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20 Hilltop Drive, New Windsor, NY, 12553

2beds
2baths
1,152sqft
$389,900
$338price/sqft
$2,992/moest. monthly cost
$119,680/yrincome needed

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

32
WalkingCar-Dependent
0
TransitVery Limited Transit
25
BikeSomewhat Bikeable

Schools

8/10
New Windsor SchoolGrades K-50.4 mi
2/10
South Middle SchoolGrades 6-80.8 mi

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
    Cold WaveModerate
  • Strong Wind
    Strong WindModerate
  • Winter Weather
    Winter WeatherModerate

How This Home’s Risks Compare

Cold Wave
Strong Wind
Winter Weather

FEMA Declared Disasters in Orange County and New York

Fire
Flood
Severe Storm

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

MonthlyAnnual
Mortgage $1,971$23,652
Home Insurance *$119$1,428
Property Taxes $656$7,872
Electricity $246$2,954
Total$2,992$35,904
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$102,582/yr
40% on housing$89,760/yr
45% on housing$79,786/yr

New York FAIR Plan Programs

New York Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 20,669Commercial: 1,556
Total Premiums$32.27M
Total Exposure$7.63B

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.

Insurance Growth Rate5-year average: -1.9%
-1.9%
0%30.0%
Electricity Growth Rate10-year average: 7.1%
7.1%
0%15.0%
Property Taxes Growth Rate2-year average: -2.6%
-2.6%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$338This listing

vs Other Active Listings

Avg $/sqft

ZIP 12553$214
Orange County$275

vs Homes Sold Last Month

Median $/sqft

ZIP 12553$258
Orange County$263

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

DateEventPrice
2026-06-12Listed for sale$389,900
2025-02-13Listing removed$2,250
2025-02-04Listed for rent$2,250
2021-11-15Sold$250,000
2021-08-19Pending sale$250,000
2021-07-27Price change$250,000
2021-06-22Price change$265,000
2021-06-13Listed for sale$279,999
2013-01-17Sold$123,000
2012-09-20Price change$134,431
2012-09-05Price change$138,831
2012-08-12Price change$139,931
2012-08-07Price change$147,741
2012-07-07Price change$149,941
2012-06-27Price change$153,351
2012-06-22Price change$149,941
2012-04-01Price change$154,451
2012-03-09Price change$157,751
2012-02-14Price change$159,951
2012-01-15Price change$163,361
2011-11-10Listed for sale$169,961

For Sale by Agent

AgentMartin Krakower
BrokerageeXp Realty

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