Bayside Homes under $400,000

Bayside Homes under $400,000

Welcome to Bayside, a hidden gem nestled in the heart of the United States, where coastal charm meets suburban tranquility. This enchanting subdivision offers a unique blend of picturesque landscapes and modern conveniences, making it the perfect place for families, young professionals, and retirees alike. With its welcoming community spirit and a variety of recreational amenities, Bayside is not just a neighborhood; it’s a lifestyle.

One of the most appealing features of Bayside is its diverse range of homes priced under $400,000. Whether you’re a first-time homebuyer or looking to downsize, you’ll find an array of options that cater to your needs. From cozy single-family homes with lush backyards to stylish townhomes with contemporary finishes, there’s something for everyone in this vibrant community. The affordability of these homes makes it easier to settle into your dream abode without breaking the bank.

Bayside is also conveniently located near shopping centers, parks, and schools, ensuring that everything you need is just a stone's throw away. Spend your weekends exploring the scenic trails, enjoying family picnics at the local parks, or indulging in the delightful eateries that line the streets. The community hosts regular events, fostering connections among neighbors and creating lasting friendships.

If you’re searching for a place that combines affordability with a sense of belonging, Bayside is the ideal choice. Come and discover your new home in this charming subdivision, where the possibilities are endless and the community is truly one of a kind!

Newest Bayside Homes under $400,000

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.

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:

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
$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:

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:

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