Shady Side Real Estate

Shady Side Real Estate

Welcome to Shady Side, a hidden gem nestled in Anne Arundel County, Maryland. This charming waterfront community offers the perfect blend of tranquility and convenience, making it an ideal place to call home.

Shady Side boasts a rich history dating back to the 1600s when it was first settled. Today, it is a vibrant and close-knit community that prides itself on its natural beauty and small-town charm. With its picturesque views of the Chesapeake Bay and abundance of outdoor recreational activities, Shady Side is a paradise for nature lovers and outdoor enthusiasts.

Residents of Shady Side enjoy a laid-back lifestyle while still being within easy reach of urban amenities. The community is home to a variety of local shops, restaurants, and community events, creating a strong sense of community spirit.

Whether you're looking to relax on the beach, explore hiking trails, or enjoy fresh seafood at a waterfront restaurant, Shady Side has something for everyone. With its friendly atmosphere and stunning waterfront setting, it's no wonder that Shady Side is a sought-after destination for those looking to escape the hustle and bustle of city life.

Come and discover the beauty and charm of Shady Side – where small-town living meets waterfront paradise.

Newest Listings in Shady Side

$379,000
3 Beds ⋅ 3 Baths
Professional photos coming soon! Primary suite with vaulted ceilings & attached full bath. Eat in kitchen opens to the family room. Generous sized bedrooms upstairs. Avalon Shores community offers water oriented amenities for you to enjoy. Bring your boat, jet ski and kayaks. The boat launch ramp is available for community members. Use the community pier or sandy beach for a wonderful day spent by the Chesapeake Bay. Multiple playgrounds as well! Stay tuned!

1248 Hawthorne St, Shady Side

Listing courtesy of RE/MAX One. Contact:

$314,900
3 Beds ⋅ 1 Baths
Nestled in the highly sought-after Avalon Shores waterfront community of Shady Side, this newly updated 3-bedroom, 1-bath cozy cottage offers the perfect blend of modern updates and timeless coastal charm! Step inside to discover beautifully refinished hardwood floors and fresh paint throughout, giving the home a bright and welcoming atmosphere. The kitchen has been upgraded with newly installed appliances, including a brand-new stainless-steel dishwasher, along with stylish black hardware and updated lighting. Situated on a .17-acre fenced-in lot, the expansive outdoor space is ideal for entertaining or enjoying peaceful coastal evenings. Step outside into your oversized screened-in porch and freshly painted, multi-level wrap-around porches, providing plenty of outdoor living space. Need additional storage? A large 12x12 shed with 220v electricity is perfect for extra storage, a workshop, or even a home gym—the possibilities are endless! The recently completed landscaping not only adds curb appeal but also creates a blank canvas for you to add your personal touch. Enjoy easy access to the Avalon Shores community beach, pier, boat ramp, playgrounds, and much more. Avalon Shores is conveniently located for easy commutes into D.C., Annapolis, Ft. Meade and Joint Base Andrews. This turn-key home is perfect for those who appreciate modern conveniences and the tranquil lifestyle of a waterfront community. Don’t miss out on this beautiful gem—make it your own today!

4912 Dogwood St, Shady Side

Listing courtesy of RE/MAX Gateway. Contact: (703) 652-5777
$310,000
3 Beds ⋅ 2 Baths
•••Offer Deadline Tues 10/8 at 12pm•••Welcome to this beautifully updated colonial home, offering 3 bedrooms and 1.5 baths. The spacious fenced-in rear yard is perfect for outdoor entertaining, and the extra-long paved driveway provides ample parking for guests. A massive shed/workshop offers plenty of space for projects or additional storage. Inside, the kitchen is finished with granite countertops and sleek white cabinets, blending modern style with functionality. This home is located in an incredible community that features a boat launch, a community pier perfect for crabbing and fishing, and boat slips available for lease at just $600 a year, offering direct access to the Chesapeake Bay. The stunning community center boasts floor-to-ceiling windows with panoramic views of the bay, perfect for gatherings or relaxing available for lease only to community owners. Enjoy the nearby playground and picnic area for outdoor fun. To top it all off, this home is eligible for 100% financing with a no-down-payment program, making it an excellent opportunity for qualified buyers. Don’t miss your chance to live in this vibrant community with endless amenities!

1187 Pine Ave, Shady Side

Listing courtesy of RE/MAX One. Contact:

$439,999
3 Beds ⋅ 2 Baths
Welcome to 1552 Dennis Rd, a beautiful home constructed from the foundation up in 2002 and fully renovated in 2024. This 3-bedroom, 2-bathroom property offers one-level living with a versatile upstairs space that can be used as an additional bedroom, rec room, or office. The home features new flooring, a stunning modern kitchen with stainless steel appliances, quartz countertops, and new cabinets, as well as updated carpet and lighting throughout. Sitting on a private 1-acre lot, just 500 feet from the Chesapeake Bay and with Columbia Beach right behind the home, this is an ideal retreat for anyone seeking serenity and privacy. With a spacious layout, room for entertaining, and plenty of parking, this property is perfect for those looking to enjoy peaceful living by the bay while still having modern comforts. Don’t miss out on this unique opportunity to live by the water!

1552 Dennis Rd, Shady Side

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

$1,100,000
5 Beds ⋅ 4 Baths
Serenity & Space Await! This exceptional property, nestled on **5.96 private acres** and backing up to 68 acres of conservation land (no future building!), offers unparalleled privacy and tranquility. **Bonus Opportunity: With a full-price offer, the property comes with an extra 1.66-acre subdivided lot for future building development or investment potential! Step inside this 5-bedroom, 4-bathroom home and experience modern living at its finest: - Relax in the screened-in porch or entertain on the massive Trex deck and stamped concrete patio perfect for gatherings. - Expansive, lush yard space offers endless possibilities for outdoor fun and gardening. - Attached 2-car garage and 1 car detached garage for all your storage needs. New : A brand-new roof and Luxury vinyl tile (LVT) flooring throughout the home. Long driveway and exterior parking were just blacked topped a week ago. All new doors & trim, freshly painted walls and epoxy garage floor. Main-Level Bedroom en suite for easy access, plus a stunning Primary Bedroom upstairs featuring an en suite bath with radiant heated floors—a true retreat! Enjoy the community perks, including **beach access**, **boat ramp**, **play area**, and **boat slips**. For those who love the water, explore membership options at the **Chesapeake Yacht Club** or simply enjoy the **pool**. Don’t miss this rare opportunity to own a piece of paradise!

1200 Steamboat Rd, Shady Side

Listing courtesy of Home Towne Real Estate. Contact: (888) 225-2736
$339,500
2 Beds ⋅ 1 Baths
Recently renovated home in the water-privileged community of Avalon Shores. This beautiful property features a brand-new kitchen with stainless steel appliances, sleek white cabinets, and elegant granite countertops, along with fresh luxury vinyl plank flooring throughout. You'll appreciate the new HVAC system, updated electrical panel, fresh paint, new trim, and recessed lighting. The spacious rear deck is perfect for family gatherings. Plus, this home qualifies for 100% USDA Rural loan financing! Enjoy easy access to the community beach, pier, boat ramp, playground, and more. Conveniently located for a quick commute to D.C., Annapolis, Ft. Meade, and AFB.

1216 Avalon Blvd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$50,000
Vacant building lot located very close to the Chesapeake Bay and community park/pier. There previously was a house on the lot but it was removed. Buyer responsible for obtaining all information regarding building on this lot.

4718 Idlewilde Rd, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

$2,650,000
9 Beds ⋅ 7 Baths
Welcome to 4701 Girton Ave, an exceptional waterfront sanctuary offering breathtaking panoramic views of the Chesapeake Bay and West River. Situated on Curtis Point in Shady Side, this residence features 260 feet of pristine waterfront, a 250-foot pier with a boat lift and two jet ski lifts, and a convenient three-car garage. Enjoy the luxury within this expansive home, spanning over 8,400 finished square feet. The in-law suite, complete with its own kitchen, living room, two bedrooms, bathroom, balcony, and private entrance, offers an inviting retreat for guests. With a total of eight bedrooms and an optional office space that could easily convert into another bedroom, along with six and a half bathrooms, there's abundant space for all. The centerpiece of the home is the main kitchen, boasting direct water views and equipped with granite countertops, a gas cooktop, double ovens, and a Sub-Zero refrigerator—a chef's delight. The primary suite on the first floor features a walk in closet, a whirlpool tub, double sink vanity, and an indulgent 8-head shower. Separate laundry rooms on the main and top floors, along with ample storage throughout including in the basement, which offers 3,200 square feet of unfinished space, ensure convenience and functionality. Many of the bedrooms offer its own private balcony, providing a peaceful retreat. Outside, the back deck and expansive private waterfront yard offer the perfect setting for outdoor gatherings. With a private pier granting access to the water, enjoy fishing, boating, or simply soaking in the tranquil views. The property is conveniently located near marinas, waterfront dining, parks, and 20 - 45 miles from major cities such as Annapolis, Baltimore, and DC.

4701 Girton Ave, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$399,900
3 Beds ⋅ 2 Baths
One level living by the Bay! Check out this fully remodeled rancher just one block from the Chesapeake Bay. This 3 bedroom, 2 bath home has gone through an extensive renovation including all new windows, roof (architectural shingle), vinyl siding, doors, luxury vinyl plank flooring (Life Proof Product), kitchen cabinets, and appliances. All new central air and heat pump, new hot water heater, new gas range, ceiling fans in every bedroom with recess lights throughout the house. A large deck situated off the back of home includes a ramp leading to the spacious backyard. This home features a large primary suite with huge walk-in closet, sitting area, and full bath. Plenty of space to park a boat or trailer on the side of house. Large shed situated off the back side of property perfect for extra storage and yard equipment. Enjoy a quick walk to your community fishing pier, playground, kayak storage, and swimming beach. This area has an incredible view of the Chesapeake Bay and the Bay Bridge. The Idlewilde Civic League hosts yard sales, Easter egg hunts, Halloween activities with a haunted hay ride, pet photo shoots, community clean ups, outdoor movie nights, and more. The kayak rack storage is only $25 a year and has a great launch with protected access to the bay. The Idlewilde Restoration Beach is right around the corner and the perfect destination. This protected land is part of Anne Arundel County Parks and is called the "Shady Cove Natural Area" This is a great place to go by boat, kayak or take the hiking trails a couple blocks from the house. Discovery Village has a great public boat ramp (with 3 boat ramps) less than 2 miles from the house with plenty of parking and is free of charge.

4725 Girton Ave, Shady Side

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$659,900
4 Beds ⋅ 3 Baths
Enjoy breathtaking Chesapeake Bay views from this charming home in the quaint community of Felicity Cove. The ground level features a bedroom, a full bath, a living room, and a second kitchen—perfect for in-laws or guests. The main living area is situated on the second floor to maximize the stunning views and includes a sunroom off the primary kitchen, as well as the bedroom. The upper level is home to the primary bedroom with gorgeous bay views, a primary bath with a jacuzzi tub, and an additional guest bedroom. Experience year-round vacation living with access to the community pier and boat ramp.

4734 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$700,000
2 Beds ⋅ 1 Baths
Get away from the Rat Race and Make this your Own Private Retreat! 1337 West River Road , located in Shady Side, MD is a secluded waterfront property that sits on 1.5 acres with 592 feet of waterfront on the South Creek. This property has a home with 2 beds and 1 bath that will need remodeling and/or teardown. it's located 1/4 mile off the main road (West River Road ) follow signs to property. use GPS

1337 W River Rd, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$80,000
ONLINE AUCTION: Bidding begins 10/4 @ 10:00 AM. Bidding ends 10/8 @ 12:10 PM. List Price is Suggested Opening Bid. Deposit: $15,000. This approximately 1.90-acre lot of land is located in Shady Side, Maryland, within Anne Arundel County. Positioned just minutes from waterfront access to the Chesapeake Bay, this property offers potential for a serene living or development opportunity close to water-based activities. It provides easy access to the major traffic artery, W Shady Side Rd, facilitating convenient transportation options. Currently, the lot is vacant.

5170 Lake Ave, Shady Side

Listing courtesy of Ashland Auction Group LLC. Contact: (410) 488-3124
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