Downtown Annapolis Homes

/40
$1,699,999 Under Contract
- 4 Beds
- 2.5 Baths
- 2,550 Sq Ft
146 Prince George St, Annapolis, MD 21401

"Price Improvement..." Own a Piece of Annapolis History – Don’t miss this rare opportunity to own an exquisitely restored historic home in the heart of downtown Annapolis. Welcome to The Quarter Deck on Prince George—a 4-bedroom, 2.5-bathroom retreat that blends timeless charm with modern convenience, all while boasting a proven short-term rental history. Financials are available upon request.

Rob Carter Douglas Realty, LLC

146 Prince George St, Annapolis, MD 21401
/5

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
/22
$259,900 Sold Jul 19, 2025
- 840 Sq Ft
- $309/SF
- 110 Days On Market
- 2 Beds
- 1 Bath
- Built 1940
38 Pleasant St, Annapolis, MD 21401

Welcome to 38 Pleasant St! This renovated 2-bedroom, 1-bath townhome is located in downtown Annapolis and could be the perfect starter home or investment property. Renovations in 2021 included a new kitchen with stainless steel GE appliances, new flooring, HVAC, and a hot water heater. The main level features a living room, dining room, and kitchen that leads out to a fenced-in yard. The upper

Santiago Navarro-monzo Coldwell Banker Realty

38 Pleasant St, Annapolis, MD 21401

/30
Est $1,458,833 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

/51
$1,525,000
- 4 Beds
- 4 Baths
- 2,732 Sq Ft
57 Richards Ln, Annapolis, MD 21401

This stunning home in the coveted community of Acton’s Landing, combines all the amenities of modern living with the beauty, charm and architecture of historic Annapolis. A short stroll to Main Street lets you explore the restaurants, galleries, cafes, shops, and historic sights before returning to what feels like your own private oasis! This rarely available end-unit townhome was the original

Stephanie Snyder Long & Foster Real Estate, Inc.

57 Richards Ln, Annapolis, MD 21401
/31
$4,600 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
/69
$1,151,000 Sold Jul 17, 2025
- 1,109 Sq Ft
- $1038/SF
- 9 Days On Market
- 2 Beds
- 2 Baths
- Built 1930
16 Southgate Ave, Annapolis, MD 21401

Where to Begin?Where timeless style meets smart functionality, this stunning one-level gem in Murray Hill is more than just a home. Bathed in natural light with soaring vaulted ceilings, this meticulously renovated architectural treasure offers a surprising sense of openness and calm. Every inch has been thoughtfully designed to create a private, peaceful oasis just steps from the heart of

Malina Koerschner Coldwell Banker Realty

16 Southgate Ave, Annapolis, MD 21401

/56
Est $1,133,518 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

/29
$775,000
- 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
/11
$1,895 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- House for Rent
5 Murray Ave, Annapolis, MD 21401

AVAILABLE August 1 - Rare opportunity in Murry Hill - First Floor Studio Apartment with full bath, Kitchen and washer dryer. Million dollar setting house for a fraction of the cost Min gross income of $74,000 and credit score of 640 required. TEXT, DO NOT CALL, TEXT Tom . REFFER TO MURRAY HILL UNIT B WHEN INQUIRING. STREET PARKING

5 Murray Ave, Annapolis, MD 21401
/44
$950,000 Sold Jul 15, 2025
- 1,527 Sq Ft
- $622/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
173 Prince George St, Annapolis, MD 21401

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 plan make this home feel light and breezy and create great flow throughout. Glass doors from the great room open to a private brick patio and primary bedrooms has a deck with retractable awning. Spacious top level suite has

Alex Tower Sears TTR Sotheby's International Realty

173 Prince George St, Annapolis, MD 21401

/40
Est $997,581 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,584 Sq Ft
66 Franklin St Unit 304, Annapolis, MD 21401

66 Franklin St Unit 304, 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
/43
$2,650 per month
- 1-3 Beds
- 1 Bath
- 800 Sq Ft
- Condo for Rent
26 South St Unit 3, Annapolis, MD 21401

Welcome to 26 South Street - a fully renovated boutique building steps from the water and downtown Annapolis. With 3 thoughtfully designed and furnished units, the building offers a turnkey home base in the heart of the city on a quiet waterfront street. We are flexible on lease terms and dates for great tenants.

26 South St Unit 3, Annapolis, MD 21401
/21
$215,000 Sold Jul 15, 2025
- 1,037 Sq Ft
- $207/SF
- 31 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1975
63 Town Pines Ct, Annapolis, MD 21401

Welcome to the heart of downtown Annapolis, where city living meets historic charm! This 3-bedroom, 1 Full and 1 Half-bathroom, townhome offers an incredible opportunity to be just 2 blocks away from the Capitol building, shopping, restaurants, and the picturesque waterfront filled with boats. Convenience is key with parking included, allowing you to explore the vibrant downtown area with ease.

Martin Tippet ExecuHome Realty

63 Town Pines Ct, Annapolis, MD 21401

/106
Est $2,277,869 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

/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
/32
$1,125,000 Sold Jul 07, 2025
- 2,322 Sq Ft
- $484/SF
- 34 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1832
160 Green St, Annapolis, MD 21401

Step into a piece of Annapolis history with the Philip Clayton House, a cherished landmark dating back to 1834. Perfectly situated within walking distance to the City Dock, U.S. Naval Academy, and the vibrant shops and restaurants of Downtown Annapolis, this residence blends timeless character with everyday convenience. Over nearly two centuries, the home has undergone thoughtful renovations and

Lucie Dulin Compass

160 Green St, Annapolis, MD 21401

/32
Est $652,660 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

/49
$1,475,000
- 4 Beds
- 3 Baths
- 2,649 Sq Ft
165 King George St, Annapolis, MD 21401

Back on the market with a DRAMATIC price improvement!! Welcome to your truly turnkey 3-unit investment property in the HEART of Annapolis!! All 3 units come FULLY furnished, down to the spoons and forks!! Literally STEPS away from the Naval Academy main gate and downtown Annapolis!! Unit 1 is a 1 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. You will

Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

165 King George St, Annapolis, MD 21401
/27
$3,517,500 Sold Jun 30, 2025
- 3,119 Sq Ft
- $1128/SF
- 0 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1930
11 Southgate Ave, Annapolis, MD 21401

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 Annapolis. Perfect seamless renovation, excellent layout, timeless, gorgeous designed baths and kitchen.Some beautiful views, excellent outdoor entertaining space, fully fenced yard and even an impossible to find detached garage. Only a

Alex Tower Sears TTR Sotheby's International Realty

11 Southgate Ave, Annapolis, MD 21401

/30
Est $705,453 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

/49
$1,475,000
- Studio
- 2,649 Sq Ft
165 King George St, Annapolis, MD 21401

Back on the market with a DRAMATIC price improvement!! Welcome to your truly turnkey 3-unit investment property in the HEART of Annapolis!! All 3 units come FULLY furnished, down to the spoons and forks!! Literally STEPS away from the Naval Academy main gate and downtown Annapolis!! Unit 1 is a 1 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. You will

Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

165 King George St, Annapolis, MD 21401
/32
$699,000 Sold Jun 30, 2025
- 1,032 Sq Ft
- $677/SF
- 3 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1918
104 South St, Annapolis, MD 21401

Ideally located in the heart of the Historic Annapolis, this beautifully maintained 2-bedroom, 1.5-bath home is just a short walk from Church Circle and one block from a waterfront park—perfect for launching your paddleboard or catching a water taxi for a quick ride to Eastport. With Spa Creek just steps away and Main Street, West Street restaurants, the City Dock, Naval Academy, and Murray Hill

Jenna Smith Redfin Corp

104 South St, Annapolis, MD 21401

/36
Est $1,389,595 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

/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
/59
$2,150,000 Sold Jun 27, 2025
- 2,833 Sq Ft
- $759/SF
- 0 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1936
19 Thompson St, Annapolis, MD 21401

This absolutely stunning 4-bedroom, 2.5-bath home in the heart of Murray Hill has just undergone a full-scale renovation by a top-tier local architect, designer, and builder—resulting in a true magazine-worthy home. Thoughtfully reimagined to blend timeless style with modern functionality, the home features a chef’s kitchen with custom cabinetry, marble countertops, built-in bench seating, and

Elizabeth Dooner Coldwell Banker Realty

19 Thompson St, Annapolis, MD 21401

/6
Est $1,833,766 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,762 Sq Ft
92 Duke of Gloucester St, Annapolis, MD 21401

92 Duke of Gloucester St, Annapolis, MD 21401

/37
$2,300,000
- 4 Beds
- 2.5 Baths
- 4,404 Sq Ft
41 Cornhill St, Annapolis, MD 21401

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 burning Fireplace; a Two Room Parlor, also with a

Lorain Shore Expert Realty, LLC.

41 Cornhill St, Annapolis, MD 21401
/52
$3,100,000 Sold Jun 27, 2025
- 3,591 Sq Ft
- $863/SF
- 6 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1890
21 Southgate Ave, Annapolis, MD 21401

Sited on a prominent double lot in the heart of Annapolis' Murray Hill neighborhood, 21 Southgate Avenue is a masterfully reimagined home. Originally built by the Southgate family in the late 1800s, this one-of-a-kind estate blends formal sophistication with effortless Annapolis charm. Honoring its architectural heritage while delivering the luxuries of today, the home was crafted by Reverend

Elizabeth Dooner Coldwell Banker Realty

21 Southgate Ave, Annapolis, MD 21401

/65
Est $1,884,335 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

/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
/48
$1,460,000 Sold Jun 11, 2025
- 3,104 Sq Ft
- $470/SF
- 30 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1910
88 Market St, Annapolis, MD 21401

OPEN HOUSE SCHEDULED FOR SUNDAY, MAY 18th HAS BEEN CANCELLED. UNDER CONTRACT!!ATTENTION WOULD-BE ANNAPOLITANS !!! RARE OPPORTUNITY TO OWN and LUXURIOUSLY ABIDE IN RESTORED HISTORIC DISTRICT HOME on lower Market Street punctuated by Spa Creek’s waterfront! Stroll along storied brick sidewalks to downtown City Dock’s bustling harbor of boutiques, bistros, boating, and USNA activity. Grab a water

Donna Hagen Coldwell Banker Realty

88 Market St, Annapolis, MD 21401

/39
Est $775,251 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

/50
$12,750,000 Pending
- 4 Beds
- 7 Baths
- 5,069 Sq Ft
17 Revell St, Annapolis, MD 21401

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 including just steps to restaurants and bars, annual parades/events, Annapolis Yacht club, St. Mary's school, and water taxi pick up location. Additionally, the property boasts the only gated waterfront residence in Historic Annapolis.

Brad Kappel TTR Sotheby's International Realty

17 Revell St, Annapolis, MD 21401
/84
$1,725,000 Sold Jun 03, 2025
- 3,160 Sq Ft
- $546/SF
- 8 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1905
33 Southgate Ave, Annapolis, MD 21401

Charming Murray Hill Gem in the Heart of Annapolis!Discover this classic Murray Hill residence, perfectly situated on sought-after Southgate Avenue. This beautifully maintained home is move-in ready and offers timeless charm with modern updates.Step onto the inviting front porch and take in the tree-lined street before entering a home filled with character—hardwood floors, nine-foot ceilings,

Georgie Berkinshaw Coldwell Banker Realty

33 Southgate Ave, Annapolis, MD 21401

/46
Est $1,247,412 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 990 Sq Ft
10 Cheston Ave, Annapolis, MD 21401

10 Cheston Ave, Annapolis, MD 21401

/49
$1,500,000 Pending
- 3 Beds
- 3.5 Baths
- 1,806 Sq Ft
60 Cornhill St, Annapolis, MD 21401

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 lovely spaces on all three levels. Open kitchen has great space to entertain and dine and exceptional storage. Home was redesigned and renovated to maximize comfortable, beautiful and convenient downtown living. Home features

Alex Tower Sears TTR Sotheby's International Realty

60 Cornhill St, Annapolis, MD 21401
/32
$700,000 Sold May 30, 2025
- 988 Sq Ft
- $709/SF
- 9 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1900
24 Fleet St, Annapolis, MD 21401

*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 reserves the right to accept an offer before deadline*Welcome to 24 Fleet St—a beautifully maintained 2-bedroom, 1.5-bath row home nestled in the heart of historic downtown Annapolis. This classic home blends timeless character

Shane Hall Compass

24 Fleet St, Annapolis, MD 21401

/75
Est $977,998 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

Showing Results 1 - 40, Page 1 of 18

Maryland Annapolis Downtown Annapolis

Learn more about living in Downtown Annapolis

Home Trends in Downtown Annapolis, MD

On average, homes in Downtown Annapolis, Annapolis sell after 18 days on the market compared to the national average of 51 days. The median sale price for homes in Downtown Annapolis, Annapolis over the last 12 months is $1,002,750, up 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,002,750

Median Single Family Sale Price

$1,495,000

Median Townhouse Sale Price

$945,000

Median 2 Bedroom Sale Price

$855,000

Median 1 Bedroom Sale Price

$762,450

Average Price Per Sq Ft

$572

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.80

Median List Price

$1,163,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

18%

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