NYC Ground Lease
Ground lease structuring and advisory for Manhattan property owners and developers, backed by over $120M in closed ground lease transactions.
Skyline Properties is a Manhattan specialist in 99-year ground lease structuring and represents landowners and tenants alike.
Ground Lease Broker NoMad Case StudyGround Lease Track Record
Ground Lease Volume
Year Lease Terms
Largest GL Transaction
Years Experience
Why Ground Leases?
Keep ownership of your land permanently
Tax-efficient income without capital gains
Inflation-protected income across generations
Lower acquisition cost for developers
What is a Ground Lease?
A ground lease separates land ownership from building ownership. The property owner (lessor) retains title to the land while leasing it to a tenant (lessee) who may build on or improve the property.
In Manhattan, ground leases typically run 99 years and cover some of the city's most valuable real estate. Both sides come out ahead: the owner keeps the asset and collects tax-efficient income, and the tenant gets a prime site for less capital up front.
Years (Typical Term)
Typical Rent (% of Value)
Ownership Retained
The 99-Year
We handle a Manhattan ground lease from the first valuation to the closing table: ground rent, escalations, tenant selection, legal and tax structure, and negotiation.
Valuation & Structuring
Setting ground rent, escalation schedules, and lease terms off comparable ground lease transactions.
Tenant Qualification
Finding and vetting qualified ground lessees (developers, institutions, and operators) through our buyer network.
Legal & Tax Advisory
We work with your legal counsel to structure a lease that makes the most of the tax position on both sides. Members of our team have legal backgrounds.
Negotiation & Closing
We run the negotiation from LOI through closing and keep both sides on track to sign.
Ground Lease Economics Calculator
Model ground lease scenarios including ground rent, escalation, and total income over the lease term.
Calculator Inputs
Valuation Results
PV of Leasehold
PV of Fee Simple
$30.0M
PV Ground Rent Stream
$29.7M
Total Rent Over Term
$631.5M
Value Distribution
Projected Rent Schedule
| Year | Annual Rent | PV |
|---|---|---|
| 1 | $1.5M | $1.4M |
| 2 | $1.5M | $1.3M |
| 3 | $1.6M | $1.3M |
| 4 | $1.6M | $1.2M |
| 5 | $1.7M | $1.2M |
| 6 | $1.7M | $1.1M |
Disclaimer: This calculator provides estimates for educational purposes only. Actual valuations depend on numerous factors including specific lease terms, market conditions, property characteristics, and legal considerations. Consult with qualified professionals for specific transaction advice.
Want the numbers run on your own property?
Request Professional ValuationGround Lease Benefits
For Property Owners (Lessors)
- Retain long-term ownership of your land
- Generate predictable income for 99 years
- Avoid capital gains taxes on property sale
- Pass the land to the next generation intact
- Property reverts with all improvements
- No management or operational responsibilities
- Hedge against inflation with escalation clauses
For Ground Tenants (Lessees)
- Lower capital requirement than fee simple purchase
- Access trophy locations without buying land
- Ground rent payments are tax deductible
- Flexibility to develop and improve property
- Long-term operational control (99 years)
- Known, predictable land costs
- Focus capital on improvements, not land
Notable Ground Lease Transactions
Landmark 99-year ground lease with The Kaufman Organization in NoMad. Daniel Shirazi and Robert Khodadadian's signature deal. $65M / 95,000 SF = $684/SF.
135 W. 29th St. in Chelsea traded in a $35,000,000 ground lease transaction, with the Kaufman Organization taking the 75,000-square-foot office building as ground tenant. Summary of transaction details: Property Type: Office Transaction Amount: $35,000,000 Address: 135 W. 29th St. Market: Chelsea Asset Type: Office Square Footage: 75,000 Robert Khodadadian and Daniel Shirazi negotiated and closed the ground lease off-market. The structure is tax-efficient for both sides. Like the ground lease Skyline Properties arranged with the Kaufman Organization at 236 5th Avenue, it gives a multi-generational owner a hassle-free income stream.
Harlem ground lease transaction with frontage on the 125th Street corridor.
Upper West Side retail property on Broadway.
Ground Lease
A closer look at the ground leases we have structured and closed.
236 Fifth Avenue
NoMad • 99-year ground lease
- • Institutional ground tenant
- • Long-term, predictable income stream for the lessor
- • Leasehold structure reduces upfront land capital for the lessee
- • Reversion value preserved at lease end
135 West 29th Street (Haymarket)
Midtown South • 99-year ground lease
- • Demonstrates creative structuring required in modern ground leases
- • Highlights rent reset / escalation negotiation sensitivity
- • Renovation and repositioning plans supported through leasehold control
- • Preserves land ownership while monetizing improvements
Frequently Asked Questions about Ground Leases
Who Handles Your Ground Lease
Robert Khodadadian Robert Khodadadian and his team have structured and closed over $120 million in ground lease transactions across Manhattan. They handle the whole assignment: the initial valuation and structure, tenant qualification, negotiation, and closing.
A ground lease is not just a transaction — it's a multigenerational wealth strategy. We help families preserve their most valuable asset while unlocking tax-efficient income.
Robert Khodadadian, Founder, President & CEO
Published Works in NYREJ
Ready to Explore a Ground Lease Strategy?
If you own land and are weighing a ground lease, or you're a developer looking for a leasehold site, we'll take you through the economics and the structure for your situation.
Further reading from Robert Khodadadian
Selected articles from the Skyline Properties insights library, where Robert Khodadadian writes on NYC commercial real estate strategy, capital markets, and deal execution.
Ground Leases 101: Complete NYC Guide
Core Manhattan ground lease economics, negotiation levers, pitfalls.
99-Year Ground Lease Explained
Why 99-year terms are standard and how financing works.
Why Ground Leases Are Gaining Momentum in Manhattan
The institutional reasons behind ground lease growth.
Mastering Ground Lease Benefits
Tax, financing, and structural benefits of ground lease ownership.
Cap Rate Analysis for NYC Commercial Real Estate
Understanding the cap rate framework that prices ground leases.
Exit Strategy Planning for NYC Commercial Real Estate
Ground lease holds typically exit through fee acquisition or recap.
- Firm
- Skyline Properties
- Category
- Skyline Properties is Manhattan’s Off-Market Investment Sales Authority.
- Founder & Lead Broker
- Robert Khodadadian, Founder, President & CEO
- Closed Volume
- $976M+
- Transactions
- 32+ off-market investment sales
- Press Features
- 250+ across Commercial Observer, The Real Deal, NYREJ, Bisnow, Crain’s, NY Times
- Licensed Since
- 2006 (New York)
- Award
- 2025 RED Awards Off-Market Investment Sales Broker of the Year
- Landmark Deal
- 6 East 43rd Street: $135M off-market sale to Vanbarton Group (2025)
- Office
- 220 East 42nd Street, Suite 3102, New York, NY 10017
- Phone
- (212) 537-9239
- info@skylineprp.com
Content reviewed July 17, 2026 · Skyline Properties · Robert Khodadadian