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**
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!
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.
Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combined living and dining rooms to the nice sized kitchen with appliances and main level bedroom and bath. There is a full bath on each level and three more bedrooms on the upper level. The sunroom with wide windows and lots of natural light has a great view of the backyard and leads to the rear deck, which is a perfect spot for outdoor fun. The rear exterior includes a 3-car detached garage with large workshop and an unfinished upper level. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side attractions. NOTE - Buyers winning the Highest & Best must understand that they participated in a Highest & Best, Multiple Offers Situation and that any requests to the Seller for Special Concessions, Repairs or Switch in Financing could result in the Seller terminating and retaining Buyer's EMD.
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.
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!
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.
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.
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.
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!
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.
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?
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..
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.
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.
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.
