NOMADEReal Estate

$679,900

Active

27 Pleasant Street

Middletown, Connecticut, 06457 · Middlesex County

3,314

Sq Ft

1850

Built

MLS # 24175820

Price / Sq Ft

$205

Property Type

Commercial For Sale

Lot Size

0.17

Class

Property

About This Property

Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

Property Details

27 Pleasant Street, Middletown Connecticut 06457 — Commercial For Sale listed at $679,900.

At a Glance

--

Bedrooms

--

Bathrooms

3,314

Sq Ft

0.17

Lot Size

--

Garage

1850

Year Built

The Details

Property TypeCommercial For Sale
NeighborhoodMiddlesex
Address27 Pleasant Street
MLS Number24175820
Year Built1850
Square Footage3,314
Lot Size0.17
Water SourcePublic Water Connected

Property Details

Financial

Assessed Value301480
Mil Rate Total38.9
Property Tax11728
Tax YearJuly 2025-June 2026

Property Features

Cooling SystemCentral Air
Heat Fuel TypeNatural Gas
Heat TypeHot Air
Roof InformationSlate

Location & Community

Directions27 Pleasant St
LocationDowntown
NeighborhoodN/A

All Photos (40)

Affordability Calculator

$679,900

Down Payment$135,980
Loan Amount$543,920
Principal & Interest$3,438/mo
Property Tax$680/mo
Insurance$100/mo
Est. Monthly$4,218/mo

Listing Agent

M

Michael Criscio

iHeart Homes Real Estate LLC

Contact Michael Criscio

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Quick Facts

StatusActive
TypeCommercial For Sale
ClassProperty
MLS #24175820
Last Updated2026-05-15