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158 Rolling WayPeekskill, NY 10566

For Sale

$329,000

Smart Buyer Rebate - Ask

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!.

Listed by Maria O'Connor

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RE/MAX Prestige Properties

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914-831-3090

Listed by Rachel F. Chason

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RE/MAX Prestige Properties

Last updated September 12, 2026

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Source: OneKey #996096

Listing Facts

  • TypeCondo
  • NeighborhoodPeekskill
  • Bedrooms3
  • Bathrooms2
  • Days on Prevu130
  • HOA/Maint. Fees$400/quarter
  • Taxes$6,724/year
  • Size1,300 sqft
  • Price per sqft$253

Amenities

  • Dishwasher
  • Washer/Dryer
  • Pets Allowed
  • Parking

Location

Mortgage Calculator

Listing History

08/26/2026
Status changed to Active
$329,000
08/26/2026
Price Decreased
$329,000
06/19/2026
Status changed to Pending
$349,000
05/08/2026
Listed by RE/MAX Prestige Properties
$349,000
  1. 08/26/2026$329,000
    Status changed to Active
  2. 08/26/2026$329,000
    Price Decreased
  3. 06/19/2026$349,000
    Status changed to Pending
  4. 05/08/2026$349,000
    Listed by RE/MAX Prestige Properties

Property Details for 158 Rolling Way

Association

Amenities

  • Association Amenities: Maintenance Grounds, Snow Removal, Trash
  • Pets Allowed: Yes

Fees

  • Association Fee: $400.00 Quarterly
  • Association Fee Includes: Common Area Maintenance, Snow Removal, Trash

Financial

  • Renting Allowed: Yes

General

  • Association Name: Self Managed

Exterior

Construction

  • Property Attached: Yes
  • Structure Type: Townhouse
  • Year Built: 1968
  • Architectural Style: Garden
  • Common Walls: 2+ Common Walls
  • Construction Materials: Brick, Wood Siding
  • Entry Level: 1

Features

  • Road Frontage Type: Private Road

Measurements

  • Building Area Units: Square Feet
  • Frontage Type: Private Road
  • Lot Size Acres: 0.06
  • Lot Size Square Feet: 2,812

Financial

Taxes

  • Parcel Number: 1200-023-018-00001-000-0008
  • Tax Annual Amount: $6,724.00
  • Tax Assessed Value: $5,385.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Dishwasher, Dryer, Electric Oven, Electric Range, Refrigerator, Washer
  • Interior Features: First Floor Bedroom, First Floor Full Bath

Measurements

  • Living Area: 1,300
  • Living Area Source: Other

Rooms

  • Basement: Full, Storage Space
  • Has Basement: Yes
  • Bathrooms Full: 1
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 3
  • Rooms Total: 5

Other

Features

  • Accessibility Features: Accessible Hallway(s), Accessible Stairway, Stair Lift

Location

  • Subdivision Name: Hillcrest Park

Parking

Parking

  • Parking Features: Assigned
  • Parking Total: 2

Schools

Elementary School

  • Elementary School: Hillcrest
  • Elementary School District: Peekskill

High School

  • High School: Peekskill High School
  • High School District: Peekskill

Middle or Junior School

  • Middle Or Junior School: Peekskill Middle School
  • Middle Or Junior School District: Peekskill

Utilities

Equipment

  • Cooling: Wall/Window Unit(s)
  • Heating: Baseboard, Electric
  • Laundry Features: In Basement
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Sewer Connected
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this condo have?

There are 3 bedrooms and 2 bathrooms in this condo at 158 Rolling Way.

What schools are nearby to 158 Rolling Way?

Nearby schools include the Hillcrest Elementary School, Peekskill Middle School, and Peekskill High School.

Does this condo have parking?

Yes, there are 2 parking spaces available for 158 Rolling Way.

Are pets allowed at 158 Rolling Way?

Yes, 158 Rolling Way allows pets.

What are the annual taxes for 158 Rolling Way?

Annual taxes for this condo are estimated at $6,724.

How does 158 Rolling Way compare to other condos in Peekskill?

This condo is listed 3% above the average price for condos in Peekskill and has been on the market for 73 more days than the typical home in this area.

What building or home owners association is the condo part of?

This condo is part of the Self Managed home owners association.

What is the square footage on this condo?

According to the MLS, this listing is 1,300 sqft.

158 Rolling Way is a 3-bedroom, 2-bath condo for sale in Peekskill NY 10566. On Prevu for 130 days at $329,000. This includes a recent price decrease of $20,000. This home features 1,300 square feet of living space, located in Peekskill. The median listing price for condos in this area is $485,000. Nearby schools include Hillcrest Elementary School, Peekskill Middle School, and Peekskill High School. Additional amenities include dishwasher, pets allowed, parking, and washer/dryer. Browse more condo listings in New York.

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.