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!
Sold for $3,050,000
Zillow last checked:
Listing updated:
Bought with:
Elizabeth Dooner, 631665
Coldwell Banker Realty
Source: Bright MLS,MLS#: MDAA2139684
Price history
| Date | Event | Price |
|---|---|---|
| 4/30/2026 | Sold | $3,050,000+13%$856/sqft |
Source:  Bright MLS #MDAA2139684 Report a problem | ||
| 4/14/2026 | Pending sale | $2,700,000$757/sqft |
Source: Bright MLS #MDAA2139684 Report a problem | ||
| 4/8/2026 | Listed for sale | $2,700,000+92.9%$757/sqft |
Source: Bright MLS #MDAA2139684 Report a problem | ||
| 2/14/2018 | Sold | $1,400,000-15.2%$393/sqft |
Source: Public Record Report a problem | ||
| 10/17/2017 | Listing removed | $1,650,000$463/sqft |
Source: TTR Sotheby's International Realty #AA9925689 Report a problem | ||
| 7/26/2017 | Price change | $1,650,000-5.7%$463/sqft |
Source: TTR Sotheby's International Realty #AA9925689 Report a problem | ||
| 4/25/2017 | Price change | $1,750,000+3%$491/sqft |
Source: Owner Report a problem | ||
| 4/8/2017 | Price change | $1,699,000-0.1%$477/sqft |
Source: Owner Report a problem | ||
| 4/6/2017 | Price change | $1,700,000-2.9%$477/sqft |
Source: Owner Report a problem | ||
| 3/30/2017 | Listed for sale | $1,750,000+184.6%$491/sqft |
Source: Owner Report a problem | ||
| 6/9/2014 | Sold | $615,000-10.7%$173/sqft |
Source: Public Record Report a problem | ||
| 3/1/2014 | Listing removed | $689,000$193/sqft |
Source: Champion Realty #AA8272691 Report a problem | ||
| 2/17/2014 | Listed for sale | $689,000-0.9%$193/sqft |
Source: Champion Realty #AA8272691 Report a problem | ||
| 10/31/2013 | Listing removed | $695,000$195/sqft |
Source: Long & Foster Real Estate #AA8056204 Report a problem | ||
| 9/4/2013 | Price change | $695,000-7.3%$195/sqft |
Source: Long & Foster Real Estate #AA8056204 Report a problem | ||
| 7/24/2013 | Price change | $750,000-9%$210/sqft |
Source: Long & Foster Real Estate #AA8056204 Report a problem | ||
| 4/17/2013 | Listed for sale | $824,000-10.9%$231/sqft |
Source: Long & Foster Real Estate #AA8056204 Report a problem | ||
| 1/31/2013 | Listing removed | $925,000$259/sqft |
Source: Long & Foster Real Estate #AA7977721 Report a problem | ||
| 12/18/2012 | Listed for sale | $925,000$259/sqft |
Source: Long & Foster Real Estate #AA7977721 Report a problem | ||
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Estimated market value
$3,042,500
