37-39 Hotchkiss Street
Middletown, Connecticut 06457
- Beds
- 4
- Baths
- 2
- SqFt
- 1,616
- Acres
- 0.11
- Year Built
- 1900
- Property Type
- 2 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Updated two-family in a fantastic Middletown location just minutes from Wesleyan University, downtown shopping, and Route 9 - great for an owner-occupant or investor, with one unit delivered open at the end of the month and ready for immediate occupancy. Recent improvements have all the major boxes checked: brand new roof, brand new water heaters, plus updated kitchens, updated baths, and newer flooring throughout - all completed within the last five years. Everything is properly split for hassle-free two-family living: separate natural gas heat with two boilers, two electric panels, and two gas meters - no shared utilities, clean books, easy management. The first-floor unit features in-unit laundry, while both units offer a comfortable layout with multiple bedrooms, a full bath, eat-in kitchen, and a covered front porch overlooking the neighborhood. Outside you'll find a private off-street driveway with parking for multiple vehicles, a level yard, mature shade trees, and a metal storage shed for added convenience. Whether you're looking to offset your mortgage with rental income, expand your investment portfolio, or set up a multi-generational living arrangement, 37-39 Hotchkiss delivers strong fundamentals, modern updates, and a prime walkable location near one of Connecticut's premier university towns. Don't miss this one! Agent Owner
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 84 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,616 sq ft
- Lot Size
- 0.11 acres
- Garage / Parking
- 4 total
- Property Taxes
- $5,525 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
10
9 under contract
Median List Price
$419,500
10 active listings
Median Closed Price
$388,000
45 sales
Median Days on Market
38
10 active listings
Median $ / Sq Ft
$152
10 active listings
Sale-to-List Ratio
103.5%
45 sales
How this home compares
List Price
$339,900
vs $419,500 median
19.0% below median
Price / Sq Ft
$210
vs $152 median
38.2% above median
Days on Market
84 days
vs 38 days median
46 days longer than median
Based on 10 active and 45 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of July 28, 2026.
Location
37-39 Hotchkiss Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,733
- Property Taxes$460
- Insurance$113
- 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
- 1,616 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Middletown
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- DVD
- Garage / Parking
- 4 total parking spacesOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $5,525 / Annually
- Days on Market
- 84
- MLS #
- 24172703
- MLS Status
- Under Contract - Continue to Show
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 7/28/2026. 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 7/28/2026 at 6:15 AM UTC.