5 Chalet Drive, Windham, NY 12496
OFF MARKET

5 Chalet Drive
Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 4,208 sqft (on 1.70 acres)

$1,049,800

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $6,682/mo*
Refinance Your Home

$1,049,800

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $6,682/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,208 sqft
(on 1.70 acres)

Local Information

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

Description

This charming country gem in Windham offers breathtaking views of the slopes . Boasting 4 bedrooms and 4.5 baths, this home exudes rustic elegance with its stone walls and firepit, perfect for cozy gatherings or serene evenings under the stars. Inside, you'll find beautiful hardwood floors complemented by a massive stone fireplace adding warmth and character to the living space.Beautiful custom kitchen with SS appliances, granite counters. Ample closet space ensures convenient storage, while the family room and recreation room on the lower, walkout level provide versatile areas for relaxation and entertainment, along with another beautiful fireplace. Nestled just minutes away from the village, slopes, golf courses, and restaurants, this home offers both seclusion and accessibility. Impeccably maintained, it spans over 4000 sq. ft of living space, with decks that invite you to soak in the tranquil surroundings and enjoy the beauty of nature.
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 5 Chalet Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Finished,Full,Walk-Out AccessNumber of Rooms: 10Types of Rooms: Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Other Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4208 Square Feet
Appliances & Utilities
Appliances: Other, Water Heater, Washer, Refrigerator, Range, Dryer, DishwasherDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,PropaneHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Family Room, Living Room, Wood BurningHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Storm Window(s)Flooring: Carpet, Hardwood, Tile
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Tile
View
Has a ViewView: Mountain(s), Trees/Woods

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PorchOther Structures: Shed(s)Foundation: Concrete Perimeter
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Engineered Septic

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Cedar, Frame, Shake Siding, OtherNot Attached Property
Property Information
Parcel Number: 78.00243

Price & Status

Price
List Price: $995,000
Status Change & Dates
Off Market Date: Wed Apr 10 2024

Location

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

Building

Building Area
Building Area: 4208 Square Feet

HOA

No HOA

Lot Information

Lot Area: 1.7 Acres

Miscellaneous

BasementMls Number: 151822
Last check for updates: about 17 hours ago
Listed by Carol Shaw, (518) 322-8831
Shaw Country Realty, Inc.
Bought with: Non Member Firm
Source: HVCRMLS, MLS#151822

Price History for 5 Chalet Drive

DatePriceEventSource
06/17/2024$995,000Sold
HVCRMLS #151822
04/11/2024$995,000ContingentColumbia Greene Northern Dutchess MLS #151822
03/27/2024$995,000PendingColumbia Greene Northern Dutchess MLS #151822
03/14/2024$995,000Listed For SaleColumbia Greene Northern Dutchess MLS #151822
05/18/2012$455,000Sold
N/A
09/02/2010$90,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$915,377
Home facts updated by county records

Comparable Sales for 5 Chalet Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Brook Hollow Lane, Windham, NY
0.45
Single-Family Home
$999,999
03/10/26
3
3.5
3,284
91 Beaver Hill Road, Windham, NY
0.38
Single-Family Home
$755,000
05/01/26
4
3
1,839
73 Beaver Hill Road, Windham, NY
0.54
Single-Family Home
$702,000
12/22/25
4
2.5
2,500
12 Lauren Lane, Windham, NY
0.25
Single-Family Home
$1,709,999
02/09/26
6
4.5
4,855
233 Begley Road, Windham, NY
0.10
Single-Family Home
$795,000
10/27/25
3
2
2,542
19 Brook Hollow Lane, Windham, NY
0.51
Single-Family Home
$639,000
01/30/26
4
2
2,240
8 Evans Road, Windham, NY
0.94
Single-Family Home
$725,000
09/09/25
5
3.5
3,862
317 Mitchell Hollow Road, Windham, NY
0.44
Single-Family Home
$340,000
04/03/26
5
3
2,472

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Chalet Drive.

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 5 Chalet Drive

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Off Market Homes Near 5 Chalet Drive

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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 5 Chalet Drive

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5 Chalet Drive, Windham, NY 12496 is a 4 bedroom, 5 bathroom, 4,208 sqft single-family home built in 2012. This property is not currently available for sale. 5 Chalet Drive was last sold on Jun 17, 2024 for $995,000 (0% higher than the asking price of $995,000). The current Trulia Estimate for 5 Chalet Drive is $1,049,800.