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)

$1,056,600

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $6,891/mo*
Refinance Your Home

$1,056,600

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $6,891/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,208 sqft
(on 1.70 acres)

Home Value

Trulia Estimate
$1.06M
Since last month
Increased$900 (+0.1%)
Since last year
Increased$33K (+3.3%)
Since last sale
Increased$62K (+6.3%)
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 +113% in the last 10 years
MonthEstimated value
2026
August 2026$1.06M
July 2026$1.06M
June 2026$1.07M
May 2026$1.05M
April 2026$1.04M
March 2026$1.05M
February 2026$1.02M
January 2026$1.03M
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
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

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
0 Chalet Drive, Windham, NY 12496
0.00
$999,300
4
3.5
3,700
Off Market
16 Chalet Drive, Windham, NY 12496
0.09
-
4
3
3,360
Off Market
233 Begley Road, Windham, NY 12496
0.10
$795,000
3
2
2,542
Recently Sold
38 Chalet Dr, Windham, NY 12496
0.20
$1,191,200
4
4.5
4,300
Off Market
12 Lauren Lane, Windham, NY 12496
0.25
$1,709,999
6
4.5
4,855
Recently Sold
315 Begley Road, Windham, NY 12496
0.29
$325,000
3
1.5
1,152
For Sale
282 Mitchell Hollow, Windham, NY 12496
0.33
$983,800
4
4
3,100
Off Market
36 - 2 Holiday Court #2, Windham, NY 12496
0.35
$486,300
3
3
1,600
Off Market
296 Mitchell Hollow Rd, Windham, NY 12496
0.36
$439,400
3
1
1,486
Off Market
333 Begley Road, Windham, NY 12496
0.36
$300,000
3
2
1,568
Recently Sold
275 Mitchell Hollow Road, Windham, NY 12496
0.40
$297,000
3
1
900
Off Market

Local Information

  • Map ViewExplore the area around 5 Chalet Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2012
Lot Size
1.7 acres
Living Area
4,208 sqft
Price/Sqft
$251
HOA
None

About this House

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.
5 Chalet Drive, Windham, NY 12496 is a 4 bedroom, 5 bathroom, 4,208 sqft single-family home built in 2012. It last sold for the $995,000 asking price on Jun 17, 2024. It is currently off market. The Trulia Estimate is $1,056,600, with a rent estimate of $7,916/month.
Last check for updates: about 10 hours ago
Listed by Carol Shaw, (518) 322-8831
Shaw Country Realty, Inc.
Bought with: Non Member Firm
Source: HVCRMLS, MLS#151822

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

Price and Tax history

DateEventPrice
Jun 17, 2024
Source: HVCRMLS #151822
Sold
$995,000
Apr 11, 2024
Source: Columbia Greene Northern Dutchess MLS #151822
Contingent
$995,000
Mar 27, 2024
Source: Columbia Greene Northern Dutchess MLS #151822
Pending
$995,000
Mar 14, 2024
Source: Columbia Greene Northern Dutchess MLS #151822
Listed For Sale
$995,000
May 18, 2012
Source: N/A
Sold
$455,000

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

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.

Frequently asked questions about 5 Chalet Drive

  • What is 5 Chalet Drive estimated to be worth?
    Trulia's estimated value for 5 Chalet Drive in Windham, NY is $1,056,600.
  • What is the price history for 5 Chalet Drive?
    5 Chalet Drive in Windham, NY last sold for $995,000 in June 2024.
  • 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.
  • Does 5 Chalet Drive have laundry facilities?
    Yes, 5 Chalet Drive in Windham, NY has in-unit laundry.
  • How big is the lot at 5 Chalet Drive?
    The lot at 5 Chalet Drive in Windham, NY is about 1.7 acres.

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