225 Pearl Street
Middletown, Connecticut 06457
- Beds
- 6
- Baths
- 3
- SqFt
- 2,991
- Acres
- 0.10
- Year Built
- 1900
- Property Type
- 3 Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Group showing Sunday, 10/11, 12 noon! Fantastic investment opportunity just minutes from Downtown Middletown! This beautifully maintained three-family property offers a great combination of location, condition, and long-term investment potential. All three units offer two large bedrooms. Each unit also enjoys its own private porch or balcony, giving tenants valuable outdoor space. This property has been well cared for with significant updates throughout, including impeccably updated mechanicals, helping take some of the worry out of owning a multifamily property. A three-car detached garage in the rear adds even more value, along with additional off-street parking. Located on a quiet, desirable street close to Downtown Middletown, the property offers easy access to restaurants, shopping, Wesleyan University, major routes, and everything the downtown area has to offer. Whether you're looking to add a solid three-family to your investment portfolio or live in one unit while collecting rent from the other two, this is the type of multifamily property that is getting harder to find. Great location, private outdoor spaces, garage, strong updates, and three income-producing units all in one property. Don't wait on this one-schedule a showing and see the opportunity for yourself!
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Multi-Family · 3updown - Unit(s) per Floor
- Year Built
- 1900
- Days on Market
- 16 days
- Beds
- 6
- Baths
- 3 full
- Living Area
- 2,991 sq ft
- Lot Size
- 0.10 acres
- Garage / Parking
- 3 garage · 5 total
- Property Taxes
- $7,878 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
9
9 under contract
Median List Price
$549,900
9 active listings
Median Closed Price
$377,500
42 sales
Median Days on Market
39
9 active listings
Median $ / Sq Ft
$151
9 active listings
Sale-to-List Ratio
102.9%
42 sales
How this home compares
List Price
$579,900
vs $549,900 median
5.5% above median
Price / Sq Ft
$194
vs $151 median
28.5% above median
Days on Market
16 days
vs 39 days median
23 days fresher than median
Based on 9 active and 42 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of October 10, 2026.
Location
225 Pearl Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$3,212
- Property Taxes$657
- Insurance$193
- 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
- 1900
- New Construction
- No/Resale
- Living Area
- 2,991 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Wall Unit
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.10 acres
- Zoning
- RPZ
- Garage / Parking
- 3 garage spaces5 total parking spacesDetached GaragePavedOff Street ParkingDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Public Water ConnectedPublic Water In Street
- Sewer
- Public Sewer ConnectedPublic Sewer In Street
- Flood Zone
- No
- Construction
- Aluminum
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- BalconySidewalkLighting
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $7,878 / Annually
- Days on Market
- 16
- MLS #
- 24208519
- MLS Status
- Active
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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 10/10/2026. 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 10/10/2026 at 10:35 PM UTC.