5344 Main St., Windham, NY 12496
Property image
Property image
OFF MARKET

5344 Main St.
Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 6,400 sqft

$1,264,700

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $8,180/mo*
Refinance Your Home

$1,264,700

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $8,180/mo*
Refinance Your Home
3 Beds
3 Baths
6,400 sqft

Local Information

  • Map ViewExplore the area around 5344 Main St..
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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!
5344 Main St., Windham, NY 12496 is a 3 bedroom, 3 bathroom, 6,400 sqft single-family home built in 1975. It last sold for $1,200,000 on Apr 30, 2025 (7% below the $1,295,000 asking price). It is currently off market. The Trulia Estimate is $1,264,700, with a rent estimate of $4,898/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 5344 Main St.

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: FullNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 6400 Square Feet
Appliances & Utilities
Appliances: Water Heater, Electric Water Heater
Heating & Cooling
Heating: OtherHas HeatingHeating Fuel: Other
Fireplace & Spa
No Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Flooring: Other
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Other
View
Has a ViewView: Mountain(s)

Exterior Features

Exterior Home Features
Roof: OtherFoundation: Concrete Perimeter
Frontage
Road Surface Type: Paved
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: OtherAttached To Another Structure
Property Information
Parcel Number: 78.19112

Price & Status

Price
List Price: $1,295,000
Status Change & Dates
Off Market Date: Tue Apr 29 2025

Location

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

Building

Building Area
Building Area: 6400 Square Feet

HOA

No HOA

Lot Information

Lot Area: 7840.8 sqft

Miscellaneous

BasementMls Number: 156927
Last check for updates: about 10 hours ago
Listed by Philippe Uhrik, (518) 528-6186
Win Morrison Realty - Catskill
Bought with: Mary Donovan, Gallagher & Company
Source: HVCRMLS, MLS#156927

Price History for 5344 Main St.

DatePriceEventSource
04/30/2025$1,200,000Sold
HVCRMLS #156927
04/29/2025$1,295,000ContingentColumbia Greene Northern Dutchess MLS #156927
04/29/2025$1,295,000PendingToActiveColumbia Greene Northern Dutchess MLS #156927
04/29/2025$1,295,000ContingentColumbia Greene Northern Dutchess MLS #156927
03/10/2025$1,295,000PriceChange
Columbia Greene Northern Dutchess MLS #154461
02/20/2025$1,300,000PriceChange
Columbia Greene Northern Dutchess MLS #154461
10/16/2024$1,295,000PriceChange
Columbia Greene Northern Dutchess MLS #154461
09/13/2024$1,300,000Listed For SaleColumbia Greene Northern Dutchess MLS #154461
07/01/2024ListingRemovedColumbia Greene Northern Dutchess MLS #150929
05/31/2024$1,350,000ContingentColumbia Greene Northern Dutchess MLS #150929
05/03/2024$1,350,000PendingColumbia Greene Northern Dutchess MLS #150929
03/09/2024$1,350,000PriceChange
Columbia Greene Northern Dutchess MLS #150929
12/13/2023$1,469,000Listed For SaleColumbia Greene Northern Dutchess MLS #150929
10/01/2023ListingRemovedColumbia Greene Northern Dutchess MLS #149858
09/09/2023$1,400,000Listed For SaleColumbia Greene Northern Dutchess MLS #149858
09/07/2023ListingRemovedColumbia Greene Northern Dutchess MLS #147174
07/27/2023$1,400,000Listed For SaleColumbia Greene Northern Dutchess MLS #147174
07/01/2023ListingRemovedOneKey® MLS as distributed by MLS GRID #H6243518
04/20/2023$1,500,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6243518
04/17/2023$1,500PriceChange
OneKey® MLS as distributed by MLS GRID #H6243518
02/09/2023$1,500,000Listed For SaleColumbia Greene Northern Dutchess MLS #145285

Market trends in Windham

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
57
3MoM
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Comparable Sales for 5344 Main St.

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5376 State Route 23, Windham, NY
0.10
Single-Family Home
$540,000
06/29/26
3
2.5
2,448
5287 Route 23, Windham, NY
0.15
Single-Family Home
$680,000
04/28/26
3
2
2,350
17 Mitchell Hollow Road, Windham, NY
0.25
Single-Family Home
$398,000
03/23/26
4
3
1,914
78 Mitchell Hollow Road, Windham, NY
0.40
Single-Family Home
$780,000
03/19/26
3
3.5
2,324
5320 Route 23, Windham, NY
0.06
Single-Family Home
$590,000
04/27/26
8
8
3,712
212 South Street, Windham, NY
0.20
Single-Family Home
$640,000
11/21/25
3
2
2,240
5474 Route 23, Windham, NY
0.40
Single-Family Home
$950,000
06/30/26
7
3
4,281

Nearby homes

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Assigned Schools

These are the assigned schools for 5344 Main St..

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

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Apartments for Rent

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Homes for sale near 5344 Main St.

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Off Market Homes Near 5344 Main St.

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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.