New
$510,000Hanbury Farms
832 Woodrow Ct
Chesapeake, VA 23322
3 bd2 ba1,660 sqft
Listing courtesy of David Wilkey · BHHS RW Towne RealtyREIN MLS #10653661
Homes for Sale in Chesapeake, VA: $500,000 to $750,000
269 homes for sale in Chesapeake, VA from $500,000 to $750,000, plus 7 lots, from REIN MLS · Listing data as of Sep 16, 2:10 PM ET (syncs every 2 minutes)
269 homes and 7 lots are for sale in Chesapeake from $500,000 to $750,000 today, at a median list price of $609,950. The typical home has 4 bedrooms and about 2,600 sq ft, and was built in 2014.
Tom & Dariya Milan, RealtorsBrokered by LPT Realty · Call or text (757) 777-7577
- For sale now276
- Median list price$609,950
- New this week34
- Median days on market (REIN, active listings)25 days
Source: REIN MLS. These figures include lots and exclude homes under contract.
269 Chesapeake homes and 7 lots for sale in this price range right now
(+170 under contract)Skip the 60 listingsSkip to this week's listings
NewOpen Sat 10 AM–12 PM$549,900Miars Farm3421 Anita Cir
Chesapeake, VA 23321
4 bd3.1 ba2,510 sqft
Listing courtesy of Angela Kennedy · 1st Class Real Estate IntegrityREIN MLS #10653856
New$675,000Vance Level613 McRowland Way
Chesapeake, VA 23320
3 bd3.1 ba2,500 sqft
Listing courtesy of Christine Burgdorf · Creed RealtyREIN MLS #10653795
New$725,000Dove Acres429 Warrick Rd
Chesapeake, VA 23322
5 bd4 ba3,159 sqft
Listing courtesy of Micah Laurendeau · Real Broker LLCREIN MLS #10653705
New$524,900Chapel Hill Estates1221 Rosebud Ln
Chesapeake, VA 23322
4 bd2.1 ba2,068 sqft
Listing courtesy of Steve Marable · Iron Valley Real Estate HRREIN MLS #10653645
New$624,900316 Janes Way
Chesapeake, VA 23320
4 bd2.1 ba2,772 sqft
Listing courtesy of Stacy Potts · Focus Realty LLCREIN MLS #10653639
New$585,000Western Branch Reserve3303 Arboretum Trl
Chesapeake, VA 23321
4 bd3 ba2,557 sqft
Listing courtesy of Gary Layne · Proactive Real Estate ServicesREIN MLS #10653614
New$535,000Pines Of Warrick424 Pines of Warrick Dr
Chesapeake, VA 23322
4 bd2.1 ba2,366 sqft
Listing courtesy of Laura Daugherty · Own Real Estate LLCREIN MLS #10653596
NewOpen Sat 12–2 PM$549,900Culpepper Landing3240 Conservancy Dr
Chesapeake, VA 23323
4 bd3 ba2,375 sqft
Listing courtesy of Steve Marable · Iron Valley Real Estate HRREIN MLS #10653411
New$599,900Jolliff Woods1530 Jolliff Rd
Chesapeake, VA 23321
4 bd2.1 ba2,320 sqft
Listing courtesy of Frank Trygar · BHHS RW Towne RealtyREIN MLS #10653544
Lot / landNew$675,00042.4 Acres Benefit Rd
Chesapeake, VA 23322
Listing courtesy of Walter Graham · MOP Land and Farms RealtyREIN MLS #10653549
New$525,900Legacy 168905 Bernard Lane
Chesapeake, VA 23322
4 bd3.1 ba2,200 sqft
Listing courtesy of Monique Darling · BHHS RW Towne RealtyREIN MLS #10653474
New$570,000Jolliff Landing At Western Branch5004 Cape May Loop
Chesapeake, VA 23321
4 bd2.1 ba2,468 sqft
Listing courtesy of Kathy Nelms · Corinth Realty LLCREIN MLS #10653514
New$575,000Forest Cove1201 Richwood Ave
Chesapeake, VA 23323
5 bd3 ba2,412 sqft
Listing courtesy of Eric Sessions · Fathom RealtyREIN MLS #10653391
NewOpen Sat 1–3 PM$639,900Parkview2065 Shipyard Rd
Chesapeake, VA 23323
4 bd2.1 ba2,652 sqft
Listing courtesy of Julian Rivera · Iron Valley Real Est NorfolkREIN MLS #10653324
NewOpen Sat 12–2 PM$680,000Dock Landing1529 Lauren Ashleigh Dr
Chesapeake, VA 23321
4 bd3 ba3,629 sqft
Listing courtesy of Sara Dunbar · Redfin CorporationREIN MLS #10652980
New$725,000Cheshire Forest813 Satinwood Ct
Chesapeake, VA 23322
5 bd3.1 ba3,100 sqft
Listing courtesy of Diane Keeley · BHHS RW Towne RealtyREIN MLS #10652854
New$685,000Dominion Meadows952 Checkerspot Way
Chesapeake, VA 23323
5 bd2.1 ba2,954 sqft
Listing courtesy of Annalisa Previte · Howard Hanna Real Estate Svcs.REIN MLS #10652920
New$539,900School House Crossing1505 Hilltop Dr
Chesapeake, VA 23322
4 bd2.1 ba2,020 sqft
Listing courtesy of Karen Harper · The Real Estate GroupREIN MLS #10653218
New$559,900Legacy 168906 Bernard Ln
Chesapeake, VA 23322
3 bd3.1 ba2,228 sqft
Listing courtesy of Nicholas Borrajo · Iron Valley Real Estate HRREIN MLS #10653230
New$719,900Cheshire Forest804 Wakedale Arch
Chesapeake, VA 23322
5 bd4 ba3,720 sqft
Listing courtesy of Jeff Babb · AtCoastal RealtyREIN MLS #10653264
New$665,000Las Gaviotas419 Granada Dr
Chesapeake, VA 23322
4 bd3 ba3,371 sqft
Listing courtesy of Stephanie Hynes · Redefy Real EstateREIN MLS #10652967
New$650,0002722 Gum Rd
Chesapeake, VA 23321
5 bd3 ba3,112 sqft
Listing courtesy of Roberto Gonzalez · Real Broker LLCREIN MLS #10653164
New$509,900Homestead At Bowers Hill508 Schaefer Ave
Chesapeake, VA 23321
4 bd2.1 ba2,398 sqft
Listing courtesy of Sonali Hutson · Samson PropertiesREIN MLS #10653139
New$650,000Deep Creek2100 Millville Rd
Chesapeake, VA 23323
5 bd2.1 ba2,714 sqft
Listing courtesy of Heidi Oglesby · The Real Estate GroupREIN MLS #10652716
New$540,000Miars Farm3405 Anita Cir
Chesapeake, VA 23321
5 bd3.1 ba3,164 sqft
Listing courtesy of Katherine Robertson · Own Real Estate LLCREIN MLS #10652858
New$545,000Hickory716 Tallahassee Dr
Chesapeake, VA 23322
4 bd2.1 ba2,340 sqft
Listing courtesy of Karen Powell · Iron Valley Real Estate HRREIN MLS #10652777
NewOpen Sat 1–3 PM$599,900712 Appalachian Court Ct
Chesapeake, VA 23320
4 bd2.1 ba2,389 sqft
Listing courtesy of James Griffin · United Atlantic RealtyREIN MLS #10652632
New$575,000Hulen Estates412 Harper Ct
Chesapeake, VA 23323
5 bd3.1 ba2,853 sqft
Listing courtesy of Melissa L'Hoste · Keller Williams Realty Twn CtrREIN MLS #10653159
NewOpen Sat 10 AM–12 PM$747,995Etheridge Lakes1052 Stockleybridge Dr
Chesapeake, VA 23322
5 bd3 ba3,126 sqft
Listing courtesy of Rachael Turner · GreenTree Realty IncREIN MLS #10651967
NewOpen Sat 1–4 PM$595,900Legacy 168904 Koonce Ln
Chesapeake, VA 23322
3 bd3.1 ba2,500 sqft
Listing courtesy of Monique Darling · BHHS RW Towne RealtyREIN MLS #10652999
New$629,000Hunningdon Lakes1104 Copper Stone Circle Cir
Chesapeake, VA 23320
4 bd3 ba2,900 sqft
Listing courtesy of Carlos Cardo · RE/MAX UltraREIN MLS #10652961
NewOpen Sat 1–4 PM$539,900Legacy 168900 Jennings Ln
Chesapeake, VA 23322
3 bd3.1 ba2,200 sqft
Listing courtesy of Monique Darling · BHHS RW Towne RealtyREIN MLS #10652945
NewPrice reduced$522,500Las Gaviotaswas
$525,000400 Las Gaviotas Blvd
Chesapeake, VA 23322
4 bd2.1 ba2,200 sqft
Listing courtesy of Joseph Igana · Iron Valley Real Est NorfolkREIN MLS #10652912
NewOpen Sat 11 AM–1 PM$715,000Emerald Lakes812 Brookside Arch
Chesapeake, VA 23322
4 bd3 ba3,058 sqft
Listing courtesy of Charles Evans · Iron Valley Real Estate PrestigeREIN MLS #10652738
Coming Soon$619,000New Mill Landing311 Lancing Way
Chesapeake, VA 23323
4 bd2.1 ba2,515 sqft
Listing courtesy of Jackie Tan · Bowman RealtyREIN MLS #10652797
New$749,000Great Bridge909 Brice Ct
Chesapeake, VA 23322
6 bd3 ba3,525 sqft
Listing courtesy of Kelly DiPasquale · Aweigh Real EstateREIN MLS #10652745
New$695,000Riverview LandingMm Madison 2
Chesapeake, VA 23322
4 bd3 ba2,552 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10652779
New$629,999Fieldstone1808 Ashlar Ln
Chesapeake, VA 23320
4 bd2.1 ba2,559 sqft
Listing courtesy of Tammy Bunch · Bunch Real Estate Inc.REIN MLS #10652753
$608,900Josephs Meadows213 Maggie Bell Ln.
Chesapeake, VA 23320
3 bd2.1 ba2,500 sqft
Listing courtesy of Monique Darling · BHHS RW Towne RealtyREIN MLS #10652577
New$719,810Crestfield At Centerville2052 Charwood Dr
Chesapeake, VA 23320
4 bd3.1 ba2,803 sqft
Listing courtesy of Morgan Xenos · Dragas Companies Realty IncREIN MLS #10652698
New$565,000Cheshire Forest641 Edgewood Arch
Chesapeake, VA 23322
4 bd3.1 ba2,264 sqft
Listing courtesy of Faith Mormon · BHHS RW Towne RealtyREIN MLS #10652602
New$549,000Green Meadow Point2708 Meadow Dr W
Chesapeake, VA 23321
5 bd2.1 ba2,242 sqft
Listing courtesy of Melinda Baldwin · CENTURY 21 Nachman RealtyREIN MLS #10652573
$735,000Haven At Centerville1836 Bancroft Rd
Chesapeake, VA 23320
3 bd2 ba2,600 sqft
Listing courtesy of Laura McGuire · VA Realty ProfessionalsREIN MLS #10652410
$749,000Great Bridge905 Washington Dr
Chesapeake, VA 23322
5 bd2.1 ba3,600 sqft
Listing courtesy of Annie Culver Bird · BHHS RW Towne RealtyREIN MLS #10652400
$593,000Millers Run3404 Louise James Ct
Chesapeake, VA 23323
5 bd2.1 ba3,100 sqft
Listing courtesy of Patrick Istilart · 1st Advantage Realty LLCREIN MLS #10652067
Price reducedOpen Sat 1–3 PM$549,900Sawyers Millwas
$560,0002809 Cistern Cir
Chesapeake, VA 23323
4 bd2.1 ba2,384 sqft
Listing courtesy of Bethany White · BHHS RW Towne RealtyREIN MLS #10651217
$619,000Cedarwood228 Country Club Blvd
Chesapeake, VA 23322
4 bd2.1 ba3,086 sqft
Listing courtesy of Janice Hollowell · World Class RealtyREIN MLS #10652285
$703,705Crestfield At Centerville2037 Charwood Dr
Chesapeake, VA 23320
4 bd3.1 ba2,803 sqft
Listing courtesy of Morgan Xenos · Dragas Companies Realty IncREIN MLS #10652119
Open Sun 1–3 PM$639,000Great Bridge568 Waters Rd
Chesapeake, VA 23322
6 bd2.1 ba3,369 sqft
Listing courtesy of David Johnson · Howard Hanna Real Estate Svcs.REIN MLS #10652034
$599,900Upton Farms841 Woodstream Way
Chesapeake, VA 23322
4 bd2.1 ba2,434 sqft
Listing courtesy of Robyn Slocum · Iron Valley Real Estate HRREIN MLS #10650869
$565,900Jolliff Landing At Western BranchMm Carter (5 Bed)
Chesapeake, VA 23321
5 bd4 ba2,441 sqft
Listing courtesy of Kathy Nelms · Corinth Realty LLCREIN MLS #10652084
$550,000Las Gaviotas309 Barcelona Dr
Chesapeake, VA 23320
4 bd3 ba2,485 sqft
Listing courtesy of Katie Verhalen · Judy Reed RealtyREIN MLS #10651803
$589,500Hillcrest620 Ambrose St
Chesapeake, VA 23322
4 bd2.1 ba2,300 sqft
Listing courtesy of Deborah Rountree · BHHS RW Towne RealtyREIN MLS #10651843
Price reduced$554,900Riverview At The Preservewas
$574,900152 Tranquility Trce
Chesapeake, VA 23320
4 bd3 ba2,677 sqft
Listing courtesy of Jean Bowman · Bowman RealtyREIN MLS #10651714
$539,900Oakbrooke Meadows903 Willow Brook Ct
Chesapeake, VA 23320
4 bd2.1 ba2,746 sqft
Listing courtesy of Ann Davis · BHHS RW Towne RealtyREIN MLS #10651539
$540,000Homemont917 Erie St
Chesapeake, VA 23322
4 bd3.1 ba2,200 sqft
Listing courtesy of Debra Digges · Howard Hanna Real Estate Svcs.REIN MLS #10650841
$525,000Jolliff Landing At Western Branch5000 Corolla Dr
Chesapeake, VA 23321
4 bd2 ba2,183 sqft
Listing courtesy of Hannah Arnold · BHHS RW Towne RealtyREIN MLS #10651289
$615,000Hickory Manor1924 Bexley Ln
Chesapeake, VA 23322
4 bd2.1 ba2,632 sqft
Listing courtesy of Jennifer Peeples · Thrive RealtyREIN MLS #10651444
$534,900Bayberry Place1629 Waterside Dr
Chesapeake, VA 23320
4 bd2.1 ba2,400 sqft
Listing courtesy of Laura Blackwood · SerhantREIN MLS #10651368
Showing 1–60 of 446
Homes for sale are listed first, newest listings first; homes under contract follow.
Changes daily
Price cuts and open houses this week: Chesapeake homes from $500,000 to $750,000
Price reduced (105)
105 of 276 listings for sale have had a price cut.
Price reduced$725,000Hickorywas
$775,000112 Station Rd
Chesapeake, VA 23322
5 bd2.1 ba4,200 sqft
Listing courtesy of Alexandra Serrano · The Real Estate GroupREIN MLS #10642786
Price reduced$524,500Culpepper Landingwas
$550,0003209 Dodd Dr
Chesapeake, VA 23323
4 bd3 ba2,380 sqft
Listing courtesy of Barbara Glover · CENTURY 21 Top ProducersREIN MLS #10644867
Price reduced$520,000Jolliff Woodswas
$540,0004936 Oriole Dr
Chesapeake, VA 23321
4 bd2.1 ba2,378 sqft
Listing courtesy of Judy Reed · Judy Reed RealtyREIN MLS #10647434
Price reduced$675,000Olahs Landing At Great Bridgewas
$700,0001125 George Olah Dr
Chesapeake, VA 23322
5 bd3 ba2,900 sqft
Listing courtesy of George Trotman · BHHS RW Towne RealtyREIN MLS #10650782
Price reduced$699,990Patriots Ridgewas
$724,9901520 Jimmy Ln
Chesapeake, VA 23322
5 bd3 ba3,010 sqft
Listing courtesy of Jenny Lovell · BHHS RW Towne RealtyREIN MLS #10651102
Price reduced$725,000Bayberry Placewas
$750,0001548 Waterside Dr N
Chesapeake, VA 23320
6 bd3.1 ba4,811 sqft
Listing courtesy of Rhonda Shelton · BHHS RW Towne RealtyREIN MLS #10646118
Open houses this week (36)
61 open house sessions at 36 listings, Sep 16–23.
Price reducedOpen Sat 10 AM–1 PM$575,000Waterstonewas
$585,0002004 Acentala Quay
Chesapeake, VA 23321
5 bd3.1 ba3,076 sqft
Listing courtesy of Betsy Thompson · The AgencyREIN MLS #10648854
Price reducedOpen Sat 11 AM–2 PM$724,900Arlington Meadowswas
$729,9001328 Waycroft Rch
Chesapeake, VA 23320
4 bd3.1 ba3,371 sqft
Listing courtesy of Ronald Sawyer · RE/MAX PrimeREIN MLS #10648559
Open Sat 11 AM–2 PM$625,000Etheridge Lakes1805 Crestwynd Dr
Chesapeake, VA 23322
4 bd2.1 ba2,544 sqft
Listing courtesy of Fran Barbaree · Long & Foster Real Estate Inc.REIN MLS #10647389
Open Sat 12–2 PM$688,900Warrington Hall816 Poquoson Xing
Chesapeake, VA 23320
5 bd3 ba3,650 sqft
Listing courtesy of Francheska Ferguson · The Real Estate GroupREIN MLS #10650242
Price reducedOpen Sat 12–2 PM$534,900Briarwood Meadowswas
$544,900813 Stardale Dr
Chesapeake, VA 23322
5 bd3.1 ba2,762 sqft
Listing courtesy of Woody Warren · LPT Realty LLCREIN MLS #10648220
Price reducedOpen Sat 12–2 PM$624,900Stratford Terracewas
$629,900509 Fair Oak Dr
Chesapeake, VA 23322
4 bd2.1 ba2,362 sqft
Listing courtesy of Eddie Gerardo-Ferrer · RE/MAX AllegianceREIN MLS #10647918
Price ranges
Chesapeake, VA homes for sale by price range
| Price range | Homes for sale | Typical beds | Typical size | Typical year built | Est. P&I / mo | Listings |
|---|---|---|---|---|---|---|
| Under $200K | 10+41 lots | 2 | 1,112 sqft | 1977 | Est. payment up to $1,027/mo | |
| $200K–$300K | 89+9 lots | 2 | 1,254 sqft | 1983 | Est. payment $1,284/mo | See all 98 listings → |
| $300K–$400K | 129+1 lot | 3 | 1,640 sqft | 1987 | Est. payment $1,798/mo | See all 130 listings → |
| $400K–$500K | 114+5 lots | 4 | 2,058 sqft | 2002 | Est. payment $2,311/mo | See all 119 listings → |
| $500K–$750K | 269+7 lots | 4 | 2,600 sqft | 2014 | Est. payment $3,210/mo | Shown on this page |
| Over $750K | 96+6 lots | 5 | 3,240 sqft | 2026 | Est. payment from $3,852/mo | See all 102 listings → |
Market snapshot
Chesapeake homes from $500,000 to $750,000: market snapshot, September 2026
Of the 276 listings for sale in Chesapeake from $500,000 to $750,000, 105 (38%) have had a price cut, and another 170 are under contract. The median active listing has been on the market 25 days (REIN).
For sale now
- Median price per sq ft
- $232
- Under contract
- 170
- With a price cut
- 10538% of homes for sale
Recently sold
- Homes sold
- 598
- Median sold price
- $597,250
- Median days on market (REIN)
- 18 days
- Median sold price per sq ft
- $225
Closed sales from REIN MLS, March 2026 – August 2026.
Chesapeake housing market trends →Chesapeake market report PDF →
Data: REIN MLS, September 16, 2026.
Your agents
Your Chesapeake real estate agents: Tom & Dariya Milan
Tom & Dariya Milan, Realtors
Brokered by LPT Realty
We are Tom and Dariya Milan, a husband-and-wife team of licensed real estate agents in Virginia, serving Hampton Roads since 2005. Our office is at Town Center in Virginia Beach, and we are members of REIN MLS, the listing service behind every home on this page. In Chesapeake our work takes us across Greenbrier, Great Bridge, Hickory, Deep Creek, Western Branch and South Norfolk. Call or text us about any Chesapeake home on REIN MLS, or ask for a private showing.
Office: 249 Central Park Ave Ste 300-220, Virginia Beach, VA 23462
FAQ
Homes for sale in Chesapeake, VA from $500,000 to $750,000: FAQ
How many homes are for sale in Chesapeake, VA from $500,000 to $750,000?
As of September 16, 2026, REIN MLS shows 269 homes for sale in Chesapeake from $500,000 to $750,000, plus 7 lots. Another 170 listings are under contract. Of the 276 listings for sale, 34 have been listed since September 10 and 105 have had a price cut.
What do homes from $500,000 to $750,000 in Chesapeake look like?
The median list price of the 276 listings for sale in Chesapeake from $500,000 to $750,000, 7 lots included, is $609,950 as of September 16, 2026. The typical home has 4 bedrooms and about 2,600 sq ft, and was built in 2014. The median list price per square foot is $232.
How fast do homes from $500,000 to $750,000 sell in Chesapeake?
From March 2026 through August 2026, 598 homes in Chesapeake sold from $500,000 to $750,000 on REIN MLS, at a median sold price of $597,250. The median closed sale was on the market 18 days (REIN).
More homes