106 South Front Street
Middletown, Connecticut 06457
- Beds
- 3
- Baths
- 2
- SqFt
- 1,109
- Acres
- 0.17
- Year Built
- 1950
- Property Type
- Single 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
WELCOME HOME to 106 S. Front Street, Middletown! Conveniently located near town with easy access to Route 9, this inviting 3-bedroom, 2-bath home offers comfortable living, charming details, and move-in-ready appeal. Inside, beautiful hardwood floors and fresh paint create a bright, welcoming atmosphere. The cozy living room fireplace adds warmth and character, while the relaxing sun porch provides the perfect spot for morning coffee, quiet reading, or unwinding at the end of the day. Outside, the lovely backyard offers plenty of room to gather, entertain, and enjoy the crisp autumn air-with space to create your own fire pit area... With its comfortable layout, inviting outdoor space, and convenient location, this home is ready for its next chapter-and it may not be available for long. Convenient Location, close to shopping, downtown with wonderful restaurants and Route 9 and the hospital easy commute. Don't miss the opportunity to make 106 S. Front Street yours! Schedule your private viewing and start imagining life in your new home today!
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1950
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,109 sq ft
- Lot Size
- 0.17 acres
- Garage / Parking
- 4 total
- Property Taxes
- $5,487 / Annually
Market Snapshot
The Middletown Market
Single Family · trailing 12 months
Active Listings
49
47 under contract
Median List Price
$425,000
49 active listings
Median Closed Price
$407,000
320 sales
Median Days on Market
33
49 active listings
Median $ / Sq Ft
$254
49 active listings
Sale-to-List Ratio
102.4%
320 sales
How this home compares
List Price
$349,999
vs $425,000 median
17.6% below median
Price / Sq Ft
$316
vs $254 median
24.4% above median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 49 active and 320 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of October 21, 2026.
Location
106 South Front 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$457
- 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
- Single Family
- Style
- Cape Cod
- Year Built
- 1950
- New Construction
- No/Resale
- Living Area
- 1,109 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Electric RangeRefrigeratorWasher
- Basement
- FullPartially FinishedFull With Hatchway
- Interior Features
- Cable - Pre-wired
Exterior & Lot
- Lot Size
- 0.17 acres
- Zoning
- RPZ
- Garage / Parking
- 4 total parking spacesDrivewayPavedOff Street ParkingPrivatePavedAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-ScreenedPorch-EnclosedBreezewayPorchGutters
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $5,487 / Annually
- Days on Market
- 0
- MLS #
- 24215963
- MLS Status
- Coming Soon
- Financing
- FHA,VA,CHFA
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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 10/21/2026. 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 10/21/2026 at 1:00 PM UTC.