100 Oak Dr, Annapolis, MD 21403
Property image
Property image
FOR SALE
0.29 ACRES

$769,900

Original price: $799,000
  • 4 Beds
  • 3 Baths
  • 2,229 sqft (on 0.29 acres)

100 Oak Dr, Annapolis, MD 21403

Est. Mortgage $4,732/mo*
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Home Highlights

Single-Family Home
Built in 1975
0.29 acre lot
$345/sqft
1 Car Garage
HOA $2/mo

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

Price Improvement! 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.
Last check for updates: about 1 hour 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.

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: 78

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: $769,900Price Per Sqft: $345
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

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."
    1
    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

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

Home Value

Trulia Estimate
$755K
Since last month
Decreased$44K (-5.5%)
Since last year
Increased$72K (+10.6%)
Since last sale
Increased$185K (+32.5%)
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 +101% in the last 10 years
MonthEstimated value
2026
September 2026$755K
August 2026$800K
July 2026$840K
June 2026$652K
May 2026$701K
April 2026$695K
March 2026$695K
February 2026$678K
January 2026$690K
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
406 Edgemere Dr, Annapolis, MD
0.22
Single-Family Home
$585,000
12/01/25
4
2.5
2,200
318 Beach Dr, Annapolis, MD
0.21
Single-Family Home
$505,000
09/11/26
4
2.5
2,738
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

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
102 Oak Dr, Annapolis, MD 21403
0.02
$498,000
2
-
1,433
Recently Sold
104 Oak Dr, Annapolis, MD 21403
0.03
$640,800
3
2.5
1,600
Off Market
123 Spruce Ln, Annapolis, MD 21403
0.06
$850,000
4
3.5
3,615
Recently Sold
407 Beach Dr, Annapolis, MD 21403
0.09
$705,900
3
1.5
1,400
Off Market
121 Spruce Ln, Annapolis, MD 21403
0.06
$901,000
4
3.5
3,222
Recently Sold
124 Spruce Ln, Annapolis, MD 21403
0.09
$605,500
4
2
1,560
Off Market
404 Beach Dr, Annapolis, MD 21403
0.11
$676,700
3
3
1,976
Off Market
129 Meade Dr, Annapolis, MD 21403
0.11
$585,000
4
2
1,679
Recently Sold
462 Poplar Ln, Annapolis, MD 21403
0.13
$651,300
5
3
1,985
Off Market
403 Holly Dr, Annapolis, MD 21403
0.10
$825,000
4
3
3,254
Recently Sold
417 Holly Dr, Annapolis, MD 21403
0.10
$565,400
4
3
1,421
Off Market

Price and Tax history

DateEventPrice
Sep 17, 2026
Source: Zillow Rentals
ListingRemoved
$3,750
Sep 16, 2026
Source: Bright MLS #MDAA2149498
PriceChange
$769,900
Price increased by 20,431%
Sep 14, 2026
Source: Zillow Rentals
PriceChange
$3,750
Price decreased by 100%
Aug 31, 2026
Source: Bright MLS #MDAA2149498
PriceChange
$799,000
Price increased by 18,700%
Aug 24, 2026
Source: Zillow Rentals
Listed For Rent
$4,250

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

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Frequently asked questions about 100 Oak Dr

  • What is the estimated monthly payment for 100 Oak Dr?
    Based on a $769,900 list price with 20% down at today's rates, the estimated monthly payment for 100 Oak Dr in Annapolis, MD is approximately $4,781 (about $4,161 principal & interest, $545 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 100 Oak Dr compare to homes in Annapolis?
    100 Oak Dr in Annapolis, MD is listed at $769,900, about 20% above the $643K median sale price in Annapolis.
  • What do residents say about Annapolis?
    Residents describe Annapolis, MD as dog-friendly, easy to park in, and pedestrian-friendly. See homes for sale in Annapolis, MD.
  • What are the closest schools to 100 Oak Dr?
    The closest schools to 100 Oak Dr in Annapolis, MD are Annapolis High School (rated 4/10), Annapolis Middle School (rated 3/10), Hillsmere Elementary School (Pre-K, rated 10/10).
  • Does 100 Oak Dr have air conditioning?
    Yes, 100 Oak Dr in Annapolis, MD has air conditioning.
  • Does 100 Oak Dr have a pool?
    Yes, 100 Oak Dr in Annapolis, MD has a pool.
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.