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Portland Street

Middletown, Connecticut 06457

ACTIVE$1,100,000
Beds
8
Baths
4
SqFt
5,176
Acres
0.35
Year Built
1900
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Exceptional Multi-Family Investment Opportunity in CT! Located in desirable Middletown, this unique property package offers two two-family homes-for a total of four income-producing units-along with a versatile 2,898 sq ft workshop and two additional vacant land parcels. Each residential building offers approximately 1,380 sq ft with new roofs, new windows, upgraded electrical, and modernized plumbing-providing peace of mind for years to come. All properties are connected to natural gas, adding efficiency and convenience. One unit has been fully renovated, supplies to renovate the other units are located in the workshop. The standout feature is the expansive heated workshop with electricity and plumbing already in place, opening the door to endless possibilities-ideal for contractors, hobbyists, storage, or potential additional income use. Set on a combined .25-acre lot, plus two separate parcels (.08 and .02 acres), this offering provides flexibility rarely found * Expand your portfolio with strong rental income potential * Build on the additional lot (buyer to do due diligence) * Or enjoy extra outdoor space as a private side yard. Whether you're an investor looking for solid cash flow or an owner-occupant seeking supplemental income, this property delivers versatility, updates, and long-term value in one compelling package.

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Multi-Family · Units on different Floors,Units are Side-by-Side
Year Built
1900
Days on Market
116 days
Beds
8
Baths
4 full
Living Area
5,176 sq ft
Lot Size
0.35 acres
Property Taxes
$8,719 / Annually

Market Snapshot

The Middletown Market

Multi-Family · trailing 12 months

Median Days on Market

38

10 active listings

Median $ / Sq Ft

$152

10 active listings

Sale-to-List Ratio

103.5%

45 sales

How this home compares

List Price

$1.10M

vs $419,500 median

2.6× the median

Price / Sq Ft

$213

vs $152 median

40.1% above median

Days on Market

116 days

vs 38 days median

78 days longer than median

Based on 10 active and 45 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of July 28, 2026.

Location

Portland Street, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,703

per month

  • Principal & Interest$5,609
  • Property Taxes$727
  • Insurance$367
  • 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,Units are Side-by-Side
Year Built
1900
New Construction
No/Resale
Living Area
5,176 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Baseboard
Heat Fuel
Natural Gas
Cooling
None
Laundry
All Units Have Hook-Ups
Laundry Location
basement and 2nd floor hook ups
Basement
PartialPartial With Hatchway

Exterior & Lot

Lot Size
0.35 acres
Zoning
MXI
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl SidingStucco
Roof
Asphalt ShingleMetal
Foundation
Concrete
Exterior Features
DeckGuttersLighting
Lot Description
Level Lot

Listing & Financials

Property Taxes
$8,719 / Annually
Days on Market
116
MLS #
24163304
MLS Status
Active

Similar Properties

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Listed By

Jamie Smigel

(860) 759-9310

Carl Guild & Associates

(860) 474-3500

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 7:50 AM UTC.