163 Oak Dr, Annapolis, MD 21401
OFF MARKET

$2,757,000

Trulia Estimate
  • Studio
  • 2.5 Baths
  • 4,099 sqft (on 5.30 acres)

163 Oak Dr, Annapolis, MD 21401

Est. Refi. Payment $16,702/mo*
Refinance Your Home
Currently Off Market - Sold Dec 27, 2012 for $325,000

Home Value

Trulia Estimate
$2.76M
Since last month
Decreased$125K (-4.3%)
Since last year
Increased$139K (+5.3%)
Since last sale
Increased$2M (+746.6%)
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 +554% in the last 10 years
MonthEstimated value
2026
September 2026$2.75M
August 2026$2.73M
July 2026$2.88M
June 2026$2.76M
May 2026$2.74M
April 2026$2.71M
March 2026$2.66M
February 2026$2.62M
January 2026$2.6M
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
1840 Shore Dr, Annapolis, MD
0.06
Single-Family Home
$1,950,000
04/30/26
5
4
3,264
119 Kingswood Rd, Annapolis, MD
0.30
Single-Family Home
$1,100,000
06/02/26
4
3.5
3,560
2321 Hickory Rd, Annapolis, MD
0.17
Single-Family Home
$950,000
04/24/26
3
3
2,616
1870 Poplar Rd, Annapolis, MD
0.22
Single-Family Home
$870,000
07/17/26
4
3
2,941
1876 Severn Grove Rd, Annapolis, MD
0.28
Single-Family Home
$521,000
07/17/26
3
2.5
2,076
513 Epping Forest Rd, Annapolis, MD
0.47
Single-Family Home
$840,000
06/08/26
2
2,861
1870 Poplar Rd, Annapolis, MD
0.22
Single-Family Home
$870,000
07/24/26
4
3
1,866
1840 Kimberwicke Pl, Annapolis, MD
0.87
Single-Family Home
$925,000
02/13/26
5
2.5
2,958
1800 Severn Grove Rd, Annapolis, MD
0.48
Single-Family Home
$960,000
01/30/26
3
3
2,281
1930 Severn Grove Rd, Annapolis, MD
0.42
Single-Family Home
$557,000
03/31/26
3
2
1,911

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
1840 Shore Dr, Annapolis, MD 21401
0.06
$1,950,000
5
4
3,264
Recently Sold
1812 Shore Dr, Annapolis, MD 21401
0.14
$1,149,000
5
4
3,240
For Sale
2321 Hickory Rd, Annapolis, MD 21401
0.17
$950,000
3
3
2,616
Recently Sold
1870 Poplar Rd, Annapolis, MD 21401
0.22
$870,000
4
3
2,941
Recently Sold
110 Lancaster Ct, Annapolis, MD 21401
0.20
$939,400
4
3.5
3,120
Off Market
463 Hoenereng Trl, Annapolis, MD 21401
0.24
$2,122,200
4
3
2,605
Off Market
1876 Severn Grove Rd, Annapolis, MD 21401
0.28
$521,000
3
2.5
2,076
Recently Sold
1707 S Harbor Ln, Annapolis, MD 21401
0.26
$1,275,100
4
3.5
3,558
Off Market
2 Severn Dr, Annapolis, MD 21401
0.29
$473,700
2
1
1,216
Off Market
1705 S Harbor Ln, Annapolis, MD 21401
0.29
$1,146,300
4
3.5
3,135
Off Market
119 Kingswood Rd, Annapolis, MD 21401
0.30
$1,100,000
4
3.5
3,560
Recently Sold
1708 S Harbor Ln, Annapolis, MD 21401
0.31
$947,400
4
2
2,085
Off Market

Local Information

  • Map ViewExplore the area around 163 Oak Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2018
5.3 acre lot
4,099 sqft
$673/sqft
Garage

About this House

WATERFRONT Single-family Home (5.49 acres)
163 Oak Dr, Annapolis, MD 21401 is a studio, 3 bathroom, 4,099 sqft single-family home built in 2018. It last sold for $325,000 on Dec 27, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,757,000, with a rent estimate of $6,090/month.

Home Details for 163 Oak Dr

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, WorkshopCeiling Fan
Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood, Slate
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, MetalDeckExterior: Stone, Cement ConcreteGardenLawnPatioPorch
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 5.30 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Dec 27, 2012
Source: N/A
Sold
$325,000
Jun 2, 2012
Source: Agent Provided
Listed For Sale
$325,000
Sep 17, 2010
Source: Agent Provided
ListingRemoved
$825,000
Oct 25, 2009
Source: Agent Provided
Listed For Sale
$825,000
Jun 2, 2009
Source: Agent Provided
ListingRemoved
$825,000

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."
    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

LGBTQ Local Legal Protections

Frequently asked questions about 163 Oak Dr

  • What is 163 Oak Dr estimated to be worth?
    Trulia's estimated value for 163 Oak Dr in Annapolis, MD is $2,757,000.
  • What is the price history for 163 Oak Dr?
    163 Oak Dr in Annapolis, MD last sold for $325,000 in December 2012.
  • 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 163 Oak Dr have air conditioning?
    Yes, 163 Oak Dr in Annapolis, MD has air conditioning.
  • Does 163 Oak Dr have laundry facilities?
    Yes, 163 Oak Dr in Annapolis, MD has in-unit laundry.

Explore by feature - Pet Friendly

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