958 Highpoint Dr, Annapolis, MD 21409
Property image
Property image
OFF MARKET

958 Highpoint Dr
Annapolis, MD 21409

  • 4 Beds
  • 2 Baths
  • 2,068 sqft

$571,400

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,384/mo*
Refinance Your Home

$571,400

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,384/mo*
Refinance Your Home
4 Beds
2 Baths
2,068 sqft

Home Value

Trulia Estimate
$571K
Since last month
Decreased$7K (-1.1%)
Since last year
Increased$12K (+2.1%)
Since last sale
Increased$170K (+42.6%)
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 +60% in the last 10 years
MonthEstimated value
2026
August 2026$570K
July 2026$577K
June 2026$592K
May 2026$581K
April 2026$577K
March 2026$574K
February 2026$564K
January 2026$557K
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
971 Saint Margarets Dr, Annapolis, MD
0.08
Single-Family Home
$415,000
02/19/26
3
2
1,983
970 Highpoint Dr, Annapolis, MD
0.11
Single-Family Home
$610,000
06/04/26
4
3
2,062
967 Highpoint Dr, Annapolis, MD
0.07
Single-Family Home
$555,000
03/12/26
4
3
1,588
1179 Neptune Pl, Annapolis, MD
0.17
Single-Family Home
$602,000
11/18/25
4
2.5
1,870
982 Highpoint Dr, Annapolis, MD
0.22
Single-Family Home
$555,000
03/18/26
4
3
2,190
1184 Neptune Pl, Annapolis, MD
0.22
Single-Family Home
$560,000
09/02/25
4
2.5
1,870
1207 Hampton Rd, Annapolis, MD
0.38
Single-Family Home
$562,500
05/01/26
4
2
2,412
1148 Mermaid Dr, Annapolis, MD
0.22
Single-Family Home
$664,900
04/29/26
4
2.5
1,870
1031 Lake Claire Dr, Annapolis, MD
0.30
Single-Family Home
$525,000
02/09/26
4
2
1,728
1227 Hampton Rd, Annapolis, MD
0.42
Single-Family Home
$585,000
10/31/25
4
2
2,068

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
970 Highpoint Dr, Annapolis, MD 21409
0.11
$610,000
4
3
2,062
Recently Sold
958 Mount Holly Dr, Annapolis, MD 21409
0.11
$612,800
3
2.5
2,224
Off Market
1199 Southview Dr, Annapolis, MD 21409
0.10
$570,200
4
2.5
2,100
Off Market
971 Saint Margarets Dr, Annapolis, MD 21409
0.08
$415,000
3
2
1,983
Recently Sold
975 Dogwood Tree Dr, Annapolis, MD 21409
0.15
$500,700
4
2
1,860
Off Market
966 Saint Margarets Dr, Annapolis, MD 21409
0.11
$491,300
4
1.5
1,490
Off Market
964 Saint Margarets Dr, Annapolis, MD 21409
0.11
$571,500
4
2
2,216
Off Market
1165 Neptune Pl, Annapolis, MD 21409
0.12
$790,500
5
3.5
3,424
Off Market
989 Saint Margarets Dr, Annapolis, MD 21409
0.16
$589,900
4
3
2,025
Off Market
1177 Southview Dr, Annapolis, MD 21409
0.13
$500,200
4
2.5
1,916
Off Market
1179 Neptune Pl, Annapolis, MD 21409
0.17
$602,000
4
2.5
1,870
Recently Sold
988 Saint Margarets Dr, Annapolis, MD 21409
0.20
$617,900
4
2
2,320
Off Market

Local Information

  • Map ViewExplore the area around 958 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
1974
Living Area
2,068 sqft
Price/Sqft
$276

About this House

Rare find in the Water Privileged Cape St. Clare. Just a short walk to the Marine/Beach life! Walk into a large open lower level, great for entertaining. Home features a main level bedroom with fully remodeled bath. Remodeled kitchen with new cabinets and granite counter tops, as well as a second remodeled bathroom. Roof was replaced just last year. Fenced rear yard with deck, driveway and off street parking . Located in a water oriented community with beach boat ramp, boat slips, clubhouse and much more!!!
958 Highpoint Dr, Annapolis, MD 21409 is a 4 bedroom, 2 bathroom, 2,068 sqft single-family home built in 1974. It last sold for $400,000 on Jul 27, 2020. It is currently off market. The Trulia Estimate is $571,400, with a rent estimate of $3,460/month.

Home Details for 958 Highpoint Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Types of Rooms: Dining Room
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 9000 sqft

Price and Tax history

DateEventPrice
Jul 27, 2020
Source: N/A
Sold
$400,000
Jun 1, 2020
Source: Agent Provided
Pending
$414,965
May 8, 2020
Source: Agent Provided
Listed For Sale
$414,965
Dec 16, 1997
Source: N/A
Sold
$129,000

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 958 Highpoint Dr

  • What is 958 Highpoint Dr estimated to be worth?
    Trulia's estimated value for 958 Highpoint Dr in Annapolis, MD is $571,400.
  • What is the price history for 958 Highpoint Dr?
    958 Highpoint Dr in Annapolis, MD last sold for $400,000 in July 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.
  • How big is the lot at 958 Highpoint Dr?
    The lot at 958 Highpoint Dr in Annapolis, MD is about 0.21 acres (9,000 sq ft).

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