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Newest Homes for Sale in Shady Side, MD

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  • 5649 Shady Side Rd, Churchton, MD 20733
    5649 Shady Side Rd, Churchton, MD 20733
    5649 Shady Side Rd, Churchton, MD 20733
    /46

    $375,000

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

    5649 Shady Side Rd, Churchton, MD 20733

    COMING SOON !

    Linda Pelton Taylor Properties

    5649 Shady Side Rd, Churchton, MD 20733
  • 5503 Manistique Ct, Churchton, MD 20733
    5503 Manistique Ct, Churchton, MD 20733
    /2

    $489,990

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,679 Sq Ft

    5503 Manistique Ct, Churchton, MD 20733

    Tucked into the established Franklin Manor Beach community in Churchton, this 3-bedroom, 2.5-bath colonial delivers comfortable two-level living with one of the area's most appealing lifestyle perks deeded water access to the Chesapeake Bay just six blocks away, including a community pier on navigable water. The traditional floor plan makes the most of 1,679 square feet. A welcoming front porch

    Kara Chaffin Donofrio Long & Foster Real Estate, Inc.

    5503 Manistique Ct, Churchton, MD 20733
  • 1183 Cedar Ave, Shady Side, MD 20764
    1183 Cedar Ave, Shady Side, MD 20764
    1183 Cedar Ave, Shady Side, MD 20764
    /33

    $535,000

    • 4 Beds
    • 3 Baths
    • 1,964 Sq Ft

    1183 Cedar Ave, Shady Side, MD 20764

    Professional pictures coming!! Rarely available and proudly offered for the first time, this spacious split-foyer home is nestled on nearly a quarter-acre lot in the highly desirable water-privileged community of Cedarhurst. Lovingly maintained by its original owner, this well cared for residence offers 4 bedrooms, 3 full bathrooms, and multiple living spaces designed for both comfort and

    John Tarpley Schwartz Realty, Inc.

    1183 Cedar Ave, Shady Side, MD 20764
  • 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
  • 1241 Johnson Dr, Shady Side, MD 20764
    1241 Johnson Dr, Shady Side, MD 20764
    /2

    $750,000

    Open House 7/25 Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    1241 Johnson Dr, Shady Side, MD 20764

    Professional photos coming soon! New roof & gutters being installed as we speak! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where breathtaking views, abundant wildlife, and the ultimate Chesapeake Bay lifestyle come together. Perfectly positioned on a beautifully level lot, this exceptional property offers a private pier ideal for launching a

    Nicki Palermo RE/MAX One

    1241 Johnson Dr, Shady Side, MD 20764
  • 5125 Marx Dr, West River, MD 20778
    5125 Marx Dr, West River, MD 20778
    5125 Marx Dr, West River, MD 20778
    /30

    $495,000

    • 3 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    5125 Marx Dr, West River, MD 20778

    Peaceful cul-de-sac setting, expansive covered porch, hardwood floors, and a spacious backyard just moments from the water.Set on a quiet street near the shoreline, this 3-bedroom, 2.5-bath home offers generous indoor and outdoor living in a location where wooded surroundings and nearby waterways create a slower pace of life. Inside, the main level has multiple living spaces that can easily

    Chris Craddock EXP Realty, LLC

    5125 Marx Dr, West River, MD 20778
  • 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
  • 1016 Allen Ave, West River, MD 20778
    1016 Allen Ave, West River, MD 20778
    1016 Allen Ave, West River, MD 20778
    /50

    $499,990

    • 3 Beds
    • 2.5 Baths
    • 1,783 Sq Ft

    1016 Allen Ave, West River, MD 20778

    Welcome home to this beautiful brick-front Colonial nestled in the sought-after waterfront community of Back Bay Beach in West River! Just in time for summer, enjoy the ultimate Chesapeake Bay lifestyle with community access to a boat launch—perfect for launching your boat, jet skis, kayaks, and all your favorite water toys for endless days on the water. Situated on a spacious lot, this

    Nicki Palermo RE/MAX One

    1016 Allen Ave, West River, MD 20778
  • 4734 Oak Rd, Shady Side, MD 20764
    4734 Oak Rd, Shady Side, MD 20764
    4734 Oak Rd, Shady Side, MD 20764
    /49

    $625,000

    • 4 Beds
    • 2.5 Baths
    • 2,511 Sq Ft

    4734 Oak Rd, Shady Side, MD 20764

    Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint waterfront community of Felicity Cove. The ground level features two bedrooms (one without a closet), a full bathroom, and a second kitchen, making it an ideal space for guests, extended family, or multi-generational living. The main living area is located on the second floor to take full advantage of the

    Ray Mudd Schwartz Realty, Inc.

    4734 Oak Rd, 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
  • 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

    $449,000

    • 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
  • 4951 Bonniewood Dr, Shady Side, MD 20764
    4951 Bonniewood Dr, Shady Side, MD 20764
    4951 Bonniewood Dr, Shady Side, MD 20764
    /46

    $475,000

    Open Sun 12PM - 3PM
    • 3 Beds
    • 2.5 Baths
    • 1,456 Sq Ft

    4951 Bonniewood Dr, Shady Side, MD 20764

    Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. Situated on over one-third of an acre, this well-maintained 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, space, and community living. The fully fenced backyard provides an ideal setting for entertaining, family gatherings, or simply

    John Tarpley Schwartz Realty, Inc.

    4951 Bonniewood Dr, Shady Side, MD 20764
  • 5222 Spring Ave, Shady Side, MD 20764
    5222 Spring Ave, Shady Side, MD 20764
    5222 Spring Ave, Shady Side, MD 20764
    /43

    $495,000

    • 4 Beds
    • 3 Baths
    • 1,730 Sq Ft

    5222 Spring Ave, Shady Side, MD 20764

    Multi Offer Scenario. Please submit final and best offer by 12:00 noon Monday, July 13th. Set on a large double corner lot in the waterfront community of Cedarhurst, this four-bedroom, three full bath Cape Cod offers a flexible layout and thoughtful updates throughout in a setting where everyday can feel like a vacation. Just down the street from the water, the home blends relaxed coastal living

    Agent Photo

    Chris James

    Northrop Realty

    5222 Spring Ave, Shady Side, MD 20764
  • 5211 Al Jones Dr, Shady Side, MD 20764
    5211 Al Jones Dr, Shady Side, MD 20764
    5211 Al Jones Dr, Shady Side, MD 20764
    /39

    $535,000

    • 2 Beds
    • 1.5 Baths
    • 1,244 Sq Ft

    5211 Al Jones Dr, Shady Side, MD 20764

    Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. Wake each morning to breathtaking sunrises over the water, best enjoyed from your expansive deck with a cup of coffee in hand—an experience that never gets old. Inside, the home is filled with natural light and features an open-concept layout designed to maximize those stunning bay views. The main level

    Ray Mudd Schwartz Realty, Inc.

    5211 Al Jones Dr, Shady Side, MD 20764
  • 1582 Snug Harbor Rd, Shady Side, MD 20764
    1582 Snug Harbor Rd, Shady Side, MD 20764
    1582 Snug Harbor Rd, Shady Side, MD 20764
    /54

    $619,900

    • 4 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    1582 Snug Harbor Rd, Shady Side, MD 20764

    Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new

    Steven Songer Maryland Waterfront Properties LLC

    1582 Snug Harbor Rd, Shady Side, MD 20764
  • 5331 Sweetwater Dr, West River, MD 20778
    5331 Sweetwater Dr, West River, MD 20778
    5331 Sweetwater Dr, West River, MD 20778
    /61

    $849,990

    • 4 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    5331 Sweetwater Dr, West River, MD 20778

    Stately brick-front Colonial located in the highly sought-after water-privileged community of West River Estates. This absolutely gorgeous home offers exceptional space, charm, and amenities throughout. The beautifully appointed kitchen features granite countertops, double wall ovens, a large center island with built-in cooktop, and ample cabinetry. French doors open to a bright all-season

    Ray Mudd Schwartz Realty, Inc.

    5331 Sweetwater Dr, West River, MD 20778
  • 4909 Olive St, Shady Side, MD 20764
    4909 Olive St, Shady Side, MD 20764
    4909 Olive St, Shady Side, MD 20764
    /40

    $490,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    4909 Olive St, Shady Side, MD 20764

    Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball

    Erica Baker TTR Sotheby's International Realty

    4909 Olive St, Shady Side, MD 20764
  • 4921 Olive St, Shady Side, MD 20764
    4921 Olive St, Shady Side, MD 20764
    4921 Olive St, Shady Side, MD 20764
    /32

    $419,900

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    4921 Olive St, Shady Side, MD 20764

    Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s cottage boasts beautiful water views from both floors. The inviting interior features a spacious kitchen with stainless steel appliances, while wrap-around windows flood the entire main living area with bright, natural light. Relax or entertain on the cozy screened-in front porch, or step out into the level,

    Eric Hovanky Redfin Corp

    4921 Olive St, Shady Side, MD 20764
  • 1527 Lincoln Rd, Shady Side, MD 20764
    1527 Lincoln Rd, Shady Side, MD 20764
    1527 Lincoln Rd, Shady Side, MD 20764
    /30

    $424,700

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    1527 Lincoln Rd, Shady Side, MD 20764

    Experience the best of the Chesapeake Bay in this 3-bedroom, 2.5-bathroom Colonial, in the sought-after Columbia Beach neighborhood! Nestled in a quiet, gated, water-privileged community, this home offers more than just a place to live—it offers a lifestyle complete with a private pier, boat ramp, tennis/basketball courts, and a playground. The heart of the home is the beautifully curated

    Mike Benton Home Towne Real Estate

    1527 Lincoln Rd, Shady Side, MD 20764
  • 4950 Bonniewood Dr, Shady Side, MD 20764
    4950 Bonniewood Dr, Shady Side, MD 20764
    4950 Bonniewood Dr, Shady Side, MD 20764
    /73

    $795,000

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft

    4950 Bonniewood Dr, Shady Side, MD 20764

    Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops,

    Jamie Angichiodo RE/MAX Leading Edge

    4950 Bonniewood Dr, 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
  • 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
  • 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
  • 4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    4721 Oak Rd, Shady Side, MD 20764
    /59

    $1,110,000

    Open Fri 3PM - 5PM $50K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,868 Sq Ft

    4721 Oak Rd, Shady Side, MD 20764

    Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an

    Angie Carr Riverscape Realty

    4721 Oak Rd, Shady Side, MD 20764
  • 1430 Haile Pkwy, Shady Side, MD 20764
    1430 Haile Pkwy, Shady Side, MD 20764
    1430 Haile Pkwy, Shady Side, MD 20764
    /33

    $650,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    1430 Haile Pkwy, Shady Side, MD 20764

    There aren't many opportunities left to build brand new in Anne Arundel County at this price point, and 1430 Haile Parkway is one of them. Haile Parkway is quiet, wooded, and tucked into the laid-back charm of Shady Side, close enough to everything you need, far enough away to actually exhale. New construction at this level of quality and finish from one of the area's most respected builders is a

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    1430 Haile Pkwy, Shady Side, MD 20764
  • 1110 Cherry Point Rd, West River, MD 20778
    1110 Cherry Point Rd, West River, MD 20778
    1110 Cherry Point Rd, West River, MD 20778
    /16

    $1,550,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,580 Sq Ft

    1110 Cherry Point Rd, West River, MD 20778

    TO BE BUILT – Exceptional Luxury Home with 1-Acre Waterfront Lot and Private Boat Ramp Experience the rare opportunity to build a custom luxury waterfront home just minutes to the Chesapeake Bay. Nestled on a tranquil wooded lot in West River, this stunning new construction residence offers the perfect blend of refined craftsmanship, modern comfort, and waterfront living. Thoughtfully designed

    Michael Reible Realty Advantage of Maryland LLC

    1110 Cherry Point Rd, West River, MD 20778
  • 1003 Henry Ave, West River, MD 20778
    1003 Henry Ave, West River, MD 20778
    1003 Henry Ave, West River, MD 20778
    /22

    $599,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,946 Sq Ft

    1003 Henry Ave, West River, MD 20778

    Located in the charming Back Bay Beach area of West River, 1003 Henry Avenue offers the relaxed feel of Southern Anne Arundel County living with easy access to the water, marinas, local dining, and nearby historic Galesville. Enjoy the laid-back coastal lifestyle of the West River, with Galesville Wharf, waterfront restaurants, boating access, and scenic outdoor destinations just minutes away.

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    1003 Henry Ave, West River, MD 20778
  • 5341 Al Jones Dr, Shady Side, MD 20764
    5341 Al Jones Dr, Shady Side, MD 20764
    5341 Al Jones Dr, Shady Side, MD 20764
    /48

    $745,000

    • 3 Beds
    • 2 Baths
    • 1,962 Sq Ft

    5341 Al Jones Dr, Shady Side, MD 20764

    Fantastic opportunity to own your own land lighthouse-inspired round house with water views! Perfect serene retreat for the commuter and/or investment opportunity. Quiet neighborhood, blue heron sightings, and all the advantages of coastal living without the summer beach traffic. Freshly painted! This unique home features 3 bedrooms, 2 full bathrooms, an open-concept layout, and a spacious family

    Melissa Wilson Redfin Corp

    5341 Al Jones Dr, Shady Side, MD 20764
  • 1217 Pine Ave, Shady Side, MD 20764
    1217 Pine Ave, Shady Side, MD 20764
    1217 Pine Ave, Shady Side, MD 20764
    /79

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,006 Sq Ft

    1217 Pine Ave, Shady Side, MD 20764

    Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner lot in the water-oriented community of Cedarhurst—where Chesapeake Bay living is part of everyday life. Just in time for summer, enjoy the opportunity to lease a boat slip for only $400 per year with direct access to the Chesapeake Bay, making weekends on the water easier than ever. Inside, you’ll find

    Nicki Palermo RE/MAX One

    1217 Pine Ave, 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
  • 1316 Juniper St, Shady Side, MD 20764
    1316 Juniper St, Shady Side, MD 20764
    1316 Juniper St, Shady Side, MD 20764
    /41

    $549,900

    New Construction $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,949 Sq Ft

    1316 Juniper St, Shady Side, MD 20764

    This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center

    Paul Lee Long & Foster Real Estate, Inc.

    1316 Juniper St, 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
  • 4750 Frederick Ave, Shady Side, MD 20764
    4750 Frederick Ave, Shady Side, MD 20764
    4750 Frederick Ave, Shady Side, MD 20764
    /76

    $3,500,000

    • 5 Beds
    • 5.5 Baths
    • 4,620 Sq Ft

    4750 Frederick Ave, Shady Side, MD 20764

    Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    4750 Frederick Ave, 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
  • 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
  • 0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
    /2

    $25,000

    • Land
    • 24,829 Sq Ft
    • $43,860 per Acre

    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764

    No address assigned for Lots 6 & 7. 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

    Joan Stansfield Samson Properties

    0 Haile Pkwy Unit MDAA2141624, Shady Side, MD 20764
  • 5314 Al Jones Dr, Shady Side, MD 20764
    5314 Al Jones Dr, Shady Side, MD 20764
    5314 Al Jones Dr, Shady Side, MD 20764
    /61

    $649,990

    New Construction $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    5314 Al Jones Dr, Shady Side, MD 20764

    6/26/26. Home is under roof ready for drywall. August delivery. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with time to personalize your selections so you can create a home that perfectly

    Ray Mudd Schwartz Realty, Inc.

    5314 Al Jones Dr, Shady Side, MD 20764
  • 1235 Spruce Ave, Shady Side, MD 20764
    1235 Spruce Ave, Shady Side, MD 20764
    1235 Spruce Ave, Shady Side, MD 20764
    /55

    $650,990

    New Construction $1K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    1235 Spruce Ave, Shady Side, MD 20764

    AUGUST Delivier!!!!Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    1235 Spruce Ave, Shady Side, MD 20764
  • 0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
    /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $227,273 per Acre

    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 7/24/2026, 10:00 AM. Bidding ends 7/28/2026, 12:40 PM. The list price is suggested opening bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in located in Shady Side, MD within Anne Arundel County. Its location is just a few minutes away to Herring Bay. It also offers

    Adam Shpritz Ashland Auction Group LLC

    0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
  • 1205 Poplar Ave, Shady Side, MD 20764
    1205 Poplar Ave, Shady Side, MD 20764
    /2

    $25,000

    • Land
    • 4,791 Sq Ft
    • $227,273 per Acre

    1205 Poplar Ave, Shady Side, MD 20764

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 7/24/2026, 10:00 AM. Bidding ends 7/28/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in Shady Side, MD within Anne Arundel County. It is just minutes away to Herring Bay and offers easy access to major traffic

    Adam Shpritz Ashland Auction Group LLC

    1205 Poplar Ave, Shady Side, MD 20764

Showing Results 1 - 40, Page 1 of 2

Maryland Anne Arundel County Shady Side

Newest Listings for Sale in Shady Side, MD

Frequently Asked Questions

What is the average home price in Shady Side, MD?
Homes for sale in Shady Side, MD have an average home price of $586,607.
How many homes have sold over the last 12 months in Shady Side, MD?
92 homes have sold in Shady Side, MD over the last 12 months.
What is the average household income in Shady Side, MD?
The average household income in Shady Side, MD is $141K.
What are the most popular zip codes in Shady Side, MD?
The most popular zip codes in Shady Side, MD include 20764, 20778, 20733, 20776 and 20751.
How much do you need to make to afford a house in Shady Side?
The median home price in Shady Side is $450,000. If you put a 20% down payment of $90,000 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $2,270 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $97K a year to afford the median home price in Shady Side. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Shady Side is $141K.
How are the schools in Shady Side, MD?
Shady Side, MD has highly rated public and private schools. Some of the best schools in Shady Side based on Niche Grades are Deale Elementary School, Shady Side Elementary School and Southern Middle School. Browse all the schools in Shady Side, MD to learn more.

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 41 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$439,950
Median Single Family Sale Price
$450,000
Median 2 Bedroom Sale Price
$325,000
Median 1 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$322
Number of Homes for Sale
31
Last 12 months Home Sales
92
Months of Supply
4.00
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
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