# 423 Main Street, Middletown, CT 06457 > **TL;DR:** 0bd/4ba commercial, $4,500,000 ($115/sqft), built 1944, 39,000 sqft. > A/C. Est. $24,067/mo. Listed 110 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $4,500,000 | | Price/sqft | $115 | | Bathrooms | 4 full | | Square Feet | 39,000 | | Year Built | 1944 | | Lot Size | 7,841 sqft (0.18 acres) | | Property Type | Commercial (Other) | | Status | Active | | Days on Market | 110 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $22,754 | | Estimated Insurance | $1,313 | | **Total** | **$24,067** | ## Key Amenities - A/C ## Property Highlights - Built in 1944 - 0.18 acre lot ## Description ### Agent Description Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts. ## Location - **Address:** 423 Main Street, Middletown, CT 06457 - **County:** Middlesex - **Coordinates:** 41.561885, -72.651204 - **Google Maps:** https://www.google.com/maps?q=41.561885,-72.651204 ## Listing Agent - **Name:** Maggie Damato - **Brokerage:** Executive Real Estate - **Phone:** 8605103991 - **Broker Phone:** (860) 633-8800 - **Listing URL:** [View original listing](https://listings.listhub.net/pages/CTMLS/24182009/?channel=propsimple) ## Photos ![423 Main Street - Photo 1](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2562589871r.jpg) ![423 Main Street - Photo 2](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2368791470r.jpg) ![423 Main Street - Photo 3](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1677844572r.jpg) ![423 Main Street - Photo 4](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1264850108r.jpg) ![423 Main Street - Photo 5](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f246170405r.jpg) ![423 Main Street - Photo 6](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1228757239r.jpg) ![423 Main Street - Photo 7](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f895094409r.jpg) ![423 Main Street - Photo 8](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f4077576343r.jpg) ![423 Main Street - Photo 9](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f732755011r.jpg) ![423 Main Street - Photo 10](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3438592824r.jpg) ![423 Main Street - Photo 11](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3326421605r.jpg) ![423 Main Street - Photo 12](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1008046984r.jpg) ![423 Main Street - Photo 13](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f485699758r.jpg) ![423 Main Street - Photo 14](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2913558276r.jpg) ![423 Main Street - Photo 15](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3087950253r.jpg) ![423 Main Street - Photo 16](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f918366308r.jpg) ![423 Main Street - Photo 17](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3352289604r.jpg) ![423 Main Street - Photo 18](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1133459035r.jpg) ![423 Main Street - Photo 19](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2223314220r.jpg) ![423 Main Street - Photo 20](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2018217266r.jpg) ![423 Main Street - Photo 21](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1639218247r.jpg) ![423 Main Street - Photo 22](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1586741059r.jpg) ![423 Main Street - Photo 23](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2701944846r.jpg) ![423 Main Street - Photo 24](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1890753869r.jpg) ![423 Main Street - Photo 25](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3813498079r.jpg) ![423 Main Street - Photo 26](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1563268301r.jpg) ![423 Main Street - Photo 27](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f410470565r.jpg) ![423 Main Street - Photo 28](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1448223338r.jpg) ![423 Main Street - Photo 29](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1477001619r.jpg) ![423 Main Street - Photo 30](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3813498079r.jpg) ![423 Main Street - Photo 31](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3813498079r.jpg) ![423 Main Street - Photo 32](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1563268301r.jpg) ![423 Main Street - Photo 33](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f410470565r.jpg) ![423 Main Street - Photo 34](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1448223338r.jpg) ![423 Main Street - Photo 35](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3280134232r.jpg) ![423 Main Street - Photo 36](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1801121714r.jpg) ![423 Main Street - Photo 37](http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f4157714536r.jpg) --- **MLS#:** 24182009 | **Updated:** 2026-09-27 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009#listing", "url": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009", "name": "423 Main Street, Middletown, CT 06457", "description": "Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.", "image": [ "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2562589871r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2368791470r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1677844572r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1264850108r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f246170405r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1228757239r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f895094409r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f4077576343r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f732755011r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3438592824r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3326421605r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1008046984r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f485699758r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2913558276r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3087950253r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f918366308r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3352289604r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1133459035r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2223314220r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2018217266r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1639218247r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1586741059r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2701944846r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1890753869r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3813498079r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1563268301r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f410470565r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1448223338r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1477001619r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3280134232r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1801121714r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f4157714536r.jpg" ], "primaryImageOfPage": { "@type": "ImageObject", "url": "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2562589871r.jpg", "caption": "423 Main Street - Middletown, CT" }, "datePosted": "2026-06-10T00:00:00+00:00", "dateModified": "2026-09-27T11:30:46.78329+00:00", "mainEntity": { "@type": "Place", "@id": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009#property", "name": "423 Main Street, Middletown, CT 06457", "address": { "@type": "PostalAddress", "streetAddress": "423 Main Street", "addressLocality": "Middletown", "addressRegion": "CT", "postalCode": "06457", "addressCountry": "US" }, "geo": { "@type": "GeoCoordinates", "latitude": 41.561885, "longitude": -72.651204 }, "image": [ "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2562589871r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2368791470r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1677844572r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1264850108r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f246170405r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1228757239r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f895094409r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f4077576343r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f732755011r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3438592824r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3326421605r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1008046984r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f485699758r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2913558276r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3087950253r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f918366308r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3352289604r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1133459035r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2223314220r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2018217266r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1639218247r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1586741059r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f2701944846r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1890753869r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3813498079r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1563268301r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f410470565r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1448223338r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1477001619r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f3280134232r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f1801121714r.jpg", "http://lh.rdcpix.com/b65ec595b577b6d5768a31d8f9010a7cl-f4157714536r.jpg" ], "identifier": { "@type": "PropertyValue", "propertyID": "MLS", "value": "24182009" }, "amenityFeature": [ { "@type": "LocationFeatureSpecification", "name": "Cooling", "value": "Central Air" }, { "@type": "LocationFeatureSpecification", "name": "Air Conditioning", "value": true } ], "additionalProperty": [ { "@type": "PropertyValue", "name": "Lot Size", "value": "0.18 acres" }, { "@type": "PropertyValue", "name": "Property Subtype", "value": "Other" }, { "@type": "PropertyValue", "name": "Property Type", "value": "Commercial" } ] }, "offers": { "@type": "Offer", "@id": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009#offer", "url": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009", "price": 4500000, "priceCurrency": "USD", "businessFunction": "http://purl.org/goodrelations/v1#Sell", "availability": "https://schema.org/InStock", "seller": { "@id": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009#agent" } }, "provider": { "@type": "Person", "@id": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009#agent", "name": "Maggie Damato", "telephone": "8605103991", "worksFor": { "@type": "Organization", "@id": "https://www.propertysimple.ai/listing/423-main-street-middletown-ct-06457-24182009#brokerage", "name": "Executive Real Estate", "telephone": "(860) 633-8800" } } } ```