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Start here

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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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Find a seller's agent

Homes Under $2M in Annapolis, MD — Page 3

263 listings

Homes Under $2M in Annapolis, MD

Homes Under $2M in Annapolis, MD

24 of 263 Listings

Homes Under $2M in Annapolis, MD

24 of 263 Listings

43Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

$750,000

4 bd · 3 ba · 2,202 sqft

580 Pinedale Dr, Annapolis, MD

William Haversack · Cummings & Co. Realtors

$285,000

3 bd · 2 ba · 1,447 sqft

142 Georgetown Rd #9, Annapolis, MD

Arianit Musliu · Redfin Corp

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

$475,000

2 bd · 2 ba · 1,588 sqft

940 Astern Way #112, Annapolis, MD

David L Wright · Coldwell Banker Realty

$379,900

2 bd · 2 ba · 1,103 sqft

1133 Lake Heron Dr #2B, Annapolis, MD

Caroline Leigh Nowell · Cummings & Co. Realtors

$1,395,000

4 bd · 5 ba · 2,853 sqft

1030 Boucher Ave, Annapolis, MD

Richard M. Curtis · Curtis Real Estate Company

$675,000

3 bd · 2 ba · 1,954 sqft

953 Mastline Dr, Annapolis, MD

Joe L Smith III · Next Step Realty, LLC.

$549,000

4 bd · 4 ba · 2,024 sqft

218 Wintergull Ln, Annapolis, MD

Jennifer A Yeatts · Berkshire Hathaway HomeServices PenFed Realty

Price Reduced32Active

$355,000

3 bd · 2 ba · 1,328 sqft

2161 Scotts Crossing Ct #302, Annapolis, MD

Sheena Saydam · Keller Williams Capital Properties

Price Reduced37Active

$629,900

4 bd · 3 ba · 2,156 sqft

1430 Catlyn Pl, Annapolis, MD

Donna L Reichert · Keller Williams Flagship

$725,000

3 bd · 2 ba · 1,634 sqft

2567 Forest Knl St, Annapolis, MD

Diana Pham · EXP Realty, LLC

$750,000

3 bd · 3 ba · 1,316 sqft

906 Jackson St, Annapolis, MD

Danielle D Cook · EXP Realty, LLC

$950,000

5 bd · 4 ba · 3,081 sqft

2175 Glencrest Cir, Annapolis, MD

Robert J Lucido · Keller Williams Lucido Agency

$879,990

4 bd · 3 ba · 2,411 sqft

1049 Sun Valley Dr, Annapolis, MD

Julie Dinko · Douglas Realty LLC

$825,000

4 bd · 4 ba · 2,533 sqft

2691 Claibourne Rd, Annapolis, MD

Danielle Franz · EXP Realty, LLC

Price Reduced47Active

$309,900

3 bd · 4 ba · 1,960 sqft

57 Gentry Ct, Annapolis, MD

Mary C Gatton · Redfin Corp

Price Reduced35Active

$659,900

3 bd · 4 ba · 2,980 sqft

525 Deep Creek Vw, Annapolis, MD

Jen Denney · EXP Realty, LLC

$610,000

4 bd · 3 ba · 1,906 sqft

301 Cedar Ln, Annapolis, MD

Roxanne Newton Marsh · ExecuHome Realty

$1,250,000

4 bd · 4 ba · 2,391 sqft

700 Miller Rd, Annapolis, MD

Alexandra I Burrell-Hodges · Cottage Street Realty LLC

Price Reduced32Active

$329,900

2 bd · 2 ba · 1,282 sqft

631 Admiral Dr #304, Annapolis, MD

Robert James Shaw · Taylor Properties

$1,875,000

4 bd · 5 ba · 3,900 sqft

820 Bay Ridge Ave, Annapolis, MD

Wendy T Oliver · Coldwell Banker Realty

$730,000

2 bd · 2 ba · 966 sqft

141 West St #308, Annapolis, MD

Elizabeth C Dooner · Coldwell Banker Realty

$619,000

4 bd · 4 ba · 2,550 sqft

138 Cranes Crook Ln, Annapolis, MD

Yael E Beckman · 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

1 2 3 4…11

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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 14:36:42 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.