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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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Get an instant cash offer
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What's worth fixing first
Find a seller's agent

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

258 listings

Homes Under $2M in Annapolis, MD

Homes Under $2M in Annapolis, MD

24 of 258 Listings

Homes Under $2M in Annapolis, MD

24 of 258 Listings

36Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

$879,000

3 bd · 3 ba · 2,700 sqft

3401 Saratoga Ave, Annapolis, MD

Melanie A Graw · Coldwell Banker Realty

$1,295,000

4 bd · 3 ba · 2,720 sqft

1546 Shipsview Rd, Annapolis, MD

Reid Buckley · Long & Foster Real Estate, Inc.

$974,990

4 bd · 3 ba · 3,846 sqft

3268 Kitty Duvall Dr, Annapolis, MD

Tanya M Trapani · Blackwell Real Estate, LLC

$695,000

3 bd · 3 ba · 2,113 sqft

940 Astern Way #508, Annapolis, MD

Marjorie S Halem · Compass

$1,675,000

5 bd · 3 ba · 2,888 sqft

250 Prince George St, Annapolis, MD

Pamela A Tierney · Coldwell Banker Realty

$925,000

4 bd · 4 ba · 3,004 sqft

1422 Bay Head Rd, Annapolis, MD

Katie Neighoff · RE/MAX United Real Estate

$850,000

2 bd · 2 ba · 1,135 sqft

141 West St #204, Annapolis, MD

Parker D Jones · Engel & Volkers Annapolis

$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

$335,000

3 bd · 3 ba · 1,694 sqft

40-B Ironstone Ct #B, Annapolis, MD

Cynthia Lisa · RE/MAX One

Price Reduced29Active

$329,000

2 bd · 2 ba · 1,070 sqft

2026 Gov Thomas Bladen Way #204, Annapolis, MD

Justin Ryan Pokrywka · Taylor Properties

$539,000

3 bd · 4 ba · 2,280 sqft

237 Chatham Ln, Annapolis, MD

Jean Berkinshaw Dixon · Coldwell Banker Realty

$699,000

2 bd · 2 ba · 1,723 sqft

78 Old Mill Bottom Rd N #311, Annapolis, MD

Kelly A Jackson · Samson Properties

$775,000

2 bd · 2 ba · 1,259 sqft

7026 Channel Village Ct #T2, Annapolis, MD

Bradley R Kappel · TTR Sotheby's International Realty

$269,900

2 bd · 2 ba · 1,082 sqft

300 Hilltop Ln #300E, Annapolis, MD

Elizabeth R Penttinen · Coldwell Banker Realty

Price Reduced23Active

$424,800

2 bd · 2 ba · 1,210 sqft

78 Old Mill Bottom Rd N #209, Annapolis, MD

Alexandra I Burrell-Hodges · Cottage Street Realty LLC

$175,000

1 bd · 2 ba · 1,100 sqft

2004 Quay Village Ct #T1, Annapolis, MD

Larry E Cooper · Alex Cooper Auctioneers, Inc.

Price Reduced73Active

$399,500

3 bd · 4 ba · 1,672 sqft

311 Sloping Woods Ct, Annapolis, MD

Catherine Cusack · Coldwell Banker Realty

$520,000

4 bd · 3 ba · 1,668 sqft

1365 Moyer Rd, Annapolis, MD

Ryan Michael Dacy · Cummings & Co. Realtors

$589,900

3 bd · 1 ba · 1,492 sqft

223 Dewey Dr, Annapolis, MD

Stacey R White · Coldwell Banker Realty

$419,900

4 bd · 2 ba · 1,872 sqft

1660 Secretariat Dr, Annapolis, MD

Jim Rambo · ABR

$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

1 2 3…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: 2026-10-01 23:07:37 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.