Chesapeake VA County Homes under $300,000

Welcome to Chesapeake, Virginia – a hidden gem nestled in the heart of Hampton Roads! Known for its picturesque landscapes, vibrant communities, and rich history, Chesapeake offers a unique blend of suburban charm and urban convenience. With sprawling parks, serene waterways, and an abundance of outdoor activities, residents enjoy a lifestyle that embraces both relaxation and adventure.

For those seeking affordable housing options, Chesapeake is a fantastic place to call home. The real estate market features a variety of homes priced under $300,000, making it an ideal choice for first-time buyers, families, or anyone looking to invest in a thriving community. From cozy single-family homes to townhouses with modern amenities, there’s something for everyone within this budget. Many of these homes are situated in family-friendly neighborhoods, ensuring a welcoming environment for all.

Chesapeake boasts excellent schools, a strong sense of community, and easy access to major highways, making commuting a breeze. You’ll find a rich tapestry of shopping, dining, and entertainment options nearby, ensuring that there’s never a dull moment. Whether you’re exploring the scenic Great Dismal Swamp National Wildlife Refuge or enjoying a day at one of the local parks, Chesapeake offers countless opportunities to create lasting memories.

Don’t miss out on the chance to find your dream home in this beautiful city. With homes under $300,000, Chesapeake is not just a place to live; it’s a place to thrive! Explore your options today and discover all that this vibrant community has to offer.

Newest Chesapeake VA County Homes under $300,000

$260,000

3 Beds ⋅ 1.1 Baths ⋅ 10657685 MLS

Welcome to 1021 Roundtable Court! This beautifully renovated, move-in-ready Chesapeake home offers modern upgrades, stylish finishes and exceptional convenience! Enjoy fresh interior paint, updated flooring, new lighting, updated trim and new blinds throughout. The refreshed kitchen features brand-new stainless steel appliances, including a refrigerator, electric range, microwave, and garbage disposal. Both bathrooms feature updated vanities, faucets, and fixtures. Additional improvements include new interior and exterior doors, storm doors, updated vinyl siding, exterior trim, and a replacement window. Enjoy modern technology with a smart ceiling fan that operates by remote or through a Wi-Fi-connected app. The washer and dryer also convey, making your move even easier! The roof and HVAC system were replaced approximately 10 years ago. With extensive interior and exterior improvements, this home offers the comfort, style, and convenience today’s buyers appreciate. This one is a gem - you don't want to miss out! Schedule your showing today!

1021 Roundtable Court, South Chesapeake

1514 Orchard Grove Drive, South Chesapeake

$269,900

3 Beds ⋅ 2 Baths ⋅ 10657524 MLS

Welcome home to Orchard Grove Condominiums in Chesapeake! This spacious 2-bedroom, 2-bathroom condo offers a flexible floor plan with plenty of room to relax, entertain, work from home, and unwind, plus access to a community pool. Step inside to a bright and inviting living area, where a vaulted ceiling, fireplace, and abundant natural light create a welcoming place to gather or relax. The open layout flows into the dining area and kitchen, featuring generous cabinet and counter space, a full appliance package, and a breakfast bar for casual dining. The downstairs primary suite offers the convenience of main-level living with an ensuite bath featuring a soaking tub and separate shower. Upstairs, a second bedroom with its own full ensuite bath provides another private retreat. The open loft adds even more flexibility as a home office, reading nook, media area, or additional guest space. The enclosed sunroom offers another inviting bonus space, perfect for morning coffee, plants, reading, or simply relaxing. Additional storage adds everyday convenience. Located in Greenbrier, the home is conveniently situated near shopping, dining, Greenbrier Mall, and major highways, providing easy access throughout Chesapeake and Hampton Roads. Residents can also enjoy the Orchard Grove community pool. There is a lot to love about this home. Do not miss the opportunity to make this Orchard Grove condo your own!

1514 Orchard Grove Drive, South Chesapeake

$255,000

2 Beds ⋅ 1 Baths ⋅ 10657509 MLS

2BD, 1 BA ONE STORY TOWNHOME. ALL KITCHEN APPLIANCES, LARGE LIVING ROOM OPENS TO KITCHEN, FENCED IN YARD LOCATED IN A CULDESAC. EXCELLENT HOME FOR FIRST TIME HOME BUYER OR INVESTOR.

1054 Wickford Court, South Chesapeake

401 Henley Court Unit K, South Chesapeake

$229,900

2 Beds ⋅ 2.1 Baths ⋅ 10657298 MLS

Affordable living in the largest condo model available in Wimbledon Chase. Easy access to I64, the Chesapeake Expressway, Greenbrier and Great Bridge. No car needed for access to shopping & restaurants; adjacent to Chesapeake Regional Medical Complex. Summertime living is easy with the community pool. All appliances convey including washer & dryer, as-is.Besides the generous ensuite, the primary bedroom features a cathedral ceiling and more closet space than many single family homes. Condo fees cover the master insurance policy, landscaping, water, trash, sewer, pool access, as well as exterior building maintenance. $2,000 carpet allowance on full price contract.

401 Henley Court Unit K, South Chesapeake

2901 Bainbridge Boulevard, Central Chesapeake

$300,000

3 Beds ⋅ 1 Baths ⋅ 10657210 MLS

Fall in love with this freshly renovated gem in the heart of Chesapeake! Featuring 3 bedrooms and 1 full bath, this charming home welcomes you with gorgeous hardwood floors, freshly painted interiors, and an abundance of natural light. The bright kitchen offers granite countertops, stainless steel appliances, and a cozy breakfast area. Thoughtful details, including built-in cabinetry and ample storage, add both character and functionality. Step outside to enjoy the screened-in porch and wood privacy-fenced backyard, great for entertaining guests or simply unwinding. New HVAC. Complete with a spacious 2-car garage and situated on a corner lot, this home offers comfort and convenience with easy access to I-464 and the Jordan Bridge. Don't miss the opportunity to make this beautiful property your own!

2901 Bainbridge Boulevard, Central Chesapeake

500 Judah Way Unit 123, South Chesapeake

$270,000

2 Beds ⋅ 2 Baths ⋅ 10656973 MLS

Tucked away in a private, gated enclave, this bright and modern condo offers peaceful, low-maintenance living with controlled entry and security! Elevator access to the 2nd floor. This unit has an open and spacious floor plan, updated kitchen, dining area, family room, two new balconies with two primary suites. Private first-floor storage room plus two reserved parking spaces. Condo fees include Fitness Center, Gathering Room with outdoor grill area, security, grounds maintenance and trash pickup. Private yet convenient in Greenbrier near Chesapeake City Park, shopping, dining and interstates. Schedule your private showing today!

500 Judah Way Unit 123, South Chesapeake

$299,900

3 Beds ⋅ 1 Baths ⋅ 10657145 MLS

Welcome home to this beautiful, move-in-ready ranch style property in Chesapeake! Featuring a bright and airy openconcept floor plan, this home offers an effortless flow is great for entertaining. The interior boasts 3 bedrooms, 1 full bath and tasteful modern updates throughout. Outside, your private outdoor retreat awaits, complete with a newer deck that leads to a generously sized backyard, fully enclosed by a privacy fence. Wrapped in newer, low-maintenance vinyl, this home combines classic appeal with easy upkeep. Conveniently located with quick access to local military bases, premier shopping, dining, and major interstates for an easy commute.

1313 Willow Avenue, Central Chesapeake

1940 Candlelight Drive, Central Chesapeake

$240,000

2 Beds ⋅ 2.1 Baths ⋅ 10657007 MLS

Opportunity awaits in Georgetown Colony! This 2-bedroom, 2.5-bath townhouse is ready for a little TLC and offers a great chance to build equity and make it your own. The home features new carpet upstairs, a functional layout, and plenty of potential for updates and personal touches. Conveniently located in Chesapeake with easy access to shopping, dining, major roadways, and everyday amenities. Whether you're looking for an investment property or a home to make your own, this one is worth a look!

1940 Candlelight Drive, Central Chesapeake

$290,000

3 Beds ⋅ 1 Baths ⋅ 10656626 MLS

A large detached garage with high ceilings and power sets this 3-bedroom, 1-bath home apart! Offering exceptional flexibility for parking, storage, a workshop, hobbies, or additional workspace, the garage is a standout feature you won’t want to miss. Inside, the kitchen featuring a double oven flows seamlessly into the living room, creating an inviting open layout that works well for everyday living and entertaining. The kitchen also has a separate gas cooktop and a functional design with great potential. Outside, enjoy the backyard deck, great for relaxing, grilling, or entertaining. With a combination of a spacious detached garage, open living area, gas cooking, and outdoor living space, this home offers features that make it stand out. Come see all this property has to offer and how close it is to key areas of Norfolk, Chesapeake, and Va. Beach!

3004 Kilbride Drive, Central Chesapeake

$289,900

2 Beds ⋅ 2.1 Baths ⋅ 10657099 MLS

Welcome to this spacious townhouse in Chesapeake in a great locationwith NO HOA!! The bright kitchen features a butler's window to provide a convenient pass-through for serving between the kitchen and dining area. The living room opens from the dining room and features a wood-burning fireplace as a centerpiece. Sliding glass doors lead from the living room to the back patio and fenced yard. Upstairs, you'll find two large bedrooms, each with its own ensuite bathroom and plenty of closet space. The primary bedroom also features a second wood-burning fireplace, creating a comfortable space to relax. Conveniently located near shopping, dining, schools, and major roadways.

708 Nottaway Drive, South Chesapeake

3616 Clover Meadows Drive, West Chesapeake

$155,000

2 Beds ⋅ 1 Baths ⋅ 10657048 MLS

Welcome home to this quiet end-unit condo in the heart of Western Branch! This property includes beautiful luxury vinyl plank flooring, a newer washer and drier, and a fully equipped kitchen with gorgeous cabinets and granite countertops. Condo fees cover trash, ground maintenance, landscaping, exterior siding and more! Easily accessible to all military bases & move-in ready! Don't miss this one, schedule your showing today and make this home yours!

3616 Clover Meadows Drive, West Chesapeake

701 New River Court Unit B, South Chesapeake

$235,000

2 Beds ⋅ 2 Baths ⋅ 10657033 MLS

Honey stop the car! Townhouse-style living w/condo convenience in Chesapeake's Riverwalk community! This 2 bedroom, 2 full bath home offers approximately 1,100 sq ft across two levels, giving you the feel of a townhome without the upkeep. Fresh paint and new LVP flooring run throughout, so it's truly move-in ready. One of the two full baths has been remodeled. The main level is built for everyday living, with a fireplace in the living room and access to a private patio for morning coffee or quiet evenings. An exterior storage room adds space for bikes, tools and seasonal gear. The condo fee covers water, sewer, trash, grounds and exterior maintenance, plus access to the community pool and clubhouse. Convenient to Greenbrier shopping, dining and medical facilities, with easy access to I-64, local military installations CALL TODAY!

701 New River Court Unit B, 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.