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Shady Side, MD Homes for Sale

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  • /32

    $399,900

    • 4 Beds
    • 1.5 Baths
    • 1,399 Sq Ft

    1199 Oak Ave, Shady Side, MD 20764

    Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub

    Agent Photo

    Bill Franklin

    Long & Foster Real Estate, Inc.

    (410) 835-7611

    1199 Oak Ave, Shady Side, MD 20764
  • /33

    $579,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    1225 Juniper St, Shady Side, MD 20764

    THIS IS A TO BE BUILT HOME

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (410) 724-1190

    1225 Juniper St, Shady Side, MD 20764
  • /53

    $649,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    1235 Spruce Ave, Shady Side, MD 20764

    THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home with interior selections!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.

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (443) 363-1364

    1235 Spruce Ave, Shady Side, MD 20764
  • /37

    $550,000

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,905 Sq Ft

    1411 Haile Pkwy, Shady Side, MD 20764

    Price reduction! This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy,

    Mary Gatton Redfin Corp

    1411 Haile Pkwy, Shady Side, MD 20764
  • /61

    $899,900

    • 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
  • /35

    $729,900

    • 3 Beds
    • 2 Baths
    • 1,866 Sq Ft

    1650 Cedar Ln, Shady Side, MD 20764

    Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife—waterfowl, deer, eagles, and more—all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is

    Ray Mudd Schwartz Realty, Inc.

    1650 Cedar Ln, Shady Side, MD 20764
  • /61

    $659,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    5314 Al Jones Dr, Shady Side, MD 20764

    4/6/26. Just broke ground. Late summer 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 reflects your

    Ray Mudd Schwartz Realty, Inc.

    5314 Al Jones Dr, Shady Side, MD 20764
  • /23

    $750,000

    • 4 Beds
    • 1.5 Baths
    • 2,144 Sq Ft

    1462 Snug Harbor Rd, Shady Side, MD 20764

    4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of MC heavy commercial zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can

    George Heine Schwartz Realty, Inc.

    1462 Snug Harbor Rd, Shady Side, MD 20764
  • /2

    $424,700

    Coming Soon
    • 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
  • /44

    $1,470,000

    New Construction $125K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    5235 Al Jones Dr, Shady Side, MD 20764

    To be built by Whitehall Building & Co., Annapolis’ leading luxury waterfront builder. Set within the sought-after Columbia Beach community, this coastal-style home captures the best of Chesapeake Bay living with panoramic views and the rare protection of a cove-front setting. With Whitehall, the path to building is refreshingly simple. Their step-by-step process begins with a complimentary

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    5235 Al Jones Dr, Shady Side, MD 20764
  • /41

    $569,900

    New Construction
    • 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
  • /44

    $599,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    4908 Olive St, Shady Side, MD 20764

    5/16/26 Under roof and ready for drywall. EXPECTED JULY 2026 DELIVERY. 100% financing available with USDA loan. $10k. closing assistance with use of preferred lender and title company. Must use builder contract - buyer responsible for 100% transfer taxes**. Schaefer Homes brings to you their latest Monroe model located in water privilege community of Westelee offering community beach, pier,

    Ray Mudd Schwartz Realty, Inc.

    4908 Olive St, Shady Side, MD 20764
  • /32

    $464,990

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,598 Sq Ft

    1222 Juniper St, Shady Side, MD 20764

    Would you love to live in a water oriented community? Have you ever? Come take a look at this year 2020 built 3 bedroom 2.5 bathroom home located in the AVALON SHORES community surrounded by the beautiful Chesapeake Bay and tributaries. Avalon Shores has wonderful neighborhood amenities including play areas, beach and boat launch . Come see this traditional home with an open floor plan. Plenty of

    Jesse Hoffman HomeSmart

    1222 Juniper St, Shady Side, MD 20764
  • /30

    $469,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    1161 Steamboat Rd, Shady Side, MD 20764

    Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space — thoughtfully laid out to balance comfort and function.Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed

    Christine Saunders Compass

    1161 Steamboat Rd, Shady Side, MD 20764
  • /11

    $149,999

    • Land
    • 6,098 Sq Ft
    • $1,071,421 per Acre

    5250 Al Jones Dr, Shady Side, MD 20764

    LAND LAND in a gated private community! The lot is 3 small lots in total all adjacent to each other. The county has approved building on the lots as ONE dwelling. The home will need to adhere to the building envelope but can be as high as needed (county approved height change)...building a car garage on bottom and build up in SF from there!! A well is needed and there is public septic. I can

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, Shady Side, MD 20764
  • /4

    $50,000

    • Land
    • 7,405 Sq Ft
    • $294,118 per Acre

    4907 Quince St, Shady Side, MD 20764

    Per the recorded Conservation Easement. No primary residence shall be constructed

    Ray Mudd Schwartz Realty, Inc.

    4907 Quince St, Shady Side, MD 20764
  • /2

    $40,000

    • Land
    • 14,810 Sq Ft
    • $117,647 per Acre

    5771 Shady Side Rd, Churchton, MD 20733

    Residential building lot awaits new owner. Sold as is .

    Joseph Butcher Long & Foster Real Estate, Inc.

    5771 Shady Side Rd, Churchton, MD 20733
  • /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
  • /42

    $429,900

    • 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
  • /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 6/2/2026 @ 10:00 AM. Bidding ends 6/4/2026 @ 12:50 PM. 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 easy

    Adam Shpritz Ashland Auction Group LLC

    0 Pine Ave Unit MDAA2139458, 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
  • /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
  • /27

    $1,495,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    4923 E Chalk Point Rd, West River, MD 20778

    This coastal home in the sought-after Chalk Point community offers the best of waterfront living. Wake up in the waterfront primary suite with sweeping 180-degree views and enjoy your morning coffee from the private balcony overlooking the water. Designed for both privacy and entertaining, the home features a spacious deck and patio off the main living area, perfect for outdoor gatherings and

    Amelia Whitman Long & Foster Real Estate, Inc.

    4923 E Chalk Point Rd, West River, MD 20778
  • /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 6/9/2026 @ 10:00 AM. Bidding ends 6/11/2026 @ 12:05 PM. List Price is 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 arteries

    Adam Shpritz Ashland Auction Group LLC

    1205 Poplar Ave, 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
  • /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
  • /42

    $474,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    1512 Lincoln Rd, Shady Side, MD 20764

    This is a luxury home in Shady Side- turn key in every way for long term low maintenance living. This is not a cosmetic renovation. This home has been comprehensively rebuilt from the inside out, offering the rare combination of modern luxury finishes and complete system-level replacement in an established gated, water-privileged community in Shady Side. Every major component has been replaced,

    Pedro Paz Coldwell Banker Realty

    1512 Lincoln Rd, Shady Side, MD 20764
  • /72

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 1,812 Sq Ft

    1005 Hawk Channel Ct, West River, MD 20778

    BUYERS GOT COLD FEET! No inspections were completed. Welcome to the rarely available water- privileged Cedarlea community in West River—Tucked away at the end of a quiet, family-friendly cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and privacy and is ready for its new owners. From the moment you arrive, the inviting front porch sets

    Stephanie Smith Douglas Realty, LLC

    1005 Hawk Channel Ct, West River, MD 20778
  • /101

    $2,425,000

    • 5 Beds
    • 5 Baths
    • 5,854 Sq Ft

    1125 Cherry Point Rd, West River, MD 20778

    Prepare to be WOW'd by this stunning, custom-built waterfront showpiece where every detail has been thoughtfully curated and nothing is ordinary. From the moment you arrive, the approach makes a lasting impression -- both private and substantial. The paver driveway with expanded parking, framed by professionally designed landscaping with full irrigation, is anchored by an expansive lush front

    Joan Stansfield Samson Properties

    1125 Cherry Point Rd, West River, MD 20778
  • /72

    $1,149,000

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

    1268 Hayes Rd, Shady Side, MD 20764

    Discover your dream lifestyle in this exceptional 3 bedroom 2 full bath waterfront property located at 1268 Hayes Road in the charming community of Shady Side, MD. combining the peacefulness of a secluded setting with essential modern amenities. As you step inside you'll notice the sun drenched open floor plan complete with a large cooks kitchen featuring a huge center island, cozy breakfast nook

    Casey A Sutherland Maryland Waterfront Properties LLC

    1268 Hayes Rd, Shady Side, MD 20764
  • /39

    $550,000

    • 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
  • /3

    $69,999

    $10K PRICE DROP
    • Land
    • 1.04 Acres
    • $67,307 per Acre

    5280 Cedar St, West River, MD 20778

    Beautiful 1.04-acre wooded lot offering privacy and a peaceful natural setting. The property provides a wonderful opportunity to build your dream home surrounded by trees while still being conveniently located near local amenities, restaurants, shopping, and commuter routes.

    Melissa Chick Engel & Völkers Annapolis

    5280 Cedar St, West River, MD 20778
  • /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
  • /68

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    1221 Cove Dr, Churchton, MD 20733

    1221 Cove Drive is a rare non-riparian waterfront property on Deep Cove Creek — the publicly-owned buffer between the property line and the water gives you open creek views, shoreline access, and a pier along the waterfront, without the full tax burden of direct waterfront ownership.Set on a 3⁄4-acre, privately wooded lot in Franklin Manor, the property offers the kind of seclusion that’s

    Ben Garner Cummings & Co. Realtors

    1221 Cove Dr, Churchton, MD 20733

Why Live in Shady Side

Life in Shady Side revolves around the water. Facing the Chesapeake Bay on a peninsula in Anne Arundel County, this area is commutable to metros like Annapolis and Washington, D.C., but still offers a slow-paced life on the water. “I think it’s a ...

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 $579,746.
How many homes have sold over the last 12 months in Shady Side, MD?
95 homes have sold in Shady Side, MD over the last 12 months.
What are the most popular zip codes in Shady Side, MD?
The most popular zip codes in Shady Side, MD include 20778, 20764, 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 $443,500. If you put a 20% down payment of $88,700 and had a 30-year fixed mortgage with an interest rate of 6.36%, your estimated principal and interest payment would be $2,210 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $95K a year to afford the median home price in Shady Side. Learn how much home you can afford with our Home Affordability Calculator.
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 Trends in Shady Side, MD

Housing Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$439,950
Average Price Per Sq Ft
$322
Number of Homes for Sale
19
Last 12 months Home Sales
95
Months of Supply
2.40
Median List Price
$443,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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