109 Pinecrest Dr, Annapolis, MD 21403
Property image
Property image
OFF MARKET

109 Pinecrest Dr
Annapolis, MD 21403

  • 3 Beds
  • 2 Baths
  • 1,652 sqft

$544,300

Trulia Estimate
as of Aug 21, 2026

$544,300

Trulia Estimate
as of Aug 21, 2026
  • 3 Beds
  • 2 Baths
  • 1,652 sqft

Home Highlights

Property Type
Single-Family Home
Living Area
1,652 sqft
Price/Sqft
$329

Local Information

  • Map ViewExplore the area around 109 Pinecrest Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Charming open concept FULLY FURNISHED bungalow in the water-privileged community of Hillsmere Shores. Available to rent for 3-6 month term.

ALL UTILITIES COVERED BY OWNER/INCLUDED IN RENT: internet, water, grass cutting (2x monthly), and pest control, BGE and Oil. **Smart TVs available in house for tenant to use their own log-in, but no cable tv is currently connected.

This vibrant neighborhood is located adjacent to the beautiful Quiet Waters Park and only minutes to historic Downtown Annapolis, with easy access to Routes 50 and 97 for effortless commuting. Dogs considered on a case by case basis.

Enjoy nature in the large fenced in backyard or on the screened in front porch. Open floor plan includes kitchen with recently upgraded stainless steel appliances (including gas range) and living room excellent for entertaining. 2 bedrooms (King + Queen) located on the primary level along with office space. Primary bathroom renovated in 2024, including walk in waterfall shower Secondary work and living space located on the lower level including a gym area, equipped with treadmill and free weights. 3rd bedroom located on lower level with separate entrance.

ALL UTILITIES COVERED BY OWNER/INCLUDED IN RENT: internet, water, grass cutting (2x monthly), and pest control, BGE and Oil.

**Smart TVs available in house for tenant to use their own log-in, but no cable tv is currently connected.
109 Pinecrest Dr, Annapolis, MD 21403 is a 3 bedroom, 2 bathroom, 1,652 sqft single-family home. It last sold for $345,000 on Dec 17, 2020 (8,979% above the $3,800 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $3,800 per month. That rental listing was removed on March 16, 2026. It is currently off market. The Trulia Estimate is $544,300, with a rent estimate of $3,618/month.

Home Details for 109 Pinecrest Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood
Room & Shared Space
Shared space is furnished

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 6 MonthAvailable: now

Exterior Features

Parking & Garage
Parking: Covered Off Street, On Site

Comparable Sales for 109 Pinecrest Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
117 Pinecrest Dr, Annapolis, MD
0.06
Single-Family Home
$445,000
03/06/26
4
3
1,160 sqft
406 Holly Dr, Annapolis, MD
0.21
Single-Family Home
$420,000
08/14/26
3
1.5
1,368 sqft
508 Harbor Dr, Annapolis, MD
0.13
Single-Family Home
$599,900
12/17/25
4
1.5
1,620 sqft
503 Harbor Dr, Annapolis, MD
0.12
Single-Family Home
$529,000
04/10/26
3
3
1,920 sqft
118 Groh Ln, Annapolis, MD
0.24
Single-Family Home
$508,280
12/05/25
3
1.5
1,344 sqft
84 Great Lake Dr, Annapolis, MD
0.19
Single-Family Home
$555,000
09/26/25
4
2
1,998 sqft
129 Pinecrest Dr, Annapolis, MD
0.20
Single-Family Home
$450,000
12/30/25
4
3
2,022 sqft
100 Carroll Dr, Annapolis, MD
0.21
Single-Family Home
$600,000
07/31/26
4
2
1,935 sqft
107 Spring Valley Dr, Annapolis, MD
0.18
Single-Family Home
$645,000
10/16/25
4
2
2,020 sqft
109 Great Lake Dr, Annapolis, MD
0.11
Single-Family Home
$650,000
05/26/26
4
3
1,836 sqft

Nearby homes

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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 peoplesā€™ 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
    "Itā€™s a very dog friendly place - I just canā€™t help wondering why some people donā€™t clean up after their pets? Itā€™s a nice neighborhood with high end properties & I donā€™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.
    "Iā€™m not sure, I donā€™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
    "Itā€™s a great neighborhood for kids and dogs Lots of walking areas, parks, water park and boat to downtown Annapolis "
    2
    Flag
  • Trulia User
    "Itā€™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 ā€œtouristā€ 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.. ā¤ļø "
    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 donā€™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
    "Weā€™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

Price and Tax history

DateEventPrice
Mar 16, 2026
Source: Zillow Rentals
ListingRemoved
$3,800
Mar 13, 2026
Source: Zillow Rentals
Listed For Rent
$3,800
Dec 24, 2025
Source: Zillow Rentals
ListingRemoved
$3,295
Dec 1, 2025
Source: Zillow Rentals
PriceChange
$3,295
Price decreased by 2%
Nov 3, 2025
Source: Zillow Rentals
Listed For Rent
$3,350

Frequently asked questions about 109 Pinecrest Dr

  • What is 109 Pinecrest Dr estimated to be worth?
    Trulia's estimated value for 109 Pinecrest Dr in Annapolis, MD is $544,300.
  • What is the price history for 109 Pinecrest Dr?
    109 Pinecrest Dr in Annapolis, MD last sold for $345,000 in December 2020.
  • 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 $646K. That is up $11.67K from the prior month.
  • Does 109 Pinecrest Dr have air conditioning?
    Yes, 109 Pinecrest Dr in Annapolis, MD has air conditioning.
  • Does 109 Pinecrest Dr have laundry facilities?
    Yes, 109 Pinecrest Dr in Annapolis, MD has in-unit laundry.

Homes for rent near 109 Pinecrest Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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