About
Michael Freeman's Approach to Chesapeake
Chesapeake is big, about 338 square miles of land, and a Great Bridge cul-de-sac has little in common with a Western Branch townhome or a Hickory farm parcel. Michael Freeman treats each as its own market.
Great Bridge and Hickory focus
Great Bridge and Hickory are two of the Chesapeake neighborhoods Michael concentrates on most.
On the Southside since 2002
He has handled about 500 transactions across Hampton Roads since 2002, including Chesapeake and the rest of the Southside.
Norfolk police service
Before real estate, Michael served as a police officer in Norfolk, just across the city line, and earlier in New York City.
Military Relocation Professional
His MRP designation helps service members reporting to Southside commands plan a purchase around fixed dates.
This Area
Understanding Chesapeake, Virginia
Chesapeake formed in 1963 from South Norfolk and Norfolk County, and it still holds both suburbs and open farmland. ZIP 23320 centers on Greenbrier, the city's commercial hub around Greenbrier Mall, City Park and the Dollar Tree headquarters, with River Walk and Butts Station Road nearby. Western Branch's 23321 runs along I-664 and Portsmouth Boulevard, where Chesapeake Square is being redeveloped. To the south, 23322 takes in Great Bridge, the 1775 battlefield and the canal locks, then stretches through Edinburgh and Etheridge Lakes into Hickory toward the North Carolina line. Citywide, homes sold in about four weeks at full price in summer 2026, and 74% of homes are owner-occupied. Tolls on the Chesapeake Expressway and the Veterans Bridge, flood exposure near the Elizabeth River branches, and parcel rules in rural Hickory all shape what a home is worth here.
“Chesapeake is several towns sharing one name, and Michael Freeman makes sure buyers know exactly which one they are moving into.”
Market Snapshot
Chesapeake Home Values Right Now
These are citywide figures, the most current Redfin data for Chesapeake. Redfin's pages for the individual ZIPs lag behind, and their latest figures appear in the insights below.
Source: Redfin, City of Chesapeake, three months ending August 2026. Michael can pull current numbers for any Chesapeake neighborhood.
Local Insights
100 Facts About Chesapeake, Virginia
Gathered from Redfin, the Census Bureau, Chesapeake Public Schools, Virginia Works and other public sources. Click any category to open it.
Market Fundamentals
- Chesapeake's citywide median sale price was $446,704 for the three months ending August 2026, up 5.7% year over year, on 1,151 sales (Redfin).
- Citywide, Chesapeake homes sold in a median of 28 days at a 100.2% sale-to-list ratio, and 38.2% went above asking (Redfin, August 2026).
- Redfin rates Chesapeake "Very Competitive," with a citywide Compete Score of 76 and a median of $218 per square foot.
- In Greenbrier's 23320, the median sale price was $382,414 for the three months ending June 2026, and homes sold in a median of 24 days (Redfin).
- 44.6% of 23320 homes sold above list in that period, and the ZIP's Compete Score was 83 (Redfin).
- In Western Branch's 23321, the median sale price was $395,000 in November 2025, the latest month Redfin had posted for that ZIP, up 9.1% year over year.
- In 23322, home to Great Bridge and Hickory, the median sale price was $598,000 in October 2025, the latest Redfin had posted, on 253 sales.
- Median price per square foot ran $216 in 23320, $199 in 23321 and $230 in 23322 in Redfin's latest posted figures for each ZIP.
- Census median home values by ZIP are $346,400 in 23320, $367,900 in 23321 and $463,300 in 23322 (ACS 2020-2024).
- Chesapeake's median owner-occupied home value is $378,400, and median gross rent is $1,586 a month (ACS 2020-2024).
- Median monthly owner costs in Chesapeake are $2,142 with a mortgage and $717 without one (ACS 2020-2024).
- Chesapeake's real estate tax rate was $1.01 per $100 of assessed value as of July 2025, down from $1.05 before FY2023 (Weldon Cooper Center; WAVY).
- Redfin search data for spring 2026 shows 73% of Chesapeake home searchers staying within the metro, with Washington, DC, New York and Chicago the top outside sources.
History & Heritage
- Chesapeake was created on January 1, 1963, when the city of South Norfolk and Norfolk County consolidated, and voters chose the new name.
- Norfolk County was formed in 1691, when Lower Norfolk County was split in two.
- South Norfolk was incorporated as a town in 1919 and became an independent city in 1922.
- The village of Great Bridge was established in 1729 along the Great Road.
- The Battle of Great Bridge on December 9, 1775 lasted about 25 minutes and effectively ended British colonial government in Virginia.
- The Great Bridge battlefield covers 130 acres on both sides of the Albemarle and Chesapeake Canal and joined the National Register in 1973.
- The battlefield park spans four quadrants around Battlefield Boulevard and the canal.
- The Great Bridge Battlefield & Waterways Museum opened in June 2020 with eight galleries, including a life-sized re-creation of the original causeway.
- The 22-mile Dismal Swamp Canal, dug by hand from 1793 to 1805 largely by enslaved laborers, is the oldest continually operating man-made canal in the United States.
- George Washington and others founded the Dismal Swamp Company in 1763 to drain the swamp, and the company later turned to timber.
- The Albemarle and Chesapeake Canal was built from 1856 to 1860 to link the Chesapeake Bay with Albemarle Sound, and its Virginia section runs 8.5 miles.
- Deep Creek was an 18th- and 19th-century stagecoach stop between Norfolk and Elizabeth City and the main shipping point for Dismal Swamp lumber.
- Chesapeake General Hospital opened on January 26, 1976.
Environmental & Geographic
- Chesapeake covers about 351 square miles, 338.5 of them land, making it Virginia's second-largest city by land area.
- Chesapeake borders Portsmouth, Norfolk, Virginia Beach and Suffolk, plus Currituck and Camden counties in North Carolina.
- The Western and Southern Branches of the Elizabeth River run through the city, and the Western Branch community takes its name from one of them.
- The Northwest River is the city's main water source and is treated by reverse osmosis, backed by a 76-mile pipeline from Lake Gaston shared with Virginia Beach.
- The Great Dismal Swamp National Wildlife Refuge covers nearly 113,000 acres across Chesapeake, Suffolk and northeastern North Carolina.
- Lake Drummond, inside the refuge, is one of only two natural freshwater lakes in Virginia.
- The Atlantic Intracoastal Waterway splits into two routes in Chesapeake, one through the Great Bridge Lock and one through the Deep Creek Lock.
- The Great Bridge Lock operates around the clock, and Great Bridge Lock Park offers a close view of boats passing through.
- The Chesapeake Arboretum on Oak Grove Road has 2 acres of gardens, 48 acres of woodland and about 3.5 miles of trails.
- First Street data on Redfin puts 44% of 23321 properties, 30% of 23320 properties and 27% of 23322 properties at risk of severe flooding over 30 years.
- First Street rates wind risk "Severe" for virtually every property in all three ZIPs, and wildfire risk "Moderate" for 89% of 23322 properties.
- Under Virginia's Chesapeake Bay rules, each Resource Protection Area includes a 100-foot buffer along the water.
Lifestyle & Culture
- Chesapeake City Park at 900 City Park Drive covers 90 acres, with a skate park, a fenced dog park and the Robert "G" Bagley Stage.
- The Chesapeake Jubilee began in 1983 as the city's 20th birthday party, and the 2026 edition ran May 14-17 with a Saturday fireworks show.
- The Chesapeake Farmers' Market meets at City Park on Wednesdays and Saturdays through late November.
- Greenbrier Mall opened in October 1981 at 1401 Greenbrier Parkway with nearly 900,000 square feet.
- Chesapeake Square in Western Branch opened in 1989, and its redevelopment adds a grocery store and a sporting goods store on former department store sites.
- Summit Pointe on Volvo Parkway is a $330 million, 69-acre mixed-use project planned for more than 1,400 residences at build-out.
- The Dismal Swamp Canal Trail is an 8.6-mile paved trail along the canal and part of the East Coast Greenway.
- Northwest River Park covers 763 acres, with 72 campsites, rental cabins and an 18-hole disc golf course.
- Western Branch Park at 4437 Portsmouth Boulevard covers 93 acres, with lighted fields, tennis and pickleball courts and a 2-mile trail.
- The Chesapeake Central Library at 298 Cedar Road includes a public law library and a local history room.
- Chesapeake's Indian River Park covers 90 acres of urban forest, with a BMX and mountain bike trail.
Infrastructure & Access
- Chesapeake is served by I-64, I-464 and I-664, US 13, 17, 58 and 460, and the Chesapeake Expressway (Route 168).
- Tolls in Chesapeake are limited to the Chesapeake Expressway, the Veterans Bridge and the Jordan Bridge, plus the I-64 express lanes.
- Since May 1, 2026, the Chesapeake Expressway toll for a car is $4, rising to $10 on peak weekends.
- The Veterans Bridge carries Dominion Boulevard (US 17) over the Southern Branch with 95 feet of clearance; it opened in 2014 and replaced the 1962 Steel Bridge.
- The new High Rise Bridge on I-64, a 1.2-mile fixed span with 100 feet of clearance, opened to westbound traffic in July 2022.
- I-64 express lanes between Bowers Hill and I-464 opened in February 2024 with dynamic E-ZPass tolling.
- I-664 runs north through the center of Western Branch to the Monitor-Merrimac Memorial Bridge-Tunnel.
- The South Norfolk Jordan Bridge, opened in 2012, links Chesapeake and Portsmouth with all-electronic tolls.
- The city maintains about 90 bridges and overpasses, including five movable spans that open roughly 30,000 times a year.
- The mean commute for Chesapeake residents is 25.8 minutes (ACS 2020-2024).
- Chesapeake Regional Airport, a general aviation field, sits just south of Great Bridge.
Schools & Education
- Chesapeake Public Schools enrolled 40,364 students in 2025-26 across 48 schools and centers.
- The division's seven high schools are Deep Creek, Grassfield, Great Bridge, Hickory, Indian River, Oscar Smith and Western Branch.
- Great Bridge High (301 West Hanbury Road) and Hickory High (1996 Hawk Boulevard) both have 23322 addresses.
- Oscar F. Smith High moved to its campus at 1994 Tiger Drive in 23320 in 1994 and has offered the IB Diploma Program since 2003.
- Western Branch High School is at 1968 Bruin Place in 23321.
- The division offers four high school academies, the Chesapeake Career Center for grades 10-12 and the SmithTech Computer Science Lab School.
- Public schools in 23321 include Chittum Elementary, Western Branch Primary, Intermediate and Middle, and Jolliff Middle.
- Public schools in 23320 include Greenbrier Primary, Intermediate and Middle, Crestwood Elementary and Middle, and B.M. Williams Elementary.
- Tidewater Community College's Chesapeake Campus at 1428 Cedar Road covers 69 acres and houses the Regional Automotive Center.
Land, Development & Zoning
- Chesapeake's adopted long-range plan is Moving Forward Chesapeake 2035, and an update looking to 2045 has been underway since 2023.
- The city's planning director has projected about 300,000 residents by 2045.
- The Greenbrier area plan covers about 12 square miles with more than 35,000 residents and nearly 50,000 daytime workers.
- The Greenbrier plan aims to concentrate growth there to ease pressure on rural southern Chesapeake and introduces a transfer of development rights program.
- Chesapeake has adopted area plans for South Norfolk, Indian River and the Industrial Waterfront, with a Western Branch plan in the works.
- Chesapeake Square sits on 82.61 acres at I-664 and Portsmouth Boulevard, zoned B-4.
- Hickory began as a rural farming area near the North Carolina line, and suburban neighborhoods have since been built among its farms.
Demographics
- Chesapeake had an estimated 255,332 residents in July 2025, up from 249,422 at the 2020 Census.
- There are 93,626 households in Chesapeake, averaging 2.65 people each (ACS 2020-2024).
- Median household income in Chesapeake is $95,373, and per capita income is $44,985 (ACS 2020-2024).
- 36.9% of Chesapeake's adult residents hold a bachelor's degree or higher (ACS 2020-2024).
- 92.6% of Chesapeake households have broadband, and 96.3% have a computer (ACS 2020-2024).
- Chesapeake had about 737 people per square mile in 2020.
- At the 2020 Census, 23322 had 66,994 residents, 23320 had 60,412 and 23321 had 37,752.
- Weldon Cooper Center projections put Chesapeake at 277,475 residents in 2030 and 297,274 in 2040.
Investment & Value
- 74.4% of Chesapeake homes are owner-occupied (ACS 2020-2024).
- Chesapeake's largest employers include the city schools, the city, Amazon, Chesapeake General Hospital, Walmart, USAA and Dollar Tree (Virginia Works, Q3 2025).
- Chesapeake had 107,134 covered jobs in the third quarter of 2025 (Virginia Works).
- Chesapeake's unemployment rate was 3.2% in September 2025, below Virginia's 3.4% and the national 4.3%.
- Dollar Tree's corporate headquarters is at 500 Volvo Parkway in 23320.
- The Navy's NALF Fentress, east of Great Bridge, and its Northwest Annex in the Hickory area are both in Chesapeake.
- Median household income in 23322 is $134,880, according to ACS 2020-2024 ZIP estimates.
Hyper-Local Detail
- Greenbrier is made up of Greenbrier East and Greenbrier West, with Greenbrier Parkway as its commercial hub and Volvo Parkway in 23320.
- River Walk streets such as Loch Island Drive, River Strand and Marsh Island Drive carry the 23320 ZIP.
- Butts Station Road and the Chesapeake Arboretum on Oak Grove Road are in 23320.
- Stonebridge Landing streets such as Bellechase Court and Millgrove Court are in 23321.
- Taylor Road and Portsmouth Boulevard addresses in Western Branch are 23321, including Chesapeake Square at 4200 Portsmouth Boulevard.
- Edinburgh (Scone Castle Loop) and Etheridge Lakes (Sarasota Arch, Woodcott Drive) are in 23322.
- Great Bridge neighborhood addresses are mostly 23322, with some on the 23323 side.
- Great Bridge Lock Park at 100 Locks Road and Northwest River Park at 1733 Indian Creek Road are both in 23322.
- Indian River (23325), South Norfolk (23324) and Grassfield and Deep Creek (23323) fall outside the three ZIPs featured here.
Why Michael
Where Michael Adds Value in Chesapeake
Three ZIPs, three price points
Great Bridge's 23322 posted a $598,000 median in Redfin's latest figures, while Greenbrier's 23320 ran near $382,000. He prices against the right comparison.
Tolls in the monthly budget
A daily drive over the Veterans Bridge or down the Chesapeake Expressway carries tolls. He adds the commute cost before you choose a street.
Rural parcels read carefully
Hickory grew from farmland, so lot sizes and permitted uses vary widely. He checks what each parcel allows before you commit.
Offers built for a fast market
With 38% of Chesapeake homes selling above asking, he structures terms that compete without giving away protections.
FAQ
Chesapeake Questions From Buyers and Sellers
Does Michael Freeman work in Chesapeake?
Yes. Michael focuses heavily on Great Bridge and Hickory, and he also works Greenbrier and Western Branch, covering ZIPs 23320, 23321 and 23322.
Which ZIP code is Great Bridge in?
Great Bridge and Hickory are mostly 23322, with some Great Bridge addresses in 23323. Greenbrier is 23320, Western Branch is 23321 and South Norfolk is 23324.
What is Chesapeake's real estate tax rate?
The rate was $1.01 per $100 of assessed value as of July 2025. On a $400,000 assessment that is about $4,040 a year. Michael confirms the current rate and due dates with the city before closing.
Will I pay tolls commuting from Chesapeake?
It depends on the route. The Chesapeake Expressway charges $4 for a car, or $10 on peak weekends, and the Veterans Bridge on Dominion Boulevard and the Jordan Bridge are also tolled. The I-64 express lanes use dynamic E-ZPass pricing, while the regular I-64 lanes are free.
How much flood risk comes with a Chesapeake home?
It varies by ZIP. First Street data on Redfin puts 44% of 23321 properties, 30% of 23320 properties and 27% of 23322 properties at risk of severe flooding over 30 years. Michael checks the flood zone and any Resource Protection Area buffer for each home.
How quickly are Chesapeake homes selling?
Quickly. Citywide, homes sold in a median of 28 days for the three months ending August 2026, at 100.2% of list price, and 38.2% sold above asking.
Take the Next Step in the Authority Center
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