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5344 Main St., Windham, NY 12496

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For Sale

$1,295,000

3 beds • 3 baths • 6,400 sqft

Estimated Payment

$ 6,651 /mo. †

6.65% APR for 30 yrs.
$0 in taxes
Change Loan Terms

  • Single Family Detached
    Property type

  • $202.34
    Price per square foot

  • 41-50 Years Old
    Age

  • Basement
    Rooms

Explore this Property

One of the most iconic pieces of Real Estate in Windham, New York is Back on the Market!! Seller Financing Available! Nestled in the Heart of Windham on bustling Main Street, this unique mixed-use property offers a blend of commercial & retail opportunity plus income generating apartments. The perfect investment that is fully rented and generating great returns that could easily carry a financing element! A community staple that houses The Main Street Market, formerly Todaro's, plus 3 additional 1 Bedroom 1 Bath Apartments upstairs. Situated on Main Street, this building benefits from high visibility and foot traffic, ideal for any retail business looking to thrive in a vibrant community setting. Whether you continue its current successes or attempt a new venture, the possibilities are endless. The ground floor features a spacious retail area, perfect for a variety of businesses. The space is designed to attract both locals and the influx of tourists Windham sees throughout the year. Above the retail space lie three spacious apartments that have been rented for years. This property presents an excellent opportunity for investors looking for dual income streams. The rental potential from both the retail and residential components ensures a steady cash flow, with the added benefit of appreciation in a sought-after location. With the right vision, there's potential for expansion or modification. The property could be an ideal candidate for those looking to add their personal touch or capitalize on Windham's growing popularity. The property being mixed-use, offers flexibility in how the space can be utilized. Have it be owner / operator and live upstairs or just rent of all 4 spaces and generate great monthly cash flow, the choice is yours. The building not only serves as a community hub but also as a cultural landmark on Main Street. This property on Main Street, Windham, is more than just a building; it's an opportunity to own a piece of a thriving small town. Whether you're looking to start or expand a business, invest in real estate, or find a unique place to call home, this property offers the best of both worlds. Contact us today to arrange a viewing and explore the possibilities this gem on Main Street has to offer. There's an additional back lot not included in the sale but can be if interested that's already subdivided as a blank canvas ready to build another retail or residential structure with access Municipal Water & Sewer!
MLS# 154461

Courtesy Of Win Morrison Realty

3391144

Property Features

  • Age
    41-50 Years Old
  • Architecture Style
    Other
  • Lot Size
    0.18 Acres
  • Rooms
    Basement
  • View Type
    Mountain

Map and Directions

Directions to 5344 Main St., Windham, NY 12496

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Mortgage Calculator

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Monthly Payment Breakdown

  • Principle and Interest
    $6,651
  • Property Taxes
    $0
  • Hazard Insurance
    $0
  • Private Mortgage Insurance
    $0
  • HOA Dues
    $0
  • Total Monthly Payment:
    $6,651

Calculators provided for estimating purposes only. Consult with your lender to determine precise payment requirements.

Schools

Windham Ashland Central School

Grades KG-12 Public School

Windham, NY 12496 0.2 miles
5411 state route 23

301 total students
9:1 Student teacher ratio

School Rating: B+

School Details

School information does not guarantee enrollment. School service boundaries are provided as a reference only, may change, and are not guaranteed to be accurate. Contact the school district directly to verify school enrollment eligibility.

Local area information for Windham, NY 12496

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Windham, NY 12496

This community’s employment is highest in the food and administrative support industries. The area’s overall household expenses are above the national average.

78° July
Hottest Average Month
10° February
Coldest Average Month
755 Total Households in Area
-0.6% Increase in population since the year 2010
23.7%
of households
have children
19 minutes
Median Commute Time

Household Expenses vs National Average

This location’s average annual expenditures by category compared to the national average. Index score (100=National Average)

Demographic facts
for Windham, NY 12496

Windham, NY 12496 has a population of 1,702 people in 755 households with a median age of 49.9 years old.

-0.6%
Decrease in population
since the year 2010
Population is Trending down
778
Total households as of 2010
1.4%
projected percent change in total
households in 5 years

Community Population By Age

The median age for this area is 49.9 years old. The smallest percentage group is 55-64 years and the largest percentage is the 85+ years age range.

Community Population By Ethnicity

White 87%
Hispanic 7%
Other 2%
Black 2%
Asian 2%
Native American <1%
The most prevalent ethnicity is White at 87%, followed by Hispanic at 7%, Other at 2%, and Black at 2%.

Economics
for Windham, NY 12496

39 /sq mi
Population Density
$68,745 /yr
Median Household Income
$240,000
Median Sales Price
19 min
Median Commute Time

Household Expenses vs National Average

This location’s average annual expenditures by category compared to the national average. Index score (100=National Average)

Household by Income

Out of the households in this area, the largest income group is $75-99,999k representing 20.44% of the households.

Transportation to Work

  • Drive 78%
  • Work from Home 12%
  • Walk or Bike 9%
  • Public Transit 1%

Occupancy by Type

Vacant 1,402 65%
Owned 680 32%
Rented 74 3%

White vs Blue Collar Jobs







White Collar 80%
Blue Collar 20%

Family & Education Facts
for Windham, NY 12496

49.9 Median Age

Average Household Size

2.3
persons per
household

57.8%

Married Households

Community Population By Education

High School Graduate 32%
Some College 19%
Bachelors Degree 14%
Graduate Degree 14%
Some High School 11%
Associates Degree 10%
Of the total people surveyed, the most prevalent educational attainment level is High School Graduate, representing 32.15% of the population.

Household Family Expenses vs National Average

This location’s average annual expenditures compared to the national average. Index score (100=National Average)
23.7% of households have children

Weather
for Windham, NY 12496

The weather for this area ranges from a high of 78° F in July to a low of 10° F in February

78° July
Hottest Average Month
10° February
Coldest Average Month

Average Temperature by Month

Low (°F)
High (°F)
Jan
10°
31°
Feb
10°
32°
Mar
18°
41°
Apr
30°
53°
May
40°
65°
Jun
49°
73°
Jul
53°
78°
Aug
51°
76°
Sep
45°
69°
Oct
34°
58°
Nov
27°
46°
Dec
15°
34°

Average Temperature in Degrees Fahrenheit

Precipitation

Precipitation (inch)

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Copyright © 2025 Columbia Greene and Northern Dutchess MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is 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. Information being provided is 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.

Data powered by Attom Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.

This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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