New
$859,900Sentry Estates
2517 Number Ten Ln
Chesapeake, VA 23323
4 bd3.1 ba2,941 sqft
Listing courtesy of Kate Pitre · BHHS RW Towne RealtyREIN MLS #10660465
Luxury Homes for Sale in Chesapeake, VA: $750,000 and Up
86 homes for sale in Chesapeake, VA over $750,000, plus 6 lots, from REIN MLS · Listing data as of Nov 4, 8:10 PM ET (syncs every 2 minutes)
86 homes and 6 lots are for sale in Chesapeake over $750,000 today, at a median list price of $878,070. The typical home has 4–5 bedrooms and about 3,226 sq ft, and was built in 2026.
Tom & Dariya Milan, RealtorsBrokered by LPT Realty · Call or text (757) 777-7577
- For sale now92
- Median list price$878,070
- New this week8
- Median days on market (REIN, active listings)38 days
Source: REIN MLS. These figures include lots and exclude homes under contract.
86 Chesapeake homes and 6 lots for sale in this price range right now
(+71 under contract)Skip the 60 listings
New$760,000Pleasant Grove208 Leicester CtChesapeake, VA 233225 bd3 ba4,160 sqftListing courtesy of Judy Reed · Judy Reed RealtyREIN MLS #10660322
New$850,000Hickory2924 Cedarville RdChesapeake, VA 233226 bd4 ba5,156 sqftListing courtesy of Amy Holloway · Coldwell Banker PremierREIN MLS #10659933
New$819,900Stoney Creek1322 Sebastian CtChesapeake, VA 233225 bd3.1 ba3,480 sqftListing courtesy of Heide Mahr · RE/MAX CapitalREIN MLS #10659838
New$849,900Hickory1421 Saint Brides Road WestChesapeake, VA 233224 bd3.1 ba2,720 sqftListing courtesy of Rachael Turner · GreenTree Realty IncREIN MLS #10659781
New$799,900Pleasant Grove2907 Seven Eleven RdChesapeake, VA 233224 bd2.1 ba2,400 sqftListing courtesy of Rachel Beasley · KW Allegiance ShorelineREIN MLS #10659928
New$769,740Riverview Landing321 Riverview RdChesapeake, VA 233225 bd4 ba3,165 sqftListing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10659837
New$3,650,000Hickory1004 Saint Brides Rd WChesapeake, VA 233226 bd4.1 ba5,566 sqftListing courtesy of Diana Brink · A Better Way Realty Inc.REIN MLS #10659341
$776,315Crestfield At Centerville2044 Charwood DrChesapeake, VA 233204 bd3.1 ba3,555 sqftListing courtesy of Morgan Xenos · Dragas Companies Realty IncREIN MLS #10659277
$765,425Crestfield At Centerville2032 Charwood DrChesapeake, VA 233205 bd3.1 ba3,089 sqftListing courtesy of Morgan Xenos · Dragas Companies Realty IncREIN MLS #10659274
$800,000Riverview LandingBellhaven-Multi-Gen plan · no street address yetChesapeake, VA 233225 bd3.1 ba3,240 sqftListing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10659297
$799,0971016 Cedar Tree (Squire on Homesite 4) CtChesapeake, VA 233233 bd2 ba2,134 sqftListing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10658960
$867,136Riverview Landing904 Intracoastal WayChesapeake, VA 233225 bd4.1 ba3,455 sqftListing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10658871
$985,000Hickory1630 Taft RdChesapeake, VA 233224 bd3.1 ba2,957 sqftListing courtesy of Herbert Culpepper · Pungo Realty LLCREIN MLS #10658171
$950,000Rollingwood Estates844 Greenfield LnChesapeake, VA 233226 bd5.1 ba5,000 sqftListing courtesy of Mark Spear · A Better Way Realty Inc.REIN MLS #10658157
$798,900Hickory2020 Sanderson RdChesapeake, VA 233224 bd3 ba3,223 sqftListing courtesy of Andy Gomez · Iron Valley Real Estate HRREIN MLS #10657878
$980,000Greystone821 Redleafe CirChesapeake, VA 233206 bd4 ba4,800 sqftListing courtesy of Jennifer Taylor · BHHS RW Towne RealtyREIN MLS #10657839
$899,990Riverview Landing1268 Kidbrooke StChesapeake, VA 233226 bd5 ba4,409 sqftListing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10657735
$1,199,000Hickory509 Ballahack RdChesapeake, VA 233225 bd3.1 ba3,714 sqftListing courtesy of Savannah Goodling · Long & Foster Real Estate Inc.REIN MLS #10657504
Price reduced$948,000Woodford Estateswas$964,500203 Hessian LoopChesapeake, VA 233225 bd3 ba2,828 sqftListing courtesy of Becky Gordon · BHHS RW Towne RealtyREIN MLS #10657075
$845,000Riverview LandingMacon-Multi-Gen plan · no street address yetChesapeake, VA 233225 bd4.1 ba3,535 sqftListing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10656573
$1,650,000Deep Creek3342 Martin Johnson RdChesapeake, VA 233235 bd3.2 ba5,952 sqftListing courtesy of Farra Sawyer · Howard Hanna Real Estate Svcs.REIN MLS #10656180
$825,000Ravenna1503 Theodora CtChesapeake, VA 233226 bd3 ba3,854 sqftListing courtesy of Joseph Perez · RE/MAX AllianceREIN MLS #10656228
Price reduced$925,000Hickorywas$939,5001149 Beaver Dam RdChesapeake, VA 233224 bd3.1 ba3,589 sqftListing courtesy of Laura McGuire · VA Realty ProfessionalsREIN MLS #10655807
Price reduced$875,000Hickorywas$879,0002410 Centerville TpkeChesapeake, VA 233223 bd2 ba2,863 sqftListing courtesy of Shawna Hulen · Own Real Estate LLCREIN MLS #10655763
$975,000Hickory2536 Seven Eleven RdChesapeake, VA 233226 bd3.1 ba4,236 sqftListing courtesy of Jessica Haynes · Keller Williams Capital Props.REIN MLS #10655175
Price reduced$797,540Riverview Landingwas$797,640911 Intracoastal WayChesapeake, VA 233225 bd3.1 ba3,226 sqftListing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655214
$1,100,000Mariners Pointe1824 Lancing Crest LnChesapeake, VA 233235 bd4.1 ba4,800 sqftListing courtesy of Ryan MacFarland · Atlantic Sothebys Int'l RealtyREIN MLS #10654932
Price reduced$849,900Albemarle Farm Northwas$879,900609 Fairfield DrChesapeake, VA 233224 bd2.1 ba2,850 sqftListing courtesy of Megan Anderson · Keller Williams Realty Twn CtrREIN MLS #10654253
Price reduced$829,900Hickorywas$839,9001733 Head of River RdChesapeake, VA 233224 bd3 ba2,912 sqftListing courtesy of Jennifer Stimpson · RE/MAX AllianceREIN MLS #10654135
$765,000Riverview LandingMacon plan · no street address yetChesapeake, VA 233225 bd4 ba3,213 sqftListing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10654675
Price reduced$881,140Riverview Landingwas$881,2401248 Kidbrooke StChesapeake, VA 233226 bd5 ba4,427 sqftListing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10654587
$799,900Culpepper Landing732 Colonel Byrd StChesapeake, VA 233236 bd4 ba3,656 sqftListing courtesy of Jennifer Castello · 1st Class Real Estate FlagshipREIN MLS #10654449
Price reduced$899,900Kemp Bridgewas$915,0001412 Kemp Bridge LnChesapeake, VA 233206 bd4.1 ba5,187 sqftListing courtesy of Jennifer Phan · Iron Valley Real Estate PrestigeREIN MLS #10654177
$758,900Savanna Heights237 Castleberry DrChesapeake, VA 233226 bd3 ba3,414 sqftListing courtesy of Jennifer Ringwald · Latitude Realty Co.REIN MLS #10653849
$793,267Riverview Landing212 Kwanzan CtChesapeake, VA 233225 bd3 ba2,888 sqftListing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10654133
Price reduced$999,999Hickorywas$1,100,0001741 Taft RdChesapeake, VA 233224 bd2.1 ba3,700 sqftListing courtesy of Leslie Coleman · Own Real Estate LLCREIN MLS #10653479
$1,000,000Grassfield Meadows3132 Benefit RdChesapeake, VA 233226 bd3 ba3,600 sqftListing courtesy of Debbie Woolard · Howard Hanna Real Estate Svcs.REIN MLS #10652479
$989,900Hickory4020 Tucker LnChesapeake, VA 233224 bd3.1 ba3,000 sqftListing courtesy of Janice Hollowell · World Class RealtyREIN MLS #10652733
$898,339Sanderson EstatesMm Raccoon (Lee on 11-1) TrlChesapeake, VA 233224 bd3.1 ba2,984 sqftListing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10651511
$945,170Beaver Dam (Holden) Rd plan · no street address yetChesapeake, VA 233224 bd3.1 ba3,424 sqftListing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10651510
$753,647The Fields At TaftMm Taft (Lee A-5) RdChesapeake, VA 233224 bd3.1 ba2,984 sqftListing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10651305
$755,166Sanderson EstatesMm Raccoon (Reba on 16-3) TrlChesapeake, VA 233223 bd2.1 ba1,938 sqftListing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10650490
Price reduced$845,000Sentry Estateswas$849,8002537 Number Ten LnChesapeake, VA 233236 bd4.1 ba3,251 sqftListing courtesy of Delia Longoria · 1st Class RE Mid-AtlanticREIN MLS #10648478
Price reduced$769,900Hillcrestwas$785,000633 Ambrose StChesapeake, VA 233225 bd3 ba3,300 sqftListing courtesy of Katie Donahue · BHHS RW Towne RealtyREIN MLS #10648928
$769,990Riverview LandingThe Tillman at plan · no street address yetChesapeake, VA 233225 bd3.1 ba3,226 sqftListing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10648510
$825,000Hickory1837 Benefit RdChesapeake, VA 233224 bd4 ba2,769 sqftListing courtesy of Tyler Shelton · RE/MAX AllegianceREIN MLS #10647485
Price reduced$759,900Martins Pointwas$799,9003909 Bruce RdChesapeake, VA 233215 bd3 ba3,125 sqftListing courtesy of Ann O'Brien · Howard Hanna Real Estate Svcs.REIN MLS #10647712
$1,200,000Hickory1717 Long Ridge RdChesapeake, VA 233224 bd3.1 ba3,497 sqftListing courtesy of Tara Davis · RE/MAX ElevateREIN MLS #10647623
$829,900Southwood825 Waterfall WayChesapeake, VA 233224 bd3 ba3,134 sqftListing courtesy of Kim Stanley · GreenTree Realty IncREIN MLS #10646857
Price reduced$899,000Berkshire Estateswas$909,500138 Greengable WayChesapeake, VA 233225 bd4 ba3,755 sqftListing courtesy of Linda Brooks · Long & Foster Real Estate Inc.REIN MLS #10647253
Price reduced$791,790Riverview Landingwas$791,890325 Riverview RdChesapeake, VA 233225 bd3.1 ba3,226 sqftListing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10646215
$849,900Shillelagh Farms1833 Shillelagh RdChesapeake, VA 233235 bd4.1 ba2,754 sqftListing courtesy of Douglas Kellam · EXP Realty LLCREIN MLS #10646141
$795,000Riverwalk804 River StrandChesapeake, VA 233206 bd3.1 ba3,955 sqftListing courtesy of Frank Mangum · Frank Mangum Realty Inc.REIN MLS #10643149
$919,000109 Ballahack RdChesapeake, VA 233223 bd2.1 ba2,734 sqftListing courtesy of Judy Duke · Wainwright Real EstateREIN MLS #10643968
$1,069,417Sanderson Estates2861 Raccoon TrlChesapeake, VA 233225 bd4 ba3,570 sqftListing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643118
$894,595Sanderson Estates2857 Raccoon TrlChesapeake, VA 233225 bd3 ba3,026 sqftListing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643669
$988,6132116 Sanderson RdChesapeake, VA 233224 bd3.1 ba3,424 sqftListing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10643550
$997,724Sanderson Estates1533 Sanderson RdChesapeake, VA 233225 bd4.1 ba3,585 sqftListing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643679
$1,104,938Sanderson Estates2801 Raccoon TrlChesapeake, VA 233224 bd3.1 ba3,637 sqftListing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643126
Showing 1–60 of 163
Homes for sale are listed first, newest listings first; homes under contract follow.
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+21 lots | 2 | 962 sqft | 1960 | Est. payment up to $1,027/mo | See all 33 listings → |
| $200K–$300K | 102+12 lots | 3 | 1,266 sqft | 1984 | Est. payment $1,284/mo | See all 114 listings → |
| $300K–$400K | 172+2 lots | 3 | 1,602 sqft | 1984 | Est. payment $1,798/mo | See all 174 listings → |
| $400K–$500K | 137+6 lots | 4 | 2,047 sqft | 1995 | Est. payment $2,311/mo | See all 143 listings → |
| $500K–$750K | 269+5 lots | 4 | 2,632 sqft | 2017 | Est. payment $3,210/mo | See all 274 listings → |
| Over $750K | 86+6 lots | 4–5 | 3,226 sqft | 2026 | Est. payment from $3,852/mo | Shown on this page |
Market snapshot
Chesapeake homes over $750,000: market snapshot, November 2026
Of the 92 listings for sale in Chesapeake over $750,000, 16 (17%) have had a price cut, and another 71 are under contract. The median active listing has been on the market 38 days (REIN).
For sale now
- Median price per sq ft
- $278
- Under contract
- 71
- With a price cut
- 1617% of homes for sale
Recently sold
- Homes sold
- 155
- Median sold price
- $879,000
- Median days on market (REIN)
- 20 days
- Median sold price per sq ft
- $249
Closed sales from REIN MLS, March 2026 – October 2026.
Chesapeake housing market trends →Chesapeake market report PDF →
Data: REIN MLS, November 4, 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 over $750,000: FAQ
How many homes are for sale in Chesapeake, VA over $750,000?
As of November 4, 2026, REIN MLS shows 86 homes for sale in Chesapeake over $750,000, plus 6 lots. Another 71 listings are under contract. Of the 92 listings for sale, 8 have been listed since October 29 and 16 have had a price cut.
What do homes over $750,000 in Chesapeake look like?
The median list price of the 92 listings for sale in Chesapeake over $750,000, 6 lots included, is $878,070 as of November 4, 2026. The typical home has 4–5 bedrooms and about 3,226 sq ft, and was built in 2026. The median list price per square foot is $278.
How fast do homes over $750,000 sell in Chesapeake?
From March 2026 through October 2026, 155 homes in Chesapeake sold over $750,000 on REIN MLS, at a median sold price of $879,000. The median closed sale was on the market 20 days (REIN).
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