165 Woodside Trail

Off Market

165 Woodside Trail

Parole MD 21401

2720 sq. ft.

13650 sq. ft.

Single-Family

Last sold for $575,000

Robert Carter, last sold this property on 22 August 2025 after 37 days on market.

Overview

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.

Features

4 bedrooms

2 bathrooms

10 carspaces

2720 sq. ft. floor area

13650 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Parole over the last 12 months, the estimated median property value of 165 Woodside Trail is $900k.

Median value

$900k

Estimated value range

$260k - $11.25m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Parole. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 165 Woodside Trail

2025

Sold

$575,000

22 Aug 2025 by Robert Carter, of DOUGLAS REALTY, LLC

Happy sellers in Parole

96%

96% of sellers in Parole reported that their sale price either exceeded or met their price expectations.

Parole stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 14 reviews in Parole over the last 12 months.

Local market activity for 4 bedroom single-family properties in Parole

In the last 12 months, 89 four-bedroom single-family properties similar to 165 Woodside Trail, have been sold.

This represents a 26% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

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