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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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What's worth fixing first
Find a seller's agent

Luxury Homes in Annapolis, MD

86 listings

Luxury Homes in Annapolis, MD

Luxury Homes in Annapolis, MD

24 of 86 Listings

Luxury Homes in Annapolis, MD

24 of 86 Listings

77Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

$1,650,000

4 bd · 3 ba · 2,890 sqft

1739 Vineyard Trl, Annapolis, MD

Christine L Bishop · Berkshire Hathaway HomeServices PenFed Realty

$1,200,000

3 bd · 3 ba · 2,016 sqft

9 Hull Ave, Annapolis, MD

Stephen L Asper · Coldwell Banker Realty

$1,595,000

4 bd · 5 ba · 3,020 sqft

123 Chesapeake Ave, Annapolis, MD

Sarah Greenlee Morse · TTR Sotheby's International Realty

$2,995,000

3 bd · 4 ba · 4,223 sqft

1800 River Watch Ln, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

$1,700,000

4 bd · 3 ba · 3,142 sqft

1323 Magnolia Ave, Annapolis, MD

Brandi Bradshaw · Keller Williams Select Realtors of Annapolis

$1,085,000

4 bd · 6 ba · 5,854 sqft

2700 Windswept Ln, Annapolis, MD

Betty W Jans · Berkshire Hathaway HomeServices PenFed Realty

$1,295,000

4 bd · 3 ba · 2,720 sqft

1546 Shipsview Rd, Annapolis, MD

Reid Buckley · Long & Foster Real Estate, Inc.

$2,250,000

3 bd · 3 ba · 0 sqft

102 Melvin Ave, Annapolis, MD

Kevin C Cooke · Coldwell Banker Realty

$2,650,000

5 bd · 5 ba · 4,435 sqft

8 Brooke Ave, Annapolis, MD

Elizabeth Jean DuLaney · EXP Realty, LLC

$1,675,000

5 bd · 3 ba · 2,888 sqft

250 Prince George St, Annapolis, MD

Pamela A Tierney · Coldwell Banker Realty

$1,750,000

4 bd · 4 ba · 2,718 sqft

102 Duke Of Gloucester St, Annapolis, MD

Scott Jonathan Wallace Jr. · Coldwell Banker Realty

$1,300,000

5 bd · 4 ba · 2,550 sqft

135 Conduit St, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

Price Reduced40Active

$1,900,000

4 bd · 4 ba · 4,099 sqft

400 Jefferson St, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

$9,500,000

6 bd · 10 ba · 10,745 sqft

3285 Harness Creek Rd, Annapolis, MD

Reid Buckley · Long & Foster Real Estate, Inc.

$1,395,000

4 bd · 5 ba · 2,853 sqft

1030 Boucher Ave, Annapolis, MD

Richard M. Curtis · Curtis Real Estate Company

$1,250,000

4 bd · 4 ba · 2,391 sqft

700 Miller Rd, Annapolis, MD

Alexandra I Burrell-Hodges · Cottage Street Realty LLC

$1,875,000

4 bd · 5 ba · 3,900 sqft

820 Bay Ridge Ave, Annapolis, MD

Wendy T Oliver · Coldwell Banker Realty

$1,285,000

4 bd · 3 ba · 3,182 sqft

1610 Ridout Rd, Annapolis, MD

Alexandra Tower Sears · TTR Sotheby's International Realty

$2,795,000

3 bd · 3 ba · 2,286 sqft

113 Bay Dr, Annapolis, MD

Elizabeth Atwood · Krauss Real Property Brokerage

Price Reduced95Active

$1,449,000

5 bd · 5 ba · 5,639 sqft

1603 Waters Ridge Ct, Annapolis, MD

Christina J Palmer · Keller Williams Flagship

$1,390,000

3 bd · 5 ba · 3,100 sqft

113 Sellew Rd, Annapolis, MD

Alison Wisnom · Coldwell Banker Realty

$1,350,000

6 bd · 6 ba · 2,922 sqft

3 Rusty Red Dr, Annapolis, MD

Alison Wisnom · Coldwell Banker Realty

$1,105,000

5 bd · 5 ba · 4,484 sqft

507 Sunwood Ln, Annapolis, MD

Ross Tobin · RE/MAX Aspire

Price Reduced34Active

$1,195,000

2 bd · 2 ba · 1,744 sqft

2915 South Ct, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

1 2…4

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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.

© 2026 Realty.com. All rights reserved.PrivacyTermsCalifornia Privacy RightsAccessibilityLicensing

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: 2026-10-02 14:44:13 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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 81 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 10, 2026

Median sale price: $689,500$493,750–$1,031,875 typical range
Price per sq. ft.: $376
Sales: 40
Paid in cash: 30.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $699,990
Homes for sale: 295
Median days on market: 9 days

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

Year-over-year: 14.9%

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.