Company: BLNE
Filing Date: 2025-09-26
Form Type: 424B5
Source: 0001493152-25-015799
Chunk: 10

Company: Beeline Holdings, Inc.
Filing Date: 2025-09-26
Form: 424B5
Chunk 10
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| Risk                                  
 factors                               |     | This                                                                                                                                     
 investment involves a high degree of risk. See “Risk Factors” beginning on page S-9 of this prospectus supplement,                       
 our Annual Report on Form 10-K for the year ended December 31, 2024, which is incorporated by reference into this prospectus supplement, 
 and the other reports incorporated by reference into the accompanying prospectus for a discussion of factors you should carefully        
 consider before deciding to invest in our common stock.                                                                                  |
| Nasdaq                                
 symbol                                |     | “BLNE”                                                                                                                                   |

The number of shares common stock to be outstanding immediately after this offering is based on 19,642,103 shares of common stock outstanding as of September 23, 2025 and excludes, as of that date:

| ● | An                                                                                             
 estimated 3,902,481 shares of common stock underlying outstanding convertible preferred stock; |

| ● | 6,159,514                                                                                                         
 shares of common stock issuable upon the exercise of outstanding warrants with a weighted average price of $2.67; |

| ● | 29                                                                                                                           
 shares of common stock issuable upon the exercise of outstanding stock options with a weighted average price of $339.49; and |

| S-8 |

| ● | Up                                                                                                                              
 to 2,583,273 shares of common stock available for issuance pursuant to the Company’s Amended and Restated 2025 Equity Incentive 
 Plan and grants thereunder.                                                                                                     |

The share amounts and prices reflected above and elsewhere in this prospectus supplement give effect to the 1-for-10 reverse stock split which was effected at 12:01 am ET on March 12, 2025. Share amounts and prices do not give effect to (i) an estimated 5,868 warrants with an exercise price of $231.20 per share which we are obligated to issue to former Beeline Financial warrant holders as a result of the Merger, or (ii) potential adjustment to the numbers of conversion and exercise prices and underlying shares pursuant to provisions in the respective securities described herein.

<div align='center'>RISK FACTORS</div>

Any investment in our securities involves a high degree of risk. Investors should carefully consider the risks described below and in documents incorporated by reference herein, including Item 1A – Risk Factors of the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2024 filed with the SEC on