151 Trailside, Windham, NY 12496
OFF MARKET

151 Trailside
Windham, NY 12496

  • 7 Beds
  • 4 Baths
  • 4,300 sqft (on 0.45 acres)

$1,916,600

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $11,919/mo*
Refinance Your Home

$1,916,600

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $11,919/mo*
Refinance Your Home
7 Beds
4 Baths
4,300 sqft
(on 0.45 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Super location on Windham Mountain, this contemporary ski on/ski off home brings ease to the snow sport experience w/quick access to the trails & short walk to the base lodge. You'll find new hardwood flooring throughout and 4 tasteful and fully renovated bathrooms. Light filled & comfortable, the open concept living area features a vaulted pine ceiling, a genuine stone fireplace, & spacious kitchen w/large island. The multi level home creates space within the home for 7 bedrooms, 4 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, 2 bedrooms and full bath. Find 3 additional bedrooms & full bath on the next level & a bunk room, full bath & second ski room on the lowest level. Other upgrades include a new roof and new asphalt driveway in 2021. Enjoy amazing sunsets, premium slope access, hiking & Mt biking from your back door & cozy nights by the living room fireplace or family room wood burning stove from this 4 seasons home!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 10, 2025

Home Highlights

Parking
No Info
Outdoor
Porch, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 151 Trailside

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Finished,Full,Walk-Out AccessNumber of Rooms: 15Types of Rooms: Bedroom, Bathroom, Den, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 4300 Square Feet
Appliances & Utilities
Appliances: Other, Water Heater, Washer, Refrigerator, Microwave, Dryer, DishwasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Family Room, Living Room, Wood BurningHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Double Pane WindowsFlooring: Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Floors: Ceramic Tile, Hardwood
View
Has a ViewView: Mountain(s), Neighborhood
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PorchFoundation: Slab
Frontage
Road Surface Type: Paved
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Cedar, Frame, OtherNot Attached Property
Property Information
Parcel Number: 95.10317

Price & Status

Price
List Price: $2,100,000
Status Change & Dates
Off Market Date: Wed Mar 08 2023

Location

Direction & Address
City: Windham
School Information
High School District: Wind-Ash-Jewett

Building

Building Area
Building Area: 4300 Square Feet

HOA

Has an HOA

Lot Information

Lot Area: 0.45 acres

Miscellaneous

BasementMls Number: 144341
Last check for updates: about 7 hours ago
Listed by Nina Porter
Past Member
Bought with: Coldwell Banker Village Green
Source: HVCRMLS, MLS#144341

Price History for 151 Trailside

DatePriceEventSource
05/25/2023$1,700,000Sold
HVCRMLS #144341
03/08/2023$2,100,000ContingentColumbia Greene Northern Dutchess MLS #144341
03/07/2023$2,100,000PendingColumbia Greene Northern Dutchess MLS #144341
10/24/2022$2,100,000Listed For SaleColumbia Greene Northern Dutchess MLS #144341
04/01/2021ListingRemovedKeller Williams
01/24/2021$1,275,000Listed For SaleColumbia Greene Northern Dutchess MLS #133284
01/10/2021ListingRemovedHVCRMLS
01/04/2021$1,275,000PendingToActiveHVCRMLS #2003794
12/02/2020$1,275,000PendingAgent Provided
10/13/2020$1,275,000PriceChange
Agent Provided
08/04/2020$1,300,000Listed For SaleAgent Provided
02/20/2004$950,000Sold
N/A
04/22/1994$150,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$2,086,151
Home facts updated by county records

Comparable Sales for 151 Trailside

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 White Way, Windham, NY
0.21
Single-Family Home
$2,250,000
05/15/25
6
6
4,228
150 Trailside Road, Windham, NY
0.06
Single-Family Home
$1,810,000
03/05/26
9
7
6,859
39 White Way, Windham, NY
0.25
Single-Family Home
$999,999
07/03/25
6
4
3,260
4 The Loop, Windham, NY
0.40
Single-Family Home
$1,400,000
09/18/25
4
3
2,536
30 The Loop, Windham, NY
0.52
Single-Family Home
$885,000
12/15/25
5
4
3,100
219 Club Road, Windham, NY
0.77
Single-Family Home
$3,100,000
05/05/26
6
5
5,021
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

Assigned Schools

These are the assigned schools for 151 Trailside.

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

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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Homes for sale near 151 Trailside

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IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes for rent near 151 Trailside

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Off Market Homes Near 151 Trailside

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151 Trailside, Windham, NY 12496 is a 7 bedroom, 4 bathroom, 4,300 sqft single-family home built in 1995. This property is not currently available for sale. 151 Trailside was last sold on May 25, 2023 for $1,700,000 (19% lower than the asking price of $2,100,000). The current Trulia Estimate for 151 Trailside is $1,916,600.