219 Pearl Street
Middletown, Connecticut 06457
- Beds
- 4
- Baths
- 2
- SqFt
- 1,700
- Acres
- 0.11
- Year Built
- 1900
- Property Type
- 2 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
Downtown convenience, classic character, and two-family potential come together at 219 Pearl Street! Wesleyan University is just a few blocks away, and Main Street's restaurants, shops, and local favorites are within walking distance! Russell Library, parks, public transportation, and convenient access to Route 9 add to the appeal. Two apartments on separate floors offer flexibility for investors or owner-occupants looking to offset housing costs with rental income. Both kitchens feature quartz countertops, with stainless steel appliances and a stackable washer/dryer in the first-floor unit. Wood flooring and generous windows bring warmth and natural light, while the second-floor screened-in porch offers a place to relax. A HUGE walk-up attic is a standout feature, offering abundant storage and exciting finishing potential for a buyer with the right vision. The sewer line was relined in 2021, a major infrastructure improvement! The paved driveway provides plenty of off-street parking, and the level rear yard adds outdoor space to enjoy. An unfinished basement, public water and sewer, natural gas, and a Navien tankless water heater installed in 2020 round out the features. Whether you're looking to house hack, generate rental income, or explore the home's untapped potential, this downtown two-family deserves a look. Make it yours today, this one won't last!
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,700 sq ft
- Lot Size
- 0.11 acres
- Garage / Parking
- 4 total
- Property Taxes
- $5,770 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
8
9 under contract
Median List Price
$459,900
8 active listings
Median Closed Price
$377,500
44 sales
Median Days on Market
72
8 active listings
Median $ / Sq Ft
$141
8 active listings
Sale-to-List Ratio
103.1%
44 sales
How this home compares
List Price
$274,900
vs $459,900 median
40.2% below median
Price / Sq Ft
$162
vs $141 median
14.9% above median
Days on Market
0 days
vs 72 days median
72 days fresher than median
Based on 8 active and 44 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of October 9, 2026.
Location
219 Pearl Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$1,523
- Property Taxes$481
- Insurance$92
- 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
- Duplex
- Style
- Units on different Floors
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 1,700 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardHot WaterRadiator
- Heat Fuel
- Natural GasOil
- Cooling
- Window Unit
- Laundry
- Washer/Dryer All Units
- Laundry Location
- FL1 Stackable / FL2 Washer only
- Basement
- FullUnfinishedInterior AccessConcrete Floor
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- RPZ
- Garage / Parking
- 4 total parking spacesDrivewayPavedOff Street ParkingPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $5,770 / Annually
- Days on Market
- 0
- MLS #
- 24213164
- MLS Status
- Coming Soon
- Financing
- FHA,VA,CHFA
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Christopher Farrell
Carbutti & Co., Realtors
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/9/2026. 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 10/9/2026 at 7:25 PM UTC.