Skip to main content

598 High Street

Middletown, Connecticut 06457

PENDING$437,900
Beds
3
Baths
2
SqFt
1,714
Acres
0.19
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
1-Car Garage

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,784

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Michelle Mazzotta

(860) 305-5908

eXp Realty

(866) 828-3951

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.