Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a hidden gem nestled in the heart of Hampton Roads! This vibrant city is known for its rich history, diverse culture, and stunning natural beauty. Spanning over 350 square miles, Chesapeake is the second-largest city in Virginia by land area, offering a unique blend of suburban charm and urban convenience.

Chesapeake is renowned for its extensive parks and outdoor recreational opportunities. With over 22,000 acres of parkland, residents can enjoy hiking, biking, and fishing in scenic locations like Great Dismal Swamp National Wildlife Refuge and Chesapeake City Park. The city is also home to the picturesque Elizabeth River, which provides ample opportunities for boating and water sports.

Rich in history, Chesapeake boasts several historical sites, including the Battle of Great Bridge, which played a pivotal role during the American Revolution. The city’s cultural diversity is reflected in its vibrant community events, festivals, and local dining scene, offering everything from Southern comfort food to international cuisine.

Families will appreciate the excellent educational opportunities provided by Chesapeake Public Schools, along with a variety of private and charter schools. The city’s family-friendly atmosphere, combined with its strong sense of community, makes it an ideal place to call home.

With its convenient location, just a short drive from Norfolk and Virginia Beach, Chesapeake offers easy access to the best of coastal living while maintaining its own unique identity. Whether you’re looking to buy your first home, relocate, or invest in real estate, Chesapeake, VA, is a place where dreams can flourish! Come explore all that this remarkable city has to offer – your new home awaits!

Newest Listings in Chesapeake VA County

$195,000

2 Beds ⋅ 2 Baths ⋅ 10649902 MLS

$3000 Carpet Allowance! This well-maintained 2-bedroom, 2-bath first-floor condo in desirable Miars Farm offers comfortable single-level living in the heart of Western Branch. Move-in ready with a new HVAC system and hot water heater, plus newer stainless steel appliances. The spacious layout features two full baths and easy access to the rear patio with additional outdoor storage. Community amenities include a pool and clubhouse, with trash service and grounds maintenance included for added convenience. Ideally located near shopping, dining, schools, and interstate access, this condo makes everyday living simple and convenient.

3520 Sugar Run Run, West Chesapeake

$440,000

4 Beds ⋅ 2 Baths ⋅ 10649889 MLS

Welcome home to this classic 4 bedroom, 2 bath brick home offering timeless character and plenty of space to enjoy inside and out. A charming side porch adds to the home’s inviting appeal, while the spacious backyard is made for warm-weather living with a large in-ground pool and plenty of room to relax or entertain. An additional detached brick building, formerly used as a garage, offers flexible bonus space and includes a full bathroom and kitchenette. Use it as a workshop, home office, pool house, hobby space, or additional storage. The possibilities are yours. With its classic brick exterior, great outdoor spaces, and versatile detached building, this property offers a combination of character, function, and potential.

2213 Wildwood Road, South Chesapeake

$726,960

4 Beds ⋅ 4 Baths ⋅ 10649866 MLS

Under Construction Feb 2027 Delivery - 4 BR each with generous ensuite. Honoring the natural setting with waterfront living surrounded by egrets, wildlife and protected land. The oversized windows will immerse you in light at every turn. Open and Elegant modern home. Entertainers' kitchen - Quartz counters, custom backsplash, Matte-finish GE Cafe appliance package, and custom range hood. Extensive upgraded HW flooring & 10' ceilings midlevel, HUGE 2nd floor Screened Porch with composite decking overlooks estuary rear yard. True entertainers' home! Stunning primary bedroom with gorgeous views, egrets, and serene trees swaying in the breeze. The spa-like primary suite boasts a freestanding tub, zero-entry tiled shower, and 12' Quartz vanity. Exterior black windows and black gutters. Custom Paver driveway and extensive landscaping. Breathe in the fresh air and NO HOA!

1906 Mccoy Rd, South Chesapeake

$389,000

3 Beds ⋅ 1.1 Baths ⋅ 10649886 MLS

Charming and updated 3-bedroom, 1.5-bath ranch in the heart of Western Branch, just minutes from Chittum Elementary! The spacious, updated kitchen is designed for gathering, with plenty of room to cook, connect, and entertain. Relax on the screened-in porch overlooking the fenced backyard. A large detached garage and extra-wide driveway provide exceptional space for multiple vehicles, a boat, RV, storage, or hobbies. Conveniently located near shopping, dining, schools, and major roadways. A wonderful place to call home!

4208 Nina Drive, West Chesapeake

$425,000

3 Beds ⋅ 1.1 Baths ⋅ 10649793 MLS

Welcome to this charming 3-bedroom, 2-bath Colonial style home tucked away on a quiet cul-de-sac in Etheridge Manor! Full of character and warmth, this inviting home features exposed wood beams in the living room, a cozy fireplace, a sunny breakfast area, and new carpet throughout. Step outside onto the new deck, perfect for morning coffee, weekend gatherings, or relaxing evenings. With its classic charm, peaceful setting, and welcoming neighborhood, this home is ready for new memories. Come see why this one is easy to love!

604 Winscott Court, South Chesapeake

$765,000

4 Beds ⋅ 4 Baths ⋅ 10649884 MLS

Stunning all-brick former Homearama showcase home offering spacious living and endless potential! Designed with an open floor plan and soaring ceilings, the home features a chef's kitchen with two oversized granite islands, abundant workspace, and a wine cooler station. Enjoy a media room with wet bar, sunroom, glass-enclosed side porch, and first-floor study with custom built-ins. The spacious primary suite features a wraparound walk-in closet and all-marble bath. Additional highlights include marble foyer flooring, two ensuite bedrooms, newer HVAC systems, and generous living spaces. Enjoy community amenities including a pool, tennis courts, and children's playground, plus convenient access to shopping, dining, and interstates. Bring your vision and finishing touches to make this distinctive home your own! Seller is offering a closing cost credit with an acceptable offer!

700 Old Fields Arch, South Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10649882 MLS

MM Ashbee at Riverview Landing - To Be Built. The Ashbee is a 5-bedroom home with a first-floor Owner’s Suite, four bedrooms and a loft upstairs. Open-concept kitchen with large island, high-end finishes, double ovens, pantry, and plenty of counter space. Features include first and second-floor laundry (or option to convert upstairs laundry to a full bath), mudroom, and optional rear covered porch. Standard features and design options available. Convenient to shopping, dining, healthcare, and major roadways

MM Ashbee, South Chesapeake

$230,000

2 Beds ⋅ 2 Baths ⋅ 10649847 MLS

Welcome to this beautifully updated, move-in ready 2-bedroom, 2-bath condo! Freshly painted throughout, this home features new carpet, vinyl flooring, and all-new kitchen appliances. HVAC was replaced in 2021 and the hot water heater in 2023. The bright, open layout offers a spacious living area great for relaxing or entertaining. The primary suite includes a private bath and ample closet space. The second bedroom and full bath are great for guests, family, or a home office. Enjoy low-maintenance living with several stores and restaurants nearby. Conveniently located near Chesapeake Regional Medical Center, the Municipal Center, Greenbrier, and Downtown Norfolk. Don't miss this move-in ready home!

315 Gainsborough Square, South Chesapeake

$839,540

6 Beds ⋅ 4.1 Baths ⋅ 10649851 MLS

Welcome to the Tillman at Riverview Landing! This Property is great for multigenerational families! This spacious home includes 6 bedrooms, 4.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy for guests, teens, or extended family. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. This house is complete with a FINISHED BASEMENT! Photos are from the builder's library, actual finishes and features may vary.

1228 Kidbrooke Street, South Chesapeake

$480,000

4 Beds ⋅ 2 Baths ⋅ 10649831 MLS

This beautifully updated 4-bedroom, 2-bath ranch in Chesapeake is one you’ll want to see first! Step inside to find a refreshed kitchen, spacious primary suite, inviting living room, and comfortable one-level living with plenty of space to make your own. There’s even a bonus room above the 2-car garage, perfect for a home office, playroom, media room, hobby space, or guest area! Outside, the gorgeous deck overlooks a peaceful backyard with beautiful water views, creating the perfect setting for morning coffee, evening get-togethers, or simply enjoying the scenery. With thoughtful updates, generous living spaces, a 2-car garage, bonus room, and tranquil water views, this home has the space, charm, and setting you’ve been looking for. Save yourself some time and put this one at the top of your list! Come see it for yourself!

757 Willow Bend Drive, South Chesapeake

$199,900

2 Beds ⋅ 1.1 Baths ⋅ 10649757 MLS

Charming, move-in ready bungalow nestled on an large 60 x 120 lot! Inside, you will find beautiful original hardwood floors flowing throughout a bright and welcoming layout. The property also features jack & jill 1/2 bath, a detached 1-car garage and includes all appliances conveying as-is. Ideally located for an easy commute, you are just minutes from major expressways, Greenbriar area, downtown Norfolk, Portsmouth, premier shopping, great restaurants, multiple vibrant city parks, local shipyards, and military bases. (photos edited by AI)

1804 Portlock Road, Central Chesapeake

$325,000

4 Beds ⋅ 2 Baths ⋅ 10649820 MLS

Under Contract - Listing for Input Only!

1212 Dragon Lane, 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.