Jodi Gillespie
Gillespie Real Estate LLC
(845) 420-1782
43 Total Sales
8 in New Windsor
$165K - $545K Price Range
14 Windsor Dr New Windsor, NY 12553
New Windsor AreaEstimated Value: $469,000 - $490,000
3
Beds
2
Baths
1,864
Sq Ft
$259/Sq Ft
Est. Value
Highlights
- In Ground Pool
- Stainless Steel Appliances
- Baseboard Heating
- Ranch Style House
About This Home
As of February 2026Welcome 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.
Last Agent to Sell the Property
HomeSmart Homes & Estates Brokerage Phone: 845-547-0005 License #10401335508 Listed on: 10/06/2025
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Home Details
Home Type
- Single Family
Est. Annual Taxes
- $8,490
Year Built
- Built in 1952
Lot Details
- 0.43
Parking
- Driveway
Home Design
- Ranch Style House
- Stucco
Interior Spaces
- 1,864 Sq Ft Home
- Basement Fills Entire Space Under The House
Kitchen
- Oven
- Range
- Microwave
- Stainless Steel Appliances
Bedrooms and Bathrooms
- 3 Bedrooms
- 2 Full Bathrooms
Schools
- Newburgh Elementary And Middle School
- Newburgh Free Academy High School
Utilities
- Ductless Heating Or Cooling System
- Baseboard Heating
Additional Features
- In Ground Pool
- 18,720 Sq Ft Lot
Listing and Financial Details
- Assessor Parcel Number 334800-019-000-0001-013.000-0000
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Oct 6, 2025
Closed on
Feb 5, 2026
Sold by
Jmj Family Re Llc
Bought by
Seller's Agent
Michael Cahill
HomeSmart Homes & Estates
Buyer's Agent
Alicia Goldman
Christie's Int. Real Estate
List Price
$475,000
Sold Price
$487,500
Premium/Discount to List
$12,500
2.63%
Views
75
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$5,198
Avg. Annual Appreciation
-1.80%
Purchase Details
Closed on
Feb 5, 2025
Sold by
Santa A Quaglietta and Santa Quaglietta
Bought by
Jmj Family Re Llc
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$266,875
Interest Rate
6.65%
Mortgage Type
Purchase Money Mortgage
Purchase Details
Closed on
Jun 26, 2006
Sold by
Quaglietta Santa
Bought by
Quaglietta Trustee Santa A
Home Values in the Area
Average Home Value in this Area
Agents Specializing in New Windsor, NY
-
Jodi Gillespie
-
Nazma Sooknanan
Nazma Sooknanan
Nazma Real Estate LLC
(845) 999-0913
24 Total Sales
1 in New Windsor
$500,000 Price
-
Karen Briscoe-Reed
Karen Briscoe-Reed
KW MidHudson
(845) 420-1916
63 Total Sales
1 in New Windsor
$230,000 Price
-
Jennifer DiCostanzo
Jennifer DiCostanzo
(917) 540-4360
157 Total Sales
3 in New Windsor
$417K - $658K Price Range
-
Maria Campanelli
Maria Campanelli
BHHS River Towns Real Estate
(914) 529-6616
211 Total Sales
1 in New Windsor
$318,000 Price
-
Luanne McGann
Luanne McGann
Century 21 Full Service Realty
(845) 479-6100
79 Total Sales
5 in New Windsor
$353K - $535K Price Range
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $480,000 | Stewart Title | ||
| Jmj Family Re Llc | $180,000 | None Available | |
| Quaglietta Trustee Santa A | -- | Jeffrey Russell Werner |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $266,875 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 02/06/2026 02/06/26 | Sold | $487,500 | 0.0% | $262 / Sq Ft |
| 11/28/2025 11/28/25 | Pending | -- | -- | -- |
| 10/24/2025 10/24/25 | Off Market | $487,500 | -- | -- |
| 10/06/2025 10/06/25 | For Sale | $475,000 | -- | $255 / Sq Ft |
Source: OneKey® MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $8,423 | $35,900 | $8,500 | $27,400 |
| 2024 | $8,370 | $35,900 | $8,500 | $27,400 |
| 2023 | $8,370 | $35,900 | $8,500 | $27,400 |
| 2022 | $8,500 | $35,900 | $8,500 | $27,400 |
| 2021 | $8,491 | $35,900 | $8,500 | $27,400 |
| 2020 | $8,896 | $35,900 | $8,500 | $27,400 |
| 2019 | $3,246 | $35,900 | $8,500 | $27,400 |
| 2018 | $3,246 | $35,900 | $8,500 | $27,400 |
| 2017 | $8,324 | $35,900 | $8,500 | $27,400 |
| 2016 | $6,475 | $35,900 | $8,500 | $27,400 |
| 2015 | -- | $35,900 | $8,500 | $27,400 |
| 2014 | -- | $35,900 | $8,500 | $27,400 |
Source: Public Records
Agents Affiliated with this Home
-
Michael Cahill
Seller's Agent in 2026
Michael Cahill
HomeSmart Homes & Estates
(845) 674-7386
47 Total Sales
-
Alicia Goldman
Buyer's Agent in 2026
Alicia Goldman
Christie's Int. Real Estate
(914) 355-1137
85 Total Sales
Map
Source: OneKey® MLS
MLS Number: 921102
APN: 334800-019-000-0001-013.000-0000
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The data relating to real estate for sale or lease on this web site comes in part from OneKey® MLS. Real estate listings held by brokerage firms other than Ten-X are marked with the OneKey® MLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker.
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Copyright 2026 OneKey® MLS. All rights reserved.
Based on information submitted to the MLS GRID
Listings courtesy of OneKey® MLS as distributed by MLS GRID
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