1199 Highview Dr, Annapolis, MD 21409
Property image
Property image
OFF MARKET

$576,900

Trulia Estimate
as of Sep 3, 2026
  • 1 Bed
  • 1 Bath
  • 1,000 sqft
  • 1 Bed
  • 1 Bath
  • 1,000 sqft

1199 Highview Dr, Annapolis, MD 21409

Home Highlights

Property Type
Single-Family Home
Living Area
1,000 sqft
Price/Sqft
$577

Local Information

  • Map ViewExplore the area around 1199 Highview Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Seeking an individual, couple or family to share a home in Cape St. Claire, Annapolis, MD. The home is equipped with a sunroom, deck, shed, fenced in backyard, hot tub, level 2 EV charger, and water privileges. The primary rental area, which comes furnished or unfurnished, consists of the entire lower level with a large bedroom with two walk-in closets, a full bathroom with a walk-in shower, kitchenette, office/den area, family room and a private washer and dryer on the lower level of a split-foyer home. The rental area also has a private entrance. Pets are welcome; however, smoking is not permitted on the property.

Monthly rent includes Wi-Fi, water, home security system, oil and electric.
1199 Highview Dr, Annapolis, MD 21409 is a 1 bedroom, 1 bathroom, 1,000 sqft single-family home. It last sold for $450,000 on Oct 22, 2020 (32,043% above the $1,400 asking price). More recently, it was listed as a rental in November 2022 with an asking price of $2,800 per month. That rental listing was removed on December 3, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $576,900, with a rent estimate of $1,797/month.

Home Details for 1199 Highview Dr

Interior Features

Heating & Cooling
Heating: Central, Heat PumpAir ConditioningCooling System: Air Conditioner, Central AirHeating Fuel: Central
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Room & Shared Space
Room is furnishedHas private bath

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 MonthAvailable: nowUtilities Share: Included in rent payments

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 1199 Highview Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1258 Cape Saint Claire Rd, Annapolis, MD
0.30
Single-Family Home
$430,000
04/03/26
3
1
952 sqft
1033 Saint Margarets Dr, Annapolis, MD
0.16
Single-Family Home
$420,000
02/13/26
3
2
990 sqft
1023 Mountain Top Dr, Annapolis, MD
0.07
Single-Family Home
$415,000
01/23/26
4
2
1,404 sqft
1044 Skyview Dr, Annapolis, MD
0.10
Single-Family Home
$504,000
12/03/25
3
2
1,828 sqft
1052 Lido Dr, Annapolis, MD
0.20
Single-Family Home
$515,000
06/29/26
4
1.5
1,488 sqft
1148 Riverview Dr, Annapolis, MD
0.28
Single-Family Home
$525,000
04/08/26
3
2
1,460 sqft
1095 Skyway Dr, Annapolis, MD
0.37
Single-Family Home
$425,000
11/26/25
3
2
1,196 sqft
1126 Skyway Dr, Annapolis, MD
0.22
Single-Family Home
$500,000
09/22/25
4
2
1,623 sqft
1155 Pine Tree Dr, Annapolis, MD
0.41
Single-Family Home
$438,000
12/15/25
3
2
1,228 sqft
1045 Saint Margarets Dr, Annapolis, MD
0.24
Single-Family Home
$525,000
04/15/26
4
2
1,678 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Annapolis

Last updated Sep 2026
Trulia Rent Estimate$1,797/mo
Average rent
$2.57K
$8MoM
Available listings
176
View rental market trends in Annapolis, MD

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
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  • 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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Dec 3, 2022
Source: Zillow Rental Manager
ListingRemoved
Nov 27, 2022
Source: Zillow Rental Manager
Listed For Rent
$2,800
Oct 22, 2020
Source: N/A
Sold
$450,000
Sep 29, 2020
Source: Agent Provided
Pending
$450,000
Sep 29, 2020
Source: Agent Provided
PriceChange
$450,000
Price increased by 3%

Frequently asked questions about 1199 Highview Dr

  • What is 1199 Highview Dr estimated to be worth?
    Trulia's estimated value for 1199 Highview Dr in Annapolis, MD is $576,900.
  • What is the price history for 1199 Highview Dr?
    1199 Highview Dr in Annapolis, MD last sold for $450,000 in October 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 1199 Highview Dr have air conditioning?
    Yes, 1199 Highview Dr in Annapolis, MD has air conditioning.
  • Does 1199 Highview Dr have laundry facilities?
    Yes, 1199 Highview Dr in Annapolis, MD has in-unit laundry.

Homes for rent near 1199 Highview 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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