- – beds
- – baths
- 2,946 sqft
- $145 per sqft
- 1887 build
- – on site
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.
Last checked:
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Last updated Jun 21, 2025
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MLS# 880208 —
The Building
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Year Built:1887
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Basement:false
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Construction Materials:Other
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# of Total Units:2
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Foundation Details:Other
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Building Area Units:Square Feet
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Building Area Total:2946
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Building Area Source:Public Records
Interior
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Interior Features:Other
The Property
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Parcel Number:330900.032.000-0009-011.000/0000
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Property Type:Residential Income
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Property Subtype:Duplex
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Property Attached:false
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Additional Parcels:false
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Waterfront:false
Listing Agent
- Contact info:
- Agent phone:
- (845) 275-9259
- Office phone:
- (845) 297-4700
Taxes
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Tax Year:204
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Tax Source:Municipality
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Tax Annual Amount:9848
The Listing
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Special Listing Conditions:None
Heating & Cooling
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Heating:Natural Gas, Forced Air, Other
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Cooling:Central Air
Utilities
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Sewer:Public Sewer
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Utilities:See Remarks
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Water Source:Public
The Community
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Senior Community:false
Parking
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Parking Features:Detached, Driveway
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Parking Total:2
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Garage:true
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Garage Spaces:2
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Carport:false
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Sale history
Date | Event | Source | Price | % Change |
---|---|---|---|---|
6/20/25
Jun 20, 2025
|
Listed / Active | ONEKEY | $429,999 |