Back to Search
1244 Pine Ave, Shady Side, MD 20764
1244 Pine Ave, Shady Side, MD 20764
1244 Pine Ave, Shady Side, MD 20764
1244 Pine Ave, Shady Side, MD 20764
1244 Pine Ave, Shady Side, MD 20764
1244 Pine Ave, Shady Side, MD 20764
1244 Pine Ave, Shady Side, MD 20764

1244 Pine Ave Shady Side, MD 20764

0Views
0Saves

$749,900

ACTIVE
Beds
4
Baths
2
Sqft
2,674
Acres
0.34
Year
1950
Days on Site
1 Hour
Property Type
Residential
Sub Type
Per Square Foot
$280
Date Listed
Oct 8, 2026

Description of 1244 Pine Ave, Shady Side, MD 20764

Listing details for 1244 Pine Ave, Shady Side, MD 20764 : 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.
Listing Updated : 10-08-2026 at 4:04 PM EDT
Listing Provided By : Jennifer S Smira, 2022802060, [email protected], Compass
Source :

Bright MLS, MLS#: MDAA2158194

Open Houses

10
Sat, October
11:00 AM - 1:00 PM
For more information on this listing contact us at (202) 441-2348
Comments

Property History

DateEventPrice
10/8/2026
Listed for sale
$749,900 +90.8%
$280/sqft
Source:Bright MLS #MDAA2158194
9/29/2015
Sold
$393,000
$147/sqft
Source:Bright MLS #1001269345
3/31/2015
Listed for sale
—
Source:Bright MLS #1001269345
9/12/2014
Leased
$2,100
$1/sqft
Source:Bright MLS #1003187632
8/30/2014
Listed for Rent
—
Source:Bright MLS #1003187632
Home Worth Check

Interested in 1244 Pine Ave, Shady Side, MD 20764?

I agree to be contacted by Dell Residential Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. For more information, please review our Privacy Policy.

Location of 1244 Pine Ave, Shady Side, MD 20764

Streetview of 1244 Pine Ave, Shady Side, MD 20764

Mortgage Calculator
Listing Price
Down Payment
Interest Rate

Schools Near 1244 Pine Ave, Shady Side, MD 20764

For more information on this listing contact us at (202) 441-2348
Comments

Homes Similar to 1244 Pine Ave, Shady Side, MD 20764

Recent Blog Post By Category

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc.
HomeShady SideShady Side
For more information on this listing contact us at (202) 441-2348