Chesapeake VA County Homes under $500,000

Chesapeake VA County Homes under $500,000

Welcome to Chesapeake, Virginia – a picturesque city that beautifully blends suburban charm with vibrant urban amenities. Nestled in the heart of Hampton Roads, Chesapeake boasts a rich tapestry of history, culture, and natural beauty. With its scenic parks, extensive waterways, and family-friendly neighborhoods, it’s no wonder that this delightful city is a sought-after destination for homebuyers.

Chesapeake is renowned for its strong sense of community and commitment to quality living. The city offers an array of recreational activities, from hiking and biking along the scenic Dismal Swamp Canal to enjoying a day at the stunning Chesapeake City Park. Plus, with its proximity to the bustling cities of Norfolk and Virginia Beach, residents can easily access a variety of shopping, dining, and entertainment options.

For those looking to settle down in this charming locale, there’s great news! Chesapeake offers a diverse selection of homes priced under $500,000, making it an attractive option for first-time buyers, growing families, and retirees alike. From cozy single-family homes in family-friendly neighborhoods to modern townhouses with contemporary finishes, there’s something for everyone.

With a range of schools, parks, and community resources, Chesapeake is not just a place to live; it’s a place to thrive. Explore your options today and discover the perfect home that fits your lifestyle and budget in this vibrant Virginia gem! Whether you’re looking for a peaceful retreat or a lively community, Chesapeake has it all waiting for you.

Newest Chesapeake VA County Homes under $500,000

1432 Scoonie Pointe Drive, South Chesapeake
$449,900
3 Beds ⋅ 2 Baths ⋅ 10658513 MLS
Welcome to 1432 Scoonie Pointe Drive in Chesapeake! Enjoy comfortable, low-maintenance living in this desirable 55+ community. This inviting home features an open floor plan, cathedral ceilings, and convenient one-level living. Handicap-accessible features add comfort and ease, while the sunroom provides the perfect spot to relax, enjoy your morning coffee, or entertain guests. Residents can take advantage of wonderful community amenities, including a swimming pool and clubhouse. With ground maintenance included, you can spend more time enjoying life and less time worrying about upkeep. Conveniently located near shopping, restaurants, and everyday essentials, this home offers a wonderful combination of comfort, convenience, and community living. If you're looking to simplify your lifestyle without sacrificing comfort or amenities, this home is a must-see! Please verify the community's 55+ age requirements and 80/20 homeowner eligibility guidelines.

1432 Scoonie Pointe Drive, South Chesapeake
1325 Debbs Lane, South Chesapeake
$420,000
4 Beds ⋅ 2.1 Baths ⋅ 10658609 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the heart of Chesapeake's Greenbrier area. Enjoy fresh paint, new LVP flooring, and new carpet throughout. The spacious, open floor plain is great for entertaining, hosting gatherings, and everyday living. The generous kitchen features granite countertops and stainless-steel appliances, making meal preparation a pleasure. Head outdoors to your large paver patio and enjoy the privacy of a fenced backyard, desirable for relaxing or entertaining outdoors. The attached garage offers added convenience with a new garage door opener. Centrally located near military bases, beaches, medical facilities, shopping, restaurants, and major interstates, this home combines modern updates, comfortable living, and a convenient location! Don't miss the opportunity to make this wonderful home yours!

1325 Debbs Lane, South Chesapeake
2304 Swinson Landing, South Chesapeake
$430,000
4 Beds ⋅ 2 Baths ⋅ 10658594 MLS
Welcome to 2304 Swinson Landing! Tucked away on a cul-de-sac with no HOA, this charming 4-bedroom, 2-bath ranch offers approximately 1,800 square feet of comfortable living space and a peaceful wooded backdrop. Inside, you'll find a bright, inviting kitchen featuring a beautiful bay window overlooking the backyard, bringing the outdoors right into your everyday routine. Enjoy slow mornings with coffee on the screened-in porch, host friends on the spacious back deck, or simply unwind while taking in the wooded views. The versatile finished room over the garage (FROG) provides additional space to fit your needs, along with plenty of storage. An attached garage offers even more room for parking, hobbies, or organization. With a roof, HVAC system, and appliances updated in 2017, this home combines practical features with inviting spaces to enjoy. Conveniently located in Chesapeake, this is one you won't want to miss!

2304 Swinson Landing, South Chesapeake
2213 Wildwood Road, South Chesapeake
$418,899
4 Beds ⋅ 2 Baths ⋅ 10658565 MLS
Charming brick home with plenty of character, versatile living spaces, and a backyard made for entertaining! Offering 4 bedrooms and 2 full baths, this home features hardwood floors, a cozy gas fireplace, and a first-floor bedroom for added flexibility. The upper level provides additional bedrooms with their own unique character. Enjoy outdoor living on the screened porch or deck overlooking the fenced backyard and in-ground swimming pool. A detached brick building with its own kitchenette and full bathroom offers additional possibilities for a hobby space, workshop, or poolside entertaining. Situated on approximately a quarter-acre lot with no HOA, this property offers a wonderful combination of indoor and outdoor space, distinctive features, and the opportunity to make it your own! Opportunity for up to $3500 lender credit with use of preferred lender.

2213 Wildwood Road, South Chesapeake
822 Wickford Drive, South Chesapeake
$258,500
3 Beds ⋅ 2 Baths ⋅ 10658490 MLS
Stop and look at this Beautiful Townhome located in the Heart of Chesapeake. Roof less than 5 years old!!!, Updated interior, Granite Counters Tops, Spacious Vaulted Great Room opens to the Kitchen. Premium Laminate Wood Floors, 2nd Floor Master w/Bath. Priced to sell! Call today to schedule to view before this Great Home is SOLD!

822 Wickford Drive, South Chesapeake
1013 Mckinley Avenue, Central Chesapeake
$349,900
10658545 MLS
Desirable side-by-side, all brick duplex in Chesapeake! Both units are mirror images with move-in ready finishes! Featuring NO carpet, wood flooring throughout in unit A & LVP throughout in unit B, upgraded kitchens with shaker cabinetry, as well as modern appliances! Both units have laundry hookups. Two great-sized bedrooms with ample closet space. Hall bath with designated linen closet inside and in the hall as well. Water and electric are both sepertely metered. Roof 2022, water heaters 2023! Solid rental history for both units. Unit A is rented at $1495 per month until 3/31/27. Unit B is currently vacant, making this is a great opportunity for investors, as well as owner-occupants alike! Call today!

1013 Mckinley Avenue, Central Chesapeake
303 Diamond Avenue, South Chesapeake
$350,000
3 Beds ⋅ 2 Baths ⋅ 10658571 MLS
Welcome to this beautifully updated 3-bedroom, 2-bathroom home located in a sought-after Chesapeake neighborhood! Offering peace of mind and modern comfort, this home features a brand-new roof, siding, HVAC system, water heater, and windows—giving you the major updates you want without the worry of costly replacements.Inside, you’ll find a comfortable and inviting layout with plenty of natural light and space for everyday living and entertaining. The spacious bedrooms and two full bathrooms provide flexibility.Situated in a desirable Chesapeake location close to shopping, dining, schools, parks, and major roadways, this move-in-ready home is an excellent opportunity for buyers looking for convenience, updates, and value. Don’t miss your chance to make this beautifully refreshed home yours!

303 Diamond Avenue, South Chesapeake
306 Holly Glen Drive, Central Chesapeake
$392,000
4 Beds ⋅ 2.1 Baths ⋅ 10658566 MLS
MAKE THIS HOUSE YOUR NEXT HOME! SPACIOUS TWO STORY HOME WITH VERSATILE FLOOR PLAN DESIGNED TO ACCOMMODATE A VARIETY OF LIFESTLYES. 3 BEDROOMS UPSTAIRS AND 1 BEDROOM DOWNSTAIRS. CERAMIC TILE THROUGHOUT DOWNSTAIRS. MASSIVE CATHERDRAL CEILING IN MAIN LIVING AREA. FENCED IN BACKYARD PERFECT FOR OUTDOOR RELAXATION AND ENTERTAINING. FRONT YARD AND ANYTHING OUTSIDE OF FENCING IS CUT AND TRIMMED AND TAKEN CARE OF FOR YOU.

306 Holly Glen Drive, Central Chesapeake
518 Eldridge Lane, South Chesapeake
$469,900
3 Beds ⋅ 2.1 Baths ⋅ 10658549 MLS
Built in 2023, this modern home has it all. From the 2-story foyer, the great room awaits with cathedral ceilings and abundant natural light. The kitchen features quartz countertops, stainless energy-efficient appliances, 42-inch cabinets, and modern black fixtures. Just off the kitchen, you'll find the half bath and mudroom/ laundroom leading to the attached 2-car garage, complete with epoxy floors and storage racks. A prime first-floor primary suite features tray ceilings, a dual-vanity bath, a tiled shower, and a walk-in closet. Upstairs, you will find a versatile loft, open to the living room below, a full bath, and two additional bedrooms, each with its own walk-in closet. Enjoy top-tier community amenities including a pavilion, splash pad, dog park, playground, and walking trails, all conveniently located near Cahoon Parkway, schools, shopping, and major interstates for an easy commute.

518 Eldridge Lane, South Chesapeake
2168 Armada Drive E, West Chesapeake
$379,000
3 Beds ⋅ 1.1 Baths ⋅ 10658509 MLS
ASSUMABLE 3.625% FHA LOAN! Charming Brick Ranch in the Heart of West Chesapeake! This adorable 3-bedroom 1.5 bath ranch-style home sits on a spacious .39-acre lot and is move-in ready! BUYERS MAY ALSO BE ABLE TO ASSUME THE SELLER’S FHA LOAN AT A LOW 3.625% RATE-A RARE OPPORTUNITY FOR QUALIFIED BUYERS IN TODAY’S MARKET. A Enjoy a freshly painted interior, new flooring & more. The home features a formal living room and dining room, a cozy wood burning fireplace. Additional highlights a detached oversized garage- great for a workshop, extra storage, or hobby’s space. Located in the established Chadswyck Terrace West neighborhood with easy access to shopping, dining, and major routes. No HOA! Don’t miss this gem-schedule your showing today! Some photos have been virtually staged to showcase the home’s potential.

2168 Armada Drive E, West Chesapeake
3057 Kenelm Drive, South Chesapeake
$329,900
3 Beds ⋅ 1.1 Baths ⋅ 10658506 MLS
Welcome home to this inviting 3-bedroom, 1.5-bath ranch nestled in an established neighborhood! This home offers a functional layout and features designed for comfortable everyday living. The eat-in kitchen boasts stainless steel appliances, ample cabinetry, and plenty of counter space. Enjoy the spacious backyard with a privacy fence. Additional features include architectural roof shingles, updated windows, a heat pump HVAC system, a newer electric water heater, and off-street parking. The seller is inspecting the roof and complete any necessary repairs or replacement. Some photos have been virtually staged. Don’t miss the opportunity to make this home your own!

3057 Kenelm Drive, South Chesapeake
1431 Oliver Avenue, Central Chesapeake
$375,000
4 Beds ⋅ 3 Baths ⋅ 10657417 MLS
Fall in love with this beautifully updated 4-bedroom, 3-full-bathroom home! New luxury vinyl plank flooring throughout the entire downstairs creates a fresh, stylish, low-maintenance space. The open kitchen features a breakfast bar and flows into the spacious living room, making everyday living and entertaining easy. Upstairs, new plush carpeting leads to four generously sized bedrooms, including an expansive primary ensuite with a large bedroom, spacious adjoining bathroom, and large walk-in closet. Three full bathrooms offer added comfort and convenience, and a newly installed HVAC system is another valuable update. Buyers may have the opportunity to assume the existing loan at an attractive 3.5% interest rate, subject to lender approval, eligibility, and assumption terms. With modern updates, spacious gathering areas, and a flexible floor plan, this home offers comfort, practicality, and room to grow. Schedule your showing and discover all this home has to offer!

1431 Oliver Avenue, Central 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.

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