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71 East Main Street

Middletown, Connecticut 06457

PENDING$419,000
Beds
8
Baths
4
SqFt
3,110
Acres
0.15
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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About This Home

Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Multi-Family · Units on different Floors,Other
Year Built
1900
Days on Market
124 days
Beds
8
Baths
4 full
Living Area
3,110 sq ft
Lot Size
0.15 acres
Property Taxes
$7,936 / 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

$419,000

vs $579,900 median

27.7% below median

Price / Sq Ft

$135

vs $131 median

In line with median

Days on Market

124 days

vs 57 days median

67 days longer 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

71 East Main Street, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,072

per month

  • Principal & Interest$2,271
  • Property Taxes$661
  • Insurance$140
  • 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
Other
Style
Units on different Floors,Other
Year Built
1900
New Construction
No/Resale
Living Area
3,110 sq ft

Schools

Elementary
Farm Hill
Middle
Per Board of Ed
High
Middletown

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
None
Basement
FullFully Finished

Exterior & Lot

Lot Size
0.15 acres
Zoning
MXI
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Brick
Color
Brick
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Deck
Lot Description
Level Lot

Listing & Financials

Property Taxes
$7,936 / Annually
Days on Market
124
MLS #
24190092
MLS Status
Under Contract

Similar Properties

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

Listed By

Levi Judqin

(203) 724-7127

Brass Moon Realty

(203) 945-1000

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 2:15 AM UTC.