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Roxana Kellam
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Office: (410) 561-0044
  • 1244 Pine Avenue , Shady Side, MD 20764 Main Photo

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New to the Market
BEDS4 BATHS2 full SQUARE FEET2,674 MLS#MDAA2158194
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONSHADY SIDE SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

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.

1244 Pine Avenue | MLS# MDAA2158194

This single family home located at 1244 Pine Avenue , Shady Side, MD 20764 is currently listed for sale with an asking price of $749,900. This property was built in 1950 and has 4 bedrooms and 2 full baths with 2674 sq. ft. Pine Avenue is located in the SHADY SIDE subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search SHADY SIDE real estate on roxanakellam.homesale.com today.

Upcoming Open Houses

Open House Saturday October 10th, 11:00am - 1:00pm

Property Features

Property Type: Residential - Single Family
Cooling: Central A/C
Fireplaces: 1
Fuel Type: Electric
Heating: Heat Pump(s)
Home Style: Contemporary
Lot Size: 0.34 Acres
Stories: 2.0
Taxes: $7,201
Year Built: 1950

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Disposal, Dryer, Microwave, Oven/Range - Gas, Refrigerator, Stove, Washer
Exterior: Vinyl Siding
Fencing: Rear
Fireplace: Mantel(s)
Flooring: Hardwood, Carpet
Interior: Combination Dining/Living, Built-Ins, Window Treatments, Entry Level Bedroom, Upgraded Countertops, Wood Floors, Floor Plan - Traditional
Lake Name: CHESAPEAKE BAY
Lot: Additional Lot(s), Partly Wooded
Lot Dimensions: 0.34 Acre(S)
Parking Features: Paved Driveway, Asphalt Driveway
Parking Notes: 2 Total Parking Spaces
Sewer: Public Sewer
Special View Info: Water, Bay
SQFT Above Finished: 2674
SQFT Total Finished: 2674
Structure Type: Detached
Total Garage/Parking Spaces: 2
Water: Public
Water Access: Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access
Windows: Bay/Bow, Double Pane
Wooded: Yes

Local Schools

School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Compass
Agency Phone: 2023866330

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Estimated Payment

$ 2,487.76 per month $1,668.95 Principal & Interest $600.08 Property Tax $218.72 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/09/2026. The listing information on this page last changed on 10/09/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 10/09/2026 12:03:55 AM EST) or Bright MLS (last updated Thu 10/08/2026 11:57:23 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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