Chesapeake VA County Homes under $300,000

Welcome to Chesapeake, Virginia—where Southern charm meets modern convenience! Nestled in the heart of Hampton Roads, Chesapeake is a vibrant city known for its rich history, scenic landscapes, and a welcoming community. With its beautiful parks, extensive waterways, and diverse recreational opportunities, Chesapeake offers a perfect blend of urban living and outdoor adventures.

For those seeking affordable housing options, Chesapeake boasts a variety of homes under $300,000, making it an ideal destination for first-time homebuyers, families, and investors alike. You'll find charming single-family homes, cozy townhouses, and inviting condos that provide excellent value without compromising on quality. Each neighborhood has its unique character, from the bustling areas near shopping and dining to the serene pockets that offer tranquility and nature.

Imagine living just minutes from the stunning Elizabeth River, where you can enjoy kayaking, fishing, or simply taking a peaceful stroll along the waterfront. The city's strong sense of community is reflected in its local events, farmers' markets, and festivals that bring residents together year-round.

With top-rated schools, convenient access to major highways, and proximity to military bases, Chesapeake is not just a place to live—it's a place to thrive. Explore the possibilities of homeownership in this enchanting city, where your dream home awaits at an affordable price. Come experience the warmth of Chesapeake, where your new chapter begins!

Newest Chesapeake VA County Homes under $300,000

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

$220,000

2 Beds ⋅ 1 Baths ⋅ 10655259 MLS

Welcome to this cozy 2 bedroom, 1 bathroom ranch home located in the heart of Deep Creek! This home offers a comfortable layout, an attached 1-car garage, and a spacious backyard with a privacy fence, providing plenty of room for outdoor enjoyment. The large detached shed/workshop offers additional storage and space for hobbies or projects. With its charming touches, great outdoor space, and convenient location near shopping, dining, and major roadways, this home is ready for its next owner to make it their own!

2704 George Dr Drive, South 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.