108 High Street Middletown, CT $ 399,900
108 High Street
$ 399,900
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108 High Street

Middletown, CT, 06457
$ 399,900
Bedrooms6 Baths2.0 Sq 2,584

Monthly Estimate*

$ 2,525

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Multi-Family Home for sale in Middletown, CT

for $399,900 with 6 bedrooms and 2 full baths. This 2,584 square foot home was built in 1900 on a lot size of 0.11.

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!

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Multi-Family Active

Price

$ 399,900

Bedrooms

6

Full Bath

2

Property Type

Multi-Family

Taxes

$ 5,426

Style

Lot Size

0.11

Year Built

1900

Town/City

Middletown

MLS | Web ID

24202328

Features
General
Zoning DVD
Neighborhood N/A
County Middlesex
Tax Year July 2026-June 2027
Property Type Multi-Family For Sale
Status Active
Acres 0.11
Directions GPS Friendly.
High School Middletown
City Middletown
Elementary School Per Board of Ed
Sq Ft Total 2584
DOM 0
Year Built 1900
Style Units on different Floors
Year Built Source Public Records
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Interior
Cooling System None
Total Number of Units 2
Total Rooms 12
Basement Description Full Unfinished Concrete Floor Full With Walk-Out
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Exterior
Water Source Public Water Connected
Lot Description Corner Lot Level Lot
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* Excluded Features
List By
Michelle Mazzotta

Listing Agent

Exp Realty

Broker

michellemazzotta1@gmail.com

Email

Affordability Calculator

$2,977
Per Month
85%
15%
0%
Monthly Principal & Interest
$2,525
Monthly Property Taxes
$452
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
2059950 Elementary School
4619834 Middle School
Middletown High School High School
Pricing History
DatePricePrice ChangeDescription
8/28/2026$399,900 Listed Price

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108 High Street, Middletown, CT, 06457 is a Multi-Family Home for sale at $399,900 with 2,584 sqft and a lot size of 0.11. 108 High Street has 6 bedrooms, 2.0 baths, and was built in 1900. The property's zip code is 06457 which is in Middletown, CT