5429 Main St, Windham, NY 12496
OFF MARKET

$746,500

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,468 sqft (on 0.39 acres)

5429 Main St, Windham, NY 12496

Est. Refi. Payment $4,887/mo*
Refinance Your Home

Home Value

Trulia Estimate
$747K
Since last month
Decreased$55K (-6.8%)
Since last year
Decreased$65K (-7.9%)
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 +175% in the last 10 years
MonthEstimated value
2026
August 2026$753K
August 2026$747K
July 2026$807K
June 2026$783K
May 2026$733K
April 2026$788K
March 2026$870K
February 2026$735K
January 2026$762K
2025
2024
2023
2021
2020

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
8 Stonewall Lane, Windham, NY
0.00
Single-Family Home
$1,900,000
07/10/26
5
4.5
3,150
407 Mill Street, Windham, NY
0.21
Single-Family Home
$835,000
03/04/26
3
2.5
2,864
64 Case Rd, Windham, NY
1.11
Single-Family Home
$450,000
10/08/25
4
2
1,908
128 Steinmetz Road, Windham, NY
0.88
Single-Family Home
$925,000
04/17/26
5
4
4,022
19 Brook Hollow Lane, Windham, NY
1.37
Single-Family Home
$639,000
01/30/26
4
2
2,240
317 Mitchell Hollow Road, Windham, NY
1.51
Single-Family Home
$340,000
04/03/26
5
3
2,472
317 County Route 21, Windham, NY
1.51
Single-Family Home
$340,000
05/07/26
5
3
2,472
17 Mitchell Hollow Road, Windham, NY
1.84
Single-Family Home
$398,000
03/23/26
4
3
1,914
20 Brook Hollow Lane, Windham, NY
1.41
Single-Family Home
$999,999
03/10/26
3
3.5
3,284
7 Karlstadt Road, Windham, NY
1.52
Single-Family Home
$440,000
07/20/26
4
2
1,008

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
5220 - -7 State Route 23, Windham, NY 12496
0.01
$260,800
2
2
850
Off Market
15 Stonewall Ln, Windham, NY 12496
0.00
$1,891,100
5
4.5
3,150
Off Market
17 Stonewall Ln, Windham, NY 12496
0.00
$1,464,600
3
3.5
2,400
Off Market
0 Boulder Brook, Windham, NY 12496
0.00
$1,136,400
4
3.5
2,422
Off Market
25 - 4C Stonewall Lane, Windham, NY 12496
0.00
$1,751,400
4
3.5
2,700
Off Market
21 - 4A Stonewall Lane, Windham, NY 12496
0.00
$1,773,000
5
4.5
3,148
Off Market
12 - 2C Stonewall Lane, Windham, NY 12496
0.00
$1,747,300
4
3.5
2,700
Off Market
0 - Lot 4 Sky Hill Road, Windham, NY 12496
0.00
$1,096,500
4
3.5
2,471
Off Market
0 undisclosed, Windham, NY 12496
0.00
$1,597,600
3
3.5
3,864
Off Market
350 - Rt296 W Rt296 Road, Windham, NY 12496
0.00
$1,090,300
7
5
3,364
Off Market
274 Brooksburgh Road #48, Windham, NY 12496
0.00
$465,600
4
3.5
2,158
Off Market
274 Brooksburgh Road #44, Windham, NY 12496
0.00
$541,600
4
2.5
1,789
Off Market

Local Information

  • Map ViewExplore the area around 5429 Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1902
0.39 acre lot
2,468 sqft
$302/sqft

About this House

This single-family home is located at 5429 Main St, Windham, NY. 5429 Main St is in Windham, NY and in ZIP code 12496. This property has 4 bedrooms, 3 bathrooms and approximately 2,468 sqft of floor space. This property has a lot size of 0.39 acres and was built in 1902.
5429 Main St, Windham, NY 12496 is a 4 bedroom, 3 bathroom, 2,468 sqft single-family home built in 1902. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $746,500, with a rent estimate of $6,224/month.

Home Details for 5429 Main St

Property Information

Year Built
Year Built: 1902
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
May 11, 2021
Source: Columbia Greene Northern Dutchess MLS
ListingRemoved
Apr 27, 2021
Source: Columbia Greene Northern Dutchess MLS #137104
Pending
$279,000
Apr 20, 2021
Source: Columbia Greene Northern Dutchess MLS #137104
Listed For Sale
$279,000
Mar 5, 2021
Source: Columbia Greene Northern Dutchess MLS #135621
ListingRemoved
$249,000
Feb 22, 2021
Source: Agent Provided
Pending
$249,000

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 5429 Main St

  • What is 5429 Main St estimated to be worth?
    Trulia's estimated value for 5429 Main St in Windham, NY is $746,500.
  • 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.
  • What are the closest schools to 5429 Main St?
    The closest schools to 5429 Main St in Windham, NY are Windham Ashland Central School (K-12, rated 6/10).
  • How big is the lot at 5429 Main St?
    The lot at 5429 Main St in Windham, NY is about 0.39 acres (16,988 sq ft).

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