Backup offers
#MDAA2118006, Kathleen Moore, Listing office: Engel & Volkers Annapolis
$569,999 List price
165 Woodside Trl Annapolis, MD 21401
4 beds
2 full
1,360 sqft
0.3 acres
$419 / sqft
House
Property details
About 165 Woodside Trl
*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.
Highlights
Home typeSingle Family Residence
HeatingHeat Pump, Central
StatusActive
(ACTIVE)
(ACTIVE)
CoolingCeiling Fan(s), Central Air
Size1,360 sqft
BasementYes
Lot size0.31 Acres
Year built1980
ParkingDriveway
MLS #MDAA2120210
FireplaceBrick, Wood
Summary
- Full Bathrooms: 2
- Appliances: Dishwasher, Dryer, Exhaust Fan, Ice Maker, Microwave, Oven, Electric Range, Refrigerator, Washer, Water Heater
- Basement: Yes
- Fireplace: Brick, Wood
- Total Bedroom Count: 4
- Parking: Driveway
- Architectural Style: Ranch/Rambler
- Heating: Heat Pump, Central
- Cooling: Ceiling Fan(s), Central Air
- List Price: $569,999
- Price/SqFt: $419
- Annual Tax Amount: $2,903
- Tax Year: 2024
- Directions: Use GPS
- Year Built: 1980
- Stories: 2
- Living Area: 1,360 SqFt
- Lot Size: 0.31 Acres
- MLS Number: MDAA2120210
- MLS Name: BRIGHT
- Office Name: Douglas Realty LLC
- Office Phone: (410) 255-3690
- Office Email: info@godouglasrealty.com
- Listing Agent: Robert M Carter Jr.
- Agent Phone: (443) 677-3058
- Agent Email: rob@godouglasrealty.com
Information Deemed Reliable But Not Guaranteed. 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 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 sold or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.
BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors. ©2025 BrightMLS. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/15/2025, 9:45:32 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $442,033 | $2,903 |
| 2023 | $431,200 | $2,903 |
| 2022 | $425,200 | $4,443 |
| 2021 | $419,200 | $4,189 |
| 2020 | $413,200 | $3,023 |
| 2018 | $413,200 | $2,863 |
| 2017 | $415,300 | $2,837 |
History based on county public records data.
Nearby schools
6
Edgewater Elementary School
Public District KG-5
1.4 mi
•121 Washington Rd
3
Walter S. Mills - Parole Elementary School
Public District PK-5
2.3 mi
•1 George and Marion Phelps Ln
5
Central Elementary School
Public District KG-5
2.4 mi
•130 Stepney Ln
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $104,134. The most common annual income of people living in Annapolis, MD is between $35k-100k. The majority of families are single, no kids. Typical level of education for residents in this area is post secondary degree.
How much money do the neighbors make?
13%
<35k
35%
35k-100k
32%
100k-200k
20%
200k+
What level of education do the neighbors have?
No High School
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
51%
Single, No Kids
1%
Single, with Kids
39%
Married, No Kids
9%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
7%
<11 yrs old
3%
12-17 yrs old
8%
18-34 yrs old
40%
35-64 yrs old
42%
65+ yrs old
What do the neighbors do for fun?
PGA/LPGA
Men's Tennis
Skiing/snowboarding
Where do the neighbors shop?
Chico's
Bloomingdales
Nordstrom
Where do the neighbors go to eat?
Bonefish Grill
California Pizza Kitchen
Chipotle
What do the neighbors drive?
Cadillac
Lexus
BMW
What do the neighbors listen to?
Classical
News
Talk/Personality
All data provided by Home Junction and Claritas
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Frequently asked questions
About 165 Woodside Trl
The listing price of 165 Woodside Trl property is $569,999.
The property 165 Woodside Trl is a house located in Annapolis, Maryland, 21401.
Active Listing: 165 Woodside Trl is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 165 Woodside Trl are: Edgewater Elementary School (GreatSchools Rating 6/10), Walter S. Mills - Parole Elementary School (GreatSchools Rating 3/10), Central Elementary School (GreatSchools Rating 5/10), Annapolis Middle School (GreatSchools Rating 2/10), Central Middle School (GreatSchools Rating 8/10), Wiley H. Bates Middle School (GreatSchools Rating 5/10), Annapolis High School (GreatSchools Rating 3/10), South River High School (GreatSchools Rating 9/10), Crofton High School (GreatSchools Rating 8/10).
According to the records, the last property tax for 2024 is $2,903 (source: MLS/based on county public records data).
The property at 165 Woodside Trl has 4 bedrooms and 2 bathrooms.
The property 165 Woodside Trl is 1,360 SqFt (source: MLS/tax record).
The year of construction for 165 Woodside Trl is 1980.
This home is located at 165 Woodside Trl in Annapolis, MD and zip code 21401 in the Parole neighborhood. This 1,360 square foot home, which was built in 1980, sits on a 0.31 acre lot. Features: 4 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since July 15, 2025 and is currently priced at $569,999.
In June 2025 in Annapolis, MD there were 63.5% more homes for sale than in May. The median list price of listings available in June 2025 was $699,900, while the average time on the real estate market was 64 days.
From Rocket Homes Real Estate and based on county public records data.