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390 South Main Street

Middletown, Connecticut 06457

ACTIVE - NEW$399,000
Beds
4
Baths
4
SqFt
3,182
Acres
0.13
Year Built
1998
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,979

per 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

Homes with a close match in area, property type, and price.

Listed By

Victor Santana

Santana Realty Group LLC

(860) 977-2703

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.