LOCATION, LOCATION! OPEN HOUSE MOVED TO SUNDAY APRIL 12TH FROM 12-2 PM. Welcome to one of downtown Annapolis’ most exceptional offerings. Perfectly positioned in the heart of the Historic District, 98 Duke of Gloucester Street is the kind of property Buyers wait years to find. Set on one of the widest, two-way streets downtown, this rare residence offers the convenience of being just steps from the waterfront, restaurants, shops, and the charm that makes Annapolis so special—while maintaining a sense of privacy rarely found in the city. Parking is truly unmatched, with four dedicated spaces including two garages (with EV charger), a private driveway, and a parking pad—an extraordinary amenity in the Historic District. This American Four Square home features 4/5 spacious bedrooms and three full baths, with beautifully designed living and dining spaces that flow seamlessly for both everyday living and effortless entertaining. Elevated above street level, the property enjoys enhanced privacy and light. The main level includes a parlor with a gas fireplace that you could convert to a bedroom and full bath, offering flexibility for guests, office space, or multigenerational living. Thoughtful upgrades blend modern comfort with timeless character. Recent improvements include a newer kitchen island, a porch enclosure with mini-split HVAC (2019), and a floating deck with a new roof off the primary bedroom (2023)—creating inviting outdoor spaces for relaxing and entertaining. Practical enhancements provide peace of mind, including two new HVAC systems (2025) and a hot water heater with recirculating pump (2026). Bump outs in the family room, dining room and primary bedroom enhance the living spaces. Craftsman-inspired fir siding, a fully fenced private yard with amazing landscaping, and multiple outdoor living spaces complete this rare downtown offering. A property that combines historic Annapolis charm, modern updates, exceptional parking, and walkable convenience—this is downtown living at its very best!
Listed By
Agency Name: Long & Foster Real Estate, Inc.
Agency Phone: 4102633400
Shown By
Agent Name: Eileen Voyles
Agent Phone: (717) 508-4610
Agency Title: Berkshire Hathaway HomeServices Homesale Realty
Estimated Payment
$ 8,418.28 per month $6,009.03 Principal & Interest $1,621.75 Property Tax $787.50 Homeowner's Insurance
98 Duke Of Gloucester Street | MLS# MDAA2139684
This single family home located at 98 Duke Of Gloucester Street, Annapolis, MD 21401 is currently listed for sale with an asking price of $2,700,000. This property was built in 1915 and has 4 bedrooms and 3 full baths with 3565 sq. ft. Duke Of Gloucester Street is located in the HISTORIC DISTRICT subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search HISTORIC DISTRICT real estate on www.eileenvoyles.com today.