165 E Bay View Dr, Annapolis, MD 21403
Property image
Property image
OFF MARKET

165 E Bay View Dr
Annapolis, MD 21403

  • 3 Beds
  • 2.5 Baths
  • 1,950 sqft (on 0.32 acres)

$742,700

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $4,388/mo*
Refinance Your Home

$742,700

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $4,388/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,950 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 165 E Bay View 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
1958
Lot Size
0.32 acres
Living Area
1,950 sqft
Price/Sqft
$381

About this House

Welcome to your dream home in the highly sought-after community of Hillsmere Shores! This stunning 3 bedroom, 2.5 bath home boasts a contemporary split-level design with vaulted ceilings, top-of-the-line finishes, and a full renovation (both interior and exterior) that was completed in 2019. As soon as you step inside, you'll be greeted by a bright and airy living room with a cozy fireplace that creates a warm and inviting atmosphere. The gourmet kitchen is perfect for entertaining, featuring granite countertops, stainless steel appliances, and ample counter space. Upstairs, you'll find three spacious bedrooms that offer plenty of room for relaxation and privacy. The primary bedroom features a luxurious ensuite bathroom with a large vanity and a glass-enclosed shower. Downstairs, you'll find a completely finished space, perfect for a home office/gym/family room, with great light and a barn door for privacy Outside, the large, flat, private backyard is perfect for outdoor activities, entertaining guests, and simply enjoying the neighborhood's natural beauty. (There's even a water view during the winter!) You'll also have access to community amenities, including a pool, beach, playground, large marina, and several docks, making this the perfect home for enjoying the outdoors. The nearest boat and kayak/paddleboard launch is a short walk down the street (only 10 houses away), allowing for amazing adventures out on the water. Located just minutes from downtown Annapolis and Route 50, you'll enjoy easy access to a wide range of shopping, dining, and entertainment options. Whether you're commuting to work or exploring the charming streets of Annapolis, this home provides the perfect blend of luxury, comfort, and convenience. Don't miss out on this amazing opportunity to own your dream home in Hillsmere Shores! 2023-05-16
165 E Bay View Dr, Annapolis, MD 21403 is a 3 bedroom, 3 bathroom, 1,950 sqft single-family home built in 1958. It last sold for $665,000 on Jun 20, 2023. It is currently off market. The Trulia Estimate is $742,700, with a rent estimate of $3,569/month.

Home Details for 165 E Bay View Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
Microwave
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price History for 165 E Bay View Dr

DatePriceEventSource
06/20/2023$665,000Sold
Bright MLS #MDAA2058344
05/03/2023$650,000ContingentBright MLS #MDAA2058344
04/25/2023$650,000Listed For SaleBright MLS #MDAA2058344
03/24/2021ListingRemovedN/A
03/29/2019$492,500Sold
N/A
02/06/2019$515,000Listed For SaleN/A
06/06/2018$250,000Sold
N/A
05/30/2018$250,000PendingToActiveAgent Provided
05/03/2018$250,000PendingAgent Provided
04/30/2018$250,000Listed For SaleAgent Provided

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$6,121
Assessment$560,633
Home facts updated by county records

Comparable Sales for 165 E Bay View Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Huse Dr, Annapolis, MD
0.12
Single-Family Home
$825,000
03/18/26
3
2
2,060
110 Kuethe Dr, Annapolis, MD
0.08
Single-Family Home
$689,900
07/13/26
4
3.5
1,809
101 Huse Dr, Annapolis, MD
0.21
Single-Family Home
$785,000
04/30/26
4
2.5
2,016
150 E Bay View Dr, Annapolis, MD
0.13
Single-Family Home
$997,300
02/06/26
3
2
2,187
161 E Bay View Dr, Annapolis, MD
0.03
Single-Family Home
$925,000
01/09/26
4
3.5
3,142
84 Great Lake Dr, Annapolis, MD
0.23
Single-Family Home
$555,000
09/26/25
4
2
1,998
100 Carroll Dr, Annapolis, MD
0.27
Single-Family Home
$600,000
07/31/26
4
2
1,935
101 Lake View Dr, Annapolis, MD
0.34
Single-Family Home
$670,000
10/31/25
3
2
1,508
118 Groh Ln, Annapolis, MD
0.22
Single-Family Home
$508,280
12/05/25
3
1.5
1,344
107 Spring Valley Dr, Annapolis, MD
0.31
Single-Family Home
$645,000
10/16/25
4
2
2,020

Nearby homes

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Assigned Schools

These are the assigned schools for 165 E Bay View 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.
  • 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
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  • 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
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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 165 E Bay View Dr

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Off Market Homes Near 165 E Bay View Dr

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Frequently asked questions about 165 E Bay View Dr

  • What is 165 E Bay View Dr estimated to be worth?
    Trulia's estimated value for 165 E Bay View Dr in Annapolis, MD is $742,700.
  • What is the price history for 165 E Bay View Dr?
    165 E Bay View Dr in Annapolis, MD last sold for $665,000 in June 2023.
  • 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 $632K. That is up $6.37K from the prior month.
  • Does 165 E Bay View Dr have air conditioning?
    Yes, 165 E Bay View Dr in Annapolis, MD has air conditioning.
  • How big is the lot at 165 E Bay View Dr?
    The lot at 165 E Bay View Dr in Annapolis, MD is about 0.32 acres (14,000 sq ft).