102 DUKE OF GLOUCESTER ST Annapolis, MD 21401 Open Sun 11AM-1PM

UPDATED: 09/18/2026 04:04 AM ON MARKET: New on market today

$1,750,000

4 Beds4 Baths2,718 SqFt

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 2,718 sqft

Price per Sqft $643

Subdivision Colonial Annapolis Historic District

MLS Listing ID MDAA2156954

Style Colonial,Victorian

Bedrooms 4

Full Baths 3

Half Baths 1

HOA Y/N N

Abv Grd Liv Area 1,908

Year Built 1920

Available Date 2026-09-18

Annual Tax Amount $16,323

Tax Year 2025

Lot Size 3,485 Sqft

Acres 0.08

Property Sub-Type Detached

Source BRIGHT

Property Description

If you love a home that breathes history, you'll fall in love with this one. Ideally situated at 102 Duke of Gloucester Street, the property rests along one of the area's most historic streets—named in the late 1600s in honor of Prince William, The Duke of Gloucester.

Set on one of the most desirable stretches of the street, this classic Annapolis home is one where history, character, and everyday livability come together beautifully.

Directly across from St. Mary's Church, this four-bedroom, 3.5-bath residence offers just under 3,000 square feet perched on a generous lot with ample private parking. Its location places you within effortless walking distance of Spa Creek, Main Street, Ego Alley, the Annapolis Yacht Club, and Eastport—an extraordinary position that puts the very best of Annapolis at your doorstep.

From the moment you cross the threshold, the charm is unmistakable. This home is filled with warm natural light and the energy of a true Annapolis residence that has been has been lived in, loved, and appreciated in its time. Rich wood, original details, and an authentic sense of place create an atmosphere that simply cannot be replicated in a new build.

Among its most beautiful details are the original panes of glass showcased at the front of the home, along with rare, old-growth Georgia hard-pine edge-grain floors, and an original letter box—craftsmanship and materials that are increasingly difficult, if not impossible, to find today.

The second floor showcases an especially inviting primary suite with a huge bath filled with warm morning light— a peaceful place to begin each day surrounded by the character of historic Annapolis. An additional full bath and bedrooms right down the hall.

A bright and spacious grand room crowns the 3rd floor to be used as you like for an additional bedroom, exercise, and artist haven, office - you decide!

The lower level is fitted with the original brick floors and offers a private full suite—an exceptional space for guests, extended family, or separate living arrangement. Additionally it includes its own secluded workshop, a rare and charming feature for someone who enjoys working with their hands, tackling projects, or simply having a dedicated place to create.

Easily accessed from the kitchen breakfast area, the rear yard is one of the property's most unexpected treasures. This generous outdoor space, not often found in downtown, offers privacy, a place to garden, entertain or simply letting the dog run and play.

You will have your own highly desired and remarkably convenient parking for downtown living with room for two full-size vehicles or up to three compact cars, complemented by additional ample street parking.

A fire-suppression system adds an additional layer of peace of mind to this historic residence. The sewer line was updated within the last 8 years and the roof was replaced in 2016 with 50 year rated shingles.

But perhaps what makes this home most special is what cannot be measured in square footage.

It has soul.

The wood is rich. The light is warm. The architecture carries the imprint of another era. And the location is nearly impossible to duplicate.

For those who appreciate the romance of an old home—the imperfections, the craftsmanship, the history, and the stories embedded within its walls—102 Duke of Gloucester Street offers something increasingly rare: a genuine piece of Annapolis that still still feels like a home.


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