Shady Side MD Historical Real Estate, Homes for Sale

OPPORTUNITY IN AVALON SHORES! Welcome to 6264 Shady Side Road in Shady Side, Maryland! This 3-bedroom, 2-full-bath ranch-style home offers approximately 1,432 square feet of above-grade living space, plus a full basement, situated on a 0.39-acre lot. Built in 1966, the property features an attached garage, wood-burning fireplace, electric heating, window-unit cooling, and a spacious yard. The home is serviced by a private well and public sewer. PROPERTY IS BEING SOLD STRICTLY AS-IS. The home is dated and requires repairs and updating, presenting an opportunity for buyers looking to renovate and personalize a property or investors seeking their next project. IMPORTANT PROPERTY INFORMATION: The property is currently occupied, including two rooms rented under informal arrangements without written leases. Buyers should verify occupancy arrangements and conduct their own due diligence regarding the property’s condition, systems, and intended use. Showings are available on Saturdays and Sundays by confirmed appointment only. Please do not disturb occupants. Located in the Avalon Shores community, this property offers an opportunity to create value in an established Shady Side neighborhood. Schedule your showing and explore the potential!

6264 Shady, Shady Side

Listing courtesy of Keller Williams Legacy. Contact:

$345,000

2 Beds ⋅ 1 Baths

This ranch-style residence, built in 1964 and the original owner, set on a sprawling 1-acre lot that backs to serene trees and boasts river views from the front yard. The property features a brick front and shingle siding. This home has1,636 square feet of finished living space. The open layout connects the dining and living areas, enhanced by elegant wood floors and built-in cabinetry. A cozy wood-burning fireplace serves as a focal point, perfect for creating a warm ambiance during cooler evenings. The eat-in kitchen is equipped with essential appliances including a single oven, electric cooktop, and refrigerator, complemented by ample table space for casual dining. The home features two bedrooms a full bathroom featuring a tub shower combination and ceramic tile accents. Additional highlights include ceiling fans for optimal airflow and an attic for extra storage. Outside the expansive lot offers a level terrain with a front yard, rear yard, and side yards, ideal for outdoor activities or potential landscaping projects. A large shed provides additional storage solutions, while the gravel and stone driveway accommodates multiple vehicles, including an attached carport. Enjoy the tranquility of nature with picturesque views of the river, creating a peaceful backdrop for relaxation or entertaining.

4891 Idlewilde Rd, Shady Side

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

$749,900

4 Beds ⋅ 2 Baths

Come Live the Bay Lifestyle! Welcome to 1244 Pine Avenue, a charming Chesapeake Bay retreat in Shady Side, Maryland, offering beautiful water and marina views, exceptional outdoor living, and the relaxed charm of coastal Maryland. Wake up to breathtaking sunrises, watch sailboats pass by, and enjoy peaceful evenings overlooking the bay. Located in the desirable Cedarhurst community, this inviting home offers the perfect opportunity to embrace waterfront living with a residents only marina across the street. Inside, the light filled living and dining areas feature a fireplace and expansive picture windows framing beautiful water views. The updated kitchen is appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range. Just beyond, a charming screened-in porch creates the perfect setting for morning coffee or al fresco dining. The spacious rear family room offers additional living space with sweeping bay views and sliding glass doors opening to the deck and fully fenced backyard, creating a seamless connection between indoor and outdoor entertaining. The main level includes a versatile bedroom ideal for guests or a home office, while upstairs, three generously sized bedrooms offer comfortable accommodations, including a spacious primary bedroom with beautiful Chesapeake Bay views. Additional highlights include a newer roof, new washer and dryer, generous outdoor entertaining areas, and a large storage shed is wired and has electricity. For boating enthusiasts, the nearby residents only marina offers boat slips reportedly available for $350 annually, providing convenient access to the Chesapeake Bay. Cedarhurst's waterfront community center, playground, beach, and picnic areas further enhance the neighborhood's coastal lifestyle. Whether as a primary residence or weekend retreat, 1244 Pine Avenue offers an exceptional combination of water views, generous outdoor living, boating access, and the tranquility of Shady Side's beloved Chesapeake Bay community.

1244 Pine Ave, Shady Side

Listing courtesy of Compass. Contact:

$349,900

3 Beds ⋅ 3 Baths

MECHANICS/WORKSHOP DREAM. Nestled in the serene Shady Side community, this charming ranch-style home offers a perfect blend of comfort and functionality. With 1,489 square feet of thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm and welcoming interior, highlighted by a cozy breakfast area and a combination kitchen/dining space that encourages gatherings. The kitchen is equipped with stainless steel appliances, including a gas oven/range and a convenient dishwasher, making meal prep a delight. Enjoy the ease of main-floor laundry and the comfort of ceiling fans throughout. The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and a spacious lot of over half an acre that backs to lush trees, providing a tranquil backdrop. Outdoor living is enhanced by a charming patio and porch, perfect for morning coffee or evening relaxation. The property also includes an oversized detached garage with car lift and a shed, offering ample storage and workspace. Perfect for the mechanic with side jobs or projects to work on. Parking is a breeze with a circular gravel driveway and additional spaces for guests or projects. This home is not just a place to live; it's a sanctuary where you can unwind and create lasting memories. Experience the perfect blend of indoor comfort and outdoor beauty in this delightful property.

1462 Columbia Beach Rd, Shady Side

Listing courtesy of RE/MAX Realty Group. Contact:

$410,000

3 Beds ⋅ 3 Baths

NEW PRICE IMPROVEMENT + SELLER-OFFERED INTEREST RATE BUYDOWN CREDIT! Completely Rebuilt. Beautifully Reimagined. Coastal Living at Its Finest. Welcome to 4922 Dogwood Street, a stunning 3-bedroom, 2.5-bath cottage in the waterfront community of Avalon Shores in Shady Side, Maryland. Thoughtfully redesigned from the studs up, this home blends modern sophistication with relaxed Chesapeake Bay charm, offering the perfect combination of style, quality craftsmanship, and peace of mind. Now offered at an improved price, with a seller credit toward an interest rate buydown to help make homeownership even more affordable! Every inch of this home has been transformed, creating a fresh, contemporary retreat with a warm, inviting aesthetic. The bright, open-concept floor plan showcases beautiful hardwood flooring throughout, solid wood interior doors, and a carefully curated palette that strikes the perfect balance between modern cottage and coastal sophistication. At the heart of the home, the brand-new kitchen features crisp white shaker cabinetry, sleek quartz countertops, and a complete new appliance package. Designed for both everyday living and effortless entertaining, the open layout creates a seamless flow between the kitchen and living spaces. The spacious primary suite offers a private, beautifully appointed bathroom with custom tilework and a stylish vanity. Two additional bedrooms feature ceiling fans and share a thoughtfully designed connecting bathroom, providing comfort and functionality for family or guests. Beyond the beautiful finishes, this home offers the confidence of an extensive, top-to-bottom renovation. Taken down to the studs, improvements include: • Brand-new roof, siding, gutters, and Pella windows • Completely updated electrical wiring and upgraded electrical panel • All-new plumbing, HVAC equipment, and ductwork • New insulation and drywall throughout • Waterproofed crawlspace • Beautiful hardwood flooring and custom-tiled bathrooms • Brand-new kitchen and appliance package, including washer and dryer • Solid wood interior doors and ceiling fans in every bedroom • New asphalt driveway, bluestone patio, and bluestone entry steps with iron railings Situated on a generous double lot, the property offers exceptional outdoor space for entertaining, gardening, recreation, or simply enjoying the peaceful coastal setting. Located on the scenic West River and Chesapeake Bay peninsula, Avalon Shores captures the charm of Maryland’s waterfront lifestyle. Residents enjoy a community park, baseball field, and proximity to boating, fishing, crabbing, marinas, Franklin Point State Park, and spectacular Chesapeake Bay sunsets. Why settle for an ordinary renovation when you can own a home that has been completely reinvented? With its extensive upgrades, oversized double lot, desirable waterfront community setting, new price improvement, and seller-offered rate buydown credit, 4922 Dogwood Street presents an exceptional opportunity to enjoy turnkey coastal living. Move right in, unpack, and start enjoying the Chesapeake lifestyle!

4922 Dogwood St, Shady Side

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

$399,000

2 Beds ⋅ 1 Baths

This delightful 1930s ranch-style cottage offers a perfect blend of vintage charm and modern comfort. Set on a generous 1.25-acre lot, the property boasts ample outdoor space, ideal for gardening, entertaining, or simply enjoying the tranquility of nature. An inviting outbuilding adds versatility, whether you envision a workshop, studio, or extra storage space. The expansive driveway ensures convenient parking for you and your guests, making gatherings a breeze. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by the beauty of your own private oasis. With two cozy bedrooms and a well-appointed full bathroom, this home is designed for comfort and ease. The layout encourages a warm, inviting atmosphere, perfect for creating lasting memories. This property is not just a house; it's a place where you can truly feel at home. Embrace the opportunity to make this charming cottage your own and enjoy the serene lifestyle it offers. Don't miss your chance to experience the perfect blend of comfort and outdoor living!

4924 Kellam Rd, Shady Side

Listing courtesy of District Pro Realty. Contact:

$625,000

4 Beds ⋅ 2 Baths

There is something special about life near the Chesapeake Bay—and 1221 Bast Lane captures it beautifully. Completely remodeled from top to bottom, this charming one-level Coastal Craftsman combines fresh, sophisticated interiors with incredible outdoor space and one of the most impressive detached garages you will find. Set on a beautiful lot just shy of an acre in Shady Side, the home offers four bedrooms and an easy, comfortable floor plan filled with natural light, beautiful windows, gorgeous flooring, and thoughtful finishes throughout. At the heart of the home is a stunning gourmet kitchen featuring beautiful cabinetry, warm butcher-block countertops, stainless steel appliances, a stylish backsplash, generous workspace, and a fresh coastal aesthetic that makes the entire space feel inviting. The primary suite is a wonderful retreat with an enormous walk-in closet and a sleek, spa-inspired bath featuring a beautiful walk-in shower with glass doors. Additional bathrooms carry the same clean, sophisticated design, while the incredible laundry room proves that even the most practical spaces can be beautiful. Step outside onto the spacious deck and imagine summer dinners, weekend cookouts, morning coffee, or a glass of wine as the sky changes color at sunset. The huge yard offers nearly an acre to spread out, garden, play, entertain, or simply enjoy having space around you. And then there is the garage. More than 1,500 square feet of detached garage and workspace with THREE bays and electric creates an absolute dream setup for car enthusiasts, collectors, hobbyists, contractors, or anyone who wants room for vehicles, tools, storage, and projects without sacrificing the house or yard. The home and garage roofs date to 2023, along with the home's siding. Beyond the property, Shady Side delivers the Chesapeake lifestyle people fall in love with: water views, beautiful sunsets, neighbors walking their dogs, kids playing, and the relaxed sense of community that makes evenings feel a little slower and weekends feel a little longer. Here, you can enjoy the character of a coastal community while coming home to a beautifully renovated property where the transformation has already been completed. Beautiful inside, extraordinary outside, and filled with unexpected features, 1221 Bast Lane isn't simply move-in ready—it's the kind of place that makes you excited to come home.

1221 Bast Ln, Shady Side

Listing courtesy of Coldwell Banker Realty. Contact:

$365,000

2 Beds ⋅ 2 Baths

Welcome to this charming 2-bedroom, 2-bath rambler in the desirable water community of Westelee. This well-maintained home offers comfortable one-level living with an inviting kitchen, spacious living areas, and a large yard ideal for outdoor entertaining, gardening, or relaxing. Cellar area has lots of room for storage or a work area with insulated walls. Recent updates include a new roof, electrical breaker panel, HVAC system, and hot water heater, well pump and appliances all completed in 2023. Both bathrooms have been updated for modern comfort and style. The voluntary community association provides access to a private beach, boat ramp, playground, pavilion, and pier. A wonderful opportunity for those seeking a move-in-ready home with plenty of outdoor space in a water-oriented community.

4911 Magnolia St, Shady Side

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

$299,900

4 Beds ⋅ 2 Baths

Welcome to this charming 4-bedroom, 2-bath home in the desirable Snug Harbor community of Shady Side. Offering approximately 1,930 square feet of living space, this property features a spacious layout, detached garage, and generous yard with plenty of room to enjoy outdoor living. Conveniently located near marinas, parks, local dining, and Chesapeake Bay recreation, this home presents a wonderful opportunity to enjoy the relaxed waterfront lifestyle with easy access to Annapolis. This property has an exclusive boat slip!

1704 Maryland Ave, Shady Side

Listing courtesy of Sell Your Home Services. Contact:

$249,900

1 Beds ⋅ 1 Baths

This is an estate sale. Buyer to verify all information. Cute 1 BR 1BA cottage located a few hundred yard from the bay. Needs some TLC but livable. Roof is less than 7 years old. Solar panels are owned and not leased. Includes boat slip number 7. Would make a great getaway home or investment property. Sold strictly "as is". Seller will make no repairs.

1737 Cedar Ave, Shady Side

Listing courtesy of RE/MAX Realty Plus. Contact:

$300,000

3 Beds ⋅ 3 Baths

Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the surrounding landscape while taking advantage of the area's relaxed coastal lifestyle. Whether you're looking for a primary residence, a weekend retreat, or an investment opportunity, this property provides a wonderful chance to create your vision in a desirable Anne Arundel County location. Don't miss the opportunity to explore the possibilities this home has to offer. Some photos contain virtual renovation and staging.

6372 Shady, Shady Side

Listing courtesy of Maryland Realty Connection. Contact:

$699,000

3 Beds ⋅ 3 Baths

***OPEN HOUSE SAT 9/12 11am-1pm***Welcome to the Honey Hole of the South Creek! New roof & gutters freshly installed! 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 kayak, canoe, paddleboard, or boat, while the nearby community marina provides access to deep-water slips for larger vessels. Residents also enjoy access to the community beach, making every day feel like a vacation. An added bonus is the inclusion of the adjacent Lots 17 & 18 (4907 Thomas Drive), providing additional privacy, flexibility, and future possibilities. Step inside to discover a bright, open floor plan designed to maximize both the water views and natural light. The spacious kitchen features a center island, ample cabinetry, and a sunny breakfast area highlighted by a large picture window overlooking the creek—an unforgettable place to enjoy your morning coffee. The adjoining living room offers the warmth and charm of a wood-burning stove along with sliding glass doors leading to the expansive wraparound screened porch, creating the perfect space for indoor-outdoor entertaining or simply relaxing while watching osprey, herons, and other local wildlife. Large pantry area for additional storage and separate dining room for additional room to spread out. Upstairs, all three bedrooms are thoughtfully situated, including a spacious primary suite that serves as a true waterfront sanctuary. Wake up each morning to panoramic water views from your private balcony, then unwind in the en-suite bath featuring a walk-in closet and plenty of room to recharge after a day on the water. The additional bedrooms are generously sized, with one also enjoying beautiful water views, and are served by a second full bathroom on the upper level. This home has been thoughtfully updated for peace of mind and long-term enjoyment. It may say it was built in 1941, but this home went through an extensive remodel in 1991 taking the original beach bungalow to the oversized colonial it is today. Recent improvements include a brand-new roof (2026), renovated Tigerwood deck, and a professionally encapsulated crawlspace complete with a dehumidification system. If you’ve been dreaming of a waterfront lifestyle that combines privacy, natural beauty, and everyday comfort, this is a rare opportunity to own a special piece of Southern Anne Arundel County. Whether you’re boating, crabbing, kayaking, entertaining on the screened porch, or simply enjoying the peaceful creek views, you’ll quickly understand why this location is so special.

1241 Johnson Dr, Shady Side

Listing courtesy of RE/MAX One. Contact:

$765,000

3 Beds ⋅ 2 Baths

Waterfront living with a private dock—all for only $765,000! Get a lower mortgage payment! Seller willing to supplement rate discount, 2-1 Buydown: 2% lower interest rate in Year 1, and 1% lower in Year 2. 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, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There’s extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious fully-fenced backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage with a 12kW Level 2 EV charger, offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

4950 Bonniewood Dr, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$450,000

3 Beds ⋅ 2 Baths

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 hardwood floors throughout and a spacious layout designed for both comfortable living and entertaining. The oversized 21’ x 23’ primary suite offers a true retreat with plenty of room to unwind, while the additional bedrooms are generously sized as well. The main level features a versatile gym/office space that could easily serve as a fourth bedroom, guest room, or playroom depending on your needs. The heart of the home is the large eat-in kitchen with ample space for gathering, complemented by a separate formal dining room and an expansive family room featuring a cozy wood-burning fireplace. Major updates include a new roof installed in 2020, offering peace of mind for years to come. Conveniently located in a USDA-approved area, this home also qualifies for 100% financing eligibility for qualified buyers. If you’ve been searching for spacious living paired with a sought-after water lifestyle, this Cedarhurst gem checks all the boxes.

1217 Pine Ave, Shady Side

Listing courtesy of RE/MAX One. Contact:

$695,000

Endless potential in this versatile C1-zoned property — live in one side and run your business from the other, or use the entire building for commercial use. Originally the Shady Side Post Office, this character-filled building sits on just over half an acre with approximately 400 feet of road frontage, offering excellent visibility and easy access. Highlights: C1 commercial zoning — flexible uses Live/work configuration or full commercial conversion Multiple offices / bedrooms 3 Bath rooms 2 kitchens and 2 laundry areas Just over 0.5 acre lot with 400' road frontage Suitable for: accountant, attorney, construction office, daycare, antiques, boat sales/service, retail, studio, café, professional offices, and more Why this property: Great exposure and versatility make this an ideal opportunity for owner-operators or investors looking to attract customers and create a distinctive business presence. High frontage and flexible zoning mean almost any business concept could work here.

6285 Shady, Shady Side

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

$399,900

4 Beds ⋅ 2 Baths

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 and shower combination. The bright kitchen shines with white cabinetry and brand new, never used stainless steel appliances, giving it a clean, fresh feel. The living room opens to the fenced backyard and patio through a sliding glass door, inviting easy indoor and outdoor living. Just one step down from the living room is a private office with double doors, its own half bath, and access to the laundry and utility room, offering flexible space for working from home, hobbies, or guests. Outside, the circular driveway provides generous parking, and the backyard shed adds convenient storage for beach chairs, bikes, and lawn equipment. BOAT SLIPS AVAILABLE

1199 Oak Ave, Shady Side

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

$669,500

4 Beds ⋅ 2 Baths

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 accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$669,500

4 BEDS/1FULL BATH AND1/2 BATH WITH SHOWER. 2144SQ FT. Home income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MC) heavy commercial 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 8 feet that can accommodate boats in excess of 40 feet. Total income from 6 of the 12 slips in 2025 was $6900!! POTENTIAL for much more PLUS Additional rental income from DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. .

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

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