156 properties for sale in Old Bayside

Welcome home to Chesapeake Beach! Tucked away on over an acre in the town limits of Chesapeake Beach, this adorable 3-bedroom, 2.5-bath home offers the perfect blend of privacy, nature, and small-town coastal living. Step inside to a welcoming open floor plan with comfortable living spaces designed for everyday living and entertaining. The kitchen features French doors opening to a side deck that leads to the large back deck, creating an easy connection between indoor and outdoor living. Upstairs, you'll find two spacious bedrooms, while the fully finished walk-out basement offers a third bedroom with French doors opening directly to the patio, along with a spacious open living/recreation area. The flexible lower level provides plenty of space for guests, a family room, home office, recreation area, or whatever your lifestyle needs. Enjoy your morning coffee on the covered front porch, or head outside and enjoy the peaceful surroundings from the spacious decks and patio. Mature trees a

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

You won't believe your eyes when you see what you can have for a low price of $699,500! What a deal! The views are way more spectacular than even the photos show you! Being an end unit you get double the Chesapeake Bay Views! And you even have 3 different outdoor sitting areas that are all Bay Front! Why live in an ordinary home when you can live on the Water Front! Rich solid bamboo flooring flows throughout the main living areas, while replacement windows maximize the breathtaking Bay views. The remodeled gourmet kitchen features quartz countertops, stainless steel appliances, and opens to a full-width waterfront deckperfect for morning coffee, outdoor dining, or simply watching the boats pass by. The spacious family room also opens onto a private waterfront deck, creating seamless indoor and outdoor living. Upstairs, the primary suite becomes your personal waterfront retreat with its own private deck overlooking the Chesapeake Bay, beautifully updated bath, and the convenience of a

Beach-Town Retreat with New Roof, New HVAC (2023) & No Town Taxes! Welcome to this charming 3+bedroom, 2.5-bathroom home located just moments from the vibrant North Beach boardwalk! Enjoy the ultimate beach-town lifestyle with a massive financial perk: this property sits right outside the official town limits, meaning you pay no additional town taxes while still enjoying close proximity to the water, dining, and shops. New flooring (2026) in Living room, kitchen and Baths. The main level features a relaxing, screened porch perfect for your morning coffee and enjoying coastal breezes. Step down to lower deck with hot tub and spacious fenced yard with shed. Downstairs, the fully finished lower level is built for gathering with friends, featuring a built-in bar area ready for hosting game days or weekend guests! This level also includes a dedicated home office/denideal for remote work, a hobby room, or a private guest space. New water treatment system (2025) Schedule your tour today!

Tucked away on a private flag lot in the sought-after Richfield Station community, this 4-bedroom, 3.5-bath Colonial offers something difficult to find in a larger neighborhood: privacy, space, and a peaceful setting away from the main road. The home provides approximately 2,372 square feet of total finished living space, including a fully finished lower level that offers flexibility for guests, a recreation room, home office, or additional living space. Step outside to the deck, replaced in 2023, where you can relax or entertain while enjoying the private surroundings. The retaining wall was also rebuilt at that time. The sellers have completed several valuable improvements, including a re-shingled roof in 2025, a new HVAC system installed in 2021, and LeafGuard gutter covers added in 2021. All windows and sliding doors were replaced in 2018 and include a transferable lifetime warranty for the new owners, subject to the warranty providers terms. Richfield Station remains a favorite fo

A Million-Dollar View at a Price Within Reach! Imagine waking up to the beauty of the Chesapeake Bay every day without the million-dollar price tag! Begin your mornings with coffee on your balcony as the sun rises over the Bay. Unwind in the evening as colorful skies reflect across the water, creating a peaceful backdrop to everyday life. This isn't just a home; it's a waterfront lifestyle you'll look forward to coming home to. This spacious 1,100-square-foot, 2-bedroom, 2-bath condominium offers an exceptional opportunity to enjoy waterfront living in a gated, full-service community. Step onto your balcony, accessible from both the spacious primary bedroom and living room and take in panoramic views of the Chesapeake Bay. Whether you're enjoying a quiet morning, entertaining friends or simply watching the ever-changing scenery, this is a view that never gets old. And the lifestyle extends well beyond your front door. Enjoy an impressive collection of community amenities, including a r

A Letter From the House, Dear Future Owner, I am waiting for the right person to come along. Ive been lovingly cared for by the same family since I was built. My owners customized my floor plan during construction to suit the way they wanted to live and those decisions still make a difference. Step through my front door and notice my gracious sense of space. A two-story foyer and open main level create an easy flow between living, dining and kitchen areas while allowing each space to retain its own character. The Heart of the Home: My kitchen is where I truly shine with the generous cabinetry and counter space, a professional-style gas range, and a substantial center island. The large window above the sink brings in natural light, while the island naturally becomes the gathering place for family and friends. The family room offers a quieter kind of comfort, especially with the gas fireplace glowing on a cool evening. And when the weather is beautiful, simply open the patio door and my

Welcome to 2550 Woodland Place, a professionally landscaped end-unit townhouse in the sought-after Richfield Station community of Chesapeake Beach! With over 1,800 square feet of living space, this three-bedroom home offers one full and two half bathrooms, a one-car garage, a spacious deck, and a fully fenced backyard. The main level provides a comfortable layout for everyday living and entertaining, while the lower level features a spacious family room with a cozy fireplace and walkout access to the backyard. The freshly sanded and stained deck is ready for summer BBQs and gatherings, and the garage's built-in cabinetry provides convenient additional storage. Recent updates include fresh paint throughout, new flooring, and new carpet. Richfield Station offers multiple playgrounds and tot lots, along with basketball and tennis courts, making it a great community for enjoying time outdoors. Conveniently located near the Chesapeake Beach boardwalk, beaches, shopping, and restaurants, the

Welcome to 2630 Richfield Lane in the desirable Richfield Station community of Chesapeake Beach. Offering 4 bedrooms, 2.5 baths, a 2-car garage, and more than 2,200 square feet of living space, this home gives you plenty of room to spread out while enjoying everything the Chesapeake Beach area has to offer. Several of the major improvements have already been completed, including a newer roof and siding, updated appliances, luxury vinyl plank flooring, and fresh paint. Giving the next owner a strong head start while still leaving opportunities to personalize the home and make it their own. The main level offers a spacious layout with multiple living areas, a kitchen with center island, and access to the rear deck and backyard. Upstairs, youll find four bedrooms, including a generously sized primary suite. The unfinished lower level provides even more possibilities for future living space, a home gym, office, recreation area, workshop, or additional storage. Situated on over half an acre

Modern living, generous space, and the relaxed charm of North Beach come together in this beautifully maintained home built in 2020. Offering 4 bedrooms, 2 full and 2 half baths, a partially finished basement, attached garage, and an expansive fenced backyard, this home delivers space and versatility. From the moment you arrive, the homes welcoming exterior and covered entry set the tone. Inside, rich wood flooring, soft neutral finishes, and an abundance of natural light create a warm, polished atmosphere. The spacious open-concept living area is made for gathering, with plenty of room for everything from quiet evenings at home to entertaining family and friends. With four bedrooms, theres flexibility for overnight guests, home offices, or whatever your lifestyle requires. The homes bathrooms offer a fresh, contemporary feel with crisp finishes, stylish vanities, and beautiful tile flooring. The partially finished lower level adds even more usable space and endless possibilitiescreate

Location, location, location! Just five blocks from the Chesapeake Bay, this charming three-bedroom cottage puts the beach, boardwalk, and favorite local restaurants within an easy stroll. Bring your vision and give this diamond in the rough the love and attention it deserves. With a little imagination, you can create your own slice of bayside paradise. Beach passes are available. Live music, Farmer's markets, beaches, parks, boardwalk, restaurants, stores all within walking distance. Close to Marinas, community centers, Rod & Reel offers concerts, a hotel and restaurants. A new water park is currently under construction as an added bonus. Easy commute to DC, Virginia, Annapolis and More

Welcome to waterfront living at Horizons on the Bay! This 2-bedroom, 2-bath condo offers the opportunity to enjoy beautiful Chesapeake Bay views from a well-appointed condo building in the heart of Chesapeake Beach. The open setting and waterfront surroundings create a relaxing atmosphere, while the communitys amenities make everyday living feel like a getaway. Residents enjoy a rooftop pool with sweeping Bay views, fitness center, private pier, library, community gathering spaces, and a picnic area with grills and firepit. The gated community is conveniently located near the Chesapeake Beach boardwalk, beaches, restaurants, shops, parks, and local entertainment. Enjoy easy access to waterfront recreation while remaining within reach of Annapolis, Washington, D. C. and surrounding areas. Whether you're looking for a full-time residence, weekend retreat, or low-maintenance waterfront lifestyle, Horizons on the Bay offers a unique opportunity to enjoy life on the Bay

Simply Magnificent Chesapeake Bay View Lot! Pictures can not do it justice! Great community of Holiday Beach located in Chesapeake Beach brings memories of small beach towns where everyone knew their neighbors and went boating and fishing together. This lot is not only a one of a kind, it has had so much development work done, it is now ready for you to start building your own custom home. The structure for the permit shows a dwelling that is 36 foot by 41 feet (foot print of existing foundation) in size or 1476 sq ft. The permits have been pulled for demolition of the walls, permit for the septic has been approved, permit for the well has been approved and grading permits are done. The lot consists of lot 19 and 20 as well as the existing gravel driveway to the left of the structure. All 3 parcels are in the selling price along with all the permits to get started. Homes in the community range from small cottages in need of complete renovation to home over a million dollars on the wate

Welcome to 8445 Clear Spring Drive, where updated living, a flexible floor plan, and a peaceful wooded setting come together in the heart of sought-after Richfield Station! Offering three finished levels, 4 bedrooms, and 3.5 baths, this spacious townhome gives you plenty of room to spread out while keeping everyday life comfortable and convenient. The main level feels bright and inviting with an easy flow designed for both everyday living and entertaining. At the heart of the home is the gourmet kitchen, featuring rich black cabinetry, newer appliances, ample counter space, and plenty of storage in the pantry. Whether you're making dinner on a busy weeknight or gathering with friends and family, there's room to cook, entertain, and actually enjoy the space. The adjoining living and dining areas make it easy to stay connected, while views of the woods behind the home create a peaceful backdrop that's hard to beat. Upstairs, the deluxe primary suite gives you a private place to unwind at

Welcome to 804 Beach Ave, a charming Bayside home offering beautiful Bay views and a fantastic North Beach location! This 3 bedroom, 3 bath detached home features approximately 1,692 square feet of comfortable living space with a bright and inviting layout. Enjoy a spacious kitchen with granite countertops and a breakfast area, along with a cozy living room featuring a fireplace. The primary bedroom offers wonderful water views and access to a private balcony, creating the perfect place to relax and enjoy the coastal setting. Located just steps from the water and waterfront park, with convenient access to the marina, town beach, boardwalk, restaurants, shops, and everything North Beach has to offer. Enjoy the charm of waterfront living and the Bay lifestyle from this beautifully situated home!

Charming beach cottage. With stunny views of the bay-2000 sq ft. Of living space with breath taking views. Great for someone that would like to host an Airb&b Business, downsize or retirement cottage. This is one of the largest lots in Rosehaven/Holland Point (800 Walnut Ave. Lot 37 must convey with lots: 34,35,36). The kitchen features stainless steel appliances, granite countertop's breakfast bar, wine fridge, ceramic tile flooring and backsplash. Two huge bedrooms two full baths with walk in shower and soaking tub. Propane fireplace decking and additional shed with off street parking. Window facing the bay have been replaced, new water softener

Enjoy coastal living in North Beach! This beautifully refreshed 4-bedroom, 3-bath Colonial is ideally situated close to the Chesapeake Bay, offering the perfect blend of comfort, style, and location. With spacious living areas, four well-appointed bedrooms, and a classic Colonial layout, there is plenty of room to relax, entertain, and make yourself at home. Recent updates include new luxury vinyl plank flooring and carpet throughout, fresh paint, new quartz countertops and new kitchen appliances, giving the home a clean, move-in-ready feel. Conveniently located near the Chesapeake Bay, local restaurants, shops, boardwalk and all that North Beach has to offer, this home is a wonderful opportunity to enjoy the charm of waterfront living without being directly on the water. Don't miss your chance to make this North Beach gem your own!

Seller Offering Closing Help w/Accepted Offer*Welcome to coastal living at its finest! This beautifully updated 3BD/2BA home blends modern luxury with everyday comfort. The large kitchen features upgraded quartz countertops, stainless steel appliances, and island, flowing seamlessly into the spacious living room with lots of natural light and luxury vinyl plank flooring throughout. Unwind in the spa-inspired bathrooms or relax on the private screened porch after a day at the beach. Situated on a large double corner lot, this home offers a fully fenced yard with plenty of room for outdoor living, entertaining, pets, or play. Ideally located just minutes from the boardwalk, restaurants, shopping, and entertainment, this home offers the perfect combination of luxury, convenience, and coastal charm. Whether you're searching for a full-time residence, vacation getaway, or an investment opportunity, this is one you won't want to miss!

Chesapeake Bay Views, Coastal Charm, and the Best of the Twin Beaches Lifestyle! Imagine starting your mornings with a cup of coffee overlooking the Chesapeake Bay and ending your evenings relaxing on your deck, enjoying the coastal breezes and beautiful water views. Welcome to an exceptional opportunity to embrace the waterfront lifestyle in the heart of Chesapeake Beach! Tucked away in a small, quiet townhome community, this charming home offers the perfect combination of coastal living, modern updates, and an unbeatable location. With Chesapeake Bay views from nearly every room, you'll enjoy a daily reminder of just how special life along the Bay can be. Inside, you'll find a beautifully updated kitchen, tastefully renovated bathrooms, and gorgeous hardwood floors throughout the main living area. The inviting interior offers warmth, character, and comfortable living spaces designed to make you feel right at home. One of the property's most appealing features is its incredible outdoo

Located in Owings on the North Beach line, this freshly painted two-story home with a walkout basement offers comfort, convenience, and coastal living in a sought-after school district. Situated on a quiet cul-de-sac, the property is just minutes from shopping, restaurants, the public beach and pier on the Chesapeake Bay. The kitchen and bathrooms feature granite countertops, stainless steel appliances, LVP flooring, and recessed lighting. French doors lead to a spacious screened porch overlooking the large backyard with mature hardwoods and a new rear fence, all set on nearly one acre. The home also features a spacious owners suite with walk-in closet and private bath, generously sized secondary bedrooms, a finished walkout basement, and a welcoming wrap-around porch perfect for relaxing and enjoying the peaceful setting. Recent update: The seller has installed brand-new carpet in the primary bedroom on the stairs, both upstairs and downstairs. Also, the seller installed LVP flooring

Welcome to 8962 Chesapeake Lighthouse Drive! This three-bedroom, two-bath end-unit townhome, built in 1992, offers approximately 1,726 square feet of total living space. The main level features wood flooring, crown molding, and a comfortable eat-in kitchen, creating a warm and welcoming setting for everyday living. The finished lower level provides additional flexible living space with a comfortable recreation room and walkout access to the private fully fenced backyard. Ideal for entertaining, relaxing, pets, or play. PRICED TO SELL, this home also boasts numerous recent improvements, including brand-new windows installed in September 2026, updated siding 2018, new front and patio doors 2024, and a privacy fence and deck added in 2023. Two designated parking spaces add everyday convenience. Conveniently located near North Beach, with easy access to restaurants, shopping, waterfront recreation, and commuter routes to Washington, D. C. Joint Base Andrews, and other major employment cent

Welcome to this beautifully maintained. *3-level Colonial*. Situated on a spacious. *corner lot*. In the desirable community of Owings, Maryland. Offering an exceptional floor plan with generous living space, this home features. *4 bedrooms, 3.5 bathrooms*, and a fully finished basement designed for comfortable living and entertaining. *Just minutes away from Colonial Beach*. The. *main level*. Offers a unique and functional layout featuring. *three spacious bedrooms*, a full bathroom, a formal. *living room*, elegant. *dining room*, a bright. *breakfast nook*, and a. *large open kitchen*. Equipped with. *stainless steel appliances*, abundant cabinetry, and ample countertop space. Step outside to the impressive. *full-length rear deck*. That spans the width of the homeperfect for entertaining, relaxing, or enjoying peaceful outdoor views. Occupying the. *entire upper level*, the private. *owner's suite*. Serves as a true retreat, offering plenty of space for a sitting area, generous cl

Bring Your Vision and Unlock the Possibilities! Nestled in the charming North Beach Park community, this 3-bedroom, 2-bath Cape Cod is brimming with potential and ready for its next chapter. Offering picturesque views of the marsh and a peaceful coastal setting, this home presents a wonderful opportunity to create something truly special. Whether you're looking for a primary residence, a weekend getaway, or your next renovation project, this property is the perfect canvas to bring your ideas to life. With a little imagination and some TLC, you can transform this home into your very own coastal retreat. Enjoy the natural beauty of the surrounding marshland and the relaxed atmosphere of the North Beach area. This is your chance to take a home with character and make it your own. Bring your contractor, your creativity, and your visionthe possibilities are endless! Property is being sold strictly AS-IS

Welcome to this bright and airy end-unit townhome in the Richfield Station community of Chesapeake Beach. Sun-filled living spaces include a beautiful kitchen with an island and stainless-steel appliances that opens to the dining area and a spacious living room. The home backs onto serene, mature trees, filling the interior with abundant natural light through multiple windows and doors that lead to the deck. Located on a quiet, non-through street with minimal traffic, this residence offers peaceful everyday living. Condo association fees offer true low-maintenance convenience, covering trash service, lawn maintenance, and exterior maintenance. The roof was replaced in 2026. Richfield Station residents enjoy direct access to the Chesapeake Beach Railway Trail system and the Fishing Creek Boardwalk. You are just minutes from the Chesapeake Bay, its scenic boardwalk, beaches, restaurants, and the full'Bay Life' lifestyle. Calvert County provides convenient access to the region's major met

Nestled in the charming Richfield Station Village, this delightful Colonial townhouse offers a perfect blend of comfort and style. Built in 2007, the home features a warm and inviting interior, highlighted by beautiful flooring and recessed lighting that create a cozy ambiance throughout. The spacious living area seamlessly flows into a dining area, ideal for gatherings and entertaining. The well-appointed kitchen boasts an island, perfect for casual meals or meal prep, and comes equipped with essential appliances including a built-in microwave, electric oven/range, and refrigerator. A pantry provides additional storage, ensuring your kitchen remains organized and functional. Upstairs, you'll find three generously sized bedrooms, providing ample space for relaxation and personalization. Outside, the property is enhanced by well-maintained sidewalks, inviting you to enjoy leisurely strolls in the neighborhood. An attached garage with a garage door opener offers secure parking and extra

A whole lot of charm in the quaint waterfront town of North Beach! This home is ready for someone with a little vision and creativity to bring it back to life. Whether you're looking for a weekend getaway, or a place to call home, there's plenty of potential here! Enjoy being just a short distance from the Chesapeake Bay, North Beach's sandy shoreline, boardwalk, fishing pier, local restaurants, and shops. With water behind the property too, and the charm of a coastal community all around, it's easy to imagine the possibilities

More Phots to come*. Nestled in the charming North Beach Park community, this delightful Colonial-style home offers a perfect blend of comfort and modern living. Built in 2002, this detached residence boasts 1,702 square feet of thoughtfully designed space, ideal for creating lasting memories. Step inside to discover a warm and inviting interior featuring beautiful wood floors and new kitchen cabinets and countertops. The traditional floor plan includes a spacious family room that opens to the eat-in kitchen, making it the perfect spot for gatherings and casual dining. The kitchen is equipped with essential appliances, including a built-in microwave, electric oven/range, dishwasher, and refrigerator, ensuring that meal preparation is a breeze. Enjoy your morning coffee in the cozy kitchen nook or at the table space, where natural light pours in. This home offers three comfortable bedrooms, including a primary suite with a generous walk-in closet and an en-suite bathroom. With two full

Step right into this charming bay retreat located just 3 blocks from the Chesapeake Bay. Very tastefully renovated. This spacious cottage offers 2 good sized bedrooms and one smaller room perfect for an office/playroom/music room etc. There is a separate dining space and laundry. Enjoy socializing with the community while sitting on the front deck or keep things quiet and private in one of the 2 rear hang out areas, the 4 season room or the cute fire pit and grilling area. This home offers many major upgrades. They are as follows: water heater 2019 siding 2021 blow in insulation in the attic 2021 Hvac 2021 appliances 2022 rebuilt stoop 2024 electrical upgrade and removal of obsolete wiring 2025 sewer connection redone 2022 side door and slider 2021

Sellers offering $8,000 for closing help or interest rate buydown! Welcome to 3705 10th Street in North Beach, where coastal-town charm, generous outdoor space, and thoughtful updates come together in one beautifully maintained home! Situated on a spacious double lot, this property offers extra space between neighboring homes for a more open, private feel while still being close to everything North Beach has to offer. Step inside to a bright, welcoming interior featuring fresh paint throughout, warm vinyl plank flooring, freshly shampooed carpets, and comfortable living spaces. The kitchen features white cabinetry, granite countertops, stainless steel appliances, and a newer stove/range and brand new dishwasher. The dining room flows seamlessly into the family room, creating an inviting layout for everyday living and entertaining. Upstairs you'll find three spacious bedrooms, including a primary bedroom with a recently refreshed en-suite bath, plus an updated full hall bath. The fully