Chesapeake VA County Homes under $300,000

Welcome to Chesapeake, Virginia, a vibrant city that beautifully blends suburban charm with urban convenience. Nestled in the heart of Hampton Roads, Chesapeake boasts a rich history, stunning natural landscapes, and a welcoming community spirit. With its extensive parks, scenic waterways, and a plethora of recreational activities, this city is perfect for families, young professionals, and retirees alike.

One of the most enticing aspects of Chesapeake is its diverse real estate market, particularly for those seeking homes under $300,000. Whether you’re a first-time homebuyer or looking to downsize, you’ll find a variety of options that cater to different lifestyles and budgets. From cozy townhomes to charming single-family residences, the homes in this price range offer incredible value without sacrificing quality or comfort.

Chesapeake’s neighborhoods are characterized by tree-lined streets, friendly neighbors, and a strong sense of community. You’ll find properties that are conveniently located near top-rated schools, shopping centers, and dining options. Additionally, the city’s strategic location provides easy access to major highways, making commutes to nearby Norfolk, Virginia Beach, and Portsmouth a breeze.

Investing in a home in Chesapeake not only means securing a comfortable living space but also embracing a community that values connection and growth. With a thriving local economy and a commitment to enhancing the quality of life for its residents, Chesapeake is an ideal place to call home. Explore the incredible opportunities available under $300,000 and discover the charm of Chesapeake, VA—where your dream home awaits!

Newest Chesapeake VA County Homes under $300,000

$252,000

2 Beds ⋅ 1 Baths ⋅ 10656390 MLS

Affordable Great Bridge lake-view living! Enjoy low-maintenance condo living just off Cedar Road, a short drive from shopping, restaurants, entertainment and everything Great Bridge has to offer. Inside, vaulted ceilings, arched windows and abundant natural light give the home an open, inviting feel. The living room features a cozy fireplace and opens to a private balcony overlooking the lake and mature trees—an ideal spot for morning coffee or winding down at the end of the day. The kitchen offers plenty of cabinet and counter space with a bright dining area highlighted by a dramatic arched window. Two comfortable bedrooms and a full bath complete the home. Residents also enjoy community amenities including the pool, while the location puts you just minutes from the area’s dining, shopping and entertainment. The city’s annual parade route is also just a few blocks away, adding to the convenience and community feel of this Great Bridge location. Whether you’re a first-time buyer, downsizing, or simply looking for an affordable, low-maintenance home in a great location, this lake-view condo offers a lot of value without giving up convenience.

449 E Lake Circle, South Chesapeake

713 Rapidan River Court Unit G, South Chesapeake

$230,000

2 Beds ⋅ 2 Baths ⋅ 10655996 MLS

Freshly transformed and move-in ready! This second-floor corner end-unit condo in Chesapeake's Riverwalk community just had a full cosmetic refresh of the interior, including fresh paint throughout, an updated kitchen, new flooring and more. The single-level layout offers 2 bedrooms and 2 full baths. A wood-burning fireplace anchors the living area, and a private balcony overlooks mature trees. The primary suite has its own full bath. Beyond the cosmetic work, the home also has newer windows and a newer HVAC system. Kitchen appliances convey along with an exterior storage shed and two assigned parking spaces. The condo fee includes water, trash, grounds maintenance, the community pool and clubhouse.

713 Rapidan River Court Unit G, South 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, Central Chesapeake

1809 Hearthside Court, Central 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, Central 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, Central Chesapeake

$289,900

2 Beds ⋅ 1.1 Baths ⋅ 10655553 MLS

Welcome to this beautifully refreshed 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in sought-after Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace and an inviting floor plan perfect for relaxing or entertaining. Recent updates include fresh paint, new flooring and carpet, updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry full bath, and large hall closet for extra storage. Enjoy a private fenced backyard and new deck, perfect for morning coffee, grilling, or unwinding. Conveniently located near shopping, dining, parks, interstates, Chesapeake City Hall, and Grassfield schools. Move-in ready and waiting for its new owner!

300 San Roman Drive, South 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, Central Chesapeake

$199,900

3 Beds ⋅ 1 Baths ⋅ 10655489 MLS

Rare package deal opportunity in highly sought-after Western Branch! This move-in ready 3-bedroom ranch sits on a quiet street. The home has new paint, new floors, new A/C & heat systems, new wrap around porch, newer appliances and windows. The large rear yard and side lot provide an abundance of space for storing an RV, boat, or multiple extra cars. Nestled in a quiet neighborhood just minutes from local shopping, parks, schools, and military bases. No HOA. Additional lot next door can be purchased as well at 4999 Clifton St.

5001 Clifton Street, West Chesapeake

1321 Seaboard Avenue, Central 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, Central Chesapeake

605 Wingfield Avenue, Central 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, Central Chesapeake

601 Wingfield Avenue, Central 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, Central Chesapeake

$230,000

2 Beds ⋅ 2.1 Baths ⋅ 10655183 MLS

Charming 2 bedroom 2.5 bath condominium near shopping, restaurants and Chesapeake Regional Hospital. Home has all new LVP flooring and fresh paint. Brand new light fixtures and ceiling fans. Seller willing to give appliance allowance with acceptable offer.

618 Ridge Circle, 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.