SoldAug 22, 2025

Listed by Robert Carter and ERIN CARTER

Bought with Virginia Dauses from Coldwell Banker Waterman Realty

Source: Bright MLS #MDAA2120210

165 Woodside Trail, Parole, MD, 21401

$575,000

4
2
10
2720 sq. ft.
13650 sq. ft.

SingleFam

10 days on the market

Sold: Aug 22, 2025

What's around 165 Woodside Trail

About this property

Welcome to 165 Woodside Trail, Annapolis, MD – a charming 4-bedroom, 2-bathroom home nestled in the sought-after water-privileged community of Cape St. John. This inviting property offers the ideal blend of comfort, convenience, and coastal lifestyle. Residents enjoy access to a private community beach, boat ramp, and water access to the scenic South River — perfect for kayaking, paddleboarding, or setting out on the boat. Thoughtfully updated, the home features a new trex deck, new windows, doors, siding, and gutters—all replaced in 2014—providing peace of mind and enhanced curb appeal. Inside, you'll find a bright and functional layout with spacious bedrooms, two full bathrooms, and a welcoming living area. The kitchen boasts a brand-new stove and refrigerator (2024), making it ready for your culinary creations. The unfinished lower level offers endless possibilities—create a home gym, workshop, media room, or additional living space tailored to your needs. Whether you're looking for a year-round residence or a weekend retreat near the water, this home offers an incredible opportunity to live the Annapolis lifestyle. Don't miss your chance to own in this desirable community just minutes from downtown, shopping and dining.

Looking for more information on 165 Woodside Trail?

Explore comparables, sales history and growth for this property.
Learn more

Contact

Similar properties sold nearby

SoldJun 24, 2026
$1,353,000
304 Glen Ave
Annapolis MD 21401
4
4
2
Single-Family
Listing courtesy of REMAX Executive | Severna Park and May Realty
SoldJun 15, 2026
$1,400,000
103 McKendree Avenue
Annapolis MD 21401
4
4
2
Single-Family
Listing courtesy of Coldwell Banker Realty and TTR Sotheby's International Realty
SoldJun 15, 2026
$885,075
527 Post Oak Road
Parole MD 21401
4
3
4
Single-Family
Listing courtesy of Coldwell Banker Realty and TTR Sotheby's International Realty

Other properties sold by DOUGLAS REALTY, LLC

SoldJun 26, 2026
$270,000
UNIT 39C/720 Rusty Anchor Rd
Ocean City MD 21842
1
2
Condo
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC and DOUGLAS REALTY, LLC
SoldJun 26, 2026
$641,000
7887 Poplar Grove Road
Severn MD 21144
3
3
9
Single-Family
Listing courtesy of DOUGLAS REALTY, LLC and Samson Properties
SoldJun 26, 2026
$380,000
402 Bayside Drive
Dundalk MD 21222
4
2
Single-Family
Listing courtesy of DOUGLAS REALTY, LLC and Unrepresented Buyer Office

Browse properties sold in nearby areas

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 DOUGLAS REALTY, LLC 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. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

© 2026 RateMyAgent