Is Annapolis, MD dog-friendly?

As of early 2026, 93% of users say it's dog friendly

Is a car needed in Annapolis, MD?

As of early 2026, 83% of users say car is needed

Does Annapolis, MD show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Is parking easy in Annapolis, MD?

As of early 2026, 73% of users say parking is easy

Does Annapolis, MD have sidewalks?

As of early 2026, 73% of users say there are sidewalks

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As of early 2026, 70% of users say yards are well-kept

Would people walk alone at night in Annapolis, MD?

As of early 2026, 68% of users say people would walk alone at night

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As of early 2026, 68% of users say kids play outside

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As of early 2026, 66% of users say streets are well-lit

Is Annapolis, MD quiet?

As of early 2026, 65% of users say it's quiet

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As of early 2026, 63% of users say there's wildlife

Is Annapolis, MD walkable to restaurants?

As of early 2026, 57% of users say it's walkable to restaurants

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As of early 2026, 57% of users say neighbors are friendly

Do residents of Annapolis, MD plan to stay at least 5 years?

As of early 2026, 51% of users say they plan to stay for at least 5 years

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As of early 2026, 49% of users say there are community events

Is Annapolis, MD walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

FOR SALE

OPEN FRI, 2-4PM

0.29 ACRES

100 Oak Dr
Annapolis, MD 21403

4 Beds
3 Baths
2,229 sqft (on 0.29 acres)

$845,000

Est. Mortgage $5,011/mo*

Get Pre-Qualified

$845,000

Est. Mortgage $5,011/mo*

Get Pre-Qualified

4 Beds

3 Baths

2,229 sqft

(on 0.29 acres)

Home Highlights

Parking

1 Car Garage

Climate Control

Heating & Cooling

HOA

$2/Monthly

Price/Sqft

$379

Listed

31 days ago

Local Information

Map ViewExplore the area around 100 Oak Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

OPEN HOUSE FRIDAY 8/7/26 2-4PM Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. Enjoy Hillsmere’s community amenities including private sandy beaches on the South River, a private marina with boat slips and direct access to the South River, boat ramps, waterfront pavilions, a community swimming pool, playgrounds, volleyball courts, and picnic areas. Whether you're boating, kayaking, fishing, or simply taking in the waterfront scenery, this community offers an unmatched coastal lifestyle. Conveniently located just minutes from historic downtown Annapolis, Quiet Waters Park, shopping, and dining, this exceptional home combines extensive recent updates with one of the area's most desirable waterfront communities. Don't miss the opportunity to make this beautifully renovated home your own.

Open House

Friday, August 07

2:00 PM to 4:00 PM

Home Details for 100 Oak Dr

Interior Features
Interior Details Basement: FinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths Number of Bedrooms: 4Main Level Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 2
Dimensions and Layout Living Area: 2229 Square Feet
Appliances & Utilities Appliances: Electric Water Heater
Heating & Cooling Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls Flooring: Ceramic Tile, Hardwood, Luxury Vinyl
Levels, Entrance, & Accessibility Stories: 2Levels: Multi/Split, TwoAccessibility: NoneFloors: Ceramic Tile, Hardwood, Luxury Vinyl
View No View

Exterior Features
Exterior Home Features Other Structures: Above Grade, Below GradeExterior: Private BeachFoundation: SlabNo Private Pool
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Other Parking: Garage Sqft: 352No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Faces Front,Attached,Driveway
Pool Pool: Community
Frontage Waterfront: RiverNot on Waterfront
Water & Sewer Sewer: Public SewerWater Body: South River
Finished Area Finished Area (above surface): 1314 Square FeetFinished Area (below surface): 915 Square Feet

Days on Market
Days on Market: 31

Property Information
Year Built Year Built: 1975
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Detached
Building Construction Materials: Brick, Vinyl SidingNot a New Construction
Property Information Condition: ExcellentParcel Number: 020241208020602

Price & Status
Price List Price: $845,000Price Per Sqft: $379
Status Change & Dates Possession Timing: Immediate

Active Status
MLS Status: ACTIVE

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

Agent Information
Listing Agent Listing ID: MDAA2149498

Building
Building Area Building Area: 2408 Square Feet

Community
Not Senior Community

HOA
HOA Name: HILLSMERE SHORES IMPROVEMENT ASSOCIATIONHas an HOAHOA Fee: $25/Annually

Lot Information
Lot Area: 0.29 acres

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Right To Sell

Business
Business Information Ownership: Fee Simple

Miscellaneous
BasementMls Number: MDAA2149498Above Grade Unfinished Area: 1314

Additional Information
Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Last check for updates: about 14 hours ago

Listing courtesy of Lauren Dorsey, (443) 775-7237

Innovative Properties, Inc., (410) 268-8400

Source: Bright MLS, MLS#MDAA2149498

Also Listed on Bright MLS.

Market trends in Annapolis

Last updated June 2026

Avg. sale price

$632K

$6.37KMoM

Sale-to-List Price

100.0%

Price per sq ft

$319

$6MoM

Available listings

357

21MoM

Price History for 100 Oak Dr

Date	Price	Event	Source
07/21/2026	$845,000	Listed For Sale	Bright MLS #MDAA2149498

04/22/2025	$3,750	ListingRemoved	Zillow Rentals

02/18/2025	$3,750	PriceChange	Zillow Rentals
Price Change $200 (-5%)
01/09/2025	$3,950	Listed For Rent	Zillow Rentals

12/10/2024	$570,000	Sold	Bright MLS #MDAA2094460
Recording Date 12/10/2024 County Transfer Tax N/A Total Transfer Tax N/A
12/03/2024	$585,000	Pending	Bright MLS #MDAA2094460

11/16/2024	$585,000	Contingent	Bright MLS #MDAA2094460

10/27/2024	$585,000	PriceChange	Bright MLS #MDAA2094460
Price Change $10,000 (-2%)
09/30/2024	$595,000	PriceChange	Bright MLS #MDAA2094460
Price Change $10,000 (-2%)
09/25/2024	$605,000	Listed For Sale	Bright MLS #MDAA2094460

04/01/2003	$285,000	Sold	N/A
Recording Date 04/01/2003 County Transfer Tax N/A Total Transfer Tax N/A
03/24/1998	$143,000	Sold	N/A
Recording Date 03/24/1998 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$5,500
Assessment	$430,767

Home facts updated by county records

Comparable Sales for 100 Oak Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
406 Edgemere Dr, Annapolis, MD	0.22	Single-Family Home	$585,000	12/01/25	4	2.5	2,200
404 Edgemere Dr, Annapolis, MD	0.22	Single-Family Home	$575,000	09/18/25	4	2.5	2,360
129 Meade Dr, Annapolis, MD	0.11	Single-Family Home	$585,000	07/01/26	4	2	1,679
121 Spruce Ln, Annapolis, MD	0.06	Single-Family Home	$901,000	01/16/26	4	3.5	3,222
403 Holly Dr, Annapolis, MD	0.10	Single-Family Home	$825,000	02/20/26	4	3	3,254
106 Pinecrest Dr, Annapolis, MD	0.25	Single-Family Home	$780,000	10/10/25	5	3	2,458
406 Harbor Dr, Annapolis, MD	0.25	Single-Family Home	$800,000	02/24/26	4	3	3,400
326 Cedar Ln, Annapolis, MD	0.24	Single-Family Home	$700,000	05/21/26	5	3	3,110
503 Harbor Dr, Annapolis, MD	0.31	Single-Family Home	$529,000	04/10/26	3	3	1,920

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Get a sense of prices in the area by checking nearby homes.

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RLAH @properties

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 100 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
Resident
8mo ago
"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
Resident
1y ago
"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
Resident
1y ago
"Safe. On water. Paths in woods. Friendly. Dog play area. Lots of open spaces. Areas are walkable, clean. "
0
Flag
Halljanie68
Resident
1y ago
"Community Pool convenient shopping. Easy access to major routes 50/95 Easy access to downtown Annapolis "
0
Flag
Sheila Wilson
Resident
1y ago
"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.
Resident
1y ago
"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
Resident
2y ago
"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
Resident
3y ago
"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
Resident
3y ago
"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
Prev. Resident
3y ago
"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
Resident
3y ago
"Great school public and private well maintained parks great public libraries close downtown Annapolis shopping for everything is conveniently close "
0
Flag
Trulia User
Resident
3y ago
"Lots of families with dogs. Poop bag stations throughout the neighborhood. Lots of woods to walk thru and sidewalks too. "
1
Flag
Trulia User
Resident
3y ago
"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
Resident
3y ago
"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
Resident
4y ago
"While Truxton is dog friendly it would be nice to have a dedicated dog park closer than Quiet Waters. "
0
Flag
Trulia User
Resident
4y ago
"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
Visitor
4y ago
"Good to walk. And parks are nice to play with kids. Stores are close by. And dog walkers all around. "
0
Flag
Trulia User
Resident
5y ago
"Summer beach parties, puppy happy hours, annual sock burning, lots of parks and the people are wonderful!"
0
Flag
Trulia User
Resident
5y ago
"the history Open napolis is amazing the people around here are kind and friendly and the schools are phenomenal"
0
Flag
Singletonad
Resident
5y ago
"the public school system in Annapolis needs to get significantly stronger overall. The private school system here is quite reliable."
0
Flag
Keren_molina
Resident
5y ago
"Lovely place and definitely good place to live and have a dog and a lot sores to go buy stuff ..........."
5
Flag
Singletonad
Resident
5y ago
"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
Resident
5y ago
"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
Resident
6y ago
" N/A school are great parking is great close to everything ppl are friendly and been living in Annapolis all my life "
4
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Tery_hodges
Resident
6y ago
"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
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Stephanie.ward0715
Resident
6y ago
"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
Resident
6y ago
"None that I know of. The community should definitely do more collaborative events at least at least Quarterly they are family friendly."
5
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Stella
Resident
6y ago
"Feel good living here Parking so easy Location very good Many things nearby Old town and new town "
3
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Jennifer B.
Resident
6y ago
"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
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Kwisniewski805
Resident
6y ago
"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.
Resident
6y ago
"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
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Beth S.
Resident
6y ago
"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.
Visitor
6y ago
"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
Resident
6y ago
"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
Visitor
7y ago
"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.
Resident
7y ago
"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
Resident
7y ago
"Local traffic is not too bad. Beach traffic and rush hour traffic to DC and Baltimore is pretty terrible. "
2
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Nadja Maril
Resident
7y ago
"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
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Markkimethanmolly
Resident
7y ago
"We’ve lived here for 18 years, and everyone is very friendly. Our neighborhood is very safe and quiet."
0
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Debwill64
Resident
7y ago
"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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LGBTQ Local Legal Protections

Lauren Dorsey, Innovative Properties, Inc., (410) 268-8400

Agent Phone: (443) 775-7237

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

100 Oak Dr, Annapolis, MD 21403 is a 4 bedroom, 3 bathroom, 2,229 sqft single-family home built in 1975. This property is currently available for sale and was listed by Bright MLS on Jul 21, 2026. The MLS # for this home is MLS# MDAA2149498.

100 Oak Dr Annapolis, MD 21403

$845,000

$845,000

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100 Oak Dr
Annapolis, MD 21403