239 Pearl Street
Middletown, Connecticut 06457
- Beds
- 5
- Baths
- 3
- SqFt
- 2,436
- Acres
- 0.09
- Year Built
- 1924
- Property Type
- 3 Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Excellent investment opportunity in Middletown! Conveniently located near downtown Middletown, Wesleyan University, and major commuter routes, this three-family property is ideal for both investors and owner-occupants. Featuring two 2-bedroom units, one 1-bedroom unit, and a detached garage, the property currently has two long-term tenants and one vacant apartment, offering the flexibility to move right in while collecting rental income or operate as a fully rented investment property. A great opportunity to add value and build long-term equity!
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Multi-Family · 3updown - Unit(s) per Floor
- Year Built
- 1924
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 2,436 sq ft
- Lot Size
- 0.09 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,521 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
10
9 under contract
Median List Price
$457,450
10 active listings
Median Closed Price
$377,500
42 sales
Median Days on Market
41
10 active listings
Median $ / Sq Ft
$162
10 active listings
Sale-to-List Ratio
102.9%
42 sales
How this home compares
List Price
$350,000
vs $457,450 median
23.5% below median
Price / Sq Ft
$144
vs $162 median
11.1% below median
Days on Market
0 days
vs 41 days median
41 days fresher than median
Based on 10 active and 42 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of October 18, 2026.
Location
239 Pearl Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$1,939
- Property Taxes$627
- Insurance$117
- 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
- 3 Family
- Style
- 3updown - Unit(s) per Floor
- Year Built
- 1924
- New Construction
- No/Resale
- Living Area
- 2,436 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.09 acres
- Zoning
- RPZ
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Shingle
- Roof
- Asphalt Shingle
- Foundation
- Block
- Lot Description
- N/A
Listing & Financials
- Property Taxes
- $7,521 / Annually
- Days on Market
- 0
- MLS #
- 24215211
- MLS Status
- Coming Soon
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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 10/18/2026. 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 10/18/2026 at 1:10 AM UTC.