21 Chalet Dr, Windham, NY 12496
OFF MARKET

21 Chalet Dr
Windham, NY 12496

  • 5 Beds
  • 4 Baths
  • 3,960 sqft (on 2.09 acres)

$1,296,700

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $8,216/mo*
Refinance Your Home

$1,296,700

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $8,216/mo*
Refinance Your Home
5 Beds
4 Baths
3,960 sqft
(on 2.09 acres)

Local Information

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

Description

This single-family home is located at 21 Chalet Dr, Windham, NY. 21 Chalet Dr is in Windham, NY and in ZIP code 12496. This property has 5 bedrooms, 4 bathrooms and approximately 3,960 sqft of floor space. This property has a lot size of 2.09 acres and was built in 2018.
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 21 Chalet Dr

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 10
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
Exterior: WoodFoundation Type: Piers
Parking & Garage
GarageParking: Carport, Garage Detached

Lot Information

Lot Area: 2.09 acres

Price History for 21 Chalet Dr

DatePriceEventSource
11/11/2021$1,325,000Sold
HVCRMLS #139167
10/31/2021$1,495,000ContingentColumbia Greene Northern Dutchess MLS #139167
09/29/2021$1,495,000PendingColumbia Greene Northern Dutchess MLS #139167
09/05/2021$1,495,000Listed For SaleColumbia Greene Northern Dutchess MLS #139167
05/03/2019$687,000Sold
N/A
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax
Assessment$1,196,371
Home facts updated by county records

Comparable Sales for 21 Chalet Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Brook Hollow Lane, Windham, NY
0.33
Single-Family Home
$999,999
03/10/26
3
3.5
3,284
12 Lauren Lane, Windham, NY
0.18
Single-Family Home
$1,709,999
02/09/26
6
4.5
4,855
46 Cardinal Dr, Windham, NY
0.46
Single-Family Home
$1,100,000
12/11/25
5
3
1,700
19 Brook Hollow Lane, Windham, NY
0.38
Single-Family Home
$639,000
01/30/26
4
2
2,240
233 Begley Road, Windham, NY
0.06
Single-Family Home
$795,000
10/27/25
3
2
2,542
8 Evans Road, Windham, NY
0.92
Single-Family Home
$725,000
09/09/25
5
3.5
3,862
91 Beaver Hill Road, Windham, NY
0.50
Single-Family Home
$755,000
05/01/26
4
3
1,839
317 Mitchell Hollow Road, Windham, NY
0.34
Single-Family Home
$340,000
04/03/26
5
3
2,472
73 Beaver Hill Road, Windham, NY
0.66
Single-Family Home
$702,000
12/22/25
4
2.5
2,500
61 Cambridge Heights Road, Windham, NY
1.16
Single-Family Home
$1,311,000
12/30/25
5
3.5
4,214

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 21 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Homes for sale near 21 Chalet Dr

Skip to last item
Skip to first item

Off Market Homes Near 21 Chalet Dr

Skip to last item
Skip to first item

Homes for rent near 21 Chalet Dr

Skip to last item
Skip to first item
21 Chalet Dr, Windham, NY 12496 is a 5 bedroom, 4 bathroom, 3,960 sqft single-family home built in 2018. This property is not currently available for sale. 21 Chalet Dr was last sold on Nov 11, 2021 for $1,325,000. The current Trulia Estimate for 21 Chalet Dr is $1,296,700.