Bayside Homes under $500,000

Bayside Homes under $500,000

Welcome to Bayside, a hidden gem nestled in the heart of the United States that perfectly marries suburban tranquility with vibrant community life. This charming subdivision is an ideal destination for families, first-time homebuyers, and anyone seeking a serene yet engaging neighborhood. With its picturesque streets lined with beautiful trees and friendly neighbors, Bayside offers a warm and inviting atmosphere that truly feels like home.

One of the standout features of Bayside is its affordability. Here, you can find a variety of homes priced under $500,000, making it an accessible option for those looking to invest in their future without breaking the bank. Whether you’re searching for a cozy single-family home, a stylish townhome, or a spacious condo, Bayside has something to suit every taste and lifestyle. Many of these homes boast modern amenities, open floor plans, and beautiful outdoor spaces, perfect for entertaining or enjoying quiet evenings.

In addition to its attractive real estate options, Bayside is conveniently located near essential amenities, including shopping centers, schools, parks, and recreational facilities. Residents can enjoy leisurely walks along scenic trails, participate in community events, and take advantage of the vibrant local culture.

If you’re ready to discover your dream home in a welcoming neighborhood with a strong sense of community, look no further than Bayside. With homes under $500,000, your perfect piece of paradise awaits! Come explore the possibilities and make Bayside your new home sweet home.

Newest Bayside Homes under $500,000

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:

8663 Bat Creek Loop Ln Unit 3, Berlin
$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:

108 Blenny Ln, Chester
$369,900
3 Beds ⋅ 3 Baths
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

Listing courtesy of RE/MAX Leading Edge. Contact:

11145 Signature Blvd, Selbyville
$469,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Keller Williams Realty. Contact:

31568 Winterberry Pkwy Unit 309, Selbyville
$389,000
4 Beds ⋅ 3 Baths
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

Listing courtesy of EXP Realty, LLC. Contact:

8663 Bat Creek Loop Ln Unit 1, Berlin
$449,900
4 Beds ⋅ 4 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact:

807 Auckland Way, Chester
$425,500
3 Beds ⋅ 4 Baths
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

Listing courtesy of Real Broker, LLC - Chester. Contact:

106 Bodys Neck Rd, Chester
$429,900
3 Beds ⋅ 3 Baths
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

Listing courtesy of Realty Navigator. Contact:

12461 Coastal Marsh Dr Unit 101, Berlin
$474,900
4 Beds ⋅ 5 Baths
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

Listing courtesy of Coastal Life Realty Group LLC. Contact:

8673 Bat Creek Loop Ln Unit 2, Berlin
$464,900
4 Beds ⋅ 5 Baths
Practically brand new and built in 2024 by Ryan Homes, this stunning 4-level townhouse is located in the highly desirable, luxury Bayside community in the West Ocean City/Berlin area. Offering over 2,400 sq ft, this spacious home features 4 bedrooms, 3 full baths, and 2 half baths—designed with both comfort and functionality in mind. The entry level includes a versatile office or bonus space, a half bath, additional storage, and access to the garage. Head upstairs to the main living level where you’ll find an open-concept layout with a bright living room, dining area, and a beautifully upgraded kitchen complete with quartz countertops, stainless steel appliances, a large island, and a separate coffee/wine bar—perfect for entertaining. Luxury vinyl plank flooring runs throughout the first and second levels. The third floor offers three bedrooms, including a spacious primary suite with a walk-in closet, dual sink vanity, tiled walk-in shower, and a separate tiled soaking tub. Laundry is conveniently located on this level as well. The fourth floor provides a flexible space that can serve as a bedroom or additional living area, complete with a full bath and access to a private balcony showcasing peaceful pond views and a glimpse of the bay. Enjoy resort-style living with community amenities that include a clubhouse, fitness center, indoor and outdoor pools, a crabbing pier, and a kayak launch. The association covers additional things like landscaping and lawn care, making for easy, low-maintenance living. Ideally located just minutes from the beach, dining, and entertainment, yet tucked away in a peaceful community setting—you truly get the best of both worlds. Don’t wait—schedule your private showing today!

8673 Bat Creek Loop Ln Unit 2, Berlin

Listing courtesy of Coldwell Banker Realty. Contact:

11043 Destination Dr, Selbyville
$499,000
3 Beds ⋅ 3 Baths
Beautiful coastal home just 4 miles from the beach in the award-winning community of Bayside! This home features a stunning great room with soaring ceilings, a gas fireplace, new LVP flooring, and an open floor plan ideal for entertaining. The dine-in kitchen offers Corian countertops, ample cabinetry, and a breakfast nook. Enjoy outdoor living on the screened porch, or retreat to the first-floor primary suite featuring a completely renovated en-suite bath that was thoughtfully redesigned with an expanded tiled walk-in shower and dual-sink vanity. Upstairs, a spacious loft provides additional living space, along with two oversized bedrooms connected by a Jack-and-Jill bath. A 2-car garage offers plenty of storage for beach and golf gear. Ideally located near the community entrance, the home is just steps from Freeman Stage, the indoor pool and fitness center, golf course, and restaurant. Bayside offers an impressive array of resort-style amenities, including multiple outdoor pools, Jack Nicklaus Signature Golf, tennis, fitness centers, trails, water access, dog parks, concerts, and a beach shuttle to Fenwick Island State Park.

11043 Destination Dr, Selbyville

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

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