Bayside Real Estate

Bayside Real Estate

Welcome to Bayside, a picturesque subdivision nestled in the heart of the United States, where serene living meets vibrant community spirit. This charming neighborhood is the perfect blend of modern amenities and natural beauty, making it an ideal place for families, professionals, and retirees alike.

Bayside boasts a variety of beautifully designed homes, each showcasing unique architectural styles that cater to diverse tastes. Whether you’re seeking a cozy cottage or a spacious family residence, you’ll find an array of options that fit your lifestyle and budget. The tree-lined streets are adorned with lush landscaping, creating a warm and inviting atmosphere that encourages evening strolls and friendly conversations with neighbors.

One of the standout features of Bayside is its commitment to community engagement. Residents enjoy access to numerous parks, walking trails, and recreational facilities, perfect for outdoor enthusiasts and families looking to create lasting memories. The local community center hosts a variety of events throughout the year, fostering connections and a sense of belonging among residents.

Convenience is key in Bayside, with shopping centers, restaurants, and essential services just a short drive away. Families will appreciate the proximity to highly-rated schools, ensuring quality education for children of all ages.

With its idyllic setting, strong community ties, and convenient location, Bayside offers a lifestyle that celebrates both relaxation and connection. Come discover the charm of Bayside and envision your future in this delightful subdivision!

Newest Listings in Bayside

107 Widgeon Way, Chester
$349,900
3 Beds ⋅ 3 Baths
ASSUME A 2.875% FHA LOAN * $1777 MO PYMT *BAYSIDE IN CHESTER/KENT ISLAND * GARAGE TOWNHOME * PRICED TO SELL EXCELLENT OPPORTUNITY TO ASSUME AN FHA 2.875% FIXED INTEREST RATE * Qualified Owner Occupant Buyers: Take Advantage of this rare opportunity to assume this FHA Loan with approximately 25 years remaining * TOTAL PITI PAYMENT OF $1777.56 PER MONTH* You'll Be Way Ahead of the Interest Rate Game AND Own a Spacious 3 Level Garage Townhome in the Popular Community of Bayside with 3 Bedrooms, 2.5 Baths, Deck off Living Room & Propane Gas Fireplace. The Primary Bedroom has a walk-in closet, vaulted ceilings and an ensuite full bath with shower stall and skylight. The Main Level has a spacious open layout with bright and sunny front Kitchen featuring upgraded counters, stainless steel appliances, ample cabinet space and pass through to bar seating on the Dining Room side. The Living Room faces towards the back with Sliders to a Deck great for grilling. Bayside Offers Great Community Amenities to include outdoor pool, exercise room, tennis and volleyball, on-site management AND walking distance to Castle Harbor Marina.

107 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

12455 Coastal Marsh Dr Unit 904, Berlin
$450,000
3 Beds ⋅ 4 Baths
Welcome to 12544 Coastal Marsh Drive, Unit 904, located in the desirable Bayside community of Berlin, Maryland! This beautifully appointed 3-bedroom, 2-full-bath, 2-half-bath townhome offers the perfect blend of coastal charm, modern finishes, and comfortable living. Thoughtfully designed and tastefully decorated throughout, this home features a bright, inviting interior with stylish coastal accents and plenty of space for entertaining family and friends. The spacious primary suite offers a relaxing retreat with a beautiful four-poster bed, tray ceiling, and private en-suite bathroom featuring a double vanity and tiled shower. Two additional bedrooms provide comfortable accommodations, including a charming bunk room with custom coastal-inspired wallpaper, ideal for guests or additional sleeping space. Enjoy thoughtful details throughout, including attractive trim work, an eye-catching blue accent wall in the dining area, modern fixtures, and a convenient laundry area with a full-size washer and dryer. Step outside onto the private balcony, perfect for enjoying your morning coffee or unwinding after a day at the beach. Located in Worcester County, this property offers convenient access to Ocean City’s beautiful beaches, the charm of downtown Berlin, nearby restaurants, shopping, and entertainment. Whether you're searching for a primary residence, coastal getaway, or investment opportunity, this beautifully maintained home is ready to enjoy. Experience the best of Eastern Shore living at 12544 Coastal Marsh Drive!

12455 Coastal Marsh Dr Unit 904, Berlin

Listing courtesy of Coastal Life Realty Group LLC. Contact:

36465 Wild Rose Cir, Selbyville
$770,000
5 Beds ⋅ 4 Baths

36465 Wild Rose Cir, Selbyville

Listing courtesy of Keller Williams Realty. Contact:

31568 Winterberry Pkwy Unit 109, Selbyville
$385,000
4 Beds ⋅ 3 Baths
Turn-Key Coastal Living in Bayside | Fully Furnished 4 BR / 3 BA Condo. HVAC replaced in 2023. Welcome to resort-style coastal living at 31568 Winterberry Parkway, Unit 109, located in the award-winning community of Bayside. This pristine, fully furnished 4-bedroom, 3-bathroom condo offers an effortless turn-key experience—ideal as a low-maintenance primary residence, a personal beach retreat, or a turn-key rental investment. 2 entrances allow flexible use. Airy, open-concept living and dining layout crafted for relaxed living and seamless entertaining. The main living area flows out to a private, spacious screened-in porch—an idyllic setting for morning coffee or relaxing evening breezes. The thoughtful floor plan features a separate suite (with its own entrance/exit) with generous sleeping capacity, built-ins and full bath, ensuring total comfort and privacy for family and guests. Unmatched lifestyle convenience awaits right outside your door. Bayside is renowned for its world-class, resort-style amenities, including: Jack Nicklaus Signature Golf Course with clubhouse and pro shop, multiple outdoor pools, indoor heated pool, hot tub, and splash park, Health & Aquatic Club with state-of-the-art fitness center, saunas, and group fitness, Racquet Sports Complex featuring tennis and pickleball courts, The Point at Bayside: Waterfront sanctuary with kayak/paddleboard launch, fishing pier, and views of the Ocean City skyline. On-Site Dining (38 Degrees at Bayside, Cove Bar & Grille) and the Freeman Arts Pavilion hosting live outdoor concerts with outstanding entertainers. Seasonal Beach Shuttle offering convenient direct transport to Fenwick Island beaches. Located just minutes from the Fenwick Island and Ocean City shorelines, this home is completely move-in ready. Schedule your tour today and start enjoying coastal Delaware living! $10,000 for buyer to use toward closing costs with acceptable offer. This address is a NON-mandatory home for Bayside Membership. Ask your agent for more info!

31568 Winterberry Pkwy Unit 109, Selbyville

Listing courtesy of Active Adults Realty. Contact:

31568 Winterberry Pkwy Unit 110, Selbyville
$389,900
4 Beds ⋅ 3 Baths
Spacious and undeniably beautiful condo overlooking the 17th green in the premier amenity rich community of Bayside. This home offers 4bd / 3ba with a SEPARATE "LOCK-OUT" SUITE that includes a king sized bedroom, private bath with walk-in shower, walk-in closet and PRIVATE ACCESS from the hallway or the unit. Spacious open floor plan, solid surface countertops, upgraded cabinetry, hardwood floors, gas fireplace, tile, recessed lighting, glass pendant lights, surround sound, upgraded trim, tile bathrooms, and an awesome screen porch boasting a wall mounted TV and tiled floors for your outdoor enjoyment. Newer HVAC. Enjoy all Bayside has to offer- Nature Trails, stocked ponds, schedule of programs,, events & live music at the award wining Freeman Stage. Indoor and outdoor pools, fitness centers, classes, tennis courts, basketball, volleyball, snack/tiki bars and so much more!

31568 Winterberry Pkwy Unit 110, Selbyville

Listing courtesy of Coldwell Banker Realty. Contact:

36486 Wild Rose Cir, Selbyville
$845,000
5 Beds ⋅ 4 Baths
Welcome to 36486 Wild Rose Circle, a spacious 5-bedroom, 4-bath home in the highly sought-after, amenity-rich community of Bayside. With a flexible floor plan, expansive first-floor living, multiple gathering spaces and a successful vacation rental history, this home is ready to be enjoyed as a year-round residence, coastal retreat or investment property. The inviting covered front porch sets the tone before stepping inside, where warm hardwood floors, crown molding and an open, flowing floor plan create a welcoming space designed for entertaining family and friends. The kitchen truly is the heart of the home, featuring an abundance of beautiful wood cabinetry, stainless steel appliances, a large center island with breakfast bar and plenty of counter space. From here, the home flows naturally into the dining and living areas, where a gas fireplace anchors the main gathering space. Need a little more room? An additional sunroom/game room expands the living space even further and offers the perfect spot for game nights, morning coffee or simply relaxing after a day at the beach. From here, step outside to the paver patio and outdoor shower, perfect for rinsing off after a day on the sand or bay. One of the home's biggest advantages is its first-floor layout. The main level offers four bedrooms and three full baths, including three guest bedrooms and a private primary suite tucked away from the main living areas. The spacious primary bedroom features hardwood flooring, a tray ceiling and two walk-in closets. The en-suite bath offers dual vanities, a large soaking tub, tiled walk-in shower with glass enclosure and private water closet. Upstairs, the fifth bedroom features its own private full bath, creating a fantastic guest suite with the flexibility to also serve as a bunk room, home office, media room or additional recreation space. And don't overlook the oversized garage! Currently set up as the ultimate game room with ping pong, foosball and air hockey, it has become an extension of the home's entertaining space while still offering the versatility and storage today's coastal buyer needs. Of course, owning in Bayside is about more than the house — it's about the lifestyle. Residents enjoy an incredible collection of resort-style amenities including multiple outdoor pools, an indoor pool, fitness facilities, recreational amenities, award winning golf course and more. The newly redesigned Freeman Arts Pavilion brings live music and entertainment right to the community, making summer evenings even more memorable. Whether you're looking for a place to call home, your own coastal getaway or an investment opportunity with an established rental history, 36486 Wild Rose Circle offers the space, versatility and Bayside lifestyle you've been searching for.

36486 Wild Rose Cir, Selbyville

Listing courtesy of Coldwell Banker Realty. Contact:

208 Widgeon Way, Chester
$590,000
3 Beds ⋅ 4 Baths
* OPEN HOUSE, SATURDAY OCT 24th FROM 12-3PM * Direct Marina Views of Castle Harbor Marina * Watch the Boats and Sunsets from your Deck & Balcony * One-of-a-Kind View * END-UNIT with Garage * Nestled in the prestigious Bayside community, this exquisite end-of-row townhouse offers a harmonious blend of contemporary coastal design and luxurious living. With three spacious bedrooms and three and a half elegantly appointed bathrooms, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The heart of the home features upgraded countertops, a generous kitchen island, and an eat-in space, perfect for casual gatherings. The family room, adorned with a cozy gas fireplace framed by glass doors, creates an intimate atmosphere for relaxation. Recessed lighting and ceiling fans enhance the ambiance, while large windows drench the space in natural light, showcasing the beautiful luxury vinyl plank and ceramic tile flooring. Retreat to the primary suite, where a walk-in closet and a spa-like bathroom with a walk-in shower await, offering a private oasis for unwinding after a long day. Additional bedrooms are equally spacious, ensuring comfort for all. The exterior of the property is equally impressive, featuring a wrap-around porch and a balcony that invite you to enjoy the serene surroundings. The community amenities are unparalleled, including a sparkling outdoor pool, tennis and volleyball courts, and a clubhouse that serves as a hub for social gatherings. With meticulously maintained common areas and professional management, the association fee covers everything from lawn care to snow removal, allowing you to enjoy a carefree lifestyle. Situated on a corner lot, this home offers easy access to the Chester River, perfect for those who appreciate water-oriented living. The nearby recreational facilities and common grounds provide ample opportunities for outdoor activities and relaxation. With an attached garage and secure parking, convenience is at your fingertips. Located just minutes from the airport and local attractions, this property embodies the essence of luxury living in a vibrant community. Experience the perfect blend of comfort, style, and convenience in this stunning Bayside townhouse, where every detail has been thoughtfully curated for an exclusive lifestyle.

208 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

36548 Wild Rose Cir, Selbyville
$650,000
4 Beds ⋅ 3 Baths
Welcome to 36548 Wild Rose Circle! Located in the vibrant Bayside community, this beautifully appointed coastal twin home blends timeless charm with modern comfort. Offering 2,863 square feet of thoughtfully designed living space, the residence features four spacious bedrooms, two and a half baths, and inviting spaces for both everyday living and entertaining. Inside, warm hardwood floors greet you beneath a dramatic vaulted ceiling, while dormer and transom windows bathe the living room in natural light. A shiplap accent wall adds coastal character, and the open layout flows seamlessly into the dining room, where wainscoting and a beautiful coastal chandelier create an elegant setting for gatherings. Throughout the home, tray ceilings, crown molding, chair rail accents, wainscoting, recessed lighting, and plantation shutters enhance the refined interior. The gourmet kitchen offers upgraded countertops, a stainless-steel refrigerator, and a generous island with ample room for preparation and gathering. A tray ceiling, recessed lighting, and pendant fixtures add architectural interest and warmth. The adjoining casual dining area opens naturally to the den, creating a comfortable space to relax and entertain, with convenient access to the screened porch. The first floor primary suite provides a peaceful retreat, complete with a tray ceiling, walk-in closet, and spacious private bath featuring a dual vanity and shower stall. Upstairs, a versatile loft, additional bedrooms, and a full bath offer comfortable accommodations for family and guests, along with flexibility for a home office or sitting area. A conveniently located half bath and laundry room with access to the attached garage complete the first level. Outside, extensive hardscaping and mature landscaping frame the lush lawn, creating an appealing backdrop for outdoor living. Enjoy morning coffee on the screened porch, alfresco dining on the patio, or cocktails with friends at the outdoor bar. An attached garage and additional driveway parking provide everyday convenience. Bayside’s exceptional amenities complement the home’s relaxed coastal appeal, with indoor and outdoor pools, fitness facilities, tennis and pickleball courts, a playground, dog park, walking and jogging paths, and clubhouse facilities. A community dock and pier, beach access, restaurants, and golf membership opportunities further enhance the lifestyle, while seasonal outdoor performances at the Freeman Arts Pavilion bring entertainment close to home. With spacious interiors, charming architectural details, and welcoming outdoor spaces, this lovely residence 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. Some photos have been virtually staged for presentation purposes.

36548 Wild Rose Cir, Selbyville

Listing courtesy of Northrop Realty. Contact:

36380 Azalea Ave, Selbyville
$575,000
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:

510 Auckland Way, Chester
$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:

512 Auckland Way, Chester
$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. Newer roof, HVAC and hot water heater. 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:

1012 Auckland Way, Chester
$599,900
3 Beds ⋅ 4 Baths
KENT ISLAND WATERFRONT • GOURMET KITCHEN • TWO PRIVATE DECKS • LUXURIOUS PRIMARY SUITE • CLUBHOUSE + FITNESS CENTER • MARINA ACCESS 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:

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