148 Trailside Rd, Windham, NY 12496
OFF MARKET

148 Trailside Rd
Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 4,250 sqft (on 0.89 acres)

$2,049,200

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $13,293/mo*
Refinance Your Home

$2,049,200

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $13,293/mo*
Refinance Your Home
5 Beds
3.5 Baths
4,250 sqft
(on 0.89 acres)

Home Value

Trulia Estimate
$2.05M
Since last month
Decreased$30K (-1.4%)
Since last year
Increased$24K (+1.2%)
Since last sale
Increased$294K (+16.8%)
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 +82% in the last 10 years
MonthEstimated value
2026
August 2026$2.04M
July 2026$2.07M
June 2026$2.09M
May 2026$2.06M
April 2026$2.01M
March 2026$1.99M
February 2026$1.93M
January 2026$1.9M
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
150 Trailside Road, Windham, NY
0.02
Single-Family Home
$1,810,000
03/05/26
9
7
6,859
4 The Loop, Windham, NY
0.44
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
7 Meadow Ln, Windham, NY
0.82
Single-Family Home
$1,200,000
06/16/26
5
4
3,752
7 Meadow Lane, Windham, NY
0.82
Single-Family Home
$1,200,000
06/08/26
5
5.5
3,752
209 Club Road, Windham, NY
0.79
Single-Family Home
$3,000,000
08/07/26
6
5
5,000
219 Club Road, Windham, NY
0.79
Single-Family Home
$3,100,000
05/05/26
6
5
5,021
5474 Route 23, Windham, NY
0.79
Single-Family Home
$950,000
06/30/26
7
3
4,281
5370 State Route 23, Windham, NY
0.73
Single-Family Home
$200,000
10/31/25
4
2
5,248
212 South Street, Windham, NY
0.60
Single-Family Home
$640,000
11/21/25
3
2
2,240

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
135 Trailside Road #135, Windham, NY 12496
0.06
$1,702,200
4
3.5
3,588
Off Market
150 Trailside Road, Windham, NY 12496
0.02
$1,810,000
9
7
6,859
Recently Sold
0 Trailside Drive, Windham, NY 12496
0.04
-
-
-
-
Off Market
6 White Way, Windham, NY 12496
0.09
$3,649,000
5
7
5,532
For Sale
6 White Way #6, Windham, NY 12496
0.09
$3,174,000
6
6
6,207
Off Market
8 White Way #8, Windham, NY 12496
0.12
$2,346,600
5
5
3,772
Off Market
3 Twin Maples #3, Windham, NY 12496
0.13
$1,230,500
4
3.5
2,896
Off Market
0 Twin Maples, Windham, NY 12496
0.13
-
-
-
-
Off Market
6 Twin Maples, Windham, NY 12496
0.14
-
-
-
-
Off Market
16 White Way, Windham, NY 12496
0.15
$2,300,000
5
4.5
4,069
For Sale
2 Twin Maples Lane, Windham, NY 12496
0.14
$399,000
-
-
-
For Sale
8 Twin Maples, Windham, NY 12496
0.16
-
3
2
2,000
Off Market

Local Information

  • Map ViewExplore the area around 148 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
0.89 acres
Living Area
4,250 sqft
Price/Sqft
$482
Parking
Garage

About this House

This single-family home is located at 148 Trailside Rd, Windham, NY. 148 Trailside Rd is in Windham, NY and in ZIP code 12496. This property has 5 bedrooms, 4 bathrooms and approximately 4,250 sqft of floor space. This property has a lot size of 0.89 acres and was built in 1999.
148 Trailside Rd, Windham, NY 12496 is a 5 bedroom, 4 bathroom, 4,250 sqft single-family home built in 1999. It last sold for $1,750,000 on Jun 23, 2022. It is currently off market. The Trulia Estimate is $2,049,200, with a rent estimate of $7,912/month.

Home Details for 148 Trailside Rd

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

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 Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.89 acres

Price and Tax history

DateEventPrice
Jun 23, 2022
Source: HVCRMLS #141031
Sold
$1,750,000
Apr 11, 2022
Source: Columbia Greene Northern Dutchess MLS #141031
Contingent
$1,999,000
Mar 4, 2022
Source: Columbia Greene Northern Dutchess MLS #141031
Listed For Sale
$1,999,000
May 14, 2013
Source: N/A
Sold
$1,100,000
Apr 22, 1998
Source: N/A
Sold
$102,500

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

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

Frequently asked questions about 148 Trailside Rd

  • What is 148 Trailside Rd estimated to be worth?
    Trulia's estimated value for 148 Trailside Rd in Windham, NY is $2,049,200.
  • What is the price history for 148 Trailside Rd?
    148 Trailside Rd in Windham, NY last sold for $1,750,000 in June 2022.
  • 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 148 Trailside Rd?
    The lot at 148 Trailside Rd in Windham, NY is about 0.89 acres (38,768 sq ft).
  • Does 148 Trailside Rd have a garage?
    Yes, 148 Trailside Rd in Windham, NY has a garage.

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