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!.
Pending
$349,000
158 Rolling Way, Peekskill, NY 10566
3beds
1,300sqft
Condominium, Residential
Built in 1968
-- sqft lot
$-- Zestimate®
$268/sqft
$133/mo HOA
What's special
Two additional bedroomsSpacious and inviting condoPrivate deckAbundant closet space throughoutGenerously sized primary bedroomConvenient powder roomBright eat-in kitchen
- 48 days |
- 1,454 |
- 89 |
Zillow last checked:
Listing updated:
Listed by:
RE/MAX Prestige Properties 914-831-3090,
Maria O'Connor 914-980-4274,
Rachel F. Chason 914-260-9896,
RE/MAX Prestige Properties
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 996096
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Other
- Description: Entry, Kitchen, Dining Room, Living Room, Half Bathroom
- Level: First
Other
- Description: Recreation, Storage, Laundry
- Level: Basement
Other
- Description: Bedroom, Bedroom, Bedroom, Full Bathroom
- Level: Second
Heating
- Baseboard, Electric
Cooling
- Wall/Window Unit(s)
Appliances
- Included: Dishwasher, Dryer, Electric Oven, Electric Range, Refrigerator, Washer
- Laundry: In Basement
Features
- First Floor Bedroom, First Floor Full Bath
- Basement: Full,Storage Space
- Attic: None
- Has fireplace: No
- Common walls with other units/homes: 2+ Common Walls
Interior area
- Total structure area: 1,300
- Total interior livable area: 1,300 sqft
Property
Parking
- Total spaces: 2
- Parking features: Assigned
Accessibility
- Accessibility features: Accessible Hallway(s), Accessible Stairway, Stair Lift
Features
- Levels: Three Or More
Lot
- Size: 2,812 Square Feet
Details
- Parcel number: 1200023018000010000008
- Special conditions: None
Construction
Type & style
- Home type: Condo
- Architectural style: Garden
- Property subtype: Condominium, Residential
- Attached to another structure: Yes
Materials
- Brick, Wood Siding
Condition
- Year built: 1968
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Sewer Connected
Community & HOA
Community
- Subdivision: Hillcrest Park
HOA
- Has HOA: Yes
- Amenities included: Maintenance Grounds, Snow Removal, Trash
- Services included: Common Area Maintenance, Snow Removal, Trash
- HOA fee: $400 quarterly
- HOA name: Self Managed
Location
- Region: Peekskill
Financial & listing details
- Price per square foot: $268/sqft
- Tax assessed value: $5,385
- Annual tax amount: $6,724
- Date on market: 5/8/2026
- Cumulative days on market: 47 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/19/2026 | Pending sale | $349,000$268/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #996096 Report a problem | ||
| 5/8/2026 | Listed for sale | $349,000+29.3%$268/sqft |
Source: OneKey® MLS as distributed by MLS GRID #996096 Report a problem | ||
| 4/14/2005 | Sold | $270,000$208/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $5,385 |
| 2024 | -- | $5,385 |
| 2023 | -- | $5,385 |
| 2022 | -- | $5,385 |
| 2021 | -- | $5,385 |
| 2020 | -- | $5,385 |
| 2019 | -- | $5,385 |
| 2018 | -- | $5,385 |
| 2017 | -- | $5,385 |
| 2016 | -- | $5,385 |
| 2015 | $2,116 | $5,385 |
| 2014 | $2,116 | $5,385 |
| 2013 | $2,116 | $5,385 -21% |
| 2012 | -- | $6,817 |
| 2011 | -- | $6,817 |
| 2010 | -- | $6,817 |
| 2009 | -- | $6,817 |
| 2008 | -- | $6,817 |
| 2007 | -- | $6,817 |
| 2006 | -- | $6,817 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 10566
Nearby schools
GreatSchools rating
- 4/10Hillcrest SchoolGrades: 3-5Distance: 0.3 mi
- 4/10Peekskill Middle SchoolGrades: 6-8Distance: 1.1 mi
- 3/10Peekskill High SchoolGrades: 9-12Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Hillcrest
- Middle: Peekskill Middle School
- High: Peekskill High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Westchester County
- Peekskill
- 10566
- 158 Rolling Way
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