OFF MARKET

Off market jun 2022 for $1.7M

$2,093,421

Est. refi paymentEst. refi $677/mo

•

4,364

sq ft

148 Trailside Rd, Windham, NY 12496

About this home

Upon entering this lovingly renovated 5 bdrm, 3.5 bath home on Windham Mountain, you are greeted w/ polished limestone flooring & a wall of reclaimed lumber artfully balanced w/ sophisticated wall paper. You'll find this play of earth elements & refinement throughout the home. The 1st level is comprised of a well organized boot/ski rm, family rm w/ skillfully laid blue stone fireplace surround, 3 bdrms & 2 fully tiled baths. Upstairs you'll find a light flooded, designer kitchen w/ large butcher block island, Wolf range, custom cabinetry, high end appliances & adjoining dining area. The living room w/ massive bluestone fireplace, vaulted ceilings & reclaimed beams, is framed by a wall of windows w/ mountain views. There is an additional fireplace in master bdrm & a fabulous master bath with large soaking tub. Another bdrm, 1/2 bath & new ski room completes this floor. Large loft above LV is currently set up as an office. Super close ski trail access & selling turnkey!

Single-familyProperty Type

1999Year Built

0.89 acresLot Size

$480Est. Price/Sq.Ft.

1 car garageParking

Listing by Nina Porter • Past Member

Bought with Nina Porter • Keller Williams Realty HV Nort

Redfin checked: a few seconds ago

•Source:HVCRMLS #141031

Redfin Estimate

$2,093,421

$343K since sold in June 2022$3,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 52.3% higher than the average sale price ($1.37M) of 6 comparable homes.

SOLD MAY 12, 2026
$1,571,126
A
5 beds3.5 baths4,312 sq ft
102 Thunderbird Terrace Ter, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD APR 3, 2026
$340,000
B
5 beds3 baths4,944 sq ft
317 Mitchell Hollow Rd, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD AUG 7, 2026
$3,000,000
C
6 beds5 baths5,000 sq ft
209 Club Rd, Windham, NY 12496
Listing by Brainard Ridge Management
SOLD MAY 2, 2026
$1,350,000
D
4 beds4 baths3,712 sq ft
11 Whisper Creek Dr #504, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD DEC 22, 2025
$585,000
E
5 beds3 baths2,644 sq ft
183 County Road 65, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
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

$688,174

Est. take-home

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Refinance

Est. cash available

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Rent

$4,319/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

$525,000
4 beds2 baths1,872 sq ft
543 Mill St, Windham, NY 12496
See all

Provided by Redfin

Sale history for 148 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2026

$19,097

$267,600 + $829,400

$1,097,000

2025

$19,097 (+4.6%)

$267,600 + $829,400

$1,097,000

2024

$18,265 (+2.3%)

$267,600 + $829,400

$1,097,000

2023

$17,852 (+0.6%)

$267,600 + $829,400

$1,097,000

2022

$17,737 (+7.1%)

$267,600 + $829,400

$1,097,000

2021

$16,562 (−36.3%)

$267,600 + $762,400

$1,030,000

2020

$25,997 (+57.2%)

$267,600 + $762,400

$1,030,000

2019

$16,541 (−35.9%)

$267,600 + $762,400

$1,030,000

2018

$25,819 (+78.6%)

$267,600 + $762,400

$1,030,000

2017

$14,460 (+3.0%)

$267,600 + $762,400

$1,030,000

2016

$14,044 (+1.1%)

$197,400 + $673,500

$870,900

2015

$13,886 (+0.9%)

$197,400 + $673,500

$870,900

2014

$13,760

$197,400 + $673,500

$870,900

Tax history for 148 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2026

$19,097

$267,600 + $829,400

$1,097,000

2025

$19,097 (+4.6%)

$267,600 + $829,400

$1,097,000

2024

$18,265 (+2.3%)

$267,600 + $829,400

$1,097,000

2023

$17,852 (+0.6%)

$267,600 + $829,400

$1,097,000

2022

$17,737 (+7.1%)

$267,600 + $829,400

$1,097,000

2021

$16,562 (−36.3%)

$267,600 + $762,400

$1,030,000

2020

$25,997 (+57.2%)

$267,600 + $762,400

$1,030,000

2019

$16,541 (−35.9%)

$267,600 + $762,400

$1,030,000

2018

$25,819 (+78.6%)

$267,600 + $762,400

$1,030,000

2017

$14,460 (+3.0%)

$267,600 + $762,400

$1,030,000

2016

$14,044 (+1.1%)

$197,400 + $673,500

$870,900

2015

$13,886 (+0.9%)

$197,400 + $673,500

$870,900

2014

$13,760

$197,400 + $673,500

$870,900

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

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.89 Acres

Year renovated

—

Sq. Ft.

4,364

Year built

1999

Style

Single Family Residential

County

Greene County

APN

194600A09501000030220000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 25, 2026.

Property details

Parking

Parking/Garage Information
Has Garage
# of Garage Spaces: 1

Interior

Bathroom Information
# of Full Bathrooms: 3
# of Half Bathrooms: 1

Heating & Cooling
Has Heating
Heating: Baseboard, Oil, Radiant

Interior Features
Interior Features: High Speed Internet
Window Features: Insulated Windows
Appliances: Dryer, Disposal, Dishwasher, Microwave, Other, Refrigerator, Washer, Water Heater
Flooring: Carpet, Ceramic Tile, Stone, Tile, Wood
Has Fireplace
# of Fireplaces: 3
Fireplace Features: Family Room, Living Room, Other, Wood Burning

Room Information
# of Rooms Total: 14
Has Basement

Exterior

Exterior Features
Patio And Porch Features: Deck, Porch
Roof: Asphalt

Building Information
Entry Level: 1805
Sq. Ft.: 4364.0
Levels: Two
# of Stories Total: 2
Construction Materials: Frame, Other, Stucco, Wood Siding
Foundation Details: Concrete Perimeter, Slab

Property Features
Has View
Security Features: Security System

Property Information
Property Type: Residential
Property Sub Type: Single Family Residence
Raw Mls Property Sub Type: Single Family Residence
Property Is Attached

Lot Information
Road Surface Type: Paved
Lot Size : 0.89
Lot Size Area: 0.89
Lot Size Units: Acres
Lot Size Acres: 0.89

Utilities

Utility Information
Water Source: Public
Electric: 200+ Amp Service, Underground
Sewer: Public Sewer

Location

HOA Information
Has Homeowners Association
Association Fee: $3,500

Schools Information
High School District: Wind-Ash-Jewett

Location Information
Directions: From South Street turn onto Trailside. At 'T' turn right. House on right.

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 4,364
Stories: 2.0
Lot Size: 0.89 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: —
County: Greene County
APN: 194600A09501000030220000000

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

$1.99M – $2.41M

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New listings for sale in 12496

$525,000

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Home values near 148 Trailside Rd

Data from public records.

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

Address	Redfin Estimate
115 Trailside Road, Windham, NY 4 Beds \| 3.5 Baths \| 2534 Sq. Ft.	$1,217,949
150 Trailside Road, Windham, NY 9 Beds \| 7 Baths \| 6858 Sq. Ft.	$2,332,936

Address	Redfin Estimate
133 Trailside Road, Windham, NY 5 Beds \| 3.5 Baths \| 4536 Sq. Ft.	$1,972,858
151 Trailside Road, Windham, NY 7 Beds \| 4 Baths \| 4300 Sq. Ft.	$1,965,949

Property information provided by HVCRMLS when last listed in 2022. This data may not match . Learn more.

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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 148 Trailside Rd

Tax history for 148 Trailside Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12496

Home values near 148 Trailside Rd

More real estate resources