Bayside Real Estate

Bayside Real Estate

Welcome to Bayside, a picturesque subdivision nestled in the heart of the United States, where tranquility meets modern living. This charming community is designed for those who appreciate the beauty of nature while enjoying the conveniences of contemporary life.

Bayside boasts a stunning array of homes, each thoughtfully crafted to enhance the neighborhood’s appeal. From cozy single-family residences to spacious townhomes, there’s something for everyone in this vibrant community. The well-maintained streets are lined with lush greenery, creating a serene atmosphere that invites leisurely strolls and friendly conversations with neighbors.

One of the standout features of Bayside is its proximity to breathtaking waterfront views. Residents can indulge in leisurely afternoons by the bay, whether it’s fishing, kayaking, or simply soaking up the sun. The local parks are perfect for family picnics, weekend barbecues, and outdoor activities, making it an ideal place for families and individuals alike.

Bayside is also conveniently located near shopping centers, restaurants, and schools, ensuring that everything you need is just a stone’s throw away. The community prides itself on its strong sense of belonging, with regular events that bring residents together, fostering friendships and a supportive environment.

Whether you’re looking to settle down or invest in a property, Bayside offers the perfect blend of comfort, community, and natural beauty. Come explore this enchanting subdivision and discover why so many are proud to call Bayside home!

Newest Listings in Bayside

$599,000
3 Beds ⋅ 4 Baths
Are you ready to start living the Bayside Life? This newly offered GORGEOUS townhome is ready for its second owners! The lucky buyers of this fabulous 3 BR / 2+2 BA / 2-Car Garage home will experience the best location (directly across from SunRidge Pools/ SplashZone/ Tennis / Pickelball and Basketball Courts); while also enjoying a rare and beautifully landscaped wooded backyard. The original (and only) owners of this Freeman Townhome selected the rare first floor “Oasis Room” option at time of build (currently used as second living area and home office) with newly designed private powder room and bonus storage closet. The first two floors of the home have been updated with rich high-end LVP; 5.25” floor molding w/quarter round; 5” crown molding; recessed lighting; and painted throughout with consistent light, airy, neutral color palette (Benjamin Moore Seapearl, White Dove and Gorgeous White). The kitchen includes light colored cabinetry (Sherwin Williams Drift of Mist), perfectly matched no-seam quartz counters, beautiful glass backsplash, stainless outlet covers, and Samsung Gas Range. The fully remodeled second-floor powder room is exceptionally stylish with handsome vanity, unique mirror, lighting, fixtures and glass shelf all in a gray and brass scheme. Finally, six large windows and two glass French Doors provide magnificent natural lighting throughout the second floor. Upstairs, buyers will discover a King-Sized ensuite bedroom with walk-in closet; a Queen-Sized Bedroom w/walk-in closet; and a third bedroom currently furnished with two Twin beds. House includes five ceiling fans, new recessed lighting, and new kitchen light fixture. Significant portion of existing furniture will convey (please see or request copy of Listing Flyer for Property for detailed list of inclusions). Major Improvements Include: GE French Door refrigerator/freezer replaced 8/18. Provenza Maxcore LVP flooring on entire first and second floors (including stairs) and third floor bathrooms (4/21). Base trim with quarter round (5.25”) and 5” crown molding throughout first and second levels (4/21). Kraus “Kore” Workstation Undermount Stainless Steel 30” Single Bowl Sink with Integrated Ledge and Accessories (4/21). Samsung Gas Stove (4/21). Dual Carrier Gas Furnace/Air Conditioner Units (with Condensers/Evaporator Coil/Heat Pump/Air Handler) replaced 5/22. 75 Gallon Atmospheric Vented Hot Water Heater and GE Washer and Dryer replaced 1/24. GE Microwave replaced 5/24. Roof with transferrable warranty replaced (over entire row of townhomes) 5/25. Because words cannot accurately describe this beauty, this is a MUST SEE home! Final significant facts: This house has never been rented and, unlike most Bayside properties, the new owners will not be REQUIRED to purchase a Bayside Sports Membership. (Membership optional for Azalea Avenue townhomes.) Owner is licensed real estate agent in MD and VA only, and this home is offered as FOR SALE BY OWNER, but Seller will honor buyer agents.

36380 Azalea Ave, Selbyville

Listing courtesy of FSBO Broker. Contact: 7173947283
$410,000
3 Beds ⋅ 3 Baths
Welcome home to this beautifully updated end-unit townhome in the desirable Bayside community, facing a peaceful row of trees. This spacious three-level home offers an open, inviting layout, beautiful hardwood floors, and numerous recent updates. Enter from the main-level foyer into a spacious bonus room—perfect for a family room, home office, gym, or additional entertaining space. Step directly outside to the back deck, where you can enjoy grilling and entertaining while overlooking the large grassy common area. Upstairs, the open-concept main living level features a spacious living room with a gas fireplace and access to a second deck, a dining area, and an updated kitchen, all complemented by beautiful hardwood flooring. A convenient updated half bath completes this level. The top floor offers three generously sized bedrooms. The primary suite features a beautiful custom accent wall and an updated primary bath, creating a comfortable and stylish retreat. The updated hall bathroom serves the additional bedrooms. Recent major updates include a new HVAC system (2025) and a new hot water heater (2026). Condo replaced roof and skylight (2025) & power-washed exterior (9/2026). All providing added peace of mind for the next owner. Enjoy all that the Bayside community has to offer, including an outdoor pool, hot tub, tennis/pickleball courts, clubhouse with meeting/party room, and exercise room. The location is ideal for an active lifestyle, with a short walk to the Chester River, a local pub, the Cross Island Trail, and a marina. You'll also enjoy easy access to the Bay Bridge, restaurants, shopping, and all that Kent Island and Maryland's Eastern Shore have to offer. Move-in ready, beautifully updated, and perfectly situated—this Bayside townhome is ready to welcome you home!

510 Auckland Way, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$375,000
3 Beds ⋅ 4 Baths
Nestled in the prestigious Bayside community, this exquisite townhouse that was just updated and renovated in 2026 offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. With renovations completed in 2026, this home boasts modern elegance and thoughtful design throughout its 1,899 square feet. Step inside to discover a warm and inviting interior with all new luxury vinyl plank and ceramic tile flooring, featuring a floor plan that seamlessly connects the kitchen and living areas. The family room, conveniently located off the kitchen, is adorned with an electric fireplace, creating a cozy focal point for relaxation. The gourmet kitchen is a chef's dream that includes new quartz countertops, backsplash, new stainless steel appliances, built-in microwave, and a cooktop that promises culinary excellence. Ample storage and a spacious layout make meal preparation a delight. The home features three generously sized bedrooms, each designed with comfort in mind, including an updated primary suite with an luxurious walk-in shower, quartz countertops and new tile flooring. Enjoy the convenience of a fully finished basement with a walkout level, providing additional living space and easy access to the outdoors. The basement also includes garage access, ensuring practicality and ease of living. Step outside to your private deck, where the Chester River is just a short stroll away. The community offers an array of amenities, including a sparkling outdoor pool, tennis courts, and a clubhouse, fostering a vibrant social atmosphere. For those who enjoy an active lifestyle, bike trails and exercise rooms are readily available. Parking is a breeze with an attached garage and additional off-street spaces, ensuring ample room for guests. The meticulously maintained grounds, with included lawn care and snow removal, allow you to enjoy your surroundings without the hassle of upkeep. This property is not just a home; it's a lifestyle. Experience the tranquility of riverfront living while being part of a community that values both leisure and luxury. Embrace the opportunity to make this stunning townhouse your own and indulge in the exclusive lifestyle it offers.

512 Auckland Way, Chester

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

$599,900
3 Beds ⋅ 4 Baths
Experience Kent Island waterfront living in this beautifully appointed townhome in sought-after Bayside of Chester. The open-concept interior offers abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring generous cabinetry, ample counter space, and a large center island with seating that flows seamlessly into the dining and living areas. The spacious primary suite offers a walk-in closet and luxurious ensuite bath, while additional bedrooms and flexible spaces provide room for guests, a home office, or recreation. Enjoy TWO PRIVATE DECKS for outdoor dining, morning coffee, or relaxing in the peaceful surroundings. An attached garage, additional storage, and parking spaces across the street add convenience. Bayside amenities include a clubhouse, fitness center, pool, tennis courts, walking trails, and marina access. Castle Marina slips are available for short-term or annual rental, with select slips near Queens Landing potentially available for purchase. Close to waterfront dining, shopping, golf, and major commuter routes.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact: 3016586186
$595,000
3 Beds ⋅ 4 Baths
PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the Eastern Shore lifestyle! Beautiful hardwood floors flow throughout the main level, where the kitchen, dining room and family room all take advantage of the spectacular water views. The modern kitchen opens to the living areas, while built-in bookcases and a gas fireplace add character and function to the family room. Step outside to one of two waterside decks and enjoy the ever-changing river views, passing boats and beautiful scenery. Upstairs, wake up each morning to endless WATER VIEWS from the Primary Suite, then step directly onto your private waterside deck with your morning coffee. Bedrooms feature the privacy and convenience of ensuite baths. A large upper-level Bonus Room with its own full bath provides wonderful flexibility—create a 3rd bedroom, spacious home office, a guest suite, den or whatever best fits your lifestyle. The views are even better from up here! Freshly painted and truly MOVE-IN READY, this light-filled end unit offers the combination everyone is looking for—beautiful interiors, flexible living space, two waterside decks and an exceptional location overlooking the Chester River. Bayside offers wonderful community amenities, including a swimming pool, party room, fitness center, tennis/pickleball courts and volleyball. The 38+ mile Cross Island Trail is just around the corner for walking, jogging and biking. You’re also conveniently located near restaurants, grocery shopping, outlet shopping and golf courses. Love boating? The marina bordering the community offers boat slips that may be available for rent or purchase, making it easy to enjoy everything the Chesapeake Bay and Eastern Shore have to offer. Come experience the Kent Island waterfront lifestyle—beautiful views, boating, recreation and convenience, all right outside your door!

1010 Auckland Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: 8003833535
$750,000
3 Beds ⋅ 3 Baths
Welcome to 36375 Sea Grass Way, a beautifully appointed end-unit townhome in the highly desirable bayfront amenity rich Jack Nicklaus golf course community- Bayside. With 3 bedrooms, 2.5 baths, a first-floor primary suite, attached garage, and tranquil pond views, this coastal retreat offers the ideal combination of comfort, space, and low-maintenance living. Step inside to a light-filled, open-concept floor plan featuring hardwood flooring, crown molding, recessed lighting, and an easy flow between the kitchen, dining, and living areas. The gourmet kitchen is designed for both everyday living and entertaining with quartz countertops, a generous center island, breakfast bar, pantry, stainless steel appliances, cooktop, and wall oven. The spacious main-level primary suite offers a walk-in closet and private bath, allowing for convenient one-level living. A sitting area, powder room, and main-floor laundry complete the first level. Just beyond the living space, the screened porch and hardscape patio provides a peaceful place to relax, dine outdoors, and enjoy the surrounding pond and water views. Upstairs, guests will appreciate two generously sized bedrooms with walk-in closets, a full bath, and a spacious family room that provides flexible additional living space. A storage room adds even more functionality to the home. The property is being offered partially furnished, making the transition to coastal living easier. Located within Bayside, residents enjoy access to an exceptional collection of amenities including indoor and outdoor pools, fitness facilities, tennis and pickleball courts, playground, dog park, walking and jogging paths, clubhouse facilities, community dock and pier, beach access, restaurants, The Freeman Arts Pavilion, and golf with membership opportunities available. Whether you are searching for a primary residence or coastal getaway, 36375 Sea Grass Way offers an opportunity to enjoy the sought-after Bayside lifestyle just minutes from the beaches, dining, shopping, and attractions of the Delaware and Maryland coast.

36375 Sea Grass Way, Selbyville

Listing courtesy of Northrop Realty. Contact: (302) 539-2900
$485,000
4 Beds ⋅ 4 Baths
LIKE-NEW LUXURY with 4 BEDROOMS plus 2-CAR GARAGE and RESORT-STYLE AMENITIES nested in The Landings at Bayside! Built in 2024 and still under the builder’s warranty, this stunning end-unit townhouse offers over 2,700 sq. ft. of beautifully finished living space with privacy and functionality on every level. The owners expanded the original floor plan by adding valuable space off the kitchen and primary bedroom plus a ground-floor bonus room and large storage space. Upgraded with beautiful wide Luxury Vinyl Plank Flooring, Recessed Lighting and Craftsman Architectural Doors plus Custom Window Treatments throughout. Enjoy the Open Coastal Living Space centered around the Beautifully Upgraded Kitchen with quartz countertops, stainless steel appliances, subway tile backsplash, pendant lighting, and an oversized kitchen island, perfect for everyday living and entertaining. The third level provides a spacious primary suite filled with natural light featuring a walk-in closet and luxurious en-suite bath with dual vanity, tiled walk-in shower, and separate soaking tub. A split-bedroom floor plan provides privacy for your 2 extra guest bedrooms. The fourth level offers exceptional flexibility with a fourth bedroom and bonus living space, full bath, and a huge private balcony—perfect for relaxing and enjoying the peaceful surroundings. Enjoy this fabulous home in The Landings at Bayside, ideally located just minutes from Assateague Island and the booming West OC Area, with access to Premiere Dining, Shopping and Resort Living. The Bayside Community offers Exceptional Amenities: indoor and outdoor pools, play areas, fitness center, tennis courts, kayak launch/pier, and crabbing pier, and club house plus lawn care and landscaping included for easy, low-maintenance coastal living.

8663 Bat Creek Loop Ln Unit #3, Berlin

Listing courtesy of Mary McCracken Realty, Inc. Contact: 4107231895
$839,900
4 Beds ⋅ 3 Baths
Welcome to Bayside! Tucked away on the secluded street of Coneflower, this 3-bedroom, 3-bath home offers a flexible floor plan designed for easy coastal living. The open-concept main level features a spacious living area with fireplace, a first-floor owner’s suite, and a separate study that can easily serve as a home office, den, or optional fourth bedroom. Upstairs, you’ll find additional bedrooms and a versatile loft, perfect for guests or a second living space. A screened porch provides the ideal spot to relax and enjoy the coastal lifestyle, while on-street parking adds extra convenience. Enjoy all that Bayside has to offer, multiple outdoor pools including indoor pool, the award-winning Freeman Arts Pavilion, clubhouse with restaurant, Jack Nicklaus Signature Golf Course, state-of-the-art fitness facilities, walking and biking trails, and so much more—all just minutes from the beaches of Fenwick Island and Ocean City.

36496 Coneflower Cir, Selbyville

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$2,200,000
7 Beds ⋅ 5 Baths
OPEN HOUSES Thursday, Friday & Saturday. Elevated Coastal Luxury in Bayside Fenwick. Presenting 30515 N Magnolia Crossing, an exceptional fully furnished coastal residence in the premier resort community of Bayside Fenwick. Beautifully maintained and thoughtfully refreshed for sale, this home offers an exceptional combination of style, condition, and investment potential. Recent updates include fresh interior and exterior paint, new hardwood stairs, and luxury vinyl plank flooring throughout the first level and second-level bedrooms, replacing the previous carpeting and creating a fresh, cohesive look throughout. The property also boasts a strong history as a successful rental investment, generating approximately $100,000 in annual rental income. Whether envisioned as a primary residence, coastal retreat, second home, or income-producing investment, this property offers tremendous versatility. Meticulously cared for over the years and presented in truly turn-key condition, it is ready to be enjoyed from day one. Perched on Magnolia Crossing in a spectacular setting overlooking the 14th hole of Bayside’s prestigious Jack Nicklaus Signature Golf Course, this impressive residence captures picturesque golf course vistas complemented by beautiful water views toward the Assawoman Bay. Recently transformed with a complete exterior repaint, the home makes a striking first impression, unveiling a fresh new identity befitting its extraordinary surroundings. Built by Schell Brothers, the sought-after Avalon floor plan unfolds across three expansive levels, offering nearly 5,500 square feet of sophisticated coastal living with 7 bedrooms, 4.5 baths, and a private elevator connecting every level. Designed for gathering on a grand scale, the main living level brings together a spacious gourmet kitchen, dining room, impressive great room, and guest accommodations, while the upper level is home to the private primary suite and additional bedrooms. The lower level extends the possibilities with a generous recreation room, additional guest quarters, custom mudroom storage, and an oversized garage ready to accommodate everything from golf clubs and bicycles to beach gear. And then there is Bayside itself, a destination unlike any other. Championship golf, indoor and outdoor pools, fitness centers, tennis and pickleball, walking and biking trails, kayaking and fishing, waterfront dining, the Freeman Arts Pavilion, beach shuttle service, and an extraordinary collection of resort-style amenities create a lifestyle where every day can feel like a vacation. This is only the beginning. When 30515 N Magnolia Crossing officially debuts, discover a residence where refined coastal style, luxurious finishes, exceptional spaces, and an enviable golf-and-bay setting come together in one remarkable Bayside address. Some images on the tour have been virtually staged or enhanced.

30515 N Magnolia Xing, Selbyville

Listing courtesy of Northrop Realty. Contact: (302) 539-2900
$1,825,000
5 Beds ⋅ 5 Baths
Welcome to 27017 Bay Bluff Rd - one of the most exceptional Kingfisher homes in the award-winning Bayside community. Built by Schell Brothers and perfectly positioned on a premium corner lot, this beautifully appointed 5-bedroom, 5 full bath residence has been extensively upgraded and thoughtfully customized to create a truly one-of-a-kind coastal retreat. The main level showcases wide plank hardwood flooring, custom wainscoting, designer lighting, and sophisticated finishes throughout. At the heart of the home is the gourmet kitchen, enhanced with Schell Brothers’ coveted Professional Kitchen Package. Additional Highlights include upgraded appliances, a large freestanding center island, statement range hood, elegant cabinetry with upgraded hardware, and a striking marble backsplash. The kitchen flows effortlessly into the family room and dining area, creating an inviting setting for both everyday living and entertaining. Also on the main level is the luxurious primary suite with a beautifully appointed en suite bath, along with an additional bedroom and full bath—ideal for guests or multigenerational living. Upstairs, a spacious loft offers flexible living space and is complemented by three additional bedrooms and three full bathrooms. All five bathrooms have been elevated with imported Italian marble and high-end finishes, including select Restoration Hardware lighting, vanity, and cabinetry. Outdoor living is equally impressive. Relax or entertain on the enhanced covered porch and expansive travertine paver patio while enjoying the peaceful surroundings. High end luxury custom window shades and plantation shutters from Design Window and a two-car garage complete this remarkable home. Just two blocks from a members only pool, The Point, and the 38° bay front bar and restaurant, this sought-after location places the best of Bayside within easy reach. Residents enjoy award-winning amenities including the Jack Nicklaus Signature Golf Course, resort-style pools, fitness center, tennis, pickleball and basketball courts, nature trails, kayaking, a beach shuttle, and seasonal concerts and performances at the Freeman Arts Concert Pavilion. With its premium setting, beautiful views, exceptional upgrades, and unbeatable location, this is more than a home—it is the Bayside lifestyle at its finest. Schedule your tour today!

27017 Bay Bluff Rd, Selbyville

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$1,195,000
4 Beds ⋅ 4 Baths
Located in the private quite Harbor Crest neighborhood of the Bayside Resort & Golf community. This natural light filled 4BR/3.5BA Beazer built Fenwick model townhouse is a must see! Over 3,600 square feet of 4-level living space, tons of parking, recessed lights throughout, hardwood floors, decks and a screened porch with amazing views. A large open floor plan with sitting areas for entertainment, massive eat-in island kitchen with SS Whirlpool appliances, crown molding, with views in every direction of Jack Nicklaus Bayside golf course, the Ocean City skyline and Assawoman Bay. The Bayside community has a premium amenity package! Here are just some: 6 outdoor pools, an indoor pool, sauna, jacuzzis, a state-of-the-art fitness center, tennis & pickleball courts, on-site security, a dog park, bocce ball, fishing, kayak and stand-up paddleboard launches, two community bar and grilles, and the world-class Jack Nicklaus Signature Golf Course. Bayside also features the new Freeman Arts Pavilion, which hosts local, regional & national, chart-topping musical acts & live performances right in your backyard.

22051 Crestview Dr, Selbyville

Listing courtesy of RE/MAX Town Center. Contact: 3015402232
$935,000
5 Beds ⋅ 4 Baths
Surrounded by mature woods and overlooking a tranquil pond with a fountain, space, and sophisticated coastal living. Featuring five bedrooms, three full baths & a half bath, the thoughtfully designed floor plan includes two private bedroom suites, with one conveniently located on each level. From the moment you arrive, the home makes a statement with its expansive front porch, while multiple covered outdoor living spaces invite you to enjoy the beautiful setting. Relax on the paver patio overlooking the woods and fountain-fed pond, unwind in the screened-in rear porch, or enjoy the additional screened-in side porch that opens to another patio. With several inviting outdoor spaces, there is no shortage of places to entertain, dine, or simply take in the peaceful surroundings. Inside, the heart of the home is truly the kitchen, where soaring two-story ceilings create a dramatic sense of scale. Two stories of windows fill the space with natural light, while an open lofted hallway above adds architectural interest and connects the two levels. The spacious kitchen features an oversized island, granite countertops, stainless steel appliances complete with a Viking range hood & plenty of room for casual dining. For more formal occasions, a separate dining room provides an elegant setting for entertaining. Just off the kitchen, a dedicated wine cellar and abundant storage add both character and functionality, while the screened-in porch makes it easy to take meals and gatherings outdoors. The main level also features a welcoming living room with a gas fireplace and gorgeous built-ins, along with an additional family or sitting room offering flexible space for a playroom, home office, media room, or additional gathering space. A large laundry room and half bath add everyday convenience. The main-level primary suite is a private retreat, featuring a generous walk-in closet and a spacious bath with double vanities, a soaking tub, and a walk-in shower. Direct access from the suite to the screened-in rear porch and patio creates an effortless connection to the outdoors. Upstairs, the open lofted hallway welcomes you with beautiful views down into the dramatic two-story kitchen and living spaces below. Three additional bedrooms, an office, and a full bath complete the second level, including a spacious bedroom suite with its own private full bath. The current owners purchased the home as a five-bedroom property, with the room currently used as an office previously being utilized as a bedroom. A front balcony provides yet another place to step outside and enjoy the surroundings. And then there is Bayside itself, offering a wealth of amenities and recreation opportunities for those who choose to take advantage of them. Residents can enjoy indoor and outdoor pools, a fitness center, splash pad, beach access, basketball courts, pickleball courts, tennis and volleyball courts, a kayak launch, golf course, beach shuttle, fishing pier, on-site dining, and so much more. As an original Freeman-built home, the property is not required to pay community recreation fees unless the owners choose to use the recreation amenities, offering a unique opportunity to enjoy the home and Bayside lifestyle with added flexibility. With its distinctive two-story architecture, two bedroom suites, multiple covered outdoor living spaces, private wooded and pond views, generous floor plan, and access to an incredible array of Bayside amenities, 11250 Signature Boulevard is a truly special opportunity to experience coastal Delaware living at its best.

11250 Signature Blvd, Selbyville

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact: (410) 524-0919
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