8261 Bayside Dr, Pasadena, MD 21122
OFF MARKET

8261 Bayside Dr
Pasadena, MD 21122

  • 4 Beds
  • 3 Baths
  • 2,596 sqft

$1,309,400

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $7,500/mo*
Refinance Your Home

$1,309,400

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $7,500/mo*
Refinance Your Home
4 Beds
3 Baths
2,596 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Get the BIG BAY VIEWS you've been looking for! You have 2595 SF of living space with panoramic views of the Chesapeake Bay from every level and two full kitchens for a potential separate living area (think rental /ext. family). This is the perfect waterside retreat for family gatherings, recreation and relaxation. After a day of boating, fishing or shopping, you'll enjoy coming home to this calming view. The home was one of the original waterfront cottages built in the 1920's (tax record says 1948 because that is when the first tax record was recorded on the property) and is conveniently situated 20 miles from Annapolis, 30 miles from Baltimore, and less than 50 miles from Washington, D.C., making it perfect as a primary residence, second home or as an investment property. The current owners lovingly renovated and structurally reinforced the home while preserving its history. Improvements include waterproofing, vinyl siding, new roof, dual zoned A/C, finished lower level with an additional kitchen. With all this, the home still maintains touches of the original woodwork and expansive views of the Chesapeake from every level. This home has been loved through the generations and has been restored to be loved for many to come.

Arriving at the property, this residence stands out with its grey, coastal exterior, punctuated by a bright red door with the picturesque Chesapeake Bay as its backdrop. The front door opens to the second floor of this three-level home. Here, you'll find the first of two kitchens in the home with stainless steel appliances, dining room, living room, bedroom and full bathroom. A large year-round sunroom off the waterfront side of the home is the ideal place to serve drinks before dinner while taking in the commanding bay views as cargo and cruise ships pass by.

Upstairs, there are two comfortable bedrooms and a full bathroom. Open glass doors from the primary bedroom onto your balcony overlooking the Bay. Here you can enjoy morning coffee or yoga facing the magnificent sunrise while connecting with nature and watching the bald eagles, ospreys and many other water fowl. Evening entertainment or relaxation on the balcony features amazing views of the full moon rising across the bay. In the fall, you'll marvel at the migration of thousands of rare Canvasback ducks, who cover the water in the bay.

The lower level is fully equipped with a beautiful second kitchen, sitting area and bedroom,-both with large windows to take in the view, a full bathroom and large closets, creating a perfect space for a guest suite or for rental income. Open doors from this level onto the patio to enjoy the waterfront view or step onto the 90-foot dock to lower your boat from the lift and take it out onto the bay. The property also has a 20-foot fishing pier strategically located over the rocks, where fish hang out.

Even in the worst storms, the home never had water in it, but as a precaution, the current owner has completely waterproofed it. The home's Lower Level floor was raised 30 inches and on the bay side, the yard was re-graded to a higher elevation and gravity fed (no sump pump) French drains were installed around the foundation. In addition, the dock was rebuilt and raised to accommodate higher water levels. The elevated dock has survived the worst storms, while neighboring docks have not. The home does not require flood insurance.

This property's view s are expansive and you can see as far as the Bay Bridge. Downs Park is adjacent to the community and can be seen to the right of the property. There is also a private entrance so you and your furry family can enjoy the trails and beaches.

Additional inclusions are a security system on the home and detached shed, a remotely accessible video surveillance system, gas stoves in both kitchens, fresh paint throughout, a military grade computer router to prevent digital intrusion and a home warranty.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 8261 Bayside Dr

Interior Features

Interior Details
BasementTypes of Rooms: Walk In ClosetCeiling Fan
Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: VinylFoundation Type: Piers

Property Information

Year Built
Year Built: 1925
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 8261 Bayside Dr

DatePriceEventSource
05/12/2022$999,000Sold
Bright MLS #MDAA2025390
04/07/2022$999,000PendingLong & Foster Broker Feed #MDAA2025390
03/25/2022$999,000ContingentLong & Foster Broker Feed #MDAA2025390
03/25/2022$999,000PendingBright MLS #MDAA2025390
03/19/2022$999,000PriceChange
Bright MLS #MDAA2025390
09/16/2021$1,150,000Listed For SaleBright MLS #MDAA2009838
07/25/2011$537,500Sold
N/A

Market trends in Pasadena

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$427K
$1.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$256
$2MoM
Available listings
155
23MoM
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Property Tax and Assessment

Year2025
Tax$8,149
Assessment$694,600
Home facts updated by county records

Comparable Sales for 8261 Bayside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8227 Bayside Dr, Pasadena, MD
0.16
Single-Family Home
$1,100,000
10/02/25
4
3.5
3,430
2123 Beach Dr, Pasadena, MD
0.16
Single-Family Home
$829,900
03/30/26
5
2.5
4,230
8171 Bayside Dr, Pasadena, MD
0.41
Single-Family Home
$1,601,000
12/10/25
3
3
2,580
2164 Springdale Rd, Pasadena, MD
0.28
Single-Family Home
$536,000
04/09/26
3
1.5
1,040
8283 Choptank Rd, Pasadena, MD
0.61
Single-Family Home
$705,000
08/18/25
2
2
2,170
8293 Shilling Rd, Pasadena, MD
0.61
Single-Family Home
$670,000
08/15/25
3
3
2,388
1800 Chesapeake Pl, Pasadena, MD
0.89
Single-Family Home
$655,000
09/05/25
4
3
3,868
2023 Bay Rd, Pasadena, MD
1.33
Single-Family Home
$699,000
02/25/26
4
2.5
2,048
8292 Shilling Rd, Pasadena, MD
0.62
Single-Family Home
$410,000
04/16/26
3
2
1,790
86 Milburn Cir, Pasadena, MD
1.17
Single-Family Home
$650,000
08/22/25
4
3
3,225

Nearby homes

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Assigned Schools

These are the assigned schools for 8261 Bayside 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 Pasadena

At least 329 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 91 % Say it's dog friendly

  • 90 % Say yards are well-kept

  • 88 % Say parking is easy

  • 84 % Say there's holiday spirit

  • 73 % Say people would walk alone at night

  • 73 % Say kids play outside

  • 70 % Say it's quiet

  • 66 % Say there's wildlife

  • 59 % Say neighbors are friendly

  • 54 % Say they plan to stay for at least 5 years

  • 52 % Say streets are well-lit

  • 50 % Say there are sidewalks

  • 47 % Say it's walkable to grocery stores

  • 37 % Say it's walkable to restaurants

  • 36 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Mom
    "Public transportation is not common. Most transportation is with your personal vehicle. Roads are not crowded"
    0
    Flag
  • David Burns
    "Thier is really no place to walk your dog the roads are very busy and not safe to be walking and I really don’t want dogs doing Thier business on my lawn "
    0
    Flag
  • kimbriggsllc
    "The community comes together to support each other. There are yearly events like Halloween parties, block parties, and a carnival."
    0
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  • Rachelgracia
    "Lots of people walk their dogs in the neighborhood and clean up well. There are cleanup stations throughout the area with trash bags and a can to put it in. "
    0
    Flag
  • Trulia User
    "Most people here have dogs. And they walked their dog around and that’s how we meet and become friends with one another."
    0
    Flag
  • Trulia User
    "it's ok and would recommend it for some people but it's definitely not for everyone it's got its ups and downs like most crime ridden neighborhoods "
    0
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  • Trulia User
    "Lot’s of sidewalks and grassy areas throughout the subdivision. Plenty of other dogs to get their attention. There are doggie bag stations along the sidewalks."
    0
    Flag
  • Trulia User
    "This area has great access to the highway system and is close to Annapolis, Baltimore,DC and BWI airport and Hospitals."
    1
    Flag
  • Trulia User
    "Great neighbors, quiet neighborhood, and a lot of sidewalks for exercise. Also enjoy the pools and parks in the nicer months."
    0
    Flag
  • Trulia User
    "Pool Halloween gym park walking trails Close to the shopping centers movie night party ymca food Football basketball"
    0
    Flag
  • Trulia User
    "Very kid and pet friendly. Schools are just not great anymore. Plenty of confederate flags. Very racist county. Statistics can back this up, especially in the schools."
    9
    Flag
  • Trulia User
    "I love my home in Boulevard park. I love to walk the neighborhood . Lots of nature and water views. Great neighbors and friendly atmosphere."
    0
    Flag
  • Ajlouis2010
    "I've lived in this neighborhood since 2016. it's pet friendly, has walking trails, friendly neighbors, and quiet overall. "
    0
    Flag
  • Dawn B.
    "I live on a dead end street and love not having through traffic. Everyone here are very friendly. People take walks.. talk in the street. "
    0
    Flag
  • Dawn B.
    "There is traffic during rush hour to and from work. Ritchie highway is congested but so is Mountain rd. "
    0
    Flag
  • Snblake7
    "great access to everything you need within 10-15 mile radius. not too much traffic in Pasadena, safe area to run as well. "
    0
    Flag
  • Keenealthea
    "For the most part it's a nice area. I just happened to be in a not so nice part of Pasadena. I'm in the Freetown area of Pasadena and I feel like it's definitely time to go "
    0
    Flag
  • Robyn L.
    "Santa Run, community days in the park, small elementary school, Thanksgiving parade, local businesses "
    1
    Flag
  • 71bridges
    "Water-oriented community where everyone looks out for each other. Safe and family oriented. Convenient to lots of larger attractions "
    0
    Flag
  • Shelley H.
    "It’s about 30-35 minutes each day one way to Annapolis going either Ritchie Hwy or 97. Close to highways"
    0
    Flag
  • Eric T.
    "The HOA does nothing, complain about the little stuff and do nothing about the town homes that are falling apart and make the neighborhood look bad. "
    15
    Flag
  • Pldvorak1
    "It sucks. I travel 45-50 min each way 5 days a wk. I moved here before I changed jobs so there’s nothing I can do about it "
    0
    Flag
  • E_carreras
    "Water access. Family friendly. Broad range of homes from starter to multi million Enjoy the neighborhood "
    5
    Flag
  • Shrudolf1
    "There is a dog park at Downs park. It’s less than 15 minutes away. There are multiple pet stores and vet offices in the area. Most people walk their dogs and clean up after them. I would definitely recommend this area as a dog friendly area. "
    0
    Flag
  • Chandra B.
    "This is a great neighborhood where everyone watches out for everyone else. We love being next to the water and enjoying all the parks."
    0
    Flag
  • Msmith471
    "This area of Pasadena has become not so safe to live in. Drugs are all over the place and you never know what street is going to be affected. "
    0
    Flag
  • Masterken1989
    "It’s a decent area to start a family but I wouldn’t stay in green haven once the kids start school. Schools suck. lol "
    0
    Flag
  • Jlvavra0
    "Boating and Maryland crab culture is strong around here. A lot of people are into the marine life because we’re surrounded by the bay."
    0
    Flag
  • Shrudolf1
    "It’s a friendly community with lots to do. Most schools are brand new. Easily accessible to major highways. "
    0
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  • Chris p.
    "Lake shore is a good neighborhood, but there are no dog parks in the neighborhood. Also there is a lot of teenage kids roaming the neighborhood blasting inappropriate rap that has a lot of fowl language. I also don’t enjoy them shouting late at night when there are other people trying to sleep or relax, I walk around the neighborhood with my dog and smell drugs that these TEENAGE kids are smoking. Over all some parts of lake shore is good but not all"
    16
    Flag
  • anonymousmaryland
    "I often see dog owners walking their dogs. Downs Park has a very nice clean public dog beach. However, Pasadena lacks a public dog park but that’s okay."
    0
    Flag
  • anonymousmaryland
    "There are some great elementary schools, lovely churches, safe neighborhoods, Friendly Neighbors. There’s tons of things just a short drive away. Pasadena is a great place to raise a family."
    0
    Flag
  • Lorealmarie0408
    "dogs walking all the time. poop stations around neighborhood.........................................."
    1
    Flag
  • Erikmweber2002
    "Lakeshore is a very nice town that loves Christmas but lacks Sidewalks and needs more dog parks. Some stuff is in walking distance but otherwise you need a car to get around"
    8
    Flag
  • Ozark81259
    "We have community events for the children for all holidays. everyone gets involved in the festivities."
    4
    Flag

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8261 Bayside Dr, Pasadena, MD 21122 is a 4 bedroom, 3 bathroom, 2,596 sqft single-family home built in 1925. This property is not currently available for sale. 8261 Bayside Dr was last sold on May 12, 2022 for $999,000. The current Trulia Estimate for 8261 Bayside Dr is $1,309,400.