15

Shady Side, MD Homes for Sale under $400,000

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  • 4846 Woods Wharf Rd, Shady Side, MD 20764
    4846 Woods Wharf Rd, Shady Side, MD 20764
    4846 Woods Wharf Rd, Shady Side, MD 20764
    /6

    $249,999

    • Land
    • 33,541 Sq Ft
    • $324,674 per Acre

    4846 Woods Wharf Rd, Shady Side, MD 20764

    Vacant Lot Ideal for Expansion or New Venture. Perfect for Boat Storage or New Building. Leverage its proximity to high-demand recreational areas for profitable boat and trailer storage, or business vehicles, or develop the lot into a commercial building for your business, or to lease the space to a business who is looking to serve the local community.

    Scott Cleary RE/MAX One

    4846 Woods Wharf Rd, Shady Side, MD 20764
  • 5209 Al Jones Dr, Shady Side, MD 20764
    5209 Al Jones Dr, Shady Side, MD 20764
    5209 Al Jones Dr, Shady Side, MD 20764
    /25

    $149,900

    • Land
    • 4,356 Sq Ft
    • $1,499,000 per Acre

    5209 Al Jones Dr, Shady Side, MD 20764

    WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay. Nestled in the quiet, secluded community of Columbia Beach, this approximately 4,450-square-foot homesite is already serviced by public sewer, making it an exceptional opportunity to bring your vision to life. Wake up to

    Mark Frisco CENTURY 21 New Millennium

    5209 Al Jones Dr, Shady Side, MD 20764
  • 6372 Shady Side Rd, Shady Side, MD 20764
    6372 Shady Side Rd, Shady Side, MD 20764
    6372 Shady Side Rd, Shady Side, MD 20764
    /34

    $380,000

    • 3 Beds
    • 3 Baths
    • 2,450 Sq Ft

    6372 Shady Side Rd, Shady Side, MD 20764

    Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the

    Brenda Sarver Maryland Realty Connection

    6372 Shady Side Rd, Shady Side, MD 20764
  • 1436 Haile Pkwy, Shady Side, MD 20764
    1436 Haile Pkwy, Shady Side, MD 20764
    /2

    $100,000

    • Land
    • 1 Acre
    • $100,000 per Acre

    1436 Haile Pkwy, Shady Side, MD 20764

    Sub-division potential for this undeveloped, 1 acre lot! May be able to reconfigure to 2 separate lots. Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility. With

    Joan Stansfield Samson Properties

    1436 Haile Pkwy, Shady Side, MD 20764
  • 4912 Mariners Dr, Shady Side, MD 20764
    4912 Mariners Dr, Shady Side, MD 20764
    4912 Mariners Dr, Shady Side, MD 20764
    /42

    $399,900

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,386 Sq Ft

    4912 Mariners Dr, Shady Side, MD 20764

    Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, where coastal living meets everyday affordability. This beautifully updated home offers gorgeous Chesapeake Bay views and the rare bonus of an included boat slip — making waterfront living more accessible than ever. Inside offers a light-filled floorplan, wide open living room, an open kitchen shines with

    Sam Barbieri RE/MAX United Real Estate

    4912 Mariners Dr, Shady Side, MD 20764
  • 1500 Garst Rd, Shady Side, MD 20764
    1500 Garst Rd, Shady Side, MD 20764
    1500 Garst Rd, Shady Side, MD 20764
    /24

    $364,000

    $12K PRICE INCREASE
    • 2 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    1500 Garst Rd, Shady Side, MD 20764

    Enjoy water views and the best of coastal living in this charming home, ideally located in a private waterfront community with exclusive access to a boat ramp and sandy beach. The open-concept living and kitchen area creates an inviting space for everyday living and entertaining, while the large fenced backyard offers plenty of room for pets, play, and outdoor gatherings. A rare opportunity to

    Maggie Richards Berkshire Hathaway HomeServices PenFed Realty

    1500 Garst Rd, Shady Side, MD 20764
  • 4738 Washington Ave, Shady Side, MD 20764
    4738 Washington Ave, Shady Side, MD 20764
    4738 Washington Ave, Shady Side, MD 20764
    /27

    $359,900

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,223 Sq Ft

    4738 Washington Ave, Shady Side, MD 20764

    Perfect little rancher in a water access community. 3 bedrooms, 2 full baths, and a full fenced yard. Heated family/sun room out back and setup for a stackable washer/dryer inside.

    Kyle Squires Lazar Real Estate

    4738 Washington Ave, Shady Side, MD 20764
  • 1172 Cedar Ave, Shady Side, MD 20764
    1172 Cedar Ave, Shady Side, MD 20764
    1172 Cedar Ave, Shady Side, MD 20764
    /45

    $325,000

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    1172 Cedar Ave, Shady Side, MD 20764

    Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updated rancher style home offers a rare affordable opportunity to enjoy Chesapeake Bay living, just one hour from the City. So much potential! Make it your weekend retreat, an Air B&B, or perhaps a tranquil place to retire, without

    James Basuel Weichert, REALTORS

    1172 Cedar Ave, Shady Side, MD 20764
  • 5235 Al Jones Dr, Shady Side, MD 20764
    5235 Al Jones Dr, Shady Side, MD 20764
    5235 Al Jones Dr, Shady Side, MD 20764
    /17

    $349,870

    • Land
    • 6,534 Sq Ft
    • $2,332,467 per Acre

    5235 Al Jones Dr, Shady Side, MD 20764

    Unique Waterfront Lot Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to own a buildable waterfront lot in the serene, gated community of Columbia Beach, offering breathtaking views of the Chesapeake Bay. This exclusive neighborhood is just 30 minutes from the I-495 Beltway and Annapolis, and only 45 minutes to Washington, D.C., and the

    Rodrigo Cruz Long & Foster Real Estate, Inc.

    5235 Al Jones Dr, Shady Side, MD 20764
  • 1445 & 1447 Haile Pkwy, Shady Side, MD 20764
    1445 & 1447 Haile Pkwy, Shady Side, MD 20764
    /2

    $100,000

    • Land
    • 29,620 Sq Ft
    • $147,059 per Acre

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764

    Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility. With convenient access to Route 2, commuting to Annapolis, Baltimore, or Washington, D.C., is effortless—yet

    Joan Stansfield Samson Properties

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764
  • 1495 Shady Rest Rd, Shady Side, MD 20764
    1495 Shady Rest Rd, Shady Side, MD 20764
    /2

    $125,000

    • Land
    • 4 Acres
    • $31,250 per Acre

    1495 Shady Rest Rd, Shady Side, MD 20764

    Discover a unique investment opportunity with this expansive 4-acre parcel of land, perfect for those looking to capitalize on future development potential. Nestled in a serene setting, this property offers ample space for creative vision-whether you envision a private retreat, agricultural venture, or a residential community. The generous lot size provides flexibility for various projects,

    Shawn Kerr Union Preferred Realty

    1495 Shady Rest Rd, Shady Side, MD 20764
  • 1186 & 1188 Poplar Ave, Shady Side, MD 20764
    1186 & 1188 Poplar Ave, Shady Side, MD 20764
    /2

    $120,000

    • Land
    • 19,166 Sq Ft
    • $272,727 per Acre

    1186 & 1188 Poplar Ave, Shady Side, MD 20764

    Sale includes both 1186 & 1188 Poplar Ave. Lots: 10,11,12,13 Rare opportunity to purchase two adjoining parcels totaling approximately 19,000 square feet or nearly 1/2 acre in the water-privileged community of Cedarhurst on the Bay. Build your dream home and enjoy the relaxed Chesapeake Bay lifestyle that makes Shady Side one of Anne Arundel County's hidden gems. Community amenities include Bay

    Adam Carpenter Keller Williams Flagship

    1186 & 1188 Poplar Ave, Shady Side, MD 20764
  • 5649 Shady Side Rd, Churchton, MD 20733
    5649 Shady Side Rd, Churchton, MD 20733
    5649 Shady Side Rd, Churchton, MD 20733
    /36

    $375,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,148 Sq Ft

    5649 Shady Side Rd, Churchton, MD 20733

    Own this home with no down payment required. This property qualifies for USDA and FHA solar+ financing, making homeownership attainable. This well-maintained home is located in an area eligible for a 100% USDA Zero-Downpayment Loan, providing a chance to buy a move-in ready home without the financial burden of a down payment. The home features a bright, open layout on a single level, designed for

    Linda Pelton Taylor Properties

    5649 Shady Side Rd, Churchton, MD 20733
  • 1432 Heile Pkwy, Shady Side, MD 20764
    1432 Heile Pkwy, Shady Side, MD 20764
    /2

    $169,950

    • 2 Beds
    • 1 Bath
    • 576 Sq Ft

    1432 Heile Pkwy, Shady Side, MD 20764

    ALL CASH OFFERS-FIRE DAMANGED INTERIOR- TOTAL REHAB-2 BR 1 Bath quiet secluded street. New Homes being built on same street.Owner reserves right to accept or reject any offer. Owner doing 1031 tax free exchange.Settlement 7-30 days.Haile Parkway/tax record HeileALL OFFERS DUE BY MONDAY JULY 20, 2026 4PM

    Stephen Watson Flag Real Estate Inc.

    1432 Heile Pkwy, Shady Side, MD 20764
  • 6201 Shady Side Rd, Shady Side, MD 20764
    6201 Shady Side Rd, Shady Side, MD 20764
    6201 Shady Side Rd, Shady Side, MD 20764
    /24

    $399,900

    $49K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft

    6201 Shady Side Rd, Shady Side, MD 20764

    Spacious 2,807 sq. ft. home offering exceptional potential for investors, multi-generational living, or rental income opportunities. The main residence features two bedrooms, one full bath, a kitchen, utility room, and a spacious family room with sliding doors leading to the rear deck. The attached in-law suite has its own private entrance and separate electric meter. Currently tenant-occupied by

    Ray Mudd Schwartz Realty, Inc.

    6201 Shady Side Rd, Shady Side, MD 20764
Maryland Anne Arundel County

Real Estate & Homes in Shady Side, MD under $400,000

Home Prices in Shady Side, MD

The median home sale price in Shady Side, MD is $439,950, up 10% year-over-year. Homes in Shady Side sell in 42 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$439,950
Median Single Family Sale Price
$449,950
Median 2 Bedroom Sale Price
$325,000
Median 1 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$319
Number of Homes for Sale
32
Last 12 months Home Sales
92
Months of Supply
4.20
Median List Price
$449,975
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
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