New
$1,100,000Hickory
1741 Taft Rd
Chesapeake, VA 23322
4 bd2.1 ba3,700 sqft
Listing courtesy of Leslie Coleman · Own Real Estate LLCREIN MLS #10653479
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 Sep 16, 2:10 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 $881,700. The typical home has 5 bedrooms and about 3,240 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$881,700
- New this week6
- Median days on market (REIN, active listings)31 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
(+77 under contract)Skip the 60 listings
New$850,000Hickory2329 Centerville Tpke S
Chesapeake, VA 23322
4 bd3 ba3,575 sqft
Listing courtesy of Diane Keeley · BHHS RW Towne RealtyREIN MLS #10653178
New$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
NewOpen Sun 1–3 PM$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
New$998,895Shillelagh Farms1910 Hallmark Way
Chesapeake, VA 23323
5 bd3.1 ba3,988 sqft
Listing courtesy of Amelia Coppage · Fathom RealtyREIN MLS #10652907
New$989,900Hickory4020 Tucker Ln
Chesapeake, VA 23322
4 bd3.1 ba3,000 sqft
Listing courtesy of Janice Hollowell · World Class RealtyREIN MLS #10652733
New$849,900Stonebridge Landing3808 Millgrove Ct
Chesapeake, VA 23321
4 bd3 ba3,656 sqft
Listing courtesy of Amanda Emanuel · BHHS RW Towne RealtyREIN MLS #10652646
$769,000Hickory1204 Murray Dr
Chesapeake, VA 23322
5 bd3 ba3,712 sqft
Listing courtesy of Deborah Rountree · BHHS RW Towne RealtyREIN MLS #10651816
Price reduced$869,000Sentry Estateswas
$885,0002517 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
$763,990Riverview 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$840,000Creekwoodwas
$850,0002602 Cecilia Ter
Chesapeake, VA 23323
6 bd4 ba3,500 sqft
Listing courtesy of Angela Kennedy · 1st Class Real Estate IntegrityREIN MLS #10650808
Open Sat 12–2 PM$1,500,000Hickory1120 Kathleen Ln
Chesapeake, VA 23322
5 bd3.1 ba7,155 sqft
Listing courtesy of Betsy Thompson · The AgencyREIN MLS #10650552
$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 Sat 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
$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$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
Price reduced$839,000Rollingwood Estateswas
$850,000712 Greenfield Ln
Chesapeake, VA 23322
5 bd3 ba3,394 sqft
Listing courtesy of Adrielle Roxas · LPT Realty LLCREIN MLS #10648245
Price reduced$839,900Riverwoodwas
$849,9003504 Riverwood Cres
Chesapeake, VA 23322
5 bd4.1 ba4,670 sqft
Listing courtesy of Eric Maldonado · AtCoastal RealtyREIN MLS #10649639
Price reduced$975,000Rollingwood Estateswas
$985,000844 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$789,900Hillcrestwas
$799,000633 Ambrose St
Chesapeake, VA 23322
5 bd3 ba3,300 sqft
Listing courtesy of Katie Donahue · BHHS RW Towne RealtyREIN MLS #10648928
$799,000Hickory2020 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$925,000was
$975,0002008 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
$825,000Pleasant Grove2239 Benefit Rd
Chesapeake, VA 23322
4 bd3.1 ba3,000 sqft
Listing courtesy of Cheryl Huotte · Metro Brokers of Hampton RoadsREIN MLS #10648270
Price reduced$799,900Martins Pointwas
$839,5003909 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
$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 #10647443
$922,500Berkshire Estates138 Greengable Way
Chesapeake, VA 23322
5 bd4 ba3,755 sqft
Listing courtesy of Linda Brooks · Long & Foster Real Estate Inc.REIN MLS #10647253
Price reduced$765,000Emerald Lakeswas
$775,0001204 Lingale Ct
Chesapeake, VA 23322
5 bd3 ba3,200 sqft
Listing courtesy of Kristie Weaver · SerhantREIN MLS #10646970
$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
$788,990Riverview 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
$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 #10645689
Price reduced$899,800Hickorywas
$899,900435 Gallbush Rd
Chesapeake, VA 23322
4 bd3 ba2,725 sqft
Listing courtesy of Matthew Monaco · BHHS RW Towne RealtyREIN MLS #10645653
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
$793,267Riverview Landing212 Kwanzan Ct
Chesapeake, VA 23322
5 bd3 ba2,888 sqft
Listing courtesy of Jasmine Feliu · BHHS RW Towne RealtyREIN MLS #10644581
$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
$916,000109 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
$988,6132116 Sanderson Rd
Chesapeake, VA 23322
4 bd3.1 ba3,424 sqft
Listing courtesy of Deana Renn · AtCoastal RealtyREIN MLS #10643550
$997,724Sanderson Estates1533 Sanderson Rd
Chesapeake, VA 23322
5 bd4.1 ba3,585 sqft
Listing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643679
$1,104,938Sanderson Estates2801 Raccoon Trl
Chesapeake, VA 23322
4 bd3.1 ba3,637 sqft
Listing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643126
$949,608Sanderson Estates1516 Cedarville Ct
Chesapeake, VA 23322
4 bd3.1 ba3,185 sqft
Listing courtesy of Joy Mills · AtCoastal RealtyREIN MLS #10643106
Price reduced$885,000King James Colonywas
$890,000537 Margaret Dr
Chesapeake, VA 23322
7 bd4 ba3,786 sqft
Listing courtesy of Reagan Feuerhahn · Prodigy RealtyREIN MLS #10643086
$1,750,000Hunters Ridge2505 Sylvia Ct
Chesapeake, VA 23322
4 bd4 ba5,707 sqft
Listing courtesy of Patrick Clark · Byler RealtyREIN MLS #10642797
Price reduced$879,000Hickorywas
$889,0002410 Centerville Tpke
Chesapeake, VA 23322
3 bd2 ba2,863 sqft
Listing courtesy of Shawna Hulen · Own Real Estate LLCREIN MLS #10642255
Showing 1–60 of 179
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 | 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 | See all 276 listings → |
| Over $750K | 96+6 lots | 5 | 3,240 sqft | 2026 | Est. payment from $3,852/mo | Shown on this page |
Market snapshot
Chesapeake homes over $750,000: market snapshot, September 2026
Of the 102 listings for sale in Chesapeake over $750,000, 30 (29%) have had a price cut, and another 77 are under contract. The median active listing has been on the market 31 days (REIN).
For sale now
- Median price per sq ft
- $267
- Under contract
- 77
- With a price cut
- 3029% of homes for sale
Recently sold
- Homes sold
- 129
- Median sold price
- $869,000
- Median days on market (REIN)
- 18 days
- Median sold price per sq ft
- $252
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 over $750,000: FAQ
How many homes are for sale in Chesapeake, VA over $750,000?
As of September 16, 2026, REIN MLS shows 96 homes for sale in Chesapeake over $750,000, plus 6 lots. Another 77 listings are under contract. Of the 102 listings for sale, 6 have been listed since September 10 and 30 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 $881,700 as of September 16, 2026. The typical home has 5 bedrooms and about 3,240 sq ft, and was built in 2026. The median list price per square foot is $267.
How fast do homes over $750,000 sell in Chesapeake?
From March 2026 through August 2026, 129 homes in Chesapeake sold over $750,000 on REIN MLS, at a median sold price of $869,000. The median closed sale was on the market 18 days (REIN).
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