Investment Properties & Fixer-Uppers for Sale in Chesapeake, VA

There are currently 201 active investment properties for sale in Chesapeake, VA on DealSherpa — fix-and-flip, BRRRR, and wholesale deals with the numbers already run. Asking prices start around $147,900, average $337,709, with an average after-repair value of $328,687. Addresses unlock with a DealSherpa subscription ($99/mo).

Investment property for sale in Chesapeake, VADeal Score 54
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$190,000

ARV

$254,928

Max Offer

$188,469

2 bd2 ba1,254 sqft
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Investment property for sale in Chesapeake, VADeal Score 49
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$314,000

ARV

$415,750

Max Offer

$333,999

5 bd3 ba2,354 sqft$19,999 spread
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Investment property for sale in Chesapeake, VADeal Score 49
Address hidden

Chesapeake, VA · Detached

Asking

$225,000

ARV

$275,000

Max Offer

$208,129

2 bd1 ba890 sqft
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Investment property for sale in Chesapeake, VADeal Score 49
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$270,000

ARV

$335,250

Max Offer

$242,828

3 bd2 ba1,276 sqft
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Investment property for sale in Chesapeake, VADeal Score 48
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$249,000

ARV

$310,000

Max Offer

$239,277

3 bd2 ba1,305 sqft
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Investment property for sale in Chesapeake, VADeal Score 48
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$260,000

ARV

$326,450

Max Offer

$253,916

3 bd1 ba1,500 sqft
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Investment property for sale in Chesapeake, VADeal Score 48
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$279,900

ARV

$361,250

Max Offer

$234,465

4 bd1 ba1,484 sqft
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Investment property for sale in Chesapeake, VADeal Score 47
Address hidden

Chesapeake, VA 23321 · Attached

Asking

$199,000

ARV

$244,500

Max Offer

$178,796

2 bd1 ba1,262 sqft
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Investment property for sale in Chesapeake, VADeal Score 47
Address hidden

Chesapeake, VA 23321 · Attached

Asking

$223,500

ARV

$272,500

Max Offer

$204,932

2 bd1 ba1,186 sqft
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Investment property for sale in Chesapeake, VADeal Score 46
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$235,000

ARV

$281,250

Max Offer

$212,712

2 bd1 ba1,292 sqft
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Investment property for sale in Chesapeake, VADeal Score 46
Address hidden

Chesapeake, VA · Attached

Asking

$214,000

ARV

$260,500

Max Offer

$193,082

3 bd1.5 ba1,436 sqft
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Investment property for sale in Chesapeake, VADeal Score 46
Address hidden

Chesapeake, VA 23320 · Detached

Asking

$285,000

ARV

$340,000

Max Offer

$266,747

3 bd2 ba1,402 sqft
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Investment property for sale in Chesapeake, VADeal Score 46
Address hidden

Chesapeake, VA 23321 · Attached

Asking

$150,000

ARV

$178,450

Max Offer

$118,580

2 bd2 ba960 sqft
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Investment property for sale in Chesapeake, VADeal Score 45
Address hidden

Chesapeake, VA 23322 · Attached

Asking

$239,900

ARV

$280,000

Max Offer

$177,089

2 bd1 ba1,141 sqft
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Investment property for sale in Chesapeake, VADeal Score 45
Address hidden

Chesapeake, VA 23321 · Attached

Asking

$229,900

ARV

$265,000

Max Offer

$197,992

2 bd1 ba1,186 sqft
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Investment property for sale in Chesapeake, VADeal Score 45
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$220,000

ARV

$247,000

Max Offer

$160,735

3 bd1 ba921 sqft
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Investment property for sale in Chesapeake, VADeal Score 45
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$220,000

ARV

$246,000

Max Offer

$159,950

2 bd1 ba874 sqft
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Investment property for sale in Chesapeake, VADeal Score 44
Address hidden

Chesapeake, VA 23320 · Detached

Asking

$214,900

ARV

$237,250

Max Offer

$172,870

2 bd1 ba1,000 sqft
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Investment property for sale in Chesapeake, VADeal Score 44
Address hidden

Chesapeake, VA · Attached

Asking

$245,000

ARV

$281,250

Max Offer

$200,886

2 bd2.5 ba1,254 sqft
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Investment property for sale in Chesapeake, VADeal Score 44
Address hidden

Chesapeake, VA · Attached

Asking

$269,000

ARV

$302,750

Max Offer

$232,828

3 bd2.5 ba1,218 sqft
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Investment property for sale in Chesapeake, VADeal Score 44
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$216,000

ARV

$244,500

Max Offer

$159,162

4 bd2 ba1,173 sqft
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Investment property for sale in Chesapeake, VADeal Score 44
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$297,000

ARV

$346,750

Max Offer

$272,366

4 bd2 ba1,612 sqft
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Investment property for sale in Chesapeake, VADeal Score 43
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$264,999

ARV

$301,000

Max Offer

$230,525

4 bd2 ba1,447 sqft
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Investment property for sale in Chesapeake, VADeal Score 43
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$399,900

ARV

$470,000

Max Offer

$372,709

4 bd2 ba2,203 sqft
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Investment property for sale in Chesapeake, VADeal Score 43
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$252,000

ARV

$294,500

Max Offer

$197,511

4 bd2 ba1,659 sqft
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Investment property for sale in Chesapeake, VADeal Score 43
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$345,900

ARV

$391,550

Max Offer

$294,256

4 bd2 ba1,500 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$229,900

ARV

$254,000

Max Offer

$187,294

3 bd1 ba1,360 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$195,000

ARV

$211,750

Max Offer

$148,784

2 bd1 ba1,164 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$189,900

ARV

$199,500

Max Offer

$138,356

2 bd1 ba860 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$325,000

ARV

$367,500

Max Offer

$291,740

3 bd1 ba1,554 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$284,900

ARV

$314,200

Max Offer

$243,345

3 bd1 ba1,244 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$279,000

ARV

$310,000

Max Offer

$239,208

3 bd1 ba1,328 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$275,000

ARV

$313,000

Max Offer

$241,100

4 bd1 ba1,624 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$259,900

ARV

$272,495

Max Offer

$190,931

3 bd1 ba875 sqft
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Investment property for sale in Chesapeake, VADeal Score 42
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$230,000

ARV

$255,000

Max Offer

$188,536

2 bd2.5 ba1,254 sqft
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Investment property for sale in Chesapeake, VADeal Score 41
Address hidden

Chesapeake, VA 23321 · Attached

Asking

$147,900

ARV

$144,950

Max Offer

$87,769

2 bd1 ba897 sqft
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Investment property for sale in Chesapeake, VADeal Score 41
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$275,000

ARV

$303,750

Max Offer

$232,720

3 bd2 ba1,564 sqft
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Investment property for sale in Chesapeake, VADeal Score 41
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$325,000

ARV

$347,500

Max Offer

$259,267

3 bd1 ba1,233 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$399,000

ARV

$449,435

Max Offer

$364,506

4 bd2 ba2,576 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$317,000

ARV

$218,750

Max Offer

$139,540

3 bd1 ba1,431 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$263,900

ARV

$255,000

Max Offer

$176,447

2 bd2 ba1,304 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$225,000

ARV

$210,399

Max Offer

$148,307

4 bd1 ba905 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$225,000

ARV

$213,750

Max Offer

$150,629

4 bd1 ba1,166 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$268,000

ARV

$230,000

Max Offer

$163,427

5 bd3 ba1,916 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23321 · Detached

Asking

$383,000

ARV

$408,750

Max Offer

$329,653

4 bd2 ba1,640 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$434,999

ARV

$466,935

Max Offer

$380,299

5 bd3 ba2,710 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23321 · Detached

Asking

$352,000

ARV

$319,500

Max Offer

$246,590

3 bd2 ba1,800 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$349,900

ARV

$361,250

Max Offer

$285,652

4 bd2 ba1,656 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$349,800

ARV

$372,450

Max Offer

$294,541

5 bd2 ba2,150 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23322 · Attached

Asking

$295,000

ARV

$287,000

Max Offer

$218,499

2 bd1 ba1,136 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23321 · Detached

Asking

$340,000

ARV

$337,500

Max Offer

$264,255

3 bd2 ba1,462 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23320 · Attached

Asking

$315,000

ARV

$264,750

Max Offer

$197,265

2 bd2 ba1,352 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$500,000

ARV

$575,000

Max Offer

$478,933

5 bd3 ba3,166 sqft
Unlock address → Start free trial
Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23324 · Detached

Asking

$314,700

ARV

$298,750

Max Offer

$228,285

3 bd2 ba1,500 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$325,000

ARV

$336,750

Max Offer

$262,946

3 bd1 ba1,668 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$299,900

ARV

$297,500

Max Offer

$227,486

3 bd1 ba1,380 sqft
Unlock address → Start free trial
Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23325 · Detached

Asking

$287,000

ARV

$291,000

Max Offer

$222,272

3 bd1 ba1,112 sqft
Unlock address → Start free trial
Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23321 · Detached

Asking

$315,000

ARV

$248,500

Max Offer

$182,459

3 bd1 ba1,275 sqft
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Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23322 · Detached

Asking

$469,900

ARV

$458,778

Max Offer

$375,312

4 bd2 ba1,852 sqft
Unlock address → Start free trial
Investment property for sale in Chesapeake, VADeal Score 40
Address hidden

Chesapeake, VA 23323 · Detached

Asking

$410,000

ARV

$382,500

Max Offer

$304,796

4 bd3 ba1,830 sqft
Unlock address → Start free trial

See the addresses in Chesapeake, VA

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Buying investment property in Chesapeake, VA

DealSherpa underwrites every Chesapeake listing the day it hits the MLS — pulling comparable sales to estimate ARV, estimating rehab cost, and calculating the maximum offer that still leaves room for profit. Instead of manually running comps on dozens of listings, you see Chesapeake's best fix-and-flip and BRRRR opportunities ranked by spread, with the exact address and full analysis one click away.