442 Old Rd, Windham, NY 12496
OFF MARKET

$662,200

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,962 sqft (on 4 acres)

442 Old Rd, Windham, NY 12496

Est. Refi. Payment $4,336/mo*
Refinance Your Home

Home Value

Trulia Estimate
$662K
Since last month
Decreased$600 (-0.1%)
Since last year
Increased$37K (+5.9%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$660K
July 2026$661K
June 2026$659K
May 2026$641K
April 2026$638K
March 2026$603K
February 2026$584K
January 2026$569K
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
415 Old Road, Windham, NY
0.18
Single-Family Home
$730,000
07/17/26
3
3.5
3,279
5 Jacob Strasse Road, Windham, NY
0.62
Single-Family Home
$950,000
03/19/26
4
3
3,245
128 Mount Greenery Road, Windham, NY
0.76
Single-Family Home
$685,000
12/15/25
4
3
2,759
36 Mount Greenery Road, Windham, NY
1.04
Single-Family Home
$575,000
01/28/26
3
2
1,376
530 Old Rd, Windham, NY
0.44
Single-Family Home
$207,000
04/08/26
2
2
1,560
150 Old Rd, Windham, NY
1.34
Single-Family Home
$17,674
11/21/25
5
3
3,474
205 Nauvoo Road Road, Windham, NY
1.53
Single-Family Home
$850,000
10/03/25
4
2
2,200
122 Old Road, Windham, NY
1.48
Single-Family Home
$715,000
11/24/25
4
2.5
1,823
73 Beaver Hill Road, Windham, NY
1.64
Single-Family Home
$702,000
12/22/25
4
2.5
2,500
61 Cambridge Heights Road, Windham, NY
1.42
Single-Family Home
$1,311,000
12/30/25
5
3.5
4,214

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
415 Old Road, Windham, NY 12496
0.18
$730,000
3
3.5
3,279
Recently Sold
73 Cross Road, Windham, NY 12496
0.28
$711,500
3
2
2,792
Off Market
12 Jacob Strasse Road, Windham, NY 12496
0.55
$1,407,200
6
5.5
5,500
Off Market
5 Jacob Strasse Road, Windham, NY 12496
0.62
$950,000
4
3
3,245
Recently Sold
1 Estate View Drive, Windham, NY 12496
0.64
$300,000
-
-
-
For Sale
116 Galway Road, Windham, NY 12496
0.65
$472,500
3
2
1,867
Off Market
120 Mount Greenery Road, Windham, NY 12496
0.67
$600,600
3
3
2,017
Off Market
591 Old Rd, Windham, NY 12496
0.71
$201,200
-
-
-
Off Market
2 Estate View Drive, Windham, NY 12496
0.73
$290,000
-
-
-
For Sale
128 Mount Greenery Road, Windham, NY 12496
0.76
$685,000
4
3
2,759
Recently Sold
18 Saint Johns Pass, Windham, NY 12496
0.76
-
5
2.5
3,690
Off Market
611 Old Road, Windham, NY 12496
0.80
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 442 Old Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
4 acres
Living Area
2,962 sqft
Price/Sqft
$224
Parking
Garage

About this House

This single-family home is located at 442 Old Rd, Windham, NY. 442 Old Rd is in Windham, NY and in ZIP code 12496. This property has 4 bedrooms, 3 bathrooms and approximately 2,962 sqft of floor space. This property has a lot size of 4.00 acres and was built in 1988.
442 Old Rd, Windham, NY 12496 is a 4 bedroom, 3 bathroom, 2,962 sqft single-family home built in 1988. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $662,200, with a rent estimate of $5,937/month.

Home Details for 442 Old Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

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

Community

Units in Building: 1

Lot Information

Lot Area: 4.00 acres

Price and Tax history

YearProperty taxTax assessment
2025Unavailable
$681,948
Home facts updated by county records

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 442 Old Rd

  • What is 442 Old Rd estimated to be worth?
    Trulia's estimated value for 442 Old Rd in Windham, NY is $662,200.
  • 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.
  • What are the closest schools to 442 Old Rd?
    The closest schools to 442 Old Rd in Windham, NY are Windham Ashland Central School (K-12, rated 6/10).
  • How big is the lot at 442 Old Rd?
    The lot at 442 Old Rd in Windham, NY is about 4 acres.
  • Does 442 Old Rd have a garage?
    Yes, 442 Old Rd in Windham, NY has a garage.

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