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

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

104 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 2,044 sq ft, and was built in 2000.

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 102$300K–$400K 141$500K–$750K 274Over $750K 101Condos & townhomes 160New construction 193Waterfront 43Land & lots 74On this pageMarketContactFAQ

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

(+77 under contract)
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Price cuts this week: Chesapeake homes from $400,000 to $500,000

Price reduced (40)

40 of 109 listings for sale have had a price cut.

Price ranges

Chesapeake, VA homes for sale by price range

Medians of active REIN MLS listings, October 6, 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+47 lots2960 sqft1978Est. payment up to $1,027/mo
$200K–$300K91+11 lots31,244 sqft1982Est. payment $1,284/moSee all 102 listings →
$300K–$400K140+1 lot31,602 sqft1982Est. payment $1,798/moSee all 141 listings →
$400K–$500K104+5 lots42,044 sqft2000Est. payment $2,311/moShown on this page
$500K–$750K270+4 lots42,616 sqft2016Est. payment $3,210/moSee all 274 listings →
Over $750K95+6 lots53,233 sqft2026Est. payment from $3,852/moSee all 101 listings →

Market snapshot

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

Of the 109 listings for sale in Chesapeake from $400,000 to $500,000, 40 (37%) have had a price cut, and another 77 are under contract. The median active listing has been on the market 22 days (REIN).

For sale now

Median price per sq ft
$225
Under contract
77
With a price cut
4037% of homes for sale

Recently sold

Homes sold
467
Median sold price
$446,900
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 6, 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 6, 2026, REIN MLS shows 104 homes for sale in Chesapeake from $400,000 to $500,000, plus 5 lots. Another 77 listings are under contract. Of the 109 listings for sale, 20 have been listed since September 30 and 40 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 109 listings for sale in Chesapeake from $400,000 to $500,000, 5 lots included, is $449,900 as of October 6, 2026. The typical home has 4 bedrooms and about 2,044 sq ft, and was built in 2000. 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, 467 homes in Chesapeake sold from $400,000 to $500,000 on REIN MLS, at a median sold price of $446,900. The median closed sale was on the market 14 days (REIN).

Market snapshot and recent sales →

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