104 Oak Dr, Annapolis, MD 21403
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Property image
OFF MARKET

104 Oak Dr
Annapolis, MD 21403

  • 3 Beds
  • 2.5 Baths
  • 1,600 sqft (on 0.38 acres)

$646,300

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $3,351/mo*
Refinance Your Home

$646,300

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $3,351/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,600 sqft
(on 0.38 acres)

Local Information

  • Map ViewExplore the area around 104 Oak Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1991
Lot Size
0.38 acres
Living Area
1,600 sqft
Price/Sqft
$404
Parking
5 Open Spaces
HOA
$2/Monthly

About this House

ROOF SCHEDULED FOR REPLACEMENT WITH 50-YEAR ARCHITECTURAL SHINGLE OCTOBER 17, 2024: WARRANTY FULLY TRANSFERABLE. Welcome home to the highly sought-after Hillsmere beach community! This carefully maintained split-level home with a basement, sits back on a corner lot, with a private fenced-in backyard. Upon entering the home, you are greeted by continuous wide-plank hardwood floors made of hickory (installed in 2018). The main level is an open-concept area containing a living room, dining area, and kitchen; decorated with modern light fixtures, crown-molding and chair-rail finishes. This provides a great space for entertaining guests while preparing your favorite meals. The gourmet kitchen includes quartz countertops, a marble backsplash, an island, recessed lighting, as well as stainless steel appliances (GE fridge purchased 2024). Heading up stairs you will find a full, newly-remodeled hall bathroom (2020) accompanied by two secondary bedrooms. The third, and primary bedroom, contains crown molding and an ensuite bathroom (updated in 2023). Heading downstairs from the main level, you arrive first at the family room. Attached you’ll find a laundry/auxiliary room “outfitted” with plenty of cabinetry to use however you find fit, which also leads to a half bath on this level. The house conveys a clothes washer and a clothes dryer by LG that was replaced in 2024. Heading further downstairs from the family room, you will find a spacious basement that, though it’s unfinished, provides great storage space for seasonal items and hobbies! On this level you will find most of your utilities including a newly updated water treatment system (replaced late 2023). The outdoor spaces on this property are accented by beautiful mature trees that provide privacy as well as shade. The charming backyard space contains a covered deck leading to a hardscape patio with a firepit. The play set is included with the property as well as a shed for additional storage. The property is accessed by a long asphalt driveway that widens as you near the home and provides ample parking (repaved in 2018). The neighborhood has a community pool you can become a member of as well as a marina. There is a neighborhood beach/playground, storage for kayaks or paddle-boards; and even several dog-parks. Quiet Water Park meets the entrance of the neighborhood and the rest of the beautiful city of Annapolis is just around the corner! Please join us for our OPEN HOUSE 10/13 from 11am - 3pm.
104 Oak Dr, Annapolis, MD 21403 is a 3 bedroom, 3 bathroom, 1,600 sqft single-family home built in 1991. It last sold for $615,000 on Nov 14, 2024 (3% above the $594,900 asking price). It is currently off market. The Trulia Estimate is $646,300, with a rent estimate of $4,013/month.

Home Details for 104 Oak Dr

Interior Features

Interior Details
Basement: Other,Interior Entry,Exterior Entry,Unfinished,Walk-Out AccessNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1600 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Phone Available, Water Available, BroadbandAppliances: Dishwasher, Dryer, ENERGY STAR Qualified Washer, Ice Maker, Microwave, Oven/Range - Electric, Washer, Water Conditioner - Owned, Water Heater, Electric Water HeaterDishwasherDryerLaundry: Has Laundry,Washer In Unit,Lower Level,Washer/Dryer Hookups OnlyMicrowaveWasher
Heating & Cooling
Heating: Heat Pump,OilHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Insulated Windows, Window TreatmentsDoor: InsulatedFlooring: Engineered Wood, Hardwood, Carpet, Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: Multi/Split, TwoAccessibility: 2+ Access ExitsFloors: Engineered Wood, Hardwood, Carpet, Ceramic Tile, Wood
View
Has a ViewView: Garden, Trees/Woods, Street

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Deck, PatioFencing: Decorative, Back YardOther Structures: Above Grade, Below GradeExterior: Extensive Hardscape, Rain Gutters, Play Equipment, SidewalksFoundation: Block, SlabNo Private Pool
Parking & Garage
Open Parking Spaces: 5No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 5Parking: Asphalt,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1600 Square Feet

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Detached
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Condition: Excellent, Very Good, GoodParcel Number: 020241209593600

Price & Status

Price
List Price: $594,900
Status Change & Dates
Off Market Date: Thu Nov 14 2024Possession Timing: Negotiable

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: ANNAPOLISCommunity: Hillsmere Estates
School Information
Elementary School: HillsmereElementary School District: Anne Arundel County Public SchoolsJr High / Middle School: AnnapolisJr High / Middle School District: Anne Arundel County Public SchoolsHigh School: AnnapolisHigh School District: Anne Arundel County Public Schools

Building

Building Area
Building Area: 2120 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Maintenance Grounds, Road Maintenance, Pier/Dock MaintenanceHOA Name: HILLSMERE SHORES IMPROVEMENT ASSOCIATIONHas an HOAHOA Fee: $25/Annually

Lot Information

Lot Area: 0.38 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: AppraisalListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, Negotiable, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2096312Above Grade Unfinished Area: 1600

Additional Information

HOA Amenities: Baseball Field,Beach Access,Boat Dock/Slip,Boat Ramp,Common Grounds,Marina/Marina Club,Picnic Area,Pier/Dock,Pool,Pool Mem Avail,Tot Lots/Playground
Last check for updates: about 1 hour ago
Listed by Matt Hinshaw, (301) 643-7741
Five Star Real Estate
Bought with: Matthew Carcone, (202) 683-6097, Gordon James Brokerage
Source: Bright MLS, MLS#MDAA2096312

Price History for 104 Oak Dr

DatePriceEventSource
11/14/2024$615,000Sold
Bright MLS #MDAA2096312
10/14/2024$594,900ContingentBright MLS #MDAA2096312
10/10/2024$594,900Listed For SaleBright MLS #MDAA2096312
03/16/2017$358,000Sold
N/A
11/20/2012$369,000Sold
N/A
08/31/2012$379,000Listed For SaleAgent Provided
05/12/1997$22,500Sold
N/A

Market trends in Annapolis

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$632K
$6.37KMoM
Sale-to-List Price
100.0%
Price per sq ft
$319
$6MoM
Available listings
357
21MoM
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Property Tax and Assessment

Year2025
Tax$5,759
Assessment$454,500
Home facts updated by county records

Comparable Sales for 104 Oak Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
129 Meade Dr, Annapolis, MD
0.13
Single-Family Home
$585,000
07/01/26
4
2
1,679
98 Pine Dr, Annapolis, MD
0.29
Single-Family Home
$570,000
12/02/25
3
1.5
1,734
503 Harbor Dr, Annapolis, MD
0.34
Single-Family Home
$529,000
04/10/26
3
3
1,920
406 Edgemere Dr, Annapolis, MD
0.19
Single-Family Home
$585,000
12/01/25
4
2.5
2,200
404 Edgemere Dr, Annapolis, MD
0.19
Single-Family Home
$575,000
09/18/25
4
2.5
2,360
503 Beach Dr, Annapolis, MD
0.15
Single-Family Home
$498,000
08/04/25
3
1
1,362
115 Edgemere Dr, Annapolis, MD
0.44
Single-Family Home
$655,000
04/17/26
4
2
1,644
3109 Ervin Ct, Annapolis, MD
0.30
Single-Family Home
$785,000
02/21/26
2
2.5
1,801
508 Harbor Dr, Annapolis, MD
0.41
Single-Family Home
$599,900
12/17/25
4
1.5
1,620

Nearby homes

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Assigned Schools

These are the assigned schools for 104 Oak Dr.
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 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.
  • 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
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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
    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
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  • 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
    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
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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
    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

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Homes for sale near 104 Oak Dr

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Off Market Homes Near 104 Oak Dr

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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