Welcome to 14 Windsor Drive, a beautifully renovated home in New Windsor offering a blend of classic charm and modern convenience. This 3-bedroom, 2-bath residence features a large living layout, hardwood floors, and abundant natural light. The kitchen is newly renovated with stainless steel appliances, ample cabinetry, and sleek countertops. The primary suite includes a private bath, and both full bathrooms have been tastefully updated with attractive tile and fixtures. Outside, a fully fenced yard boasts a large in-ground pool, a gazebo for outdoor dining or relaxation, and mature landscaping that ensures privacy. Located minutes from local shopping, schools, parks, and commuter routes, this property delivers both convenience and a serene setting.
Sold for $487,500
$487,500
14 Windsor Drive, New Windsor, NY 12553
3beds
1,864sqft
Single Family Residence, Residential
Built in 1952
0.43 Acres Lot
$486,900 Zestimate®
$262/sqft
$3,086 Estimated rent
Home value
$486,900
$428,000 - $555,000
$3,086/mo
Zestimate® history
Owner options
List your home for rent
$3,086/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,086/mo
Rent Zestimate®
Refinance and save
$3,418/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$3,418/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Abundant natural lightFully fenced yardLarge in-ground poolStainless steel appliancesSleek countertopsHardwood floorsAmple cabinetry
Zillow last checked:
Listing updated:
Listed by:
Michael Cahill 845-674-7386,
HomeSmart Homes & Estates 845-547-0005
Bought with:
Alicia S. Goldman, 10301220010
Christie's Int. Real Estate
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 921102
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Baseboard
Cooling
- Ductless
Appliances
- Included: Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s)
Features
- First Floor Bedroom
- Basement: Full
- Attic: Pull Stairs
Interior area
- Total structure area: 1,864
- Total interior livable area: 1,864 sqft
Property
Parking
- Parking features: Driveway
- Has uncovered spaces: Yes
Features
- Has private pool: Yes
- Pool features: In Ground
Lot
- Size: 0.43 Acres
Details
- Parcel number: 3348000190000001013.0000000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence, Residential
Materials
- Stucco
Condition
- Year built: 1952
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Water Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: New Windsor
Financial & listing details
- Price per square foot: $262/sqft
- Tax assessed value: $367,100
- Annual tax amount: $8,490
- Date on market: 10/6/2025
- Cumulative days on market: 18 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Price history
| Date | Event | Price |
|---|---|---|
| 2/6/2026 | Sold | $487,500+2.6%$262/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #921102 Report a problem | ||
| 12/2/2025 | Pending sale | $475,000$255/sqft |
Source: OneKey® MLS as distributed by MLS GRID #921102 Report a problem | ||
| 10/24/2025 | Listing removed | $475,000$255/sqft |
Source: OneKey® MLS as distributed by MLS GRID #921102 Report a problem | ||
| 10/6/2025 | Listed for sale | $475,000-6.9%$255/sqft |
Source: OneKey® MLS as distributed by MLS GRID #921102 Report a problem | ||
| 10/5/2025 | Listing removed | $510,000$274/sqft |
Source: NY State MLS #11565373 Report a problem | ||
| 8/29/2025 | Listed for sale | $510,000-7.3%$274/sqft |
Source: NY State MLS #11565373 Report a problem | ||
| 8/27/2025 | Listing removed | $550,000$295/sqft |
Source: NY State MLS #11544648 Report a problem | ||
| 7/29/2025 | Listed for sale | $550,000+205.6%$295/sqft |
Source: NY State MLS #11544648 Report a problem | ||
| 4/23/2025 | Sold | $180,000-10%$97/sqft |
Source: Public Record Report a problem | ||
| 12/9/2024 | Contingent | $200,000$107/sqft |
Source: NY State MLS #11352028 Report a problem | ||
| 11/13/2024 | Price change | $200,000-33.3%$107/sqft |
Source: NY State MLS #11352028 Report a problem | ||
| 10/10/2024 | Listed for sale | $300,000$161/sqft |
Source: NY State MLS #11352028 Report a problem | ||
| 8/1/2022 | Listing removed | -- |
Source:  RE/MAX International Report a problem | ||
| 3/2/2022 | Pending sale | $300,000$161/sqft |
Source: OneKey® MLS as distributed by MLS GRID #H6158990 Report a problem | ||
| 2/7/2022 | Listed for sale | $300,000$161/sqft |
Source: OneKey® MLS as distributed by MLS GRID #H6158990 Report a problem | ||
| 2/2/2022 | Pending sale | $300,000$161/sqft |
Source: RE/MAX International #405851 Report a problem | ||
| 1/27/2022 | Listed for sale | $300,000+20%$161/sqft |
Source: OneKey® MLS as distributed by MLS GRID #H6158990 Report a problem | ||
| 1/14/2016 | Listing removed | $250,000$134/sqft |
Source: ERA 1st Independent Realty Grp #556143 Report a problem | ||
| 2/14/2015 | Listed for sale | $250,000-28.6%$134/sqft |
Source: ERA 1st Independent Realty #556143 Report a problem | ||
| 1/14/2015 | Listing removed | $349,900$188/sqft |
Source: ERA 1st Independent Realty #556143 Report a problem | ||
| 1/14/2014 | Listed for sale | $349,900$188/sqft |
Source: ERA 1st Independent Realty #556143 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $35,900 |
| 2024 | -- | $35,900 |
| 2023 | -- | $35,900 |
| 2022 | -- | $35,900 |
| 2021 | -- | $35,900 |
| 2020 | -- | $35,900 |
| 2019 | -- | $35,900 |
| 2018 | -- | $35,900 |
| 2017 | $6,475 | $35,900 |
| 2016 | -- | $35,900 |
| 2015 | -- | $35,900 |
| 2014 | -- | $35,900 |
| 2013 | -- | $35,900 |
| 2012 | -- | $35,900 |
| 2011 | -- | $35,900 |
| 2010 | -- | $35,900 |
| 2009 | -- | $35,900 |
| 2007 | -- | $35,900 |
| 2006 | -- | $35,900 |
| 2005 | -- | $35,900 |
| 2004 | -- | $35,900 |
| 2002 | -- | $35,900 |
| 2001 | -- | $35,900 |
| 2000 | -- | $35,900 |
Find assessor info on the county website
Neighborhood: 12553
Nearby homes
- $379,3003 bd1 ba1k sqft12 Windsor Dr, New Windsor, NY 12553Off Market
- $336,0002 bd1 ba900 sqft5 Sunset Dr, New Windsor, NY 12553Sold
- $573,2004 bd3 ba1.9k sqft7 Windsor Dr, New Windsor, NY 12553Off Market
- $394,3003 bd1 ba1.3k sqft10 Windsor Dr, New Windsor, NY 12553Off Market
- $320,9002 bd1 ba1.1k sqft5 Windsor Dr, New Windsor, NY 12553Off Market
- $304,2003 bd1 ba864 sqft7 Sunset Dr, New Windsor, NY 12553Off Market
- $354,4004 bd2 ba1.2k sqft8 Windsor Dr, New Windsor, NY 12553Off Market
- $451,8003 bd2 ba1.4k sqft96 Cedar Ave, New Windsor, NY 12553Off Market
Nearby schools
GreatSchools rating
- 8/10New Windsor SchoolGrades: K-5Distance: 0.5 mi
- 2/10South Middle SchoolGrades: 6-8Distance: 0.9 mi
- 3/10Newburgh Free Academy Main CampusGrades: 9-12Distance: 1.8 mi
Schools provided by the listing agent
- Elementary: Newburgh
- Middle: Newburgh
- High: Newburgh Free Academy
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.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$486,900
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$486,900
- New York
- Orange County
- New Windsor
- 12553
- 14 Windsor Drive
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other New Windsor Topics
