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The buying timeline

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How much can I afford?
Get pre-approved

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3 beds New construction

5 Bedroom Homes in Annapolis, MD — Page 2

34 listings

5 Bedroom Homes in Annapolis, MD

5 Bedroom Homes in Annapolis, MD

10 of 34 Listings

5 Bedroom Homes in Annapolis, MD

10 of 34 Listings

Price Reduced66Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

$4,500,000

5 bd · 4 ba · 4,107 sqft

217 Lockwood Ct, Annapolis, MD

sandra K. Libby · Long & Foster Real Estate, Inc.

Price Reduced59Active

$1,549,000

5 bd · 2 ba · 2,100 sqft

202 Wardour Dr, Annapolis, MD

David Orso · Berkshire Hathaway HomeServices PenFed Realty

Price Reduced25Active

$960,000

5 bd · 5 ba · 9,960 sqft

1254 Washington Dr, Annapolis, MD

Nadia Aminov · Long & Foster Real Estate, Inc.

$12,500,000

5 bd · 7 ba · 5,993 sqft

5 Franklin St, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

Price Reduced51Active

$2,295,000

5 bd · 4 ba · 3,178 sqft

83 Market St, Annapolis, MD

Elizabeth C Dooner · Coldwell Banker Realty

Price Reduced53Active

$9,998,000

5 bd · 6 ba · 6,061 sqft

8 Spa View Cir, Annapolis, MD

Georgeann A Berkinshaw · Coldwell Banker Realty

$8,750,000

5 bd · 7 ba · 7,105 sqft

2035 Maidstone Farm Rd, Annapolis, MD

Georgeann A Berkinshaw · Coldwell Banker Realty

$669,000

5 bd · 2 ba · 2,522 sqft

1200 Bay Ave, Annapolis, MD

Antoine B Johnson · Powerhouse Realty, LLC.

Price Reduced97Active

$1,049,000

5 bd · 4 ba · 3,240 sqft

1812 Shore Dr, Annapolis, MD

Day W Weitzman · Coldwell Banker Realty

Price Reduced55Active

$999,999

5 bd · 4 ba · 3,255 sqft

767 Bon Haven Dr, Annapolis, MD

Sean O'Connor · Coldwell Banker Realty

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-10-05 19:19:18 UTC

Annapolis, MD community profile

Population: 42,070
Median income: $97,319
Housing units: 18,886
People per sq. mi.: 704.7
Area: 59.7 sq. mi.

Source: HJN community data

Annapolis housing market

September 2026 · This period is still settling

Selling at 99.5% of asking price

Buyers here are paying below asking. MLS · 103 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $744,000$530,000–$1,031,875 typical range
Price per sq. ft.: $355
Sales: 48
Paid in cash: 31.3%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $699,990
Homes for sale: 295
Median days on market: 17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 24.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 3, 2026

Median home size: 1,920 sq. ft.