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

126 homes for sale in Chesapeake, VA from $400,000 to $500,000, plus 6 lots, from REIN MLS · Listing data as of Oct 10, 5:10 PM ET (syncs every 2 minutes)

126 homes and 6 lots are for sale in Chesapeake from $400,000 to $500,000 today, at a median list price of $450,000. The typical home has 4 bedrooms and about 2,034 sq ft, and was built in 1997.

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 byUnder $200K 56$200K–$300K 106$300K–$400K 147$500K–$750K 282Over $750K 102Condos & townhomes 178New construction 203Waterfront 44Land & lots 72On this pageMarketContactFAQ

126 Chesapeake homes and 6 lots for sale in this price range right now

(+72 under contract)
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Homes for sale are listed first, newest listings first; homes under contract follow.

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Changes daily

Price cuts and open houses this week: Chesapeake homes from $400,000 to $500,000

Price reduced (46)

46 of 132 listings for sale have had a price cut.

Open houses this week (10)

10 open house sessions at 10 listings, Oct 10–17.

Price ranges

Chesapeake, VA homes for sale by price range

Medians of active REIN MLS listings, October 10, 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 $200K14+42 lots2928 sqft1978Est. payment up to $1,027/moSee all 56 listings →
$200K–$300K94+12 lots31,249 sqft1983Est. payment $1,284/moSee all 106 listings →
$300K–$400K146+1 lot31,580 sqft1980Est. payment $1,798/moSee all 147 listings →
$400K–$500K126+6 lots42,034 sqft1997Est. payment $2,311/moShown on this page
$500K–$750K277+5 lots42,620 sqft2017Est. payment $3,210/moSee all 282 listings →
Over $750K96+6 lots53,226 sqft2026Est. payment from $3,852/moSee all 102 listings →

Market snapshot

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

Of the 132 listings for sale in Chesapeake from $400,000 to $500,000, 46 (35%) have had a price cut, and another 72 are under contract. The median active listing has been on the market 16 days (REIN).

For sale now

Median price per sq ft
$225
Under contract
72
With a price cut
4635% of homes for sale

Recently sold

Homes sold
468
Median sold price
$446,450
Median days on market (REIN)
14 days
Median sold price per sq ft
$228

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

Chesapeake housing market trends →Chesapeake market report PDF →

Data: REIN MLS, October 10, 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 October 10, 2026, REIN MLS shows 126 homes for sale in Chesapeake from $400,000 to $500,000, plus 6 lots. Another 72 listings are under contract. Of the 132 listings for sale, 33 have been listed since October 4 and 46 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 132 listings for sale in Chesapeake from $400,000 to $500,000, 6 lots included, is $450,000 as of October 10, 2026. The typical home has 4 bedrooms and about 2,034 sq ft, and was built in 1997. The median list price per square foot is $225.

Chesapeake housing market trends →

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

From March 2026 through September 2026, 468 homes in Chesapeake sold from $400,000 to $500,000 on REIN MLS, at a median sold price of $446,450. The median closed sale was on the market 14 days (REIN).

Market snapshot and recent sales →

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