No photo provided
New
$560,000Olde Mill Run
3204 Eight Star Ct
Chesapeake, VA 23323
4 bd2.1 ba2,706 sqft
Listing courtesy of Darrell Moore · CENTURY 21 Top ProducersREIN MLS #10656875
Homes for Sale in Chesapeake, VA: $500,000 to $750,000
264 homes for sale in Chesapeake, VA from $500,000 to $750,000, plus 4 lots, from REIN MLS · Listing data as of Oct 7, 3:08 PM ET (syncs every 2 minutes)
264 homes and 4 lots are for sale in Chesapeake from $500,000 to $750,000 today, at a median list price of $599,900. The typical home has 4 bedrooms and about 2,607 sq ft, and was built in 2017.
Tom & Dariya Milan, RealtorsBrokered by LPT Realty · Call or text (757) 777-7577
- For sale now268
- Median list price$599,900
- New this week36
- Median days on market (REIN, active listings)22 days
Source: REIN MLS. These figures include lots and exclude homes under contract.
264 Chesapeake homes and 4 lots for sale in this price range right now
(+189 under contract)Skip the 60 listingsSkip to this week's listings
Coming Soon$529,900Albemarle Acres408 Currituck Dr
Chesapeake, VA 23322
4 bd2.1 ba2,244 sqft
Listing courtesy of Catherine Underwood · BHHS RW Towne RealtyREIN MLS #10656729
Coming Soon$669,000920 Covenant Way
Chesapeake, VA 23322
5 bd3 ba2,912 sqft
Listing courtesy of Kimberly Burbage · Liz Moore & Associates LLCREIN MLS #10656320
New$584,999Great Bridge522 Bells Hollow Ct
Chesapeake, VA 23322
4 bd3 ba2,101 sqft
Listing courtesy of Nathan Priest · Atlantic Sothebys Int'l RealtyREIN MLS #10656702
New$563,740Retreat At Edinburgh2203 Edwin Dr
Chesapeake, VA 23322
2 bd3 ba1,986 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10656645
New$585,740Retreat At Edinburgh2226 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10656643
New$724,900Great Bridge343 Ewell Ln
Chesapeake, VA 23322
5 bd3.1 ba3,000 sqft
Listing courtesy of Denise Hawkins · Triumph Realty Group LLCREIN MLS #10656577
Coming Soon$540,000Kemp Crossing833 Kemp Meadow Dr
Chesapeake, VA 23320
4 bd2.1 ba2,572 sqft
Listing courtesy of Robert Sayoc · KW Coastal Virginia ChesapeakeREIN MLS #10654833
NewOpen Sat 1–3 PM$525,000Woodbriar1149 Crystalwood Cir
Chesapeake, VA 23320
4 bd2.1 ba2,100 sqft
Listing courtesy of Amanda Hoke · The Bryant GroupREIN MLS #10656507
NewOpen Sat 10 AM–12 PM$594,800Winston Trace513 Telfyan Dr
Chesapeake, VA 23320
5 bd2.1 ba3,300 sqft
Listing courtesy of Dean Rolle · Iron Valley Real Estate HRREIN MLS #10656498
Coming SoonOpen Sat 11 AM–2 PM$597,999Foxgate Quarter501 Spurlock Way
Chesapeake, VA 23322
4 bd3 ba2,522 sqft
Listing courtesy of Catherine Underwood · BHHS RW Towne RealtyREIN MLS #10656230
Coming SoonOpen Sat 11 AM–1 PM$569,900Tunbridge Station144 Downing Dr
Chesapeake, VA 23322
4 bd3 ba2,497 sqft
Listing courtesy of Tyler Rocke · Keller Williams Capital Props.REIN MLS #10655754
New$650,000Georgetown East440 Ivy Cres
Chesapeake, VA 23325
4 bd3.1 ba3,412 sqft
Listing courtesy of Sunshine Swinson · World Class RealtyREIN MLS #10656618
New$545,900Legacy 168901 Bernard Ln
Chesapeake, VA 23322
3 bd3.1 ba2,200 sqft
Listing courtesy of Monique Darling · BHHS RW Towne RealtyREIN MLS #10655949
Coming Soon$750,000Etheridge Lakes809 Leleon Ct
Chesapeake, VA 23322
4 bd2.2 ba3,037 sqft
Listing courtesy of Melisa Johns · EXP Realty LLCREIN MLS #10656562
Coming Soon$559,900Etheridge Woods1021 Grantham Ln
Chesapeake, VA 23322
4 bd2 ba2,332 sqft
Listing courtesy of Robin Gauthier · NextHome Tidewater RealtyREIN MLS #10656531
New$585,740Retreat At Edinburgh2224 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10656534
New$585,740Retreat At Edinburgh2222 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10656532
Coming Soon$675,000Cheshire Forest516 Ashforth Way Way
Chesapeake, VA 23322
5 bd3.1 ba3,297 sqft
Listing courtesy of Jaima Botterbush · Iron Valley Real Estate HRREIN MLS #10656044
New$625,000Wilson Heights233 Old Dr
Chesapeake, VA 23322
5 bd2.1 ba2,200 sqft
Listing courtesy of Taylor Dirk · Iron Valley Real Estate PrestigeREIN MLS #10656430
New$610,000Hickory Manor1910 Briton Ln
Chesapeake, VA 23322
4 bd2.1 ba2,598 sqft
Listing courtesy of Kelvin Reed · Reeds Real Estate LLCREIN MLS #10656415
New$624,990Dominion Lakes1237 Spruce Ln
Chesapeake, VA 23320
4 bd2.1 ba2,850 sqft
Listing courtesy of Angela Hebert · G Daniels & CompanyREIN MLS #10656376
New$604,900Jordan Hall @ Johnstown525 Hanbury Rd W
Chesapeake, VA 23322
4 bd2.1 ba2,388 sqft
Listing courtesy of Tamara Orlando · Own Real Estate LLCREIN MLS #10656333
New$729,740Riverview Landing925 Intracoastal Way
Chesapeake, VA 23322
4 bd3 ba2,748 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10656327
New$695,000Cheshire Forest801 Keeling Dr
Chesapeake, VA 23322
4 bd3.1 ba3,169 sqft
Listing courtesy of Adrielle Roxas · LPT Realty LLCREIN MLS #10656163
New$524,900Deep Creek317 George Washington Hwy S
Chesapeake, VA 23323
3 bd2 ba1,869 sqft
Listing courtesy of Allison Samson · Broadsight RealtyREIN MLS #10655769
Coming Soon$675,000Eagle Lake Plantation North1500 Coker Pl
Chesapeake, VA 23320
5 bd2.1 ba3,329 sqft
Listing courtesy of Dayla Brooks · Own Real Estate LLCREIN MLS #10656054
NewOpen Sun 12–2 PM$575,000Las Gaviotas423 Las Gaviotas Blvd
Chesapeake, VA 23322
4 bd3 ba2,585 sqft
Listing courtesy of Kelly Liedtke · AMW Real Estate IncREIN MLS #10656015
New$565,000The Crossings4308 Galston Ct
Chesapeake, VA 23321
5 bd2.1 ba2,753 sqft
Listing courtesy of Adam Jeter · The Real Estate GroupREIN MLS #10654907
New$585,740Retreat At Edinburgh2220 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10656034
New$640,000Hanbury Manor1103 Madison Lynn Way
Chesapeake, VA 23322
5 bd2.1 ba2,557 sqft
Listing courtesy of Racheal Pridgen · Keller Williams Town CenterREIN MLS #10655665
New$655,000Legacy 168200 Traditions Way
Chesapeake, VA 23322
3 bd3.1 ba2,500 sqft
Listing courtesy of Monique Darling · BHHS RW Towne RealtyREIN MLS #10655918
NewOpen Sun 11 AM–1:30 PM$749,000Emerald Lakes1204 Lingale Ct
Chesapeake, VA 23322
5 bd3 ba3,200 sqft
Listing courtesy of Kristie Weaver · SerhantREIN MLS #10655942
New$715,000Coopers Creek Manor145 Sinclair Ln
Chesapeake, VA 23322
5 bd3 ba3,436 sqft
Listing courtesy of Jamie Potts · Focus Realty LLCREIN MLS #10655793
New$679,5801004 Cedar Tree Ct
Chesapeake, VA 23323
4 bd3 ba3,054 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10655160
New$700,000Wexford Square1313 Parkdale St
Chesapeake, VA 23322
4 bd3 ba2,807 sqft
Listing courtesy of Nicole Piette · BHHS RW Towne RealtyREIN MLS #10653628
New$684,8241011 Cedar Tree Ct
Chesapeake, VA 23323
4 bd2.1 ba2,632 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10655903
New$559,900Etheridge Manor811 Bellingham Dr
Chesapeake, VA 23322
3 bd2 ba1,612 sqft
Listing courtesy of Ronald Sawyer · RE/MAX PrimeREIN MLS #10655745
New$699,990Patriots Ridge205 Gertrude St
Chesapeake, VA 23322
5 bd3 ba3,010 sqft
Listing courtesy of Jenny Lovell · BHHS RW Towne RealtyREIN MLS #10655662
$610,000Olde Mill Run3240 Joplin Ln
Chesapeake, VA 23323
5 bd3.1 ba3,200 sqft
Listing courtesy of Angela Oliver · BHHS RW Towne RealtyREIN MLS #10655526
$597,740Retreat At Edinburgh2207 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655508
$720,000Riverview LandingMm James 2
Chesapeake, VA 23322
5 bd3 ba2,691 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10655465
$709,990Patriots Ridge204 Henry Jefferson Way
Chesapeake, VA 23322
4 bd3 ba2,787 sqft
Listing courtesy of Jenny Lovell · BHHS RW Towne RealtyREIN MLS #10655470
$564,900Jolliff Landing At Western Branch5103 Annapolis Dr
Chesapeake, VA 23321
4 bd3 ba2,515 sqft
Listing courtesy of Christina Bryant Pierre · Pierre & Associates RealtyREIN MLS #10655464
$629,0001703 Cheslie Arch
Chesapeake, VA 23323
4 bd2.1 ba2,506 sqft
Listing courtesy of Bridgette Pugh · NextHome Tidewater RealtyREIN MLS #10654343
$550,000Silverwood3240 Morningside Dr
Chesapeake, VA 23321
3 bd2.1 ba3,200 sqft
Listing courtesy of Lisa McCreight · The Real Estate GroupREIN MLS #10655418
$629,900Oak Ridge1345 Oak Ridge Dr
Chesapeake, VA 23322
4 bd2 ba1,839 sqft
Listing courtesy of Sarah Carr · Iron Valley Real Est NorfolkREIN MLS #10655393
$545,000Hickory716 Tallahassee Dr
Chesapeake, VA 23322
4 bd2.1 ba2,340 sqft
Listing courtesy of Karen Powell · BHHS RW Towne RealtyREIN MLS #10655350
$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 #10655291
$649,900Hall Heights101 Stadium Dr
Chesapeake, VA 23322
4 bd3.1 ba3,458 sqft
Listing courtesy of Andree Angelescu · World Class RealtyREIN MLS #10655286
$609,000Great Bridge441 Chandler Dr
Chesapeake, VA 23322
5 bd3 ba2,930 sqft
Listing courtesy of Ronna Thomas-Worthington · World Class RealtyREIN MLS #10655211
$577,740Retreat At Edinburgh2156 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655240
$597,740Retreat At Edinburgh2180 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655238
$597,740Retreat At Edinburgh2184 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655236
$597,740Retreat At Edinburgh2182 Edwin Dr
Chesapeake, VA 23322
3 bd3 ba2,642 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655235
$529,000South Norfolk911 Bainbridge Blvd
Chesapeake, VA 23324
4 bd3 ba2,176 sqft
Listing courtesy of Laura Rowe · BHHS RW Towne RealtyREIN MLS #10655168
$705,000Riverwalk708 Pebble Quay
Chesapeake, VA 23320
4 bd3 ba3,745 sqft
Listing courtesy of Molly Randall · Live Oak Real EstateREIN MLS #10655182
$550,000Etheridge Woods1013 Baydon Ln
Chesapeake, VA 23322
4 bd2.1 ba2,234 sqft
Listing courtesy of Kathryn Sharpe · Howard Hanna Real Estate Svcs.REIN MLS #10654935
$515,000Waterford974 N Haven Cir
Chesapeake, VA 23322
4 bd2 ba1,470 sqft
Listing courtesy of Chelsea Axelrod · A Better Way Realty Inc.REIN MLS #10654763
$649,900Jolliff Landing At Western Branch2217 Nantucket Ave
Chesapeake, VA 23321
4 bd2.1 ba2,913 sqft
Listing courtesy of Kathy Nelms · Corinth Realty LLCREIN MLS #10655107
Showing 1–60 of 457
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 (91)
91 of 268 listings for sale have had a price cut.
Price reduced$549,900Green Meadow Pointwas
$574,9002800 Meadow Wood Dr E
Chesapeake, VA 23321
4 bd2.1 ba2,235 sqft
Listing courtesy of Drew Little · Real Broker LLCREIN MLS #10647633
Price reduced$650,000was
$675,0001617 Banff Ct
Chesapeake, VA 23320
5 bd2.1 ba3,490 sqft
Listing courtesy of Betsy Thompson · The AgencyREIN MLS #10649105
Price reduced$725,000Fernwood Shoreswas
$750,000245 Fernwood Farms Rd
Chesapeake, VA 23320
6 bd3 ba4,396 sqft
Listing courtesy of Perdethia Lowery · CENTURY 21 Top ProducersREIN MLS #10646538
Price reducedOpen Thu 5:30–7 PM$615,000Parkviewwas
$635,0002065 Shipyard Rd
Chesapeake, VA 23323
4 bd3.1 ba2,652 sqft
Listing courtesy of Julian Rivera · Iron Valley Real Est NorfolkREIN MLS #10653324
Price reduced$619,000Great Bridgewas
$639,000568 Waters Rd
Chesapeake, VA 23322
6 bd2.1 ba3,369 sqft
Listing courtesy of David Johnson · Howard Hanna Real Estate Svcs.REIN MLS #10652034
Price reduced$725,000Etheridge Lakeswas
$747,9951052 Stockleybridge Dr
Chesapeake, VA 23322
5 bd3 ba3,126 sqft
Listing courtesy of Rachael Turner · GreenTree Realty IncREIN MLS #10651967
Open houses this week (11)
11 open house sessions at 11 listings, Oct 7–14.
Open Sun 3–5 PM$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
Price reducedOpen Thu 4:30–6:30 PM$525,000Jolliff Landing At Western Branchwas
$539,9002216 Hampton Roads Pw
Chesapeake, VA 23321
4 bd2.1 ba2,542 sqft
Listing courtesy of Taylor Lennox · Keller Williams Town CenterREIN MLS #10654089
Price reducedOpen Thu 4:30–6:30 PM$745,900Riverwalkwas
$749,900745 Seagrass Rch
Chesapeake, VA 23320
4 bd3.1 ba3,768 sqft
Listing courtesy of Janice Bullard · The Real Estate GroupREIN MLS #10649237
Open Thu 5–7 PM$675,000Vance Level613 McRowland Way
Chesapeake, VA 23320
3 bd3.1 ba2,500 sqft
Listing courtesy of Christine Burgdorf · Creed RealtyREIN MLS #10653795
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 | 12+48 lots | 2 | 960 sqft | 1978 | Est. payment up to $1,027/mo | See all 60 listings → |
| $200K–$300K | 92+12 lots | 3 | 1,240 sqft | 1980 | Est. payment $1,284/mo | See all 104 listings → |
| $300K–$400K | 139+1 lot | 3 | 1,600 sqft | 1979 | Est. payment $1,798/mo | See all 140 listings → |
| $400K–$500K | 105+5 lots | 4 | 2,038 sqft | 1997 | Est. payment $2,311/mo | See all 110 listings → |
| $500K–$750K | 264+4 lots | 4 | 2,607 sqft | 2017 | Est. payment $3,210/mo | Shown on this page |
| Over $750K | 95+6 lots | 5 | 3,233 sqft | 2026 | Est. payment from $3,852/mo | See all 101 listings → |
Market snapshot
Chesapeake homes from $500,000 to $750,000: market snapshot, October 2026
Of the 268 listings for sale in Chesapeake from $500,000 to $750,000, 91 (34%) have had a price cut, and another 189 are under contract. The median active listing has been on the market 22 days (REIN).
For sale now
- Median price per sq ft
- $232
- Under contract
- 189
- With a price cut
- 9134% of homes for sale
Recently sold
- Homes sold
- 664
- Median sold price
- $595,000
- Median days on market (REIN)
- 18 days
- Median sold price per sq ft
- $225
Closed sales from REIN MLS, March 2026 – September 2026.
Chesapeake housing market trends →Chesapeake market report PDF →
Data: REIN MLS, October 7, 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 October 7, 2026, REIN MLS shows 264 homes for sale in Chesapeake from $500,000 to $750,000, plus 4 lots. Another 189 listings are under contract. Of the 268 listings for sale, 36 have been listed since October 1 and 91 have had a price cut.
What do homes from $500,000 to $750,000 in Chesapeake look like?
The median list price of the 268 listings for sale in Chesapeake from $500,000 to $750,000, 4 lots included, is $599,900 as of October 7, 2026. The typical home has 4 bedrooms and about 2,607 sq ft, and was built in 2017. 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 September 2026, 664 homes in Chesapeake sold from $500,000 to $750,000 on REIN MLS, at a median sold price of $595,000. The median closed sale was on the market 18 days (REIN).
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