- 4 beds
- 2 baths
- 1,360 sqft
- 13,650 sqft lot
- $419 per sqft
- 1980 build
*Professional Photos will be online on 7/17, stay tuned* 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.
Last checked:
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Last updated Jul 15, 2025
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MLS# MDAA2120210 —
Upcoming Open Houses
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Saturday, 7/19
12pm-2pm -
Sunday, 7/20
12pm-2pm
The Building
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Year Built:1980
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Year Built Source:Assessor
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New Construction:No
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Construction Materials:Vinyl Siding
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Structure Type:Detached
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Architectural Style:Ranch/Rambler
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Levels:2
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Accessibility Features:Level Entry - Main, Roll-in Shower, 2+ Access Exits, 32, Grab Bars Mod, Mobility Improvements, Ramp - Main Level, Roll-under Vanity
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Foundation Details:Concrete Perimeter
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Basement:Yes
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Basement Type:Interior Access, Outside Entrance, Poured Concrete, Rear Entrance, Sump Pump, Unfinished, Walkout Stairs
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Total SqFt Source:Assessor
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Total Below Grade SqFt:1360
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Total Below Grade SqFt Source:Assessor
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Above Grade Finished Area Units:Square Feet
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Above Grade Finished SqFt:1360
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Above Grade Finished SqFt Source:Assessor
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Below Grade Finished Area Units:Square Feet
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Below Grade Unfinished Area Units:Square Feet
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Below Grade Finished SqFt Source:Assessor
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Below Grade Unfinished SqFt:1360
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Below Grade Unfinished SqFt Source:Assessor
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Tax Total Finished SqFt:1360
Interior
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Fireplace:Yes
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Fireplaces:1
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Fireplace Features:Brick, Wood
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Living Area SqFt Source:Assessor
Room Dimensions
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Total SqFt:2720
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Living Area SqFt:1,360 Sqft
Financial & Terms
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Sale Type:Standard
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Possession:Settlement
Location
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Directions:Use GPS
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Latitude:38.95837000
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Longitude:-76.56101000
The Property
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Property Type:Residential
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Property Condition:Excellent
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Lot Size Units:Square Feet
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Lot Size Acres:0.31
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Lot Size Source:Assessor
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Lot SqFt:13,650 Sqft
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Zoning:R2
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In City Limits:No
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Other Structures:Above Grade, Below Grade
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Waterview:No
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Waterfront:No
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Water Oriented:Yes
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Water Access:Yes
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Water Access Features:Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, Waterski/Wakeboard
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Water Body Name:South River
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Water Body Type:River
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Navigable Water:Yes
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Tidal Water:No
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Land Use Code:R
Listing Agent
- Contact info:
- Agent phone:
- (443) 677-3058
- Office phone:
- (410) 255-3690
Taxes
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Tax ID Number:020215404016805
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Tax Year:2024
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Tax Lot:166
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Tax Annual Amount:$5,220
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Tax Assessed Value:$452,867
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Year Assessed:2025
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County Tax:4840.00
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Total Taxes Payment Frequency:Annually
Beds
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Bedrooms:4
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Bedrooms Main Level:4
Baths
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Total Baths:2
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Full Baths:2
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Main Level Baths:2.00
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Main Level Full Baths:2
Heating & Cooling
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Cooling Type:Ceiling Fan(s), Central A/C
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Central Air:Yes
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Cooling Fuel:Electric
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Heating:Yes
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Heating Type:Heat Pump - Oil BackUp, Central
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Heating Fuel:Electric, Oil
Utilities
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Sewer/Septic:Public Sewer
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Hot Water:Electric
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Water Source:Public
Appliances
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Appliances:Dishwasher, Dryer, Energy Efficient Appliances, Exhaust Fan, Icemaker, Microwave, Oven/Range - Electric, Refrigerator, Washer, Water Heater
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Laundry Type:Main Floor
Schools
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School District Name:Anne Arundel County Public Schools
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School District Source:Listing Agent
The Community
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Subdivision Name:Cape St John
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Senior Community:No
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Pool:No Pool
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HOA:No
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Condo/Coop Association:No
Parking
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Total Garage and Parking Spaces:10
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Garage:No
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Type of Parking:Driveway
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Driveway - # of Spaces:10
Extra Units
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Vacation Rental:No
Monthly cost estimate

Asking price
$569,999
Expense | Monthly cost |
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Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$3,052
|
Taxes | $435 |
Insurance | $156 |
Utilities | $186 See report |
Total | $3,829/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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7/15/25
Jul 15, 2025
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Listed / Active | BRIGHT | $569,999 |