Chesapeake VA County Homes under $300,000

Welcome to Chesapeake, Virginia—a vibrant city that seamlessly blends suburban charm with urban convenience. Nestled in the heart of Hampton Roads, Chesapeake is known for its picturesque landscapes, rich history, and a strong sense of community. With its sprawling parks, serene waterways, and a variety of recreational activities, Chesapeake offers an ideal environment for families, young professionals, and retirees alike.

For those seeking affordable housing options, Chesapeake is a hidden gem. The real estate market here features a fantastic selection of homes priced under $300,000, making it an attractive choice for first-time homebuyers or anyone looking to downsize without sacrificing quality of life. These homes come in various styles, from cozy single-family residences to charming townhouses, each offering unique features and potential for personalization.

Living in Chesapeake means you’ll enjoy easy access to top-rated schools, a diverse array of shopping and dining options, and a plethora of outdoor activities. Explore the beautiful Great Dismal Swamp National Wildlife Refuge, or take a leisurely stroll along the Elizabeth River. With convenient access to major highways, commuting to nearby cities such as Norfolk and Virginia Beach is a breeze.

In Chesapeake, you’ll find more than just a home; you’ll discover a welcoming community that values connection and growth. Whether you’re starting a new chapter or looking for a peaceful retreat, the homes under $300,000 in Chesapeake offer the perfect opportunity to invest in your future while enjoying all the wonderful amenities this city has to offer. Come and experience the charm of Chesapeake, VA—where your dream home awaits!

Newest Chesapeake VA County Homes under $300,000

$249,900

4 Beds ⋅ 2.1 Baths ⋅ 10658794 MLS

Investor special! Priced 150k+ below renovated value. Property conveys as-is. Seller makes no representations or warranties regarding property condition. Buyer to verify all information in the listing.

801 Drawbridge Drive, South Chesapeake

$300,000

2 Beds ⋅ 1 Baths ⋅ 10658774 MLS

Discover 1.5 acres in the heart of Great Bridge, offering a country feel with everyday conveniences nearby. Explore the possibilities of renovating the existing home or starting fresh with a new home designed around your vision. The spacious parcel offers potential for a new residence and large detached workshop, subject to zoning, septic requirements and necessary approvals. Served by city water and a septic system, the property is conveniently located near Great Bridge Elementary, Middle and High schools. Enjoy the space and setting of acreage while remaining close to shopping, dining and local amenities. Property is being sold strictly as-is; the seller will make no repairs.

1153 Waters Road, South Chesapeake

$230,000

3 Beds ⋅ 2 Baths ⋅ 10658673 MLS

Property being sold "AS IS". Appliances convey "AS IS". Contents and debris in and on the property at settlement convey. Due diligence should be completed prior to submitting offer. No contingencies please. Property is being sold by a Conservator and, as a result, requires approval by a Commissioner of Accounts before any contract can be ratified.

2921 Hilton Avenue, Central Chesapeake

$258,500

3 Beds ⋅ 2 Baths ⋅ 10658490 MLS

Stop and look at this Beautiful Townhome located in the Heart of Chesapeake. Roof less than 5 years old!!!, Updated interior, Granite Counters Tops, Spacious Vaulted Great Room opens to the Kitchen. Premium Laminate Wood Floors, 2nd Floor Master w/Bath. Priced to sell! Call today to schedule to view before this Great Home is SOLD!

822 Wickford Drive, South Chesapeake

$299,900

3 Beds ⋅ 1.1 Baths ⋅ 10657784 MLS

REMODELED, NEW TILE IN BATHROOMS, NEW BATHROOM VANITIES, GRANITE KITCHEN COUNTER TOPS, NEW KITCHEN CABINETS, NEW FLOORS, NEW FIXTURE LIGHTS, NEW WINDOWS, NEW HVAC, NEW STAINLESS STEEL APPLIANCES AND MUCH MORE

904 Mckinley Avenue, Central Chesapeake

$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

$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

MUST SEE! Beautiful move-in ready home with fantastic updates, including a new roof, siding, flooring, appliances, fresh paint, and more. Features spacious bedrooms, an open-concept layout, and a great kitchen. Situated on a large lot (nearly 6,800 sq. ft.) with a massive backyard offering endless possibilities. Conveniently located near shopping, dining, military bases, and the airport. Schedule your private tour today!

2432 Youngman Road, 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

$233,500

2 Beds ⋅ 2 Baths ⋅ 10657659 MLS

Low-maintenance living with a little poolside fun? Yes, please! Welcome to this beautifully maintained 2-bedroom, 2-bath condo in Chesapeake. Tucked away in a quiet corner location, this home offers comfortable living with the convenience of easy interstate access. Enjoy peace of mind with an HVAC system just 3 years old and a water heater only 1 year old. The community pool is included with the HOA, making it easy to enjoy a little fun in the sun without the upkeep. One assigned parking space plus plenty of visitor parking adds to the convenience. Well cared for and ready for its next chapter, this condo is a charming place to call home!

710 Rue Marseille, South 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.

Chesapeake VA County Homes under $300,000

Newest Chesapeake VA County Homes under $300,000

How much is your home worth?

How much is your home worth?