Active Under Contract
House for sale at 108 High St, Middletown, CT 06457 | MLS# 24202328 | Listing updated on 2026-09-30
Photo 1 of House for sale at 108 High St, Middletown, CT 06457 | MLS# 24202328 | Listing updated on 2026-09-30
Photo 2 of House for sale at 108 High St, Middletown, CT 06457 | MLS# 24202328 | Listing updated on 2026-09-30
Photo 3 of House for sale at 108 High St, Middletown, CT 06457 | MLS# 24202328 | Listing updated on 2026-09-30
Photo 4 of House for sale at 108 High St, Middletown, CT 06457 | MLS# 24202328 | Listing updated on 2026-09-30
16+
Beds Icon

Street View

$399,900

Monthly Est:$1,990

  • Beds Icon6 Beds
  • Beds Icon
    2 Baths
  • Beds Icon2,584sqft

108 High St, Middletown, CT 06457

$1,990/moEst:

Get Pre-Approved

  • Duplex

  • Built in 1900

  • $-- HOA

  • 4,791.6 sqft lot

  • $155/sq.ft

Description

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!

  • Houzeo last checked: 48 minutes ago
  • Listing updated: September 30, 2026 at 1:12 am
  • Listing Provided by: Michelle Mazzotta | eXp Realty
  • Source: SMART MLS-CT | MLS#: 24202328 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Middletown

  • Neighborhood

    --

  • Year Built

    1900

  • HOA Fees

    -

  • Finished Area

    2,584 sqft

  • Lot Size

    4,791.6 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24202328

  • MLS Status

    Under Contract - Continue to Show

  • Days on Market

    40

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 2

Interior

  • Heating

    Hot Water, Oil

  • Cooling

    None

  • Sewer

    Public Sewer Connected

Construction

  • Year Built

    Year Built: 1900

  • Home type

    Duplex

  • Architectural Style

    Units On Different Floors

  • Foundation Details

    Brick

  • Roof

    Asphalt Shingle

Utilities & Energy

  • Basement

    Full, Unfinished, Concrete Floor, Full With Walk Out

  • Water Source

    Public Water Connected

  • Laundry Features

    Washer/dryer Some Units

  • Parking Features

    Off Street Parking, Driveway

Other Features

  • Subdivision Name

    N/a

  • Lot Features

    Corner Lot, Level Lot

Price History

DateEventPrice

09/05/2026

Source: mls_logoSMART MLS-CT #24202328

Contingent (Active Under Contract)

$399,900

$155/sqft

08/28/2026

Source: mls_logoSMART MLS-CT #24202328

Listed for Sale

$399,900 +22751.43%

$155/sqft

05/01/2024

Source: #24001431

Price Decreased

$1,750 -99.42%

$1/sqft

02/22/2024

Source: #170613183

Price Increased

$300,000 +110.08%

$116/sqft

03/06/2017

Source: #G10201997

Sold

$142,800

$55/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 08, 2026, 07:30AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group