South Chesapeake Homes under $300,000

Welcome to South Chesapeake, Virginia—a hidden gem nestled in the heart of Chesapeake County. This vibrant community offers a perfect blend of suburban charm and urban convenience, making it an ideal place for families, young professionals, and retirees alike. With its lush parks, friendly neighborhoods, and a strong sense of community, South Chesapeake is a place where everyone can feel at home.

One of the most appealing aspects of South Chesapeake is its affordability. For those seeking to buy a home without breaking the bank, this area features a variety of options under $300,000. Whether you're looking for a cozy starter home, a spacious townhouse, or a charming single-family residence, you’ll find a diverse selection that caters to every lifestyle and budget. These homes often come with modern amenities, inviting yards, and easy access to local schools and shopping centers.

Living in South Chesapeake means enjoying a wealth of recreational opportunities. With numerous parks, walking trails, and community events, residents can embrace an active lifestyle while fostering connections with their neighbors. The city is also conveniently located near major highways, providing easy access to the bustling cities of Norfolk and Virginia Beach, where you can explore a vibrant dining scene, cultural attractions, and beautiful waterfronts.

In South Chesapeake, you’ll discover a community that values both comfort and convenience, making it the perfect place to plant your roots. Come explore the affordable housing options and experience the warmth of Southern hospitality in this delightful Virginia city!

Newest South Chesapeake Homes under $300,000

710 Battlefield Boulevard Unit A, South Chesapeake

$299,900

3 Beds ⋅ 2 Baths ⋅ 10658043 MLS

710 Battlefield Boulevard Unit A, South Chesapeake

$262,500

2 Beds ⋅ 1 Baths ⋅ 10657727 MLS

Big backyard. Beautiful updates. Small price tag! Who says homeownership has to break the bank? Welcome to this charming 2 bedroom, 1 bath home in Loxley Gardens, offering the opportunity to own a move in ready home for under $300K! Enjoy a cute kitchen with brand new appliances, new flooring, a new roof, and new siding. The real showstopper? A MASSIVE backyard with endless possibilities for entertaining, pets, gardening, or creating your own outdoor oasis. Whether you're a first time buyer or looking to downsize, this one checks the boxes! Schedule your private tour today!

2432 Youngman Road, South 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

2112 Willow Point Arch, South Chesapeake

$240,000

2 Beds ⋅ 2 Baths ⋅ 10657769 MLS

Move-in ready 2-bedroom, 2-bath condo with spacious loft in the sought-after Riverwalk community! Freshly painted throughout with a new water heater and HVAC replaced in 2018. Bright, open floor plan features a kitchen overlooking the dining and living areas, creating a comfortable space for everyday living and entertaining. Generous first-floor bedroom offers a walk-in closet and direct access to a full bathroom. Upstairs features a versatile loft with built-ins and a spacious primary suite with ample closet space and private bath. Enjoy your own fenced front patio and additional storage shed. Conveniently located near shopping, restaurants, major highways, and military installations throughout Hampton Roads. Low-maintenance living, thoughtful updates, and an excellent location make this condo a fantastic opportunity. Schedule your showing now.

2112 Willow Point Arch, South Chesapeake

$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

2 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 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

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

$289,900

2 Beds ⋅ 2.1 Baths ⋅ 10657099 MLS

Welcome to this spacious townhouse in Chesapeake in a great location with 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. Property updates include a new tank water heater (2022), downstairs flooring (2022), fresh carpet and paint (2026), updated kitchen and bathroom faucets (2026), and a new backyard fence (2026). Water heater warranty may convey.

708 Nottaway Drive, South 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

$225,000

3 Beds ⋅ 1.1 Baths ⋅ 10657002 MLS

733 Wickford 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.