1534 Circle Dr, Annapolis, MD 21409
Property image
Property image
SOLD
DEC 3, 2025

$867,600

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,233 sqft (on 0.58 acres)

1534 Circle Dr, Annapolis, MD 21409

Est. Refi. Payment $5,271/mo*
Refinance Your Home
Currently Off Market - Sold Dec 3, 2025 for $860,000 (4% below list price)

Home Value

Trulia Estimate
$868K
Since last month
$200 (0%)
Since last year
Decreased$69K (-7.3%)
Since last sale
Increased$9K (+1%)
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 +47% in the last 10 years
MonthEstimated value
2026
September 2026$869K
August 2026$868K
July 2026$879K
June 2026$872K
May 2026$869K
April 2026$859K
March 2026$863K
February 2026$862K
January 2026$856K
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
1519 Winchester Rd, Annapolis, MD
0.06
Single-Family Home
$880,200
05/14/26
5
3
2,375
45 Sierra Ln, Arnold, MD
0.29
Single-Family Home
$780,000
07/16/26
4
3
2,707
36 Sierra Ln, Arnold, MD
0.32
Single-Family Home
$750,000
12/19/25
4
3
2,110
25 Cascade Rd, Arnold, MD
0.41
Single-Family Home
$765,000
07/17/26
4
2
2,464
1505 Riverdale Dr, Annapolis, MD
0.20
Single-Family Home
$680,000
09/16/26
3
2
2,200
1438 Ridgeway E, Arnold, MD
0.43
Single-Family Home
$715,000
05/22/26
3
3
1,947
1553 Ashcroft Ln, Arnold, MD
0.62
Single-Family Home
$800,000
06/05/26
5
3.5
3,910
25 Pocono Dr, Arnold, MD
0.42
Single-Family Home
$560,000
02/17/26
3
2.5
2,008
1635 Winchester Rd, Annapolis, MD
0.59
Single-Family Home
$1,139,400
03/26/26
5
4
3,660

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
1520 Circle Dr, Annapolis, MD 21409
0.07
$737,100
3
2
1,584
Off Market
1511 Winchester Rd, Annapolis, MD 21409
0.04
$659,900
3
2.5
1,992
Off Market
1501 Severncroft Rd, Annapolis, MD 21409
0.06
$1,308,300
3
2.5
3,855
Off Market
1517 Winchester Rd, Annapolis, MD 21409
0.05
$900,500
4
3
2,662
Off Market
1519 Winchester Rd, Annapolis, MD 21409
0.06
$880,200
5
3
2,375
Recently Sold
1514 Winchester Rd, Annapolis, MD 21409
0.07
$921,000
3
3.5
2,311
Off Market
1604 Riverside Dr, Annapolis, MD 21409
0.09
$1,048,500
3
3
2,913
Off Market
1507 Circle Dr, Annapolis, MD 21409
0.15
$849,100
4
3
2,600
Off Market
1505 Circle Dr, Annapolis, MD 21409
0.16
$2,261,700
4
3.5
3,260
Off Market
1501 Circle Dr, Annapolis, MD 21409
0.18
$1,552,600
4
2
2,914
Off Market
1504 Severncroft Rd, Annapolis, MD 21409
0.16
$2,969,000
5
5.5
6,225
Off Market

Local Information

  • Map ViewExplore the area around 1534 Circle Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1977
0.58 acre lot
3,233 sqft
$266/sqft
4 Open Spaces

About this House

Nestled into the tree tops off a private drive in highly sought after Winchester on the Severn, this mid century raised rancher will check all your boxes. From the moment you pull up the private drive to the home, you are immediately at ease. Step out of the car to the sounds of birds and the rustle of the trees. You will feel as though you have escaped it all, yet you are right in the heart of Winchester, a quick drive from Historic Downtown Annapolis and a stones throw to the famed B&A trail. As you enter the front walk, you will be immediately struck by the quality of craftsmanship and materials on the exterior of the home. Once inside, the rich wood beams, wood trim and floors strike a dramatic combination with the soaring ceilings. The abundant windows and doors leading out to the sunroom will ensure that the beauty of the natural surroundings take center stage. The chef's kitchen is equipped with granite countertops, a deep sink, lovely picture window over the sink, double wall ovens and high end fixtures. The sunroom serves as an additional dining space and relaxing sitting room with full views of the surroundings. You will feel as though you have escaped to a mountain retreat! The main level offers a full hall bath and three comfortable bedrooms including an owner's suite with ensuite bath and double closets. The fully finished lower level is a lovely living space on its own with a cozy den, office and flexible bonus space that could be a 4th bedroom with its own ensuite bath. The lower sunroom is the perfect spot to partake in your morning yoga and meander out to the hot tub for a leisurely soak. Entertaining is a breeze with the expansive, multi-level decks and putting green for fun. After a day on the water, use the outdoor shower to rinse away the salt and sand. Winchester offers two beaches (one is referred to as Dog Beach for obvious reasons) and two marinas. The beauty of a water access community on the Severn River is easy access into Annapolis by boat without going out into the choppy Bay. You can hop on a small tender and dock in town at the dinghy dock for dinner any time you please. Walk or bike up the B&A trail for coffee, ice cream or grab must haves at the gourmet cheese shop. Brunch at the Severn Inn overlooking the River or pop over to Garten Beer Garden for a lovely supper with friends. This is not merely a beautiful home, this is a highly sought after lifestyle.
1534 Circle Dr, Annapolis, MD 21409 is a 4 bedroom, 3 bathroom, 3,233 sqft single-family home built in 1977. It last sold for $860,000 on Dec 3, 2025 (4% below the $899,000 asking price). More recently, it was listed as a rental in November 2024 with an asking price of $2,999 per month. That rental listing was removed on November 25, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $867,600, with a rent estimate of $4,479/month.
Last check for updates: about 2 hours ago
Listed by Michele Deckman, (410) 353-3703
TTR Sotheby's International Realty
Listing Team: The Tower Team Of Ttr Sotheby's International Realty
Bought with: Jessica Verde, (443) 994-5481, Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS, MLS#MDAA2128442

Home Details for 1534 Circle Dr

Interior Features

Interior Details
Basement: Full,Finished,Heated,Improved,Interior Entry,Exterior EntryNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 3233 Square Feet
Appliances & Utilities
Appliances: Down Draft, Dishwasher, Dryer, Exhaust Fan, Double Oven, Oven, Refrigerator, Washer, Water Heater, Electric Water HeaterDishwasherDryerLaundry: Lower LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Brick, Equipment, Mantel(s), Wood BurningSpa: Hot TubHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Window: CasementFlooring: Wood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoAccessibility: NoneFloors: Wood
View
Has a ViewView: Trees/Woods

Exterior Features

Exterior Home Features
Patio / Porch: Deck, PatioOther Structures: Above Grade, Below Grade, OutbuildingExterior: Extensive Hardscape, Lighting, Flood Lights, Outdoor ShowerFoundation: BlockNo Private Pool
Parking & Garage
Number of Carport Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4Has a CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 6Parking: Crushed Stone,Lighted,Private,Detached Carport,Driveway,Off Street
Pool
Pool: Community
Frontage
Waterfront: Boat - Powered, Canoe/Kayak, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, RiverResponsible for Road Maintenance: Easement/Right of Way, Private Maintained RoadNot on Waterfront
Water & Sewer
Sewer: On Site SepticWater Body: Severn River
Finished Area
Finished Area (above surface): 1815 Square FeetFinished Area (below surface): 1418 Square Feet

Property Information

Year Built
Year Built: 1977
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Mid-Century Modern,Raised Ranch/Rambler
Building
Construction Materials: CombinationNot a New Construction
Property Information
Condition: Very GoodParcel Number: 020390929323990

Price & Status

Price
List Price: $899,000Price Per Sqft: $266/sqft
Status Change & Dates
Off Market Date: Wed Dec 10 2025Possession 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 Area
Building Area: 3470 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.58 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2128442Above Grade Unfinished Area: 1815

Price and Tax history

DateEventPrice
Dec 3, 2025
Source: Bright MLS #MDAA2128442
Sold
$860,000
Nov 6, 2025
Source: Bright MLS #MDAA2128442
Contingent
$899,000
Oct 30, 2025
Source: Bright MLS #MDAA2128442
PriceChange
$899,000
Price decreased by 7%
Oct 14, 2025
Source: Bright MLS #MDAA2128442
Listed For Sale
$965,000
Sep 30, 2025
Source: Long & Foster Broker Feed #MDAA2116724
ListingRemoved
$975,000

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

LGBTQ Local Legal Protections

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 1534 Circle Dr

  • What is 1534 Circle Dr estimated to be worth?
    Trulia's estimated value for 1534 Circle Dr in Annapolis, MD is $867,600.
  • What is the price history for 1534 Circle Dr?
    1534 Circle Dr in Annapolis, MD last sold for $860,000 in December 2025.
  • 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 1534 Circle Dr have air conditioning?
    Yes, 1534 Circle Dr in Annapolis, MD has air conditioning.
  • Does 1534 Circle Dr have a pool?
    Yes, 1534 Circle Dr in Annapolis, MD has a pool.

Explore by feature - Pet Friendly

93 pet-friendly rentals in Annapolis, MD

Explore by feature - Garage

24 rentals with a garage in Annapolis, MD

Explore by feature - Air Conditioning

138 rentals with air conditioning in Annapolis, MD

Explore by feature - Pool

57 rentals with a pool in Annapolis, MD

Explore by feature - Washer/dryer

152 rentals with a washer/dryer in Annapolis, MD

Explore by feature - Outdoor Space

29 rentals with an outdoor space in Annapolis, MD

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 1534 Circle Dr

Skip to last item
Skip to first item

Homes for sale near 1534 Circle Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item