Off Market Dec 2017 for $1.7M

$3,196,763

Est. refi paymentEst. refi $6,568/mo

•

5,150

sq ft

142 Trailside Rd, Windham, NY 12496

About this home

Mountain chic and contemporary style come together on Windham Mountain. Just steps away from the slopes this 5,150 square foot home has 6 bedrooms, 5 full bathrooms, a spa, a powder room, a family room with wood burning stove, a wine cellar and a large basement. The living room has a stone fireplace, alder wood paneling on the walls, walnut floors and wood beamed cathedral ceiling. Open kitchen features custom cabinetry, silestone counters and Sub-Zero and Wolf appliances. All bathrooms are outfitted with Dornbracht fixtures, travertine and mosaic stone walls and floors and limestone counters. Home automation system controllighting, heating, security and sound systems and is accessible remotely via iPhone or iPad. A snow-melt system is installed at the front entry. Prime mountain location with panoramic views of Ski Windham and Catskill Mountains. Only two and a half hours away from NYC. Additional Information: Amenities:Guest Quarters,

Single-familyProperty Type

2014Year Built

0.43 acresLot Size

$621Est. Price/Sq.Ft.

Listing by Mirjana Balac • Julia B Fee Sothebys Int. Rlty

Bought with Non Non Member-MLS • Buyer Representation Office

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4702203

Redfin Estimate

$3,196,763

$1.4M since sold in December 2017$224K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 58.2% higher than the average sale price ($2.02M) of 6 comparable homes.

SOLD AUG 7, 2026
$3,000,000
A
6 beds5 baths5,000 sq ft
209 Club Rd, Windham, NY 12496
Listing by Brainard Ridge Management
SOLD MAY 5, 2026
$3,100,000
B
6 beds5 baths5,021 sq ft
219 Club Road Rd, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD JUL 10, 2026
$1,900,000
C
5 beds4.5 baths3,150 sq ft
8 Stonewall Ln, Windham, NY 12496
Listing by Douglas Elliman Real Estate
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 MAY 12, 2026
$1,571,126
E
5 beds3.5 baths4,312 sq ft
102 Thunderbird Terrace Ter, Windham, NY 12496
Listing by Coldwell Banker Village GreenW
SOLD JUN 8, 2026
$1,200,000
F
5 beds5.5 baths3,752 sq ft
7 Meadow Ln, Windham, NY 12496
Listing by Compass Greater NY, LLC

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Earn from this home

Sell

$1,846,184

Est. take-home

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Refinance

Est. cash available

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Rent

$4,374/mo

Redfin rental estimate

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Market trends in 12496, NY

Last updated July 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

93.5%

+0.1% MoM

Median sale price

$680K

$100K MoM

Avg. days on market

158d

36 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 21 HRS AGO
$549,000
3 beds2 baths2,250 sq ft
16 Hickory Hill Rd, Windham, NY 12496
$1,950,000
4 beds3.5 baths3,400 sq ft
22 Club Rd, Windham, NY 12496
$6,500,000
16 beds17.5 baths10,000 sq ft
226 State Route 296, Windham, NY 12496
Listing by Atelier WM LLC
$499,000
2 beds1 bath1,122 sq ft
183 South St, Windham, NY 12496
See all

Provided by Redfin

Sale history for 142 Trailside Rd

Date

Event

Price

HVCRMLS #117397

Dec 8, 2017

Sold

$1,780,000

$346/sq ft

Sep 15, 2017

Listed

$2,199,000

$427/sq ft

Mountain chic and contemporary style come together on Windham Mountain. Just steps away from the slopes this 5,150 square foot home has 6 bedrooms, 5 full bathrooms, a spa, a powder room, a family room with wood burning stove, a wine cellar and a large basement. The living room has a stone fireplace, alder wood paneling on the walls, walnut floors and wood beamed cathedral ceiling. Open kitchen features custom cabinetry, silestone counters and Sub-Zero and Wolf appliances. All bathrooms are outfitted with Dornbracht fixtures, travertine and mosaic stone walls and floors and limestone counters. Home automation system controls lighting, heating, security and sound systems and is accessible remotely via iPhone or iPad. A snow-melt system is installed at the front entry. Prime mountain location with panoramic views of Ski Windham and Catskill Mountains. Only two and a half hours away from NYC. 142trailside.com

OneKey® MLS as Distributed by MLS Grid #H4702203

Dec 8, 2017

Sold

$1,780,000

$346/sq ft

Jan 18, 2017

Listed

$2,199,000

$427/sq ft

HVCRMLS #112872

Dec 22, 2016

Listed

$2,199,000

$427/sq ft

OneKey® MLS as Distributed by MLS Grid #H4503887

Aug 18, 2016

Listing Removed

—

Feb 2, 2015

Listed

$2,575,000

$500/sq ft

OneKey® MLS as Distributed by MLS Grid #H4402878

Jan 28, 2015

Listing Removed

—

Mar 25, 2014

Listed

$2,975,000

$578/sq ft

Global MLS #26108549

Dec 29, 2006

Sold

$1,050,000

$204/sq ft

May 5, 2006

Listed

$1,150,000

$223/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$20,586 (+4.6%)

$228,000 + $954,500

$1,182,500

2024

$19,688 (+2.3%)

$228,000 + $954,500

$1,182,500

2023

$19,243 (+0.6%)

$228,000 + $954,500

$1,182,500

2022

$19,120 (+0.6%)

$228,000 + $954,500

$1,182,500

2021

$19,014

$228,000 + $954,500

$1,182,500

2020

$19,017 (+0.1%)

$228,000 + $954,500

$1,182,500

2019

$18,990 (−0.5%)

$228,000 + $954,500

$1,182,500

2018

$19,085 (+30.8%)

$228,000 + $954,500

$1,182,500

2017

$14,588 (+3.0%)

$228,000 + $954,500

$1,182,500

2016

$14,168 (+1.1%)

$183,200 + $695,400

$878,600

2015

$14,009 (+0.9%)

$183,200 + $695,400

$878,600

2014

$13,881

$183,200 + $695,400

$878,600

Tax history for 142 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2025

$20,586 (+4.6%)

$228,000 + $954,500

$1,182,500

2024

$19,688 (+2.3%)

$228,000 + $954,500

$1,182,500

2023

$19,243 (+0.6%)

$228,000 + $954,500

$1,182,500

2022

$19,120 (+0.6%)

$228,000 + $954,500

$1,182,500

2021

$19,014

$228,000 + $954,500

$1,182,500

2020

$19,017 (+0.1%)

$228,000 + $954,500

$1,182,500

2019

$18,990 (−0.5%)

$228,000 + $954,500

$1,182,500

2018

$19,085 (+30.8%)

$228,000 + $954,500

$1,182,500

2017

$14,588 (+3.0%)

$228,000 + $954,500

$1,182,500

2016

$14,168 (+1.1%)

$183,200 + $695,400

$878,600

2015

$14,009 (+0.9%)

$183,200 + $695,400

$878,600

2014

$13,881

$183,200 + $695,400

$878,600

*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

5.5

Stories

Lot width

—

Lot depth

—

Lot size

0.43 Acres

Year renovated

—

Sq. Ft.

3,805

Year built

1988

Style

Single Family Residential

County

Greene County

APN

194600A09501000030230000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 6, 2026.

Property details

Parking

Parking Information
Parking Features: Driveway

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 1
Fireplace Features: Wood Burning Stove

Heating & Cooling
Cooling: None
Heating: Hot Water, Propane, Radiant

Interior Features
Interior Features: Cathedral Ceiling(s),Formal Dining,First Floor Bedroom,Speakers
Appliances: Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Gas Water Heater
Levels: Three Or More
Patio And Porch Features: Deck

Room Information
Basement YN: Yes
Attic: None
Rooms Total: 10
Basement: Full, Unfinished

Bathroom Information
Bathrooms Full: 5
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Frame, Shingle Siding, Stone, Wood Siding
Security Features: Security System
Waterfront YN: No

Lot Information
Lot Features: Corner Lot, Sloped, Views

Property Information
Stories: 4
Living Area Source: Other
Property Sub Type: Single Family Residence
Property Condition: New Construction

Financial

Tax Information
Tax Year: 2014
Tax Source: Other

Financial Information
Buyer Financing: Cash

Utilities

Utility Information
Electric Company: NYSEG
Sewer: Public Sewer
Utilities: Trash Collection Private

Location

HOA Information
Has Association
Association Fee 2: $3,000
Association Fee Includes: Common Area Maintenance, Snow Removal, Trash

School Information
Elementary School: Contact Agent
Middle Or Junior School: Contact Agent
High School: Contact Agent
High School District: Contact Agent

Location Information
Directions: South Street to #142 Trailside Road (Village East)
County Or Parish: Out of Area

Public facts

Beds: 6
Baths: 5.5
Sq. Ft.: 3,805
Stories: 2.0
Lot Size: 0.43 acres
Style: Single Family Residential
Year Built: 1988
Year Renovated: —
County: Greene County
APN: 194600A09501000030230000000

Home facts updated by county records on May 6, 2026

Around this home

Schools
Places
Transit

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

$3.04M – $3.68M

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New listings for sale in 12496

NEW 21 HRS AGO

$549,000

3 beds2 baths2,250 sq ft

16 Hickory Hill Rd, Windham, NY 12496

$1,950,000

4 beds3.5 baths3,400 sq ft

22 Club Rd, Windham, NY 12496

$6,500,000

16 beds17.5 baths10,000 sq ft

226 State Route 296, Windham, NY 12496

Listing by Atelier WM LLC

$499,000

2 beds1 bath1,122 sq ft

183 South St, Windham, NY 12496

Home values near 142 Trailside Rd

Data from public records.

Address	Redfin Estimate
115 Trailside Rd, Windham, NY 4 Beds \| 3.5 Baths \| 2534 Sq. Ft.	$1,179,556
148 Trailside Rd, Windham, NY 5 Beds \| 3.5 Baths \| 4364 Sq. Ft.	$2,163,685

Address	Redfin Estimate
133 Trailside Rd, Windham, NY 5 Beds \| 3.5 Baths \| 4536 Sq. Ft.	$2,019,111
150 Trailside Rd, Windham, NY 9 Beds \| 7 Baths \| 6858 Sq. Ft.	$2,320,059

Address	Redfin Estimate
153 Trailside Rd, Windham, NY 4 Beds \| 4.5 Baths \| 4616 Sq. Ft.	$1,697,220
151 Trailside Rd, Windham, NY 7 Beds \| 4 Baths \| 4300 Sq. Ft.	$2,074,414

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2017. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 12496, NY

Sale history for 142 Trailside Rd

Tax history for 142 Trailside Rd

Public record

Property details

Around this home

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12496

Home values near 142 Trailside Rd

More real estate resources