Central Chesapeake Homes under $300,000

Welcome to Central Chesapeake, Virginia – a vibrant and welcoming community that perfectly balances suburban charm with urban convenience. Nestled in the heart of Chesapeake County, this area is renowned for its picturesque landscapes, friendly neighborhoods, and a rich tapestry of local culture. Central Chesapeake boasts an array of parks, recreational facilities, and shopping centers, making it an ideal place for families, young professionals, and retirees alike.

One of the most appealing aspects of Central Chesapeake is its diverse real estate market, particularly for those seeking homes under $300,000. Here, you’ll find an impressive selection of affordable properties that cater to various lifestyles and preferences. From cozy single-family homes to modern townhouses, there’s something for everyone in this price range. Many of these homes feature spacious layouts, updated amenities, and beautiful outdoor spaces, perfect for enjoying Virginia's temperate climate.

In addition to its attractive housing options, Central Chesapeake is conveniently located near major highways, making commuting to nearby cities a breeze. Residents also enjoy access to highly-rated schools, vibrant local dining, and a host of community events throughout the year.

Whether you’re a first-time homebuyer or looking to downsize, Central Chesapeake offers an exceptional quality of life without breaking the bank. Embrace the opportunity to find your dream home in this delightful city, where affordability meets charm – your perfect slice of Virginia awaits!

Newest Central Chesapeake Homes under $300,000

$267,700

3 Beds ⋅ 2 Baths ⋅ 10656397 MLS

Completely remodeled three bedroom, two bath with new LVP flooring, new carpet, a brand new kitchen, and updated bathrooms. One bedroom and a full bath are downstairs, which works well for guests, an office, or anyone who would rather skip the stairs. There's a front porch out front, and the backyard is large, with plenty of off street parking. Lakeside Park sits right around the corner, with a lake you can fish, two playgrounds, covered pavilions, and a walking path through the trees. Elizabeth River Park is about a mile up the road and has a dog park, a fishing pier, a boat ramp, and a paved path along the water. I-464 puts you in downtown Norfolk in about ten minutes. Updated and ready for its next owner.

1318 18th Street, Chesapeake

$289,900

3 Beds ⋅ 1.1 Baths ⋅ 10656065 MLS

Don’t miss this charming brick starter home offering 3 bedrooms, 1.5 baths, and just under 1,200 sq. ft. The updated kitchen, newer roof, HVAC, and windows (all under 5 years old) provide peace of mind, while the fully fenced backyard offers plenty of space to relax or play. Conveniently located near interstates, military bases, shopping, and restaurants, and zoned for Indian River schools. A great opportunity to add your personal touches and make it your own!

718 Osborn Avenue, Chesapeake

$249,900

3 Beds ⋅ 1.1 Baths ⋅ 10655854 MLS

Charming 3-bedroom, 1.5-bath townhome on Hearthside Court in Chesapeake, offering approximately 1,291 square feet across two stories. Features include beautiful wood-pattern LVP floors, stainless steel appliances, and abundant natural light. Conveniently located near shopping, dining, entertainment, and interstate access. Contact the listing office today!

1809 Hearthside Court, Chesapeake

$229,900

1 Beds ⋅ 1 Baths ⋅ 10655691 MLS

Welcome home to this move-in ready Chesapeake gem! This bright and inviting one-bedroom, one-bath home offers an open-concept layout with the kitchen overlooking the living area, creating a functional space for everyday living and entertaining. Enjoy your own private patio, perfect for relaxing outdoors. A brand-new HVAC system. Conveniently located near Greenbrier, Kempsville, shopping, dining, parks, and major interstates, this home offers easy access to everything Chesapeake and the surrounding area have to offer. Whether you're purchasing your first home, looking to downsize, or searching for an investment property, this is an opportunity you won't want to miss.

2005 Lockard Avenue, Chesapeake

$225,000

3 Beds ⋅ 1 Baths ⋅ 10655557 MLS

Charming 3 bedroom, 1 bath home situated on a deep 42' x 155' lot with plenty of outdoor space to enjoy. Inside, you'll find a comfortable living room with an accent wall, an eat-in kitchen with ample cabinetry and counter space, and a separate laundry area. All three bedrooms offer good natural light, with the primary bedroom featuring generous closet storage. A covered front porch adds a welcoming spot to relax, while the spacious backyard offers room for entertaining, gardening or future outdoor projects. The detached garage/workshop is equipped with electrical service, providing additional storage and a versatile space for hobbies or projects. Unapproved short sale. Property is being sold AS-IS. Seller to make no repairs.

1225 Jackson Avenue, Chesapeake

$275,000

4 Beds ⋅ 2 Baths ⋅ 10655376 MLS

Beautifully updated 4 bedroom, 2 bath home in Chesapeake! Spacious home that features modern updates throughout and offers easy access to nearby interstates for a quick commute. Don’t miss the amazing blend of style, comfort, and convenience!

1321 Seaboard Avenue, Chesapeake

$279,900

4 Beds ⋅ 1 Baths ⋅ 10655177 MLS

Welcome to this charming two-story Cape Cod offering 4 bedrooms and a spacious open floor plan designed for comfortable living. The home's inviting layout provides plenty of room for family gatherings and everyday enjoyment. Living room, dinning room, eat-in kitchen, 2 bedrooms on 1st floor and 2 bedrooms on 2nd floor. A full family bathroom serves the home, while the generous bedroom count offers flexibility for guests, a home office, or growing households. Newer water heater and windows have been replaced. This property is being sold as-is, and presents a great opportunity for homeowners or investors looking to add their personal touches and build equity.

605 Wingfield Avenue, Chesapeake

$299,900

3 Beds ⋅ 1 Baths ⋅ 10655176 MLS

Charming Cape Cod-style home situated on a desirable corner lot, offering plenty of character and potential. Features a spacious eat-in kitchen, beautiful hardwood floors, and a large living room highlighted by a cozy fireplace. The main level includes two comfortable bedrooms and a full family bathroom, while the second floor boasts a generously sized bedroom, providing additional privacy and space. An oversized detached garage with large driveway offers ample room for parking, storage, or a workshop. This two-story home is being sold as-is, presenting a great opportunity for homeowners, investors, or those looking to add their personal touch.

601 Wingfield Avenue, Chesapeake

1016 Thoroughgood Way Unit 302, Chesapeake

$225,000

2 Beds ⋅ 2 Baths ⋅ 10654835 MLS

Welcome to Village at Gateway in the heart of South Norfolk! This beautifully maintained third-floor condo is easily accessed via elevator and features an open-concept floor plan with oversized rooms and abundant natural light from skylights. The upgraded kitchen provides ample cabinetry, a pantry, and bar seating for four for casual dining or entertaining. Enjoy indoor-outdoor living with a spacious 8x12 covered porch just off the living room. The primary suite includes a glass-enclosed shower and dual closets, while the second bedroom is generously sized for guests or a home office. Additional highlights include in-unit stacked washer and dryer, secured building access, and gated parking with fob entry. Conveniently located near shopping, dining, and major interstates, don’t miss this opportunity for low-maintenance living!

1016 Thoroughgood Way Unit 302, Chesapeake

$220,000

2 Beds ⋅ 1 Baths ⋅ 10655021 MLS

Welcome to 901 Stewart Street! This charming 2-bedroom, 1-bath ranch offers comfortable single-level living in the South Norfolk area of Chesapeake. With approximately 825 square feet, the home features a functional layout with plenty of opportunity to make the space your own. Enjoy a spacious yard with room for outdoor entertaining, gardening, or creating your own outdoor retreat. Conveniently located near shopping, dining, major roadways, and everyday amenities, this property offers easy access throughout Chesapeake and surrounding Hampton Roads. Whether you're looking for your next home or an investment opportunity, 901 Stewart Street is ready for its next chapter. Schedule your private showing today!

901 Stewart Street, Chesapeake

$297,000

4 Beds ⋅ 2.1 Baths ⋅ 10654794 MLS

This 3-bedroom, 2.5-bath home is waiting for you! It offers approximately over 1,600 square feet of living space on a manageable 0.086-acre lot. The property could benefit from some updating and offers an excellent opportunity to add value with improvements and personal touches. A great option for investors, renovators, or buyers looking to build equity and make a home their own. Call today for more information and to schedule your tour!

1055 Calloway Avenue, Chesapeake

$284,900

3 Beds ⋅ 2 Baths ⋅ 10654894 MLS

Welcome to 4210 Bainbridge Boulevard! This charming 3-bedroom, 2-bath home offers 900 square feet of thoughtfully designed living space with a versatile front flex room—great for a home office, playroom, or cozy sitting area. Enjoy the convenience of living in Chesapeake without the close-neighbor feel of a traditional subdivision. The neighboring property at 4212 Bainbridge Boulevard is also available, creating a rare opportunity to purchase both homes—amazing for extended family, multigenerational living, or living in one home while renting the other. Don’t miss this unique and flexible opportunity! Seller is Offering extra credits to buyer towards buy down rate.

4210 Bainbridge Boulevard, Chesapeake

Start Your Search

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.