Chesapeake VA County Homes under $750,000

Welcome to Chesapeake, Virginia – a vibrant city that beautifully blends suburban charm with the rich history and natural beauty of coastal living. Nestled in the heart of Hampton Roads, Chesapeake boasts a diverse array of neighborhoods, each offering its unique character and appeal. With its lush parks, scenic waterways, and friendly communities, Chesapeake is an ideal place for families, retirees, and anyone looking to experience the best of Virginia living.

For those seeking a new home in this picturesque county, you’ll be delighted to discover a variety of options under $750,000. Whether you’re drawn to spacious single-family homes with sprawling backyards, modern townhouses with contemporary finishes, or charming bungalows with historic flair, Chesapeake has something for everyone. The real estate market here is thriving, with homes that cater to diverse lifestyles and budgets.

Imagine enjoying weekends exploring the Great Dismal Swamp National Wildlife Refuge or spending sunny afternoons at the Chesapeake City Park. With excellent schools, a robust economy, and a plethora of shopping and dining options, this city is not just a place to live; it’s a place to thrive.

Don’t miss out on the opportunity to find your dream home in this welcoming community. With homes available under $750,000, the perfect Chesapeake residence awaits you. Let us help you embark on this exciting journey to homeownership in one of Virginia’s most desirable locales!

Newest Chesapeake VA County Homes under $750,000

$585,740

3 Beds ⋅ 3 Baths ⋅ 10656534 MLS

Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2224 Edwin Drive, South Chesapeake

$585,740

3 Beds ⋅ 3 Baths ⋅ 10656532 MLS

2222 Edwin Drive, South Chesapeake

1149 Crystalwood Circle, South Chesapeake

$525,000

4 Beds ⋅ 2.1 Baths ⋅ 10656507 MLS

Welcome home to 1149 Crystalwood Circle! This inviting Chesapeake home has been thoughtfully cared for and updated over the years, offering the comfort of knowing many major improvements have already been completed. The electrical system was upgraded to 200-amp service in 2020, when the spacious 24' x 26' detached garage/workshop was added with its own 100-amp service. The HVAC received a new furnace and condenser in 2022, followed by a new washer and dryer in 2024 and a new water heater in 2025. In 2026, the home received a brand-new kitchen, new carpet, and a fully remediated crawl space with a new vapor barrier. With so much already done, there's more time to relax, enjoy your space, and make wonderful memories. Come see why this could be the one you've been waiting for!

1149 Crystalwood Circle, South Chesapeake

$594,800

5 Beds ⋅ 2.1 Baths ⋅ 10656498 MLS

Spacious and beautifully updated, this 2-story Chesapeake home offers 5 bedrooms, 2.5 bathrooms, and a versatile loft perfect for a home office, playroom, or media space. Situated on a desirable corner lot, enjoy outdoor living on the composite deck and added peace of mind with a backup generator. Conveniently located near shopping, parks, military bases, and major interstates, this home combines comfort, functionality, and an unbeatable location.

513 Telfyan Drive, South Chesapeake

$480,000

4 Beds ⋅ 2.1 Baths ⋅ 10656500 MLS

Beautiful Colonial-style home situated on a spacious 0.41 acre corner lot w/ deep water access, dock and bulkhead. This large yet cozy home offers 4 bedrooms and 2.5 bathrooms w/ blends of classic charm and comfy living. Enjoy family evenings by the fireplace and take advantage of the expansive backyard-perfect for entertaining, outdoor activities, or future enhancements. The large corner lot provides added privacy and curb appeal, while the storage shed and attached garage offers lots of extra space for tools and lawn equipment. A rare opportunity to own water front property w/ room to spread out, both inside and out right in the heart of the city. Close to shopping yet private for your family needs.

824 Heritage Point, South Chesapeake

$500,000

4 Beds ⋅ 3 Baths ⋅ 10656410 MLS

This is one of those rare homes that truly supports multi gen or other uses. TRUE DETACHED in law suite with kitchenette full LARGE bath, living and bedroom, private access. The roof, paint, carpet dishwasher ALL NEW to get ready to SELL ! Just a little personalization and this could be your dream home. Its just waiting for you. Full brick, masonry fireplace, oversized deck, extra driveway and a covered parking area. City and Zillow records not reflective of the current dwelling. Three generous bedrooms plus room over the garage AND the suite make this home a winner for you! DONT DRIVE? NO PROBLEM! VERY NEAR ALL ANCILLARY SERVICES Extra nice YMCA with indoor and outdoor pool just a few short blocks. Physicians, groceries, dining and the highway system.

229 Fresno Drive, South Chesapeake

$625,000

5 Beds ⋅ 2.1 Baths ⋅ 10656430 MLS

Welcome to the one that checks all the boxes- space, style, in the heart of Great Bridge location, and a backyard you definitely don’t find every day! Built in 2020, this updated 5-bedroom, 2.5-bath home offers approximately 2,200 square feet and sits on nearly .40 acres in the sought-after Great Bridge school district. While the home may only be a few years old, the current owners didn’t stop with builder finishes, nearly every space has been thoughtfully refreshed with updated paint, upgraded light fixtures, and carefully chosen details throughout. Truly, no room has been left untouched! Step inside to a bright, welcoming floor plan with spacious kitchen features, granite countertops, stainless steel appliances, plenty of cabinetry, and a large island, all opening into the family room with fireplace and a separate dining area. 5 bedrooms located upstairs as well as a dedicated laundry room and spacious primary suite that offers its own private retreat and walk-in closet.

233 Old Drive, South Chesapeake

$610,000

4 Beds ⋅ 2.1 Baths ⋅ 10656415 MLS

BUY THIS AWESOME HOME, WE’LL BUY YOURS!* Discover elevated, low-maintenance living in sought-after Chesapeake 23322! This impressive 4-bedroom, 2.5-bath residence offers 2,598 sq ft of beautifully designed living space with comfort and sophistication throughout. The showpiece is the exceptional 529 sq ft covered and screened outdoor retreat, finished with premium epoxy flooring and designed for elegant entertaining, alfresco dining, or peaceful relaxation. An additional patio, custom walkway, and professionally landscaped grounds enhance the home’s refined outdoor appeal. Enjoy a lock-and-leave lifestyle with HOA-maintained front landscaping and resort-style community amenities just moments away. Ideally situated near shopping, dining, parks, and major commuter routes, this exceptional home blends luxury, convenience, and effortless living.

1910 Briton Lane, South Chesapeake

404 Tanners Green Court, South Chesapeake

$400,000

3 Beds ⋅ 2.1 Baths ⋅ 10656296 MLS

VA-assumable 3.75% interest rate for VA-eligible buyer! Location, space, and style? This Chesapeake home has all three! Conveniently located near the city's major shopping, it welcomes you with great curb appeal, an open two-story foyer, and beautiful wood floors downstairs. The kitchen shines with granite countertops, while brand-new carpet gives the upstairs a fresh feel. The spacious primary suite features cathedral ceilings and a roomy bath with a soaking tub and separate shower. Two additional generously sized bedrooms offer plenty of space. Out back, a vinyl-fenced yard and covered patio create the perfect spot to relax, entertain, or fire up the grill. Come see why this one feels like home!

404 Tanners Green Court, South Chesapeake

$624,990

4 Beds ⋅ 2.1 Baths ⋅ 10656376 MLS

Seller is offering a $15,000 concession with a full price offer as Seller prefers to not do any additional improvements. This credit may be used at Buyers discretion towards closing costs, prepaids, fees and any buyer expenses or repairs. Stunning 4 bed 2 and a half bath custom-built home. Spacious bedrooms, upgraded kitchen with dual ovens and all newer appliances. Surround sound wired in the large family room. Newer flooring throughout. Custom built screened in back porch with a beautiful large yard. Relax on the front porch swing while overlooking the quiet cul de sac. Sought after neighborhood with the benefit of accessing major highways, bases & stores in minutes. Seller also providing a one year home warranty. Look at this one first! A beautiful place to come home!

1237 Spruce Lane, South Chesapeake

$267,700

3 Beds ⋅ 2 Baths ⋅ 10656397 MLS

Completely remodeled three bedroom, two bath with new LVP flooring, new carpet, a brand new kitchen, and updated bathrooms. One bedroom and a full bath are downstairs, which works well for guests, an office, or anyone who would rather skip the stairs. There's a front porch out front, and the backyard is large, with plenty of off street parking. Lakeside Park sits right around the corner, with a lake you can fish, two playgrounds, covered pavilions, and a walking path through the trees. Elizabeth River Park is about a mile up the road and has a dog park, a fishing pier, a boat ramp, and a paved path along the water. I-464 puts you in downtown Norfolk in about ten minutes. Updated and ready for its next owner.

1318 18th Street, Central Chesapeake

$440,000

3 Beds ⋅ 2.1 Baths ⋅ 10654807 MLS

Welcome to 933 Centurion Circle where the ease of townhome living meets the comfort and style of a single-family home. This beautifully designed residence offers a spacious lower-level recreation room that opens to a private backyard—perfect for creating your own outdoor retreat—along with a 2-car garage for added convenience. The main level features an expansive gourmet kitchen with granite countertops, a large island, upgraded LVP flooring, and a bright, open living room that flows effortlessly onto an oversized Trex deck ideal for entertaining or unwinding. Upstairs, three generous bedrooms provide plenty of space, including a luxurious owner’s suite with a tray ceiling, walk-in closet, and spa-inspired bath with dual vanities and an oversized shower with a seat. Located in Grassfield’s best-valued community, you’ll enjoy resort-style amenities such as water views, a private marina club, pool, clubhouse, docks, boat tie-off, and beach access-all with no flood insurance required!

933 Centurion 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.