153 Trailside Rd, Windham, NY 12496
OFF MARKET

153 Trailside Rd
Windham, NY 12496

  • 4 Beds
  • 5 Baths
  • 2,688 sqft (on 0.55 acres)

$1,563,400

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $8,000/mo*
Refinance Your Home

$1,563,400

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $8,000/mo*
Refinance Your Home
4 Beds
5 Baths
2,688 sqft
(on 0.55 acres)

Home Value

Trulia Estimate
$1.56M
Since last month
Decreased$43K (-2.6%)
Since last year
Increased$30K (+1.9%)
Since last sale
Increased$1M (+1,232.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +42% in the last 10 years
MonthEstimated value
2026
August 2026$1.57M
July 2026$1.59M
June 2026$1.61M
May 2026$1.59M
April 2026$1.55M
March 2026$1.53M
February 2026$1.48M
January 2026$1.43M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4 The Loop, Windham, NY
0.43
Single-Family Home
$1,400,000
09/18/25
4
3
2,536
30 The Loop, Windham, NY
0.56
Single-Family Home
$885,000
12/15/25
5
4
3,100
150 Trailside Road, Windham, NY
0.05
Single-Family Home
$1,810,000
03/05/26
9
7
6,859
5370 State Route 23, Windham, NY
0.69
Single-Family Home
$200,000
10/31/25
4
2
5,248
5320 Route 23, Windham, NY
0.77
Single-Family Home
$590,000
04/27/26
8
8
3,712
7 Meadow Lane, Windham, NY
0.84
Single-Family Home
$1,200,000
06/08/26
5
5.5
3,752
17 Mitchell Hollow Road, Windham, NY
0.93
Single-Family Home
$398,000
03/23/26
4
3
1,914
7 Meadow Ln, Windham, NY
0.84
Single-Family Home
$1,200,000
06/16/26
5
4
3,752
5376 State Route 23, Windham, NY
0.67
Single-Family Home
$540,000
06/29/26
3
2.5
2,448
5287 Route 23, Windham, NY
0.77
Single-Family Home
$680,000
04/28/26
3
2
2,350

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
0 Trailside Drive, Windham, NY 12496
0.03
-
-
-
-
Off Market
150 Trailside Road, Windham, NY 12496
0.05
$1,810,000
9
7
6,859
Recently Sold
135 Trailside Road #135, Windham, NY 12496
0.11
$1,572,000
4
3.5
3,588
Off Market
6 White Way, Windham, NY 12496
0.13
$3,649,000
5
7
5,532
For Sale
6 White Way #6, Windham, NY 12496
0.13
$3,072,600
6
6
6,207
Off Market
3 Twin Maples #3, Windham, NY 12496
0.13
$1,187,100
4
3.5
2,896
Off Market
0 Twin Maples, Windham, NY 12496
0.13
-
-
-
-
Off Market
11 Whisper Creek Drive #402, Windham, NY 12496
0.16
$1,374,000
4
5
1,812
Off Market
11 Whisper Creek Drive #601B, Windham, NY 12496
0.16
$1,019,000
3
3
1,506
Off Market
11 Whisper Creek Drive #501, Windham, NY 12496
0.16
$828,800
3
3
1,506
Off Market
11 Whisper Creek Drive #106, Windham, NY 12496
0.16
$2,084,000
5
5.5
3,669
Off Market
0 Whisper Creek Drive #305, Windham, NY 12496
0.16
$1,128,200
3
4
1,856
Off Market

Local Information

  • Map ViewExplore the area around 153 Trailside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
0.55 acres
Living Area
2,688 sqft
Price/Sqft
$582
Parking
Garage

About this House

This single-family home is located at 153 Trailside Rd, Windham, NY. 153 Trailside Rd is in Windham, NY and in ZIP code 12496. This property has 4 bedrooms, 5 bathrooms and approximately 2,688 sqft of floor space. This property has a lot size of 0.55 acres and was built in 1999.
153 Trailside Rd, Windham, NY 12496 is a 4 bedroom, 5 bathroom, 2,688 sqft single-family home built in 1999. It last sold for $117,500 on May 19, 1998. It is currently off market. The Trulia Estimate is $1,563,400, with a rent estimate of $7,612/month.

Home Details for 153 Trailside Rd

Interior Features

Interior Details
BasementTypes of Rooms: Recreation Room
Heating & Cooling
Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 0.55 acres

Price and Tax history

DateEventPrice
May 19, 1998
Source: N/A
Sold
$117,500
Jul 31, 1995
Source: N/A
Sold
$146,483

Market trends in Windham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
67
5MoM
Skip to last item
  • Results are loading
Skip to first item

Around this home

What Locals Say about Windham

At least 14 Trulia users voted on each feature.

  • 95 % Say there's holiday spirit

  • 90 % Say there's wildlife

  • 88 % Say parking is easy

  • 80 % Say yards are well-kept

  • 80 % Say it's quiet

  • 79 % Say car is needed

  • 71 % Say they plan to stay for at least 5 years

  • 68 % Say people would walk alone at night

  • 65 % Say it's dog friendly

  • 62 % Say neighbors are friendly

  • 53 % Say kids play outside

  • 47 % Say it's walkable to grocery stores

  • 47 % Say streets are well-lit

  • 40 % Say there are community events

  • 37 % Say it's walkable to restaurants

  • 37 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Claudia H.
    "School parades the primary grade students mid day. The police are out keeping an eye on the children and the fire department gives away hot chocolate and hot dogs!"
    2
    Flag
  • Dan H.
    "Whether you've lived here all your life or if you're just visiting, the people will welcome you and make you feel at home. I encourage people to visit and maybe stay a while. "
    6
    Flag
  • Julissa K.
    "4th of July I can see the parade passing by my house and even fireworks. Winter we have a lot of visitors here because the ski resort. And the summer is always a lot to do including walking in the Windham Path and all the trails around here are just amazing "
    0
    Flag
  • Steven N.
    "You will see dog owners walking their dogs often. The one thing missing for dogs would be a dog run "
    3
    Flag
  • Steven N.
    "It’s a lovely town to walk in with your dog and rumor has it there is a dog run in the town next door. Great trails for walking with your dog as well."
    1
    Flag
  • howardc1
    "I have a vacation condo here. The location is excellent about 3 miles from Ski Windham, and this is one of the very few properties in the area with a swimming pool and two tennis courts. Property management is excellent. Excellent cultural attractions, chamber music performances right in town, jazz and classical performances during the summer in nearby Hunter and Tannersville. "
    1
    Flag
  • Patti
    "Best Place to live, lots of clean air, beautiful scenery, nice people and lots of places to go"
    5
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Windham, NY

Homes for sale near 153 Trailside Rd

Skip to last item
Skip to first item

Off Market Homes Near 153 Trailside Rd

Skip to last item
Skip to first item

Frequently asked questions about 153 Trailside Rd

  • What is 153 Trailside Rd estimated to be worth?
    Trulia's estimated value for 153 Trailside Rd in Windham, NY is $1,563,400.
  • What is the price history for 153 Trailside Rd?
    153 Trailside Rd in Windham, NY last sold for $117,500 in May 1998.
  • Is Windham a buyer's or seller's market?
    Windham is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Windham?
    Residents describe Windham, NY as easy to park in, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Windham, NY.
  • How big is the lot at 153 Trailside Rd?
    The lot at 153 Trailside Rd in Windham, NY is about 0.55 acres (23,958 sq ft).
  • Does 153 Trailside Rd have a garage?
    Yes, 153 Trailside Rd in Windham, NY has a garage.