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$4,200,000 -$495,000 (-10.54%) Price Reduced
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Property Description
Prime Investment Opportunity in Chester, CT Presenting 189-191 Middlesex Avenue, a fully leased, mixed-use property offering an exceptional investment opportunity in the heart of Chester, Connecticut. This 21,905 SF complex features a mix of retail, office, and residential spaces, with long-term tenants, ensuring stability and consistent revenue. Property Highlights * Fully Leased with established tenants * Strong financials-Projected 2025 NOI of $378,000 * Significant annual increases and pass-through for operating expenses * Ample on-site parking for tenants and visitors * High visibility on a well-trafficked state road * Well-maintained by current ownership for 19 years Location Benefits * 3.02-acre lot in a desirable commercial zone (C) * Built in 1986, offering modern infrastructure * Convenient access to Route 9 and Exit 3 on Route 154 * Proximity to Chester Village-a vibrant hub of dining, shopping, and scenic attractions About Chester, CT Nestled along the Connecticut River, Chester boasts a unique blend of New England charm and commercial opportunity. Its historic appeal, picturesque views, and strong community make it an attractive destination for businesses and residents alike. This turnkey investment offers immediate and long-term financial rewards in a thriving market. Don't miss out on securing a property with both stability and future growth potential.
Full Property Details
Full Property Details for 189 Middlesex Ave
General
- Price: $4,200,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Commercial
- Source: SMARTMLS
- MLS ID: 24120456
- Updated: 2/24/2026
- Added to Site: 190 day(s) ago
Location
- County: Middlesex
- Driving Directions: Close to the intersection of Middlesex Avenue and Kings Highway
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Electric
- Heating Fuel: Electric
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
- Utility Description: Electric, Gas, Telephone, Cable
Structural Information
- Roof: Asphalt Shingle
- Square Feet: 21,905
- Sq. Ft. Source: Public Records
- Current Bldg. Use: Office/Retail
- Year Built: 1986
Unit Information
- # Tenants: 10
Lot Features
- Lot Size (Acres): 3.02
- Frontage: State Road
- Present Use: Office/Retail
- Potential Use: Office/Retail
- Zoning: C
- Lot Description: Level Lot
Financial Considerations
- Assessment Amount: $1,497,230
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Documents Avail.: Brochure
- Property ID: 941509
Listed by Press/Cuozzo Realtors, Stephen Press
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Schools
Schools serving 189 Middlesex Ave
School Districts:Chester School District, Regional High School District 04
| Name | Grades | Distance |
|---|---|---|
Valley Regional High School 256 Kelsey Hill Road, Deep River, CT 06417 | 9-12 | 3.5 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 189 Middlesex Ave
Date
Details
Price
Change
Source
2/24/2026
Price Reduced
$4,200,000
-10.54%
MLS
10/27/2025
Price Reduced
$4,695,000
-4.09%
MLS
8/19/2025
Listed
$4,895,000
235.27%
MLS
10/11/2006
Sold
$1,460,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 189 Middlesex Ave
Year
Property Taxes
Change
Tax Assessment
Change
2024
$40,545
-24%
$1,497,230
-31%
2023
$53,033
177%
$2,169,020
236%
2023
$19,160
1%
$645,130
—
2022
$19,031
6%
$645,130
6%
2021
$17,925
3%
$607,630
—
2020
$17,390
-1%
$607,630
—
2019
$17,494
-10%
$607,630
-15%
2018
$19,428
3%
$716,650
—
2017
$18,891
3%
$716,650
—
2016
$18,325
1%
$716,650
—
2015
$18,146
2%
$716,650
—
2014
$17,787
4%
$716,650
-8%
2011
$17,066
—
$777,490
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 189 Middlesex Ave
189 Middlesex Avenue, Chester, CT 06412 (MLS# 24120456) is a Commercial property. 189 Middlesex Avenue is currently listed for $4,200,000 and was received on August 19, 2025. Want to learn more about 189 Middlesex Avenue? Do you have questions about finding other Commercial real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

