Welcome to 221 E Main St—a standout investment opportunity offering flexibility, location, and long-term potential in one of Orange County’s most active and rapidly growing markets. This mixed-use property features two residential units and a commercial space on the ground floor, making it an ideal choice for investors, owner-occupants, or entrepreneurs looking to establish a business while generating rental income. The upstairs level includes two well-maintained residential units, each offering bright, comfortable living with strong appeal to long-term tenants. The ground-floor commercial space provides excellent visibility along a well-trafficked stretch of East Main Street, making it a perfect fit for retail, office, or professional services. The first floor is zoned commercial and must remain commercial—buyers are encouraged to confirm all use options with the Middletown Building Department. Additional features include a garage and a central location within walking distance to local shops, restaurants, and community amenities. With easy access to I-84, Route 17, and nearby public transportation, this property is conveniently situated just 70 miles from New York City, making it attractive to both commuters and local professionals. Middletown continues to see significant growth in both its residential and commercial sectors, driven by strong rental demand, revitalization efforts, and regional development. Whether you're seeking a new project with strong income potential or a strategically located property with long-term upside, 221 E Main St offers a rare combination of versatility and value in a market with upward momentum.
For sale
$429,999
221 E Main Street, Middletown, NY 10940
--beds
--baths
2,946sqft
Duplex, Multi Family
Built in 1887
-- sqft lot
$-- Zestimate®
$146/sqft
$-- HOA
What's special
Commercial spaceGround-floor commercial spaceResidential unitsExcellent visibilityBright comfortable living
- 50 days
- on Zillow |
- 382 |
- 34 |
Zillow last checked: 7 hours ago
Listing updated: June 21, 2025 at 02:01am
Listing by:
Century 21 Alliance Rlty Group 845-297-4700,
Savannah Miceli 845-275-9259
Source: OneKey® MLS,MLS#: 880208

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Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Heating
- Forced Air, Other
Cooling
- Central Air
Features
- Other
Interior area
- Total structure area: 2,946
- Total interior livable area: 2,946 sqft
Property
Parking
- Total spaces: 2
- Parking features: Detached, Driveway
- Garage spaces: 2
- Has uncovered spaces: Yes
Details
- Parcel number: 330900.032.0000009011.000/0000
- Special conditions: None
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Duplex, Multi Family
Materials
- Other
- Foundation: Other
Condition
- Year built: 1887
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: See Remarks
Community & HOA
Location
- Region: Middletown
Financial & listing details
- Price per square foot: $146/sqft
- Annual tax amount: $9,848
- Date on market: 6/20/2025
- Listing agreement: Exclusive Right To Sell
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