Google street view image for 149 Trailside Rd, Windham, NY 12496

Off market mar 1993 for $750K

$2,529,898

Est. refi paymentEst. refi $4,944/mo

•

5.5 ba

•

4,998

sq ft

149 Trailside Rd, Windham, NY 12496

About this home

149 Trailside Rd is a 4,998 square foot house on a 0.41 acre lot with 5 bedrooms and 5.5 bathrooms. - it last sold on March 09, 1993 for $750,000. Based on Redfin's Windham data, we estimate the home's value is $2,529,898.

Single-familyProperty Type

1989Year Built

0.41 acresLot Size

$506Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,529,898

$1.8M since sold in March 1993$136K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 35.5% higher than the average sale price ($1.87M) of 6 comparable homes.

SOLD JUN 8, 2026
$1,200,000
A
5 beds5.5 baths3,752 sq ft
7 Meadow Ln, Windham, NY 12496
Listing by Compass Greater NY, LLC
SOLD AUG 7, 2026
$3,000,000
B
6 beds5 baths5,000 sq ft
209 Club Rd, Windham, NY 12496
Listing by Brainard Ridge Management
SOLD MAY 5, 2026
$3,100,000
C
6 beds5 baths5,021 sq ft
219 Club Road Rd, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD MAY 22, 2026
$600,000
D
4 beds3.5 baths2,100 sq ft
57 Brainard Ridge Rd Unit 3-E, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD JUL 10, 2026
$1,900,000
E
5 beds4.5 baths3,150 sq ft
8 Stonewall Ln, Windham, NY 12496
Listing by Douglas Elliman Real Estate
SOLD FEB 6, 2026
$1,400,000
F
4 beds4.5 baths2,874 sq ft
2 Enclave West Dr Unit W-10, Windham, NY 12496
Listing by Brainard Ridge Management

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Earn from this home

Sell

$2,382,597

Est. take-home

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Est. cash available

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Rent

$4,285/mo

Redfin rental estimate

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Market trends in 12496, NY

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

97.1%

+1.9% MoM

Median sale price

$730K

$73K MoM

Avg. days on market

159d

2 days MoM

Recently sold homes

5 MoM

New listings for sale

NEW 6 HRS AGO
$2,200,000
4 beds2.5 baths3,615 sq ft
618 W Settlement Rd, Ashland, NY 12407
$525,000
4 beds2 baths1,872 sq ft
543 Mill St, Windham, NY 12496
See all

Provided by Redfin

Sale history for 149 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2026

$22,471

$225,700 + $1,065,100

$1,290,800

2025

$22,471 (+4.6%)

$225,700 + $1,065,100

$1,290,800

2024

$21,491 (+2.3%)

$225,700 + $1,065,100

$1,290,800

2023

$21,005 (+0.6%)

$225,700 + $1,065,100

$1,290,800

2022

$20,871 (+0.6%)

$225,700 + $1,065,100

$1,290,800

2021

$20,755

$225,700 + $1,065,100

$1,290,800

2020

$20,759 (+0.1%)

$225,700 + $1,065,100

$1,290,800

2019

$20,730 (−0.5%)

$225,700 + $1,065,100

$1,290,800

2018

$20,833 (−1.3%)

$225,700 + $1,065,100

$1,290,800

2017

$21,100 (+3.0%)

$225,700 + $1,065,100

$1,290,800

2016

$20,493 (+1.1%)

$182,400 + $1,088,400

$1,270,800

2015

$20,262 (+0.9%)

$182,400 + $1,088,400

$1,270,800

2014

$20,078

$182,400 + $1,088,400

$1,270,800

Tax history for 149 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2026

$22,471

$225,700 + $1,065,100

$1,290,800

2025

$22,471 (+4.6%)

$225,700 + $1,065,100

$1,290,800

2024

$21,491 (+2.3%)

$225,700 + $1,065,100

$1,290,800

2023

$21,005 (+0.6%)

$225,700 + $1,065,100

$1,290,800

2022

$20,871 (+0.6%)

$225,700 + $1,065,100

$1,290,800

2021

$20,755

$225,700 + $1,065,100

$1,290,800

2020

$20,759 (+0.1%)

$225,700 + $1,065,100

$1,290,800

2019

$20,730 (−0.5%)

$225,700 + $1,065,100

$1,290,800

2018

$20,833 (−1.3%)

$225,700 + $1,065,100

$1,290,800

2017

$21,100 (+3.0%)

$225,700 + $1,065,100

$1,290,800

2016

$20,493 (+1.1%)

$182,400 + $1,088,400

$1,270,800

2015

$20,262 (+0.9%)

$182,400 + $1,088,400

$1,270,800

2014

$20,078

$182,400 + $1,088,400

$1,270,800

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Type: Full

Bathroom Information
# of Full Baths: 5
# of 1/2 Baths: 1

Heating & Cooling
Heating Fuel Type: Electric
Heating Type: Electric

Fireplace Information
# of Fireplaces: 4
Has Fireplace

Room Information
# of Rooms: 10

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Contemporary
Exterior Wall: Wood

Property Information
Living Sq. Ft: 4,998
Ground Floor Sq. Ft: 3,846
# of Stories: 2
Legal Description: VILLAGE EAST LOT 43

Lot Information
# of Buildings: 1
Land Sq. Ft: 17,860
Legal Lot Number: 16
Legal Block Number: 3
Municipality Name: WINDHAM
Acres: 0.41
Zoning Code: 01
State Use Description: SINGLE FAMILY RESID

Utility Information
Sewer Type: Commercial
Water Service Type: Commercial

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 5
Baths: 5.5
Sq. Ft.: 4,998
Stories: 2.0
Lot Size: 0.41 acres
Style: Single Family Residential
Year Built: 1989
Year Renovated: —
County: Greene County
APN: 194600A09501000030160000000

Home facts updated by county records on Sep 25, 2026

Around this home

Schools

Windham Ashland Central School

Public PreK-12 • Assigned • 0.6mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

7 days above 86° expected this year, 17 days in 30 years

2/10 Wind Factor

4% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Windham, NY • 12496

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.3 hours in June and 3.3 hours in December, placing it below the U.S. average for solar exposure.

8.3 hrs

3.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.40M – $2.91M

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NEW CONSTRUCTION

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New listings for sale in 12407

NEW 6 HRS AGO3D WALKTHROUGH

$2,200,000

4 beds2.5 baths3,615 sq ft

618 W Settlement Rd, Ashland, NY 12407

$525,000

4 beds2 baths1,872 sq ft

543 Mill St, Windham, NY 12496

Home values near 149 Trailside Rd

Data from public records.

Address	Redfin Estimate
142 Trailside Rd, Windham, NY 6 Beds \| 5.5 Baths \| 5150 Sq. Ft.	$3,445,166
153 Trailside Rd, Windham, NY 4 Beds \| 4.5 Baths \| 4616 Sq. Ft.	$1,653,634

Address	Redfin Estimate
115 Trailside Rd, Windham, NY 4 Beds \| 3.5 Baths \| 2534 Sq. Ft.	$1,217,949
148 Trailside Rd, Windham, NY 5 Beds \| 3.5 Baths \| 4364 Sq. Ft.	$2,093,421

Address	Redfin Estimate
133 Trailside Rd, Windham, NY 5 Beds \| 3.5 Baths \| 4536 Sq. Ft.	$1,972,858
150 Trailside Rd, Windham, NY 9 Beds \| 7 Baths \| 6858 Sq. Ft.	$2,332,936

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12496, NY

Sale history for 149 Trailside Rd

Tax history for 149 Trailside Rd

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12407

Home values near 149 Trailside Rd

More real estate resources