277 State Route 296, Windham, NY 12496
OFF MARKET

$351,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,500 sqft (on 0.46 acres)

277 State Route 296, Windham, NY 12496

Est. Refi. Payment $2,414/mo*
Refinance Your Home
Currently Off Market - Sold May 15, 2015 for $145,000

Home Value

Trulia Estimate
$352K
Since last month
Decreased$6K (-1.8%)
Since last year
Increased$9K (+2.6%)
Since last sale
Increased$205K (+141.1%)
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 +128% in the last 10 years
MonthEstimated value
2026
September 2026$350K
August 2026$352K
July 2026$356K
June 2026$359K
May 2026$355K
April 2026$347K
March 2026$344K
February 2026$336K
January 2026$335K
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
366 State Route 296, Windham, NY
0.43
Single-Family Home
$145,920
04/14/26
3
2
1,456
384 Route 296, Windham, NY
0.48
Single-Family Home
$150,000
02/24/26
3
1.5
1,200
384 State Route 296, Windham, NY
0.48
Single-Family Home
$150,000
03/16/26
3
2
1,190
357 State Route 296, Windham, NY
0.45
Single-Family Home
$100,000
07/23/26
4
1.5
2,290
183 County Route 65, Hensonville, NY
0.53
Single-Family Home
$585,000
02/13/26
3
2
2,879
57 Chase Dr, Windham, NY
0.84
Single-Family Home
$375,000
12/18/25
2
3
1,260
216 New York 296, Windham, NY
0.32
Single-Family Home
$999,000
08/07/26
3
2.5
2,342
4992 Ny-23, Windham, NY
0.66
Single-Family Home
$400,000
12/30/25
3
2.5
1,812
4992 State Route 23, Windham, NY
0.66
Single-Family Home
$400,000
01/27/26
3
2.5
2,400
183 County Road 65, Windham, NY
0.53
Single-Family Home
$585,000
12/22/25
5
3
2,644

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
320 State Route 296, Windham, NY 12496
0.22
$598,000
3
1.5
1,718
For Sale
18 East Road #1, Hensonville, NY 12439
0.25
$305,000
2
2
1,192
Off Market
23 - 2 West Wind Drive, Hensonville, NY 12439
0.25
$278,500
2
2
1,192
Off Market
0 West Wind Estates #18-1, Hensonville, NY 12439
0.28
$266,500
2
2
1,200
Off Market
14 Martin Ln, Hensonville, NY 12439
0.31
$272,600
3
2
1,152
Off Market
333 Route 296, Hensonville, NY 12439
0.29
$765,000
7
6
3,135
Off Market
216 New York 296, Windham, NY 12496
0.32
$999,000
3
2.5
2,342
Recently Sold
216 Route 296, Windham, NY 12496
0.32
$920,600
3
2.5
2,342
Off Market
6 Martin Lane, Windham, NY 12496
0.33
$713,800
3
3.5
2,000
Off Market
31 - #2 West Wind Drive, Hensonville, NY 12439
0.32
$209,300
2
2
1,192
Off Market
STATE RT 296, Windham, NY 12496
0.34
-
-
-
-
Off Market
226 State Route 296, Windham, NY 12496
0.35
$6,500,000
16
17.5
10,000
For Sale

Local Information

  • Map ViewExplore the area around 277 State Route 296.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1935
0.46 acre lot
1,500 sqft
$235/sqft

About this House

Charming Cape just a minute to Golf, Skiing, shops at Windham. Original woodworking throughout and enclosed front porch which brings in the sunlight. Living room has wbs, family room off kitchen (or dining room) which opens to rear deck with nice yard. Original woodwork throughout, Hardwood floors. Full walkout basement.2 bedrooms plus small room (bedroom or office) 2 baths. Nicely maintained.Worth the look Brokered And Advertised By: Shaw Country Realty Listing Agent: Carol Shaw
277 State Route 296, Windham, NY 12496 is a 3 bedroom, 2 bathroom, 1,500 sqft single-family home built in 1935. It last sold for $145,000 on May 15, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $351,800, with a rent estimate of $4,334/month.

Home Details for 277 State Route 296

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 7
Appliances & Utilities
Refrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl

Property Information

Year Built
Year Built: 1935Year Updated: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
May 15, 2015
Source: HVCRMLS #97742
Sold
$145,000
Jan 23, 2015
Source: Agent Provided
ListingRemoved
$149,000
Dec 17, 2014
Source: Agent Provided
PriceChange
$149,000
Price decreased by 12%
Jun 24, 2014
Source: Agent Provided
Listed For Sale
$169,000
Apr 1, 2014
Source: Agent Provided
ListingRemoved
$169,000

Market trends in Windham

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
70
3MoM

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 277 State Route 296

  • What is 277 State Route 296 estimated to be worth?
    Trulia's estimated value for 277 State Route 296 in Windham, NY is $351,800.
  • What is the price history for 277 State Route 296?
    277 State Route 296 in Windham, NY last sold for $145,000 in May 2015.
  • 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.
  • How big is the lot at 277 State Route 296?
    The lot at 277 State Route 296 in Windham, NY is about 0.46 acres (20,038 sq ft).

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