101 Pine Dr, Annapolis, MD 21403
OFF MARKET

101 Pine Dr
Annapolis, MD 21403

  • 4 Beds
  • 3 Baths
  • 1,829 sqft (on 0.37 acres)

$665,200

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,778/mo*
Refinance Your Home

$665,200

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,778/mo*
Refinance Your Home
4 Beds
3 Baths
1,829 sqft
(on 0.37 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Stop the Car!! Enjoy this wonderful Coastal style home in the highly sought after, water-privileged community of Hillsmere Shores. All you need to do is Move-in! An Open Floor Plan, Gourmet Kitchen with Energy Star Stainless-Steel Appliances, a Wood-burning Fireplace in the Lower Level Family Room, a three-season sunroom for enjoying the gorgeous days and evenings. A fully fenced-in Huge Backyard with Patio for outdoor entertainment. And the dogs even have their own doggie run. Hillsmere Pool will be opening soon - memberships available. Or, head down to the beach or one of the marinas to cool off in the water; 2 boat ramps, or a short wait for a boat slip. It is an easy walk over to Quiet Water's Park, 340+ acre county park which hosts summer concerts, ice-skating, and festivals throughout the year. Feel like you are on vacation all the year-round!!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 101 Pine Dr

Interior Features

Interior Details
BasementTypes of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
DishwasherMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherDeckExterior: Brick
Parking & Garage
Parking Spaces: 4Parking: Off Street

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: split entry

Community

Units in Building: 1

Lot Information

Lot Area: 0.37 acres

Price History for 101 Pine Dr

DatePriceEventSource
08/03/2020$490,000Sold
N/A
06/15/2020$489,900PendingAgent Provided
06/10/2020$489,900Listed For SaleAgent Provided
07/25/2018$475,000Sold
N/A
06/16/2018$489,900PendingAgent Provided
05/19/2018$489,900Listed For SaleAgent Provided
01/01/2015$419,000Sold
Long & Foster Broker Feed #MDAA105632_100
04/08/2014$2,500ListingRemovedAgent Provided
03/03/2014$2,500Listed For RentAgent Provided
04/02/2013$2,300ListingRemovedAgent Provided
01/24/2013$2,300PriceChange
N/A
03/03/2012$2,600Listed For RentAgent Provided
01/07/2012$475,000ListingRemovedAgent Provided
01/06/2012$475,000Listed For SaleAgent Provided
07/16/2007$419,000Sold
N/A
04/06/2000$178,900Sold
N/A
02/03/1999$157,800Sold
N/A
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Property Tax and Assessment

Year2025
Tax$5,672
Assessment$473,967
Home facts updated by county records

Comparable Sales for 101 Pine Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
98 Pine Dr, Annapolis, MD
0.04
Single-Family Home
$570,000
12/02/25
3
1.5
1,734
404 Edgemere Dr, Annapolis, MD
0.16
Single-Family Home
$575,000
09/18/25
4
2.5
2,360
406 Edgemere Dr, Annapolis, MD
0.18
Single-Family Home
$585,000
12/01/25
4
2.5
2,200
115 Edgemere Dr, Annapolis, MD
0.17
Single-Family Home
$655,000
04/17/26
4
2
1,644
1008 Harbor Dr, Annapolis, MD
0.42
Single-Family Home
$545,000
09/26/25
4
2.5
1,956
298 Edgemere Dr, Annapolis, MD
0.12
Single-Family Home
$800,000
05/01/26
5
3
2,600
404 Beach Dr, Annapolis, MD
0.21
Single-Family Home
$665,000
07/10/25
3
3
1,976
909 Old Annapolis Neck Rd, Annapolis, MD
0.29
Single-Family Home
$680,000
08/29/25
3
2.5
2,088
920 Old Annapolis Neck Rd, Annapolis, MD
0.23
Single-Family Home
$710,000
02/27/26
4
2.5
2,552
503 Harbor Dr, Annapolis, MD
0.55
Single-Family Home
$529,000
04/10/26
3
3
1,920

Assigned Schools

These are the assigned schools for 101 Pine 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 467 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

  • 52 % Say they plan to stay for at least 5 years

  • 49 % Say there are community events

  • 48 % Say it's walkable to grocery stores

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
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  • 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
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  • 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
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  • 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
  • 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
    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
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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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101 Pine Dr, Annapolis, MD 21403 is a 4 bedroom, 3 bathroom, 1,829 sqft single-family home built in 1974. This property is not currently available for sale. 101 Pine Dr was last sold on Aug 3, 2020 for $490,000. The current Trulia Estimate for 101 Pine Dr is $665,200.