53 Fleet St, Annapolis, MD 21401
Property image
Property image
OFF MARKET

$849,900

Trulia Estimate
as of Sep 7, 2026
  • 2 Beds
  • 2 Baths
  • 996 sqft

53 Fleet St, Annapolis, MD 21401

Home Highlights

Single-Family Home
996 sqft
$853/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 53 Fleet St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Winter/spring monthly rental. This rental is for 2 separate roommates each with their own lease/ and shared home. There is a primary bedroom with bathroom ensuite for one tenant . The other bedroom has a bathroom in the hallway, for the second tenant. Shared use of kitchen and laundry. Available from Dec - March (possibly earlier and later if available). Only room for one car in the garage. If 2 total renters/leasees are not committed and found, this home will have to remain on the Airbnb listing.

Home with GARAGE PARKING & EV charger! Best location..walk to bottom of our street and you are at the docks...go to the top and you are on State Circle. Although this blue Carriage House is from the 1800's, you will love all the modern touches including EV,bluetooth speaker, smART TV, recessed lighting, newish kitchen appliances Nest thermostat and remodeled kitchen/bathrooms. Ranked in Annapolis' top 1% as guest favorite. Our Navy family welcomes you.
Pets considered.

No smoking or vaping indoors.
Pet fee is non refundable and used for deep cleaning.
Ev charger monthly fee is $100
No parking on the sidewalk please
first and last month rent required.
53 Fleet St, Annapolis, MD 21401 is a 2 bedroom, 2 bathroom, 996 sqft single-family home. It last sold for $740,000 on Oct 11, 2022 (32,074% above the $2,300 asking price). More recently, it was listed as a rental in April 2025 with an asking price of $2,300 per month. That rental listing was removed on April 19, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $849,900, with a rent estimate of $2,542/month.

Home Details for 53 Fleet St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 MonthAvailable: now

Exterior Features

Parking & Garage
GarageParking: Attached Garage, On Site

Comparable Sales for 53 Fleet St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
32 Cornhill St, Annapolis, MD
0.03
Single-Family Home
$750,000
08/31/26
2
1.5
1,064 sqft
45 Fleet St, Annapolis, MD
0.02
Single-Family Home
$810,000
08/18/26
2
1
864 sqft
76 East St, Annapolis, MD
0.03
Single-Family Home
$870,000
12/17/25
3
1.5
1,445 sqft
38 Cathedral St, Annapolis, MD
0.27
Single-Family Home
$684,000
06/03/26
2
1.5
900 sqft
167 Prince George St, Annapolis, MD
0.08
Single-Family Home
$865,000
04/03/26
2
2.5
1,590 sqft
54 Cornhill St, Annapolis, MD
0.03
Single-Family Home
$875,000
02/12/26
3
2
1,376 sqft
127 Charles St, Annapolis, MD
0.22
Single-Family Home
$750,000
07/16/26
3
1.5
1,360 sqft
212 King George St, Annapolis, MD
0.17
Single-Family Home
$500,000
12/12/25
1
2
1,008 sqft
199 Prince George St, Annapolis, MD
0.06
Single-Family Home
$834,750
10/29/25
3
3
1,770 sqft
115 Charles St, Annapolis, MD
0.24
Single-Family Home
$830,000
11/10/25
3
1.5
1,491 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Annapolis

Last updated Sep 2026
Trulia Rent Estimate$2,542/mo
Average rent
$2.57K
$8MoM
Available listings
176
View rental market trends in Annapolis, MD

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
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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
    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

Price and Tax history

DateEventPrice
Apr 19, 2025
Source: Zillow Rentals
ListingRemoved
$2,300
Apr 16, 2025
Source: Zillow Rentals
Listed For Rent
$2,300
Jun 13, 2024
Source: Zillow Rentals
ListingRemoved
May 23, 2024
Source: Zillow Rentals
Listed For Rent
$4,200
May 4, 2023
Source: Zillow Rentals
ListingRemoved

Frequently asked questions about 53 Fleet St

  • What is 53 Fleet St estimated to be worth?
    Trulia's estimated value for 53 Fleet St in Annapolis, MD is $849,900.
  • What is the price history for 53 Fleet St?
    53 Fleet St in Annapolis, MD last sold for $740,000 in October 2022.
  • 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 53 Fleet St have air conditioning?
    Yes, 53 Fleet St in Annapolis, MD has air conditioning.
  • Does 53 Fleet St have laundry facilities?
    Yes, 53 Fleet St in Annapolis, MD has in-unit laundry.

Homes for rent near 53 Fleet St

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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