New
$344,900Dunedin
3336 Kinsington Dr
Chesapeake, VA 23321
3 bd2 ba1,375 sqft
Listing courtesy of Nikki Bowen · The Bowen GroupREIN MLS #10653715
Homes for Sale in Chesapeake, VA: $300,000 to $400,000
129 homes for sale in Chesapeake, VA from $300,000 to $400,000, plus 1 lot, from REIN MLS · Listing data as of Sep 16, 2:10 PM ET (syncs every 2 minutes)
129 homes and 1 lot are for sale in Chesapeake from $300,000 to $400,000 today, at a median list price of $349,900. The typical home has 3 bedrooms and about 1,640 sq ft, and was built in 1987.
Tom & Dariya Milan, RealtorsBrokered by LPT Realty · Call or text (757) 777-7577
- For sale now130
- Median list price$349,900
- New this week27
- Median days on market (REIN, active listings)18 days
Source: REIN MLS. These figures include lots and exclude homes under contract.
129 Chesapeake homes and 1 lot for sale in this price range right now
(+102 under contract)Skip the 60 listingsSkip to this week's listings
New$399,900Mill Creek753 Willow Bend Dr
Chesapeake, VA 23323
4 bd2 ba2,053 sqft
Listing courtesy of Yvonne Covey · A Better Way Realty Inc.REIN MLS #10653770
New$349,900Raleigh Heights1013 McKinley Ave
Chesapeake, VA 23324
1,652 sqft
Listing courtesy of Conner Walters · World Class Realty & Prop MgmtREIN MLS #10653787
Coming Soon$335,0001115 Killington Arch
Chesapeake, VA 23320
3 bd2.1 ba1,585 sqft
Listing courtesy of Amanda Schnepper · BHHS RW Towne RealtyREIN MLS #10653708
New$305,000Kings Pointe At Western Branch2453 Leytonstone Dr
Chesapeake, VA 23321
2 bd2.1 ba1,870 sqft
Listing courtesy of Joshua Wilborne · Own Real Estate LLCREIN MLS #10653755
Coming Soon$325,000Crestwood5341 Libertyville Rd
Chesapeake, VA 23320
3 bd2 ba1,215 sqft
Listing courtesy of Warren Neal · Real Broker LLCREIN MLS #10652746
New$390,000Jolliff Landing Townhouses5235 Lombard St
Chesapeake, VA 23321
3 bd2.1 ba1,894 sqft
Listing courtesy of Jay Hassell · Keller Williams Realty Twn CtrREIN MLS #10653106
New$399,000Chadswyck Terrace4207 Coffman Blvd
Chesapeake, VA 23321
4 bd2 ba1,468 sqft
Listing courtesy of Bethany White · BHHS RW Towne RealtyREIN MLS #10653672
New$339,000Norfolk Highlands1604 Myrtle Ave
Chesapeake, VA 23325
4 bd2 ba1,584 sqft
Listing courtesy of Julian Rivera · Iron Valley Real Est NorfolkREIN MLS #10653422
New$380,000Cedar Crossing1216 Club Point Dr
Chesapeake, VA 23322
3 bd2.1 ba1,528 sqft
Listing courtesy of Michael Miller · RE/MAX AllegianceREIN MLS #10653557
New$375,000Avalon Park916 Redstart Ave
Chesapeake, VA 23324
3 bd2 ba1,744 sqft
Listing courtesy of Kala DiCiero · The Real Estate GroupREIN MLS #10653529
New$329,900Sunrise Hills2205 Hilton Ct
Chesapeake, VA 23324
4 bd2.1 ba1,920 sqft
Listing courtesy of Cyndi Houser · Better Homes & Gdns Ntv Am GrpREIN MLS #10653097
Coming Soon$357,000Camelot1128 Sir Galahad Dr
Chesapeake, VA 23323
3 bd2.1 ba1,366 sqft
Listing courtesy of Alex Sanchez · Real Broker LLCREIN MLS #10653187
New$307,000Sunrise Hills2209 Hilton Ct
Chesapeake, VA 23324
3 bd2.1 ba1,777 sqft
Listing courtesy of Jonathan Melvin · Benham Real Estate LLCREIN MLS #10653540
NewOpen Sat 12–2 PM$310,000Riverwalk719 Creekside Cres
Chesapeake, VA 23320
3 bd2.1 ba1,400 sqft
Listing courtesy of Tawni Walker · Atlantic Realty&Prop Mgmt GrpREIN MLS #10653124
New$375,000Raleigh Heights1431 Oliver Ave
Chesapeake, VA 23324
4 bd3 ba1,972 sqft
Listing courtesy of Taylor Bishop · 757 RealtyREIN MLS #10652948
New$360,000Hampshires1486 Otterbourne Cir
Chesapeake, VA 23320
3 bd2.1 ba1,804 sqft
Listing courtesy of Kim Mills Kirkby · The Real Estate GroupREIN MLS #10652752
New$365,000Cedar Grove Acres1308 Sunnybrook Ter
Chesapeake, VA 23321
4 bd3 ba2,200 sqft
Listing courtesy of Christopher Iturbe · Iron Valley Real Estate HRREIN MLS #10653190
New$345,000Belvin Heights815 Rutledge Rd
Chesapeake, VA 23320
3 bd1.1 ba1,224 sqft
Listing courtesy of Angela Kennedy · 1st Class Real Estate IntegrityREIN MLS #10653235
NewOpen Sat 2–4 PM$375,000Portlock Terrace4009 1st St
Chesapeake, VA 23324
4 bd3 ba1,972 sqft
Listing courtesy of Teilor Burnett · Own Real Estate LLCREIN MLS #10653176
NewOpen Sat 11 AM–1 PM$304,999Ardmore2801 Southport Ave.
Chesapeake, VA 23324
3 bd1 ba1,500 sqft
Listing courtesy of Ryan Kilmon · A Better Way Realty Inc.REIN MLS #10653156
NewOpen Thu 5–7 PM$337,000Harbor Watch Condo5 Harbor Watch Dr #405
Chesapeake, VA 23320
3 bd2 ba1,762 sqft
Listing courtesy of Angela Stafilidis · Iron Valley Real Estate HRREIN MLS #10651901
NewOpen Sat 11 AM–1 PM$375,000Riverwalk620 Estates Way #120
Chesapeake, VA 23320
3 bd2.1 ba1,831 sqft
Listing courtesy of Katie Howlett · BHHS RW Towne RealtyREIN MLS #10652230
NewOpen Sat 10–4 PM$360,000Crestwood Manor726 Marcus St St
Chesapeake, VA 23320
4 bd4 ba1,612 sqft
Listing courtesy of Liang Zhen · Keller Williams Realty Twn CtrREIN MLS #10652729
New$374,900Coleman Farms2429 Fieldsway Dr
Chesapeake, VA 23320
3 bd2.1 ba1,669 sqft
Listing courtesy of Terrance Boyle · Iron Valley Real Estate PrestigeREIN MLS #10653094
New$327,000Indian River Estates1505 Sparrow Rd
Chesapeake, VA 23325
4 bd1 ba1,264 sqft
Listing courtesy of Mary Jackowell · Family First Realty IncREIN MLS #10653029
NewOpen Sun 1–3 PM$399,000Western Branch4353 Shorewood Dr
Chesapeake, VA 23321
3 bd2 ba1,800 sqft
Listing courtesy of Tracie Gaskins · Howard Hanna Real Estate Svcs.REIN MLS #10652696
New$369,000Brentwood1333 Boxwood Dr
Chesapeake, VA 23323
3 bd1.1 ba1,600 sqft
Listing courtesy of Jay Kotchka · BHHS RW Towne RealtyREIN MLS #10652758
New$385,000South Norfolk909 Portland St
Chesapeake, VA 23324
4 bd2.1 ba2,196 sqft
Listing courtesy of Cari Rausch · Iron Valley Real Estate HRREIN MLS #10652567
$399,900Warrington Hall1152 Chatham Ln #14
Chesapeake, VA 23320
3 bd2.1 ba1,776 sqft
Listing courtesy of Frances Ward · Triumph RealtyREIN MLS #10652491
$375,000Providence Square2532 Lanier St
Chesapeake, VA 23324
4 bd3.1 ba1,947 sqft
Listing courtesy of Joel Dinse · A Better Way Realty Inc.REIN MLS #10651581
$310,000Sheridan Heights1535 Lyons Ave
Chesapeake, VA 23324
3 bd1.1 ba1,620 sqft
Listing courtesy of Joshua Britt · Prodigy RealtyREIN MLS #10652158
$399,999Warrington Hall1117 Winsford Ln
Chesapeake, VA 23320
3 bd2.1 ba1,776 sqft
Listing courtesy of Lexi Pace · RE/MAX AllianceREIN MLS #10652128
$345,000Branford Square At Greenbrier1509 Waitsel Dr #206
Chesapeake, VA 23320
2 bd2 ba1,327 sqft
Listing courtesy of Jermaine Anderson · KW Coastal Virginia ChesapeakeREIN MLS #10650907
$325,000The Grove At The Arboretum650 Lacy Oak Dr
Chesapeake, VA 23320
2 bd2.1 ba1,870 sqft
Listing courtesy of Stephanie Hynes · Redefy Real EstateREIN MLS #10651928
$319,900Branford Square At Greenbrier1505 Waitsel Dr #304
Chesapeake, VA 23320
2 bd2 ba1,327 sqft
Listing courtesy of Shaquanna Parris · Iron Valley Real Est NorfolkREIN MLS #10651771
Price reduced$382,500Portlock Terracewas
$385,0002415 Chesapeake Cir
Chesapeake, VA 23324
4 bd2 ba1,600 sqft
Listing courtesy of Steffanie Battles · 1st Class Real Estate FlagshipREIN MLS #10651751
$349,900Tanglewood313 Sparrow Rd
Chesapeake, VA 23325
3 bd1 ba1,460 sqft
Listing courtesy of Kelly Jaworsky · Howard Hanna Real Estate Svcs.REIN MLS #10651732
Price reduced$344,000Hadley Park At Greenbrierwas
$345,0001561 Rollesby Way
Chesapeake, VA 23320
3 bd2.1 ba1,800 sqft
Listing courtesy of Angela Kennedy · 1st Class Real Estate IntegrityREIN MLS #10651317
$335,000Hadley Park At Greenbrier1440 Rollesby Way
Chesapeake, VA 23320
3 bd2.1 ba1,870 sqft
Listing courtesy of Marie Banks · Swell Real Estate CoREIN MLS #10651374
$342,000Norfolk Highlands1319 Laurel Ave
Chesapeake, VA 23320
3 bd2 ba1,222 sqft
Listing courtesy of Carolyne Nelson · Atkinson RealtyREIN MLS #10651307
$349,900The Grove2044 Mango St
Chesapeake, VA 23321
2 bd2.1 ba1,495 sqft
Listing courtesy of Lisa Kyriakides · Corinth Realty LLCREIN MLS #10651295
$309,900Hadley Park At Greenbrier1519 Rollesby Way
Chesapeake, VA 23320
3 bd2.1 ba1,870 sqft
Listing courtesy of Scott See · AtCoastal RealtyREIN MLS #10651219
$399,900Oak Manor624 Rock Dr
Chesapeake, VA 23323
4 bd2 ba2,460 sqft
Listing courtesy of Matthew Salway · Iron Valley Real Estate HRREIN MLS #10651224
Lot / land$325,000Pleasant Grove11.8 Acres Ballahack Rd
Chesapeake, VA 23322
Listing courtesy of Walter Graham · MOP Land and Farms RealtyREIN MLS #10650830
Price reduced$379,900South Norfolkwas
$389,9001435 Seaboard Ave
Chesapeake, VA 23324
3 bd2.1 ba1,530 sqft
Listing courtesy of Kim Wilkins · RE/MAX UltraREIN MLS #10650855
$379,999Camelot832 Parapet Rd
Chesapeake, VA 23323
4 bd2 ba1,762 sqft
Listing courtesy of Cristian Juarez · ONYX Realty Professionals LLCREIN MLS #10650851
$305,000Seminole Park1605 Laurel Ave
Chesapeake, VA 23325
3 bd1.1 ba1,207 sqft
Listing courtesy of Tracy Thayer · Own Real Estate LLCREIN MLS #10650769
$334,900The Grove4987 Boone Rd
Chesapeake, VA 23321
2 bd2.1 ba1,464 sqft
Listing courtesy of Lisa Kyriakides · Corinth Realty LLCREIN MLS #10650732
Price reduced$369,000Indian River Estateswas
$379,0001109 Santeetlah Ave
Chesapeake, VA 23325
4 bd2 ba1,725 sqft
Listing courtesy of Danielle Urrutia · Swell Realty CoREIN MLS #10650746
$315,000Deep Creek Shores504 Plummer Dr
Chesapeake, VA 23320
3 bd1 ba1,094 sqft
Listing courtesy of Caitlin Dress · COVA Home RealtyREIN MLS #10650561
$325,130Grayson Commons1540 Eldwick Drive #103
Chesapeake, VA 23320
2 bd2 ba1,355 sqft
Listing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10650599
$310,130Grayson Commons1540 Eldwick Drive #201
Chesapeake, VA 23320
2 bd2 ba1,386 sqft
Listing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10650593
$345,130Grayson Commons1540 Eldwick Drive #101
Chesapeake, VA 23320
2 bd2 ba1,386 sqft
Listing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10650588
$320,130Grayson Commons1540 Eldwick Drive #302
Chesapeake, VA 23320
2 bd2 ba1,386 sqft
Listing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10650581
Price reduced$375,000Dunedinwas
$380,0003116 Dunworken Dr
Chesapeake, VA 23321
4 bd2 ba1,612 sqft
Listing courtesy of Gabrielle Riggins-Royals · Own Real Estate LLCREIN MLS #10650484
$400,000Western Branch4908 Portsmouth Blvd
Chesapeake, VA 23321
3 bd1.1 ba1,421 sqft
Listing courtesy of Denise Winslow · CENTURY 21 Nachman RealtyREIN MLS #10650403
$399,900South Norfolk2218 Vicker Ave
Chesapeake, VA 23324
4 bd2 ba2,692 sqft
Listing courtesy of Julie Perkins · Swell Realty CoREIN MLS #10650357
Price reduced$399,500Norfolk Highlandswas
$399,9991129 Hazel Ave
Chesapeake, VA 23325
4 bd3.1 ba2,000 sqft
Listing courtesy of Angela Kennedy · 1st Class Real Estate IntegrityREIN MLS #10649784
Open Sun 12–5 PM$330,900The Grove4985 Boone Rd
Chesapeake, VA 23321
2 bd2.1 ba1,464 sqft
Listing courtesy of Lisa Kyriakides · Corinth Realty LLCREIN MLS #10650280
Showing 1–60 of 232
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 $300,000 to $400,000
Price reduced (48)
48 of 130 listings for sale have had a price cut.
Price reduced$314,000Deep Creekwas
$380,0001417 Gust Ln
Chesapeake, VA 23323
5 bd3.1 ba2,354 sqft
Listing courtesy of Candice Myers · BHHS RW Towne RealtyREIN MLS #10644206
Price reduced$325,000Harbor Watch Condowas
$359,9005 Harbor Watch Dr #413
Chesapeake, VA 23320
3 bd2 ba1,786 sqft
Listing courtesy of Cosette Lambourne · Real Broker LLCREIN MLS #10648847
Price reduced$399,900Grayson Commonswas
$437,400670 Allery Rd
Chesapeake, VA 23320
2 bd2.1 ba1,847 sqft
Listing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10641732
Price reduced$394,900Grayson Commonswas
$427,400674 Allery Rd
Chesapeake, VA 23320
2 bd2.1 ba1,847 sqft
Listing courtesy of Clarice Savereux · Dragas Companies Realty IncREIN MLS #10641729
Price reduced$325,000Wilmund Placewas
$345,9004111 Williamson St
Chesapeake, VA 23324
3 bd2 ba1,200 sqft
Listing courtesy of Erika Miller · NextHome Beyond KeysREIN MLS #10647096
Price reduced$339,000Riverside Parkwas
$349,9004201 Nautilus Ave
Chesapeake, VA 23325
3 bd2 ba1,186 sqft
Listing courtesy of Rene Bagne · Creed RealtyREIN MLS #10646933
Open houses this week (11)
12 open house sessions at 11 listings, Sep 16–23.
Price reducedOpen Sat 1–3 PM$314,999Gracie Parkwas
$320,000340 Gracie Rd
Chesapeake, VA 23325
4 bd1.1 ba1,740 sqft
Listing courtesy of Ronald Sawyer · RE/MAX PrimeREIN MLS #10649849
Open Sun 12–2 PM$310,000Harbor Watch Condo4 Harbor Watch Dr ##520
Chesapeake, VA 23320
3 bd2 ba1,668 sqft
Listing courtesy of Gina Cross · Swell Realty CoREIN MLS #10646639
Price reducedOpen Thu 4–6 PM$397,490Deep Creekwas
$399,9903433 Martin Johnson Rd
Chesapeake, VA 23323
3 bd2 ba1,607 sqft
Listing courtesy of Ronald Sawyer · RE/MAX PrimeREIN MLS #10643999
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 | Shown on this page |
| $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 | See all 102 listings → |
Market snapshot
Chesapeake homes from $300,000 to $400,000: market snapshot, September 2026
Of the 130 listings for sale in Chesapeake from $300,000 to $400,000, 48 (37%) have had a price cut, and another 102 are under contract. The median active listing has been on the market 18 days (REIN).
For sale now
- Median price per sq ft
- $216
- Under contract
- 102
- With a price cut
- 4837% of homes for sale
Recently sold
- Homes sold
- 515
- Median sold price
- $355,000
- Median days on market (REIN)
- 14 days
- Median sold price per sq ft
- $222
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 from $300,000 to $400,000: FAQ
How many homes are for sale in Chesapeake, VA from $300,000 to $400,000?
As of September 16, 2026, REIN MLS shows 129 homes for sale in Chesapeake from $300,000 to $400,000, plus 1 lot. Another 102 listings are under contract. Of the 130 listings for sale, 27 have been listed since September 10 and 48 have had a price cut.
What do homes from $300,000 to $400,000 in Chesapeake look like?
The median list price of the 130 listings for sale in Chesapeake from $300,000 to $400,000, 1 lot included, is $349,900 as of September 16, 2026. The typical home has 3 bedrooms and about 1,640 sq ft, and was built in 1987. The median list price per square foot is $216.
How fast do homes from $300,000 to $400,000 sell in Chesapeake?
From March 2026 through August 2026, 515 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 14 days (REIN).
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