27 Pleasant Street, Middletown, Connecticut

$679,900

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3,314

Square feet

0.17

Acres

About 27 Pleasant Street

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.

Features of 27 Pleasant Street

MLS® # 24175820
Price $679,900
Square Footage 3,314
Square Footage Public Records
Acres 0.17
Type Commercial For Sale
Status Active

Community Information

Address 27 Pleasant Street
Area N/A
City Middletown
County Middlesex
State Connecticut
Zip Code 06457

Amenities

Utilities Electric, Gas, Telephone, Cable
Is Waterfront No
Has Pool No

Interior

Heating Hot Air, Natural Gas
Cooling Central Air
Fireplace No

Exterior

Lot Description Level Lot
Roof Slate

Additional Information

Date Listed May 15th, 2026
Days on Market 115
Zoning MXC
RE / Bank Owned No

Listing Details

OfficeiHeart Homes Real Estate LLC

Listing Map

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