Recently Listed Open House 10/10 11am - 1pm
1244 Pine Avenue
Shady Side, MD, 20764 $ 749,900
Bedrooms4 Baths2.0 Sq 2,674 Monthly Estimate*
$ 5,179
for $749,900 with 4 bedrooms and 2 full baths. This 2,674 square foot home was built in 1950 on a lot size of 0.34.
Welcome to 1244 Pine Avenue, a charming Chesapeake Bay waterfront retreat in Shady Side, Maryland, offering beautiful water and marina views, generous indoor-outdoor living, and a peaceful setting rooted in the boating lifestyle of southern Maryland The offering encompasses approximately 0.34 acres across Lots 16, 17, and 28, providing additional land and versatility rarely found in a waterfront community. Lots 16 and 17 are currently taxed together, while Lot 28 is separately deeded. Set within an established waterfront community, this inviting home offers the rare opportunity to enjoy everyday life just moments from the water, with a marina approximately one block (slips available for rent) away and a waterfront community center, playground, and picnic area nearby. Inside, the welcoming living and dining spaces are anchored by a fireplace and framed by picture windows that draw the surrounding water views into the home. The classic kitchen is thoughtfully appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range, creating a bright and functional space for everyday cooking and entertaining. Just beyond the kitchen, a screened-in porch extends the living space outdoors and provides an ideal setting for al fresco dining, morning coffee, or crisp fall evenings overlooking the peaceful surroundings. An expansive family room at the rear of the home offers additional space to gather and relax, with large windows capturing views toward the bay and sliding glass doors opening directly to the deck and backyard. A main-level bedroom adds valuable flexibility as a guest suite, home office, or additional living space. Upstairs, three generously proportioned bedrooms provide comfortable accommodations, including a spacious primary bedroom spanning one side of the home and offering lovely Chesapeake Bay views. Well appointed bathrooms throughout complete this turn-key home. Outside, the deck and yard create an effortless extension of the home, while a large storage shed provides additional functionality. Perfectly positioned in Shady Side, Maryland, 1244 Pine Avenue offers the relaxed character and natural beauty of Chesapeake Bay living with convenient access to the water, the nearby marina, Cedarhurst community amenities, and the surrounding towns of southern Anne Arundel County. Whether you're seeking a primary residence, weekend retreat, or a home that embraces the region's celebrated waterfront lifestyle, this distinctive property combines water views, flexible living space, multiple outdoor areas, and exceptional proximity head out on the Chesapeake Bay.
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Open House
10/10/2026 11:00 AM - 1:00 PM
1244 Pine Avenue Shady Side, MD
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralLiving Area 2674
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Central A/C
Possession Negotiable
Appliances Dishwasher Disposal Dryer Microwave Oven/Range - Gas Refrigerator Stove Washer
Zoning R5
Patio/Porch Features Deck(s) Porch(es) Screened
Architectural Style Contemporary
Construction Materials Vinyl Siding
School District ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Year Built 1950
View Water Bay
Levels 2
Tax Year 2026
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County ANNE ARUNDEL
New Construction N
Property Type Residential
HOA N
Subdivision Name SHADY SIDE
Garage Y/N N
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 2
Status ACTIVE
Directions Park Ave and Pine Ave Head toward Pine Ave Turn left onto Pine Ave Destination will be on the left 1244 Pine Ave
City SHADY SIDE
Body of Water CHESAPEAKE BAY
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 15000.10
Tax Annual Amount 7201.0
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 1
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 280.44
Acceptable Financing Cash Conventional FHA Negotiable VA
Vacation Rental Y/N N
Standard Status Active
Year Built Source Assessor
Legal Subdivision CEDARHURST ON THE BAY
Tax Lot 16
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InteriorInterior Amenities Combination Dining/Living Built-Ins Window Treatments Entry Level Bedroom Upgraded Countertops Wood Floors Floor Plan - Traditional
Heating Fuel Electric
Flooring Hardwood Carpet
Total Fireplaces 1
Fireplace Features Mantel(s)
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Window Features Bay/Bow Double Pane
Fireplace Y/N Y
Above Grade Finished Area 2674
Half Baths 0
Central Air Y/N Y
Total Bedrooms 4
Below Grade Finished Area 0
Main Level Bedrooms 1
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 2
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ExteriorPool No Pool
Fencing Rear
Parking Features Paved Driveway Asphalt Driveway
Lot Features Additional Lot(s) Partly Wooded
Water Source Public
Type of Parking Driveway
Foundation Details Other
Water View Y/N Y
Lot Size Acres 0.34
Water Body Type Bay
Lot Size Source Estimated
Waterfront Y/N N
Water Access Features Boat - Powered Canoe/Kayak Fishing Allowed Private Access
Number of Docks 0
Land Assessed Value 270500.00
Navigable Water Y/N Y
Water Oriented Y/N Y
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* Excluded FeaturesList Byjsmira@jennsmira.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $5,179
- Monthly Property Taxes
- $600
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Shady Side, MD
Average List Price $610,455
Percent of Sale Price 19%
About Shady Side, MD 5,765 Population
7% Since 2002
$ 91,856 Median Income
45 Median Age
27% Households with Children
Trends Information provided by ATTOM Data Solutions.
3533405 Elementary School
3533185 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/8/2026 | $749,900 | | Listed Price |