533 2nd St, Annapolis, MD 21403
OFF MARKET

533 2nd St
Annapolis, MD 21403

  • 4 Beds
  • 3 Baths
  • 2,090 sqft

$1,676,400

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $9,485/mo*
Refinance Your Home

$1,676,400

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $9,485/mo*
Refinance Your Home
4 Beds
3 Baths
2,090 sqft

Local Information

  • Map ViewExplore the area around 533 2nd St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

EASTPORT! Still trying to wrap my mind around all of its features! Starting with private parking on a multi-car driveway coupled with a 2-car, over-sized Garage with access to the Mudroom -- well-planned and super convenient. This Coastal home is sited on a generous lot that has a fenced, rear yard with wonderful gardens and hardscaping. A grilling deck, plumbed for natural gas, and a spa (hot tub) are located just off the Sunroom that overlooks the backyard through floor-to-ceiling windows. Walking along the brick, paver walkways along each side of the house is where we'll find the front entry. You'll feel 'welcomed' from the moment you enter, greeted with light-filled and open spaces, high ceilings and hardwood floors. The Great Room is to the right and a main level Bedroom and full Bath, to the left. The Great Room has vaulted ceilings, a gas fireplace upon a raised hearth and wood mantel. An open floor plan thoughtfully incorporates the Dining area and Kitchen and the Sunroom mentioned earlier. You can't help but appreciate the well-organized spaces and abundance of cabinets and counters in the Kitchen. It boasts stainless steel appliances and a gas stove (also plumbed for electric, if that is your preference). A large Pantry rounds out this space. A main level full Bath offers convenience to the main level Bedroom and visiting guests. The upper level has a Primary Bedroom Suite, 2 additional Bedrooms, a full Bath with hand-stenciled lighthouses that run along the border -- it's a large Bathroom with double vanity, tub/shower combo and high ceilings. The Primary Bedroom Suite is well-lit with its vaulted ceilings. It has walk-in closets and a Primary Bath that is generous in size and amenities. At the top of the stairs, you'll want to stop briefly to appreciate the leaded, stained-glass window featuring a lighthouse scene with nautical flags that spell out a special message (be sure to brush up on your alpha/numeric signals ahead of time). The lower level is where we'll find the laundry and utility areas. The remaining space is open for you to finish as it suits you. A side entrance offers flexibility for access. And, of course, you're in Eastport with a walkability score that is off the charts and water all around you: Spa Creek, Back Creek and the Severn River. Then there's City Dock, the Naval Academy, and events like the Blue Angels and the annual Light Parade. Restaurants, shopping, the water taxi, and more make this a very special spot!
533 2nd St, Annapolis, MD 21403 is a 4 bedroom, 3 bathroom, 2,090 sqft single-family home built in 1990. It last sold for $1,300,000 on Mar 20, 2023. It is currently off market. The Trulia Estimate is $1,676,400, with a rent estimate of $4,086/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 533 2nd St

Interior Features

Interior Details
BasementCeiling Fan
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1990
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 5227 sqft

Price History for 533 2nd St

DatePriceEventSource
03/20/2023$1,300,000Sold
Bright MLS #MDAA2052822
02/17/2023$1,250,000PendingBright MLS #MDAA2052822
02/16/2023$1,250,000Listed For SaleBright MLS #MDAA2052822

Market trends in Annapolis

Last updated May 2026
Buyer'sMarketSeller'sMarket
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
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Property Tax and Assessment

Year2025
Tax$13,087
Assessment$1,109,867
Home facts updated by county records

Comparable Sales for 533 2nd St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
541 2nd St, Annapolis, MD
0.02
Single-Family Home
$1,470,000
10/31/25
4
3
2,341
417 Chesapeake Ave, Annapolis, MD
0.22
Single-Family Home
$1,380,000
06/26/26
3
2.5
2,259
215 Chester Ave, Annapolis, MD
0.07
Single-Family Home
$1,730,000
02/27/26
4
3.5
3,421
3 Chester Ave, Annapolis, MD
0.16
Single-Family Home
$1,660,000
02/12/26
3
3
2,815
544 2nd St, Annapolis, MD
0.03
Single-Family Home
$802,500
09/15/25
4
2
1,512
313 Chesapeake Ave, Annapolis, MD
0.13
Single-Family Home
$1,397,500
07/15/25
3
2
2,576
200 Chesapeake Ave, Annapolis, MD
0.10
Single-Family Home
$875,000
06/26/26
3
2.5
2,942
122 Chesapeake Ave, Annapolis, MD
0.09
Single-Family Home
$2,275,000
06/25/26
4
5
3,820
704 Severn Ave, Annapolis, MD
0.45
Single-Family Home
$944,000
07/01/25
3
3
2,060
712 Chesapeake Ave, Annapolis, MD
0.43
Single-Family Home
$1,600,000
06/03/26
4
2.5
3,280

Nearby homes

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Assigned Schools

These are the assigned schools for 533 2nd St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • 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
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  • 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
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  • 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
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  • 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
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  • 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
  • Bgonos7
    "A lot of space to walk and nearby parks. Nice area and everyone is dog friendly for the most part. A lot of Neighbors have dogs "
    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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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Homes for sale near 533 2nd St

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Off Market Homes Near 533 2nd St

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