199 Old Rd, Windham, NY 12496
OFF MARKET

199 Old Rd
Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 2,816 sqft (on 2.50 acres)

$796,400

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $5,067/mo*
Refinance Your Home

$796,400

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $5,067/mo*
Refinance Your Home
4 Beds
3 Baths
2,816 sqft
(on 2.50 acres)

Local Information

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

Description

Huge price cut! Authentic Timber Frame ski house exemplifies exceptional warmth and enduring quality. Post and beam construction of mortise and tendon joinery showcases towering strength and beauty of Northern Pine woods. Great room is anchored by an impressive floor to ceiling blue stone fireplace with open concept flow of the main common areas which also shares access to large back deck that has lovely mountain views of Windham Mt. ski slopes. Main floor Master allows you to live on one level in all stages of your life while providing comfortable space for family and extended guests on the lower level complete with ensuite, kids bunk room and 4th bedroom, another living room and bonus family room allows you to spread out quite nicely. Split air condition and pellet stove were added for year-round comfort and efficiency. 2.5 acre parcel is an even balance of open lawn surrounded by woods ensures privacy yet 2 minutes to the center of Windham village- Nice!
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
No Info
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 199 Old Rd

Interior Features

Interior Details
BasementTypes of Rooms: Dining Room
Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPorch

Property Information

Year Built
Year Built: 1981Year Updated: 1986
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 2.50 acres

Price History for 199 Old Rd

DatePriceEventSource
06/10/2019$500,000Sold
HVCRMLS #123783
04/04/2019$539,000PendingAgent Provided
01/07/2019$539,000PriceChange
Agent Provided
10/25/2018$579,900Listed For SaleAgent Provided
02/01/2013$282,500Sold
N/A
12/28/2012$282,500Sold
HVCRMLS #20123088
10/21/2012$349,000PriceChange
Agent Provided
09/13/2012$379,000PriceChange
Agent Provided
06/15/2012$399,800Listed For SaleAgent Provided
03/26/2012$298,722Sold
N/A
07/10/2007$372,500Sold
N/A
10/10/1997$165,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$850,048
Home facts updated by county records

Comparable Sales for 199 Old Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
122 Old Road, Windham, NY
0.38
Single-Family Home
$715,000
11/24/25
4
2.5
1,823
92 N Ridge Exd, Windham, NY
0.47
Single-Family Home
$927,000
08/15/25
4
3
3,104
4992 State Route 23, Windham, NY
0.56
Single-Family Home
$400,000
01/27/26
3
2.5
2,400
4992 Ny-23, Windham, NY
0.56
Single-Family Home
$400,000
12/30/25
3
2.5
1,812
61 Cambridge Heights Road, Windham, NY
0.39
Single-Family Home
$1,311,000
12/30/25
5
3.5
4,214
150 Old Rd, Windham, NY
0.23
Single-Family Home
$17,674
11/21/25
5
3
3,474
73 Beaver Hill Road, Windham, NY
0.96
Single-Family Home
$702,000
12/22/25
4
2.5
2,500
128 Mount Greenery Road, Windham, NY
0.84
Single-Family Home
$685,000
12/15/25
4
3
2,759
5 Jacob Strasse Road, Windham, NY
0.80
Single-Family Home
$950,000
03/19/26
4
3
3,245
116 Galway Road, Windham, NY
0.76
Single-Family Home
$450,000
05/23/25
3
2
1,867

Assigned Schools

These are the assigned schools for 199 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 199 Old Rd

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Off Market Homes Near 199 Old Rd

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Homes for rent near 199 Old Rd

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199 Old Rd, Windham, NY 12496 is a 4 bedroom, 3 bathroom, 2,816 sqft single-family home built in 1981. This property is not currently available for sale. 199 Old Rd was last sold on Jun 10, 2019 for $500,000. The current Trulia Estimate for 199 Old Rd is $796,400.