1520 Circle Dr, Annapolis, MD 21409
Property image
Property image
OFF MARKET

$737,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,584 sqft (on 0.27 acres)

1520 Circle Dr, Annapolis, MD 21409

Est. Refi. Payment $4,489/mo*
Refinance Your Home
Currently Off Market - Sold Aug 27, 2024 for $680,000

Home Value

Trulia Estimate
$737K
Since last month
Decreased$700 (-0.1%)
Since last year
Increased$47K (+6.7%)
Since last sale
Increased$57K (+8.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +62% in the last 10 years
MonthEstimated value
2026
September 2026$737K
August 2026$738K
July 2026$747K
June 2026$759K
May 2026$765K
April 2026$748K
March 2026$726K
February 2026$697K
January 2026$685K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1505 Riverdale Dr, Annapolis, MD
0.14
Single-Family Home
$680,000
09/16/26
3
2
2,200
121 Severn Way, Arnold, MD
0.48
Single-Family Home
$595,000
09/18/26
3
2
1,736
165 Severn Way, Arnold, MD
0.36
Single-Family Home
$800,002
03/20/26
2
2
2,066
1438 Ridgeway E, Arnold, MD
0.37
Single-Family Home
$715,000
05/22/26
3
3
1,947
1465 Ridgeway, Arnold, MD
0.33
Single-Family Home
$552,500
06/24/26
3
2
1,560
1519 Winchester Rd, Annapolis, MD
0.11
Single-Family Home
$880,200
05/14/26
5
3
2,375
25 Pocono Dr, Arnold, MD
0.37
Single-Family Home
$560,000
02/17/26
3
2.5
2,008
1507 Circle Dr, Annapolis, MD
0.09
Single-Family Home
$840,000
09/19/25
4
3
2,600
184 Severn Way, Arnold, MD
0.36
Single-Family Home
$960,000
05/13/26
3
2
960
1446 Ridgeway, Arnold, MD
0.34
Single-Family Home
$605,000
02/13/26
2
2
1,538

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1507 Circle Dr, Annapolis, MD 21409
0.09
$849,100
4
3
2,600
Off Market
1505 Circle Dr, Annapolis, MD 21409
0.10
$2,261,700
4
3.5
3,260
Off Market
1501 Circle Dr, Annapolis, MD 21409
0.12
$1,552,600
4
2
2,914
Off Market
1534 Circle Dr, Annapolis, MD 21409
0.07
$860,000
4
3
3,233
Recently Sold
1501 Severncroft Rd, Annapolis, MD 21409
0.10
$1,308,300
3
2.5
3,855
Off Market
1511 Winchester Rd, Annapolis, MD 21409
0.10
$659,900
3
2.5
1,992
Off Market
1505 Riverdale Dr, Annapolis, MD 21409
0.14
$680,000
3
2
2,200
Recently Sold
1517 Winchester Rd, Annapolis, MD 21409
0.11
$900,500
4
3
2,662
Off Market
1519 Winchester Rd, Annapolis, MD 21409
0.11
$880,200
5
3
2,375
Recently Sold
1514 Winchester Rd, Annapolis, MD 21409
0.14
$921,000
3
3.5
2,311
Off Market
1604 Riverside Dr, Annapolis, MD 21409
0.15
$1,048,500
3
3
2,913
Off Market

Local Information

  • Map ViewExplore the area around 1520 Circle Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1963
0.27 acre lot
1,584 sqft
$465/sqft
1 Car Garage
HOA $22/mo

About this House

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!**
1520 Circle Dr, Annapolis, MD 21409 is a 3 bedroom, 2 bathroom, 1,584 sqft single-family home built in 1963. It last sold for $680,000 on Aug 27, 2024 (5% above the $649,999 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $737,100, with a rent estimate of $2,977/month.
Last check for updates: about 7 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

Home Details for 1520 Circle Dr

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $649,999
Status Change & Dates
Off Market Date: Tue Aug 27 2024Possession Timing: 0-30 Days CD, 31-60 Days CD

Active Status

MLS Status: CLOSED

Media

Location

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

Building

Building Area
Building Area: 1584 Square Feet

Community

Community Features: PoolNot Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Pier/Dock MaintenanceHOA Name: WINCHESTER ON THE SEVERN ASSOCIATIONHas an HOAHOA Fee: $260/Annually

Lot Information

Lot Area: 0.27 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Home InspectionListing Agreement Type: Exclusive AgencyListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2088684Above Grade Unfinished Area: 1584

Additional Information

HOA Amenities: Beach Access,Boat Dock/Slip,Boat Ramp,Common Grounds,Pier/Dock,Pool Mem Avail,Pool,Tot Lots/Playground

Price and Tax history

DateEventPrice
Aug 27, 2024
Source: Bright MLS #MDAA2088684
Sold
$680,000
Jul 10, 2024
Source: Bright MLS #MDAA2088684
Pending
$649,999
Jul 8, 2024
Source: Bright MLS #MDAA2088684
Contingent
$649,999
Jul 6, 2024
Source: Bright MLS #MDAA2088684
Listed For Sale
$649,999
Oct 23, 2020
Source: N/A
Sold
$495,000

Market trends in Annapolis

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$643K
$1KMoM
Sale-to-List Price
100.0%
Price per sq ft
$331
$6MoM
Available listings
344
11MoM

Around this home

What Locals Say about Annapolis

At least 470 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

  • 51 % 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.
  • Trulia User
    "Very dog friendly neighborhood. But not a lot of green space other than other peoples’ yards. "
    0
    Flag
  • Shannon Chatlos
    "If you like coastal living and a laid-back lifestyle, and are willing to pay for it, this a wonderful place to live."
    1
    Flag
  • Sylvie Bracke
    "It’s a very dog friendly place - I just can’t help wondering why some people don’t clean up after their pets? It’s a nice neighborhood with high end properties & I don’t get that dissonance."
    0
    Flag
  • Erin
    "Safe. On water. Paths in woods. Friendly. Dog play area. Lots of open spaces. Areas are walkable, clean. "
    0
    Flag
  • Halljanie68
    "Community Pool convenient shopping. Easy access to major routes 50/95 Easy access to downtown Annapolis "
    0
    Flag
  • Sheila Wilson
    "A lot of traffic on forest drive very hard to come onto the street. It need a red light or stop sign. Before a serious accident happens. People speed over 40mph"
    0
    Flag
  • Diana H.
    "I’m not sure, I don’t own a dog. Plenty walk by my dead end street house daily though and the neighborhood seems safe for both dogs and owners. "
    0
    Flag
  • Paul Eric Watson
    "Love the urban feel. Lots of history and near the water is a bonus. Very walkable and always something going on. "
    5
    Flag
  • Trulia User
    "Access to Route 50, the Bay Bridge, and Sandy Point State Park. Thirty minutes to Baltimore. Forty minutes to Washington D.C."
    2
    Flag
  • Trulia User
    "It’s a great neighborhood for kids and dogs Lots of walking areas, parks, water park and boat to downtown Annapolis "
    2
    Flag
  • Trulia User
    "It’s a tad busy commute rush hour traffic is something to consider small town lots of people takes about 10-15 min or so to get from one side of town to the other without traffic "
    1
    Flag
  • Trulia User
    "Great school public and private well maintained parks great public libraries close downtown Annapolis shopping for everything is conveniently close "
    0
    Flag
  • Trulia User
    "Lots of families with dogs. Poop bag stations throughout the neighborhood. Lots of woods to walk thru and sidewalks too. "
    1
    Flag
  • Trulia User
    "Nothing is special about my neighborhood. So quiet and nobody talks to anybody. The play area was demolished so no kids can hang out to play."
    4
    Flag
  • Trulia User
    "This is an excellent neighborhood for families and the neighbors are wonderful. Cape St. John gives you access to everything in Annapolis with the tranquility of living along the river."
    0
    Flag
  • Trulia User
    "While Truxton is dog friendly it would be nice to have a dedicated dog park closer than Quiet Waters. "
    0
    Flag
  • Trulia User
    "Wonderful family neighborhood. This neighborhood is very convenient to Hway 50 and all of the Annapolis area. The people here are terrific neighbors."
    0
    Flag
  • Trulia User
    "Good to walk. And parks are nice to play with kids. Stores are close by. And dog walkers all around. "
    0
    Flag
  • Trulia User
    "Summer beach parties, puppy happy hours, annual sock burning, lots of parks and the people are wonderful!"
    0
    Flag
  • Trulia User
    "the history Open napolis is amazing the people around here are kind and friendly and the schools are phenomenal"
    0
    Flag
  • Singletonad
    "the public school system in Annapolis needs to get significantly stronger overall. The private school system here is quite reliable."
    0
    Flag
  • Keren_molina
    "Lovely place and definitely good place to live and have a dog and a lot sores to go buy stuff ..........."
    5
    Flag
  • Singletonad
    "There is no community dog run here and no sidewalks so it can feel awkward letting your dog poop in someone else's yard even if you pick it up. The vast majority of neighbors are dog friendly, but not all, and that is their perogative."
    0
    Flag
  • Raddisob07
    " N/A school are great parking is great close to everything ppl are friendly and been living in Annapolis all my life "
    4
    Flag
  • Tery_hodges
    "I walk my son to elementary school. We can walk to many restaurants and “tourist” shops but do have to drive to get to a grocery store."
    2
    Flag
  • Stephanie.ward0715
    "I've been around this area for years. People are friendly and always willing to help each other. The restaurant's and shopping are also a plus. Everything you are looking for is 5 minutes away."
    0
    Flag
  • Raddisob07
    "None that I know of. The community should definitely do more collaborative events at least at least Quarterly they are family friendly."
    5
    Flag
  • Stella
    "Feel good living here Parking so easy Location very good Many things nearby Old town and new town "
    3
    Flag
  • Jennifer B.
    "It's super quiet and funny, I've leving here for 1 year and I feel safe my neighbors are nice.. Down town is amazing.. ❤️ "
    0
    Flag
  • Kwisniewski805
    "Holiday events and many boating events. There are street fairs, food markets, holiday markets. Community is very close. "
    0
    Flag
  • Cara M. E.
    "I teach at a school that is less than 10 minutes from my house. But there are times that Forest Dr gets incredibly backed up, or there is an accident that causes the road to be shut down. "
    1
    Flag
  • Beth S.
    "Bad area is close by, so kids need to understand boundaries. Private schools are important here, so save your money. Sports are good here, with lots of good coaching."
    0
    Flag
  • Linda D.
    "I've been visiting a dear close friend - helping them recuperate from serious surgery. traffic is atrocious- I miss living in the rural countryside area!"
    0
    Flag
  • Liza
    "The schools in Annapolis are not as good as they are in Severna Park which is where I grew up originally. But Annapolis has many great amenities including local places to eat and shop."
    0
    Flag
  • Rodwellsantos6
    "I like it this community is pretty good as so matters fact for elders we looking to buy in this areas I don’t know frankly about this gorgeous homes we will see."
    0
    Flag
  • Jeffrey H.
    "Lived here for 4 years. Loved the area, including the park across the street. Hate the maintenance of the building including the attention to detail of maintenance of property. "
    0
    Flag
  • jfh4k0
    "Local traffic is not too bad. Beach traffic and rush hour traffic to DC and Baltimore is pretty terrible. "
    2
    Flag
  • Nadja Maril
    "I lived in this neighborhood over 20 years and walk downtown with my dog every morning for coffee. On pretty days we visit City Dock and admire the views and the boats."
    1
    Flag
  • Markkimethanmolly
    "We’ve lived here for 18 years, and everyone is very friendly. Our neighborhood is very safe and quiet."
    0
    Flag
  • Debwill64
    "There is a bus stop close enough to walk to but I have to drive to DC. The bus only goes to Annapolis and maybe Baltimore, not sure though."
    0
    Flag

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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

Frequently asked questions about 1520 Circle Dr

  • What is 1520 Circle Dr estimated to be worth?
    Trulia's estimated value for 1520 Circle Dr in Annapolis, MD is $737,100.
  • What is the price history for 1520 Circle Dr?
    1520 Circle Dr in Annapolis, MD last sold for $680,000 in August 2024.
  • Is Annapolis a buyer's or seller's market?
    Annapolis is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Annapolis?
    The median sale price in Annapolis is $643K. That is down $1K from the prior month.
  • Does 1520 Circle Dr have air conditioning?
    Yes, 1520 Circle Dr in Annapolis, MD has air conditioning.
  • Does 1520 Circle Dr have a pool?
    Yes, 1520 Circle Dr in Annapolis, MD has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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