989 Highpoint Dr, Annapolis, MD 21409
Upstairs hall
Second bedroom
OFF MARKET

989 Highpoint Dr
Annapolis, MD 21409

  • 4 Beds
  • 2.5 Baths
  • 1,450 sqft

$519,400

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $3,091/mo*
Refinance Your Home

$519,400

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $3,091/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,450 sqft

Home Value

Trulia Estimate
$519K
Since last month
Decreased$8K (-1.5%)
Since last year
Increased$15K (+2.9%)
Since last sale
Increased$164K (+46.1%)
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 +48% in the last 10 years
MonthEstimated value
2026
August 2026$519K
July 2026$527K
June 2026$534K
May 2026$531K
April 2026$525K
March 2026$521K
February 2026$511K
January 2026$505K
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
982 Highpoint Dr, Annapolis, MD
0.04
Single-Family Home
$555,000
03/18/26
4
3
2,190
967 Highpoint Dr, Annapolis, MD
0.18
Single-Family Home
$555,000
03/12/26
4
3
1,588
1180 Saint George Dr, Annapolis, MD
0.17
Single-Family Home
$585,000
09/12/25
4
3
1,844
970 Highpoint Dr, Annapolis, MD
0.14
Single-Family Home
$610,000
06/04/26
4
3
2,062
990 Highpoint Dr, Annapolis, MD
0.04
Single-Family Home
$595,000
08/25/25
3
3
2,472
1207 Hampton Rd, Annapolis, MD
0.15
Single-Family Home
$562,500
05/01/26
4
2
2,412
1162 Saint George Dr, Annapolis, MD
0.25
Single-Family Home
$530,000
03/31/26
4
2
1,643
1015 Mount Holly Dr, Annapolis, MD
0.23
Single-Family Home
$675,000
02/13/26
4
3
1,680
1041 Skyview Dr, Annapolis, MD
0.23
Single-Family Home
$579,500
05/06/26
4
3
1,960
1023 Mountain Top Dr, Annapolis, MD
0.35
Single-Family Home
$415,000
01/23/26
4
2
1,404

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
982 Highpoint Dr, Annapolis, MD 21409
0.04
$555,000
4
3
2,190
Recently Sold
990 Highpoint Dr, Annapolis, MD 21409
0.04
$604,900
3
3
2,472
Off Market
987 Saint Johns Dr, Annapolis, MD 21409
0.06
$892,300
4
2.5
2,740
Off Market
989 Saint Johns Dr, Annapolis, MD 21409
0.07
$1,061,600
4
2.5
2,580
Off Market
989 Dogwood Tree Dr, Annapolis, MD 21409
0.05
$484,800
3
2
1,612
Off Market
1005 Saint Margarets Dr, Annapolis, MD 21409
0.11
$627,000
4
3
2,050
Off Market
1192 Hampton Rd, Annapolis, MD 21409
0.09
$552,600
4
2.5
1,356
Off Market
1009 Saint Margarets Dr, Annapolis, MD 21409
0.12
$681,200
3
3.5
2,475
Off Market
970 Highpoint Dr, Annapolis, MD 21409
0.14
$610,000
4
3
2,062
Recently Sold
975 Dogwood Tree Dr, Annapolis, MD 21409
0.14
$500,700
4
2
1,860
Off Market
989 Saint Margarets Dr, Annapolis, MD 21409
0.15
$589,900
4
3
2,025
Off Market
988 Saint Margarets Dr, Annapolis, MD 21409
0.16
$617,900
4
2
2,320
Off Market

Local Information

  • Map ViewExplore the area around 989 Highpoint 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
1969
Living Area
1,450 sqft
Price/Sqft
$358
Parking
Garage

About this House

This single-family home is located at 989 Highpoint Dr, Annapolis, MD. 989 Highpoint Dr is in Annapolis, MD and in ZIP code 21409. This property has 4 bedrooms, 3 bathrooms and approximately 1,450 sqft of floor space. This property has a lot size of 8999 sqft and was built in 1969.
989 Highpoint Dr, Annapolis, MD 21409 is a 4 bedroom, 3 bathroom, 1,450 sqft single-family home built in 1969. It last sold for $355,500 on Sep 20, 2019. It is currently off market. The Trulia Estimate is $519,400, with a rent estimate of $3,001/month.

Home Details for 989 Highpoint Dr

Interior Features

Interior Details
BasementCeiling Fan
Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Vinyl, Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: split entry

Building

Levels, Entrance, & Accessibility
Disabled Access

Community

Units in Building: 1

Lot Information

Lot Area: 8999 sqft

Price and Tax history

DateEventPrice
Sep 20, 2019
Source: N/A
Sold
$355,500
Aug 24, 2019
Source: Agent Provided
PriceChange
$357,000
Price increased by 2%
Aug 13, 2019
Source: Agent Provided
Pending
$349,500
Aug 7, 2019
Source: Agent Provided
PriceChange
$349,500
Price decreased by 2%
Jul 13, 2019
Source: Agent Provided
PriceChange
$355,000
Price decreased by 3%

Market trends in Annapolis

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$646K
$11.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$326
$7MoM
Available listings
355
3MoM

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."
    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
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 989 Highpoint Dr

  • What is 989 Highpoint Dr estimated to be worth?
    Trulia's estimated value for 989 Highpoint Dr in Annapolis, MD is $519,400.
  • What is the price history for 989 Highpoint Dr?
    989 Highpoint Dr in Annapolis, MD last sold for $355,500 in September 2019.
  • 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 989 Highpoint Dr have air conditioning?
    Yes, 989 Highpoint Dr in Annapolis, MD has air conditioning.
  • Does 989 Highpoint Dr have laundry facilities?
    Yes, 989 Highpoint Dr in Annapolis, MD has in-unit laundry.

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