1520 Circle Dr
Annapolis, MD 21409
- 3 Beds
- 2 Baths
- 1,584 sqft (on 0.27 acres)
3 Beds
2 Baths
1,584 sqft
(on 0.27 acres)
Local Information
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Description
This is your opportunity to experience the water privileged and highly coveted neighborhood of Winchester-on-the-Severn! 1520 Circle Drive is a wide corner lot with 2 driveways, 3 bedrooms and 2 baths. Enter into a light filled and stylish split level with tasteful built-in’s, trendy brass accents, wood flooring and tons of windows. Enjoy cooking with a full suite of stainless-steel appliances in the eat-in kitchen, appreciate the indoor-outdoor living of your huge screened-in porch, host dinner parties in your dining room, or watch the sunset in the graceful living room. Up the stairs, you are greeted by wood flooring, three bedrooms and two bathrooms, including an en suite for the primary, and hall bath. The lower level is a perfect flex space of family room – office – den, with laundry in the light filled and well-kept garage with a basement walkout. This is a vibrant community with a shared love of the outdoors waterfront lifestyle, including neighborhood parties and an air of camaraderie. The community shares a private beach off the spectacular Severn River with a full pavilion and grill set up, a pier perfect for fishing, crabbing, with updated playground, kayaking and paddle board storage, a flat grassy area for playing, and parking lot for both cars and golf carts. Stroll over to the boat floats and slips, the neighborhood pool and swim club, the swimming or dog friendly beach, or just enjoy the beautiful landscaping while walking or biking over to the nearby B&A trail. Just minutes from major commuter routes 50 & 97, and close to downtown Annapolis either by car or boat. **This is a rare opportunity for potential to expand the property footprint on a flat lot in sought after Winchester-on-the-Severn! This home is move-in ready, but also provides opportunity for future enlargement with a recently upgraded new septic system and permitted expansion plans. Do not miss!**
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from September 23, 2024
Home Highlights
Parking
1 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
$22/Monthly
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 1520 Circle Dr
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Interior Details Basement: Partial,Improved,Interior Entry,Walk-Out AccessNumber of Rooms: 1Types of Rooms: Basement |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 1584 Square Feet |
Appliances & Utilities Appliances: Microwave, Dishwasher, Dryer, Refrigerator, Cooktop, Washer, Water Heater, Gas Water HeaterDishwasherDryerLaundry: Dryer In Unit,Washer In UnitMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace |
Windows, Doors, Floors & Walls Flooring: Hardwood, Carpet, Wood |
Levels, Entrance, & Accessibility Stories: 3Levels: Multi/Split, ThreeAccessibility: NoneFloors: Hardwood, Carpet, Wood |
View No View |
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Exterior Home Features Other Structures: Above Grade, Below GradeFoundation: Crawl SpaceNo Private Pool |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Garage Faces Rear,Storage,Inside Entrance,Attached,Driveway |
Pool Pool: Community |
Frontage Waterfront: River, Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Public Access, Beach Access, Sail, Swimming Allowed, Waterski/WakeboardNot on Waterfront |
Water & Sewer Sewer: Septic Exists, Septic > # of BRWater Body: Severn River |
Farm & Range Not Allowed to Raise Horses |
Finished Area Finished Area (above surface): 1584 Square Feet |
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Year Built Year Built: 1963 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Detached |
Building Construction Materials: Brick, Aluminum SidingNot a New ConstructionNo Additional Parcels |
Property Information Included in Sale: Living Room Tv And Mount, Green Cabinets In Screen PorchParcel Number: 020390926564320 |
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Price List Price: $649,999 |
Status Change & Dates Off Market Date: Tue Aug 27 2024Possession Timing: 0-30 Days CD, 31-60 Days CD |
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MLS Status: CLOSED |
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Direction & Address City: ANNAPOLISCommunity: Winchester On The Severn |
School Information Elementary School: ArnoldElementary School District: Anne Arundel County Public SchoolsJr High / Middle School: Severn RiverJr High / Middle School District: Anne Arundel County Public SchoolsHigh School: BroadneckHigh School District: Anne Arundel County Public Schools |
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Building Area Building Area: 1584 Square Feet |
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Community Features: PoolNot Senior Community |
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HOA Fee Includes: Common Area Maintenance, Pier/Dock MaintenanceHOA Name: WINCHESTER ON THE SEVERN ASSOCIATIONHas an HOAHOA Fee: $260/Annually |
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Lot Area: 0.27 acres |
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Special Conditions: Standard |
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Contingencies: Home InspectionListing Agreement Type: Exclusive AgencyListing Terms: Cash, Conventional, FHA, VA Loan |
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Business Information Ownership: Fee Simple |
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BasementMls Number: MDAA2088684Above Grade Unfinished Area: 1584 |
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HOA Amenities: Beach Access,Boat Dock/Slip,Boat Ramp,Common Grounds,Pier/Dock,Pool Mem Avail,Pool,Tot Lots/Playground |
Last check for updates: about 6 hours ago
Listed by Adam Chasen, (301) 461-7021
Compass
Co-Listing Agent: Georgia Paulding Chasen, (443) 562-1263
Compass
Bought with: Alan Chargin, (202) 999-2122, Keller Williams Capital Properties
Source: Bright MLS, MLS#MDAA2088684

Price History for 1520 Circle Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 08/27/2024 | $680,000 | Sold | Bright MLS #MDAA2088684 |
| 07/10/2024 | $649,999 | Pending | Bright MLS #MDAA2088684 |
| 07/08/2024 | $649,999 | Contingent | Bright MLS #MDAA2088684 |
| 07/06/2024 | $649,999 | Listed For Sale | Bright MLS #MDAA2088684 |
| 10/23/2020 | $495,000 | Sold | N/A |
| 09/05/2020 | $499,900 | Pending | Agent Provided |
| 08/18/2020 | $499,900 | PriceChange | Agent Provided |
| 06/23/2020 | $509,900 | Pending | Agent Provided |
| 05/15/2020 | $509,900 | PriceChange | Agent Provided |
| 02/19/2020 | $519,900 | Listed For Sale | Agent Provided |
Market trends in Annapolis
Last updated May 2026
Avg. sale price
$625K
$30.52KMoM
Sale-to-List Price
100.0%
0.3%MoM
Price per sq ft
$313
$3MoM
Available listings
378
43MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $6,248 |
| Assessment | $525,567 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$2,992/mo
Homes for rent near 1520 Circle Dr
See what comparable homes in the neighborhood are renting for.Comparable Sales for 1520 Circle Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.36 | Single-Family Home | $800,002 | 03/20/26 | 2 | 2 | 2,066 | |
0.37 | Single-Family Home | $715,000 | 05/22/26 | 3 | 3 | 1,947 | |
0.11 | Single-Family Home | $880,200 | 05/14/26 | 5 | 3 | 2,375 | |
0.37 | Single-Family Home | $560,000 | 02/17/26 | 3 | 2.5 | 2,008 | |
0.09 | Single-Family Home | $840,000 | 09/19/25 | 4 | 3 | 2,600 | |
0.36 | Single-Family Home | $960,000 | 05/13/26 | 3 | 2 | 960 | |
0.39 | Single-Family Home | $730,000 | 07/31/25 | 4 | 2.5 | 2,075 | |
0.34 | Single-Family Home | $605,000 | 02/13/26 | 2 | 2 | 1,538 | |
0.28 | Single-Family Home | $750,000 | 12/19/25 | 4 | 3 | 2,110 | |
0.48 | Single-Family Home | $495,000 | 11/19/25 | 5 | 3 | 2,225 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 1520 Circle Dr.
What Locals Say about Annapolis
At least 469 Trulia users voted on each feature.
93 % Say it's dog friendly
83 % Say car is needed
75 % Say there's holiday spirit
73 % Say parking is easy
73 % Say there are sidewalks
70 % Say yards are well-kept
68 % Say people would walk alone at night
68 % Say kids play outside
66 % Say streets are well-lit
65 % Say it's quiet
63 % Say there's wildlife
57 % Say it's walkable to restaurants
57 % Say neighbors are friendly
52 % Say they plan to stay for at least 5 years
49 % Say there are community events
48 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 1520 Circle Dr
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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, and is provided by BRIGHT through a licensing agreement.
Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site.
The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc. Click here for more information
1520 Circle Dr, Annapolis, MD 21409 is a 3 bedroom, 2 bathroom, 1,584 sqft single-family home built in 1963. This property is not currently available for sale. 1520 Circle Dr was last sold on Aug 27, 2024 for $680,000 (5% higher than the asking price of $649,999). The current Trulia Estimate for 1520 Circle Dr is $767,000.

