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Homes for Sale in Chesapeake, VA: $400,000 to $500,000

114 homes for sale in Chesapeake, VA from $400,000 to $500,000, plus 5 lots, from REIN MLS · Listing data as of Sep 16, 2:10 PM ET (syncs every 2 minutes)

114 homes and 5 lots are for sale in Chesapeake from $400,000 to $500,000 today, at a median list price of $449,900. The typical home has 4 bedrooms and about 2,058 sq ft, and was built in 2002.

Tom & Dariya Milan, RealtorsBrokered by LPT Realty · Call or text (757) 777-7577

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Source: REIN MLS. These figures include lots and exclude homes under contract.

Shop byShop Chesapeake homes by$200K–$300K 98$300K–$400K 130$500K–$750K 276Over $750K 102Condos & townhomes 160New construction 189Waterfront 57Land & lots 69On this pageMarketContactFAQ

114 Chesapeake homes and 5 lots for sale in this price range right now

(+86 under contract)
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Price cuts this week: Chesapeake homes from $400,000 to $500,000

Price reduced (47)

47 of 119 listings for sale have had a price cut.

Price ranges

Chesapeake, VA homes for sale by price range

Medians of active REIN MLS listings, September 16, 2026. Lots and land are counted separately and left out of the typical beds, size and year built. Est. payment is principal and interest only, 30-year fixed at 6.65% (an assumption, not a quote) with 20% down; taxes, insurance and HOA fees are extra. Estimates are for informational purposes only and do not constitute a loan offer or pre-approval. Compare local lenders: Hampton Roads lenders.
Price rangeHomes for saleTypical bedsTypical sizeTypical year builtEst. P&I / moListings
Under $200K10+41 lots21,112 sqft1977Est. payment up to $1,027/mo
$200K–$300K89+9 lots21,254 sqft1983Est. payment $1,284/moSee all 98 listings →
$300K–$400K129+1 lot31,640 sqft1987Est. payment $1,798/moSee all 130 listings →
$400K–$500K114+5 lots42,058 sqft2002Est. payment $2,311/moShown on this page
$500K–$750K269+7 lots42,600 sqft2014Est. payment $3,210/moSee all 276 listings →
Over $750K96+6 lots53,240 sqft2026Est. payment from $3,852/moSee all 102 listings →

Market snapshot

Chesapeake homes from $400,000 to $500,000: market snapshot, September 2026

Of the 119 listings for sale in Chesapeake from $400,000 to $500,000, 47 (40%) have had a price cut, and another 86 are under contract. The median active listing has been on the market 27 days (REIN).

For sale now

Median price per sq ft
$220
Under contract
86
With a price cut
4740% of homes for sale

Recently sold

Homes sold
402
Median sold price
$445,000
Median days on market (REIN)
13 days
Median sold price per sq ft
$229

Closed sales from REIN MLS, March 2026 – August 2026.

Chesapeake housing market trends →Chesapeake market report PDF →

Data: REIN MLS, September 16, 2026.

Tom and Dariya Milan

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

Call or text (757) 777-7577

What's my Chesapeake home worth? →About Tom & Dariya →

FAQ

Homes for sale in Chesapeake, VA from $400,000 to $500,000: FAQ

How many homes are for sale in Chesapeake, VA from $400,000 to $500,000?

As of September 16, 2026, REIN MLS shows 114 homes for sale in Chesapeake from $400,000 to $500,000, plus 5 lots. Another 86 listings are under contract. Of the 119 listings for sale, 19 have been listed since September 10 and 47 have had a price cut.

All Chesapeake homes for sale →

What do homes from $400,000 to $500,000 in Chesapeake look like?

The median list price of the 119 listings for sale in Chesapeake from $400,000 to $500,000, 5 lots included, is $449,900 as of September 16, 2026. The typical home has 4 bedrooms and about 2,058 sq ft, and was built in 2002. The median list price per square foot is $220.

Chesapeake housing market trends →

How fast do homes from $400,000 to $500,000 sell in Chesapeake?

From March 2026 through August 2026, 402 homes in Chesapeake sold from $400,000 to $500,000 on REIN MLS, at a median sold price of $445,000. The median closed sale was on the market 13 days (REIN).

Market snapshot and recent sales →

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