29 Chalet Dr, Windham, NY 12496
OFF MARKET

29 Chalet Dr
Windham, NY 12496

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

$765,400

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $4,884/mo*
Refinance Your Home

$765,400

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $4,884/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,453 sqft
(on 2.40 acres)

Local Information

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

Description

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!
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.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 29 Chalet Dr

DatePriceEventSource
06/15/2017$411,675Sold
HVCRMLS #111609
04/14/2017$439,000PendingAgent Provided
09/17/2016$439,000Listed For SaleAgent Provided
06/01/2016$469,000ListingRemovedAgent Provided
10/16/2015$469,000Listed For SaleAgent Provided
04/02/2015$479,000ListingRemovedAgent Provided
10/02/2014$479,000PriceChange
Agent Provided
04/01/2014$499,000Listed For SaleAgent Provided
05/12/2009$466,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$787,393
Home facts updated by county records

Comparable Sales for 29 Chalet Dr

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 Mitchell Hollow Road, Windham, NY
0.30
Single-Family Home
$340,000
04/03/26
5
3
2,472
296 County Route 21, Windham, NY
0.20
Single-Family Home
$420,000
08/05/25
3
1
1,486
296 Mitchell Hollow Rd, Windham, NY
0.20
Single-Family Home
$420,000
07/14/25
3
1
1,486
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
89 Siam Road, Windham, NY
0.58
Single-Family Home
$550,000
08/08/25
4
1
2,270
46 Cardinal Dr, Windham, NY
0.46
Single-Family Home
$1,100,000
12/11/25
5
3
1,700

Nearby homes

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Assigned Schools

These are the assigned schools for 29 Chalet Dr.

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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Homes for sale near 29 Chalet Dr

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Off Market Homes Near 29 Chalet Dr

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Homes for rent near 29 Chalet Dr

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29 Chalet Dr, Windham, NY 12496 is a 3 bedroom, 3 bathroom, 2,453 sqft single-family home built in 2008. This property is not currently available for sale. 29 Chalet Dr was last sold on Jun 15, 2017 for $411,675. The current Trulia Estimate for 29 Chalet Dr is $765,400.