX Prestige Properties

Contact: 914-831-3090

Listing updated: Aug 31, 2026 at 09:41am

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #996096

Payment calculator

$2,474 per month

Principal and interest$1,729

Property taxes

HOA dues

Home insurance

Utilities

5 minutes to get started. No credit impact.

Affordability tools

See this home in person

Open houses

No upcoming open houses.

Nearby open houses (6)

OPEN FRI, 5PM TO 7PM
$85,000
2 beds2 baths980 sq ft
9 Rivercrest Rd #22, Highland Falls, NY 10928
Listing by Howard Hanna Rand Realty
OPEN SAT, 12PM TO 2PM
$889,000
4 beds3.5 baths2,400 sq ft
3123 Douglas Dr, Yorktown Heights, NY 10598
Listing by Weichert Realtor Future Vision
OPEN SAT, 12PM TO 2PM
$1,499,000
5 beds3.5 baths3,300 sq ft
240 Mahopac Ave, Somers, NY 10598
Listing by Coldwell Banker Realty
OPEN SAT, 1PM TO 3PM
$650,000
3 beds2 baths2,057 sq ft
28 Pike Pl, Mahopac, NY 10541
Listing by Call it Closed Intl. Realty
OPEN SUN, 11AM TO 1PM
$425,000
2 beds2 baths1,200 sq ft
10 Edinburgh Dr #10, Peekskill, NY 10566
Listing by Real Broker NY LLC
OPEN SUN, 12PM TO 2PM
$600,000
3 beds2 baths1,503 sq ft
31 N 2nd St, Cortlandt Manor, NY 10567
Listing by BHHS Hudson Valley Properties

Around this home

Schools

K - 12
Preschool & daycare

Hillcrest School

Public 3-5 • Assigned • 0.3mi

6/10

Peekskill Middle School

Public 6-8 • Assigned • 1.1mi

3/10

Peekskill High School

Public 9-12 • Assigned • 0.9mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

158 Rolling Way · $329,000

Strong offer

$329K and above

75% chance or better to win

Why $329K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 36 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
First-floor bedroom and first-floor full bath
Accessible hallways and stairway
Stair lift installed
Three or more levels
Basement with storage space

Bedrooms
Bedroom on the first floor

Bathrooms
One full bathroom
One half bathroom

Kitchen
Dishwasher
Electric range/oven
Refrigerator

Laundry & utility
Washer and dryer
Laundry located in the basement

Heating & cooling
Baseboard heating (electric)
Wall/window air conditioning units

Sale and tax history for 158 Rolling Way

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2026

$5,349 (+1.2%)

$1,300 + $4,085

$5,385

2025

$5,286 (+7.7%)

$1,300 + $4,085

$5,385

2024

$4,907 (+2.1%)

$1,300 + $4,085

$5,385

2023

$4,808 (+1.5%)

$1,300 + $4,085

$5,385

2022

$4,737 (−25.1%)

$1,300 + $4,085

$5,385

2021

$6,327 (+52.7%)

$1,300 + $4,085

$5,385

2020

$4,144 (+5.5%)

$1,300 + $4,085

$5,385

2019

$3,928

$1,300 + $4,085

$5,385

2018

$1,300 + $4,085

$5,385

2017

$1,300 + $4,085

$5,385

2016

$1,300 + $4,085

$5,385

2014

$1,300 + $4,085

$5,385

2013

$1,300 + $4,085

$5,385

2012

$1,300 + $5,517

$6,817

2011

$1,300 + $5,517

$6,817

2010

$1,300 + $5,517

$6,817

2009

$1,300 + $5,517

$6,817

2008

$1,300 + $5,517

$6,817

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

—

Lot width

20 ft.

Lot depth

120 ft.

Lot size

2,809 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Westchester County

APN

551200A02301800010080000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

R - 4

Low-Density Multiple Residence District

These districts are designed to provide for all types of residential buildings in order to permit a broad range of housing types, with appropriate standards for each district on density, open space and spacing of buildings. The various districts are mapped in relation to a desirable future residential density pattern with emphasis upon accessibility to transportation facilities and to various community facilities and upon the character of existing development. These districts also include community facilities and open uses which serve residents of these districts or are benefited by an open residential character.

Permitted uses

Include but are not limited to:

Agriculture
Greenhouse / nursery
Housing-Single unit
Housing-Multiple units
Public service
Recreation
Park & open space

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.62% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 99° expected this year, 15 days in 30 years

4/10 Wind Factor

19% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Peekskill, NY • 10566

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

87/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Peekskill. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.6 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 158 Rolling Way

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $360,000 and $579,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $360K to $579K.

SOLD AUG 27, 2026
$513,000 Last sold price
2 beds3.5 baths1,530 sq ft
6 Clara Ct, Cortlandt Manor, NY 10567
Listing by Island Advantage Realty LLC
$82/sq ft
smaller lot
20 years newer
SOLD AUG 4, 2026
$578,000 Last sold price
3 beds2 baths1,600 sq ft
200 Husted Ave, Peekskill, NY 10566
Listing by HomeSmart Homes & Estates
$108/sq ft
larger lot
45 years older
SOLD AUG 14, 2026
$579,000 Last sold price
3 beds2 baths1,200 sq ft
4 Buena Vista Ave, Peekskill, NY 10566
Listing by American Family Realty
$230/sq ft
larger lot
4 years older
SOLD DEC 12, 2025
$425,000 Last sold price
2 beds1 bath864 sq ft
809 Oakwood Dr, Peekskill, NY 10566
Listing by Gary Sanguino
$239/sq ft
larger lot
18 years older
SOLD MAY 22, 2026
$559,000 Last sold price
3 beds2 baths1,248 sq ft
964 Pemart Ave, Peekskill, NY 10566
Listing by Houlihan Lawrence Inc.
$195/sq ft
larger lot
20 years older
SOLD APR 16, 2026
$360,000 Last sold price
3 beds1 bath840 sq ft
1716A Main St, Peekskill, NY 10566
Listing by Alliance RE Consultants, LLC
$176/sq ft
larger lot
11 years older

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