Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a hidden gem nestled in the heart of Hampton Roads! Known for its rich history, diverse culture, and stunning natural beauty, Chesapeake offers a unique blend of suburban charm and urban convenience, making it an ideal place to call home.

Spanning over 350 square miles, Chesapeake is the second-largest city in Virginia by land area, boasting an impressive array of parks, waterways, and wildlife. The city is renowned for its extensive network of trails and outdoor recreational opportunities, including the picturesque Great Dismal Swamp National Wildlife Refuge, where residents can enjoy hiking, birdwatching, and kayaking in a serene setting.

Chesapeake's vibrant community is complemented by a strong economy, excellent schools, and a variety of shopping and dining options. The city’s neighborhoods cater to all lifestyles, from family-friendly communities to quiet, serene retreats. Whether you’re looking for a cozy single-family home or a modern townhouse, Chesapeake has something to suit every taste and budget.

For those who appreciate a strong sense of community, Chesapeake hosts numerous events throughout the year, including the popular Chesapeake Jubilee and various farmers' markets, fostering connections among residents and celebrating local culture.

With its strategic location, residents enjoy easy access to nearby cities like Norfolk and Virginia Beach, while still relishing the tranquility of suburban life. Whether you are a first-time homebuyer, a growing family, or looking to retire, Chesapeake, VA, is the perfect place to start your next chapter. Come discover the warmth and charm of this remarkable city!

Newest Listings in Chesapeake VA County

$265,000

3 Beds ⋅ 1.1 Baths ⋅ 10653172 MLS

Make this your first stop! This well-maintained 3-bedroom, 1.5-bath ranch in Norfolk Highlands offers the convenience of single-level living and the peace of mind that comes with major recent updates. The kitchen was remodeled in 2024, both bathrooms were remodeled in 2025, the HVAC system was replaced in 2024, and the gutters were upgraded in 2025. Pride of ownership is evident throughout, making this home truly move-in ready. The attached garage provides additional storage and convenience, while clear termite and moisture reports are already available for buyers. Conveniently located near shopping, dining, major interstates, and military installations, this home combines comfort, updates, and an unbeatable central location!

638 Milby Drive, Central Chesapeake

$650,000

5 Beds ⋅ 3 Baths ⋅ 10653164 MLS

Beautifully renovated 5BR/3BA home offering over 3,100 sq ft on nearly half an acre in Western Branch! Thoughtfully updated throughout, this home combines modern finishes with an exceptionally spacious and versatile floor plan. The first floor offers generous living and entertaining spaces, a family room with fireplace, plus a bedroom and full bath for guests or multi-generational living. Upstairs you'll find spacious bedrooms and an impressive primary suite. Enjoy a large backyard with plenty of room to entertain, an oversized 2-car garage, a whole-home generator, and PAID-OFF SOLAR PANELS for added energy efficiency with no solar payment! With extensive renovations, abundant space, and a desirable Western Branch location, this move-in-ready home delivers the updates, size, and features today's buyers are looking for!

2722 Gum Road, West Chesapeake

$375,000

4 Beds ⋅ 3 Baths ⋅ 10653176 MLS

Welcome home to this beautifully updated two-story home offering the perfect blend of comfort, style, and functionality. As you enter, you'll find a convenient first-floor bedroom and full bathroom, ideal for guests, multi-generational living, or a private home office. The heart of the home features an open-concept layout where the living room, dining area, and kitchen flow seamlessly together beneath soaring 9-foot ceilings with recessed lighting throughout, creating a bright and inviting space for everyday living and entertaining. The kitchen provides easy access to the fully fenced backyard, making outdoor gatherings a breeze. You'll also love the oversized shed/workshop, offering endless possibilities for storage, hobbies, or a dedicated workspace. Upstairs, you'll find two additional secondary bedrooms along with a spacious primary ensuite designed for comfort and privacy. Fresh paint and NEW flooring completed in 2026 give the home a modern, move-in-ready feel, while the NEWER HVAC system (2022) and NEW maintenance-free metal-wrapped roofing trim (2026) provide added peace of mind. Conveniently located near shopping, dining, schools, and major interstates, this home is ready for its next owner. Virtually staged. Schedule your private tour today!

4009 1st Street, Central Chesapeake

$283,999

2 Beds ⋅ 2.1 Baths ⋅ 10653079 MLS

Turnkey Luxury in Oakbrooke Crossing – Fully Updated & Pre-Inspected!Welcome to this beautifully updated 2-bedroom, 2.5-bathroom townhome-style condo in desirable Oakbrooke Crossing! This move-in-ready home features brand-new LVP flooring, fresh neutral paint, and an updated kitchen with laminate countertops, breakfast bar, and stainless steel appliances. Upstairs, you’ll find two spacious primary suites, each with its own private en-suite bathroom great for guests, roommates, or a home office. Enjoy added peace of mind with a brand-new water heater (2024), recently serviced HVAC, and a professional pre-inspection with the report available upon request.Conveniently located in the heart of Chesapeake, just minutes from Greenbrier shopping, dining, business centers, and interstate access. The low-maintenance condo lifestyle includes ground maintenance, trash service, and community upkeep. Ready for you! Schedule your showing today!

313 Holyoke Lane, South Chesapeake

$575,000

5 Beds ⋅ 3.1 Baths ⋅ 10653159 MLS

A rare financing opportunity and an exceptional floor plan set this completely renovated 5-bedroom, 3.5-bath home apart. Qualified buyers may be eligible to assume the seller’s existing VA loan at an incredible 2.625% interest rate, subject to servicer approval and existing loan terms. The versatile layout provides flexibility for extended family, guests, private workspaces and everyday living. Imagine cooling your home and enjoying the pool all summer with an electric bill that is virtually nonexistent. The seller reports exceptional energy savings from the solar-panel system, which will convey free and clear at closing. Other major improvements include new vinyl siding, garage door, HVAC, tankless water heater, fresh paint and so much more. The backyard paradise features a heated saltwater above-ground pool, new privacy fence and dedicated pool room that can also serve as a workout or recreation space. A well and sprinkler system help maintain the grounds.

412 Harper Court, South Chesapeake

$685,000

5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS

Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, South Chesapeake

$265,000

2 Beds ⋅ 2 Baths ⋅ 10653023 MLS

Welcome to this spacious and comfortable condo located in the desirable Riverwalk neighborhood. This home offers plenty of room to spread out and entertain. With both bedrooms connected to their own en suites you can enjoy both privacy and convenience. Upstairs includes a versatile loft area leading into the primary bedroom; providing additional space for a home office, reading area, or flex space. With new upgrades like the Heat Pump (2021) and the Roof (2025, by the association) you can have the peace of mind that you're in a good space. Outside, a cute private patio provides a pleasant spot to relax and enjoy some fresh air. The condo association gives low-maintenance living by covering the siding and roof, water and sewage, trash pickup, while maintaining the pool, clubhouse, and public spaces! With large living areas, a functional multi-level floor plan, and important updates, this condo is ready for its next owner! Setup a tour and make it you!

700 Nottoway River Court Unit D, South Chesapeake

$304,999

3 Beds ⋅ 1 Baths ⋅ 10653156 MLS

This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, Updated new LVP flooring, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily serve as a 4th bedroom, home office, playroom, or home workout space to fit your lifestyle. Step outside to your fully fenced backyard retreat, designed for both relaxation and entertaining. Enjoy summer days in the above-ground pool and unwind or host gatherings under the pergola on the patio while appreciating the privacy this backyard provides. Conveniently located near shopping, dining, schools, and major interstates, this move-in-ready home combines thoughtful updates, flexible living space, and exceptional outdoor setting you won't want to miss.

2801 Southport Ave., Central Chesapeake

$409,000

4 Beds ⋅ 2 Baths ⋅ 10653157 MLS

Renovated over the past few years, this beautifully kept brick ranch home is ready to welcome its next owners! Inside, the kitchen offers a fresh, modern feel with crisp white shaker cabinets, gleaming granite countertops, and newer stainless-steel appliances that make every day cooking a pleasure. Enjoy the charm of the hardwood floors, and other cozy features throughout this home as you add your own touch of decor! Before entering your backyard, enter into your fully screened and covered sunroom from your back door, enjoying the sounds and peace of your backyard. The adjoining fully enclosed sunroom provides a bright, inviting space for relaxing or entertaining, while the large backyard offers plenty of room for gatherings, play, or quiet evenings outdoors. Recent updates - including a newer installed roof and windows (2022), new front fencing (2025) newly remodeled bathroom showers (2024), and newly encapsulated crawl space by JES (2025), and for added peace of mind and long-term value with transferrable warranties! This charming home is truly move-in ready. Schedule your showing today!

2615 Cedar Road, South Chesapeake

$509,900

4 Beds ⋅ 2.1 Baths ⋅ 10653139 MLS

Welcome to 508 Schaefer Avenue, a beautifully maintained 2018-built home in Chesapeake’s Deep Creek area! With 4 bedrooms, 2.5 baths, and 2,398 square feet, this home offers the space today’s buyers are looking for. The main level features an open flow between the kitchen, dining, and living areas, along with a separate front flex room ideal for a home office, playroom, or sitting room. The bright kitchen includes white cabinetry, granite countertops, a large island with seating, and stainless steel appliances. Upstairs, the spacious primary suite includes a separate sitting area and an ensuite bath with dual vanities, a soaking tub, and a separate glass shower. Three additional bedrooms and an upstairs laundry room add everyday convenience. Outside, enjoy a level backyard, concrete patio, wooded backdrop, and attached two-car garage. Potential 5.75% assumable loan opportunity for qualified buyers, subject to lender/servicer approval, underwriting, applicable terms, and buyer qualification. Schedule your private showing today!! THIS ONE IS A STEAL!!!

508 Schaefer Avenue, West Chesapeake

$440,000

3 Beds ⋅ 3 Baths ⋅ 10652901 MLS

Welcome home to this stunningly renovated farmhouse, where modern design meets classic charm in the heart of Chesapeake. Completely rebuilt from the studs up, this 3-bedroom, 3-bathroom gem offers 1,963 square feet of thoughtfully designed living space across two stories on 3/4th an acre. Step inside to an open-concept kitchen featuring striking black-and-white countertops, statement lighting, and modern farmhouse accents throughout. The main-level primary suite is a true retreat, boasting two generous closets and a spa-inspired bathroom with a sleek, step-in tiled shower. Sophisticated gray-toned flooring flows seamlessly throughout the home, adding warmth and cohesive style to every room. Outside, a detached garage provides excellent storage or workshop potential. Come make your dreams your reality! This one will not last long!

4057 Woodland Drive, West Chesapeake

$290,000

3 Beds ⋅ 2.1 Baths ⋅ 10653125 MLS

Short sale — offer accepted and currently pending lender approval.

526 Windward Drive 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.