$1,200,000
$1,375,000
336 days on market
$175K
$1,155,000
$45K
Estimated value as of Nov 2026
165 King George Street, ANNAPOLIS
ANNE ARUNDEL, HISTORIC DISTRICT, MD, 214014
3
2,649 sqft
MLS® # MDAA2132242
Listing courtesy of Michele M Michael, CENTURY 21 New Millennium (Annapolis, MD)
Description
Rare Historic Triplex in Downtown Annapolis – Live for Free with Built-In Income! Unlocking a premier real estate strategy in the heart of Historic Annapolis, this versatile multi-unit property offers an incredible opportunity to live in one unit while letting the other two pay your mortgage. Perfectly positioned just steps from City Dock, Main Street, and the United States Naval Academy, this rare 3-unit asset seamlessly blends timeless 18th-century architectural character with strong, recurring cash flow. The property features independent, distinct rental units with updated kitchens, modern utilities, and separate entrances, ensuring maximum privacy for both the owner and tenants. For an owner-occupant, renting out the remaining two units provides a robust revenue stream capable of covering major carrying costs, allowing you to build equity rapidly while enjoying a premier walkable lifestyle. Investors will appreciate the historically low vacancy rates of the downtown market, driven by stable demand from maritime professionals, state government staff, and USNA tourism. Complete with original hardwood floors, historic brick accents, and premium rental appeal, this triplex is a high-utility asset built for wealth generation. Schedule your private tour today to secure a premier piece of Annapolis history that pays for itself.
There are very few multifamily dwelling units in the City of Annapolis. This creates a rare and amazing opportunity for buyers to own one of the few existing multifamily dwelling units that’s a triplex. There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Multi-Family MLS# MDAA2132270. Parking info is loaded in the documents section. Unit schedule: Unit 1 is lived in and can be seen normally with one days notice. Unit 2 and Unit 3 have various bookings and more notice is required.
165 King George Street, ANNAPOLIS
ExploreHome
Category
Residential
Style
Residential
Type
Townhouse
Taxes/Year
$11,054 / 2024
Status
New
Days on Market
336 Days Ago
List Date
Dec 2, 2025
Updated On
Aug 31, 2026
Year Built
1900
Features
Beds & Baths
Bedrooms
4
Bathrooms
3
Heating & Cooling
Heating Type
Electric, Zoned, Heat Pump
Heating Fuel
Electric
Air Conditioning
Central Air, Ceiling Fan(s), Multi Units, Zoned, Electric
Fireplaces
No
Basement
Type
Unfinished, Interior Entry
Exterior
Construction
Year Built
1900
Construction Details
Foundation Type
Concrete Perimeter
Roof Material
Metal, Shingle
Exterior
Cedar, Shingle Siding
Water & Sewer
Water Supply
Public
Sewer
Public Sewer
Legal
Brokerage
CENTURY 21 New Millennium
Sale History
Active
(336 days on market)
Viewing now
Dec 2, 2025
Listed For Sale
$1,200,000
MLS® # MDAA2132242