South Chesapeake Homes under $300,000

Welcome to South Chesapeake, Virginia – a hidden gem that perfectly blends suburban charm with the vibrancy of modern living. Nestled within the picturesque landscapes of Chesapeake County, this delightful city offers a unique lifestyle that appeals to families, young professionals, and retirees alike. With its lush parks, friendly neighborhoods, and a strong sense of community, South Chesapeake is an ideal place to call home.

One of the standout features of South Chesapeake is its affordability. Here, you can find an array of charming homes priced under $300,000, making it an attractive option for first-time homebuyers or those looking to downsize without compromising on quality. These homes often boast spacious layouts, cozy yards, and convenient access to local amenities. Imagine settling into a lovely three-bedroom bungalow or a modern townhome, all while enjoying the peace and tranquility that South Chesapeake has to offer.

In addition to its beautiful homes, South Chesapeake is well-connected to major highways, providing easy access to nearby cities and attractions. Explore the local parks, enjoy a day at the Chesapeake Arboretum, or take advantage of the vibrant shopping and dining scene. With top-rated schools and a variety of recreational activities, this city truly has something for everyone.

Whether you're seeking your first home or looking to invest in a property that offers great value, South Chesapeake is the perfect destination. Discover your dream home today and experience the warmth and charm that this wonderful community has to offer!

Newest South Chesapeake Homes under $300,000

$225,000

3 Beds ⋅ 2 Baths ⋅ 10659764 MLS

Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. Properties must be purchased together, so bring your vision and schedule your showing today!

1672 Benefit Road, South Chesapeake

$235,500

2 Beds ⋅ 2 Baths ⋅ 10659589 MLS

Charming 2-bedroom, 2-bath condo offering a comfortable layout and great potential. The unit allows for great opportunity for cosmetic improvements to really make it your own. Conveniently located near dining, shopping, and more! Call today for more information and to schedule your tour!

501 Seahorse Run, South Chesapeake

847 Sommerville Crescent, South Chesapeake

$280,000

2 Beds ⋅ 2.1 Baths ⋅ 10659671 MLS

NEWLY RENOVATED BRICK FRONT TOWNHOUSE. 2 ENSUITE BEDROOMS, EACH WITH THEIR OWN BATHROOM. MOVE-IN READY. COMPLETLY RENOVATED KITCHEN, BRAND NEW CABINETS AND APPLIANCES, FRESH PAINT, INSTALLED 5 NEW GFCI OUTLETS TO MEET CURRENT ELECTRICAL SAFETY CODE, AND MORE... CENTRALLY LOCATED NEAR INTERSTATES, CHESAPEAKE GENERAL HOSPITAL, SCHOOLS AND SHOPPING CENTERS, AND NO HOA FEES!

847 Sommerville Crescent, South Chesapeake

321 Wimbledon Chase Unit E, South Chesapeake

$225,000

2 Beds ⋅ 2 Baths ⋅ 10659315 MLS

This 2 bedroom, single story, first floor condo unit is ready for you! Centrally located and nearby to Chesapeake Regional Medical Center, shopping, parks and schools. Schedule your showing today!

321 Wimbledon Chase Unit E, South Chesapeake

$295,000

2 Beds ⋅ 2.1 Baths ⋅ 10659342 MLS

Do not miss out on this lovely home that features two spacious bedrooms on the First floor, each with its own private bath! There is also a third floor flex room that overlooks the 2nd level great room with balcony! The 2nd level supports open-concept living filled with natural light, highlighted by soaring vaulted ceilings and an electric fireplace that creates the most amazing gathering space. Residents also have access to outstanding community amenities, including a swimming pool, tennis courts, and a playground. This condo could be the amazing home for you if you are looking for a low-maintenance lifestyle in a peaceful setting, do not miss out, schedule a viewing today!

577 Seahorse Run, South Chesapeake

$299,000

3 Beds ⋅ 2.1 Baths ⋅ 10659243 MLS

Fresh, bright and move-in ready! Welcome home to 720 Hunters Quay, a charming 3 bedroom, 2.5 bath brick-front townhome for sale in Chesapeake, VA with no HOA and nothing left to do but unpack. Out front, a classic brick facade, a welcoming front stoop and tidy landscaping deliver instant curb appeal. Inside, fresh neutral paint and durable luxury vinyl plank (LVP) flooring flow through the main level, giving this home a clean, modern feel you will love from the very first step. The updated kitchen is ready for anything, with crisp white shaker-style cabinets, sparkling granite countertops, a handy pantry and a full appliance package including the refrigerator, range, microwave and dishwasher. Host dinner in the separate dining room with chair-rail trim and a stylish chandelier, then gather around the wood-burning fireplace in the living room on cool Virginia evenings. Sliding glass doors open to a private, fully fenced backyard with a patio, made for grilling, gardening, morning coffee and room for pets to play. Upstairs, the spacious primary suite shines with a vaulted ceiling, ceiling fan, walk-in closet and its own private full bath with a granite vanity. Two more generous bedrooms with ceiling fans offer flexible space for guests, a home office, a gym or hobbies, and the hall bath features a fresh granite vanity too. A convenient main-level half bath, central air, natural gas heat and two off-street parking spaces plus street parking make everyday living easy. Tucked into the Hunters Glen community, you are just minutes from Oak Grove Lake Park, Greenbrier and Great Bridge shopping and dining, and quick commuter routes to I-64 and I-464. Updated townhomes at this price go fast in Chesapeake, so come see it today!

720 Hunters Quay, South Chesapeake

1540 Eldwick Drive #206, South Chesapeake

$295,130

2 Beds ⋅ 2 Baths ⋅ 10659134 MLS

Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #206, South Chesapeake

1717 Stoney Creek Arch Unit B, South Chesapeake

$220,000

2 Beds ⋅ 2 Baths ⋅ 10659009 MLS

This 2 bedroom, 2 bath first floor condo is move-in ready with new carpet and paint in Oct. 2026. The great room has a fireplace with mantle and the kitchen has granite counter tops and Stainless Steel Appliances. It is in a very convenient location near Greenbrier Mall.

1717 Stoney Creek Arch Unit B, South Chesapeake

322 Gainsborough Square, South Chesapeake

$219,900

2 Beds ⋅ 2 Baths ⋅ 10658922 MLS

Two-bedroom, two-bathroom condo in desirable Wimbledon Chase. The fenced front porch offers a welcoming outdoor space to relax and enjoy. Inside, the inviting floor plan features cathedral ceilings and abundant natural light, creating a bright, open feel throughout the spacious living room, dining area, and kitchen. The primary suite offers a walk-in closet and ensuite bath, while the second bedroom provides comfortable additional space. Enjoy the convenience of low-maintenance living, with dining, shopping, and more nearby.

322 Gainsborough Square, South Chesapeake

516 Willow Green Court, South Chesapeake

$225,000

2 Beds ⋅ 2.1 Baths ⋅ 10658629 MLS

Located in the Riverwalk community of Chesapeake, this 2-bedroom, 2.5-bath condo offers a comfortable and functional layout designed for everyday living. Recent updates include new windows, new kitchen appliances, and a new sliding glass door that opens to the back patio, providing a nice space to relax. Conveniently located near shopping, dining, and major roadways, this home combines the convenience of condo living with a wonderful place to call your own. Welcome home!

516 Willow Green Court, South Chesapeake

$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

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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.

South Chesapeake Homes under $300,000

Newest South Chesapeake Homes under $300,000

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