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!
For sale
$399,900
108 High Street, Middletown, CT 06457
6beds
2,584sqft
Multi Family
Built in 1900
-- sqft lot
$-- Zestimate®
$155/sqft
$-- HOA
What's special
Charming period details throughoutConvenient walkout basementCorner lotBeautiful built-in cabinetryThree bedroomsWood flooringSpacious unit
- 7 days
- 691
- 56
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Michelle Mazzotta (860)305-5908,
eXp Realty 866-828-3951
Source: Smart MLS,MLS#: 24202328
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Hot Water, Oil
Cooling
- None
Appliances
- Included: Electric Water Heater, Water Heater
- Laundry: In Unit
Features
- Basement: Full,Unfinished,Concrete
- Attic: Crawl Space,Storage,Access Via Hatch
- Number of fireplaces: 1
Interior area
- Total structure area: 2,584
- Total interior livable area: 2,584 sqft
- Finished area above ground: 2,584
Property
Parking
- Total spaces: 4
- Parking features: Off Street, Driveway, Paved
- Has uncovered spaces: Yes
Lot
- Size: 4,791 Square Feet
- Features: Corner Lot, Level
Details
- Parcel number: 1013153
- Zoning: DVD
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Units on different Floors
- Property subtype: Multi Family
Materials
- Aluminum Siding
- Foundation: Brick/Mortar
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Middletown
Financial & listing details
- Price per square foot: $155/sqft
- Tax assessed value: $132,990
- Annual tax amount: $5,426
- Date on market: 8/28/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 8/28/2026 | Listed for sale | $399,900+33.3%$155/sqft |
Source: | ||
| 4/19/2024 | Listing removed | -- |
Source: Smart MLS #24001431 Report a problem | ||
| 3/28/2024 | Listed for rent | $1,750$1/sqft |
Source: Smart MLS #24001431 Report a problem | ||
| 2/22/2024 | Sold | $300,000-4.8%$116/sqft |
Source: | ||
| 1/25/2024 | Listed for sale | $315,000$122/sqft |
Source: | ||
| 1/3/2024 | Contingent | $315,000$122/sqft |
Source: | ||
| 12/6/2023 | Listed for sale | $315,000+120.6%$122/sqft |
Source: | ||
| 6/19/2017 | Sold | $142,800-10.7%$55/sqft |
Source: | ||
| 4/24/2017 | Pending sale | $159,900$62/sqft |
Source: Hagel & Assoc. Real Estate #G10201997 Report a problem | ||
| 3/6/2017 | Listed for sale | $159,900$62/sqft |
Source: Hagel & Assoc. Real Estate #G10201997 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,173 +5.7% | $132,990 |
| 2024 | $4,894 +4.8% | $132,990 |
| 2023 | $4,668 +14.6% | $132,990 +43.7% |
| 2022 | $4,073 | $92,570 |
| 2021 | $4,073 -0.5% | $92,570 |
| 2020 | $4,092 -0.4% | $92,570 |
| 2019 | $4,110 +1.6% | $92,570 |
| 2018 | $4,045 -16.1% | $92,570 -18.6% |
| 2017 | $4,822 +7.1% | $113,720 |
| 2015 | $4,503 -1% | $113,720 |
| 2014 | $4,549 -13.7% | $113,720 -27% |
| 2013 | $5,269 +3.4% | $155,880 |
| 2012 | $5,097 +3.5% | $155,880 |
| 2011 | $4,926 -0.9% | $155,880 |
| 2010 | $4,973 +4.6% | $155,880 |
| 2009 | $4,754 +19.6% | $155,880 |
| 2008 | $3,975 -5.6% | $155,880 +41.4% |
| 2007 | $4,212 +1.3% | $110,270 |
| 2006 | $4,157 +5.6% | $110,270 |
| 2005 | $3,937 +8.8% | $110,270 |
| 2003 | $3,617 | $110,270 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 06457
Nearby schools
Schools provided by the listing agent
- High: Middletown
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.







