




20 Hilltop Drive, New Windsor, NY, 12553
About This Home
Welcome to 20 Hilltop Dr in New Windsor—an excellent opportunity for both investors and owner-occupants alike. Conveniently located with easy access to Interstate 84, the New York State Thruway, and Route 9W, this property offers an ideal location for commuters traveling throughout the Hudson Valley and beyond. Inside, you’ll find hardwood floors throughout much of the home, along with two full bathrooms and a functional layout designed for comfortable living. The walkout basement provides direct access to a level backyard, offering additional potential and flexibility. Outside, enjoy a rear deck perfect for entertaining, a spacious yard, and a storage shed for extra storage. Currently occupied by a month-to-month tenant that can be vacated with 60 days notice, this property presents an attractive opportunity for investors seeking immediate rental income while also offering flexibility for future owner-occupancy. Buyers are encouraged to look beyond the current occupancy and focus on the home’s overall layout, features, and potential. The property is actively lived in by a family with young children, and while every effort is made to accommodate showings, the home may not always present as a staged or vacant property. This is a wonderful opportunity to envision the long-term value and possibilities this home has to offer. Whether you’re looking to expand your investment portfolio or purchase a home in a highly convenient location, 20 Hilltop Dr is a property you won’t want to miss.
Getting Around
Schools
Construction
Condition
- Year built: 1952
Materials
- Construction materials: Frame
Type & Style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subType: Single Family Residence,Residential
Interior
Appliances
- Appliances included: Other,Oven,Range,Refrigerator
- Laundry features: Washer/Dryer Hookup,In Basement
Basement
- Has basement: Yes
- Basement: Walk-Out Access
Bedrooms & Bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Features
- First Floor Bedroom,Eat-in Kitchen,Primary Bathroom,Master Downstairs,Quartz/Quartzite Counters
- Attic: Walkup
Heating & Cooling
- Heating features: Forced Air,Oil
- Cooling features: Wall/Window Unit(s)
Interior Area
- Total structure area: 1,152
- Total interior livable area: 1,152 sqft
Property
Details
- Parcel number: 3348000160000004019.0000000
- Special condition: None
Lot
- Lot size: 9,150 sqft
Parking
- Parking features: Driveway
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Cold Wave
- Strong Wind
- Winter Weather
How This Home’s Risks Compare
FEMA Declared Disasters in Orange County and New York
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $1,971 | $23,652 |
| Home Insurance * | $119 | $1,428 |
| Property Taxes | $656 | $7,872 |
| Electricity | $246 | $2,954 |
| Total | $2,992 | $35,904 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-06-12 | Listed for sale | $389,900 |
| 2025-02-13 | Listing removed | $2,250 |
| 2025-02-04 | Listed for rent | $2,250 |
| 2021-11-15 | Sold | $250,000 |
| 2021-08-19 | Pending sale | $250,000 |
| 2021-07-27 | Price change | $250,000 |
| 2021-06-22 | Price change | $265,000 |
| 2021-06-13 | Listed for sale | $279,999 |
| 2013-01-17 | Sold | $123,000 |
| 2012-09-20 | Price change | $134,431 |
| 2012-09-05 | Price change | $138,831 |
| 2012-08-12 | Price change | $139,931 |
| 2012-08-07 | Price change | $147,741 |
| 2012-07-07 | Price change | $149,941 |
| 2012-06-27 | Price change | $153,351 |
| 2012-06-22 | Price change | $149,941 |
| 2012-04-01 | Price change | $154,451 |
| 2012-03-09 | Price change | $157,751 |
| 2012-02-14 | Price change | $159,951 |
| 2012-01-15 | Price change | $163,361 |
| 2011-11-10 | Listed for sale | $169,961 |
