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Executive Summary

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 Facts

Sale Type
Investment or Owner User
Property Type
Office
Building Size
3,314 SF
Year Built
1850
Price
$965,907 CAD
Price Per SF
$291.46 CAD
Percent Leased
100%
Building Height
3 Stories
Typical Floor Size
1,105 SF
Moderately walkable
60/100
Exceptionally drivable
100/100
Limited public transit
30/100
Fairly bikeable
40/100

Property Taxes

Property Taxes

Parcel Number
MTWN-000024-000000-000296
Land Assessment
$183,563 CAD
Improvements Assessment
$244,737 CAD
Total Assessment
$428,301 CAD
  • Listing ID: 41094783

  • Date on Market: 2026-06-29

  • Last Updated:

  • Address: 27 Pleasant St, Middletown, CT 06457

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