1026 Pinecrest Dr, Annapolis, MD 21403
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Property image
OFF MARKET

1026 Pinecrest Dr
Annapolis, MD 21403

  • 3 Beds
  • 1.5 Baths
  • 2,160 sqft (on 0.28 acres)

$668,100

Trulia Estimate
as of Jul 29, 2026

$668,100

Trulia Estimate
as of Jul 29, 2026
3 Beds
1.5 Baths
2,160 sqft
(on 0.28 acres)

Local Information

  • Map ViewExplore the area around 1026 Pinecrest 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
1966
Lot Size
0.28 acres
Living Area
2,160 sqft
Price/Sqft
$309
Parking
3 Open Spaces

About this House

With offers in hand, please have your BEST AND FINAL offer in by 3:30 on Monday 6/3 to be considered. Welcome to this stunning and unique home in the desirable Annapolis Roads neighborhood. This beautiful residence boasts an abundance of outdoor private spaces perfect for enjoying nature, including a large fenced-in backyard and a screened-in porch ideal for relaxation and outdoor entertaining. The master bedroom features sliding glass doors leading to a Juliet balcony, offering a picturesque view of the front garden's dogwoods, holly trees, and azaleas. Two back bedrooms, with French doors opening to a private patio, provide a unique oasis where you can watch birds and enjoy the serene private backyard view. Shady trees keep the house cool in the summer while providing lush greenery year-round. Inside, the open-plan main floor centers around a beautiful brick fireplace with a woodstove insert, perfect for cozy winter nights. Custom-built bookshelves and cupboards add a touch of elegance and functionality. An open staircase with high ceilings and skylights brings in abundant sunlight and moonlight, enhancing the bright and airy feel of the home. The remodeled galley kitchen is a chef's delight, equipped with upgraded appliances, ample countertop space, and custom cabinetry featuring pull-out drawers. Did we mention that this homes interior has been freshly been painted and hardwood floors on the upper two levels just refinished. The recently refinished and waterproofed basement offers a large, well-lit space for entertaining, hobbies, and family fun, along with a spacious closet for additional storage. Discover the charm and tranquility of this unique home, where nature and comfort blend seamlessly. Schedule your tour today and experience all this property has to offer! Explore all the hidden amenities most of Annapolis has no clue that you exist in this great neighborhood. Enjoy the boat ramp, pier or pulling you paddleboard off the rack and paddling around Lake Ogleton after a long day at work. Take a quick stroll to the end of the road & sit by tidal wetlands just steps from the house. Don’t overlook the nature trails adjacent to the property or longer hikes that wind through the woods across Ogleton Road. Did I mention you get all this with NO HOA!
1026 Pinecrest Dr, Annapolis, MD 21403 is a 3 bedroom, 2 bathroom, 2,160 sqft single-family home built in 1966. It last sold for $620,000 on Jun 21, 2024 (7% above the $579,900 asking price). It is currently off market. The Trulia Estimate is $668,100, with a rent estimate of $3,502/month.

Home Details for 1026 Pinecrest Dr

Interior Features

Interior Details
Basement: Partially Finished,Connecting Stairway,PartialNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2160 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Forced Air,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Door: Sliding GlassFlooring: Hardwood, Carpet
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Hardwood, Carpet
View
Has a ViewView: Trees/Woods, Garden

Exterior Features

Exterior Home Features
Roof: Shake Asphalt ShinglePatio / Porch: Deck, Enclosed, Patio, Porch, ScreenedFencing: PartialOther Structures: Above Grade, Below GradeExterior: BalconyFoundation: BlockNo Private Pool
Parking & Garage
Number of Carport Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 3Has a CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Attached Carport,Driveway
Pool
Pool: None
Frontage
Waterfront: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming AllowedResponsible for Road Maintenance: City/CountyRoad Surface Type: Black TopNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Lake Ogleton / Severn River / Chesapeake Bay
Finished Area
Finished Area (above surface): 1728 Square FeetFinished Area (below surface): 432 Square Feet

Property Information

Year Built
Year Built: 1966Year Renovated: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary
Building
Construction Materials: Stick BuiltNot a New ConstructionNo Additional Parcels
Property Information
Condition: Excellent, Very Good, GoodParcel Number: 020200108559910

Price & Status

Price
List Price: $579,900
Status Change & Dates
Off Market Date: Fri Jun 21 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: ANNAPOLISCommunity: Annapolis Roads
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

Building

Building Area
Building Area: 2592 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.28 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDAA2083682Above Grade Unfinished Area: 1728
Last check for updates: about 2 hours ago
Listed by Justin Disborough, (410) 349-7871
Long & Foster Real Estate, Inc.
Bought with: Teresa Klem, (443) 223-1364, Long & Foster Real Estate, Inc.
Source: Bright MLS, MLS#MDAA2083682

Price History for 1026 Pinecrest Dr

DatePriceEventSource
06/21/2024$620,000Sold
Bright MLS #MDAA2083682
06/03/2024$579,900ContingentLong & Foster Broker Feed #MDAA2083682
05/31/2024$579,900Listed For SaleLong & Foster Broker Feed #MDAA2083682
06/20/2006$460,000Sold
N/A
02/11/2002$235,000Sold
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$6,142
Assessment$486,100
Home facts updated by county records

Comparable Sales for 1026 Pinecrest Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2845 Carrollton Rd, Annapolis, MD
0.13
Single-Family Home
$574,000
01/22/26
3
2
1,671
1009 Pinecrest Dr, Annapolis, MD
0.08
Single-Family Home
$725,000
11/05/25
4
3
2,426
1031 Old Bay Ridge Rd, Annapolis, MD
0.12
Single-Family Home
$739,000
03/13/26
4
3
2,296
1008 Harbor Dr, Annapolis, MD
0.11
Single-Family Home
$545,000
09/26/25
4
2.5
1,956
2648 Ogleton Rd, Annapolis, MD
0.30
Single-Family Home
$760,000
07/08/26
3
2.5
2,240
1003 Old Bay Ridge Rd, Annapolis, MD
0.10
Single-Family Home
$803,000
12/29/25
3
3.5
2,877
2664 Ogleton Rd, Annapolis, MD
0.16
Single-Family Home
$595,000
09/26/25
5
3
2,328
2701 Ogleton Rd, Annapolis, MD
0.13
Single-Family Home
$855,000
07/27/26
4
2.5
2,976
2642 Queen Anne Cir, Annapolis, MD
0.37
Single-Family Home
$849,000
05/15/26
3
2
2,980
1022 Harbor Dr, Annapolis, MD
0.13
Single-Family Home
$700,000
07/10/26
5
3
2,600

Nearby homes

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Assigned Schools

These are the assigned schools for 1026 Pinecrest 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
    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
  • 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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Homes for sale near 1026 Pinecrest Dr

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Off Market Homes Near 1026 Pinecrest 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