Bayside Homes under $500,000

Bayside Homes under $500,000

Welcome to Bayside, a hidden gem nestled in the heart of the United States, where charm meets affordability! This vibrant subdivision offers a unique blend of serene living and modern conveniences, making it an ideal choice for families, young professionals, and retirees alike. With its picturesque tree-lined streets and friendly atmosphere, Bayside is not just a place to live; it’s a community to thrive in.

One of the most appealing aspects of Bayside is its diverse selection of homes, particularly those priced under $500,000. Here, you can find a variety of architectural styles, from cozy single-family homes to contemporary townhouses, all designed to cater to different tastes and lifestyles. The affordability of these homes makes it possible for first-time buyers to step into the housing market without breaking the bank, while also providing ample opportunities for investors seeking rental properties.

Living in Bayside means having access to a wealth of amenities. Residents enjoy proximity to lush parks, top-rated schools, and a variety of shopping and dining options. Whether you’re strolling through the local farmers' market or enjoying a sunny afternoon at the nearby lake, there’s always something happening in this lively neighborhood.

In Bayside, you’ll find not just a house, but a place to call home. With its welcoming spirit, affordable housing, and vibrant community life, Bayside is the perfect place to create lasting memories. Come explore what this wonderful subdivision has to offer, and discover your dream home today!

Newest Bayside Homes under $500,000

31568 Winterberry Pkwy Unit 109, Selbyville
$385,000
4 Beds ⋅ 3 Baths ⋅ DESU2122046 MLS ⋅ None Available BLDG.
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.

31568 Winterberry Pkwy Unit 109, Selbyville
31568 Winterberry Pkwy Unit 110, Selbyville
$389,900
4 Beds ⋅ 3 Baths ⋅ DESU2122040 MLS ⋅ None Available BLDG.
Spacious and undeniably beautiful condo overlooking the 17th green in the premier amenity rich community of Bayside. This home offers 4bd / 3ba with separate lock-out that includes a king sized bedroom, private bath with walk-in shower and walk-in closet. Spacious open floorplan, 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 for your outdoor enjoyment. 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
510 Auckland Way, Chester
$410,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018734 MLS
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
512 Auckland Way, Chester
$375,000
3 Beds ⋅ 4 Baths ⋅ MDQA2018750 MLS ⋅ Bayside BLDG.
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
8663 Bat Creek Loop Ln Unit 3, Berlin
$485,000
4 Beds ⋅ 4 Baths ⋅ MDWO2041078 MLS ⋅ None Available BLDG.
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
108 Blenny Ln, Chester
$369,900
3 Beds ⋅ 3 Baths ⋅ MDQA2018242 MLS
Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

108 Blenny Ln, Chester
11145 Signature Blvd, Selbyville
$469,000
3 Beds ⋅ 3 Baths ⋅ DESU2117622 MLS ⋅ None Available BLDG.
Coastal living at its best in Bayside—one of Delaware’s premier resort-style communities. This beautifully designed home offers the perfect blend of comfort and flexibility. Gather in one of three living spaces on the first floor, including the spacious family room with a cozy gas fireplace, a private office with built-in bookcases, and a welcoming sitting area. The dining area and updated kitchen are conveniently located just off the family room, creating an ideal flow for everyday living and entertaining. Step outside to a screened porch and private fenced courtyard—your own peaceful retreat after a day at the beach. Upstairs, the oversized owner’s suite feels like a true escape, featuring a private balcony, spa-like bath with soaking tub, tiled shower, and a generous walk-in closet. Two additional bedrooms provide comfortable space for guests or family. Enjoy peace of mind with a new tankless water heater and new second-floor HVAC. The rear-entry two-car garage offers ample storage for all your beach gear, while the HOA handles exterior maintenance, lawn care, and irrigation for easy, low-stress living. With a Sports Membership, experience Bayside’s unmatched resort amenities—pools, fitness center, tennis, pickleball, dog parks, nature trails, kayak launch, and the Jack Nicklaus Signature Golf Course. Dine waterfront, catch live shows at Freeman Arts Pavilion, and enjoy it all just steps from your home. This isn’t just a home—it’s the coastal lifestyle you’ve been dreaming of.

11145 Signature Blvd, Selbyville
31568 Winterberry Pkwy Unit 309, Selbyville
$389,000
4 Beds ⋅ 3 Baths ⋅ DESU2115764 MLS ⋅ None Available BLDG.
Experience resort-style coastal living in one of the area's most sought-after communities. This beautifully maintained condo offers exceptional value in Bayside, combining spacious living, modern updates, and world-class amenities—all with the convenience of low-maintenance ownership. Designed with flexibility in mind, the home features two generously sized primary suites, each with its own private ensuite bathroom, along with an optional one-bedroom, one-bath lockout suite that's perfect for guests, multi-generational living, or generating rental income. The open-concept floor plan seamlessly connects the kitchen, dining area, and family room, creating an inviting space for entertaining or relaxing. The updated kitchen is equipped with brand-new GE Profile appliances, while the family room is anchored by a cozy fireplace that adds warmth and charm. Step outside to the private screened porch overlooking beautifully landscaped grounds, the perfect place to enjoy your morning coffee or unwind after a day at the beach. Major updates provide added peace of mind, including a new roof in 2024, as well as a new HVAC system, furnace, and hot water heater installed within the last year. Assigned parking and additional storage complete the package. Life in Bayside means every day feels like a vacation. Residents enjoy access to the award-winning Jack Nicklaus Signature Golf Course, a state-of-the-art Health & Aquatic Center with a heated indoor lap pool, fitness center, hot tub, sauna, and group fitness classes. Additional amenities include four outdoor pools, a children's splash zone, waterfall hot tub, tennis and pickleball courts, bocce, putting green, golf academy, scenic walking and biking trails, fishing ponds, kayak launch, beach shuttle, and a full calendar of social events and enrichment classes through the Bayside Institute. When it's time to dine or unwind, head to The Point for waterfront dining at the popular 38 Degrees restaurant overlooking Assawoman Bay and the Ocean City skyline, or enjoy nationally recognized concerts and performances at the nearby Freeman Arts Pavilion. Best of all, exterior maintenance, landscaping, and many major upkeep responsibilities are handled for you, allowing you to spend more time enjoying everything this incredible coastal community has to offer.

31568 Winterberry Pkwy Unit 309, Selbyville
8663 Bat Creek Loop Ln Unit 1, Berlin
$449,900
4 Beds ⋅ 4 Baths ⋅ MDWO2038996 MLS ⋅ None Available BLDG.
PRICED TO SELL $162.00 PER SQFT!!! Welcome to your new coastal retreat in West Ocean City! LIKE NEW / STILL under builders warranty!!!!!This beautiful four-bedroom, three-and-a-half-bath townhouse with an additional den /Office offers spacious living and modern comfort in one of the area’s most desirable locations. Great End Unit Location. The home features two-car garage, perfect for year-round convenience, storage, or hobby space. Designed for both relaxation and entertaining, this community offers exceptional amenities including an exercise facility, indoor pool, outdoor pool, kayak pier, and crabbing pier — ideal for enjoying the coastal lifestyle to the fullest. Perfectly situated just minutes from Ocean City’s beaches, dining, shopping, and entertainment, and a short drive to the natural beauty of Assateague Island, this property combines convenience, recreation, and seaside charm. Whether you’re looking for a primary residence, vacation home, or investment opportunity, this townhouse delivers the best of Eastern Shore living! Spacious and quiet interior end-unit with minimal car traffic, offering a peaceful and private setting in the community. 4 story unit with western facing deck with beautiful sunsets

8663 Bat Creek Loop Ln Unit 1, Berlin
807 Auckland Way, Chester
$425,500
3 Beds ⋅ 4 Baths ⋅ MDQA2017442 MLS
Seller is offering up to $9,000 toward the buyer's interest rate buydown or closing costs. That's real money applied at settlement, and on a home already carrying over $50,000 in owner improvements, it's the kind of combination that doesn't sit long. This is a renovated end-unit townhome with three bedrooms and three and a half baths in Bayside, an established waterfront community along the Chester River. Hardwood runs the main and upper levels — no carpet — beginning at a slate tile entry that opens into rooms filled with natural light. The renovated kitchen is the centerpiece: Thermador induction cooktop, GE Monogram wall oven, Bosch dishwasher, granite counters, updated cabinetry, and recessed lighting, all opening directly to the living area so the space works as one. That living area centers on a gas fireplace framed by built-in bookshelves. Just off it, a private deck with a retractable awning looks out to seasonal water views of the Chester River. Upstairs, the primary suite includes a walk-in closet, an ensuite bath with jetted soaking tub and separate shower, and a private deck of its own. The second upper-level bedroom has its own attached full bath. Above that, the top-floor space adds two walk-in closets and a third full bath, with the flexibility to serve as a guest room, home office, or studio. Recently updated HVAC. High-efficiency washer and dryer convey. Attached one-car garage for protected parking and storage. End-unit positioning means no neighbor on one side. The monthly fee covers lawn maintenance, snow removal, pool access, and recreation facilities — the maintenance is handled, the amenities are there, and the weekends are yours. Route 50/301 is minutes away, with shopping and dining close by. Nothing here needs doing. Ask about the $9,000 buyer credit and current availability.

807 Auckland Way, Chester
106 Bodys Neck Rd, Chester
$429,900
3 Beds ⋅ 3 Baths ⋅ MDQA2017432 MLS
Marina views, waterfront surroundings, and the Bayside lifestyle—all at a new price of $429,900! Welcome to 106 Bodys Neck Road in Chester, where everyday living comes with a view. This 3-bedroom, 2.5-bath home offers upper and lower decks overlooking the marina, creating inviting spaces to enjoy your morning coffee, unwind at the end of the day, or simply watch the activity along the water. Inside, you'll find a comfortable and functional layout featuring a gas fireplace, spacious living areas, and an attached 1-car garage. New carpet in the lower level adds a fresh touch, while a new roof installed in 2023 offers an important recent update. The front foot fee was paid in full in 2024, and the seller is also providing a one-year home warranty for added peace of mind. Bayside offers a resort-style setting with amenities that include a clubhouse, outdoor pool, fitness center, tennis and volleyball courts, and scenic walking and jogging trails. Marina and water access add to the Chesapeake Bay lifestyle that makes this community so appealing. Conveniently located on Kent Island with easy access to Route 50, the Bay Bridge, dining, shopping, and nearby waterfront destinations. Now offered at $429,900. Come experience the marina view and see what life at Bayside could look like for you.

106 Bodys Neck Rd, Chester
12461 Coastal Marsh Dr Unit 101, Berlin
$474,900
4 Beds ⋅ 5 Baths ⋅ MDWO2037704 MLS ⋅ None Available BLDG.
Enjoy coastal living in the only end-unit Mozart model townhome with the rare addition of a top floor balcony. Less than 1.5 years old, this spacious home offers the feel of a single-family residence with the ease of low-maintenance townhome living. Inside, you’ll find a bright, open-concept main level with seamless flow between the living, dining, and kitchen areas ideal for everyday living and entertaining. The kitchen features modern finishes, ample cabinetry, and generous counter space, while durable flooring enhances both style and functionality. Multiple levels provide flexible living options, including additional space perfect for guests, a home office, or an additional living area. Key features include a rear-entry two-car garage, multiple outdoor spaces, and a top-floor balcony offering a relaxing spot to unwind. The unique upper level adds privacy and versatility, setting this home apart within the community. Located in the amenity-rich Landings at Bayside community, residents enjoy access to a clubhouse, pools, fitness center, walking trails, kayak launch, and more. Ideally situated just minutes from Ocean City, Berlin, Assateague Island, shopping, dining, and local golf courses, this home offers both convenience and a true coastal lifestyle. Move-in ready and perfectly positioned don’t miss this opportunity to own a standout property near the beach!

12461 Coastal Marsh Dr Unit 101, Berlin
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