Built in 1868 by renowned architect Francis H. Fassett for Captain Jacob Winslow who was a leading merchant of 19th century Portland. This Second Empire style gem in the Deering Street Historic District has been well preserved with stunning period fixtures and detailing. You will be impressed when you enter the foyer by the commanding staircase. The first floor offers the original double parlor with original decorative painting and built-in bookcase, dining room with large walk in china closet and kitchen. For many years the 1st floor was used as a commercial space including a dentist office and therapist office. The second level is offers a 2-bedroom apartment with great natural light and a flexible layout. The third floor offers a bright and sunny newly renovated 1 bedroom apartment, including new kitchen appliances and new and restored cabinets as well as terrific storage. Lower level offers original billiard room and game room with magnificent fireplace and woodwork. This property offers generous parking, plus a rare attached two car garage. There are many possibilities for use of this property such as returning to a single family, combination work/live or the current use, or in-law. 1st Floor kitchen is in need of renovation. 14 Deering is an excellent location, steps to the Arts District, West End, Downtown, Old Port , dozens of award winning restaurants and the best of Portland offers. This one is truly special! Also listed as a Residential MLS# 1528149 and Commercial MLS #1528157