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Homes for Sale in Chesapeake, VA: $300,000 to $400,000

145 homes for sale in Chesapeake, VA from $300,000 to $400,000, plus 1 lot, from REIN MLS · Listing data as of Oct 10, 4:10 PM ET (syncs every 2 minutes)

145 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 1,582 sq ft, and was built in 1981.

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$400K–$500K 132$500K–$750K 282Over $750K 102Condos & townhomes 178New construction 203Waterfront 44Land & lots 72On this pageMarketContactFAQ

145 Chesapeake homes and 1 lot for sale in this price range right now

(+81 under contract)
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Changes daily

Price cuts this week: Chesapeake homes from $300,000 to $400,000

Price reduced (57)

57 of 146 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 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–$400K145+1 lot31,582 sqft1981Est. payment $1,798/moShown on this page
$400K–$500K126+6 lots42,034 sqft1997Est. payment $2,311/moSee all 132 listings →
$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 $300,000 to $400,000: market snapshot, October 2026

Of the 146 listings for sale in Chesapeake from $300,000 to $400,000, 57 (39%) have had a price cut, and another 81 are under contract. The median active listing has been on the market 17 days (REIN).

For sale now

Median price per sq ft
$222
Under contract
81
With a price cut
5739% of homes for sale

Recently sold

Homes sold
601
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 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 $300,000 to $400,000: FAQ

How many homes are for sale in Chesapeake, VA from $300,000 to $400,000?

As of October 10, 2026, REIN MLS shows 145 homes for sale in Chesapeake from $300,000 to $400,000, plus 1 lot. Another 81 listings are under contract. Of the 146 listings for sale, 16 have been listed since October 4 and 57 have had a price cut.

All Chesapeake homes for sale →

What do homes from $300,000 to $400,000 in Chesapeake look like?

The median list price of the 146 listings for sale in Chesapeake from $300,000 to $400,000, 1 lot included, is $349,900 as of October 10, 2026. The typical home has 3 bedrooms and about 1,582 sq ft, and was built in 1981. The median list price per square foot is $222.

Chesapeake housing market trends →

How fast do homes from $300,000 to $400,000 sell in Chesapeake?

From March 2026 through September 2026, 601 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).

Market snapshot and recent sales →

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