Chesapeake

Surrounding the waters of a tranquil Elizabeth River tributary, lies an area of Chesapeake, Virginia, known as Deep Creek-Portsmouth, where residents enjoy a suburban cocktail of quiet, attractive subdivisions and highly-rated schools with a twist of the great outdoors. “The Deep Creek area is Chesapeake’s best-kept secret,” says Susan Jubilee, an associate broker with Re/Max Alliance who has been selling real estate in the Hampton Roads area for 17 years. “It’s the perfect mix of older and newer homes and waterfront and non-waterfront homes. It’s a real bedroom community that’s attractive to a lot of people, from young families to single professionals to older folks.” According to Jubilee, Deep Creek is a favorite spot for military personnel to settle. “Transplants from other naval base areas around the country, like San Diego, love the area. And they love the price and value of the homes.”<br><br>Deep Creek-Portsmouth offers a variety of home options, from 1970s brick ranch-style single-family homes in established sidewalk-lined subdivisions to modern new construction with hints of classic styles, like Craftsman and Victorian, built on ample lots, many with water views. Home sizes range from 1,000 to 4,500 square feet with two to five bedrooms, and list prices tend to fall between $265,000 and $770,000. Homes here tend to sell well, and the appreciation and growth in the area has been stable.<br><br>Area children attend Chesapeake Public Schools, including Deep Creek Central Elementary, rated an A-minus by Niche, and Owens Middle, which earns a B-plus rating. After middle school, students can attend Grassfield High School, rated an A and considered the No. 5 best public high school in the Norfolk area by Niche. <br><br>With lovely local waterways, numerous area parks and the Great Dismal Swamp Wildlife Refuge on the doorstep, there are plenty of opportunities to enjoy the great outdoors in and around the Deep Creek-Portsmouth area. Anglers can catch largemouth bass in Deep Creek, and hikers can experience a scenic journey through the Dismal Swamp along the nearby Portsmouth Ditch Trail. For fun with the kids and pup, there’s Deep Creek Park, with its playground, baseball fields and dog park. Surrounded by water, Deep Creek Lock Park, named for the locks built by the Army Corps of Engineers to separate the saltwater of Deep Creek from the Dismal Swamp Canal’s freshwater, is a wooded, tidal inlet oasis with footbridges and trails, a canoe launch, a play area and an observation tower that overlooks the locks.<br><br>The nearby Crossings at Deep Creek shopping center, conveniently located along Moses Grandy Trail, is perfect for a quick grocery run at Food Lion. Affordable household staples can be found at the Dollar General. Shoppers can then grab a bite at the popular El Puente Mexican Grill, where the salsa may be hot, but the margaritas are ice cold. Deep Creek-Portsmouth-area folks have even more retail and dining choices near the intersection of Dominion Boulevard and Grassfield Parkway, where there’s a Walmart Supercenter and a popular local chain restaurant called The Dirty Buffalo, which serves sports bar favorites like wings, burgers and mac ‘n cheese bowls in a family-friendly atmosphere.<br><br>From the Chesapeake Virginia Wine Festival to the KayaXpedition paddle craft festival, the city of Chesapeake is home to countless events throughout the year, and the Deep Creek-Portsmouth area of town is no exception. Izaak Walton Park off of Deep Creek’s Trailsend Lane has been known to host the Deep Creek Ruritan Club’s annual BeefFest, where folks line up for all-you-can-eat beef barbecue, pony rides, face painting, remote-control monster truck races and more.<br><br>Though public transit isn’t readily accessible in the Deep Creek-Portsmouth area, Interstate 64 runs through the area, making the commute to other Hampton Roads destinations, like the 13-mile drive to downtown Norfolk or the 24-mile trip to Oceana Naval Air Station in Virginia Beach, a little easier. However, with several multi-year – and multi-million dollar – bridge, tunnel and highway improvement projects in effect until 2027, local traffic woes are a reality. “Commuting will improve when the construction is complete,” Jubilee says. “Everyone understands that it's temporary.”

Great Bridge is a suburban community in the historic and mostly rural city of Chesapeake. Located on the Elizabeth River, Great Bridge has a plethora of single-family homes and condominiums to suit all lifestyles. What was once a small town experienced significant growth in the 1980s. If you find yourself craving more outdoor space, Great Bridge is home to many beautiful parks, rivers and lakes. <br><br>Most of the properties are large, single-family homes with bigger yards, but there are also many townhomes and condominiums. Homes in Great Bridge are relatively new and were built after the 1980s. Homes here tend to stay on the market for about three weeks and typically sell for between $400,000 to $700,000. There are also some 55+ communities and senior assisted living facilities in the nearby area. <br><br>Chesapeake City Public Schools serves the neighborhood’s students with a collection of well-rated schools. Kids may start at Cedar Road Elementary School, which earns an A grade from Niche, before transitioning to Great Bridge Middle School, which gets a B-plus. Students may then attend Great Bridge High School, also with a B-plus grade, which has produced several professional athletes and is famous for its nationally-ranked wrestling program. <br><br>The Chesapeake Planetarium and Chesapeake Arboretum are popular attractions in the neighborhood. Bells Mill Park offers footpaths through scenic meadows and wetlands and amazing views of the Elizabeth River. Forrest Lakes Playground is a small, residential playground perfect for kids year-round. Kevin Houston Park also offers a big children's playground, picnic tables and a small trail. Golfers can enjoy the Chesapeake Golf Club, an 18-hole course with an on-site pro shop and restaurant. <br><br>Great Bridge is named after The Battle of Great Bridge, a lesser-known but important victory for the Americans over the British in the Revolutionary War. This battle resulted in the final removal of the British Government from the Colony and Dominion of Virginia. Visit the Great Bridge Battlefield & Waterways Historic Park to explore the museum and its trail along the Elizabeth River. <br><br>Plenty of nearby retailers sit along Cedar Road, including Walmart, Food Lion, Aldi and Walgreens Pharmacy. For fresh, local, food, you can visit the Chesapeake Farmers Market on Wednesdays and Saturdays. There are also popular local restaurants close by like Chesapeake Pizza, a family-owned joint that’s been serving stone-baked pan pizzas in Great Bridge since 1973. <br><br>Great Bridge is somewhat bikeable and walkable, but the area is still mostly car-dependent. Dominion Boulevard is a major road that connects residents to Interstate 64 and the rest of Hampton Roads. There are also public bus stops with daily service along Cedar Road. <br><br>The Battle of Great Bridge is remembered every year with a free, public event at Battlefield Park South. The two-day event, which takes place each December, offers re-enactments of the battle on both days, historical displays and lectures, skilled artisans and children's crafts and activities.

Greenbrier East presents a combination of modern urban living with suburban flair. The neighborhood is west of Chesapeake's downtown and city administrative offices. The community covers about 18 square miles, with the southeast section remaining mostly undeveloped woodlands. There are several lakes in and adjoining the neighborhood, and the coastline of the Atlantic Ocean is a mere ten miles to the east. “It’s one of those neighborhoods that everyone wants to be in,” says Russell Bryant, a Team Lead with Creed Realty, and a longtime resident of Hampton Roads who’s been selling homes in the area for nearly 15 years. “It’s a great segway for those who want a more suburban life away from the hustle and bustle of the city, without going too deep into rural Chesapeake.” <br><br>Stumpy Lake Natural Area, a nearly 1,500-acre green space, highlights the neighborhood’s recreation. The area offers a 1.5-mile looping trail through the woodlands, a large lake for fishing and kayaking and an 18-hole golf course. Chesapeake City Park is a large municipal green space with a wooded playground, skatepark, basketball courts and a stage for local events. There’s also Greenbrier Sports Park which offers tennis courts and baseball diamonds. For those looking to escape the summer heat, the Greenbrier Family YMCA has an indoor and outdoor pool, a gym and a basketball court. <br><br>There are a ton of shopping options nearby, including Greenbrier Market Center with Target, Harris Teeter and Best Buy. There’s also a Walmart, Sam’s Club and Kroger in the northwest end of the neighborhood. Residents can head to Central Meats, a local market with a large selection of meat, poultry and seafood. “It’s a massive neighborhood butcher that’s been there for over 50 years,” adds Bryant. “You can get just about any cut of meat you’d want, and they cater as well.” There are also several popular local restaurants like The Egg Bistro with a large brunch menu, Pirate’s Cove for locally sourced seafood and Windy City Pizza for deep dish and traditional pies. <br><br>Homes here were built after the 1960s and are arranged along traditional suburban streets with cul-de-sacs. There are older ranch-style homes as well as plenty of new traditionals. New subdivision construction is ongoing in the neighborhood, and many of the older homes have undergone recent renovations. Single-family homes typically stay on the market for about a month and sell for $500,000 to $750,000. There are also condos and townhouses available to purchase or rent, with those usually selling for $250,000 to $500,000. Those new to east coast living may need to adjust to the occasional hurricane and tropical storm warnings. Otherwise, expect humid, subtropical weather conditions in the area, with the ocean playing a big part in that. <br><br>Kids may start at Greenbrier Primary for kindergarten through second grade, then go to Greenbrier Intermediate, which earns an A-minus, for grades three to five, before transitioning to Greenbrier Middle, which gets a B-plus. Students may then attend Indian River High which gets a B and boasts a successful athletics program, with the school having earned state championships in football, basketball and marching band. <br><br>The Chesapeake Wine Festival takes place each October in Chesapeake City Park. Residents can sample a large wine selection, listen to live music and shop from a variety of local vendors. The Chesapeake Arboretum hosts a popular Autumn Festival every year. May is Bikefest month in Chesapeake, featuring highlighted rides on trails in the city. Events like the Virginia Arts Festival draw tens of thousands to several performance venues throughout the area to enjoy world-renowned performers and workshops, along with activities designed just for kids. <br><br>Due to the layout of the City of Chesapeake, with several distinct residential and commercial areas, most residents of Greenbrier East drive to their place of work. But a well-planned street and highway system means relatively short drive times. Norfolk International Airport, one of the largest in the region, is 15 miles north. There are also two nearby Amtrak stations in Norfolk and Newport News that connect with north-south commuter lines.

Located off the banks of the Elizabeth River, Greenbrier West is a sprawling Chesapeake suburb marked by clusters of residential subdivisions and apartment complexes. Homes in this neighborhood reflect a range of newly built architectural styles, as most of them were constructed after the 1990s. The area’s natural beauty and ecological diversity can be explored at the Chesapeake Arboretum nature site or the Oak Grove Lake Park. The school district serving students in this neighborhood is Chesapeake Public Schools, which receives an A-minus rating from Niche. Greenbrier West is also home to the Chesapeake Regional Medical Center and the historic site of the Great Bridge Battlefield, a remnant of the region’s involvement in the Revolutionary War. <br><br>Homes here tend to cluster on cul-de-sacs in residential subdivisions surrounded by dense wooded areas. Two-bedroom ranch styles with brick exteriors and paved driveways can sell for $240,000, while four-bedroom American Craftsman residences built in 2005 can cost more than $550,000. “There are also some homes built around the edges of the Elizabeth River,” says Katie Burke, Century 21’s top Virginia Realtor who has lived in the area her whole life. Some of these five-bedroom riverfront properties can cost close to $1 million. Greenbrier West also has a number of apartment communities – such as The Cedars at Greenbrier and Wimbledon Chase Condominiums – where residents can find townhomes and condos that line winding dead-end streets and are often priced between $150,000 and $300,000. <br><br>B.M. Williams Primary School is a B-plus-rated institution that offers education for young students in pre-kindergarten through second grade. For grades three through five, students can attend Crestwood Intermediate, which also has a B-plus rating and feeds into Crestwood Middle School, a B-minus institution serving grades six through eight. Older learners might go to secondary school at the B-plus-rated Oscar F. Smith High School, which offers an International Baccalaureate Program and is ranked #4 on Niche’s “Standout High Schools in Norfolk Area” list. <br><br>Oak Grove is a 150-acre park comprised of wetlands, hardwood forests and a central 65-acre lake of the same name. Residents can walk the lake’s perimeter along a 1.5-mile multi-use trail that passes through the park’s picnic areas and playgrounds. Two lakefront platforms on opposite sides of the lake might serve as a fishing dock or an observation deck. For outdoor recreation tied to regional history, locals can go to the Great Bridge Lock Park, which sits on a small river peninsula and features an outdoor amphitheater, picnic shelters, a playground and a two-lane boat ramp. This park is located at the original site of the Battle of Great Bridge, which took place on December 9, 1775, during the beginning of the Revolutionary War. The park’s Great Bridge Battlefield and Waterways Museum aims to educate visitors on the battle’s importance and the area’s overarching canal history. <br><br>Gainsborough Square is a neighborhood shopping plaza with a Food Lion grocery store and a Rite Aid pharmacy alongside local dining spots, including Pirate’s Cove, a seafood restaurant, and Osaka Ramen & Sushi. Less than a mile outside the neighborhood is the Greenbrier Market Center, where residents can shop for household goods and apparel options at department stores like Target, Best Buy, Hobby Lobby and Marshalls. “A lot of homeowners also like this area for its proximity to Greenbrier Mall,” Burke says; located less than 3 miles away, residents can go to this indoor mall and browse dozens of specialty shops, dining options and retail outlets. <br><br>Virginia State Route 168 and U.S. Route 17 both run through this neighborhood and feed into Interstates 464 and 64, which connect commuters to Norfolk and surrounding Chesapeake County areas. The Norfolk International Airport is an approximately 16-mile drive away and operates flights from several commercial carriers. Hampton Roads Transit runs a fixed bus route with multiple stops along Battlefield Boulevard.<br><br>Since 1983, the Chesapeake community has celebrated its city’s founding by throwing an annual Jubilee in Chesapeake City Park. During this weekend-long event, musical guests perform live at the park’s Robert G. Bagley Stage and locals can go on carnival rides operated by Amusements of America. In the spring, the Chesapeake Bicycle/Trails Advisory Committee hosts Bike Fest, an outdoor recreation event that invites community members to explore 8 miles of biking trails while enjoying live music and food trucks.

Along one of the world's largest natural harbors, tucked away on a tributary to the Elizabeth River, is Indian River. Residents in this Chesapeake suburb have access to a number of outdoor parks, community centers and water recreation. Neighborhood organizations like Friends of Indian River are dedicated to preserving the area’s rivers and green spaces by promoting volunteer clean-up events and establishing community gardens. The architecture here reflects a combination of the old and new: "This is a very well-established neighborhood that has homes ranging in build date from 1950 to 2023," says Katie Burke, Century 21’s top Virginia Realtor who has lived in the area her whole life. "Students here are zoned for the Chesapeake Public School district, which receives an A-minus rating from Niche and is also ranked No. 4 on Niche’s “Best School Districts in Norfolk Area” list. Residents are a short drive from downtown Norfolk located northeast of the neighborhood across the Elizabeth River.<br><br>Single- and multi-family homes, condo communities and newer residential developments display a mix of architectural styles that can be found throughout the neighborhood. Some of the more common styles here include ranch-style homes with brick exteriors and recent builds that incorporate traditional-style architecture and often feature vinyl siding. The median home price in Indian River is just under $300,000, but some of the newly constructed five-bedroom properties can sell for more than $630,000. Condominiums and townhome complexes also dot the neighborhood; communities like Coleman Farms offer residents a number of private amenities, including a pool, fitness center and clubhouse. <br><br>Younger students can attend Thurgood Marshall Elementary, a B-minus school, for primary education. Students in grades six through eight might go to Indian River Middle School, also rated B-minus, which then feeds into B-rated Indian River High School for students in grades nine through 12. Indian River High also has a college and career center that offers resources for students who might want to apply to higher education institutions, find employment opportunities or enroll in the military following their graduation.<br><br>Indian River Park covers over 90 acres of forests and open green space; the South Military Highway runs through and splits the park into a north side and a south side. On the northern side, residents can find a playground, basketball courts and the Rokeby Community Center. South Indian River Park is made up of dense woods and offers park-goers access to Virginia’s indigenous natural beauty through birdwatching areas, hiking trails and rain gardens. Locals can also go to the Indian River Community Center on Old Greenbrier Road for indoor recreation facilities, including a fitness center, gaming area and a gymnasium with locker rooms. <br><br>Volunteer cleanups and Adopt-A-Park events are led by the Friends of Indian River and aim to bring the community together by removing pollution and invasive species from the area’s parks and rivers. This organization also drives initiatives to support local small businesses, maintain neighborhood streetscapes and promote sustainable gardens.<br><br>In a shopping plaza off Woodlake Drive, residents can stock up on groceries at Kroger Marketplace, find athletic equipment at Dick’s Sporting Goods, or browse a variety of retail items at HomeGoods and Five Below. Locals can also go to the Parkview Shopping Center to dine at the Crazy Buffet & Grill, the largest Asian cuisine restaurant in Chesapeake. Right next door is Eagles’ Nest Rockin’ Country Bar, a local hot spot for live music and entertainment where residents can enjoy performances by top country music artists, sing their hearts out in karaoke and dance the night away to DJ setlists. <br><br>Commuters are an 8-mile drive from downtown Norfolk, which they can access using South Military Highway. "Interstate 264 and 64 are accessible in no more than 10 minutes," Burke says. Indian River’s southern border runs along Interstate 64, which feeds into routes leading to Virginia Beach and Newport News. Public bus stops and fixed routes on South Military Highway are operated by Hampton Roads Transit. Residents are approximately a 10-mile drive away from the Norfolk International Airport.

Between U.S. Route 17 and the Chesapeake Expressway lies Pleasant Grove West. Large farms, stretches of wildlife preservations and growing communities make up the area. The neighborhood sits 10 miles south of downtown Chesapeake. “This is an up-and-coming neighborhood in a beautiful area that’s just a step away from the hustle and bustle of nearby cities,” says Morgan Xenos, a Realtor with Dragas Companies Realty Inc who spends most of her time in Pleasant Grove West. <br><br>Many residents live in ranch-style homes with four bedrooms on large lots. Neighbors live nearby, but there’s space between the homes to create a layer of privacy. Homes from the 1970s and early 2000s pepper the area, but most units were built as recently as 2019. The brand-new arts-and-crafts and colonial-revival homes feature wide driveways and spacious garages. Most homes in Pleasant Grove West range from $500,000 to $775,000, but homebuyers can find five-bedroom homes that sell for $1 million or more. Open lots that span over 3 acres rest nearby for those who want to build their dream home. <br><br>Pleasant Grove West falls under the Chesapeake Public School District. “People move here to find houses that are cheaper than those in Hickory but still sit close to Hickory schools,” Xenos says. Hickory Elementary gets students engaged with the community through a variety of volunteer events. Students continue their education at Hickory Middle. Kids might join the softball team, boys' volleyball team or the Harry Potter Club. When it’s time for high school, Hickory High has a championship-winning marching band and job fairs to push students toward a bright future. Those who live closer to downtown Chesapeake often send their young children to Grassfield Elementary. Kids learn with small group projects that bring classmates and teachers together. Hugo A. Owens Middle is the natural next step for residents and features a popular drama club and band. Students interested in STEM thrive at Grassfield High by enrolling in the Governor’s STEM Academy. This program gives students specialized STEM classes every year of high school. All of these schools receive a rating of B-plus or higher from Niche. <br><br>Wildlife preservations cover the southernmost area of Pleasant Grove West. Locals wanting to reconnect with nature visit the Cavalier Wildlife Management Area or the Northwest River Natural Area Preserve. The Cavalier WMA is popular for hunting deer in the fall or camping under the stars in the summer. The Northwest River Preserve features long walking trails and marshes open for kayaking. Young baseball and softball athletes head to the Southern Chesapeake Athletic Association when spring rolls around. This nonprofit league hosts events throughout the year to help budding athletes grow. If locals prefer soccer, Cornland Park has fields ready for a tournament or impromptu game. There's a nearby playground for kids to enjoy while their older siblings play on the fields. <br><br>The Edinburgh West and Edinburgh North Shopping Centers make shopping simple. Shoppers exit off the expressway to get essentials at Target or Walmart. Residents who live closer to Dominion Boulevard visit the Walmart in Dominion Commons. Popular chain restaurants also sit along the expressway, but residents flock to family-owned restaurants like the Gran Rodeo Mexican Bar and Grill for lunch and dinner. Happy hour isn’t complete without one of their signature cocktails. The Dirty Buffalo, off Dominion Boulevard, offers a more laid-back atmosphere. Customers can catch a Buffalo Bills game while enjoying wings coated in a spicy sauce or smokey rub. <br><br>“Locals visit Greenbriar Farms throughout the year. It’s a cute place with fun activities and a nice restaurant,” Xeno says. Visitors can pick out their Christmas tree in the winter, choose plump pumpkins in the fall or fill a basket with handpicked strawberries in the summer. When guests need to refuel after spending time on the farm, The Hive Farm Bar and Grill has outdoor seating and a menu stuffed with sticky honey buns, pulled pork sandwiches and jack honey whiskey lemonades. Future pilots and aviation enthusiasts frequent the Chesapeake Regional Airport. This airport has a flight center to train new pilots and offers private commercial flights. Chapter 339, a group of aircraft builders and pilots, also meets here for social meetings, seminars and educational programs.