THE PRINCIPAL
Twenty years as a lender, principal and adviser.
Simon Osborne has more than 20 years’ experience across real estate lending, principal investment and borrower advisory. His career includes underwriting and origination roles at Deutsche Bank and Fortwell Capital, principal and asset-management experience, and advisory work through Blackbear Capital and Chiltern Finance. He has also held senior roles in Dubai and Abu Dhabi.
Simon leads every Chiltern mandate personally. His experience across both ownership and credit helps clients anticipate how a credit committee will assess a proposal while ensuring the facility works for the asset and its business plan.
TRACK RECORD
Selected transactions.
Transactions advised on, originated, underwritten or executed across advisory and principal roles.
Debt Advisory
£15m
Prime Central London Residential
Development Facility
Debt Advisory
£57m
South-west PBSA
Forward-funded Acquisition & Construction Facility
Debt Advisory
£20m
North-west Hospitality
Acquisition & Refurb Facility
Principal Lending
£100m
UK Senior Living Portfolio
Revolving Construction Facility
Principal Lending
£30m
London Residential
Phased Construction Facility
Debt Advisory
£19m
Regional Hotel Portfolio
Operating Asset Refinance
YOUR SITUATION
Know your financing position before approaching lenders
International ownership structures, covenant pressure, capex requirements and tight timetables can narrow the field of credible lenders. Chiltern identifies those constraints early and builds the financing process around them.
[01]
Acquiring an asset
Establish likely leverage, pricing and conditions before committing equity or finalising the purchase terms.
[02]
Approaching maturity
Compare the incumbent lender’s position with the wider market while there is still time to preserve choice and negotiating leverage.
[03]
Managing portfolio debt
Plan maturities, covenant headroom, capex requirements and lender concentration across the portfolio, rather than treating each facility as an isolated decision.
HOW WE WORK
Engage Chiltern for the stage you need.
Start with an initial view of the financing position, a detailed portfolio review or full execution. Each engagement has a defined scope and deliverable.
[03]
Financing Execution
Chiltern manages the process from credit presentation and lender selection through term comparison, negotiation, diligence and closing. No lender is approached without your written approval.
[02]
Debt Review
A detailed review under NDA of maturities, valuations, income, covenants, hedging, capex and ownership structure. You receive a clear assessment of refinancing risk, lender concentration and the actions to prioritise.
[01]
Initial Finance View
Send a short brief covering five essentials: the asset, value, net income, debt requirement and timing. Within 48 hours, you receive a concise written view of likely lender appetite, indicative structure and the issues that could change the assessment. No lender is approached.
WHY CHILTERN
Borrower-side advice. Relevant lender coverage.
Commercial Alignment
Chiltern acts for the borrower. The scope and fee basis for each engagement are agreed in writing before work begins. We hold no lender mandates and receive no lender or placement fees. Lender recommendations are based on their fit for the transaction.
Lender Coverage
Chiltern considers UK clearing banks, international banks, debt funds, insurers and specialist lenders. The shortlist is built around the asset, borrower, ownership structure, leverage and timetable, informed by current market discussions rather than a fixed panel.
Where relevant, the comparison can include lenders offering Sharia-compliant finance alongside conventional routes.
THE DEBT MONITOR
What we're seeing in the market.
Periodic notes on pricing, lender appetite and structure across UK and cross-border real estate debt.
CAPITAL FLOWS · Q3 2026
The 2021 Vintage: Why the Next 18 Months Favour Prepared Borrowers
SONIA has moved from roughly 1% to roughly 3.9% since facilities written in 2021–22 were priced. For GCC-connected borrowers, the constraint isn't lender appetite — it's a narrower panel willing to underwrite offshore ownership structures at pace. We set out what that means for anyone refinancing into next year.
MARKET VIEW · Q3 2026
The Refinancing Wall Isn't Where You Think It Is
Most coverage of the UK's maturity wall focuses on volume. The more useful question is concentration — which lenders are carrying the risk, and where their appetite is already thinning. A practitioner's read on where the real pressure sits.
COMMON QUESTIONS
Clarity before commitment.
Practical answers on scope, process, fees and confidentiality.
Chiltern advises international owners and acquirers of UK commercial real estate, together with the investment and asset managers acting for them. This includes private investors, family offices, investment companies and other professionally managed owners.
Typically £10 million to £75 million of debt secured on income-producing UK commercial real estate. Industrial, logistics and operational purpose-built student accommodation are particular areas of focus, but not exclusions.
We start with a confidential discussion about the asset, debt requirement and timing. If Chiltern can add value, we agree the appropriate scope: an Initial Financing View, Portfolio Debt Review or full Financing Execution.
Fees depend on the scope and are agreed in writing before work begins. A Portfolio Debt Review is charged at a fixed fee, which can be credited against the execution fee if a mandate follows. Execution fees are payable on completion. Chiltern receives no lender or placement fees.
No. A lender is approached only after the scope has been agreed and you have given written approval.
Chiltern can enter into an NDA before receiving detailed information about an asset, ownership structure or existing facilities. Information is used to assess your requirement and provide the agreed service. Please see our Privacy Notice for details of how information is stored, shared and retained.
No. Chiltern Finance advises corporate borrowers on real estate debt — arranging finance for companies and other professionally managed entities. This falls outside the scope of FCA regulation, which governs advice to individual consumers, regulated mortgage contracts and consumer credit. Chiltern does not provide regulated investment advice, arrange regulated mortgage contracts, or offer consumer credit.
NEXT STEP
Start with the financing question in front of you.
Tell us about the asset, financing requirement and timing. We will establish whether Chiltern can add value and agree the appropriate next step.
Confidential initial conversation. No lender is contacted without your written approval. Our process ensures complete privacy and strategic alignment from the very first interaction.
