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Downtown Annapolis Homes for Sale

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  • 26 Pleasant St, Annapolis, MD 21401
    26 Pleasant St, Annapolis, MD 21401
    26 Pleasant St, Annapolis, MD 21401
    /34

    $349,900

    • 2 Beds
    • 1 Bath
    • 972 Sq Ft

    26 Pleasant St, Annapolis, MD 21401

    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 $40,000

    Matthew Wyble Next Step Realty

    26 Pleasant St, Annapolis, MD 21401
  • 51 Richards Ln, Annapolis, MD 21401
    51 Richards Ln, Annapolis, MD 21401
    51 Richards Ln, Annapolis, MD 21401
    /65

    $1,649,000 Open Sun 12PM - 2PM

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

    51 Richards Ln, Annapolis, MD 21401

    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 floors have been

    Day Weitzman Coldwell Banker Realty

    51 Richards Ln, Annapolis, MD 21401
  • 107 Charles St, Annapolis, MD 21401
    107 Charles St, Annapolis, MD 21401
    107 Charles St, Annapolis, MD 21401
    /31

    $895,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft

    107 Charles St, Annapolis, MD 21401

    JUST LISTED - OPEN THIS WEEKEND! 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 welcoming front porch, an antique decorative fireplace, and abundant natural light. French doors off the kitchen open to a private deck, fenced courtyard, and majestic magnolia tree. A trap door off the

    Sarah Greenlee Morse TTR Sotheby's International Realty

    107 Charles St, Annapolis, MD 21401
  • 42 City Gate Ln, Annapolis, MD 21401
    42 City Gate Ln, Annapolis, MD 21401
    42 City Gate Ln, Annapolis, MD 21401
    /50

    $839,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 4 Baths
    • 1,800 Sq Ft

    42 City Gate Ln, Annapolis, MD 21401

    Welcome to 42 City Gate Lane in the desirable City Gate neighborhood of Annapolis. This move-in ready residence offers 3 bedrooms, 2 full baths, and 2 half baths, thoughtfully updated for modern living. The showpiece main level features a complete open-concept renovation: upgraded cabinetry, a generous center island, sleek quartz counters, and stainless steel appliances—all seamlessly connected

    Mike Kane RE/MAX Distinctive Real Estate, Inc.

    42 City Gate Ln, Annapolis, MD 21401
  • 192 Duke of Gloucester St, Annapolis, MD 21401
    192 Duke of Gloucester St, Annapolis, MD 21401
    192 Duke of Gloucester St, Annapolis, MD 21401
    /61

    $2,200,000 Open Wed 2PM - 4PM

    • 6 Beds
    • 4 Baths
    • 3,415 Sq Ft

    192 Duke of Gloucester St, Annapolis, MD 21401

    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 property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare

    Brian Jacobs Coldwell Banker Realty

    192 Duke of Gloucester St, Annapolis, MD 21401
  • 212 Duke of Gloucester St, Annapolis, MD 21401
    212 Duke of Gloucester St, Annapolis, MD 21401
    212 Duke of Gloucester St, Annapolis, MD 21401
    /23

    $649,999

    • 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

    Ronald Howard RE/MAX Advantage Realty

    212 Duke of Gloucester St, Annapolis, MD 21401
  • 66 Franklin St Unit 20, Annapolis, MD 21401
    66 Franklin St Unit 20, Annapolis, MD 21401
    66 Franklin St Unit 20, Annapolis, MD 21401
    /29

    $750,000

    • 1 Bed
    • 1.5 Baths
    • 1,342 Sq Ft

    66 Franklin St Unit 20, Annapolis, MD 21401

    Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5-bath condo in the sought-after Acton's Landing community. Perfectly situated on the street level for effortless access, this unit combines convenience with luxury. The open-concept layout features a generous living space, a large kitchen with a center island, breakfast bar, and plenty of storage—ideal for a

    John Collins Long & Foster Real Estate, Inc.

    66 Franklin St Unit 20, Annapolis, MD 21401
  • 66 Franklin St Unit 509, Annapolis, MD 21401
    66 Franklin St Unit 509, Annapolis, MD 21401
    66 Franklin St Unit 509, Annapolis, MD 21401
    /36

    $1,850,000

    • 3 Beds
    • 3.5 Baths
    • 2,477 Sq Ft

    66 Franklin St Unit 509, Annapolis, MD 21401

    Gorgeous, One-of-a-Kind Luxury Penthouse in Downtown Annapolis!Welcome to this stunning 3-bedroom, 3.5-bathroom penthouse condo in the exclusive Acton’s Landing community—offering an unparalleled blend of historic charm and sophisticated modern living. With private elevator access, deeded use of two garage parking spaces, and two expansive balconies with breathtaking skyline views, this

    Betty Jans Berkshire Hathaway HomeServices PenFed Realty

    66 Franklin St Unit 509, Annapolis, MD 21401
  • 179 Green St, Annapolis, MD 21401
    179 Green St, Annapolis, MD 21401
    179 Green St, Annapolis, MD 21401
    /29

    $1,175,000

    • 2 Beds
    • 1.5 Baths
    • 1,656 Sq Ft

    179 Green St, Annapolis, MD 21401

    Experience the Essence of Annapolis Charm at 179 Green StreetNestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted

    David Yee Long & Foster Real Estate, Inc.

    179 Green St, Annapolis, MD 21401
  • 9 Shipwright St, Annapolis, MD 21401
    9 Shipwright St, Annapolis, MD 21401
    9 Shipwright St, Annapolis, MD 21401
    /46

    $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
  • 41 Cornhill St, Annapolis, MD 21401
    41 Cornhill St, Annapolis, MD 21401
    41 Cornhill St, Annapolis, MD 21401
    /37

    $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
  • 1 Shipwright Harbor, Annapolis, MD 21401
    1 Shipwright Harbor, Annapolis, MD 21401
    1 Shipwright Harbor, Annapolis, MD 21401
    /39

    $5,898,000

    • 3 Beds
    • 3.5 Baths
    • 3,108 Sq Ft

    1 Shipwright Harbor, Annapolis, MD 21401

    Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by renowned local architect as the culmination of an award winning career. The unsurpassed attention to architectural details, exquisitely curated finishes and breathtaking views of Spa Creek places this trophy home in a league of its own. Tucked away at the end of a quiet street in a premier

    Brad Kappel TTR Sotheby's International Realty

    1 Shipwright Harbor, Annapolis, MD 21401
Maryland Anne Arundel County Annapolis Downtown Annapolis

Real Estate & Homes for Sale in Downtown Annapolis, Annapolis

Why Live in Downtown Annapolis
Downtown Annapolis is a historic neighborhood radiating from Church Circle, featuring tree-shaded streets and a Colonial-era waterfront near the U.S. Naval Academy. The area is known for its picturesque properties, including Colonial Revival townhouses and detached homes from the 1800s, as well as newer condos that maintain early American stylings. Home prices vary significantly based on size, age, and location, with historic and waterfront properties commanding the highest prices. Residents enjoy several parks, such as Susan Campbell Park and Acton's Cove Waterfront Park, offering scenic views and shaded areas. Annapolis Waterworks Park has recently expanded its trail network, fostering a sense of community among outdoor enthusiasts. The neighborhood is bustling with things to do, including dining at local favorites like Galway Bay Irish Restaurant and Pub, and attending events like the annual Oyster Roast and Sock Burning. Despite the scarcity of parking, the area is highly walkable, with bus routes and water taxis providing convenient transportation options. Schools in the area are highly rated, with Wiley H. Bates Middle, Annapolis High, and St. Mary's School offering quality education. The crime rate is lower than the national average, contributing to the neighborhood's appeal.
Learn more about living in Downtown Annapolis

Frequently Asked Questions

Is Downtown Annapolis a good place to live?
Downtown Annapolis is a good place to live. Downtown Annapolis is considered very walkable and bikeable with some transit options. Downtown Annapolis is a suburban neighborhood. Downtown Annapolis has 5 parks for recreational activities. It is fairly sparse in population with 4.4 people per acre and a median age of 38. The average household income is $137,188 which is above the national average. College graduates make up 69.8% of residents. A majority of residents in Downtown Annapolis are renters, with 53.9% of residents renting and 46.1% of residents owning their home. A local real estate agent serving Downtown Annapolis can help you decide if this neighborhood is the right one for you. Learn more on our Downtown Annapolis neighborhood guide.
How much do you need to make to afford a house in Downtown Annapolis?
The median home price in Downtown Annapolis is $1,195,000. If you put a 20% down payment of $239,000 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $5,890 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $252K a year to afford the median home price in Downtown Annapolis. The average household income in Downtown Annapolis is $137K.
What are the best public schools in Downtown Annapolis?
The best public schools that serve Downtown Annapolis are:
What are the best private schools in Downtown Annapolis?
The best private schools that serve Downtown Annapolis are:
What are the most popular zip codes in Downtown Annapolis, Annapolis, MD?
The most popular zip codes in Downtown Annapolis, Annapolis, MD include 21401, 21403, 21409, 21032 and 21037.
What are the most popular neighborhoods near Downtown Annapolis, Annapolis, MD?
The most popular neighborhoods near Downtown Annapolis, Annapolis, MD are Forest Villa, Eastport, West Annapolis-Wardour, Tyler Heights-Primrose Acres and Victor Haven.

Home Trends in Downtown Annapolis, MD

On average, homes in Downtown Annapolis, Annapolis sell after 24 days on the market compared to the national average of 52 days. The median sale price for homes in Downtown Annapolis, Annapolis over the last 12 months is $1,138,000, up 22% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,138,000
Median Single Family Sale Price
$1,495,000
Median Townhouse Sale Price
$905,000
Median 2 Bedroom Sale Price
$937,500
Median 1 Bedroom Sale Price
$749,950
Average Price Per Sq Ft
$618
Number of Homes for Sale
11
Last 12 months Home Sales
58
Months of Supply
2.30
Median List Price
$1,195,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
22%
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