151 Trailside Rd, Windham, NY 12496
Property image
Property image
OFF MARKET

151 Trailside Rd
Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 3,430 sqft (on 0.45 acres)

$1,932,500

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $12,459/mo*
Refinance Your Home

$1,932,500

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $12,459/mo*
Refinance Your Home
4 Beds
3 Baths
3,430 sqft
(on 0.45 acres)

Home Value

Trulia Estimate
$1.93M
Since last month
Decreased$20K (-1%)
Since last year
Increased$112K (+6%)
Since last sale
Increased$272K (+16%)
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 +78% in the last 10 years
MonthEstimated value
2026
August 2026$1.97M
July 2026$1.99M
June 2026$1.99M
May 2026$1.94M
April 2026$1.92M
March 2026$1.86M
February 2026$1.84M
January 2026$1.79M
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
0.40
Single-Family Home
$1,400,000
09/18/25
4
3
2,536
150 Trailside Road, Windham, NY
0.06
Single-Family Home
$1,810,000
03/05/26
9
7
6,859
30 The Loop, Windham, NY
0.52
Single-Family Home
$885,000
12/15/25
5
4
3,100
7 Meadow Ln, Windham, NY
0.79
Single-Family Home
$1,200,000
06/16/26
5
4
3,752
7 Meadow Lane, Windham, NY
0.79
Single-Family Home
$1,200,000
06/08/26
5
5.5
3,752
209 Club Road, Windham, NY
0.77
Single-Family Home
$3,000,000
08/07/26
6
5
5,000
219 Club Road, Windham, NY
0.77
Single-Family Home
$3,100,000
05/05/26
6
5
5,021
5376 State Route 23, Windham, NY
0.72
Single-Family Home
$540,000
06/29/26
3
2.5
2,448
5287 Route 23, Windham, NY
0.82
Single-Family Home
$680,000
04/28/26
3
2
2,350
212 South Street, Windham, NY
0.61
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
0.08
$1,572,000
4
3.5
3,588
Off Market
150 Trailside Road, Windham, NY 12496
0.06
$1,810,000
9
7
6,859
Recently Sold
0 Trailside Drive, Windham, NY 12496
0.03
-
-
-
-
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
8 White Way #8, Windham, NY 12496
0.16
$2,162,000
5
5
3,772
Off Market
3 Twin Maples #3, Windham, NY 12496
0.17
$1,187,100
4
3.5
2,896
Off Market
0 Twin Maples, Windham, NY 12496
0.17
-
-
-
-
Off Market
6 Twin Maples, Windham, NY 12496
0.18
-
-
-
-
Off Market
16 White Way, Windham, NY 12496
0.19
$2,300,000
5
4.5
4,069
For Sale
2 Twin Maples Lane, Windham, NY 12496
0.17
$399,000
-
-
-
For Sale
8 Twin Maples, Windham, NY 12496
0.20
-
3
2
2,000
Off Market

Local Information

  • Map ViewExplore the area around 151 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
1985
Lot Size
0.45 acres
Living Area
3,430 sqft
Price/Sqft
$563
Parking
Garage

About this House

Super location on Windham Mountain, this contemporary ski home brings ease to the snow sport experience w/quick access to the trails & short walk to the base lodge. Light filled & comfortable, you'll find an open concept living area w/vaulted pine ceilings, a genuine stone fireplace, & spacious kitchen w/large island. The multi level home design creates space within the home for 5 bedrooms, a den, 2 family rooms, 3 baths & 2 snow sport rooms, eliminating the need for hallways making efficient use of square footage. Lovely master bedroom w/cathedral ceilings, a Palladian window & private deck. 4 steps down from the living area is a large family room w/wood burning fireplace, a bedroom, office & full bath. Find 3 additional bedrooms & full bath on the next level down & a bonus family room & second ski room on the lowest level. Enjoy amazing sunsets, premium slope access, hiking & mt biking from your back door & cozy nights by the fireplace from this 4 seasons home!
151 Trailside Rd, Windham, NY 12496 is a 4 bedroom, 3 bathroom, 3,430 sqft single-family home built in 1985. It last sold for $1,700,000 on May 25, 2023. It is currently off market. The Trulia Estimate is $1,932,500, with a rent estimate of $7,249/month.

Home Details for 151 Trailside Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price and Tax history

DateEventPrice
May 25, 2023
Source: HVCRMLS #144341
Sold
$1,700,000
Mar 8, 2023
Source: Columbia Greene Northern Dutchess MLS #144341
Contingent
$2,100,000
Mar 7, 2023
Source: Columbia Greene Northern Dutchess MLS #144341
Pending
$2,100,000
Oct 24, 2022
Source: Columbia Greene Northern Dutchess MLS #144341
Listed For Sale
$2,100,000
Apr 1, 2021
Source: Keller Williams
ListingRemoved

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
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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

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Apartments for Rent

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Explore by feature - Air Conditioning

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7 rentals with a washer/dryer in Windham, NY

Homes for sale near 151 Trailside Rd

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Off Market Homes Near 151 Trailside Rd

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Frequently asked questions about 151 Trailside Rd

  • What is 151 Trailside Rd estimated to be worth?
    Trulia's estimated value for 151 Trailside Rd in Windham, NY is $1,932,500.
  • What is the price history for 151 Trailside Rd?
    151 Trailside Rd in Windham, NY last sold for $1,700,000 in May 2023.
  • 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.
  • Does 151 Trailside Rd have laundry facilities?
    Yes, 151 Trailside Rd in Windham, NY has laundry facilities.
  • How big is the lot at 151 Trailside Rd?
    The lot at 151 Trailside Rd in Windham, NY is about 0.45 acres (19,602 sq ft).