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 in the heart of Chesapeake County, this delightful city is renowned for its friendly neighborhoods, lush parks, and a strong sense of community. With its convenient access to major highways, South Chesapeake offers an ideal location for commuters while providing a peaceful retreat from the hustle and bustle of city life.

One of the most appealing aspects of South Chesapeake is its diverse housing market, particularly for those seeking homes under $300,000. Here, you’ll find a variety of options that cater to first-time homebuyers, growing families, and retirees alike. From quaint single-family homes with spacious backyards to modern townhouses in vibrant communities, South Chesapeake has something for everyone.

The affordability of homes in this area allows residents to enjoy a comfortable lifestyle without breaking the bank. Imagine hosting family gatherings in your backyard, exploring the nearby parks, or taking leisurely strolls through the picturesque neighborhoods. Plus, with excellent schools, shopping centers, and recreational facilities just around the corner, everything you need is within reach.

Whether you’re looking to invest in your first home or downsize to a cozier space, South Chesapeake offers a welcoming environment that truly feels like home. Come explore the possibilities and discover why so many people are choosing to put down roots in this charming city. Your dream home awaits in South Chesapeake!

Newest South Chesapeake 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 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 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

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

540 Fernwood Farms Road, South Chesapeake

$99,000

2 Beds ⋅ 1 Baths ⋅ 10656859 MLS

Total assessed value $237,400, lot dimensions 170x265, 1 acre, 2/1 bath 740 sq ft.

540 Fernwood Farms Road, South Chesapeake

$299,900

3 Beds ⋅ 2 Baths ⋅ 10656850 MLS

Completely transformed from top to bottom, this stunning ranch offers an exceptionally open floor plan and extensive updates inside and out! The foyer, living room, dining room, and kitchen flow seamlessly together, creating an ideal space for everyday living and entertaining. The remodeled kitchen features new cabinetry, granite countertops, stainless steel appliances, updated lighting, and finishes. Both bathrooms are fully renovated, with new flooring/carpet, fresh paint, light fixtures, hardware and switches throughout. The oversized primary suite offers an impressive private retreat. Major updates include a new roof, windows, 200-amp electrical panel/service, upgraded electrical, and new kitchen/HVAC circuits. Outside, enjoy a new front door and sliding glass door leading to a huge backyard. The detached 2 car garage has a new garage door and offers space for vehicles, storage or a workshop. This home is truly move-in ready!

1311 Perry Street, South Chesapeake

$300,000

3 Beds ⋅ 2.1 Baths ⋅ 10656711 MLS

Welcome to 1528 Hambledon Loop, a desirable end-unit in Brighton Park at Greenbrier! This 3-bedroom, 2.5-bath home, 2 master bedrooms with ensuites offers a comfortable floor plan with the added privacy and natural light of an end-unit location. Recent updates include a NEW water heater, offering added peace of mind for the next homeowner. Enjoy the convenience of low-maintenance community living with access to neighborhood amenities, including 2 community pools. Ideally located in Chesapeake’s Greenbrier area, close to shopping, dining, entertainment and major roadways. Whether you're a first-time buyer, looking for additional space, or seeking a convenient Chesapeake location, this home is ready for its next owner. Schedule your showing today!

1528 Hambledon Loop, South Chesapeake

$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

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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.