29 Chalet Dr, Windham, NY 12496
Property image
Property image
OFF MARKET

29 Chalet Dr
Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,453 sqft (on 2.40 acres)

$777,400

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $5,089/mo*
Refinance Your Home

$777,400

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $5,089/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,453 sqft
(on 2.40 acres)

Home Value

Trulia Estimate
$777K
Since last month
Decreased$4K (-0.5%)
Since last year
Decreased$4K (-0.5%)
Since last sale
Increased$362K (+87.9%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$774K
July 2026$778K
June 2026$788K
May 2026$771K
April 2026$762K
March 2026$752K
February 2026$745K
January 2026$733K
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
19 Brook Hollow Lane, Windham, NY
0.33
Single-Family Home
$639,000
01/30/26
4
2
2,240
233 Begley Road, Windham, NY
0.10
Single-Family Home
$795,000
10/27/25
3
2
2,542
317 County Route 21, Windham, NY
0.30
Single-Family Home
$340,000
05/07/26
5
3
2,472
317 Mitchell Hollow Road, Windham, NY
0.30
Single-Family Home
$340,000
04/03/26
5
3
2,472
39 Brook Hollow Lane, Windham, NY
0.36
Single-Family Home
$820,000
07/16/26
3
2
2,049
27 Diane Dr, Windham, NY
0.46
Single-Family Home
$620,000
07/22/26
4
2.5
2,800
91 Beaver Hl, Windham, NY
0.56
Single-Family Home
$755,000
05/08/26
3
3
1,839
20 Brook Hollow Lane, Windham, NY
0.27
Single-Family Home
$999,999
03/10/26
3
3.5
3,284
91 Beaver Hill Road, Windham, NY
0.56
Single-Family Home
$755,000
05/01/26
4
3
1,839
73 Beaver Hill Road, Windham, NY
0.72
Single-Family Home
$702,000
12/22/25
4
2.5
2,500

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
38 Chalet Dr, Windham, NY 12496
0.06
$1,191,200
4
4.5
4,300
Off Market
233 Begley Road, Windham, NY 12496
0.10
$795,000
3
2
2,542
Recently Sold
16 Chalet Drive, Windham, NY 12496
0.14
-
4
3
3,360
Off Market
282 Mitchell Hollow, Windham, NY 12496
0.15
$983,800
4
4
3,100
Off Market
12 Lauren Lane, Windham, NY 12496
0.17
$1,709,999
6
4.5
4,855
Recently Sold
5 Chalet Drive, Windham, NY 12496
0.18
$1,056,600
4
4.5
4,208
Off Market
0 Chalet Drive, Windham, NY 12496
0.18
$999,300
4
3.5
3,700
Off Market
36 - 2 Holiday Court #2, Windham, NY 12496
0.19
$486,300
3
3
1,600
Off Market
296 Mitchell Hollow Rd, Windham, NY 12496
0.20
$439,400
3
1
1,486
Off Market
275 Mitchell Hollow Road, Windham, NY 12496
0.22
$297,000
3
1
900
Off Market
251 mitchell hollow Road, Windham, NY 12496
0.24
$795,300
5
3
2,482
Off Market
22 Brook Hollow Lane, Windham, NY 12496
0.27
$764,700
4
2
2,842
Off Market

Local Information

  • Map ViewExplore the area around 29 Chalet Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2008
Lot Size
2.4 acres
Living Area
2,453 sqft
Price/Sqft
$317
Parking
Garage

About this House

This beautiful three bedroom three bath country contemporary is privately nestled at the end of a cul-e sac surrounded by nature. Enjoy cooking in the generous kitchen or relaxing after a long day on the ski slopes in the sun-drenched great room offering wood floors, floor to ceiling wall of glass and fireplace. Master en-suite offers romantic fireplace, jetted soaking tub and a large walk-in closet. The second floors boasts two additional bedrooms, one with private balcony, full bath and a tremendous loft space that currently serves as a sitting area and office. This area could easily be used add sleeping to accommodate multiple families using the home at once. The finished basement offers a family/rec room and large slate tiled mud/ski/laundry room. Wonderful location offering privacy and convenience to town, fine dining, skiing, hiking, hunting & antiquing. 5 mins to ski Windham, 15 mins to skiing and festivals at Hunter Mtn, and just over 2 hours from NYC. Price to sell!
29 Chalet Dr, Windham, NY 12496 is a 3 bedroom, 3 bathroom, 2,453 sqft single-family home built in 2008. It last sold for $411,675 on Jun 15, 2017. It is currently off market. The Trulia Estimate is $777,400, with a rent estimate of $6,132/month.

Home Details for 29 Chalet Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Propane ButaneHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Interior Details
Number of Rooms: 11Types of Rooms: Dining Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 2.40 acres

Price and Tax history

DateEventPrice
Jun 15, 2017
Source: HVCRMLS #111609
Sold
$411,675
Apr 14, 2017
Source: Agent Provided
Pending
$439,000
Sep 17, 2016
Source: Agent Provided
Listed For Sale
$439,000
Jun 1, 2016
Source: Agent Provided
ListingRemoved
$469,000
Oct 16, 2015
Source: Agent Provided
Listed For Sale
$469,000

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 29 Chalet Dr

  • What is 29 Chalet Dr estimated to be worth?
    Trulia's estimated value for 29 Chalet Dr in Windham, NY is $777,400.
  • What is the price history for 29 Chalet Dr?
    29 Chalet Dr in Windham, NY last sold for $411,675 in June 2017.
  • 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 29 Chalet Dr?
    The lot at 29 Chalet Dr in Windham, NY is about 2.4 acres.
  • Does 29 Chalet Dr have a garage?
    Yes, 29 Chalet Dr in Windham, NY has a garage.

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