Orange County  »  10918  »  Winding Trl  »  38 Winding Trl

38 Winding Trl, Chester, NY 10918 - Property report

Also known as: 38 Winding Trl

Property image for 38 Winding Trl, Chester, NY 10918
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Property type

One Family Year-Round Residence (210)

Year built

1995

Acreage

6.1

Sale price

$649,000

General information

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Address
Primary address
38 Winding Trl
ZIP code
10918
County
Orange
Neighborhood
Chester
Parcel ID
5-1-81

Owner

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Sales
Sale date
03/21/2023
Sale price
$649,000
Arm's length
Tax
Tax year
2025-2026
Current property tax
$14,122
Zoning & Use
Zoning
AR-3
Building
Property type
One Family Year-Round Residence (210)
Building sq. ft.
2678
Buildings on lot
1
Stories
2
Year built
1995
AC
Yes
Rooms
8
Bedrooms
4
Bathrooms
2
Half bathrooms
1
Condition
Good
Exterior wall
Alum/vinyl
Building style
Colonial
Kitchen
1
Basement
Full
Fireplaces
1
Heating
Hot water/steam
Fuel
Oil
First story sq. ft.
Second story sq. ft.
Lot
Acreage
6.1
Water
Private
Sewer
Private

Area overview

Walk score
3 /100.  Car-Dependent
Transit score
0 /100.  Minimal Transit
Bike score
18 /100.  Somewhat Bikeable
School district
334001

View more such as transportation, nearby schools and risk designations.

Ownership

Ownership information for 38 Winding Trl, Chester, NY

Property owner name
Registered owner
Source
Deed
Owner contact information
Phone number
Owner address
Documents

Sales history for 38 Winding Trl, Chester, NY 10918

Sale date Sale price Buyer name Seller name
03/21/2023 $649,000 XXXXXXXXX XXXXXX XXXXXXXXX XXXXXX XXXXXXX XXXX X; XXXXXXX XXXXXXXX X
12/28/1995 $218,000 XXXXXXX XXXX X/XXXXXXXX XXXX XXX XXXXXXXXXXX
06/27/1995 $37,500 XXXX-XXXX XXXXXXXXXXX XXX XXXXXXXXXXXX XXXXXXX

*Most recent sales on record for this property.

More about Orange County property records.

Title documents

Date Type Amount Party 1 Party 2
04/10/2023 - R
03/21/2023 - D		 Mortgage
(RP / MTG)		 XXXXXXXXX XXXXXX XXXXXXXXX XXXXXX XXXXXX XXXX & XXXXX XX XXX XXXXXXXX XXXXXXXXXX XXXXXXXXXXXX XXXXXXX XXX XXX
04/10/2023 - R
03/21/2023 - D		 Deed XXXXXXX XXXX X XXXXXXXXX XXXXXX XXXXXXXXX XXXXXX
12/29/1995 - R
12/28/1995 - D		 Deed XXXX XXX XXXXXXXXXXX XXXXXXX XXXX X/XXXXXXXX
07/03/1995 - R
06/27/1995 - D		 Deed XXXXXXXXXXXX XXXXXXX XXXX-XXXX XXXXXXXXXXX XXX

*Most recent recorded documents on file for this property.

R: Recorded date
D: Document date

Tax

Property taxes for 38 Winding Trl, Chester, NY

Property tax data includes tax amount, market value and assessed value, exemptions, abatements and assessment history.

Current property tax
Tax year
2025-2026
Property tax
$14,122
Recent tax assessments
Market value
$708,200
Land value
$95,500
Building value
$612,700
Assessed value
$258,710

More about Orange County property taxes

Assessment history

See the assessment and property tax history, including the evolution of the total tax rate and corresponding property tax amount.

Tax year Market value Assessed value Tax rate Property tax Y-o-Y change
2025 $654,600 $258,710 54.5845 $14,122 +115.92%
2024 $631,000 $258,710 25.28 $6,540 -12.34%
2023 $528,900 $254,900 29.27 $7,461 -13.63%
2022 $460,100 $254,900 33.89 $8,639 +0.39%
2021 $465,700 $254,900 33.76 $8,605 -4.25%
2020 $438,000 $254,900 35.26 $8,988 +2.03%
2019 $432,000 $254,900 34.56 $8,809 n/a
Permits

Permit information for 38 Winding Trl, Chester, NY

No recently recorded permits for this property.

Neighborhood

Risk

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FEMA flood zones

FEMA flood zones
A, X

Transportation

Daily traffic map
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Schools

Nearest elementary schools

Name Rating Type Grade range No of students Distance (miles)
Monroe Day School NR Private PK, K-2 0 1.74
Monroe Day School NR Private PK, K-2 0 1.74
Sheri Torah V'yoel Moshe NR Private PK-12 3,663 2.25
Sheri Torah V'yoel Moshe NR Private PK-12 3,663 2.25
Cong Bnai Yoel NR Private K-12 1,800 2.25
North Main Street School 6 Public 2-5 532 2.49
Nearest middle schools

Name Rating Type Grade range No of students Distance (miles)
Sheri Torah V'yoel Moshe NR Private PK-12 3,663 2.25
Cong Bnai Yoel NR Private K-12 1,800 2.25
United Talmudical Academy Of Kiryas Joel NR Private PK, K-12 6,472 2.25
Bais Rochel School NR Private PK-12 4,845 2.25
Uta of Kiryas Joel-Girls NR Private PK-11 9,640 2.25
Chester Academy Middle High School 5 Public 6-12 570 3.83
Kiryas Joel Village School NR Public K-3, 7 150 3.89
Greenwood Lake Middle School 7 Public 4-8 258 4.16
Monroe Woodbury Middle School 6 Public 6-8 1,584 4.99
Nearest high schools

Name Rating Type Grade range No of students Distance (miles)
Sheri Torah V'yoel Moshe NR Private PK-12 3,663 2.25
Cong Bnai Yoel NR Private K-12 1,800 2.25
United Talmudical Academy Of Kiryas Joel NR Private PK, K-12 6,472 2.25
Bais Rochel School NR Private PK-12 4,845 2.25
Uta of Kiryas Joel-Girls NR Private PK-11 9,640 2.25
Chester Academy Middle High School 5 Public 6-12 570 3.83
Monroe Woodbury High School 7 Public 9-12 2,353 5.11
S S Seward Institute 5 Public 6-12 390 6.48
Washingtonville Senior High School 7 Public 9-12 1,318 7.58
Orange Ulster Boces NR Public K-12 994 7.59

Data provided by GreatSchools.org © 2026. All rights reserved.

Neighbors for 38 Winding Trl, Chester, NY

5 Park Pl, Chester 72 West Ave, Chester 5 Red Fox Run, Chester 1 Park Pl, Chester 3914 Summerville Way, Chester 61 Winding Trl, Chester 68 Winding Trl, Chester 132 Dug Rd, Monroe 3 Park Pl, Chester 9 Lori Ln, Chester 21 Red Fox Run, Chester 138 Dug Rd, Chester 643 Lakes Rd, Monroe 62 West Ave, Chester 391 Bull Mill Rd, Chester 71 Winding Trl, Chester 2 Red Fox Run, Chester 651 Lakes Rd, Monroe 399 Bull Mill Rd, Chester 60 West Ave, Chester

Nearby ZIP codes for 38 Winding Trl, Chester, NY

10910, Orange County, NY 10914, Orange County, NY 10916, Orange County, NY 10917, Orange County, NY 10921, Orange County, NY 10924, Orange County, NY 10925, Orange County, NY 10926, Orange County, NY 10930, Orange County, NY 10941, Orange County, NY 10958, Orange County, NY 10975, Orange County, NY 10979, Orange County, NY 10987, Orange County, NY 10990, Orange County, NY 10992, Orange County, NY 12543, Orange County, NY 12549, Orange County, NY 12577, Orange County, NY

Frequently asked questions

What is the year built for 38 Winding Trl, Chester, NY 10918?

The development at 38 Winding Trl, Chester, NY 10918 was built in 1995.

What is the total square footage of 38 Winding Trl, Chester, NY 10918?

38 Winding Trl, Chester, NY 10918 has a total of 2,678 square feet.

When was 38 Winding Trl, Chester, NY 10918 last sold and what was the sale price?

38 Winding Trl, Chester, NY 10918 was last sold on 03/21/2023 for $649,000.

What is the assessed value of 38 Winding Trl, Chester, NY 10918?

38 Winding Trl, Chester, NY 10918 is currently assessed at $258,710.

What are the property taxes for 38 Winding Trl, Chester, NY 10918?

The property taxes for 38 Winding Trl, Chester, NY 10918 total $14,121.

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