Shady Side MD Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,456
Status:
Active
MLS#:
MDAA2114056
Type:
Single Family-Detached
Subdivision:
Idlewilde On The Bay
Lot size:
0.18 Acres
Year built:
1945
Courtesy: Samson Properties 443-542-2251
View additional info

ADDITIONAL INFORMATION

Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake Bay front communnity of Idlewilde! Main level bedroom and full bathroom, waterview from front second level bedroom, and off street parking. This home has been completely updated with the main level having luxury vinyl flooring and fresh paint. The spacious kitchen has granite countertops, wood cabinets, and stainless steel appliances. Both bathrooms have beautiful ceramic tile and luxury vinyl flooring. The yard is fully fenced and includes a detached garage with off street parking. The community pier, which is a 2-minute walk, is on the Chesapeake Bay and has amazing views of the Bay Bridge. The Idlewilde community is a peaceful retreat location that is close to many shops and restaurants.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,000
Status:
Active
MLS#:
MDAA2128520
Type:
Single Family-Detached
Subdivision:
Idlewilde On The Bay
Lot size:
0.22 Acres
Year built:
1983
Courtesy: Samson Properties 304-930-5128
View additional info

ADDITIONAL INFORMATION

Peaceful Living by the Bay – Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural beauty—with low maintenance. Just a short walk to the bay front, you’ll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates—roof, HVAC, water softener, and well pump—all done within the last 3 years—mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage and a roomy driveway (with space for a boat or guests), and surrounding greenery make outdoor living simple and serene. Plus, the neighboring nature reserve means no new development next door—ever. If you’re ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,300
Status:
Active
MLS#:
MDAA2127962
Type:
Single Family-Detached
Subdivision:
Idlewilde On The Bay
Lot size:
0.17 Acres
Year built:
1983
Courtesy: Realinvestors Real Estate Services, LLC 301-850-3012
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ADDITIONAL INFORMATION

NEW PRICE!! Amazing opportunity to own an affordable beautifully remodeled home in the waterfront community. Just a short walk from the Chesapeake Bay, this 4-BR, 2-BA home offers approx. 1,300 sq ft of modern living, including a Brand-New signature designer kitchen with an eat-in island, New trash compactor, New security system, New lighting, New Appliances and High End finishes throughout....it's worth the drive to see! Additional features include New roof, New siding, New floors, New bathrooms, New central air, New water heater, New HVAC, New primary suite, and New windows. The property includes a large backyard with a shed for extra storage or convert it for extra space like a workshop, craft room, or hangout area. The spacious primary suite provides a relaxing retreat, while three additional bedrooms offer flexibility for guests, a home office, home gym or hobbies. Every detail has been thoughtfully updated, making this single level home completely move-in ready. Located just steps from the water, Idlewilde on the Bay offers a true sense of community and just a few miles from Annapolis, Washington DC or Baltimore including military locations like the Naval Academy, Fort Meade, NSA and Fort Andrews. Whether you’re searching for a year-round residence or a weekend escape, this property is ready to welcome you home today. Welcome home to Shady Side! ** Please contact the co-listing agent for details **

Beds:
3
Baths:
2.00
Sq.Ft.:
1,062
Status:
Active
MLS#:
MDAA2130044
Type:
Single Family-Detached
Subdivision:
Cedarhurst On The Bay
Lot size:
0.11 Acres
Year built:
1981
Courtesy: Schwartz Realty, Inc. 301-261-9700
View additional info

ADDITIONAL INFORMATION

This beautiful home is steps from the Chesapeake Bay and the community marina, beach, playground, and more—making it the perfect blend of comfort and location. Step inside to discover an open floor plan featuring a spacious kitchen with quartz countertops, stainless steel appliances, and a clear view of the living room—ideal for entertaining or everyday living. Stylish LVP flooring runs throughout. The primary bedroom includes an ensuite bath with a walk-in shower, while a second full bath in the hallway offers a tub for guests. Outside, enjoy a large deck that flows to a paver patio and a private, fenced backyard. The front porch provides a peaceful spot to relax and enjoy gentle bay breezes and a peek of the water. Home qualifies for 100% USDA financing. Current flood insurance cost is $734 year.

Beds:
2
Baths:
2.00
Sq.Ft.:
984
Status:
Active
MLS#:
MDAA2127796
Type:
Single Family-Detached
Subdivision:
Snug Harbor
Lot size:
0.23 Acres
Year built:
1950
Courtesy: RE/MAX One 410-535-6291
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ADDITIONAL INFORMATION

Welcome to 4950 W End Ave – a charming coastal bungalow just steps from the Chesapeake Bay! This beautifully renovated home perfectly blends modern updates with relaxed bay-side living. Set on a total of .242 acs (additional lot included total), this property offers serenity, space, and privacy. Step inside to an open and airy floor plan filled with natural light. Warm hardwood floors, a soft coastal palette, and stylish finishes create a space that feels both fresh and welcoming. The updated kitchen features sleek gray cabinetry, butcher block counters, a full pantry, and an easy flow into the dining and living areas – perfect for entertaining or everyday comfort. The main level bedroom and renovated bath offer convenience, while the upper-level suite provides a personal retreat with a private bath. A new mini-split system adds year-round comfort and energy efficiency. Outside, enjoy ample parking, a spacious yard, your own putting green, a large storage shed, newer deck, and your own personal boat slip – ready for your next day on the water! Whether hosting summer cookouts or relaxing after a day on the bay, you’ll love the laid-back seaside vibe this property delivers. Located in a water-privileged community offering a bayside pier, boat ramp, and entertaining areas, you’ll experience the best of Chesapeake living right at your doorstep. Ideal as a full-time residence, weekend getaway, or vacation investment.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,024
Status:
Active
MLS#:
MDAA2122792
Type:
Single Family-Detached
Subdivision:
Idlewilde Acres
Lot size:
1 Acres
Year built:
1989
Courtesy: Schwartz Realty, Inc. 301-261-9700
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ADDITIONAL INFORMATION

This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room featuring a gas fireplace and a sliding door that leads to a stunning sunroom and adjacent deck—perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full bath. Two additional bedrooms and a second full bath provide plenty of space for family or guests. Additional highlights include a two-car garage, a two-car carport, a large storage shed, and a handicap-accessible ramp. Situated on a level, usable one-acre lot, this home combines comfort, functionality, and outdoor space in a peaceful setting.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,399
Status:
Active
MLS#:
MDAA2121744
Type:
Single Family-Detached
Subdivision:
Cedarhurst On The Bay
Lot size:
0.17 Acres
Year built:
1960
Courtesy: Wright Real Estate, LLC 301-213-6910
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ADDITIONAL INFORMATION

Welcome to Cedarhurst On The Bay — Your Bayside Retreat Awaits! Nestled in the serene, historic enclave of Cedarhurst On The Bay in Shady Side, Maryland, this beautiful single-level home is the perfect blend of comfort, convenience, and coastal charm. Set on a generous double lot and built on a durable slab foundation, this residence offers 4 bedrooms, 1.5 bathrooms, and a thoughtfully laid-out floor plan that’s move-in ready—with energy-saving solar panels already in place. Enjoy all that the sought-after Cedarhurst On The Bay community has to offer, including a waterfront pier, boat slips, community center, playground, and open green spaces with stunning bay views. A rare find offering coastal living and neighborhood charm. With modern updates, waterfront access, stellar neighborhood amenities, and solar energy features, this is more than a property—it’s a lifestyle. Ready to embrace a serene yet spirited coastal community? Let’s bring you home.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDAA2121052
Type:
Single Family-Detached
Subdivision:
Avalon Shores
Lot size:
0.13 Acres
Year built:
1991
Courtesy: Investors Management, Inc. 202-462-1874
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ADDITIONAL INFORMATION

Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highly desirable Avalon Shores community in Shady Side, Maryland. This well-maintained home strikes the perfect balance between comfort and character. The covered front porch invites you to unwind and enjoy seasonal water views, setting the tone for peaceful, waterfront living. Inside, you’ll find a bright, open interior with a spacious living area, an updated kitchen with stainless steel appliances, and a convenient half bath on the main level, perfect for entertaining or relaxing. Upstairs, you'll find three generously sized bedrooms, including a primary suite with its own private bath, a closet system, new carpet, and skylights that allow tons of natural light. An additional full bath is available for family or guests. Out back, the fully fenced yard and large deck, offers plenty of space for pets, play, or gardening, perfect for those who enjoy outdoor living. You will also find a large shed, great to store all of your outdoor toys. Whether you're hosting a barbecue or simply soaking in the sunshine, this yard is ready for your personal touch. Residents of Avalon Shores enjoy water access, a community beach, boat ramp, pier, two playgrounds, and more just a short walk away. It’s the perfect spot for outdoor activities and enjoying the beauty of the Chesapeake Bay!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,727
Status:
Active
MLS#:
MDAA2120330
Type:
Single Family-Detached
Subdivision:
Columbia Beach
Lot size:
0.15 Acres
Year built:
2025
Courtesy: Hubble Bisbee Christie's International Real Estate 410-321-1411
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ADDITIONAL INFORMATION

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 consultation and clear timeline that removes the guesswork so you can enjoy the creative side of designing your dream home. Every stage is transparent and organized, from selections to finishes, with a dedicated team guiding you the entire way. Visit their website for more info about Whitehall! Building a custom home may take time, but with Whitehall it never feels complicated. You can relax knowing the details are handled and the outcome will be worth the journey. Enjoy the lifestyle that follows: a thoughtfully designed waterfront home built around how you truly live, with access to community amenities including a boat launch, pier, tennis and basketball courts, and playgrounds, all just a short drive from Annapolis, DC, and Baltimore.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,000
Status:
Active
MLS#:
MDAA2120174
Type:
Single Family-Detached
Subdivision:
Idlewilde On The Bay
Lot size:
0.22 Acres
Year built:
1983
Courtesy: Samson Properties 304-930-5128
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ADDITIONAL INFORMATION

Charming Rancher Just Steps from the Bay Front! Nestled on a peaceful corner lot and surrounded by the serenity of a protected nature reserve, this inviting 3-bedroom, 1-bath single-level rancher offers the perfect blend of privacy, charm, and location. Just a short walk to the scenic bay front, you’ll enjoy the coastal lifestyle with morning strolls, sunsets, and water views just minutes from your front door. Inside, the open-concept living and dining area welcomes you with warmth and character, featuring a cozy wood stove—perfect for chilly evenings. The bright red front door adds a cheerful pop of personality and curb appeal. Recent updates include a new roof, HVAC system, water softener, and well pump—all less than 3 years old—offering peace of mind and move-in-ready comfort. The spacious driveway accommodates up to three vehicles or your boat, ideal for those who love to explore the nearby waters. And with the adjacent nature reserve ensuring no future development next door, you’ll enjoy added privacy and natural views for years to come. Don’t miss this rare opportunity to own a well-maintained, coastal retreat with unbeatable location and timeless charm!

Beds:
9
Baths:
7.00
Sq.Ft.:
9,045
Status:
Active
MLS#:
MDAA2119496
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.69 Acres
Year built:
2006
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

HUGE PRICE REDUCTION !Welcome to 4701 Girton, waterfront estate boasting over 9,000 square feet sitting on an incredible point offering panoramic views to the Chesapeake Bay and West River. Views to take your breath away with over 250 ft of water frontage including rip rap, and bulkhead. There is plenty of room for your water toys with a deep-water pier, two boat lifts,12,000 lb, two jet ski lifts and more. A true entertaining mecca, this home boasts 9 bedrooms and 6.5 baths and expansive decks for off the back of the home. The spacious great room, as you walk through the front door, is spectacular with views surrounding you. The primary kitchen has a large island, granite countertops, professional gas stove, double ovens, with a grill, a Sub-Zero refrigerator, 2 dishwashers and 3 sinks. There is a generous primary bed and bath on the first floor and two primary suites on the second floor as well. Both offering amazing water views. This home includes a private in-law suite with a private entrance, full kitchen, living room, 2 bedrooms, a second level laundry room and a large balcony with water views inside and out. The home has a built-in elevator shaft to allow one to be installed. This home is highly efficient as well, with geothermal heating and AC, multiple radiant and baseboard heating zones, there is a combination of propane, oil and electric systems. The average monthly electric costs is a shocking $165/month average. Enjoy fishing, boating, crabbing or simply soaking up the views. You are conveniently located near marinas, waterfront dinning, parks, and an easy drive to Annapolis, DC and Baltimore. A unique home like this one is a rare gem indeed. Come live your dreams in this private waterfront escape.

Beds:
5
Baths:
2.00
Sq.Ft.:
1,812
Status:
Active
MLS#:
MDAA2119098
Type:
Single Family-Detached
Subdivision:
Cedarhurst On The Bay
Lot size:
0.11 Acres
Year built:
1980
Courtesy: Curtis Real Estate Company 410-268-8696
View additional info

ADDITIONAL INFORMATION

This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Community; Cedarhurst on the Bay. This remarkable property showcases the epitome of every day, vacation living with stunning views of The Chesapeake Bay. You will quickly be captivated by the grandeur that awaits you. The open layout seamlessly connects the living, dining and kitchen area, creating an ideal environment for entertaining family and friends. The kitchen is a chef's delight including ample storage space. The primary and additional bedrooms offer comfort and privacy for the entire family. Experience outdoor living at its finest in the expansive backyard. Whether you're hosting summer cookouts or simply enjoying an evening under the stars on your deck with spectacular views; the possibilities are endless. The community beach, marina, pier, boat ramp, playground and more are just steps away!! Welomce Home to 1220 Grove Ave.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,000
Status:
Active
MLS#:
MDAA2117718
Type:
Single Family-Detached
Subdivision:
Idlewilde On The Bay
Lot size:
0.08 Acres
Year built:
1940
Courtesy: EXP Realty, LLC 888-860-7369
View additional info

ADDITIONAL INFORMATION

Calling all investors, second-home seekers, and visionaries—this is the project you’ve been waiting for! AND it just got better with a price improvement!! Located just steps from the water in the charming community of Idlewilde, this 2-bedroom cottage-style home sits on a rare double lot with Chesapeake Bay views from the backyard and access to fantastic community amenities. While the property needs renovation—including electric installation, structural repairs, and cosmetic updates—the bones are there and the potential is undeniable. Whether you are looking to build instant equity, create a weekend getaway, or flip for profit, this home offers the canvas to make it happen. Enjoy the laid-back waterfront lifestyle with access to a community fishing pier, open lawn area, beach, and playground just down the street. A newer well is already in place, adding to the property's value and convenience. This is not just a project—it’s a chance to create something special in a peaceful coastal setting. Bring your vision, your toolbox, and your ambition. Properties with this kind of potential in Shady Side do not last. Schedule your showing today and turn this opportunity into your next success story. **Please note square footage is estimated, buyer to perform own due diligence**

Beds:
2
Baths:
2.00
Sq.Ft.:
1,000
Status:
Active
MLS#:
MDAA2116678
Type:
Single Family-Detached
Subdivision:
Idlewilde On The Bay
Lot size:
0.1 Acres
Year built:
1995
Courtesy: Taylor Properties 301-970-2447
View additional info

ADDITIONAL INFORMATION

Welcome to 1617 Winters Ave – Coastal Charm with Modern Updates in Idlewild on the Bay Beautifully updated and move-in ready, this 3-bedroom, 2-bath gem is nestled in the water-access community of Idlewild on the Bay. Situated just one block from the Chesapeake Bay, this home boasts fresh interior updates, a fully fenced yard, and two spacious decks ideal for entertaining or relaxing by the water. Step inside to find a light-filled living space with vaulted ceilings, gleaming hardwood floors, and a cozy wood-burning fireplace. The open-concept kitchen has been refreshed with white cabinetry, updated hardware, a stylish butcher block island, and walkout access to the upper deck. Highlights Include: Upgraded kitchen with modern butcher block island and white cabinetry Vaulted ceilings and large windows for abundant natural light Two full bathrooms with updated vanities, including a soaking jacuzzi tub Upper and lower decks perfect for grilling, entertaining, or unwinding under the trees Spacious primary bedroom with walkout access to the yard Energy-efficient washer/dryer (2023) in a convenient laundry closet Fully fenced yard with a charming patio and garden area Idlewild amenities: beach access, pier, playground, clubhouse, and boat ramp access Enjoy the peaceful, coastal lifestyle with the convenience of being just a short drive from Annapolis and less than an hour to D.C. or Baltimore. This home combines the best of comfort, style, and Chesapeake Bay living. ?? 1617 Winters Ave – Your updated escape by the Bay is waiting. Schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,176
Status:
Active
MLS#:
MDAA2114456
Type:
Single Family-Detached
Subdivision:
Columbia Beach
Lot size:
0.19 Acres
Year built:
2004
Courtesy: Schwartz Realty, Inc. 301-261-9700
View additional info

ADDITIONAL INFORMATION

Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond from the rear and views of the Chesapeake Bay from the front. Enjoy watching local waterfowl and soaking in the natural beauty from every angle. Inside, the spacious kitchen opens to the family room, perfect for gathering, along with a formal living room and a main-level office or potential 5th bedroom. Upstairs features four bedrooms, including a primary suite with views of both the Bay and Flag Pond, plus an en-suite bath, three additional bedrooms, and a full hall bath. A two-car garage includes an extra storage room. Brand new a/c. While the home could use some updating and TLC, it presents a fantastic opportunity to make it your own. Located in a vibrant waterfront community with amenities such as a boat ramp, pier, tennis courts, and more. Come experience the Chesapeake Bay lifestyle.

Beds:
5
Baths:
5.00
Sq.Ft.:
5,151
Status:
Active
MLS#:
MDAA2110798
Type:
Single Family-Detached
Subdivision:
Shady Side
Lot size:
0.91 Acres
Year built:
2007
Courtesy: Monument Sotheby's International Realty 410-525-5435
View additional info

ADDITIONAL INFORMATION

Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering two hundred and seventy feet of private shoreline and breathtaking views. Designed for refined living and effortless entertaining, this home delivers an exceptional lifestyle both inside and out. The exterior is a private resort, featuring a heated in-ground pool, outdoor grilling area, fire pit, kayake launch and impeccably landscaped grounds. A private pier with a boat lift provides direct access to the water, making this the perfect setting for boating enthusiasts and those seeking tranquility by the shore. Inside, the home is richly appointed with custom finishes and a spacious open-concept design. The gourmet kitchen offers premium appliances, custom cabinetry, and expansive water views that flow into the main living and dining areas. Every detail has been thoughtfully curated for both function and elegance.The bathrooms have been recently remodeled with luxurious, spa-inspired touches. The primary suite is a sanctuary, complete with a serene spa-like bath, walk-in shower, soaking tub, and private access to an outdoor sauna — your personal retreat just steps from the bedroom. Additional highlights include a new roof, upgraded geothermal HVAC system for efficient, year-round comfort, and a three car garage with ample storage space. Whether you’re hosting guests, spending weekends on the water, or simply enjoying peaceful moments at home, this extraordinary property offers the perfect blend of sophistication, comfort, and waterfront charm.

Beds:
2
Baths:
1.00
Sq.Ft.:
900
Status:
Active
MLS#:
MDAA2118814
Type:
Single Family-Detached
Subdivision:
Columbia Beach
Lot size:
0.09 Acres
Year built:
1982
Courtesy: Long & Foster Real Estate, Inc. 410-224-0600
View additional info

ADDITIONAL INFORMATION

Welcome to this delightful coastal cottage nestled in the heart of the Columbia Beach community! Spacious wide beach, tot lot, tennis courts and basketball too. This beautifully updated home perfectly balances modern comfort with timeless charm. Offering two spacious bedrooms and a full bath, the layout is thoughtfully designed for easy living and effortless style. Winter peek-a-boo waterview too! Step inside to find gleaming hardwood floors and an updated kitchen featuring brand-new stainless steel appliances and generous storage space. New roof (2023). The new kitchen has stainless appliances from the range and hood to the refrigerator and oven. Kitchen cabinets with lazy Susan, contemporary hardware, and quartz countertops. New skylights and many brand-new windows. 5 ceiling fans. Situated on a picturesque level yard showcases lush landscaping in both the front and side, and a koi pond in the front. Best of all, is the back deck ready for entertaining or enjoying peaceful outdoor moments. As a resident of Columbia Beach, you’ll enjoy exclusive access to the Chesapeake Bay—perfect for fishing, boating, or simply soaking in the serene waterside atmosphere. Community amenities include a private boat ramp, pier, playground, and basketball and tennis courts, enriching your waterfront lifestyle. Sit on the new deck and watch the sunsets, or grab your kayak and go to the community beach, or even closer, Franklin Point State Park. Swim, tan on the sand beach, or go fishing. So much new in this clean and updated Columbia Beach cottage. This isn't just a home—it's a lifestyle. Don't miss your chance to own a piece of Chesapeake Bay charm. Schedule your private tour today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,244
Status:
Active
MLS#:
MDAA2109400
Type:
Single Family-Detached
Subdivision:
Columbia Beach
Lot size:
0.12 Acres
Year built:
1955
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Great New Price ... here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay year round. This Bay fronting property has an open airy interior, warm and inviting, with two story vaulted ceilings, walls of windows which showcase the Bay view. The ease of main level living, enhanced with wood floors, includes the living, dining, kitchen, 2 bedrooms, a full bathroom, and laundry . Take advantage of the loft, with it’s natural light, perfect for a home office or studio. Plus a half bathroom and additional storage. Enjoy seamless indoor – outdoor living, expanded with a new low maintenance deck. Perfect for morning coffee and entertaining on the bay. Replaced: Deck in 2024.. Sump Pump and exterior faucet 2024.., Main level bathroom 2020.. Leaf Filter Gutter Guards , 2019,.. Split 2018.. Bedroom windows, 2016.. Roof, 2014 . Upper half bathroom added in 2009. Situated in the gated water privileged community of Columbia Beach. The community offers residents opportunities for boating, fishing, and other recreation: boat launch, short fishing pier, a long pier, waterfront park, children’s play area, regulation size basketball court, and tennis. The community walking path, along the rocks that line the cove, is marked by oval signs featuring a swan. Vacation Year Round ! Estimated : Annapolis- 18 mi Andrews AFB- 25 mi Joint Base Andrews- 34 mi Washington D.C.

Beds:
9
Baths:
7.00
Sq.Ft.:
9,325
Status:
Active
MLS#:
MDAA2112580
Type:
Residential
Subdivision:
Idlewilde Acres
Lot size:
0.69 Acres
Year built:
2004
Courtesy: RE/MAX One 410-535-6291
View additional info

ADDITIONAL INFORMATION

Welcome to an extraordinary waterfront estate offering the perfect balance of luxury, function, and efficiency on Maryland’s treasured Western Shore. This 9-bedroom, 6.5-bath residence spans 8,400+ square feet and is built to withstand the elements while embracing the serene lifestyle of the Chesapeake Bay. Set on over 2/3 of an acre with 260 feet of water frontage, this solid brick & block home was constructed with reinforced steel walls, high R-value insulation, a poured concrete foundation, and a roof system designed to withstand high winds – all topped with 40-year architectural shingles (inspected Nov. 2024). This is a true fortress disguised as a coastal retreat. Inside, you’ll find three full-size primary suites with private baths, a massive 3,200+ sqft basement for entertaining or storage, and energy-efficient systems throughout: geothermal heating and AC, multiple radiant and baseboard heating zones, and a combination of solar, propane, oil, and electric systems—keeping average monthly electric costs to just $165. The home also features six 80-gallon water heaters and 3 backup AC systems for ultimate comfort and efficiency. Need room for guests or passive income potential? The spacious guest wing with a separate entrance, two bedrooms, full kitchen, private bath, and a large water-view balcony is perfect for visiting friends, multi-generational living, or Airbnb. The property has two full-size laundry rooms. Additionally, with its expansive layout and abundance of private suites, this home is ideal for assisted living or multi-family use, offering flexibility for a range of living arrangements or care services. Step outside to your 2024-renovated 250’ pier with 8’ deep water, heavy electric service, two boat lifts, two jet ski lifts, and room to add more. Shady Side is a charming and peaceful bayfront community just a short ride to Annapolis, with convenient access to Washington, DC, and Baltimore. Locals enjoy crabbing, fishing, waterfront parks, scenic trails, and the neighborly vibe of this Southern Anne Arundel County gem. This is a rare chance to own a high-performance home with panoramic views, protected shoreline, and multi-generational living opportunities—all in a sought-after Chesapeake Bay setting.

Beds:
5
Baths:
6.00
Sq.Ft.:
9,040
Status:
Active
MLS#:
MDAA2111342
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.96 Acres
Year built:
1955
Courtesy: Real Broker, LLC - Annapolis 855-450-0442
View additional info

ADDITIONAL INFORMATION

Merchant Unmatched water views. Over 8,000 sq ft of curated living. A property that doesn’t just stand out—it stands alone. Tucked away in the quiet, rural charm of Shady Side, this architecturally bold residence offers year-round views of the West River and a lifestyle that feels worlds away—yet keeps you close to everything that matters. Step inside and you’re immediately immersed in nearly 8,000 square feet of living space—designed with intention, filled with original art, historical artifacts, and featured in multiple publications for its distinctive character. This, all because this home, this masterpiece, boasts design elements created by one of the world’s most renowned artists. From the banquet-sized dining room to the grand living space that opens to the water, every room delivers scale, flow, and timeless style. The chef’s kitchen anchors the home with form and function, while five spacious bedrooms and 5.5 baths offer more than enough room to retreat away for moments of relaxation and peace. Outside, an acre of manicured gardens and carefully curated sculptures surrounds the home—offering a peaceful backdrop for everything from morning coffee to sunset wine. And with no HOA, this is freedom at its finest. Just off the beaten path, yet only minutes from the dockside restaurants of Deale, the historic charm of Galesville, and the energy of Annapolis—with a surprisingly easy commute to DC and Baltimore—this home offers a balance few properties can match. Offered with the ability for the new owner to keep much of the furnishing and art pieces (to be negotiated with offers), this home isn’t just a place to live—it’s a place to belong. Live bold. Live different. Welcome home.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,051
Status:
Active
MLS#:
MDAA2105584
Type:
Residential
Subdivision:
Cedarhurst On The Bay
Lot size:
0.11 Acres
Year built:
1965
Courtesy: Long & Foster Real Estate, Inc. 410-535-1000
View additional info

ADDITIONAL INFORMATION

Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with Architectural shingles in 2018. It has an oversized 1 car garage with workshop for storage for those handyman/handywomen projects. Sale contingent on owner finding a home of their choice and they may need a rent back to make that work. New photos will be coming!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,920
Status:
Active
MLS#:
MDAA2104698
Type:
Condo
Subdivision:
Avalon Shores
Lot size:
0.34 Acres
Year built:
2005
Courtesy: Redfin Corp 301-658-6186
View additional info

ADDITIONAL INFORMATION

PRICE REDUCED! Waterfront Stunner! This home features main-level living with a large bedroom and full bath. The kitchen opens to the living area with tons of natural light. Upstairs, two additional bedrooms with private baths ensure everyone has their own space & privacy. Outside is a small finished entertainment area or walk to your private dock. Crab in the summer or take a kayak, SUP, or canoe out for a sunset paddle. New Roof in 2024. Make sure to see this house before it's gone! Flood Insurance Required- Flood Zone AE. $135 annual Civil Owners Association is included with the taxes. It covers road maintenance, the two playground parks, and the boat ramp maintenance.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,600
Status:
Active
MLS#:
MDAA2105408
Type:
Residential
Lot size:
1.6 Acres
Courtesy: Next Step Realty 443-901-2200
View additional info

ADDITIONAL INFORMATION

Welcome to this incredible home to-be-built on 1.6 waterfront acres just south of Annapolis. This waterfront lot offers breathtaking West River Views, a deep-water pier, two docks and two boat lifts that convey. Located in shady Side, this property offers the best of both worlds; quiet, small-town charm with easy access to Annapolis and DC. Proposed home is by Whitehall Building, a premier waterfront builder in the Annapolis area. While the design is already thoughtfully planned, you have the unique opportunity to personalize selections and make modifications, ensuring your home fits your vision. Surrounded by estate homes, the drive-in is picturesque, setting the tone for this exceptional property. If you're looking for stunning waterfront and privacy without the hustle of city life, this is it. Ready to build your dream home?

Beds:
1
Baths:
1.00
Sq.Ft.:
948
Status:
Active
MLS#:
MDAA2101548
Type:
Residential
Subdivision:
Regulars
Lot size:
0.23 Acres
Year built:
1940
Courtesy: Premiere Realty LLC 703-748-0001
View additional info

ADDITIONAL INFORMATION

Welcome to 1419 Shady Rest Rd, it located on a quiet street not far from the water in one of Maryland’s Chesapeake Bay boating communities. This property has a drive way with plenty of space for parking. Being sold AS IS. Priced to sell so schedule your showing today! Please contact Torrence Hall for showings..

Beds:
4
Baths:
2.00
Sq.Ft.:
2,144
Status:
Active
MLS#:
MDAA2011224
Type:
Single Family-Detached
Subdivision:
Shady Side
Lot size:
0.57 Acres
Year built:
1940
Courtesy: Schwartz Realty, Inc. 301-261-9700
View additional info

ADDITIONAL INFORMATION

4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MA2) marine zoned property, totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8feet, that can accommodate boats in excess of 40 feet. Total income from 7 of the 12 slips in 2021 was $11,300. POTENTIAL $20,000 PLUS RENTAL INCOME IN ADDITION TO DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. Cold box has been removed.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Shady Side 20764 Real Estate

Shady Side is located in Maryland. Shady Side, Maryland 20764has a population of 4,813. Shady Side 20764 is less family-centric than the surrounding county with 24.21% of the households containing married families with children. The county average for households married with children is 33.77%.

The median household income in Shady Side, Maryland 20764 is $118,125. The median household income for the surrounding county is $108,048 compared to the national median of $69,021. The median age of people living in Shady Side 20764 is 49 years.

Shady Side Weather

The average high temperature in July is 87.3 degrees, with an average low temperature in January of 28.2 degrees. The average rainfall is approximately 44.8 inches per year, with 12.7 inches of snow per year.

Shady Side Map

Shady Side Real Estate Market Conditions

  • Median sales price

    $440,000
    10.7%
    change since last quarter
  • # Active listings

    78
    30-day change

Shady Side Schools and Demographics

Education near Shady Side, MD

City County
High School Graduates 98.49 93.4
College Degree - 2 year 5.81 7.6
College Degree - 4 year 36.58 42.9
Graduate Degree 8.28 14.03
Expenditures per Student 17,686 17,686
Students per Teacher 13.8 13.8

Elementary Schools near Shady Side, MD

Grades Students P/T Ratio ZIP
Broadneck Elementary School KG - 05 772 18.2 21012
Central Elementary School KG - 05 656 14.4 21037
Davidsonville Elementary School KG - 05 680 17.5 21035
Deale Elementary School KG - 05 283 13.9 20751
Edgewater Elementary School KG - 05 525 16.4 21037
Germantown Elementary School PK - 05 749 14.5 21401
Hebron - Harman Elementary School PK - 05 779 17.1 21076
High Point Elementary School PK - 05 671 17 21122
Hilltop Elementary School PK - 05 699 14.3 21061
Marley Elementary School PK - 05 724 15.6 21060
Mayo Elementary School KG - 05 317 15.2 21037
Monarch Academy KG - 08 676 14.8 21060
Nantucket Elementary School KG - 05 746 17.3 21114
Piney Orchard Elementary School KG - 05 675 17.2 21113
Rippling Woods Elementary School PK - 05 665 16.8 21061
Seven Oaks Elementary School PK - 05 723 17.9 21113
Shady Side Elementary School PK - 05 484 15.7 20764
Solley Elementary School PK - 05 739 17.6 21060
Southgate Elementary School PK - 05 716 17.2 21061
Traceys Elementary School KG - 05 382 15.7 20779

Middle Schools near Shady Side, MD

Grades Students P/T Ratio ZIP
Arundel Middle School 06 - 08 941 15.3 21113
Central Middle School 06 - 08 1,056 16.4 21037
Chesapeake Bay Middle School 06 - 08 1,048 13.9 21122
Crofton Middle School 06 - 08 1,104 16.5 21054
George Fox Middle School 06 - 08 930 15 21122
Lindale Middle School 06 - 08 896 12.6 21090
MacArthur Middle School 06 - 08 1,025 12.4 20755
Old Mill Middle North 06 - 08 921 14.1 21108
Severn River Middle School 06 - 08 778 16.2 21012
Severna Park Middle School 06 - 08 1,442 16.9 21146
Southern Middle School 06 - 08 764 14.6 20711
Wiley H. Bates Middle 06 - 08 850 11.2 21401

High Schools near Shady Side, MD

Grades Students P/T Ratio ZIP
Annapolis High School 09 - 12 1,813 14.5 21401
Arundel High School 09 - 12 2,021 19 21054
Broadneck High School 09 - 12 2,104 18.4 21409
Chesapeake High School 09 - 12 1,434 15.4 21122
Glen Burnie High School 09 - 12 1,931 16 21060
Meade High School 09 - 12 2,070 16.2 20755
North County High School 09 - 12 2,013 16.5 21061
Northeast High School 09 - 12 1,335 17.3 21122
Old Mill High School 09 - 12 2,105 16.7 21108
Severna Park High School 09 - 12 1,872 18.8 21146
South River High School 09 - 12 2,210 17 21037
Southern High School 09 - 12 1,071 16.5 20776

Ungraded Schools near Shady Side, MD

Grades Students P/T Ratio ZIP
* Anne Arundel Evening High 09 - 12 192 21146
Center of Applied Technology-North UG - UG 0 0 21144
Center of Applied Technology-South UG - UG 0 0 21037
Central Special School PK - 12 130 6.1 21037
Chesapeake Science Point 06 - 12 462 14.5 21076
Marley Glen School PK - 12 77 3.4 21060
Mary E. Moss Academy 09 - 10 57 4.1 21032
Phoenix Academy 01 - 12 357 11.2 21401
Ruth Parker Eason School PK - 12 106 4.2 21108

Demographics near Shady Side, MD 20764

Zip Code City
Neighborhood Type Small town
Population 4,813 584,064
Population Density 724 1,408
Median Age 49 38.5
People per Household 2.4 2.6
Median Household Income 118,125 108,048
Average Income per Capita 62,685 51,113

Real estate near Shady Side