Chesapeake VA County Homes under $500,000

Welcome to Chesapeake, Virginia, a vibrant and welcoming community that embodies the perfect blend of suburban charm and urban convenience. Nestled in the heart of Hampton Roads, Chesapeake boasts a rich history, lush landscapes, and a wealth of recreational opportunities. With its scenic waterways, extensive parks, and top-rated schools, it’s no wonder this city is a sought-after destination for families, professionals, and retirees alike.

One of the most appealing aspects of Chesapeake is its diverse real estate market, particularly for those seeking homes under $500,000. Whether you’re a first-time homebuyer, looking to downsize, or searching for a family-friendly abode, Chesapeake offers a variety of charming properties to suit your needs. From cozy single-family homes in established neighborhoods to modern townhouses with contemporary finishes, there’s something for everyone in this thriving market.

Imagine settling into a beautiful home where you can enjoy the tranquility of suburban living while still being just a short drive away from the bustling cities of Norfolk and Virginia Beach. With easy access to major highways and a wealth of shopping, dining, and entertainment options nearby, Chesapeake allows you to enjoy the best of both worlds.

Explore the inviting neighborhoods that make up this wonderful city, each with its unique character and community spirit. With homes priced under $500,000, you can find a place that not only fits your budget but also your lifestyle. Come discover why Chesapeake, VA, is the perfect place to call home!

Newest Chesapeake VA County Homes under $500,000

$299,900

3 Beds ⋅ 2.1 Baths ⋅ 10657730 MLS

Enjoy low-maintenance luxury at Estella Villas! This beautifully kept townhome makes daily life simple with hard-surface flooring throughout the first floor and cozy carpet upstairs. The open-concept floor plan is perfect for hosting guests and spending time with family. A welcoming foyer upon entry sets this property apart from many modern builds. The home features high ceilings, and the kitchen overlooks the great room. On weekends, enjoy a barbecue on your private patio and embrace simple living without the stress of tedious yard work. Large bedrooms, granite countertops, master bedroom with en suite bathroom, double vanity sink, and walk-in closet. Conveniently located 12 minutes or less from downtown Norfolk, Greenbrier Mall. This one is stunning and upscale. Schedule your showing today!

216 Astra Lane, Central Chesapeake

2035 Christian Avenue, Central Chesapeake

$310,000

3 Beds ⋅ 2.1 Baths ⋅ 10657931 MLS

Discover the perfect place to call home in this inviting 3 bedroom, 2.1 bathroom home! Featuring an open concept layout great for everyday living and entertaining, spacious closets for all your storage needs, and a fenced backyard great for outdoor enjoyment, this home offers comfort and convenience. Enjoy a convenient location near a variety of amenities, shopping, dining, and recreational activities. Whether you're looking for a place to relax or entertain, this home is ready for its next chapter with you!Don’t miss your opportunity to make it yours today!

2035 Christian Avenue, Central Chesapeake

$383,500

4 Beds ⋅ 2 Baths ⋅ 10657925 MLS

This property has been thoughtfully updated from top to bottom, offering modern finishes and peace of mind for its next owner. Improvements include a new roof, HVAC system, water heater, fully updated kitchen and bathrooms, new outlets and switches, doors, flooring, and stylish light fixtures, plus much more. Fresh interior and exterior paint give the home a clean, bright, and refreshed look. With numerous upgrades throughout, this property is ready for you to move in and make it your own. Don’t miss the opportunity to own this beautifully refreshed home!

2941 Guenevere Drive, South Chesapeake

$279,900

2 Beds ⋅ 2.1 Baths ⋅ 10657138 MLS

Come See this Beautifully Maintained 2 Bedroom 2 1/2 Bathroom Condo in the Heart of Western Branch. Open Concept Kitchen with Breakfast Bar and Dining Area. SS Appliances and Quartz Countertops. Large Living Room with Slider to your Private Patio and Storage Shed. Laundry Closet. 2 Bedrooms with Ensuite Baths and Walk-In Closet Located Upstairs along with a Spare Room which can be used as an Office, Nursery, Craft Room or Storage. Community Amenities Include Ground Maintenance, Pool, Water and Trash. Conveniently Located Near Interstate, Shopping, Dining, Parks and Library. Welcome Home!

2456 Whitman Street, West Chesapeake

1221 Commerce Avenue, Central Chesapeake

$279,725

3 Beds ⋅ 2.1 Baths ⋅ 10657786 MLS

A 2.75% ASSUMABLE MORTGAGE, UPDATED FEATURES, AND A FIRST-FLOOR PRIMARY SUITE! This Chesapeake home offers a combination of comfort, functionality, and potential financing advantages worth exploring. The bright, inviting kitchen features stainless steel appliances, updated cabinetry, and granite countertops, while water-resistant laminate flooring, ceramic tile, updated lighting, and ceiling fans add appeal throughout the home. The spacious first-floor primary suite features a vaulted ceiling, creating an open and relaxing retreat with an exceptional walk-in closet. Step outside to enjoy the deck and outdoor space, great for unwinding or entertaining, with the added convenience of a detached garage for parking, storage, or hobbies. If you're searching for an updated Chesapeake home with a first-floor primary suite and outdoor living space, this property deserves a closer look!

1221 Commerce Avenue, Central Chesapeake

$275,000

2 Beds ⋅ 2 Baths ⋅ 10657817 MLS

Welcome to highly sought-after, single-story living in the wonderful 55+ community of One Ford Place! This beautifully maintained Western Branch condo offers the ultimate "no-maintenance" lifestyle. The inviting layout features a spacious great room with sliding doors opening to a private patio. The well-appointed kitchen includes a pantry and conveys with all appliances. Enjoy a luxurious primary suite adorned with picture frame molding and a beautiful en-suite bath featuring a granite double vanity, tub, and separate shower. A second bedroom and full bath on the opposite side of the home create the perfect private guest suite! Enjoy the rare convenience of a one-car garage, a two-car driveway, and ample guest parking. Move in with total peace of mind thanks to major recent updates to the HVAC, water heater, and appliances. With TVs conveying and additional furniture negotiable, your transition will be a breeze. Located minutes from the YMCA, I-664, and I-164!

3301 Settlement Court, West Chesapeake

$262,500

2 Beds ⋅ 1 Baths ⋅ 10657727 MLS

Big backyard. Beautiful updates. Small price tag! Who says homeownership has to break the bank? Welcome to this charming 2 bedroom, 1 bath home in Loxley Gardens, offering the opportunity to own a move in ready home for under $300K! Enjoy a cute kitchen with brand new appliances, new flooring, a new roof, and new siding. The real showstopper? A MASSIVE backyard with endless possibilities for entertaining, pets, gardening, or creating your own outdoor oasis. Whether you're a first time buyer or looking to downsize, this one checks the boxes! Schedule your private tour today!

2432 Youngman Road, South Chesapeake

$360,000

3 Beds ⋅ 2 Baths ⋅ 10657719 MLS

Welcome to 3019 Roundtable Drive. A charming ranch-style home in the heart of Chesapeake. This 3-bedroom, 2-bathroom home offers an open layout everyday life or entertainment. recent updates include granite countertops w/backsplash in kitchen, new Roof, HVAC-2026, Hot water Heater-2026 and fresh paint throughout home. Outside, there’s a large backyard that offers plenty of space for entertaining, gardening, or play. Conveniently located on a quiet cul-de-sac near shopping, dining, and local amenities, this home is ready to welcome you. Fence and shed convey as is. Schedule your showing today!

3019 Roundtable Drive, South Chesapeake

1253 Quarter Path Trail, South Chesapeake

$365,000

3 Beds ⋅ 2 Baths ⋅ 10657920 MLS

Located on a quiet cul-de-sac in a highly desirable Turtle Rock neighborhood, this property offers privacy, a peaceful setting ideal for buyers seeking a home in an established residential community! The spacious rooms with a backyard that overlooks the water sets this home apart. Just minutes away from Greenbrier shopping and restaurants while also close to major roadways and military bases this home has the location and shine for all to see!

1253 Quarter Path Trail, South Chesapeake

$375,000

4 Beds ⋅ 3 Baths ⋅ 10656923 MLS

2406 Drum Creek Rd, Chesapeake VA 23321 is a 1,288-square-foot home built in 1962. A fireplace anchors the main living area, adding warmth and ambiance to the central gathering space. The primary bathroom includes double sinks for everyday convenience. Outdoors, a storage shed adds extra utility. This residence combines practical design with comfortable living spaces, delivering functional amenities throughout every room.

2406 Drum Creek Road, West Chesapeake

$415,900

3 Beds ⋅ 2.1 Baths ⋅ 10657874 MLS

Welcome to this beautifully maintained home in the highly sought after Cardinal Meadows neighborhood! A bright, open layout designed for comfortable everyday living and effortless entertaining. The kitchen features granite countertops, ample workspace, and flows seamlessly into the main living areas. Natural light throughout creates a warm and inviting atmosphere. Move-in ready and waiting for its new owners, this home offers the perfect combination of comfort, style, and functionality. Enjoy added privacy and peace of mind with a fully fenced backyard, featuring a low-maintenance vinyl privacy fence- perfect for pets, entertaining or relaxing outdoors.

1625 Redwing Arch, South Chesapeake

$197,500

3 Beds ⋅ 1.1 Baths ⋅ 10657866 MLS

Spacious 3-bedroom, 1.5-bath home in the heart of South Norfolk offering over 1,300 sq ft of living space. Property needs some TLC but presents tremendous potential for investors or buyers looking to build equity. Bring your vision and really make this home shine! Conveniently located near dining, shopping, the interstate, and more! Call today for more information and to schedule your tour!

710 B Street, Central Chesapeake

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Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.