Bayside Homes under $900,000

Bayside Homes under $900,000

Welcome to Bayside, a serene and vibrant subdivision that perfectly captures the essence of coastal living in the United States. Nestled along picturesque shores, Bayside offers residents an idyllic escape with its stunning waterfront views and a welcoming community atmosphere. This charming neighborhood is not just about breathtaking scenery; it also boasts an array of amenities designed to enhance your lifestyle.

In Bayside, you’ll find a diverse selection of homes, many of which are available for under $900,000. This makes it an ideal destination for first-time buyers, families, and those looking to downsize without compromising on quality or location. The homes in this subdivision are characterized by their modern designs, spacious layouts, and beautiful landscaping, ensuring that you can find the perfect fit for your needs.

Residents of Bayside enjoy easy access to pristine beaches, scenic parks, and a variety of recreational activities. Whether you prefer a leisurely stroll along the shoreline, a day of fishing, or exploring local trails, the options are endless. Additionally, the community is conveniently located near shopping centers, dining establishments, and top-rated schools, making everyday life convenient and enjoyable.

Bayside is not just a place to live; it’s a lifestyle choice. With its affordable homes, vibrant community spirit, and breathtaking natural beauty, Bayside invites you to discover the perfect blend of comfort and coastal charm. Come and explore all that this enchanting subdivision has to offer—your dream home awaits!

Newest Bayside Homes under $900,000

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:

31207 Whitecap Way, Selbyville
$849,000
4 Beds ⋅ 4 Baths
Welcome to this beautifully maintained Seagrass model twin villa by Schell Brothers, ideally positioned on a desirable corner lot in Bayside, one of coastal Delaware’s premier resort communities. Built in 2016, this 4-bedroom, 3.5-bath home combines coastal style, comfortable living spaces, and exceptional indoor and outdoor amenities—making it an ideal primary residence, vacation home, or investment property. From the moment you enter, you’ll appreciate the open-concept floor plan, gleaming hardwood floors, soaring cathedral ceilings, recessed lighting, and inviting gas fireplace. The spacious family room flows seamlessly into the dining area and gourmet kitchen, creating an ideal layout for entertaining or relaxing with family and friends. The well-appointed chef’s kitchen features crisp white cabinetry, abundant storage, a walk-in pantry, stainless steel appliances, built-in microwave, dishwasher, single oven, and a large center island with plenty of workspace and seating. A convenient breakfast area provides the perfect spot for morning coffee, while the adjacent dining area overlooks the scenic surroundings. The first-floor primary suite offers a private retreat with a spa-inspired en suite bath. Upstairs, you’ll find a spacious loft, three additional bedrooms, and ample flexibility for guests, hobbies, or a home office. A dedicated den/office with built-in cabinetry provides an ideal work-from-home space. Outdoor living is a true highlight. Enjoy the privacy and comfort of the screened-in porch, or step onto the paver patio with built-in grill and outdoor fireplace—perfect for summer entertaining, al fresco dining, or relaxing around the fire. The exterior has been meticulously maintained, including siding replaced in February, providing added peace of mind and enhanced curb appeal. The attached two-car garage offers convenient parking and additional storage, while the professionally landscaped exterior complements the home's attractive corner-lot setting. Living in Bayside means enjoying an extraordinary resort lifestyle with amenities that include the Jack Nicklaus Signature Golf Course, clubhouse with bar and restaurants, tennis courts, multiple indoor and outdoor pools, state-of-the-art fitness centers, bayfront beach area, kayaking, biking and walking trails, beautifully maintained common grounds, and live entertainment at the renowned Freeman Arts Pavilion. Located in coastal Delaware near Fenwick Island and Ocean City, this exceptional Bayside villa puts you close to beaches, golf, dining, shopping, entertainment, and year-round recreation. Whether you're looking for a full-time residence, a Delaware beach getaway, or an investment opportunity, this Schell Brothers Seagrass model in Bayside offers the ideal combination of comfort, community, and coastal resort living

31207 Whitecap Way, Selbyville

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

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
$599,900
3 Beds ⋅ 4 Baths
New Listing! Bayside Condos * End Unit with Garage * Direct Water Views * Direct View of Castle Harbor Marina * Best Location in the Community* Potential to See Your Boat From Your Window * Many Upgrades * Renovated Kitchen * Renovated Primary Bath * Balcony Off Primary w Water Views * Large Walk-In Closet * Dramatic Ship Lap Accent Wall * Waterside Double Width Deck * Dual Zoned HVAC * Community Pool, Hot Tub, Tennis, Volleyball, Exercise Room and On-Site Property Manager * Condo Dues Cover Roof, Siding, Gutters, Lawn Care, Grass Cutting, Pest Control * Public Water, Public Sewer * Gas Fireplace * Convenient Chester Location Close To Shopping and Grocery

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:

1010 Auckland Way, Chester
$595,000
3 Beds ⋅ 4 Baths
PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the Eastern Shore lifestyle! Beautiful hardwood floors flow throughout the main level, where the kitchen, dining room and family room all take advantage of the spectacular water views. The modern kitchen opens to the living areas, while built-in bookcases and a gas fireplace add character and function to the family room. Step outside to one of two waterside decks and enjoy the ever-changing river views, passing boats and beautiful scenery. Upstairs, wake up each morning to endless WATER VIEWS from the Primary Suite, then step directly onto your private waterside deck with your morning coffee. Bedrooms feature the privacy and convenience of ensuite baths. A large upper-level Bonus Room with its own full bath provides wonderful flexibility—create a 3rd bedroom, spacious home office, a guest suite, den or whatever best fits your lifestyle. The views are even better from up here! Freshly painted and truly MOVE-IN READY, this light-filled end unit offers the combination everyone is looking for—beautiful interiors, flexible living space, two waterside decks and an exceptional location overlooking the Chester River. Bayside offers wonderful community amenities, including a swimming pool, party room, fitness center, tennis/pickleball courts and volleyball. The 38+ mile Cross Island Trail is just around the corner for walking, jogging and biking. You’re also conveniently located near restaurants, grocery shopping, outlet shopping and golf courses. Love boating? The marina bordering the community offers boat slips that may be available for rent or purchase, making it easy to enjoy everything the Chesapeake Bay and Eastern Shore have to offer. Come experience the Kent Island waterfront lifestyle—beautiful views, boating, recreation and convenience, all right outside your door!

1010 Auckland Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

36375 Sea Grass Way, Selbyville
$750,000
3 Beds ⋅ 3 Baths
Welcome to 36375 Sea Grass Way, a beautifully appointed end-unit townhome in the highly desirable bayfront amenity rich Jack Nicklaus golf course community- Bayside. With 3 bedrooms, 2.5 baths, a first-floor primary suite, attached garage, and tranquil pond views, this coastal retreat offers the ideal combination of comfort, space, and low-maintenance living. Step inside to a light-filled, open-concept floor plan featuring hardwood flooring, crown molding, recessed lighting, and an easy flow between the kitchen, dining, and living areas. The gourmet kitchen is designed for both everyday living and entertaining with quartz countertops, a generous center island, breakfast bar, pantry, stainless steel appliances, cooktop, and wall oven. The spacious main-level primary suite offers a walk-in closet and private bath, allowing for convenient one-level living. A sitting area, powder room, and main-floor laundry complete the first level. Just beyond the living space, the screened porch and hardscape patio provides a peaceful place to relax, dine outdoors, and enjoy the surrounding pond and water views. Upstairs, guests will appreciate two generously sized bedrooms with walk-in closets, a full bath, and a spacious family room that provides flexible additional living space. A storage room adds even more functionality to the home. The property is being offered partially furnished, making the transition to coastal living easier. Located within Bayside, residents enjoy access to an exceptional collection of amenities including indoor and outdoor pools, fitness facilities, tennis and pickleball courts, playground, dog park, walking and jogging paths, clubhouse facilities, community dock and pier, beach access, restaurants, The Freeman Arts Pavilion, and golf with membership opportunities available. Whether you are searching for a primary residence or coastal getaway, 36375 Sea Grass Way 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.

36375 Sea Grass Way, Selbyville

Listing courtesy of Northrop Realty. Contact:

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