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$349,000

  • For Sale
  • Active
  • Condo
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • Updated 3 days ago

Next open house:

Open House: 11:30 AM - 1:00 PM

Saturday 5/16 11:30 AM - 1:00 PM

158 Rolling Way,Peekskill, NY 10566

158 Rolling WayPeekskillNY10566

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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!.

Full Property Details for 158 Rolling Way

General

  • Price: $349,000
  • HOA FEE: $133/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $6,724
  • Status: Active
  • Type: Condo
  • Source: Long_Island
  • MLS ID: 996096
  • Updated: 5/11/2026
  • Added to Site: 7 day(s) ago

Interior

  • Number of Rooms: 5
  • Interior Features: First Floor Bedroom, First Floor Full Bath
  • Appliances: Dishwasher, Dryer, Electric Oven, Electric Range, Refrigerator, Washer
  • Laundry Facilities: Yes

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Basement

Additional Information

  • Shared Amenities: Maintenance Grounds, Pool, Snow Removal, Trash

Parking

  • Total Spaces: 2
  • Parking Features: Assigned
  • Assigned Parking: Yes

Location

  • County: Westchester County
  • Subdivision: Hillcrest Park

School Information

  • High School District: Peekskill
  • Elementary School: Hillcrest
  • Middle School: Peekskill Middle School
  • High School: Peekskill High School

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Maintenance, Snow Removal, Trash
  • Pets Allowed: Yes
  • Pet Restrictions: Yes

Heating & Cooling

  • Cooling Type: Wall/Window Unit(s)
  • Heating Type: Baseboard, Electric
  • Heating Zones: 1

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Sewer Connected

Structural Information

  • Architectural Style: Garden
  • Detached/Attached: Attached
  • Construction: Brick, Wood Siding
  • Basement: Yes
  • Basement Desc.: Full Basement, Storage Space
  • Common Walls: 2+ Common Walls
  • Entry Floor Number: 1
  • Sq. Ft. Source: Other
  • Year Built: 1968

Lot Features

  • Lot Size (Acres): 0.0646
  • Lot Size (Sq. Ft.): 2,812
  • Frontage: Private Road
  • Road Maintenance: Private Maintained Road

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $400
  • Assoc Fee Freq.: Quarterly
  • Taxes Include: Sewer, Trash
  • Tax Amount: $6,724

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 1200-023-018-00001-000-0008

Listed by RE/MAX Prestige Properties

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Listing agents

— 158 Rolling Way —

  • RE/MAX Prestige Properties

  • RE/MAX Prestige Properties

914-831-3090

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with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 158 Rolling Way

School District:Peekskill City School District
NameGradesDistance
Hillcrest School
4 Horton Drive, Peekskill, NY 10566
4-50.3 mi
Oakside School
200 Decatur Avenue, Peekskill, NY 10566
1-30.8 mi
Woodside School
Depew Street, Peekskill, NY 10566
K-11.2 mi
Peekskill Middle School
212 Ringgold Street, Peekskill, NY 10566
6-81.1 mi
Peekskill High School
1072 Elm Street, Peekskill, NY 10566
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 158 Rolling Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/08/2026
Listed
$349,000
29.26%
MLS
3/14/2005
Sold
$270,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 158 Rolling Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,724
100%
$5,385
—
2024
100%
$5,385
—
2020
-100%
$5,385
—
2020
$4,144
19%
$5,385
—
2018
$3,468
4%
$5,385
—
2017
$3,340
7%
$5,385
—
2017
$3,127
-44%
$5,385
—
2016
$5,588
64%
$5,385
—
2015
$3,411
-37%
$5,385
—
2014
$5,426
—
$5,385
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 158 Rolling Way

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by RE/MAX Prestige Properties

158 Rolling Way, Peekskill, NY 10566 (MLS# 996096) is a Condo property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 158 Rolling Way is currently listed for $349,000 and was received on May 08, 2026. Want to learn more about 158 Rolling Way? Do you have questions about finding other Condo real estate for sale in Peekskill? You can browse all Peekskill real estate or contact a Coldwell Banker agent to request more information.

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