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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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What's my home worth?
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Get an instant cash offer
Buy before you sell

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Pricing your home
What's worth fixing first
Find a seller's agent

3 beds New construction

5 Bedroom Homes in Annapolis, MD

10 listings

5 Bedroom Homes in Annapolis, MD

5 Bedroom Homes in Annapolis, MD

10 Listings

5 Bedroom Homes in Annapolis, MD

10 Listings

49Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

$3,997,000

5 bd · 7 ba · 6,234 sqft

14 E Lake Dr, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

$3,000,000

5 bd · 2 ba · 5,522 sqft

1979 Baltimore Annapolis Blvd, Annapolis, MD

Alison Wisnom · Coldwell Banker Realty

$2,999,900

5 bd · 5 ba · 5,260 sqft

1486 Downham Market, Annapolis, MD

Wendy T Oliver · Coldwell Banker Realty

$4,600,000

5 bd · 4 ba · 5,095 sqft

140 Spa Dr, Annapolis, MD

Biana J Arentz · Coldwell Banker Realty

Price Reduced46Active

$2,495,000

5 bd · 5 ba · 5,082 sqft

3733 Thomas Point Rd, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

Price Reduced66Active

$4,500,000

5 bd · 4 ba · 4,107 sqft

217 Lockwood Ct, Annapolis, MD

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

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 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

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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.