598 High Street
Middletown, Connecticut 06457
- Beds
- 3
- Baths
- 2
- SqFt
- 1,714
- Acres
- 0.19
- Year Built
- 1900
- Property Type
- Single Family

Matt Caiola
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About This Home
Rarely does a home blend historic character, creative energy & walkable in-town living so effortlessly. Nestled on a beautifully landscaped corner lot just moments from Wesleyan University, vibrant downtown Middletown & the Connecticut River waterfront, this thoughtfully updated early-1900s home offers warmth, flexibility & timeless appeal. Featuring 3 bedrooms, 2 full baths & a versatile third-floor studio, the flexible layout is ideal for an artist's retreat, home office, guest suite or creative sanctuary. Original character shines throughout with exposed brick, custom built-ins & abundant natural light. The updated kitchen features a Viking 6-burner range & opens seamlessly to the living & dining areas, creating an inviting space for everyday living & entertaining. Significant updates include newer windows, roof & a tankless hot water heater, while the classic brownstone foundation reflects the home's enduring craftsmanship. Outside, enjoy the charm of your own private city homestead with mature perennial gardens, window boxes, a fenced corner lot, dedicated garden beds, a welcoming back porch & even a chicken coop. A detached garage with bonus studio space offers endless possibilities for hobbies, a workshop or additional workspace. Just a short stroll to downtown restaurants, shops, local schools, parks & the riverfront, this exceptional property offers the perfect balance of historic charm, modern comfort & an unbeatable in-town lifestyle.
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1900
- Days on Market
- 24 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,714 sq ft
- Lot Size
- 0.19 acres
- Garage / Parking
- 1 garage · 3 total
- Property Taxes
- $4,863 / Annually
Market Snapshot
The Middletown Market
Single Family · trailing 12 months
Active Listings
28
63 under contract
Median List Price
$455,000
28 active listings
Median Closed Price
$400,000
316 sales
Median Days on Market
46
28 active listings
Median $ / Sq Ft
$248
28 active listings
Sale-to-List Ratio
101.9%
316 sales
How this home compares
List Price
$437,900
vs $455,000 median
In line with median
Price / Sq Ft
$255
vs $248 median
In line with median
Days on Market
24 days
vs 46 days median
22 days fresher than median
Based on 28 active and 316 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of July 28, 2026.
Location
598 High Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,233
- Property Taxes$405
- Insurance$146
- 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
- Colonial
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 1,714 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Middletown
Interior
- Heating
- Steam
- Heat Fuel
- Natural Gas
- Cooling
- Window Unit
- Laundry
- Lower Level
- Appliances
- Gas CooktopOven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.19 acres
- Zoning
- RPZ
- Garage / Parking
- 1 garage space3 total parking spacesDetached GarageBarnDrivewayOff Street ParkingPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Corner LotTreed
Listing & Financials
- Property Taxes
- $4,863 / Annually
- Days on Market
- 24
- MLS #
- 24188898
- MLS Status
- Under Contract - Continue to Show
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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 6:50 AM UTC.