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16 Dean St, Annapolis image
16 Dean St, Annapolis $695,000

Tucked along a quiet one-way street in the heart of Historic Downtown Annapolis, this charming residence offers the perfect blend of character, convenience, and an except...

  • 1 Beds
  • 2 Baths
  • MDAA2150940 MLS
254 King George   Street, Annapolis image
254 King George Street, Annapolis $1,930,000

The Henry Brown House, Circa 1860, is a distinguished residence once associated with Charles Hammond and Richard Harwood, with earlier ties to William Paca. Ideally posit...

  • 4 Beds
  • 3 Baths
  • MDAA2143686 MLS
22 College   Avenue, Annapolis image
22 College Avenue, Annapolis $900,000

Open House Canceled- Under Contract! Phenomenal Downtown property was the winner of Historic Annapolis Foundation's Renovation award! Overflowing with charm and personali...

  • 3 Beds
  • 2 Baths
  • MDAA2148978 MLS
45 Fleet St, Annapolis image
45 Fleet St, Annapolis $824,995

A rare opportunity to own one of Annapolis' most distinguished historic residences, thoughtfully restored to preserve its extraordinary heritage while seamlessly incorpor...

  • 2 Beds
  • 1 Baths
  • MDAA2150298 MLS
89 Shipwright   Street, Annapolis image
89 Shipwright Street, Annapolis $2,035,000

Classic, white-shingled Colonial on one of the prettiest streets in Annapolis! Expanded rear yard, parking for 2–3 cars, and views of Spa Creek. Two rear porches, heart o...

  • 4 Beds
  • 4 Baths
  • MDAA2148056 MLS
111 Conduit St, Annapolis image
111 Conduit St, Annapolis $985,000 ▲

111 Conduit Street is historic Annapolis living at its finest. Nestled in the heart of Historic Annapolis, this charming semi-detached residence seamlessly blends timele...

  • 4 Beds
  • 3 Baths
  • MDAA2150170 MLS
12 Union St, Annapolis image
12 Union St, Annapolis $1,289,900 ▼

Rare opportunity to own a stunning newer built fully detached four bedroom home in the historic district with an attached one car garage plus a one car driveway​ —an amen...

  • 4 Beds
  • 2 Baths
  • MDAA2149666 MLS
90 Charles   Street, Annapolis image
90 Charles Street, Annapolis $1,050,000

Welcome to 90 Charles Street, a rare opportunity to own a beautifully maintained home in the heart of historic downtown Annapolis. Perfectly positioned just steps from Ac...

  • 3 Beds
  • 3 Baths
  • MDAA2141482 MLS
141 West   Street Unit #201, Annapolis image
141 West Street Unit #201, Annapolis $472,000

Welcome to 141 West a boutique building styled after one of Manhattan’s most iconic neighborhoods SoHo, known for its historic cast iron architecture. At 141 West the hi...

  • 1 Beds
  • 1 Baths
  • MDAA2138542 MLS
38 Cathedral   Street, Annapolis image
38 Cathedral Street, Annapolis $684,000

Tucked into the heart of downtown Annapolis, this charming home offers an effortless lifestyle where everything you love is just outside your door. Start your mornings wi...

  • 2 Beds
  • 2 Baths
  • MDAA2142154 MLS
11 1/2 College Ave, Annapolis image
11 1/2 College Ave, Annapolis $1,295,000 ▼

OPEN HOUSE this SATURDAY 12-2PM and SUNDAY 10AM - 12PM. Now offered at an exceptional value in today's market. One of the most stunning renovations to come on the market ...

  • 3 Beds
  • 3 Baths
  • MDAA2147924 MLS
238 King George St, Annapolis image
238 King George St, Annapolis $2,950,000

Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps from State Circle, the United States Naval Academy, City Dock, waterfront dining...

  • 4 Beds
  • 5 Baths
  • MDAA2147930 MLS
21 City Gate   Lane, Annapolis image
21 City Gate Lane, Annapolis $860,000

Move-in ready end-unit townhome in the heart of downtown Annapolis! This eye-catching, low-maintenance brick home offers 3 bedrooms, 3 full baths, and 1 half bath, thoug...

  • 3 Beds
  • 4 Baths
  • MDAA2141590 MLS
87 Shipwright St, Annapolis image
87 Shipwright St, Annapolis $1,850,000

Located in Annapolis' Historic District, this 4 story home offers a rare opportunity to own a spacious residence within walking distance of the water, City Dock, shops, r...

  • 6 Beds
  • 5 Baths
  • MDAA2146930 MLS
163 Prince George   Street, Annapolis image
163 Prince George Street, Annapolis $1,325,000

Exceptional new pricing creates a compelling offering in the heart of Historic Annapolis. Located on one of the most charming and desirable streets in Historic Annapolis...

  • 3 Beds
  • 3 Baths
  • MDAA2137556 MLS
32 Cornhill St, Annapolis image
32 Cornhill St, Annapolis $774,900 ▼

Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely renovated and remodeled in 2023. New kitchen, new bathroom, recessed lights, new...

  • 2 Beds
  • 2 Baths
  • MDAA2146252 MLS
16 Maryland Ave, Annapolis image
16 Maryland Ave, Annapolis $3,849,000

A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home m...

  • 6 Beds
  • 5 Baths
  • MDAA2142212 MLS
34 Pinkney St, Annapolis image
34 Pinkney St, Annapolis $685,000 ▼

How many times have you strolled Annapolis' streets and thought, "I wish I lived here!"? 34 Pinkney is your opportunity to be in the center of the good life Annapolis has...

  • 2 Beds
  • 2 Baths
  • MDAA2145798 MLS
158 Prince George St, Annapolis image
158 Prince George St, Annapolis $1,425,000 ▼

RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significa...

  • 3 Beds
  • 3 Baths
  • MDAA2143444 MLS
192 Duke Of Gloucester, Annapolis image
192 Duke Of Gloucester, Annapolis $1,950,000

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style...

  • 6 Beds
  • 4 Baths
  • MDAA2144086 MLS
98 Duke Of Gloucester   Street, Annapolis image
98 Duke Of Gloucester Street, Annapolis $3,050,000

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 he...

  • 4 Beds
  • 3 Baths
  • MDAA2139684 MLS
5 Market Quay, Annapolis image
5 Market Quay, Annapolis — Market Quay $3,499,000 ▼

Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design and an impeccable lock and l...

  • 4 Beds
  • 5 Baths
  • MDAA2143742 MLS
  • Market Quay Bldg.
83 Market St, Annapolis image
83 Market St, Annapolis $2,295,000 ▼

This exceptional Historic District home combines the charm of a classic Annapolis address with a substantial 2026 renovation in all the right places. A stunning new kitch...

  • 5 Beds
  • 4 Baths
  • MDAA2143042 MLS
75 Shipwright St, Annapolis image
75 Shipwright St, Annapolis $1,449,000 ▼

75 Shipwright Street is an enchanting Victorian semi-detached home located in the heart of the Historic District of downtown Annapolis. This is a rare opportunity to own ...

  • 5 Beds
  • 4 Baths
  • MDAA2141982 MLS
79 Charles   Street, Annapolis image
79 Charles Street, Annapolis $855,000

The perfect Downtown Annapolis home and location! This great blend of old and new, melds lots of beautiful original material with modern updates like an open floor plan ...

  • 3 Beds
  • 2 Baths
  • MDAA2136158 MLS
167 Prince George   Street, Annapolis image
167 Prince George Street, Annapolis $865,000

OPEN HOUSE HAS BEEN MOVED TO SATURDAY JANUARY 24TH FROM 1-3 PM Situated on one of Historic Annapolis’ most desirable streets, this circa-1815 row house offers a rare comb...

  • 2 Beds
  • 3 Baths
  • MDAA2132236 MLS
1 Shipwright Harbor, Annapolis image
1 Shipwright Harbor, Annapolis $5,675,000 ▼

Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winn...

  • 3 Beds
  • 4 Baths
  • MDAA2132250 MLS
54 Cornhill   Street, Annapolis image
54 Cornhill Street, Annapolis $875,000

Stunningly Updated Historic District Charmer, One Block From The Water/Ego Alley! Nestled near the top of iconic Cornhill Street—just steps from State Circle and the bout...

  • 3 Beds
  • 3 Baths
  • MDAA2130498 MLS
168 Green   Street, Annapolis image
168 Green Street, Annapolis $1,098,000

There’s a timeless allure to this cheerful yellow home on Green Street. Built in the 1870s as part of Annapolis’s historic core, it retains the character of its era with ...

  • 3 Beds
  • 3 Baths
  • MDAA2128222 MLS
32 East   Street, Annapolis image
32 East Street, Annapolis $1,035,000

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  • 3 Beds
  • 3 Baths
  • MDAA2128006 MLS
76 East   Street, Annapolis image
76 East Street, Annapolis $870,000

Fro Appraisers: Property went under contract before going live. Property was sold as-is w/o inspections with buyers agent contributing 1%. Stately three bedroom home in...

  • 3 Beds
  • 2 Baths
  • MDAA2129526 MLS
222 West   Street Unit #A, Annapolis image
222 West Street Unit #A, Annapolis $710,000

A thoughtfully designed residence offering a blend of historic character and modern comfort in the heart of Downtown Annapolis. Nestled amongst the city's best dining, sh...

  • 2 Beds
  • 3 Baths
  • MDAA2128240 MLS
165 King George St, Annapolis image
165 King George St, Annapolis $1,375,000

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...

  • MDAA2132270 MLS
165 King George St, Annapolis image
165 King George St, Annapolis $1,375,000

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...

  • 4 Beds
  • 3 Baths
  • MDAA2132242 MLS
141 West   Street Unit #403, Annapolis image
141 West Street Unit #403, Annapolis $1,480,000

In the heart of Downtown Annapolis Art District, this Rare, LUXURY PENTHOUSE captures the essence of refined living with sweeping views, refined finishes, and a terrace u...

  • 3 Beds
  • 3 Baths
  • MDAA2126138 MLS
39 Cornhill   Street, Annapolis image
39 Cornhill Street, Annapolis $1,050,000

This historic and inviting Colonial home, built in 1786, is uniquely charming with large, elegant living spaces. Full of sophistication, it is also exceptionally comforta...

  • 3 Beds
  • 2 Baths
  • MDAA2127644 MLS
115 Charles   Street, Annapolis image
115 Charles Street, Annapolis $830,000

OFFER DEADLINE - TUESDAY OCT 14 @ 5M. Live the Annapolis lifestyle in this beautifully updated historic district colonial. Tucked on a quiet street just blocks from down...

  • 3 Beds
  • 2 Baths
  • MDAA2127584 MLS
107 Charles   Street, Annapolis image
107 Charles Street, Annapolis $870,000

Charming, turn-key jewel box in the heart of downtown Annapolis. This 3 bedroom, 2.5 bath historic home features original heart of pine floors, high ceilings, a welcomin...

  • 3 Beds
  • 3 Baths
  • MDAA2123874 MLS
237 Hanover   Street, Annapolis image
237 Hanover Street, Annapolis $1,212,500

This is a rare opportunity to own a well-documented (MHA) Greek Revival home on quiet Hanover St. facing USNA across from Officers' Club., very close to Gate 3 and the N...

  • 3 Beds
  • 3 Baths
  • MDAA2124536 MLS
83 Market   Street, Annapolis image
83 Market Street, Annapolis $2,150,000

Absolutely stunning home on the idyllic waterside of Market St. - just a stone's throw from the waterfront, enjoy seasonal water views from several places within the home...

  • 4 Beds
  • 4 Baths
  • MDAA2123192 MLS
48 Cornhill   Street, Annapolis image
48 Cornhill Street, Annapolis $875,000

In the shade of the Statehouse, nestled on a quiet side street, there is a comfortable and elegant home that has welcomed family, friends, and guests for 175 years. This...

  • 3 Beds
  • 2 Baths
  • MDAA2121434 MLS
96 Conduit   Street, Annapolis image
96 Conduit Street, Annapolis $1,075,000

Experience timeless charm and modern living at 96 Conduit Street — a residence in the heart of Historic Downtown Annapolis. Nestled on a quiet street just steps from Sp...

  • 3 Beds
  • 2 Baths
  • MDAA2121284 MLS
17 Revell   Street, Annapolis image
17 Revell Street, Annapolis $11,250,000

Welcome to the ultimate Spa Creek waterfront oasis! Enjoy living in the heart of historic Downtown Annapolis with walkability to everything the area has to offer includin...

  • 4 Beds
  • 7 Baths
  • MDAA2115242 MLS
143 Market   Street, Annapolis image
143 Market Street, Annapolis $999,999

Nestled in the heart of downtown Annapolis, right on storied Market Street, this beautifully updated detached historic home seamlessly blends timeless charm with modern c...

  • 2 Beds
  • 3 Baths
  • MDAA2103450 MLS
60 Cornhill   Street, Annapolis image
60 Cornhill Street, Annapolis $1,650,000

Exquisitely renovated, perfect in-town residence with parking in the shadow of the State House! From the moment you enter, you will be wowed with the pretty detail and l...

  • 3 Beds
  • 4 Baths
  • MDAA2119022 MLS
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...

  • MDAA2118516 MLS
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
  • MDAA2118606 MLS
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
  • MDAA2108604 MLS
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
  • MDAA2111466 MLS
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
  • MDAA2118978 MLS

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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