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11 1/2 College Avenue, Annapolis image
11 1/2 College Avenue, Annapolis $587,000

Amazing renovation opportunity in the heart of Annapolis, literally a stone's throw from the Naval Academy! 2 separate legal units, separately metered for gas and electri...

  • 2 Beds
  • 2 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: .

146 Duke Of Gloucester Street, Annapolis image
146 Duke Of Gloucester Street, Annapolis $1,399,900

Experience Historic Charm & Modern Elegance in the Heart of Annapolis. Nestled in the heart of downtown Annapolis, this stunning historic Federal-style home offers the ...

  • 4 Beds
  • 4 Baths
Courtesy of Real Broker, LLC - Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: .

138 Charles Street, Annapolis image
138 Charles Street, Annapolis $1,400,000

Just Reduced! First time on the market in 40 years! This is a rare and special opportunity to own a detached home with both a garage and driveway in The Historic District...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

173 Prince George Street, Annapolis image
173 Prince George Street, Annapolis $950,000

Rare, modern (1978) built detached home in the Historic District with newly renovated kitchen featuring inset cabinets and wide plank wood floors! Excellent open floor p...

  • 3 Beds
  • 2 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

11 Southgate Avenue, Annapolis image
11 Southgate Avenue, Annapolis $3,517,500

A truly unique opportunity to enjoy your own private dock on Spa Creek from this classic totally renovated home on the prettiest block of the prettiest street in Annapoli...

  • 5 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

141 West Street Unit #206, Annapolis image
141 West Street Unit #206, Annapolis $730,000

Luxury, walkability, and convenience converge at West141 in the heart of Downtown Annapolis. This two-bedroom, two-bath condo offers a modern design, direct access to the...

  • 2 Beds
  • 2 Baths
Courtesy of Real Broker, LLC - Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: .

88 Market Street, Annapolis image
88 Market Street, Annapolis $1,460,000

OPEN HOUSE SCHEDULED FOR SUNDAY, MAY 18th HAS BEEN CANCELLED. UNDER CONTRACT!! ATTENTION WOULD-BE ANNAPOLITANS !!! RARE OPPORTUNITY TO OWN and LUXURIOUSLY ABIDE IN RESTO...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

24 Fleet Street, Annapolis image
24 Fleet Street, Annapolis $700,000

*Seller has an offer in hand. Please submit best and final by 9PM EST Monday, May 12, 2025. Seller will review offers and make a decision on TuesdayMay 12, 2025 - seller ...

  • 2 Beds
  • 2 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

101 Charles Street, Annapolis image
101 Charles Street, Annapolis $900,000

Here is your excellent investment opportunity in this perfect in town location with three turnkey apartment units and a parking space. All units have separate entrances...

Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

101 Charles Street, Annapolis image
101 Charles Street, Annapolis $900,000

Excellent investment opportunity in this perfect in town location with three turnkey apartment units and a parking space. All units have separate entrances, utilities a...

  • 4 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

144 Charles Street, Annapolis image
144 Charles Street, Annapolis $1,425,000

Timeless Elegance in the Heart of Historic Annapolis. Tucked away on one of Annapolis’ most charming streets, this circa-1900 home blends historic character with thought...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

114 Duke Of Gloucester Street, Annapolis image
114 Duke Of Gloucester Street, Annapolis $3,400,000

One of the most historic and distinguished homes in Downtown Annapolis. This beautifully maintained residence combines timeless charm with modern livability. Gracious pro...

  • 5 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

102 South Street, Annapolis image
102 South Street, Annapolis $900,000

A truly rare and spectacular home just completed and totally renovated in the heart of Annapolis' Historic District! It is like having a brand new townhouse in Downtown A...

  • 3 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

22 Dean Street Unit #2, Annapolis image
22 Dean Street Unit #2, Annapolis — Dean Street Condominium $1,260,000

This exquisite three-bedroom, three-and-a-half-bath townhome-style condo in Historic Annapolis offers not just luxury and charm but also the rare convenience of two dedic...

  • 3 Beds
  • 4 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

170 Green Street, Annapolis image
170 Green Street, Annapolis $905,000

Welcome to the epitome of Annapolis charm! Nestled in the heart of the historic district, this stunning 1870 Victorian home—with its historic plaque—offers an extraordina...

  • 3 Beds
  • 3 Baths
Courtesy of Keller Williams Realty Delmarva

Listing courtesy of Keller Williams Realty Delmarva. Contact:

Selling Office: .

163 Prince George Street, Annapolis image
163 Prince George Street, Annapolis $1,350,000

Nestled on one of the most picturesque and sought-after streets in Historic Annapolis, this stunning 3-bedroom, 2.5-bathroom home beautifully blends 19th-century charm wi...

  • 3 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

107 Conduit Street, Annapolis image
107 Conduit Street, Annapolis $1,550,000

The historic Smith House is a charming 4-unit home in the heart of downtown Annapolis, steps from Main Street and in the city's most desirable area. The home is the perfe...

Courtesy of Berkshire Hathaway HomeServices PenFed Realty

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: .

40 Cornhill Street, Annapolis image
40 Cornhill Street, Annapolis $2,900,000

Two perfect 18-century homes being sold together. 40 and 38 Cornhill is an exquisite residence in the heart of Downtown Annapolis. Flawlessly renovated and updated with...

  • 5 Beds
  • 7 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

247 King George Street, Annapolis image
247 King George Street, Annapolis $2,850,000

Ogle Hall - This property, originally erected in 1739 - 1742 (Georgian Style), once served as a residence for Maryland Governor Samuel Ogle, as well as two future MD Gov...

  • 5 Baths
Courtesy of Rosso Commercial Real Estate Services, LLC.

Listing courtesy of Rosso Commercial Real Estate Services, LLC.. Contact:

Selling Office: .

102 Charles Street, Annapolis image
102 Charles Street, Annapolis $709,000

​Charming 2-bedroom, 2.5-bathroom corner townhome located in the heart of sought-after historic downtown Annapolis. This enchanting residence seamlessly blends classic ch...

  • 2 Beds
  • 3 Baths
Courtesy of Keller Williams Realty Centre

Listing courtesy of Keller Williams Realty Centre. Contact:

Selling Office: .

89 East Street, Annapolis image
89 East Street, Annapolis $1,215,000

Location, location, location! This Iconic 1875 Annapolis brick townhome, symbolizes Historic Annapolis with a nod to Charleston charm - brimming with inviting color, sty...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

25 Cathedral Street, Annapolis image
25 Cathedral Street, Annapolis $915,000

Fabulous corner lot in central location in downtown Annapolis !! And.......off street parking in one car garage make this a very desirable home. Hardwood floors throug...

  • 3 Beds
  • 3 Baths
Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: .

196 Duke Of Gloucester Street, Annapolis image
196 Duke Of Gloucester Street, Annapolis $1,859,000

Gorgeous single-family home in a super highly desirable area of Historic Annapolis. 1-4 blocks away from restaurants, shops and the waterfront famously referred to as Eg...

  • 4 Beds
  • 4 Baths
Courtesy of Curtis Real Estate Company

Listing courtesy of Curtis Real Estate Company. Contact:

Selling Office: .

86 East Street, Annapolis image
86 East Street, Annapolis $932,500

Don't miss this beautifully renovated and maintained home in the heart of historic Annapolis with a peaceful, secluded back patio and garden. This 3 bedroom 2 bath histor...

  • 3 Beds
  • 2 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

92 Market Street, Annapolis image
92 Market Street, Annapolis $1,395,000

Nestled on one of the most sought-after streets in downtown Annapolis, this stunning home offers three bedrooms and two and a half bathrooms, including a luxurious primar...

  • 3 Beds
  • 3 Baths
Courtesy of Monument Sotheby's International Realty

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: .

9 Dean Street, Annapolis image
9 Dean Street, Annapolis $986,000

Colonial charm meets modern sophistication at 9 Dean Street in the Historic District of Annapolis, MD . This meticulously restored home, featuring an inviting front porch...

  • 3 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

95 East Street, Annapolis image
95 East Street, Annapolis $688,775

Investors dream in the heart of historic Annapolis. Look out to State Circle from your front porch. Walk to shops and restaurants. Enjoy boat shows, Naval Academy events,...

  • 3 Beds
  • 2 Baths
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: .

111 Market Street, Annapolis image
111 Market Street, Annapolis $957,500

Imagine living in a charming, Historic home on the coveted Market Street, just minutes from the heart of Downtown Annapolis. Picture yourself strolling to Spa Creek, the ...

  • 4 Beds
  • 3 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

2 Market Quay, Annapolis image
2 Market Quay, Annapolis $3,675,000

LOCATION! LOCATION! LOCATION! SPA CREEK WATERFRONT with Pool, Boat Slip and Off-street Parking! Enjoy the sophisticated total remodel of this contemporary end-unit brick ...

  • 4 Beds
  • 4 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

212 Duke Of Gloucester Street, Annapolis image
212 Duke Of Gloucester Street, Annapolis $550,000

Much upside potential exists for this 2,304 sq. ft. brick bi-level just 2 doors down from the Historic Maryland Inn. It's C2P zoning allows both professional offices or r...

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

212 Duke Of Gloucester Street, Annapolis image
212 Duke Of Gloucester Street, Annapolis $550,000

Unique opportunity for historic building in the very heart of downtown Annapolis! Since 2002, the building has served as the home of the New Providence Club, a social cl...

  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

179 Green Street, Annapolis image
179 Green Street, Annapolis $725,000

Priced Reduced - 750,000 with Off Street Parking Behind the Home! This Classic with Period Charm is perfectly located in the Historic District Home just steps from Mai...

  • 3 Beds
  • 1 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

130 Prince George Street, Annapolis image
130 Prince George Street, Annapolis $1,700,000

*Home is under contract with contingency - the owners are still accommodating tours!* You know how every home boasts something is 'one of a kind' or 'once in a lifetime'...

  • 5 Beds
  • 3 Baths
Courtesy of Next Step Realty, LLC.

Listing courtesy of Next Step Realty, LLC.. Contact:

Selling Office: .

3 Dean Street, Annapolis image
3 Dean Street, Annapolis $875,000

Open Houses Scheduled for 8/17 & 8/18 have been Cancelled! USNA Parents, this is the perfect 2nd home! Centrally located for visits; then VRBO when your not in Annapolis...

  • 3 Beds
  • 3 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

92 East Street, Annapolis image
92 East Street, Annapolis $775,000

Charming, Federal-style townhome in the heart of the Historic District built sometime between 1819 and 1831 with a chain of title dating back to 1718! The oldest section ...

  • 2 Beds
  • 2 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

210 King George Street, Annapolis image
210 King George Street, Annapolis $799,000

OPEN HOUSE CANCELLED, Property is now under contract. Newly renovated 3-bedroom home with modern amenities located on prestigious King George Street in the heart of Histo...

  • 3 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

244 Prince George Street, Annapolis image
244 Prince George Street, Annapolis $990,000

OPEN HOUSE CANCELLED - UNDER CONTRACT Charming, renovated 1865 historic home at the top of Prince George Street just steps from St. John's College and around the corner f...

  • 3 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

75 Shipwright Street, Annapolis image
75 Shipwright Street, Annapolis $1,360,000

75 Shipwright Street is a chance to own a piece of history in Annapolis with this enchanting Victorian. Exuding a sense of character and history. Water views of Spa Cre...

  • 5 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

4 Wagner Street, Annapolis image
4 Wagner Street, Annapolis $1,595,000

Discover the epitome of historic charm and modern living in this exquisite 4-bedroom, 3.5-bathroom home nestled in the heart of Annapolis. This distinguished residence of...

  • 4 Beds
  • 4 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

140 Charles Street, Annapolis image
140 Charles Street, Annapolis $1,015,500

Live the ultimate Downtown Annapolis lifestyle in this stunning DETACHED Historic home that offers a unique blend of classic architecture and modern updates. The main lev...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

112 Market Street, Annapolis image
112 Market Street, Annapolis $1,395,000

This historic, charming downtown home has been beautifully updated by the current owners and offers so much of what downtown residents seek - private off-street parking; ...

  • 3 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

171 Prince George Street, Annapolis image
171 Prince George Street, Annapolis $815,000

Welcome home to this spacious home nestled in the heart of Annapolis. The proximity to the Naval Academy, State House, St. John’s College and City Dock is truly fantastic...

  • 2 Beds
  • 3 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

32 Cornhill Street, Annapolis image
32 Cornhill Street, Annapolis $680,000

Welcome home to this beautifully renovated 2 bedroom, 1.5 bathroom townhouse located in the heart of downtown, historic Annapolis. As you step into the home you will find...

  • 2 Beds
  • 2 Baths
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

39 Pinkney Street, Annapolis image
39 Pinkney Street, Annapolis $600,000

ALL OFFERS DUE BY MONDAY MAY 20 @ 10AM EST. SELLER RESERVES THE RIGHT TO ACCEPT AN OFFER PRIOR TO THE DEADLINE IF THEY CHOOSE. Welcome to 39 Pinkney St, a delightful two...

  • 2 Beds
  • 1 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

114 Conduit Street, Annapolis image
114 Conduit Street, Annapolis $1,450,000

3 homes in 1 !! This historic property presents a lucrative investment opportunity, comprised of distinct income generating components-three rental apartments plus an o...

Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: .

45 City Gate Lane, Annapolis image
45 City Gate Lane, Annapolis $850,300

Welcome to your dream townhome in charming Annapolis, MD! This all-brick, end unit residence perfectly blends coastal allure with modern comfort. Nestled on a serene, tr...

  • 3 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

85 Charles Street, Annapolis image
85 Charles Street, Annapolis $815,000

Welcome to 85 Charles Street, a cozy retreat nestled in Historic Annapolis, just a stone's throw away from downtown. With freshly painted interiors, this home offers effo...

  • 3 Beds
  • 2 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

94 Market Street, Annapolis image
94 Market Street, Annapolis $999,999

Seize the chance to own a piece of history in Annapolis with this enchanting Victorian duplex on picturesque lower Market Street. Nestled at the heart of the historic dis...

  • 4 Beds
  • 3 Baths
Courtesy of Monument Sotheby's International Realty

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: .

142 Charles Street, Annapolis image
142 Charles Street, Annapolis $1,395,000

Welcome to this elegantly appointed historic home located on Charles Street in Historic Annapolis. Built sometime between 1880 and 1885 by the Cobbler from the U. S. Nava...

  • 5 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

108 Market Street, Annapolis image
108 Market Street, Annapolis $965,000

Historic charm meets modern style! Own a piece of history that seamlessly blends the old with the new, right in the heart of downtown Annapolis. Since purchasing the pr...

  • 3 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

Historic District Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Historic District, Annapolis MD. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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