165 Woodside Trail, Annapolis, MD 21401 - Photo 1

1/1

$575,000

Sold
Closed
Single Family
4 Beds
2 Full Baths
2,720 Sq. Ft.

1/1

Property Description

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.

Full Property Details

Full Property Details for 165 Woodside Trail

General

Sold For: $575,000
Taxes: $5,220 (2024)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDAA2120210
Added to Site: 262 day(s) ago

Interior

Fireplace: Yes
Number of Fireplaces: 1
Fireplace(s): Brick, Wood, Brick, Wood
Appliances: Dishwasher, Dryer, Energy Efficient Appliances, Exhaust Fan, Icemaker, Microwave, Oven/Range - Electric, Refrigerator, Washer, Water Heater

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2
Main Floor Baths: 2
Main - Full Baths: 2

Bedrooms

Total Bedrooms: 4
Bedrooms Main & Up: 4

Other Rooms

Laundry: Main Floor

Parking

Total Spaces: 10
Parking Type: Driveway

Location

County: Anne Arundel
Development Name: Cape St John
Subdivision: Cape St John
Driving Directions: Use GPS

School Information

School District: Anne Arundel County Public Schools

Heating & Cooling

Central air: Yes
Cooling Type: Ceiling Fan(s), Central A/C
Cooling Fuel: Electric
Heating Type: Heat Pump - Oil BackUp, Central
Heating Fuel: Electric, Oil
Water Heater: Electric

Utilities

Sewer: Public Sewer
Water: Public

Structural Information

Architectural Info: Ranch/Rambler
Architectural Style: Ranch/Rambler
Structure Type: Detached
Construction: Vinyl Siding
Basement: Yes
Basement Entrance: Yes
Basement Desc.: Interior Access, Outside Entrance, Poured Concrete, Rear Entrance, Sump Pump, Unfinished, Walkout Stairs
Foundation: Concrete Perimeter
Stories/Levels: 0
Stories Description: Main
Square Feet: 2,720
Sq. Ft. Source: Assessor
Living Area: 1,360 Sq. Ft.
Year Built: 1980
Year Built Source: Assessor
Property Condition: Excellent

Lot Features

Lot Size (Acres): 0.31
Lot Size (Sq. Ft.): 13,650
Lot Size Source: Assessor
Zoning: R2

Water Features

Navigable Water: Yes
Water Access: Yes
Water Access Desc: Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, Waterski/Wakeboard
Water Front Type: River
Water Front Name: South River

Financial Considerations

Price Per Sq. Ft.: $419.12
Assessment Year: 2025
County Tax: $4,840
County Tax Freq: Annually
Tax w/Assessment: $452,867
Tax Amount: $5,220
Tax Year: 2024
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 1360

Disclosures and Reports

Ownership: Fee Simple
Section: D
Lot Number: 166

Listed by Douglas Realty LLC, Robert M Carter Jr. and Douglas Realty LLC, ERIN CARTER
Sold by Coldwell Banker Waterman Realty, Virginia Elizabeth Dauses

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Listing agents

— 165 Woodside Trail —

Robert M Carter Jr.

Douglas Realty LLC
ERIN CARTER

Douglas Realty LLC

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Schools

Schools serving 165 Woodside Trail

School District:Anne Arundel County Public Schools

Name	Grades	Distance
Rolling Knolls Elementary School 1985 Valley Road, Annapolis, MD 21401	PK-5	2.8 mi
Wiley H. Bates Middle School 701 Chase Street, Annapolis, MD 21401	6-8	3.2 mi
Annapolis High School 2700 Riva Road, Annapolis, MD 21401	9-12	1.1 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 165 Woodside Trail

Date

Details

Price

Change

Source

8/22/2025

Sold

$575,000

0.88%

MLS

7/15/2025

Listed

$569,999

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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165 Woodside Trail, Annapolis, MD 21401 (MLS# MDAA2120210) is a Single Family property that was sold at $575,000 on August 22, 2025. Want to learn more about 165 Woodside Trail? Do you have questions about finding other Single Family real estate for sale in Annapolis? You can browse all Annapolis real estate or contact a Coldwell Banker agent to request more information.

165 Woodside Trail Annapolis, MD 21401