108 High Street
Middletown, Connecticut 06457
- Beds
- 6
- Baths
- 2
- SqFt
- 2,584
- Acres
- 0.11
- Year Built
- 1900
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to this character-filled, turn-of-the-century two-family Colonial in the heart of Middletown, ideally located directly across from Wesleyan University and within walking distance of downtown, restaurants, shops, and public transportation. Each spacious unit offers three bedrooms, a generous living room with a fireplace, beautiful built-in cabinetry, wood flooring, and French doors opening to a sunroom. Large, open kitchens with walk-in pantries provide ample space and functionality, while charming period details throughout reflect the home's original character. The first-floor unit is vacant and move-in ready, while the second-floor unit is currently tenant-occupied, offering immediate rental income. A new roof adds significant value, while the interiors still provide opportunities for updates and personal touches. Situated on a corner lot with two separate driveways accessed from different streets, plus a convenient walkout basement. An excellent opportunity for an owner-occupant or investor!
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
- 6
- Baths
- 2 full
- Living Area
- 2,584 sq ft
- Lot Size
- 0.11 acres
- Garage / Parking
- 4 total
- Property Taxes
- $5,426 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
12
6 under contract
Median List Price
$404,950
12 active listings
Median Closed Price
$377,500
46 sales
Median Days on Market
59
12 active listings
Median $ / Sq Ft
$153
12 active listings
Sale-to-List Ratio
102.8%
46 sales
How this home compares
List Price
$399,900
vs $404,950 median
In line with median
Price / Sq Ft
$155
vs $153 median
In line with median
Days on Market
0 days
vs 59 days median
59 days fresher than median
Based on 12 active and 46 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of August 28, 2026.
Location
108 High Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$2,056
- Property Taxes$452
- Insurance$133
- 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
- 2,584 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Middletown
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Washer/Dryer Some Units
- Basement
- FullUnfinishedConcrete FloorFull With Walk-Out
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- DVD
- Garage / Parking
- 4 total parking spacesOff Street ParkingDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Brick
- Lot Description
- Corner LotLevel Lot
Listing & Financials
- Property Taxes
- $5,426 / Annually
- Days on Market
- 0
- MLS #
- 24202328
- MLS Status
- Active
Similar Properties
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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 8/28/2026. 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 8/28/2026 at 3:20 PM UTC.