New
$315,000Deep Creek Shores
504 Plummer Dr
Chesapeake, VA 23320
3 bd1 ba1,094 sqft
Listing courtesy of Caitlin Dress · COVA Home RealtyREIN MLS #10659413
Homes for Sale in Chesapeake, VA: $300,000 to $400,000
156 homes for sale in Chesapeake, VA from $300,000 to $400,000, plus 2 lots, from REIN MLS · Listing data as of Oct 27, 3:00 AM ET (syncs every 2 minutes)
156 homes and 2 lots are for sale in Chesapeake from $300,000 to $400,000 today, at a median list price of $349,950. The typical home has 3 bedrooms and about 1,588 sq ft, and was built in 1984.
Tom & Dariya Milan, RealtorsBrokered by LPT Realty · Call or text (757) 777-7577
- For sale now158
- Median list price$349,950
- New this week27
- Median days on market (REIN, active listings)12 days
Source: REIN MLS. These figures include lots and exclude homes under contract.
156 Chesapeake homes and 2 lots for sale in this price range right now
(+76 under contract)Skip the 60 listingsSkip to this week's listings
Coming Soon$369,900Camelot1108 Sword DrChesapeake, VA 233234 bd2 ba1,800 sqftListing courtesy of Marie Brinkman · COVA Home RealtyREIN MLS #10659368
NewOpen Sun 12–5 PM$387,900The Grove4908 Apricot WayChesapeake, VA 233213 bd2.1 ba1,642 sqftListing courtesy of Angela McCaskill · Corinth Realty LLCREIN MLS #10659350
New$375,000Chadswyck Terrace4009 San Salvador DrChesapeake, VA 233213 bd1.1 ba1,771 sqftListing courtesy of Sandy White · Creed RealtyREIN MLS #10659336
New$395,000Chadswyck Terrace4009 Santa Maria DrChesapeake, VA 233213 bd1.1 ba1,578 sqftListing courtesy of Tracey Caddy · Southside Real EstateREIN MLS #10659264
New$325,000Grassfield Meadows1849 Cedar RdChesapeake, VA 233232 bd1 ba1,096 sqftListing courtesy of Nadine Napolitano · Green Tree Real Estate IncREIN MLS #10658693
Lot / landNew$400,000Pleasant Grove5.1 Ac Ranger RdChesapeake, VA 23322Listing courtesy of Angela Evans · Swell Realty CoREIN MLS #10659203
New$369,000Coleman Farms1233 Parkley DrChesapeake, VA 233203 bd2.1 ba1,774 sqftListing courtesy of Nicholas Conigliaro · The Real Estate GroupREIN MLS #10659161
New$399,000Chadswyck Terrace4012 Santa Maria DrChesapeake, VA 233213 bd2 ba1,334 sqftListing courtesy of Melody Cespedes · 1st Class Real Estate FlagshipREIN MLS #10659156
New$348,500Camelot1205 Aaron CtChesapeake, VA 233234 bd2 ba1,346 sqftListing courtesy of Marcella Montagna · CoastalVA Realty Inc.REIN MLS #10659138
New$325,130Grayson Commons1540 Eldwick Drive #307Chesapeake, VA 233202 bd2 ba1,386 sqftListing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10659135
New$320,130Grayson Commons1540 Eldwick Drive #104Chesapeake, VA 233202 bd2 ba1,355 sqftListing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10659133
New$309,900South Norfolk1416 Martin AveChesapeake, VA 233243 bd2.1 ba1,500 sqftListing courtesy of Michael Daugherty · Own Real Estate LLCREIN MLS #10659126
New$330,000Las Gaviotas428 San Roman DrChesapeake, VA 233223 bd2.1 ba1,528 sqftListing courtesy of Pamela Bowman · The Real Estate GroupREIN MLS #10659091
New$350,000Elmwood Landing3532 Parr LnChesapeake, VA 233234 bd2 ba1,400 sqftListing courtesy of Courtney Myers · Own Real Estate LLCREIN MLS #10659049
New$324,900Las Gaviotas471 San Roman DrChesapeake, VA 233223 bd1.1 ba1,290 sqftListing courtesy of Bridgette Hamm · The Real Estate GroupREIN MLS #10658841
New$350,000Camelot3085 Kenelm DrChesapeake, VA 233233 bd2 ba1,650 sqftListing courtesy of Sueann Sictor · A Better Way Realty Inc.REIN MLS #10659089
New$382,000Portlock Terrace4116 2nd StChesapeake, VA 233244 bd3 ba2,080 sqftListing courtesy of Steffanie Battles · 1st Class Real Estate FlagshipREIN MLS #10659003
New$306,500Cedar Lakes612 W Lake Cir #53Chesapeake, VA 233223 bd2.1 ba1,457 sqftListing courtesy of Erica Williams · ONYX Realty Professionals LLCREIN MLS #10658720
New$315,000Drum Creek Farms2408 Drum Creek RdChesapeake, VA 233213 bd1.1 ba1,134 sqftListing courtesy of Patricia Saunders · Creed RealtyREIN MLS #10658963
New$339,900South Norfolk1821 Hoover AveChesapeake, VA 233244 bd3 ba2,000 sqftListing courtesy of Shauna Lane · BHHS RW Towne RealtyREIN MLS #10658740
New$345,000Indian River Estates1204 Fontana AveChesapeake, VA 233253 bd1 ba1,441 sqftListing courtesy of Matthew Salway · Iron Valley Real Estate HRREIN MLS #10658872
New$371,500Camelot3141 Guenevere DrChesapeake, VA 233234 bd2 ba1,690 sqftListing courtesy of Steffanie Battles · 1st Class Real Estate FlagshipREIN MLS #10658736
New$325,000Wilmund Place4111 Williamson StChesapeake, VA 233243 bd2 ba1,200 sqftListing courtesy of Erika Miller · NextHome Beyond KeysREIN MLS #10658906
New$345,000Parkview1753 Burson DrChesapeake, VA 233235 bd2 ba1,700 sqftListing courtesy of Francheska Ferguson · The Real Estate GroupREIN MLS #10658681
New$350,000Pleasant View303 Diamond AveChesapeake, VA 233233 bd2 ba1,500 sqftListing courtesy of Shelly Taylor · Real Broker LLCREIN MLS #10658571
New$379,000Chadswyck Terrace2168 Armada Dr EChesapeake, VA 233213 bd1.1 ba1,487 sqftListing courtesy of Connie Bowe · Fathom RealtyREIN MLS #10658509
New$349,900Raleigh Heights1013 McKinley AveChesapeake, VA 233241,652 sqftListing courtesy of Conner Walters · World Class Realty & Prop MgmtREIN MLS #10658545
New$392,000Holly Glen306 Holly Glen DrChesapeake, VA 233254 bd2.1 ba2,028 sqftListing courtesy of Chuck Warren · Real Estate USAREIN MLS #10658566
New$329,900Camelot3057 Kenelm DrChesapeake, VA 233233 bd1.1 ba1,404 sqftListing courtesy of Jennifer Morgan · Thrive RealtyREIN MLS #10658506
Coming Soon$325,000Norfolk Highlands1735 Sparrow RdChesapeake, VA 233203 bd2 ba1,098 sqftListing courtesy of Shynara Manley · ONYX Realty Professionals LLCREIN MLS #10658417
New$315,000Brentwood1329 George Washington Hwy NChesapeake, VA 233233 bd2 ba1,730 sqftListing courtesy of Donna English · Iron Valley Real Estate PrestigeREIN MLS #10657422
New$375,000Raleigh Heights1431 Oliver AveChesapeake, VA 233244 bd3 ba2,000 sqftListing courtesy of Edgar Munoz · Iron Valley Real Estate PrestigeREIN MLS #10657417
New$329,000The Grove At The Arboretum514 Trellis TrlChesapeake, VA 233202 bd2.1 ba1,870 sqftListing courtesy of Karen Davis · Judy Reed RealtyREIN MLS #10658445
New$395,310Grayson Commons674 Allery RdChesapeake, VA 233202 bd2.1 ba1,847 sqftListing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10658410
New$400,000Logans Mill2110 Logans Mill TrlChesapeake, VA 233204 bd2.1 ba1,824 sqftListing courtesy of Daniel Trotman · CENTURY 21 Nachman RealtyREIN MLS #10658448
New$365,000Greenbrier Fairways801 Shoal Creek TrlChesapeake, VA 233202 bd2.1 ba1,684 sqftListing courtesy of Marsha Brady · Covington & Assoc. RealtorsREIN MLS #10658068
$385,000Camelot809 Parapet RdChesapeake, VA 233234 bd2.1 ba1,932 sqftListing courtesy of Phyllis Willoughby · EXIT Realty CentralREIN MLS #10658236
$390,000Coleman Farms2416 Fieldsway DrChesapeake, VA 233203 bd2.1 ba1,750 sqftListing courtesy of Amy Trahan · Sutton Tullio Realty LLCREIN MLS #10657521
$330,000South Norfolk2900 Rodgers StChesapeake, VA 233244 bd2 ba1,450 sqftListing courtesy of Gerry Sessor · A Better Way Realty Inc.REIN MLS #10658243
$399,900Wilmund Place930 Railroad AveChesapeake, VA 233243 bd2.1 ba1,436 sqftListing courtesy of Laura Rowe · BHHS RW Towne RealtyREIN MLS #10658249
$310,000Branford Square At Greenbrier1505 Waitsel Dr #306Chesapeake, VA 233202 bd2 ba1,327 sqftListing courtesy of Sara Dunbar · Redfin CorporationREIN MLS #10658216
$360,000Ahoy Acres3904 Starboard RdChesapeake, VA 233213 bd2 ba1,323 sqftListing courtesy of JaQuan Holloman · Iron Valley Real Estate PrestigeREIN MLS #10657836
$360,000Norfolk Highlands2022 Weber AveChesapeake, VA 233203 bd2.1 ba1,704 sqftListing courtesy of Matthew Salway · Iron Valley Real Estate HRREIN MLS #10657937
Open Fri 4–6 PM$360,000Lindbergh Manor1437 Glendale AveChesapeake, VA 233234 bd2 ba1,380 sqftListing courtesy of Heidi Johnson · Real Broker LLCREIN MLS #10658124
$355,000Camelot700 Saxon CtChesapeake, VA 233234 bd2 ba1,716 sqftListing courtesy of Aaron Gutierrez · Creed RealtyREIN MLS #10658131
$360,000Camelot1125 Sir Gawaine DrChesapeake, VA 233234 bd2.1 ba1,950 sqftListing courtesy of Aaron Gutierrez · Creed RealtyREIN MLS #10658020
$384,900Warrington Hall604 Old Fields ArchChesapeake, VA 233202 bd2.1 ba2,019 sqftListing courtesy of Michael Pattison · EXP Realty LLCREIN MLS #10657776
$399,900Wilmund Place905 Railroad AveChesapeake, VA 233243 bd2.1 ba1,654 sqftListing courtesy of Laura Rowe · BHHS RW Towne RealtyREIN MLS #10658090
$310,000South Norfolk2035 Christian AveChesapeake, VA 233243 bd2.1 ba1,204 sqftListing courtesy of Charles Williams · Keller Williams Realty Twn CtrREIN MLS #10657931
$360,000Camelot3019 Roundtable DrChesapeake, VA 233233 bd2 ba1,842 sqftListing courtesy of Phillip Davis · Keller Williams Realty Twn CtrREIN MLS #10657719
$380,000Dockwood1805 Dockwood TrlChesapeake, VA 233213 bd1.1 ba1,500 sqftListing courtesy of Bridgette Hamm · The Real Estate GroupREIN MLS #10657429
$379,900Norfolk Highlands1129 Hazel AveChesapeake, VA 233254 bd3.1 ba2,000 sqftListing courtesy of Kathleen McClintock · Keller Williams Realty Twn CtrREIN MLS #10657809
Open Sun 12–5 PM$329,900The Grove4995 Boone RdChesapeake, VA 233212 bd2.1 ba1,464 sqftListing courtesy of Breyana Hawks · Corinth Realty LLCREIN MLS #10657742
$334,900The Grove4993 Boone RdChesapeake, VA 233212 bd2.1 ba1,464 sqftListing courtesy of Breyana Hawks · Corinth Realty LLCREIN MLS #10657595
$345,000Camelot844 Parapet RdChesapeake, VA 233234 bd2.1 ba1,656 sqftListing courtesy of Rachael Podruchny · Vylla HomeREIN MLS #10657384
$349,000Pleasant Grove3365 Benefit RdChesapeake, VA 233222 bd1 ba1,230 sqftListing courtesy of Jodi Bolling · Wainwright Real EstateREIN MLS #10657263
$334,900Brighton Park At Greenbrier1519 Pucknall Dr #3Chesapeake, VA 233203 bd2.1 ba1,862 sqftListing courtesy of Holly Long · The Real Estate GroupREIN MLS #10657528
$309,900Norfolk Highlands1507 Linden AveChesapeake, VA 233253 bd2 ba1,212 sqftListing courtesy of Ronald Sawyer · RE/MAX PrimeREIN MLS #10657054
$340,000Reunion4356 Pickney LaneChesapeake, VA 233243 bd2.1 ba1,760 sqftListing courtesy of Elizabeth Baroody · SerhantREIN MLS #10657201
Showing 1–60 of 234
Homes for sale are listed first, newest listings first; homes under contract follow.
Changes daily
Price cuts this week: Chesapeake homes from $300,000 to $400,000
Price reduced (57)
57 of 158 listings for sale have had a price cut.
Price reduced$320,000Branford Square At Greenbrierwas$345,0001509 Waitsel Dr #206Chesapeake, VA 233202 bd2 ba1,327 sqftListing courtesy of Jermaine Anderson · KW Coastal Virginia ChesapeakeREIN MLS #10650907
Price reduced$330,000Bowers Hillwas$350,0004733 Sondej AveChesapeake, VA 233213 bd1 ba988 sqftListing courtesy of Tyler Keffer · Keffer RealtyREIN MLS #10648999
Price reduced$359,000Great Bridgewas$380,000716 Hillwell Rd #BChesapeake, VA 233223 bd2 ba1,356 sqftListing courtesy of Jeremy Caleb Johnson · Long & Foster Real Estate Inc.REIN MLS #10647804
Price reduced$379,900Creekwoodwas$399,9002609 Mossgate CtChesapeake, VA 233234 bd2.1 ba2,203 sqftListing courtesy of Susan Jenkins · Better Homes & Gdns Ntv Am GrpREIN MLS #10652642
Price reduced$379,900Tallwoodwas$399,900620 Emerald CtChesapeake, VA 233204 bd2.1 ba1,917 sqftListing courtesy of Rachael Podruchny · Vylla HomeREIN MLS #10654385
Price reduced$320,000Hadley Park At Greenbrierwas$335,0001440 Rollesby WayChesapeake, VA 233203 bd2.1 ba1,870 sqftListing courtesy of Marie Banks · Swell Real Estate CoREIN MLS #10651374
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+17 lots | 2 | 901 sqft | 1957 | Est. payment up to $1,027/mo | See all 31 listings → |
| $200K–$300K | 103+12 lots | 3 | 1,257 sqft | 1985 | Est. payment $1,284/mo | See all 115 listings → |
| $300K–$400K | 156+2 lots | 3 | 1,588 sqft | 1984 | Est. payment $1,798/mo | Shown on this page |
| $400K–$500K | 127+7 lots | 4 | 2,033 sqft | 1995 | Est. payment $2,311/mo | See all 134 listings → |
| $500K–$750K | 267+5 lots | 4 | 2,642 sqft | 2016 | Est. payment $3,210/mo | See all 272 listings → |
| Over $750K | 90+6 lots | 5 | 3,240 sqft | 2026 | Est. payment from $3,852/mo | See all 96 listings → |
Market snapshot
Chesapeake homes from $300,000 to $400,000: market snapshot, October 2026
Of the 158 listings for sale in Chesapeake from $300,000 to $400,000, 57 (36%) have had a price cut, and another 76 are under contract. The median active listing has been on the market 12 days (REIN).
For sale now
- Median price per sq ft
- $220
- Under contract
- 76
- With a price cut
- 5736% of homes for sale
Recently sold
- Homes sold
- 602
- Median sold price
- $355,000
- Median days on market (REIN)
- 15 days
- Median sold price per sq ft
- $222
Closed sales from REIN MLS, March 2026 – September 2026.
Chesapeake housing market trends →Chesapeake market report PDF →
Data: REIN MLS, October 27, 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 $300,000 to $400,000: FAQ
How many homes are for sale in Chesapeake, VA from $300,000 to $400,000?
As of October 27, 2026, REIN MLS shows 156 homes for sale in Chesapeake from $300,000 to $400,000, plus 2 lots. Another 76 listings are under contract. Of the 158 listings for sale, 27 have been listed since October 21 and 57 have had a price cut.
What do homes from $300,000 to $400,000 in Chesapeake look like?
The median list price of the 158 listings for sale in Chesapeake from $300,000 to $400,000, 2 lots included, is $349,950 as of October 27, 2026. The typical home has 3 bedrooms and about 1,588 sq ft, and was built in 1984. The median list price per square foot is $220.
How fast do homes from $300,000 to $400,000 sell in Chesapeake?
From March 2026 through September 2026, 602 homes in Chesapeake sold from $300,000 to $400,000 on REIN MLS, at a median sold price of $355,000. The median closed sale was on the market 15 days (REIN).
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