Leave a Message

By providing The Tower Team your contact information, you acknowledge and agree to our Privacy Policy and consent to receiving marketing communications, including through automated calls, texts, and emails, some of which may use artificial or prerecorded voices. This consent isn’t necessary for purchasing any products or services and you may opt out at any time. To opt out from texts, you can reply, ‘stop’ at any time. To opt out from emails, you can click on the unsubscribe link in the emails. Message and data rates may apply.

Thank you for your message. We will be in touch with you shortly.

Downtown Annapolis Single Family Homes For Sale

Discover the charm of Downtown Annapolis, MD with single family homes for sale that blend historic elegance and modern living. The Tower Team is here to help you find the perfect home in this vibrant, walkable waterfront community.

Single Family Homes For Sale in Downtown Annapolis

Price

Living Area

MLS® MDAA2099224

$789,000

820 Annapolis Rd, Gambrills, MD 21054

MLS® MDAA2122700

$445,000

953 Annapolis Rd, Gambrills, MD 21054

3 Beds 1 Bath 1,556 Sq.Ft.

MLS® MDAA2095698

$1,150,000

319 Epping Way, Annapolis, MD 21401

4 Beds 4 Baths 2,372 Sq.Ft.

MLS® MDAA2118098

$1,097,990

120 Stilly Way, Annapolis, MD 21403

6 Beds 6 Baths 4,934 Sq.Ft.

MLS® MDAA2103690

$875,000

2020 JOHN HANSON OVERLOOK, ANNAPOLIS, MD 21401

4 Beds 3 Baths 4,592 Sq.Ft.

MLS® MDAA2110674

$849,000

336 Severn Rd, Annapolis, MD 21401

2 Beds 3 Baths 1,708 Sq.Ft.

MLS® MDAA2116104

$7,000

5 WAVELAND FARMS RD, ANNAPOLIS, MD 21409

4 Beds 5 Baths 2,657 Sq.Ft.

MLS® MDAA2114138

$5,050

3730 THOMAS POINT RD, ANNAPOLIS, MD 21403

4 Beds 2 Baths 1,932 Sq.Ft.

MLS® MDAA2123674

$1,200

4 GILMER ST, ANNAPOLIS, MD 21401

1 Bed 1 Bath 1,536 Sq.Ft.

MLS® MDAA2123548

$2,800,000

778 BON HAVEN DRIVE, ANNAPOLIS, MD 21401

6 Beds 4 Baths 4,900 Sq.Ft.

MLS® MDAA2119266

$900,000

356 Broadview Ln, Annapolis, MD 21401

4 Beds 3 Baths 1,906 Sq.Ft.

MLS® MDAA2123444

$829,900

701 SONNE DRIVE, ANNAPOLIS, MD 21401

4 Beds 4 Baths 2,568 Sq.Ft.

MLS® MDAA2114986

$750,000

39 Windwhisper Ln, Annapolis, MD 21403

3 Beds 4 Baths 3,193 Sq.Ft.

MLS® MDAA2121446

$699,999

407 Merryman Rd, Annapolis, MD 21401

4 Beds 4 Baths 1,850 Sq.Ft.

MLS® MDAA2117604

$5,950,000

1864 MILVALE ROAD, ANNAPOLIS, MD 21409

4 Beds 7 Baths 7,684 Sq.Ft.

MLS® MDAA2115858

$3,850,000

2514 Lyon Dr, Annapolis, MD 21403

6 Beds 7 Baths 5,678 Sq.Ft.

MLS® MDAA2121364

$1,098,000

22 POTTERS LANE, ANNAPOLIS, MD 21403

4 Beds 4 Baths 3,652 Sq.Ft.

MLS® MDAA2122690

$875,000

1507 CIRCLE DRIVE, ANNAPOLIS, MD 21409

4 Beds 3 Baths 2,600 Sq.Ft.

MLS® MDAA2119980

$699,000

916 King James Landing Rd, Annapolis, MD 21403

4 Beds 4 Baths 2,986 Sq.Ft.

MLS® MDAA2119942

$524,500

124 CRANES CROOK LANE, ANNAPOLIS, MD 21401

2 Beds 4 Baths 2,370 Sq.Ft.

MLS® MDAA2122836

$4,975

18 STEELE AVE, ANNAPOLIS, MD 21401

3 Beds 3 Baths 2,130 Sq.Ft.

MLS® MDAA2109630

$3,495,000

9 Shipwright St, Annapolis, MD 21401

3 Beds 3 Baths 2,621 Sq.Ft.

MLS® MDAA2109848

$3,475,000

1576 Bay Head Rd, Annapolis, MD 21409

6 Beds 6 Baths 6,732 Sq.Ft.

MLS® MDAA2114190

$3,250,000

3015 Friends Rd, Annapolis, MD 21401

6 Beds 7 Baths 4,750 Sq.Ft.

MLS® MDAA2103810

$1,047,590

106 Stilly Way, Annapolis, MD 21403

4 Beds 5 Baths 4,594 Sq.Ft.

MLS® MDAA2123640

$475,000

114 2ND STREET, ANNAPOLIS, MD 21401

3 Beds 2 Baths 1,600 Sq.Ft.

MLS® MDAA2121748

$1,299,999

767 Bon Haven Dr, Annapolis, MD 21401

5 Beds 4 Baths 3,255 Sq.Ft.

MLS® MDAA2120506

$899,000

730 CRISFIELD WAY, ANNAPOLIS, MD 21401

5 Beds 5 Baths 3,586 Sq.Ft.

MLS® MDAA2120212

$729,900

7 Silopanna Rd, Annapolis, MD 21403

4 Beds 3 Baths 2,348 Sq.Ft.

MLS® MDAA2115252

$699,900

10 N Homeland Ave N, Annapolis, MD 21401

4 Beds 3 Baths 2,342 Sq.Ft.

MLS® MDAA2098628

$411,999

986 Yachtsman Way, Annapolis, MD 21403

2 Beds 2 Baths 1,174 Sq.Ft.

MLS® MDAA2105068

$3,100,000

856 St Edmonds Pl, Annapolis, MD 21401

5 Beds 5 Baths 6,412 Sq.Ft.

MLS® MDAA2120636

$1,630,000

3126 PORT WAY, ANNAPOLIS, MD 21403

4 Beds 5 Baths 3,200 Sq.Ft.

LISTINGS

For Sale

View more Single Family Homes For Sale in Downtown Annapolis

FAQs About Downtown Annapolis Single Family Homes For Salev

According to realtor.com, The median listing price of a property in Annapolis, Maryland, was $695K in July 2025, representing a 4% annual increase. $347 was the median listing price per square foot. $615K was the median price of a property sold.

Because of its prominent location and historic attractiveness, the Downtown market is competitive and has a limited inventory. Desired houses can be under contract in a matter of weeks, and homes frequently sell for close to asking price.

Historic District streets close to Main Street, City Dock, Church Circle, and the Arts District are all part of downtown Annapolis. Numerous residences are centuries old, combining Victorian, Federal, and Colonial styles with contemporary additions.

The Anne Arundel County Public School District includes downtown Annapolis. While older children may attend Annapolis High School or adjacent academies, families can choose from well-regarded schools like West Annapolis Elementary and neighbouring private choices.

Locals take pleasure in a thriving eating scene that includes informal favourites like Iron Rooster and Miss Shirley's Cafe, seafood eateries like Carrol's Creek Cafe and Cantler's Riverside Inn, and fine dining along Main Street and the waterfront. The Market House continues to be a major location for neighbourhood meals and events.

Work With Us

Our knowledge of neighborhoods, schools and all market offerings will provide valuable guidance to you about how and where to live in this diverse area where hundreds of waterways create many lifestyle choices. Contact us today!