442 Old Rd, Windham, NY 12496
OFF MARKET

442 Old Rd
Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 2,962 sqft (on 5.90 acres)

$463,400

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $2,958/mo*
Refinance Your Home

$463,400

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $2,958/mo*
Refinance Your Home
4 Beds
3 Baths
2,962 sqft
(on 5.90 acres)

Local Information

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

Description

Large contemporary on just under 6 beautiful acres...level very useful land....distant mountain views....pool...large deck...large living room with wood burning fireplace...central vacuum...family room downstairs.....huge Master Suite with jacuzzi tub, stall shower and double sinks closets galore!! House has been neglected over the years and does need some work...Priced to sell....Owner anxious! Included in this sale is lot 79.00-3-53.1. Brokered And Advertised By: Shaw Country Realty Listing Agent: Theresa MacDonald
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 442 Old Rd

Interior Features

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

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

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

Community

Units in Building: 1

Lot Information

Lot Area: 5.90 acres

Price History for 442 Old Rd

DatePriceEventSource
10/23/2015$217,000Sold
N/A
10/28/2014$299,000ListingRemovedAgent Provided
04/15/2014$299,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax
Assessment$42,407
Home facts updated by county records

Comparable Sales for 442 Old Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
530 Old Rd, Windham, NY
0.44
Single-Family Home
$207,000
04/08/26
2
2
1,560
12 Jacob Strasse Road, Windham, NY
0.55
Single-Family Home
$1,350,000
08/08/25
6
5.5
5,500
36 Mount Greenery Road, Windham, NY
1.04
Single-Family Home
$575,000
01/28/26
3
2
1,376
92 N Ridge Exd, Windham, NY
1.45
Single-Family Home
$927,000
08/15/25
4
3
3,104
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
205 Nauvoo Road Road, Windham, NY
1.53
Single-Family Home
$850,000
10/03/25
4
2
2,200
150 Old Rd, Windham, NY
1.34
Single-Family Home
$17,674
11/21/25
5
3
3,474

Nearby homes

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Assigned Schools

These are the assigned schools for 442 Old Rd.

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

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Homes for sale near 442 Old Rd

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Off Market Homes Near 442 Old Rd

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Homes for rent near 442 Old Rd

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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 available for sale. 442 Old Rd was last sold on Oct 23, 2015 for $217,000. The current Trulia Estimate for 442 Old Rd is $463,400.