OBT insider transaction filings

Orange County Bancorp, Inc. /DE/ — 50 most recent Form 4 filings from SEC EDGAR, normalized by FilingPulse. Latest filing: 2026-09-21. Screen OBT transaction legs live →

Insider transaction summary — last 90 days

2026-06-24 to 2026-09-22, from the filings listed below: 26 Form 4 filings. Counts and totals are arithmetic on values as filed — descriptive data, not a recommendation.

By insider — same window

Open-market purchase/sale legs on non-derivative securities, grouped by the filing's reporting owner(s); joint filings appear once. Dollar totals cover priced legs only (shares × price as filed). Ordered by priced transaction value, largest first.

InsiderFilingsPurchases (P)Sales (S)Other legs
Sousa Gregory — EVP and Deputy CLO32 legs · 3,047 sh · $118,0712
Rooney Stephen — SVP, Chief Credit Officer11 leg · 1,500 sh · $58,065
Tirado Olga Luz — Director66
Rowley Richard B — Director33
HOLCOMBE GREGORY F — Director22
Keane Kevin J — Director22
Kennedy Marianna R — Director22
Rouis Jonathan F — Director22
Schiller Jon — Director22
Gilfeather Michael J — President and CEO, Director11

+2 more insiders in the window, not shown — every filing appears in the table below.

Recent Form 4 filings — Orange County Bancorp, Inc. /DE/

FiledFormInsiderReported transactionsSource
2026-09-214/ASousa Gregory — EVP and Deputy CLOGrant/award (A) @ $38.78EDGAR
2026-09-164Lesler Michael — EVP, Chief Financial OfficerGrant/award (A) @ $38.78EDGAR
2026-09-164Kennedy Marianna R — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Keane Kevin J — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164HOLCOMBE GREGORY F — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Gilfeather Michael J — President and CEO, DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Tirado Olga Luz — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Schiller Jon — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Rowley Richard B — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Rouis Jonathan F — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Morrison William D — DirectorGrant/award (A) @ $38.78EDGAR
2026-09-164Sousa Gregory — EVP and Deputy CLOGrant/award (A) @ $38.78EDGAR
2026-08-054Rooney Stephen — SVP, Chief Credit OfficerSale (S): 1,500 @ $38.71EDGAR
2026-08-034Sousa Gregory — EVP and Deputy CLOSale (S): 1,165 @ $38.75 · Sale (S): 1,882 @ $38.75EDGAR
2026-07-234Rowley Richard B — DirectorGrant/award (A) @ $37.19EDGAR
2026-07-064Rouis Jonathan F — DirectorGrant/award (A) @ $37.46EDGAR
2026-07-064Tirado Olga Luz — DirectorGrant/award (A) @ $37.46EDGAR
2026-07-064Keane Kevin J — DirectorGrant/award (A) @ $37.46EDGAR
2026-07-064Kennedy Marianna R — DirectorGrant/award (A) @ $37.46EDGAR
2026-07-064Schiller Jon — DirectorGrant/award (A) @ $37.46EDGAR
2026-07-064/ATirado Olga Luz — DirectorGrant/award (A) @ $35.35EDGAR
2026-07-064/ATirado Olga Luz — DirectorGrant/award (A) @ $32.32EDGAR
2026-07-064/ATirado Olga Luz — DirectorGrant/award (A) @ $31.29EDGAR
2026-07-064/ATirado Olga Luz — DirectorGrant/award (A) @ $28.35EDGAR
2026-07-064Rowley Richard B — DirectorGrant/award (A) @ $37.46EDGAR
2026-07-064HOLCOMBE GREGORY F — DirectorGrant/award (A) @ $37.46EDGAR
2026-06-174Tirado Olga Luz — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Keane Kevin J — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Kennedy Marianna R — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Morrison William D — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Rouis Jonathan F — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Schiller Jon — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Sousa Gregory — EVP and Deputy CLOGrant/award (A) @ $35.35EDGAR
2026-06-174Lesler Michael — EVP, Chief Financial OfficerGrant/award (A) @ $35.35EDGAR
2026-06-174Rowley Richard B — DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174Gilfeather Michael J — President and CEO, DirectorGrant/award (A) @ $35.35EDGAR
2026-06-174HOLCOMBE GREGORY F — DirectorGrant/award (A) @ $35.35EDGAR
2026-05-064Rowley Richard B — DirectorGrant/award (A) @ $34.10EDGAR
2026-04-024Keane Kevin J — DirectorGrant/award (A) @ $32.32EDGAR
2026-04-024Kennedy Marianna R — DirectorGrant/award (A) @ $32.32EDGAR
2026-04-024Rouis Jonathan F — DirectorGrant/award (A) @ $32.32EDGAR
2026-04-024Schiller Jon — DirectorGrant/award (A) @ $32.32EDGAR
2026-04-024Tirado Olga Luz — DirectorGrant/award (A) @ $32.32EDGAR
2026-04-024Rowley Richard B — DirectorGrant/award (A) @ $32.32EDGAR
2026-04-024HOLCOMBE GREGORY F — DirectorGrant/award (A) @ $32.32EDGAR
2026-03-234Sousa Gregory — EVP and Deputy CLOGrant/award (A): 5,056 @ $0 · Tax withholding (F): 1,307 @ $31.15EDGAR
2026-03-234Dineen David P — SVP, Dir. Wealth ServicesGrant/award (A): 4,333 @ $0 · Tax withholding (F): 790 @ $31.15EDGAR
2026-03-234Rooney Stephen — SVP, Chief Credit OfficerGrant/award (A): 2,812 @ $0 · Tax withholding (F): 841 @ $31.15EDGAR
2026-03-234Lesler Michael — EVP, Chief Financial OfficerGrant/award (A): 5,059 @ $0 · Tax withholding (F): 1,177 @ $31.15EDGAR
2026-03-234Gilfeather Michael J — President and CEO, DirectorGrant/award (A): 16,853 @ $0 · Grant/award (A): 9,438 @ $0 · Tax withholding (F): 6,189 @ $31.15 · Purchase (P): 200 @ $31.25EDGAR

Recent 8-K events — Orange County Bancorp, Inc. /DE/

FiledFormItems reportedSource
2026-08-218-K8.01 — Other Events
9.01 — Financial Statements and Exhibits
EDGAR
2026-07-288-K2.02 — Results of Operations and Financial Condition
9.01 — Financial Statements and Exhibits
EDGAR
2026-05-278-K5.07 — Submission of Matters to a Vote of Security HoldersEDGAR
2026-05-228-K8.01 — Other Events
9.01 — Financial Statements and Exhibits
EDGAR
2026-04-288-K2.02 — Results of Operations and Financial Condition
9.01 — Financial Statements and Exhibits
EDGAR
2026-03-258-K5.02 — Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain OfficersEDGAR
2026-02-208-K8.01 — Other Events
9.01 — Financial Statements and Exhibits
EDGAR
2026-02-048-K2.02 — Results of Operations and Financial Condition
9.01 — Financial Statements and Exhibits
EDGAR
2025-11-248-K8.01 — Other Events
9.01 — Financial Statements and Exhibits
EDGAR
2025-11-108-K7.01 — Regulation FD Disclosure
9.01 — Financial Statements and Exhibits
EDGAR
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