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 multi-family, MLS #1528153 and Commercial MLS #1528157
As the MLS and public records start to fill up, we'll list the details here.
Public record
Public record
Zoning
Permits
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
—
Year renovated
—
Sq. Ft.
—
Year built
—
Style
Multi-Family (2-4 Unit)
County
Cumberland County
APN
—
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on May 13, 2022.
R6
Residential
To set aside areas on the peninsula for housing characterized primarily by multi-family dwellings at a high density providing a wide range of housing for differing types of households; to conserve the existing housing stock and residential character of neighborhoods by controlling the scale and external impacts of professional offices and other nonresidential uses; and to encourage new housing development consistent with the compact lot development pattern typically found on the peninsula.
Permitted uses
Include but are not limited to:
Housing-Single unit
Housing-Multiple units
Housing-Other
Bed & breakfast
Lodging & hospitality-Other
Cemetery
Park & open space
Sep 30, 2025 • Final
Electrical
Electrical
Sep 29, 2025 • Final
Hvac
HVAC
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking Information
Has Garage
Attached Garage: Yes
# of Garage Spaces: 2
Parking Features: 1 - 4 Spaces, Paved, On Site, Off Street
Tankless Water Heater, Washer, Refrigerator, Microwave, Electric Range, Dryer, Dishwasher
Flooring: Wood, Tile, Carpet
Other Equipment: Internet Access Available, Cable
Laundry Information
Laundry Features: Washer Hookup
Fireplace Information
# of Fireplaces: 2
Has Fireplace
Exterior
Building Information
Construction Materials: Brick, Masonry
Foundation Details: Stone, Brick/Mortar
Roof: Flat, Membrane, Pitched, Shingle, Slate
Structure Type: Townhouse
Total Building Area (Sq. Ft.): 5,099
Building Area Source: Seller
Property Information
Property Sub Type: Single Family Residence
Year Built: 1868
Above-Grade Finished Area (Sq. Ft.): 4,421
Below-Grade Finished Area (Sq. Ft.): 678
Lot Information
Lot Size (Sq. Ft.): $3,920.40
Lot Size (Acres): 0.09
Lot Size Source: Public Records
Lot Features: Level, Sidewalks, Historic District, Intown, Near Golf Course, Near Public Beach, Near Shopping, Near Turnpike/Interstate, Neighborhood, Near Railroad
Road Surface Type: Paved
Zoning: R6
Financial
Tax Information
Annual Tax Amount: $10,465
Tax Year: 2021
Utilities
Utility Information
Has Heating
Heating: Steam, Radiator
Electric: Circuit Breakers
Sewer: Public Sewer
Water Source: Public
Water Heater: Off Heating System
Location
HOA Information
Pets Allowed: No Restrictions
Location Information
Unparsed Address: 14 Deering Street, Portland, ME 04101
Directions: From State St, left onto Deering St. 14 is on right side of the street, right side of the building. From High St, left onto Deering St, 14 is on left side of the street, right side of building
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Multi-Family (2-4 Unit)
Year Built: —
Year Renovated: —
County: Cumberland County
APN: —
Home facts updated by county records on May 13, 2022
Around this home
Schools
Howard C Reiche Community School
Public PreK-5 • Assigned • 0.3mi
3/10
Deering High School
Public 9-12 • Assigned • 2.0mi
2/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Historical weather
Portland, ME • 04101
Average low and high temperatures (°F)
31
18
33
18
44
30
52
39
63
49
74
58
79
64
77
60
71
56
61
46
50
36
36
22
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.5 hours in
June and 4.3 hours in December, placing it below the
U.S. average for solar exposure.
8.5 hrs
4.3 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.20M – $1.46M
Reach more buyers when you sell with Redfin. Save up to $12,665 in fees.3 minutes to get started.
Get a free, detailed breakdown of how we calculated your estimate.