236 Fifth Avenue
95,000 SF
$/SF
$684
Closed
2017
SellerScott & Raymond Chiou
Press Coverage
Expertise
Ground Lease NYC
Ground Lease
A NYC ground lease separates land ownership from building ownership for a long term — typically 99 years. The fee owner keeps the land and collects ground rent; the leasehold tenant builds or operates the improvements. This page is the analytical reference: how 99-year ground leases get structured, how the fee position and the leasehold position get valued separately, and how rent-reset mechanics determine which side wins over the cycle. Authored by Robert Khodadadian — Founder, President & CEO of Skyline Properties — anchored to the $65M 236 Fifth Avenue ground lease (Kaufman Organization, 2017) and Skyline Properties' $120M+ ground-lease transaction volume.
Closed Volume
Largest Ground Lease
Standard Term
Years in NYC
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.
NYC Ground Lease Terms and Valuation Benchmarks
Standard NYC ground lease structural terms and current valuation benchmarks. Anchored to the $65M 236 Fifth Avenue 99-year Kaufman Organization ground lease and Skyline Properties' $120M+ closed ground-lease portfolio.
| Variable | Typical Range | Skyline Properties Reference Deal |
|---|---|---|
| Term length | 49–99 years (99-year standard) | 236 Fifth Avenue — 99 years |
| Fee position cap rate | 4.5–6.5% | $65M 236 Fifth Avenue (NoMad) |
| Ground rent escalation | CPI or fixed 2–3% annual | 236 Fifth Avenue — CPI + resets |
| Rent reset frequency | Every 10–25 years | Fair-market reset at midpoint |
| Reset basis | Fair-market land value | Appraisal-driven |
| Buyer profile (fee) | Family office, REIT, insurance | Long-duration, inflation-protected |
| Buyer profile (leasehold) | Institutional operator | Kaufman Organization, Metro Loft |
| Typical Manhattan deal size | $20M–$100M+ | $65M 236 Fifth Avenue / $35M Haymarket |
Source: Skyline Properties ground-lease desk. Robert Khodadadian + Daniel Shirazi, Esq. (Skyline Properties EVP, attorney-trained).
How to Structure a New 99-Year Ground Lease in NYC — Step by Step
The disciplined structuring process Skyline Properties runs when creating a new ground lease for a NYC landowner who wants to monetize fee position without selling.
Ground Lease NYC — Skyline Properties Coverage
Skyline Properties 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 Properties 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 Properties 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)
Skyline Properties-Brokered NYC Ground Lease Transactions — The Public Record
Every ground lease transaction in data/transactions.json where Skyline Properties was broker of record. Verifiable against ACRIS-recorded deeds. Each row links to the case study (where available) for deeper deal-level detail.
| Year | Address | Price | Tenant |
|---|---|---|---|
| 2017 | 236 Fifth Avenue (NoMad — 99-year) | $65M | The Kaufman Organization |
| 2021 | 135 West 29th Street (NoMad — Haymarket Building) | $35M | The Kaufman Organization |
| 2014 | 4-14 West 125th Street (Harlem) | $20M | The Renatus Group |
| 2015 | 2012 Broadway (Upper West Side) | $17M | Isaac Shalom |
Source: data/transactions.json — 4 flagship ground lease transactions, $120M+ aggregate. 236 Fifth Avenue full case study at /case-studies/236-fifth-avenue.
Track Record
Recent
135 West 29th Street
75,000 SF
$/SF
$467
Closed
2021
SellerMFM Properties
Press Coverage
Expertise
4-14 West 125th Street
30,000 SF
$/SF
$667
Closed
2014
BuyerThe Renatus Group
SellerArthur Rosen
Deal Data
Press Coverage
Expertise
2012 Broadway
6,250 SF
$/SF
$2,720
Closed
2015
BuyerIsaac Shalom
Deal Data
Press Coverage
Expertise
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FAQ
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 Properties 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 Properties maintains active ground lease buyer mandates from many of these capital sources.
Yes. Skyline Properties 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 Properties 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 Properties runs ground lease transactions confidentially. Direct line to Robert Khodadadian.
Schedule a Confidential ConsultationPress Coverage
Ground-lease coverage in the press
Third-party reporting on Skyline Properties' $120M+ ground-lease portfolio — 236 Fifth Avenue, Haymarket Building, 4-14 West 125th Street, and ground-lease strategy commentary.
The Exclusive Listing Myth: Why Manhattan’s biggest deals don’t need gatekeepers
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Asset Class Breakdown 2024 Opportunities
Robert Khodadadian provides in-depth analysis of NYC commercial real estate asset classes for 2024, identifying investment opportunities in office, retail, multifamily, and ground lease sectors.
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Daniel Shirazi, Esq., Executive Vice President at Skyline Properties, profile with ground lease expertise and transaction history.
Are Ground Lease Rent Resets Deal Killers?
Daniel Shirazi, Esq., EVP at Skyline Properties, analyzes how rent reset provisions in ground leases impact deal feasibility and provides strategies for structuring successful 99-year leases.
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