Bayside Homes under $400,000

Bayside Homes under $400,000

Welcome to Bayside, a vibrant subdivision nestled in the heart of the United States, where charm meets convenience. This picturesque community is an ideal destination for homebuyers seeking a balance of affordability and quality living. With a selection of stunning homes priced under $400,000, Bayside offers an exceptional opportunity for first-time buyers, families, and anyone looking to invest in their dream home without breaking the bank.

Bayside boasts a variety of architectural styles, from cozy single-family homes to modern townhouses, ensuring there’s something for everyone. Each residence is designed with comfort and functionality in mind, featuring spacious layouts, updated kitchens, and inviting outdoor spaces perfect for entertaining or relaxing. The community’s friendly atmosphere is enhanced by tree-lined streets, manicured lawns, and a strong sense of neighborly camaraderie.

Beyond the beautiful homes, Bayside is strategically located near essential amenities. Residents enjoy easy access to shopping centers, dining options, and recreational parks, making daily life a breeze. Families will appreciate the proximity to quality schools and community programs, while outdoor enthusiasts can explore nearby trails and waterways.

Bayside isn’t just a place to live; it’s a community where memories are made and friendships flourish. With homes available for under $400,000, this subdivision presents an incredible opportunity for those looking to settle down in a welcoming environment. Discover the charm of Bayside today, and find your perfect home in this delightful community!

Newest Bayside Homes under $400,000

411 Merganser Ct, Chester
$280,000
2 Beds ⋅ 2 Baths
Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

411 Merganser Ct, Chester

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

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:

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:

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:

108 Blenny Ln, Chester
$364,900
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:

31568 Winterberry Pkwy Unit 309, Selbyville
$359,970
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:

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