Does Windham, NY show holiday spirit?

As of early 2026, 95% of users say there's holiday spirit

Is there wildlife in Windham, NY?

As of early 2026, 90% of users say there's wildlife

Is parking easy in Windham, NY?

As of early 2026, 88% of users say parking is easy

Are yards well-kept in Windham, NY?

As of early 2026, 80% of users say yards are well-kept

Is Windham, NY quiet?

As of early 2026, 80% of users say it's quiet

Is a car needed in Windham, NY?

As of early 2026, 79% of users say car is needed

Do residents of Windham, NY plan to stay at least 5 years?

As of early 2026, 71% of users say they plan to stay for at least 5 years

Would people walk alone at night in Windham, NY?

As of early 2026, 68% of users say people would walk alone at night

Is Windham, NY dog-friendly?

As of early 2026, 65% of users say it's dog friendly

Are neighbors friendly in Windham, NY?

As of early 2026, 62% of users say neighbors are friendly

Do kids play outside in Windham, NY?

As of early 2026, 53% of users say kids play outside

Is Windham, NY walkable to grocery stores?

As of early 2026, 47% of users say it's walkable to grocery stores

Are the streets well-lit in Windham, NY?

As of early 2026, 47% of users say streets are well-lit

Are there community events in Windham, NY?

As of early 2026, 40% of users say there are community events

Is Windham, NY walkable to restaurants?

As of early 2026, 37% of users say it's walkable to restaurants

Does Windham, NY have sidewalks?

As of early 2026, 37% of users say there are sidewalks

FOR SALE

4 ACRES

415 Old Road
Windham, NY 12496

3 Beds
3.5 Baths
3,729 sqft (on 4 acres)

$749,000

$799,000

Est. Mortgage $4,707/mo*

Get Pre-Qualified

$749,000

$799,000

Est. Mortgage $4,707/mo*

Get Pre-Qualified

3 Beds

3.5 Baths

3,729 sqft

(on 4 acres)

Local Information

-- mins to

Commute Destination

Description

Don't miss this unique opportunity to establish a year-round retreat in the Catskill Mountains, ideal for hosting family and friends on two separate lots. The grounds offer apple picking, fishing in the pond, and swimming, while children can enjoy outdoor activities and grandparents relax on the upper deck with scenic mountain views—all accessible from your own front yard. In winter, prepare for days on nearby Windham Ski slopes and return to a spacious chalet featuring an open great room with a warm fireplace in the sunken living area. The property includes ample space for holiday gatherings or casual meals at the kitchen island. The main floor consists of two large bedrooms, a full bathroom, laundry facilities, and a half bath adjacent to the kitchen. Upstairs, a primary suite and loft provide additional privacy and comfort.
The sought-after family room is equipped with a supplementary kitchen, wood-burning stove, quality ski furnishings, pool table, dart games, extra office/sleeping space, and another full bathroom. A convenient one-car garage ensures secure late-night arrivals and easy access. The home boasts a new heating system, full-house air conditioning, and high-quality finishes including marble, hardwood and carpet flooring, wood doors and trim, skylights, and vaulted ceilings—creating a true mountain chalet ambiance. Offered furnished and turnkey, this custom-built home has never before been on the market and is ready for its next owners. Located just minutes from Windham Club, it offers access to year-round activities and the potential to become your dream mountain residence.

Home Highlights

Parking

1 Car Garage

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

$201

Listed

180+ days ago

Last check for updates: about 21 hours ago

Listing by: Hunter Windham Real Estate, (518) 965-8439

Laurie Hanenberg

Hunter Windham Real Estate, (518) 965-8439

Dylan Hanenberg

Source: HVCRMLS, MLS#20254472

Also Listed on HVCRMLS.

Home Details for 415 Old Road

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: Finished,Full,Walk-Out AccessNumber of Rooms: 15Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Dining Room, Family Room, Kitchen, Laundry, Living Room, Loft, Office
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 3729 Square Feet
Appliances & Utilities Utilities: Cable Available, Electricity Connected, Phone Available, Water Connected, Underground UtilitiesAppliances: Washer/Dryer, Microwave, Exhaust Fan, Electric Range, DishwasherDishwasherLaundry: Laundry RoomMicrowave
Heating & Cooling Heating: Baseboard,Hot Water,OilHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa Number of Fireplaces: 1Fireplace: Living Room, Masonry, Wood Burning StoveHas a FireplaceNo Spa
Gas & Electric Electric: 200+ Amp ServiceHas Electric on Property
Windows, Doors, Floors & Walls Window: Insulated Windows, Wood FramesDoor: Mirrored Closet Door(s), Sliding DoorsFlooring: Carpet, Hardwood, Marble, Tile
Levels, Entrance, & Accessibility Stories: 2Levels: Three Or MoreFloors: Carpet, Hardwood, Marble, Tile
View Has a ViewView: Mountain(s), Pond
Security Security: Security System

Exterior Features
Exterior Home Features Roof: AsphaltPatio / Porch: Deck, Wrap AroundOther Structures: Shed(s)Exterior: Private YardFoundation: Concrete Perimeter
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Faces Side,Driveway
Frontage Road Surface Type: AsphaltNot on Waterfront
Water & Sewer Sewer: Septic Tank
Finished Area Finished Area (above surface): 2434 Square FeetFinished Area (below surface): 1295 Square Feet

Days on Market
Days on Market: 180+

Property Information
Year Built Year Built: 1988
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Chalet
Building Construction Materials: Batts Insulation, Concrete, Frame, Vinyl SidingNot a New Construction
Property Information Parcel Number: 26.2, 26.1

Price & Status
Price List Price: $749,000Price Per Sqft: $201

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

Agent Information
Listing Agent Listing ID: 20254472

Building
Building Area Building Area: 3729 Square Feet

Community
Not Senior Community

HOA
No HOA

Lot Information
Lot Area: 4 Acres

Offer
Listing Terms: Cash, Conventional

Miscellaneous
BasementMls Number: 20254472Water ViewWater View: PondAbove Grade Unfinished Area: 2434

Price History for 415 Old Road

Date	Price	Event	Source
02/28/2026	$749,000	PriceChange	HVCRMLS #20254472
Price Change $50,000 (-6%)
09/19/2025	$799,000	Listed For Sale	HVCRMLS #20254472

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Property Tax and Assessment

Year	2025
Tax
Assessment	$664,183

Home facts updated by county records

Comparable Sales for 415 Old Road

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
5 Jacob Strasse Road, Windham, NY	0.58	Single-Family Home	$950,000	03/19/26	4	3	3,245
116 Galway Road, Windham, NY	0.49	Single-Family Home	$450,000	05/23/25	3	2	1,867
128 Mount Greenery Road, Windham, NY	0.72	Single-Family Home	$685,000	12/15/25	4	3	2,759
12 Jacob Strasse Road, Windham, NY	0.50	Single-Family Home	$1,350,000	08/08/25	6	5.5	5,500
36 Mount Greenery Road, Windham, NY	0.98	Single-Family Home	$575,000	01/28/26	3	2	1,376
92 N Ridge Exd, Windham, NY	1.27	Single-Family Home	$927,000	08/15/25	4	3	3,104
61 Cambridge Heights Road, Windham, NY	1.25	Single-Family Home	$1,311,000	12/30/25	5	3.5	4,214
205 Nauvoo Road Road, Windham, NY	1.36	Single-Family Home	$850,000	10/03/25	4	2	2,200

Assigned Schools

These are the assigned schools for 415 Old Road.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

Learn more about our methodology.

Claudia H.
Resident
5y ago
"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.
Resident
6y ago
"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.
Resident
7y ago
"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.
Resident
7y ago
"You will see dog owners walking their dogs often. The one thing missing for dogs would be a dog run "
3
Flag
Steven N.
Resident
7y ago
"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
12y ago
"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
12y ago
"Best Place to live, lots of clean air, beautiful scenery, nice people and lots of places to go"
5
Flag

LGBTQ Local Legal Protections

Additional Cost

Laurie Hanenberg, Hunter Windham Real Estate, (518) 965-8439

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.

415 Old Road, Windham, NY 12496 is a 3 bedroom, 4 bathroom, 3,729 sqft single-family home built in 1988. This property is currently available for sale and was listed by HVCRMLS on Sep 19, 2025. The MLS # for this home is MLS# 20254472.

415 Old Road
Windham, NY 12496

$749,000

$749,000

Local Information