5 Dean St, Annapolis, MD 21401
Property image
Property image
OFF MARKET

$839,200

Trulia Estimate
as of Sep 8, 2026
  • 3 Beds
  • 2.5 Baths
  • 1,742 sqft

5 Dean St, Annapolis, MD 21401

Home Highlights

Townhouse
Built in 1910
1,742 sqft
$482/sqft

Local Information

  • Map ViewExplore the area around 5 Dean St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Spacious Downtown Annapolis Living | Historic 3BR Home w/ Modern Updates & Outdoor Living

Live in the heart of Annapolis on a quiet, tree-lined street just steps from downtown restaurants, shops, and the waterfront. This spacious 3-bedroom home on Dean Street offers the rare combination of historic charm, modern comfort, and unbeatable walkability.

Inside, you'll find a bright and inviting layout with generous living space, well-proportioned bedrooms, and thoughtful updates throughout. The home features high-end appliances, in-unit laundry, and a functional layout designed for both everyday living and entertaining.

Enjoy the convenience of being able to walk to everything downtown Annapolis has to offer dining, shopping, waterfront views, and local events while still coming home to a peaceful residential setting. A private outdoor space perfect for relaxing or entertaining adds to the appeal.

Additional highlights include:

 -Three generous bedrooms, including a primary suite with a California closet for boutique style organization
 -Two full baths + main level powder room, featuring premium finishes throughout
 -Spa inspired primary bath with an impressive 5x5 walk in shower
 -Gourmet kitchen equipped with a gas range, electric oven, and high end appliances perfect for home chefs
 -Brazilian hardwood floors that add warmth, richness, and durability to every room
 -Large, inviting front porch ideal for relaxing or greeting guests
 -Private outdoor space in the rear perfect for entertaining, grilling, or quiet evenings
 -Full size washer and dryer for everyday convenience
 -Smart code entry lock for secure, keyless access

This home is professionally maintained by a responsive local owner who takes pride in keeping the property in excellent condition. Pets will be considered on a case-by-case basis.

Homes in this location rarely become available don't miss the opportunity to enjoy downtown Annapolis living in a private, comfortable setting.

Lease term is for one year with no subletting. Tenant pays for water, electric, and cable.
5 Dean St, Annapolis, MD 21401 is a 3 bedroom, 3 bathroom, 1,742 sqft townhouse built in 1910. It last sold for $527,500 on Jan 1, 2015 (11,622% above the $4,500 asking price). More recently, it was listed as a rental in May 2026 with an asking price of $4,500 per month. That rental listing was removed on June 20, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $839,200, with a rent estimate of $4,214/month.

Home Details for 5 Dean St

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Townhouse

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DryerMicrowaveWasher
Heating & Cooling
Air ConditioningCooling System: Air Conditioner, Central Air, Ceiling Fan
Levels, Entrance, & Accessibility
Floors: Hardwood

Comparable Sales for 5 Dean St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 City Gate Ln, Annapolis, MD
0.05
Townhouse
$860,000
05/29/26
3
3.5
1,900 sqft
42 City Gate Ln, Annapolis, MD
0.08
Townhouse
$824,900
11/25/25
3
3
1,800 sqft
9 Dean St, Annapolis, MD
0.01
Townhouse
$1,250,000
07/24/26
3
3.5
1,857 sqft
102 South St, Annapolis, MD
0.13
Townhouse
$900,000
10/28/25
3
2.5
1,256 sqft
107 Charles St, Annapolis, MD
0.16
Townhouse
$870,000
10/23/25
3
2.5
1,364 sqft
79 Charles St, Annapolis, MD
0.15
Townhouse
$855,000
04/10/26
3
1.5
1,240 sqft
222 West St #E, Annapolis, MD
0.34
Townhouse
$625,000
10/30/25
3
2.5
1,434 sqft
57 Town Pines Ct, Annapolis, MD
0.17
Townhouse
$235,000
06/15/26
3
1.5
1,037 sqft
89 Southgate Ave, Annapolis, MD
0.34
Townhouse
$982,000
11/04/25
3
2.5
2,020 sqft
63 Town Pines Ct, Annapolis, MD
0.18
Townhouse
$215,000
10/08/25
3
1.5
1,037 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Rental Market Trends in Annapolis

Last updated Sep 2026
Trulia Rent Estimate$4,214/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 peoplesā€™ 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
    "Itā€™s a very dog friendly place - I just canā€™t help wondering why some people donā€™t clean up after their pets? Itā€™s a nice neighborhood with high end properties & I donā€™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.
    "Iā€™m not sure, I donā€™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
    "Itā€™s a great neighborhood for kids and dogs Lots of walking areas, parks, water park and boat to downtown Annapolis "
    2
    Flag
  • Trulia User
    "Itā€™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 ā€œtouristā€ 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.. ā¤ļø "
    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 donā€™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
    "Weā€™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
Jun 20, 2026
Source: Zillow Rentals
ListingRemoved
$4,500
May 7, 2026
Source: Zillow Rentals
Listed For Rent
$4,500
Apr 14, 2026
Source: Zillow Rentals
ListingRemoved
$4,500
Feb 26, 2026
Source: Zillow Rentals
Listed For Rent
$4,500
Jan 12, 2023
Source: Zillow Rentals
ListingRemoved

Frequently asked questions about 5 Dean St

  • What is 5 Dean St estimated to be worth?
    Trulia's estimated value for 5 Dean St in Annapolis, MD is $839,200.
  • What is the price history for 5 Dean St?
    5 Dean St in Annapolis, MD last sold for $527,500 in January 2015.
  • 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 5 Dean St have air conditioning?
    Yes, 5 Dean St in Annapolis, MD has air conditioning.
  • Does 5 Dean St have laundry facilities?
    Yes, 5 Dean St in Annapolis, MD has in-unit laundry.

Homes for rent near 5 Dean St

Skip to last item
Skip to first item

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