For Sale
Single family home for sale at 1244 Pine Ave, Shady Side, MD 20764 | MLS# MDAA2158194 | Listing updated on 2026-10-08
Photo 1 of Single family home for sale at 1244 Pine Ave, Shady Side, MD 20764 | MLS# MDAA2158194 | Listing updated on 2026-10-08
Photo 2 of Single family home for sale at 1244 Pine Ave, Shady Side, MD 20764 | MLS# MDAA2158194 | Listing updated on 2026-10-08
Photo 3 of Single family home for sale at 1244 Pine Ave, Shady Side, MD 20764 | MLS# MDAA2158194 | Listing updated on 2026-10-08
Photo 4 of Single family home for sale at 1244 Pine Ave, Shady Side, MD 20764 | MLS# MDAA2158194 | Listing updated on 2026-10-08
53+
Beds Icon

Street View

$749,900

Monthly Est:$3,733

  • Beds Icon4 Beds
  • Beds Icon
    2 Baths
  • Beds Icon2,674sqft

1244 Pine Ave, Shady Side, MD 20764

$3,733/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1950

  • $-- HOA

  • 15,000.1 sqft lot

  • $280/sq.ft

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 (sli
ps 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.

  • Houzeo last checked: 1 hour ago
  • Listing updated: October 8, 2026 at 7:14 pm
  • Listing Provided by: Jennifer S Smira (202) 280-2060 | Compass (202) 386-6330
  • Source: Bright MLS-NJ | MLS#: MDAA2158194 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Anne Arundel Md County

  • City

    Shady Side

  • Neighborhood

    --

  • Year Built

    1950

  • HOA Fees

    -

  • Finished Area

    2,674 sqft

  • Lot Size

    15,000.1 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDAA2158194

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    1

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 2

Interior

  • Window Features

    Bay/bow, Double Pane Windows

  • Heating

    Heat Pump(s)

  • Flooring

    Hardwood, Carpet

  • Interior Features

    Combination Dining/living, Built Ins, Window Treatments, Entry Level Bedroom, Upgraded Countertops, Wood Floors, Floor Plan Traditional

  • Appliances

    Dishwasher, Disposal, Dryer, Microwave, Oven/range Gas, Refrigerator, Stove, Washer

  • Cooling

    Central A/c

  • Sewer

    Public Sewer

Construction

  • Year Built

    Year Built: 1950

  • Home type

    Single Family Residence

  • Property Condition

    Excellent

  • Foundation Details

    Other

  • Construction Materials

    Vinyl Siding

  • Architectural Style

    Contemporary

Utilities & Energy

  • Parking Features

    Paved Driveway, Asphalt Driveway

  • Fireplace Features

    Mantel(s)

  • Water Source

    Public

Other Features

  • Subdivision Name

    Shady Side

  • Lot Features

    Additional Lot(s), Partly Wooded

  • Patio And Porch Features

    Deck, Porch, Screened

Price History

DateEventPrice

10/08/2026

Source: mls_logoBright MLS-NJ #MDAA2158194

Listed for Sale

$749,900 +90.81%

$280/sqft

09/30/2015

Source: mls_logoBright MLS-NJ #1001269345

Price Increased

$393,000 +18614.29%

$147/sqft

09/13/2014

Source: mls_logoBright MLS-NJ #1003187632

Sold

$2,100

$1/sqft

Nearby Homes

Based on information from Bright MLS through Oct 09, 2026, 12:00PM. 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. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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