390 South Main Street
Middletown, Connecticut 06457
- Beds
- 4
- Baths
- 4
- SqFt
- 3,182
- Acres
- 0.13
- Year Built
- 1998
- Property Type
- 4 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Exceptional value-add investment opportunity in Middletown! This mixed-use property offers two existing residential apartments and a spacious ground-floor retail space with the potential to convert into two additional, larger residential units, creating a four-family investment property. The upper level features two one-bedroom, one-bathroom apartments, each equipped with washer/dryer hookups and electric water heaters. Additional property highlights include oil heating, solar panels serving all units, a newer roof, and ample off-street parking with convenient front, side, and rear driveway access. All existing appliances are included, excluding washers and dryers. The expansive ground-floor retail space presents an excellent opportunity for investors or developers looking to maximize rental income and build equity through conversion. The City of Middletown has provided preliminary verbal feedback indicating that a four-unit residential conversion may be possible, subject to formal application, required approvals, permits, and inspections. Other four-unit residential properties in the surrounding area further demonstrate the neighborhood's multifamily character.
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1998
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 4 full
- Living Area
- 3,182 sq ft
- Lot Size
- 0.13 acres
- Property Taxes
- $8,207 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
7
13 under contract
Median List Price
$579,900
7 active listings
Median Closed Price
$377,500
42 sales
Median Days on Market
57
7 active listings
Median $ / Sq Ft
$131
7 active listings
Sale-to-List Ratio
102.9%
42 sales
How this home compares
List Price
$399,000
vs $579,900 median
31.2% below median
Price / Sq Ft
$125
vs $131 median
In line with median
Days on Market
0 days
vs 57 days median
57 days fresher than median
Based on 7 active and 42 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of November 10, 2026.
Location
390 South Main Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$2,162
- Property Taxes$684
- Insurance$133
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middletown
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Multi-Family
- Subtype
- Quadruplex
- Style
- Units on different Floors
- Year Built
- 1998
- New Construction
- No/Resale
- Living Area
- 3,182 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Basement
- None
Exterior & Lot
- Lot Size
- 0.13 acres
- Zoning
- MXC
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- N/A
Listing & Financials
- Property Taxes
- $8,207 / Annually
- Days on Market
- 0
- MLS #
- 24220282
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/10/2026. This information is provided 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 11/10/2026 at 1:55 AM UTC.