1505 Circle Dr, Annapolis, MD 21409
Property image
Property image
OFF MARKET

$2,269,600

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,260 sqft (on 0.47 acres)

1505 Circle Dr, Annapolis, MD 21409

Est. Refi. Payment $13,159/mo*
Refinance Your Home
Currently Off Market - Sold Nov 8, 2023 for $1,925,000

Home Value

Trulia Estimate
$2.27M
Since last month
Decreased$19K (-0.8%)
Since last year
Increased$14K (+0.6%)
Since last sale
Increased$347K (+18%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$2.27M
August 2026$2.27M
July 2026$2.29M
June 2026$2.32M
May 2026$2.34M
April 2026$2.33M
March 2026$2.32M
February 2026$2.27M
January 2026$2.26M
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
1507 Circle Dr, Annapolis, MD
0.01
Single-Family Home
$840,000
09/19/25
4
3
2,600
1534 Circle Dr, Annapolis, MD
0.16
Single-Family Home
$860,000
12/03/25
4
3
3,233
45 Sierra Ln, Arnold, MD
0.22
Single-Family Home
$780,000
07/16/26
4
3
2,707
1519 Winchester Rd, Annapolis, MD
0.20
Single-Family Home
$880,200
05/14/26
5
3
2,375
36 Sierra Ln, Arnold, MD
0.25
Single-Family Home
$750,000
12/19/25
4
3
2,110
1516 Briarcliff Rd, Arnold, MD
0.52
Single-Family Home
$1,300,000
08/14/26
4
3.5
3,035
1438 Ridgeway E, Arnold, MD
0.28
Single-Family Home
$715,000
05/22/26
3
3
1,947
25 Cascade Rd, Arnold, MD
0.31
Single-Family Home
$765,000
07/17/26
4
2
2,464
1635 Winchester Rd, Annapolis, MD
0.58
Single-Family Home
$1,139,400
03/26/26
5
4
3,660
1553 Ashcroft Ln, Arnold, MD
0.49
Single-Family Home
$800,000
06/05/26
5
3.5
3,910

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
1501 Circle Dr, Annapolis, MD 21409
0.03
$1,552,100
4
2
2,914
Off Market
1507 Circle Dr, Annapolis, MD 21409
0.01
$849,100
4
3
2,600
Off Market
1520 Circle Dr, Annapolis, MD 21409
0.10
$737,100
3
2
1,584
Off Market
157 Edgeway, Arnold, MD 21012
0.14
$1,272,600
4
3
1,935
Off Market
1534 Circle Dr, Annapolis, MD 21409
0.16
$860,000
4
3
3,233
Recently Sold
1501 Severncroft Rd, Annapolis, MD 21409
0.17
$1,313,000
3
2.5
3,855
Off Market
1511 Winchester Rd, Annapolis, MD 21409
0.20
$659,900
3
2.5
1,992
Off Market
1519 Winchester Rd, Annapolis, MD 21409
0.20
$880,200
5
3
2,375
Recently Sold
1517 Winchester Rd, Annapolis, MD 21409
0.20
$908,200
4
3
2,662
Off Market
1504 Severncroft Rd, Annapolis, MD 21409
0.23
$2,999,100
5
5.5
6,225
Off Market
1465 Ridgeway, Arnold, MD 21012
0.23
$552,500
3
2
1,560
Recently Sold

Local Information

  • Map ViewExplore the area around 1505 Circle Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1966
0.47 acre lot
3,260 sqft
$696/sqft
Open Parking

About this House

Charming deep water home on Chase Creek in Winchester-on-the-Severn. Over 3,200 sqft of living space spread across 3 levels with walls of glass to capture the serene water views. Open bright interior, totally renovated kitchen and 4 ultra luxe baths. Deep water pier with 50' slip, 20,000 boat lift, PWC lift & 50 amp shore power. To many upgrades to list including: Architectural shingle roof, Paver drwy, 20KW Generator, Outdoor shower, Sauna, (2) waterside composite decks, custom landscaping, lighting and terracing. Just minutes to Rt. 50 and downtown Annapolis. Winchester-on-the-Severn is a fabulous community with public water, natural gas and THE best private beach on the Severn River. The community amenities are second to none, including a boat ramp, (4) piers, marina, beach pavilion, playground, and dog beach, plus the Chase Creek swim club and the B&A Trail is right up the street. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis and Severna Park. Convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. If you are looking for a truly unique property with stunning water views and a great neighborhood setting, this is one opportunity you don't want to miss!
1505 Circle Dr, Annapolis, MD 21409 is a 4 bedroom, 4 bathroom, 3,260 sqft single-family home built in 1966. It last sold for $1,925,000 on Nov 8, 2023 (2% above the $1,895,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,269,600, with a rent estimate of $5,050/month.
Last check for updates: about 17 hours ago
Listed by Brad Kappel, (410) 279-9476
TTR Sotheby's International Realty
Bought with: Georgie Berkinshaw, (443) 994-4456, Coldwell Banker Realty
Source: Bright MLS, MLS#MDAA2069094

Home Details for 1505 Circle Dr

Interior Features

Interior Details
Basement: Connecting Stairway,Exterior Entry,Rear Entrance,Full,Improved,Walk-Out Access,Finished,HeatedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 3260 Square Feet
Appliances & Utilities
Utilities: Fiber OpticAppliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Ice Maker, Self Cleaning Oven, Oven/Range - Gas, Refrigerator, Washer, Energy Efficient Appliances, Dual Flush Toilets, Microwave, Tankless Water Heater, Gas Water HeaterDishwasherDisposalDryerLaundry: Upper Level,In Basement,Washer/Dryer Hookups OnlyMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,Baseboard,Electric,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,Whole House Fan,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Mantel(s), Screen, Gas/Propane, Wood BurningHas a Fireplace
Gas & Electric
Electric: Generator
Windows, Doors, Floors & Walls
Window: Screens, Skylight(s), Window TreatmentsDoor: French Doors, Sliding GlassFlooring: Ceramic Tile, Hardwood, Heated, Wood
Levels, Entrance, & Accessibility
Stories: 3Number of Stories: 3Levels: ThreeAccessibility: NoneFloors: Ceramic Tile, Hardwood, Heated, Wood
View
Has a ViewView: Water, Scenic Vista
Security
Security: 24 Hour Security, Monitored, Motion Detectors, Security System, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PatioFencing: Back Yard, Invisible, Split RailOther Structures: Above Grade, Below GradeExterior: Extensive Hardscape, Outdoor Shower, Flood Lights, Play Area, BalconyFoundation: BlockNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Off Street
Pool
Pool: None
Frontage
WaterfrontWaterfront: Private Dock Site, Creek/Stream, Private Access, Boat - Powered, Canoe/Kayak, Fishing Allowed, SailOn Waterfront
Water & Sewer
Sewer: Septic ExistsWater Body: Chase Creek
Farm & Range
Frontage Length: Water Frontage Ft: 125
Finished Area
Finished Area (above surface): 2310 Square FeetFinished Area (below surface): 950 Square Feet

Property Information

Year Built
Year Built: 1966Year Renovated: 2014
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Coastal
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Condition: ExcellentParcel Number: 020390932421755

Price & Status

Price
List Price: $1,895,000
Status Change & Dates
Off Market Date: Wed Nov 08 2023Possession Timing: Immediate

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 Details
Builder Model: CHASE CREEK WATERFRONT
Building Area
Building Area: 3260 Square Feet

Community

Not Senior Community

HOA

HOA Name: WINCHESTER-ON-THE-SEVERNNo HOA

Lot Information

Lot Area: 0.47 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Financing ApprovalListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2069094Water ViewWater View: WaterAbove Grade Unfinished Area: 2310

Additional Information

HOA Amenities: Beach Access,Pier/Dock,Tot Lots/Playground,Water/Lake Privileges,Mooring Area,Pool Mem Avail

Price and Tax history

DateEventPrice
Nov 8, 2023
Source: Bright MLS #MDAA2069094
Sold
$1,925,000
Oct 2, 2023
Source: Bright MLS #MDAA2069094
Pending
$1,895,000
Mar 24, 2021
Source: N/A
ListingRemoved
Dec 27, 2016
Source: N/A
ListingRemoved
$1,295,000
Dec 24, 2016
Source: N/A
Listed For Sale
$1,295,000

Market trends in Annapolis

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$646K
$11.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$326
$7MoM
Available listings
355
3MoM

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."
    0
    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 1505 Circle Dr

  • What is 1505 Circle Dr estimated to be worth?
    Trulia's estimated value for 1505 Circle Dr in Annapolis, MD is $2,269,600.
  • What is the price history for 1505 Circle Dr?
    1505 Circle Dr in Annapolis, MD last sold for $1,925,000 in November 2023.
  • 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 $646K. That is up $11.67K from the prior month.
  • Does 1505 Circle Dr have air conditioning?
    Yes, 1505 Circle Dr in Annapolis, MD has air conditioning.
  • Does 1505 Circle Dr have a pool?
    Yes, 1505 Circle Dr in Annapolis, MD has a pool.

Explore by feature - Pet Friendly

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