Shady Side Homes with Colonial Style

Shady Side Homes with Colonial Style

Welcome to Shady Side, Maryland, a charming waterfront community nestled in the heart of Anne Arundel County. Known for its picturesque views and serene atmosphere, Shady Side offers a unique blend of coastal living and small-town charm. With the Chesapeake Bay just a stone's throw away, residents enjoy easy access to boating, fishing, and breathtaking sunsets that paint the sky in hues of orange and pink.

Shady Side is not only a haven for nature lovers but also a place where history and architectural beauty come together. One of the standout features of this delightful community is its collection of stunning Colonial-style homes. These timeless residences are characterized by their symmetrical facades, classic brick exteriors, and elegant columns, evoking a sense of history and sophistication. Many of these homes have been lovingly maintained, showcasing original features while incorporating modern amenities for today’s discerning buyers.

Living in Shady Side means embracing a lifestyle that values community and connection. Neighbors often gather at local events, farmers' markets, and waterfront parks, fostering a sense of belonging that is hard to find elsewhere. Whether you’re drawn to the charm of Colonial architecture or the allure of waterfront living, Shady Side offers a welcoming environment that feels like home.

Explore the beauty and tranquility of Shady Side, where the past meets the present, and find your dream Colonial-style home today. Your perfect blend of history, community, and natural beauty awaits!

Newest Shady Side Homes with Colonial Style

4 Beds ⋅ 3 Baths

Professional photos & video coming 8/10. Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintained and truly move-in ready, this exceptional property combines luxury, comfort, and the best of coastal living. The main level features beautiful hardwood floors, a spacious gourmet kitchen with granite countertops, stainless steel appliances, and an open layout overlooking the inviting family room with a gas fireplace and spectacular Bay views. A main-level bedroom and full bath provide the perfect accommodations for guests. Upstairs, you'll find three additional bedrooms and two full baths, including a stunning waterfront primary suite. Wake up each morning to endless water views through walls of glass, then step onto your private covered terrace to enjoy your morning coffee while watching the sunrise over the Chesapeake Bay. Outside, your private pier offers the perfect place to fish, crab, or take the boat for a day on the water. Cruise to the many nearby waterfront restaurants and marinas, or simply relax and enjoy the peaceful waterfront setting. Conveniently located with an easy commute to Annapolis, Washington, D.C., and Baltimore, this remarkable home is nestled in the charming waterfront community of Felicity Cove. If you've been dreaming of exceptional Chesapeake Bay waterfront living, this is a home you won't want to miss.

4721 Oak Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

4 Beds ⋅ 3 Baths

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 island with breakfast bar area! The open flow from the kitchen to dining area and then into the living area with corner gas fireplace in view, is a dream! The upper level features large bedrooms and the owners suite features a walk-in closet with built-ins and luxurious bath with double vanity and glass-enclosed tile shower! The additional bedrooms are designed to allow the Sunlight in with the central bath having a dual vanity as well. Come enjoy all the amenities this neighborhood has to offer, like the community Beach, playground areas, dock and boat ramp for accessing South Creek and the Rivers and Bay! You will know you are home when you arrive, come take a look!

1316 Juniper St, Shady Side

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

3 Beds ⋅ 3 Baths

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. 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. 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: 4105356291

3 Beds ⋅ 3 Baths

Welcome to this charming home located in a sought-after water-privileged community, just a short walk to the beach, boat slips, playground, boat ramp, and other neighborhood amenities. The main level features a spacious primary suite with a private full bath, offering convenient one-level living. The beautifully appointed kitchen boasts a center island with a gas cooktop, wall oven, abundant cabinet space, and a bright dining area. The kitchen opens seamlessly to the spacious living room, highlighted by a cozy gas fireplace and engineered hardwood flooring throughout the main level. Step outside through the kitchen slider to a wonderful screened porch, the perfect spot to relax and enjoy the outdoors. An adjoining rear deck overlooks the fully fenced backyard, providing plenty of space for entertaining, pets, or play. Upstairs, you'll find two additional bedrooms connected by a convenient Jack-and-Jill bathroom. Ideally located for an easy commute to both Washington, D.C., and the Annapolis area, this home also qualifies for 100% financing through the USDA Rural Development loan program, making homeownership even more attainable. 24hr. showing notice is required.

1161 Steamboat Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

3 Beds ⋅ 3 Baths

Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball court, and picnic areas. Conveniently located near local marinas, waterfront dining, parks, and Chesapeake Bay attractions, with easy access to Annapolis, Edgewater, Washington, D.C., and Baltimore. A great opportunity to enjoy a water oriented lifestyle in one of Southern Anne Arundel County's popular waterfront communities.

4909 Olive St, Shady Side

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

4 Beds ⋅ 3 Baths

Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new water softener / well pump (relocated to garage), and 66-gallon water heater. 2025 - replaced roof, replaced HVAC, Primary bathroom renovation (cabinet, vanity, shower, upgraded flooring, replaced toilet, fogless mirror), and replaced dryer vent. Don't miss the opportunity to purchase this stunning home sitting on a 1-acre natured filled lot. Please schedule all showings via Showing Time.

1582 Snug Harbor Rd, Shady Side

Listing courtesy of Maryland Waterfront Properties LLC. Contact: 7036281386

3 Beds ⋅ 3 Baths

Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. Situated on over one-third of an acre, this well-maintained 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, space, and community living. The fully fenced backyard provides an ideal setting for entertaining, family gatherings, or simply relaxing outdoors. Inside, the updated kitchen features granite countertops and stainless steel appliances, while gorgeous hardwood floors with custom inlay accents add warmth and character throughout the home. The spacious primary suite boasts vaulted ceilings and a private en-suite bath, creating a comfortable retreat. All bedrooms are generously sized and offer ample closet space. Enjoy peaceful mornings with a cup of coffee or unwind in the evenings on the charming enclosed front porch, perfect for reading or taking in the neighborhood atmosphere. Residents of Avalon Shores enjoy exceptional community amenities, including two playgrounds, baseball fields, a community boat launch, and water access. Opportunities like this are rare in such a desirable waterfront community. Don't miss your chance to make this wonderful home your own!

4951 Bonniewood Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

3 Beds ⋅ 2 Baths

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

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: 4105356291

3 Beds ⋅ 2 Baths

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 upgraded appliances, modern cabinetry, and beautiful hardwood floors, creating a bright and inviting space for cooking, gathering, and unwinding. Step out onto the large deck for effortless entertaining, with plenty of parking for guests. Two sheds! Vinyl fenced in flat back yard! Wake up to sunrise views from the upper level decks or take a short stroll to the community dock for a peaceful moment by the water. This water privileged neighborhood is perfect for year round living or a budget friendly bayside retreat. Launch your kayak or boat for days on the Bay, explore nearby marinas and yacht clubs, or enjoy local waterfront restaurants, dock bars, and scenic parks. Conveniences along Shady Side Road and Snug Harbor Road keep daily life simple, and commuting to D.C., Andrews AFB, or Annapolis is a breeze. This home conveys as a “Marina Association Slip Holder Member,” giving you full access to the revitalized marina and boat ramp.

4912 Mariners Dr, Shady Side

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

3 Beds ⋅ 3 Baths

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 kitchen, boasting sleek white cabinetry, premium quartz countertops, and matte black fixtures, all set against striking herringbone plank flooring. The spacious living area features hardwood flooring and French doors that open to your back deck—perfect for indoor-outdoor entertaining. Bathed in natural light, the home leads you upstairs to a serene primary suite and two additional bedrooms. This turn-key gem is the retreat you’ve been waiting for. Schedule your tour today and start living the Bay life!

1527 Lincoln Rd, Shady Side

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

4 Beds ⋅ 3 Baths

AUGUST DELIVERY! Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry. A main-level home office or flex room provides the ideal space for working from home or relaxing. Upstairs, the owner's suite features a large picture window, an expansive walk-in closet, and a spa-inspired bath with a luxury shower. Just a short walk from the community center and playground, residents enjoy Cedarhurst's rare four acres of community-owned waterfront with panoramic Chesapeake Bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and opportunities to watch sailboats, waterfowl, and local watermen at work.

1225 Juniper St, Shady Side

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

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