# 104 Rolling Way, Peekskill, NY 10566 > **TL;DR:** 3bd/2ba condo, $349,999 ($236/sqft), built 1965, 1,480 sqft. > A/C. Est. $2,241/mo. Listed 7 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $349,999 | | Price/sqft | $236 | | Bedrooms | 3 | | Bathrooms | 1 full, 1 half | | Square Feet | 1,480 | | Year Built | 1965 | | Lot Size | 2,487 sqft (0.06 acres) | | Stories | 2 | | Property Type | Condo (Condominium) | | Status | Active | | Days on Market | 7 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,770 | | Estimated Insurance | $102 | | HOA | $369 | | **Total** | **$2,241** | ## Nearby Schools - **Elementary:** Hillcrest - **Middle:** Peekskill Middle School - **High:** Peekskill High School ## Key Amenities - A/C ## Property Highlights - Built in 1965 - 0.06 acre lot - 2 stories - 2 parking spaces ## Description ### Agent Description Enjoy a little more of what makes Hudson Valley living special at 104 Rolling Way. From an afternoon exploring downtown Peekskill's shops and arts scene to dinner at a local restaurant or time along the Hudson River waterfront, this location puts a variety of experiences within reach. Nearby parks offer opportunities to spend time outdoors, and the Peekskill Metro-North station provides a connection to destinations along the Hudson Line and Grand Central. At home, settle into the comfort of this townhouse-style condominium in Hillcrest Park. Start the day with coffee on the rear deck, make time for a leisurely meal, or unwind indoors after exploring the area. The two-level layout separates the main living spaces from the upstairs bedrooms, creating space for both gathering and quieter moments. Offering approximately 1,480 square feet, the home includes three bedrooms and one-and-a-half baths. The main level features a kitchen, living and dining areas, and a convenient half bath, with three bedrooms and a full bath upstairs. Bring your own style and everyday routines to a home with access to Peekskill's dining, shopping, recreation, and riverfront surroundings. ## Location - **Address:** 104 Rolling Way, Peekskill, NY 10566 - **County:** Westchester County - **Neighborhood:** Hillcrest Park - **Coordinates:** 41.29944, -73.914945 - **Google Maps:** https://www.google.com/maps?q=41.29944,-73.914945 ## Listing Agent - **Name:** Twudian Wallace - **Brokerage:** Keller Williams Realty - **Broker Phone:** (845) 928-8000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/104-Rolling-Way_Peekskill_NY_10566_M30224-33094?f=listhub&s=MLSLINY&m=1066409&c=propsimple) ## Photos ![104 Rolling Way - Photo 1](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1929526716r.jpg) ![104 Rolling Way - Photo 2](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f2807277628r.jpg) ![104 Rolling Way - Photo 3](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1220148172r.jpg) ![104 Rolling Way - Photo 4](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3979408637r.jpg) ![104 Rolling Way - Photo 5](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f570528225r.jpg) ![104 Rolling Way - Photo 6](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3997468388r.jpg) ![104 Rolling Way - Photo 7](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3979408637r.jpg) ![104 Rolling Way - Photo 8](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3492206062r.jpg) ![104 Rolling Way - Photo 9](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f372478561r.jpg) ![104 Rolling Way - Photo 10](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3325999009r.jpg) ![104 Rolling Way - Photo 11](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1515461302r.jpg) ![104 Rolling Way - Photo 12](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f65084165r.jpg) ![104 Rolling Way - Photo 13](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f2039461879r.jpg) ![104 Rolling Way - Photo 14](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1105830378r.jpg) ![104 Rolling Way - Photo 15](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1105830378r.jpg) ![104 Rolling Way - Photo 16](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1398072509r.jpg) ![104 Rolling Way - Photo 17](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3340234489r.jpg) ![104 Rolling Way - Photo 18](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1988461969r.jpg) ![104 Rolling Way - Photo 19](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3906132629r.jpg) ![104 Rolling Way - Photo 20](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f307980079r.jpg) ![104 Rolling Way - Photo 21](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3152428812r.jpg) ![104 Rolling Way - Photo 22](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1039823242r.jpg) ![104 Rolling Way - Photo 23](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3238653626r.jpg) ![104 Rolling Way - Photo 24](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3076111376r.jpg) ![104 Rolling Way - Photo 25](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f4170385874r.jpg) ![104 Rolling Way - Photo 26](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f1805798560r.jpg) ![104 Rolling Way - Photo 27](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3356555135r.jpg) ![104 Rolling Way - Photo 28](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f2739565914r.jpg) ![104 Rolling Way - Photo 29](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f3808445498r.jpg) ![104 Rolling Way - Photo 30](http://lh.rdcpix.com/100ba02eece2f0c15ffbbc23f60c475al-f2807032149r.jpg) --- **MLS#:** 1066409 | **Updated:** 2026-10-28 **Source:** listhub *Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/104-rolling-way-peekskill-ny-10566-9278183da35b49fbb23e6f49f87e4647) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/104-rolling-way-peekskill-ny-10566-9278183da35b49fbb23e6f49f87e4647#listing", "url": "https://www.propertysimple.ai/listing/104-rolling-way-peekskill-ny-10566-9278183da35b49fbb23e6f49f87e4647", "name": "104 Rolling Way, Peekskill, NY 10566", "description": "Enjoy a little more of what makes Hudson Valley living special at 104 Rolling Way. From an afternoon exploring downtown Peekskill's shops and arts scene to dinner at a local restaurant or time along the Hudson River waterfront, this location puts a variety of experiences within reach. 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