New
$964,500Woodford Estates
203 Hessian Loop
Chesapeake, VA 23322
5 bd3 ba2,828 sqft
Listing courtesy of Becky Gordon · BHHS RW Towne RealtyREIN MLS #10657075
Luxury Homes for Sale in Chesapeake, VA: $750,000 and Up
96 homes for sale in Chesapeake, VA over $750,000, plus 6 lots, from REIN MLS · Listing data as of Oct 10, 3:10 PM ET (syncs every 2 minutes)
96 homes and 6 lots are for sale in Chesapeake over $750,000 today, at a median list price of $886,048. The typical home has 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 now102
- Median list price$886,048
- New this week2
- Median days on market (REIN, active listings)46 days
Source: REIN MLS. These figures include lots and exclude homes under contract.
96 Chesapeake homes and 6 lots for sale in this price range right now
(+73 under contract)Skip the 60 listings
New$845,000Riverview LandingMacon-Multi-Gen plan · no street address yet
Chesapeake, VA 23322
5 bd4.1 ba3,535 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10656573
New$825,000Ravenna1503 Theodora Ct
Chesapeake, VA 23322
6 bd3 ba3,854 sqft
Listing courtesy of Joseph Perez · RE/MAX AllianceREIN MLS #10656228
New$1,650,000Deep Creek3342 Martin Johnson Rd
Chesapeake, VA 23323
5 bd3.2 ba5,952 sqft
Listing courtesy of Farra Sawyer · Howard Hanna Real Estate Svcs.REIN MLS #10656180
$950,000Hickory241 Sign Pine Rd
Chesapeake, VA 23322
4 bd3.1 ba3,063 sqft
Listing courtesy of Betsy Thompson · The AgencyREIN MLS #10655919
New$939,500Hickory1149 Beaver Dam Rd
Chesapeake, VA 23322
4 bd3.1 ba3,589 sqft
Listing courtesy of Laura McGuire · VA Realty ProfessionalsREIN MLS #10655807
$879,000Hickory2410 Centerville Tpke
Chesapeake, VA 23322
3 bd2 ba2,863 sqft
Listing courtesy of Shawna Hulen · Own Real Estate LLCREIN MLS #10655763
$797,640Riverview Landing911 Intracoastal Way
Chesapeake, VA 23322
5 bd3.1 ba3,226 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10655214
$975,000Hickory2536 Seven Eleven Rd
Chesapeake, VA 23322
6 bd3.1 ba4,236 sqft
Listing courtesy of Jessica Haynes · Keller Williams Capital Props.REIN MLS #10655175
$1,300,000Hickory1713 Sanderson Rd
Chesapeake, VA 23322
4 bd2.1 ba3,296 sqft
Listing courtesy of Hannah Arnold · BHHS RW Towne RealtyREIN MLS #10654856
$849,900Hickory435 Gallbush Rd
Chesapeake, VA 23322
4 bd3 ba2,725 sqft
Listing courtesy of Matthew Monaco · BHHS RW Towne RealtyREIN MLS #10655045
$879,900Albemarle Farm North609 Fairfield Dr
Chesapeake, VA 23322
4 bd2.1 ba2,850 sqft
Listing courtesy of Megan Anderson · Keller Williams Realty Twn CtrREIN MLS #10654253
$839,900Hickory1733 Head of River Rd
Chesapeake, VA 23322
4 bd3 ba2,912 sqft
Listing courtesy of Jennifer Stimpson · RE/MAX AllianceREIN MLS #10654135
$1,100,000Mariners Pointe1824 Lancing Crest Ln
Chesapeake, VA 23323
5 bd4.1 ba4,800 sqft
Listing courtesy of Ryan MacFarland · Atlantic Sothebys Int'l RealtyREIN MLS #10654932
$765,000Riverview LandingMacon plan · no street address yet
Chesapeake, VA 23322
5 bd4 ba3,213 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10654675
$881,240Riverview Landing1248 Kidbrooke St
Chesapeake, VA 23322
6 bd5 ba4,427 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10654587
$799,900Culpepper Landing732 Colonel Byrd St
Chesapeake, VA 23323
6 bd4 ba3,656 sqft
Listing courtesy of Jennifer Castello · 1st Class Real Estate FlagshipREIN MLS #10654449
$925,000Kemp Bridge1412 Kemp Bridge Ln
Chesapeake, VA 23320
6 bd4.1 ba5,187 sqft
Listing courtesy of Jennifer Phan · Iron Valley Real Estate PrestigeREIN MLS #10654177
$758,900Savanna Heights237 Castleberry Dr
Chesapeake, VA 23322
6 bd3 ba3,414 sqft
Listing courtesy of Jennifer Ringwald · Latitude Realty Co.REIN MLS #10653849
$793,267Riverview Landing212 Kwanzan Ct
Chesapeake, VA 23322
5 bd3 ba2,888 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10654133
Price reduced$999,999Hickorywas
$1,100,0001741 Taft Rd
Chesapeake, VA 23322
4 bd2.1 ba3,700 sqft
Listing courtesy of Leslie Coleman · Own Real Estate LLCREIN MLS #10653479
$775,000Riverwood3708 Riverwood Cres
Chesapeake, VA 23322
5 bd2.1 ba2,978 sqft
Listing courtesy of Nicole Rivera · 1st Class Real Estate ElevateREIN MLS #10653033
$1,000,000Grassfield Meadows3132 Benefit Rd
Chesapeake, VA 23322
6 bd3 ba3,600 sqft
Listing courtesy of Debbie Woolard · Howard Hanna Real Estate Svcs.REIN MLS #10652479
$989,900Hickory4020 Tucker Ln
Chesapeake, VA 23322
4 bd3.1 ba3,000 sqft
Listing courtesy of Janice Hollowell · World Class RealtyREIN MLS #10652733
Price reduced$860,000Sentry Estateswas
$869,0002517 Number Ten Ln
Chesapeake, VA 23323
4 bd3.1 ba2,941 sqft
Listing courtesy of Kate Pitre · BHHS RW Towne RealtyREIN MLS #10651664
$1,519,000Great Bridge641 Ravenwoods Dr
Chesapeake, VA 23322
5 bd4.1 ba6,848 sqft
Listing courtesy of Kelly DiPasquale · Aweigh Real EstateREIN MLS #10651679
Open Sun 12–6 PM$764,890Riverview Landing984 Intracoastal Way
Chesapeake, VA 23322
6 bd4.1 ba3,224 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10651532
$898,339Sanderson EstatesMm Raccoon (Lee on 11-1) Trl
Chesapeake, VA 23322
4 bd3.1 ba2,984 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10651511
$945,170Beaver Dam (Holden) Rd plan · no street address yet
Chesapeake, VA 23322
4 bd3.1 ba3,424 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10651510
$753,647The Fields At TaftMm Taft (Lee A-5) Rd
Chesapeake, VA 23322
4 bd3.1 ba2,984 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10651305
Price reduced$790,000Creekwoodwas
$800,0002602 Cecilia Ter
Chesapeake, VA 23323
6 bd4 ba3,500 sqft
Listing courtesy of Angela Kennedy · 1st Class Real Estate IntegrityREIN MLS #10650808
$800,000Riverview LandingBellhaven-Multi-Gen plan · no street address yet
Chesapeake, VA 23322
5 bd3.1 ba3,240 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10650728
$799,900Pleasant Grove2907 Seven Eleven Rd
Chesapeake, VA 23322
4 bd2.1 ba2,400 sqft
Listing courtesy of Rachel Beasley · KW Allegiance ShorelineREIN MLS #10650499
$755,166Sanderson EstatesMm Raccoon (Reba on 16-3) Trl
Chesapeake, VA 23322
3 bd2.1 ba1,938 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10650490
Open Sun 1–3 PM$899,900Hickory1421 Saint Brides Road West
Chesapeake, VA 23322
4 bd3.1 ba2,720 sqft
Listing courtesy of Rachael Turner · GreenTree Realty IncREIN MLS #10650094
$765,000Warrington Hall700 Old Fields Arch
Chesapeake, VA 23320
4 bd4 ba4,230 sqft
Listing courtesy of Michael Ware · Own Real Estate LLCREIN MLS #10649884
Price reduced$849,800Sentry Estateswas
$849,9002537 Number Ten Ln
Chesapeake, VA 23323
6 bd4.1 ba3,251 sqft
Listing courtesy of Delia Longoria · 1st Class RE Mid-AtlanticREIN MLS #10648478
$2,495,000Tanglewood4112 Mingo Trl
Chesapeake, VA 23325
6 bd7.1 ba8,000 sqft
Listing courtesy of Tim Cochran · BHHS RW Towne RealtyREIN MLS #10649916
Price reduced$965,000Rollingwood Estateswas
$975,000844 Greenfield Ln
Chesapeake, VA 23322
6 bd5.1 ba5,000 sqft
Listing courtesy of Mark Spear · A Better Way Realty Inc.REIN MLS #10648547
Price reduced$1,199,000Pleasant Grovewas
$1,299,000509 Ballahack Rd
Chesapeake, VA 23322
5 bd3.1 ba3,714 sqft
Listing courtesy of Savannah Goodling · Long & Foster Real Estate Inc.REIN MLS #10648292
Price reduced$769,900Hillcrestwas
$785,000633 Ambrose St
Chesapeake, VA 23322
5 bd3 ba3,300 sqft
Listing courtesy of Katie Donahue · BHHS RW Towne RealtyREIN MLS #10648928
Price reduced$798,900Hickorywas
$799,0002020 Sanderson Rd
Chesapeake, VA 23322
4 bd3 ba3,223 sqft
Listing courtesy of Andy Gomez · Iron Valley Real Estate HRREIN MLS #10648602
$769,990Riverview LandingThe Tillman at plan · no street address yet
Chesapeake, VA 23322
5 bd3.1 ba3,226 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10648510
Price reduced$889,500was
$925,0002008 Pocaty Creek Ln
Chesapeake, VA 23322
4 bd3.1 ba4,000 sqft
Listing courtesy of Patricia Zuraw · Howard Hanna Real Estate Svcs.REIN MLS #10647773
$825,000Hickory1837 Benefit Rd
Chesapeake, VA 23322
4 bd4 ba2,769 sqft
Listing courtesy of Tyler Shelton · RE/MAX AllegianceREIN MLS #10647485
Price reduced$935,000Hickorywas
$950,0001908 Benefit Rd
Chesapeake, VA 23322
5 bd3 ba3,252 sqft
Listing courtesy of Jason Houser · North End Realty GroupREIN MLS #10648261
Price reduced$784,900was
$794,9001024 Loutro Ct
Chesapeake, VA 23322
6 bd3 ba3,200 sqft
Listing courtesy of Manuel Solano · Better Homes & Gdns Ntv Am GrpREIN MLS #10647933
Price reducedOpen Sun 1–3 PM$759,900Martins Pointwas
$799,9003909 Bruce Rd
Chesapeake, VA 23321
5 bd3 ba3,125 sqft
Listing courtesy of Ann O'Brien · Howard Hanna Real Estate Svcs.REIN MLS #10647712
$1,200,000Hickory1717 Long Ridge Rd
Chesapeake, VA 23322
4 bd3.1 ba3,497 sqft
Listing courtesy of Tara Davis · RE/MAX ElevateREIN MLS #10647623
$829,900Southwood825 Waterfall Way
Chesapeake, VA 23322
4 bd3 ba3,134 sqft
Listing courtesy of Kim Stanley · GreenTree Realty IncREIN MLS #10646857
Price reduced$909,500Berkshire Estateswas
$922,500138 Greengable Way
Chesapeake, VA 23322
5 bd4 ba3,755 sqft
Listing courtesy of Linda Brooks · Long & Foster Real Estate Inc.REIN MLS #10647253
Open Sun 12–6 PM$769,740Riverview Landing321 Riverview Rd
Chesapeake, VA 23322
5 bd4 ba3,165 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10646721
$995,000Greystone821 Redleafe Cir
Chesapeake, VA 23320
6 bd4 ba4,800 sqft
Listing courtesy of Jennifer Taylor · BHHS RW Towne RealtyREIN MLS #10645935
$791,890Riverview Landing325 Riverview Rd
Chesapeake, VA 23322
5 bd3.1 ba3,226 sqft
Listing courtesy of Victoria Clark · D R Horton Realty of VirginiaREIN MLS #10646215
$849,900Shillelagh Farms1833 Shillelagh Rd
Chesapeake, VA 23323
5 bd4.1 ba2,754 sqft
Listing courtesy of Douglas Kellam · EXP Realty LLCREIN MLS #10646141
Price reduced$795,000Pleasant Grovewas
$825,000208 Leicester Ct
Chesapeake, VA 23322
5 bd3 ba4,160 sqft
Listing courtesy of Kristina Miklos · Judy Reed RealtyREIN MLS #10644737
$795,000Riverwalk804 River Strand
Chesapeake, VA 23320
6 bd3.1 ba3,955 sqft
Listing courtesy of Frank Mangum · Frank Mangum Realty Inc.REIN MLS #10643149
$919,000109 Ballahack Rd
Chesapeake, VA 23322
3 bd2.1 ba2,734 sqft
Listing courtesy of Judy Duke · Wainwright Real EstateREIN MLS #10643968
$1,069,417Sanderson Estates2861 Raccoon Trl
Chesapeake, VA 23322
5 bd4 ba3,570 sqft
Listing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643118
$894,595Sanderson Estates2857 Raccoon Trl
Chesapeake, VA 23322
5 bd3 ba3,026 sqft
Listing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643669
Showing 1–60 of 175
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 | 14+42 lots | 2 | 928 sqft | 1978 | Est. payment up to $1,027/mo | See all 56 listings → |
| $200K–$300K | 94+12 lots | 3 | 1,249 sqft | 1983 | Est. payment $1,284/mo | See all 106 listings → |
| $300K–$400K | 145+1 lot | 3 | 1,582 sqft | 1981 | Est. payment $1,798/mo | See all 146 listings → |
| $400K–$500K | 126+6 lots | 4 | 2,034 sqft | 1997 | Est. payment $2,311/mo | See all 132 listings → |
| $500K–$750K | 277+5 lots | 4 | 2,620 sqft | 2017 | Est. payment $3,210/mo | See all 282 listings → |
| Over $750K | 96+6 lots | 5 | 3,226 sqft | 2026 | Est. payment from $3,852/mo | Shown on this page |
Market snapshot
Chesapeake homes over $750,000: market snapshot, October 2026
Of the 102 listings for sale in Chesapeake over $750,000, 22 (22%) have had a price cut, and another 73 are under contract. The median active listing has been on the market 46 days (REIN).
For sale now
- Median price per sq ft
- $277
- Under contract
- 73
- With a price cut
- 2222% of homes for sale
Recently sold
- Homes sold
- 139
- Median sold price
- $883,000
- Median days on market (REIN)
- 18 days
- Median sold price per sq ft
- $254
Closed sales from REIN MLS, March 2026 – September 2026.
Chesapeake housing market trends →Chesapeake market report PDF →
Data: REIN MLS, October 10, 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 October 10, 2026, REIN MLS shows 96 homes for sale in Chesapeake over $750,000, plus 6 lots. Another 73 listings are under contract. Of the 102 listings for sale, 2 have been listed since October 4 and 22 have had a price cut.
What do homes over $750,000 in Chesapeake look like?
The median list price of the 102 listings for sale in Chesapeake over $750,000, 6 lots included, is $886,048 as of October 10, 2026. The typical home has 5 bedrooms and about 3,226 sq ft, and was built in 2026. The median list price per square foot is $277.
How fast do homes over $750,000 sell in Chesapeake?
From March 2026 through September 2026, 139 homes in Chesapeake sold over $750,000 on REIN MLS, at a median sold price of $883,000. The median closed sale was on the market 18 days (REIN).
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