Downtown Annapolis Homes

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  $275,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft

  26 Pleasant St, Annapolis, MD 21401

  NEW PRICE! Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife. Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly

  Matthew Wyble Next Step Realty

  26 Pleasant St, Annapolis, MD 21401
• Explore Downtown Annapolis

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  Call for Price

  Timothy House & Gardens

  1 - 3 Beds

  29 W Washington St, Annapolis, MD 21401

  Timothy House & Gardens is located in the Downtown Annapolis Neighborhood and 21401 Zip code of Annapolis, MD.

  29 W Washington St, Annapolis, MD 21401
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  $1,400,000 Sold Jul 21, 2025

  138 Charles St, Annapolis, MD 21401

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft
  • Built 1887

  Last Sold Summary

  • $452/SF
  • 24 Days On Market

  Current Estimated Value $1,409,146

  Last Listing Agent Alex Tower Sears TTR Sotheby's International Realty

  138 Charles St, Annapolis, MD 21401
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  Est $197,000 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  33 East St Unit 1, Annapolis, MD 21401

  33 East St Unit 1, Annapolis, MD 21401
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  $1,375,000

  • 4 Beds
  • 3 Baths
  • 2,649 Sq Ft

  165 King George St, Annapolis, MD 21401

  There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while

  Michele Michael CENTURY 21 New Millennium

  165 King George St, Annapolis, MD 21401
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  $2,145 per month

  • 1 Bath
  • 505 Sq Ft
  • Condo for Rent

  180 Main St Unit 202, Annapolis, MD 21401

  Welcome to Downtown Annapolis living at its finest! This fully furnished studio apartment is ideally located on Main Street, surrounded by historic charm, waterfront views, and the vibrant energy of the city. Enjoy the downtown Annapolis lifestyle of local restaurants, boutique shopping, the State House, City Dock, and Ego Alley. Take part in beloved community events like Midnight Madness and the

  Sarah Horwath Long & Foster Real Estate, Inc.

  180 Main St Unit 202, Annapolis, MD 21401
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  $1,425,000 Sold Apr 29, 2025

  144 Charles St, Annapolis, MD 21401

  • 4 Beds
  • 3.5 Baths
  • 2,089 Sq Ft
  • Built 1900

  Last Sold Summary

  • $682/SF
  • 5 Days On Market

  Current Estimated Value $1,389,914

  Last Listing Agent Kate Hopkins Coldwell Banker Realty

  144 Charles St, Annapolis, MD 21401
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  Est $1,082,364 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,873 Sq Ft

  66 Franklin St Unit 411, Annapolis, MD 21401

  66 Franklin St Unit 411, Annapolis, MD 21401
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  $1,150,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  168 Green St, Annapolis, MD 21401

  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 original hardwood floors, a classic Queen Anne façade with its distinctive mansard roof, and a welcoming front porch, while also offering the comfort of thoughtful modern updates. Inside, history meets convenience. Three gas

  Luke Rozansky Compass

  168 Green St, Annapolis, MD 21401
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  $2,100 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  126 Prince George St Unit 4, Annapolis, MD 21401

  The heart of Annapolis 1 street from the harbor. This 2nd floor 1 bedroom / 1 bath aprox 600SQ condo has been renovated with new paint, carpet and new kitchen. Split hvac system, so you will control your own ac/heat. Washer/Dryer in the unit. Secure building with locked entry. 1 flight of stairs no one sharing walls with. Water included and wifi for $40 a month

  Nathan Johnson Keller Williams Capital Properties

  126 Prince George St Unit 4, Annapolis, MD 21401
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  $900,000 Sold Mar 27, 2025

  102 South St, Annapolis, MD 21401

  • 3 Beds
  • 2.5 Baths
  • 1,256 Sq Ft
  • Built 1918

  Last Sold Summary

  • $717/SF
  • 5 Days On Market

  Current Estimated Value $864,084

  Last Listing Agent Alex Tower Sears TTR Sotheby's International Realty

  102 South St, Annapolis, MD 21401
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  Est $2,466,241 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,053 Sq Ft

  5 S Acton Place, Annapolis, MD 21401

  5 S Acton Place, Annapolis, MD 21401
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  $599,900

  • Studio
  • 2,300 Sq Ft

  212 Duke of Gloucester St, Annapolis, MD 21401

  Welcome to 212 Duke of Gloucester- a prime development opportunity in the heart of historic Annapolis-- Steps away from Church circle, this 2300 sqft split level property built in 1946 is ready for your vision. This property is ideal for visionary investors or developers seeking to create a signature residential, commercial, or mixed-use project. While the zoning is C2P which allows both

  Nicholas Pfisterer RE/MAX Advantage Realty

  212 Duke of Gloucester St, Annapolis, MD 21401
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  $4,100 per month

  • 4 Beds
  • 3.5 Baths
  • 1,990 Sq Ft
  • Townhouse for Rent

  151 Duke of Gloucester St, Annapolis, MD 21401

  Absolutely Gorgeous Historic Annapolis home , full of the charm and style yet completely restored with all of the modern conveniences . Close to everything 1 block from main street.....City Dock, Bar, Restaurants...... across from City Hall, Close to spa creek ..... Come sit back and enjoy the Annapolis life style.Pets allowed with non refundable pet fee of $250 per Pet and $50 a month

  Heather Edmond Keller Williams Flagship

  151 Duke of Gloucester St, Annapolis, MD 21401
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  $815,000 Sold Mar 17, 2025

  263 Hanover St, Annapolis, MD 21401

  • Studio
  • 2,770 Sq Ft
  • Built 1900

  Last Sold Summary

  • $294/SF
  • 9 Days On Market

  Current Estimated Value $895,301

  Last Listing Agent Ginna Quinn Coldwell Banker Realty

  263 Hanover St, Annapolis, MD 21401
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  Est $569,620 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,138 Sq Ft

  5 Maryland Ave Unit 5, Annapolis, MD 21401

  5 Maryland Ave Unit 5, Annapolis, MD 21401
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  $1,695,000

  • 2 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  51 Franklin St, Annapolis, MD 21401

  An exclusive and rare opportunity could be yours! Welcome to 51 Franklin, consisting of 9 high-end boutique units, developed by John Pilli & constructed by Gate One custom builders in 2020. Located at the intersection of Murray Hill and the city's Historic District, this exquisite condo provides high-end finishes including Legno-Bastone wide-plank hardwood flooring, Caesarstone waterfall

  Yael Beckman Coldwell Banker Realty

  51 Franklin St, Annapolis, MD 21401
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  $3,100,000 Sold Jun 27, 2025

  21 Southgate Ave, Annapolis, MD 21401

  • 4 Beds
  • 3.5 Baths
  • 3,591 Sq Ft
  • Built 1890

  Last Sold Summary

  • $863/SF
  • 6 Days On Market

  Current Estimated Value $3,054,686

  Last Listing Agent Elizabeth Dooner Coldwell Banker Realty

  21 Southgate Ave, Annapolis, MD 21401
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  Est $740,679 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,026 Sq Ft

  28 Fleet St, Annapolis, MD 21401

  28 Fleet St, Annapolis, MD 21401
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  $2,100,000

  • 4 Beds
  • 2.5 Baths
  • 4,404 Sq Ft

  41 Cornhill St, Annapolis, MD 21401

  Price Reduction! Seller says to bring all offers! Built by Captain Beriah Maybury in 1772 and known as the Kings' Arms Tavern, this Historically designated property is a MUST SEE! This Five-Bay wide brick Single Family Home sits on top of a high scored stone foundation. 9.5 foot ceilings illuminated by nearly floor to ceiling windows showcase a lovely Library with built-In Bookcases and a wood

  Lorain Shore Expert Realty, LLC.

  41 Cornhill St, Annapolis, MD 21401
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  $700,000 Sold Nov 14, 2025

  66 Franklin St Unit 201, Annapolis, MD 21401

  • 2 Beds
  • 2.5 Baths
  • 1,366 Sq Ft
  • Built 2007

  Last Sold Summary

  • $512/SF
  • 7 Days On Market

  Last Listing Agent Deborah Laggini Long & Foster Real Estate, Inc.

  66 Franklin St Unit 201, Annapolis, MD 21401
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  Est $1,398,212 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  22 South St, Annapolis, MD 21401

  22 South St, Annapolis, MD 21401
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  $1,200,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  32 East St, Annapolis, MD 21401

  Kevin Cooke Coldwell Banker Realty

  32 East St, Annapolis, MD 21401
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  $1,212,500 Sold Oct 10, 2025

  237 Hanover St, Annapolis, MD 21401

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Built 1875

  Last Sold Summary

  • $758/SF
  • 1 Day On Market

  Last Listing Agent Merritt Butts Long & Foster Real Estate, Inc.

  237 Hanover St, Annapolis, MD 21401
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  Est $1,872,013 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,531 Sq Ft

  54 Franklin St, Annapolis, MD 21401

  54 Franklin St, Annapolis, MD 21401
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  $1,975,000

  • 3 Beds
  • 2.5 Baths
  • 3,884 Sq Ft

  2 Southgate Ave Unit 10, Annapolis, MD 21401

  Elegant charm meets modern convenience in this one-of-a-kind residence located in the heart of Murray Hill. Offering the very best of the downtown lifestyle, this remarkable property boasts a chef’s kitchen with custom cabinetry, granite counters, and high-end appliances and soaring ceilings. The stunning Living room with gas fireplace and light filled dining area flows seamlessly to the

  Brad Kappel TTR Sotheby's International Realty

  2 Southgate Ave Unit 10, Annapolis, MD 21401
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  $500,000 Sold Dec 12, 2025

  212 King George St, Annapolis, MD 21401

  • 1 Bed
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1935

  Last Sold Summary

  • $496/SF
  • 6 Days On Market

  Last Listing Agent Megan Burke Keller Williams Flagship

  212 King George St, Annapolis, MD 21401
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  Est $845,200 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft

  32 City Gate Ln, Annapolis, MD 21401

  32 City Gate Ln, Annapolis, MD 21401
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  $1,599,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 2,544 Sq Ft

  51 Richards Ln, Annapolis, MD 21401

  New Price.....Located just a block from the waterfront park and within easy walking distance to the heart of downtown Annapolis, this beautifully renovated, end-of-row townhouse has been thoughtfully updated throughout. The home features a bright, open layout and high quality finishes including a spectacular Kitchen and lovely Primary Bathroom. There are plantation shutters throughout, wood

  Day Weitzman Coldwell Banker Realty

  51 Richards Ln, Annapolis, MD 21401
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  $875,000 Sold Aug 29, 2025

  48 Cornhill St, Annapolis, MD 21401

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • Built 1850

  Last Sold Summary

  • $604/SF
  • 12 Days On Market

  Current Estimated Value $882,093

  Last Listing Agent Dawn Riley RE/MAX One

  48 Cornhill St, Annapolis, MD 21401
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  Est $1,323,945 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  10 Cheston Ave, Annapolis, MD 21401

  10 Cheston Ave, Annapolis, MD 21401
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  $699,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  66 Franklin St Unit 101, Annapolis, MD 21401

  Black Friday comes early in downtown Annapolis! Now offered at $699,000, this stunning 2-bedroom, 2-bath condo in Acton’s Landing delivers incredible value in one of the city’s most sought-after communities. With soaring 9-foot ceilings, floor-to-ceiling windows, and beautifully updated finishes, every detail shines. Enjoy secure garage parking, a private storage unit, and resort-style amenities

  Heather Giovingo Coldwell Banker Realty

  66 Franklin St Unit 101, Annapolis, MD 21401
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  $3,400,000 Sold Apr 21, 2025

  114 Duke of Gloucester St, Annapolis, MD 21401

  • 5 Beds
  • 3.5 Baths
  • 4,440 Sq Ft
  • Built 1774

  Last Sold Summary

  • $766/SF
  • 0 Days On Market

  Current Estimated Value $3,349,923

  Last Listing Agent Elizabeth Dooner Coldwell Banker Realty

  114 Duke of Gloucester St, Annapolis, MD 21401
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  Est $1,029,482 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,498 Sq Ft

  108 Market St, Annapolis, MD 21401

  108 Market St, Annapolis, MD 21401
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  $3,750,000

  • 5 Beds
  • 3.5 Baths
  • 6,789 Sq Ft

  39 Southgate Ave, Annapolis, MD 21401

  This Murray Hill masterpiece is a 5-bedroom, 4 bathroom home that was originally built in 1913 and underwent a complete custom renovation a few years ago. Situated on a double lot on one of the most desirable streets in Annapolis. It blends formal sophistication with modern luxuries including an elevator! Offering rare private driveway, a two-car garage with separate storage room. Featuring over

  Glenn Sutton TTR Sotheby's International Realty

  39 Southgate Ave, Annapolis, MD 21401
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  $215,000 Sold Jul 15, 2025

  63 Town Pines Ct, Annapolis, MD 21401

  • 3 Beds
  • 1.5 Baths
  • 1,037 Sq Ft
  • Built 1975

  Last Sold Summary

  • $207/SF
  • 31 Days On Market

  Current Estimated Value $218,439

  Last Listing Agent Martin Tippet ExecuHome Realty

  63 Town Pines Ct, Annapolis, MD 21401
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  Est $714,553 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 910 Sq Ft

  88 Charles St, Annapolis, MD 21401

  88 Charles St, Annapolis, MD 21401
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  $3,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,621 Sq Ft

  9 Shipwright St, Annapolis, MD 21401

  Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and

  Brad Kappel TTR Sotheby's International Realty

  9 Shipwright St, Annapolis, MD 21401
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  $587,000 Sold Jul 24, 2025

  11 1/2 College Ave, Annapolis, MD 21401

  • 2 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • Built 1784

  Last Sold Summary

  • $405/SF
  • 5 Days On Market

  Current Estimated Value $610,484

  Last Listing Agent Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

  11 1/2 College Ave, Annapolis, MD 21401
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  Est $1,478,444 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,652 Sq Ft

  55 Richards Ln, Annapolis, MD 21401

  55 Richards Ln, Annapolis, MD 21401

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