5449 Route 23, Windham, NY 12496
OFF MARKET

$540,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,360 sqft

5449 Route 23, Windham, NY 12496

Est. Refi. Payment $3,574/mo*
Refinance Your Home
Currently Off Market - Sold Oct 24, 2019 for $205,000

Home Value

Trulia Estimate
$541K
Since last month
Increased$22K (+4.2%)
Since last year
Increased$110K (+25.2%)
Since last sale
Increased$341K (+166.5%)
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 +166% in the last 10 years
MonthEstimated value
2026
August 2026$546K
August 2026$541K
July 2026$524K
June 2026$532K
May 2026$570K
April 2026$519K
March 2026$485K
February 2026$480K
January 2026$481K
2025
2024
2023
2022
2021
2020
2019

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
5370 State Route 23, Windham, NY
0.25
Single-Family Home
$200,000
10/31/25
4
2
5,248
5376 State Route 23, Windham, NY
0.23
Single-Family Home
$540,000
06/29/26
3
2.5
2,448
212 County Route 12, Windham, NY
0.41
Single-Family Home
$640,000
12/17/25
3
2
2,240
212 South Street, Windham, NY
0.41
Single-Family Home
$640,000
11/21/25
3
2
2,240
45 Indian Heights Rd, Windham, NY
0.28
Single-Family Home
$949,000
11/24/25
3
2
1,800
5287 Route 23, Windham, NY
0.47
Single-Family Home
$680,000
04/28/26
3
2
2,350
355 South Street, Windham, NY
0.38
Single-Family Home
$635,000
04/20/26
2
2
1,438
355 County Route 12, Windham, NY
0.38
Single-Family Home
$635,000
04/22/26
2
2
1,438
17 Mitchell Hollow Road, Windham, NY
0.56
Single-Family Home
$398,000
03/23/26
4
3
1,914
5474 Route 23, Windham, NY
0.10
Single-Family Home
$950,000
06/30/26
7
3
4,281

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
1 E Route 23 #1, Windham, NY 12496
0.08
$220,800
1
1
500
Off Market
4841 - 1-2 Rt 23, Windham, NY 12496
0.08
$371,100
4
-
2,289
Off Market
5433 New York 23, Windham, NY 12496
0.05
$1,599,000
5
3
4,056
For Sale
5433 State Route 23, Windham, NY 12496
0.05
$1,599,000
5
3
-
For Sale
5429 Route 23, Windham, NY 12496
0.07
$799,000
6
3
2,468
For Sale
5429 New York 23, Windham, NY 12496
0.07
$799,000
6
3
2,468
For Sale
5474 Route 23, Windham, NY 12496
0.10
$950,000
7
3
4,281
Recently Sold
0 Indian Heights Rd., Windham, NY 12496
0.13
-
-
-
-
Off Market
24 Vets Road, Windham, NY 12496
0.17
$385,200
3
1.5
1,588
Off Market
25 Vets Road, Windham, NY 12496
0.18
$425,000
4
4
2,950
For Sale
102 Thunderbird Terrace, Windham, NY 12496
0.16
$1,571,126
5
3.5
4,312
Recently Sold
10 Vets Road, Windham, NY 12496
0.18
$425,000
6
2.5
2,251
For Sale

Local Information

  • Map ViewExplore the area around 5449 Route 23.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
2,360 sqft
$229/sqft

About this House

This single-family home is located at 5449 Route 23, Windham, NY. 5449 Route 23 is in Windham, NY and in ZIP code 12496. This property has 3 bedrooms, 2 bathrooms and approximately 2,360 sqft of floor space.
5449 Route 23, Windham, NY 12496 is a 3 bedroom, 2 bathroom, 2,360 sqft single-family home. It last sold for $205,000 on Oct 24, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $540,600, with a rent estimate of $4,983/month.

Home Details for 5449 Route 23

Property Information

Property Type / Style
Property Type: Single Family Home

Price and Tax history

DateEventPrice
Aug 2, 2024
Source: Columbia Greene Northern Dutchess MLS #152702
ListingRemoved
$849,000
May 15, 2024
Source: Columbia Greene Northern Dutchess MLS #152702
Listed For Sale
$849,000
Oct 24, 2019
Source: N/A
Sold
$205,000

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 5449 Route 23

  • What is 5449 Route 23 estimated to be worth?
    Trulia's estimated value for 5449 Route 23 in Windham, NY is $540,600.
  • What is the price history for 5449 Route 23?
    5449 Route 23 in Windham, NY last sold for $205,000 in October 2019.
  • 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.

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