New Listing - 05/15/2026

Listing courtesy of Michael Criscio (203) 314-9620, iHeart Homes Real Estate LLC (203) 433-2007


27 Pleasant Street, Middletown, CT, 06457

27 Pleasant Street, Middletown, CT, 06457

1850

3,314 sqft

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.


Status:

Active

Type:

Commercial

Units:

1

Zoning:

MXC

Frontage:

Municipal Street

Heating:

Hot Air

Cooling:

Central Air

Acreage:

0.17

Est. Taxes:

$11,728

Assessment

$301,480

Current Use

attorney's office

Permitted Use

attorney, accountant, real estate, dental office, all professional uses

Utilities

Electric,Gas,Telephone,Cable

Lot Description:

Level Lot

Days on Market:

4

MLS #:

24175820


Community Info

School Info

Walk Score

Mass Transit

Yelp


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