
Ground Lease
Skyline Properties is one of NYC's leading ground lease brokerages. Robert Khodadadian structures, values, and closes 99-year ground leases, fee position sales, and leasehold transactions across Manhattan and the boroughs. Skyline closed 236 Fifth Avenue ($65M ground lease) and continues to source off-market ground lease opportunities.
What is a Ground Lease in NYC?
A ground lease in NYC is a long-term lease — typically 99 years — under which a tenant pays the landowner ground rent and develops or operates a building on the land. The landowner retains the fee (the underlying ownership of the land), and the tenant owns the improvements for the duration of the lease.
In Manhattan, the most valuable ground leases sit under trophy office, hotel, multifamily, and mixed-use buildings. The fee position is typically held by long-time, often multi-generational ownership, and the leasehold position is often held by institutional capital. Skyline Properties has structured and brokered ground leases across both sides of the table.
Ground Lease NYC — Skyline Coverage
Skyline acts on every ground lease structure that trades in the New York market.
- Fee position sales (selling the land under an existing leasehold)
- 99-year ground lease structuring (creating a new ground lease over fee land)
- Leasehold position sales (selling the tenant's interest)
- Ground rent reset and ground rent restructuring advisory
- Ground lease for development (ground-up under a long-term lease)
- Ground lease valuation and broker opinions of value
- Ground lease 1031 exchange placement
Why Owners Sell Ground Lease Positions in NYC
Selling a NYC ground lease position is a strategic decision. Long-time owners often hold ground lease positions as multi-generational legacy assets, but rising estate planning needs, capital reallocation, and 1031 exchange opportunities frequently make a fee position sale the right move.
Skyline runs every fee position sale confidentially — protecting the relationship with the leasehold tenant and preserving the integrity of the ground rent stream during marketing.
- Estate planning and generational wealth transfer
- Capital reallocation into higher-yielding investments
- 1031 exchange placement into income-producing assets
- Liquidity from a non-cash-flow-rich legacy asset
- Confidential, off-market execution to protect leasehold relationships
Ground Lease Structuring for NYC Developers
On the development side, a ground lease can unlock projects that fee-simple acquisition cannot. By keeping land out of the capital stack, ground lease structures lower the equity check, improve project IRR, and allow legacy landowners to participate in long-term upside without selling outright.
Skyline structures ground leases for ground-up development, conversion, and recapitalization — and represents both fee owners and developer-tenants.
- Net effective ground rent and step-up modeling
- 99-year vs 49-year vs 75-year structure tradeoffs
- CPI escalations and fair-market reset clauses
- Subordination, non-disturbance, and SNDA structuring
- Fee owner participation (kicker structures, profit participation)
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Frequently Asked
A NYC ground lease is a long-term lease — typically 99 years — under which a tenant pays ground rent to the landowner and develops or operates a building on the land. The landowner keeps the fee (the underlying land), and the tenant owns the improvements for the duration of the lease.
A NYC ground lease is valued by capitalizing the ground rent stream against current ground lease cap rates, then adjusting for term remaining, escalation structure, fair-market reset clauses, and the credit quality of the leasehold tenant. Skyline provides confidential ground lease broker opinions of value for both fee and leasehold positions.
NYC ground lease fee positions are typically purchased by family offices, REITs, insurance companies, and pension funds looking for low-volatility, inflation-protected income. Skyline maintains active ground lease buyer mandates from many of these capital sources.
Yes. Skyline regularly structures new 99-year ground leases for NYC owners who want to monetize the value of their land without selling it. Structuring involves negotiating ground rent, escalation clauses, reset language, term, subordination, and fair-market rent provisions — all of which directly affect both sides' economics.
Skyline handles ground lease transactions confidentially. Robert Khodadadian leads every ground lease assignment personally, runs the valuation and structuring work in-house, and matches the position with the right capital — typically off-market.
Structuring or selling a NYC ground lease?
Skyline runs ground lease transactions confidentially. Direct line to Robert Khodadadian.
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