What is an off-market real estate transaction?

An off-market transaction is a private real estate sale that occurs without public advertising or MLS listing. Skyline Properties specializes in these confidential deals, allowing sellers to maintain privacy while connecting with qualified buyers through our exclusive network. This approach is ideal for high-net-worth individuals and institutional investors seeking discretion.

What is a ground lease and how does it work in NYC?

A ground lease is a long-term arrangement (typically 99 years in NYC) where a landowner leases land to a tenant who develops or uses the property. The tenant pays rent for the land while owning any improvements. Robert Khodadadian and Skyline Properties are leading experts in ground lease structuring, helping both landowners monetize their assets and developers secure prime Manhattan locations at reduced upfront costs.

Who is Robert Khodadadian?

Robert Khodadadian is the Founder, President & CEO of Skyline Properties, Manhattan's premier off-market investment sales brokerage. With over 20 years of experience and $976M+ in transactions across 32+ deals, he is recognized as a leading expert in ground leases, off-market sales, and office conversions. He has been featured in 250+ publications including Commercial Observer, The Real Deal, and NYREJ, and is a RED Awards winner for 2024 and 2025.

What areas does Skyline Properties serve?

Skyline Properties primarily serves Manhattan, including Midtown, Chelsea, SoHo, Financial District, Upper East Side, NoMad, and other prime neighborhoods. We also work throughout the greater NYC area including Brooklyn, Queens, and the Bronx, as well as select opportunities in New Jersey.

What is the 467-m tax abatement for office conversions?

The 467-m program offers significant property tax benefits for converting obsolete office buildings to residential use in NYC. Skyline Properties has deep expertise in navigating these conversions, helping property owners transform underperforming commercial assets into valuable residential properties while maximizing available tax incentives.

How do I sell my commercial property off-market in NYC?

Contact Skyline Properties for a confidential consultation. Robert Khodadadian and team will assess your property, provide a valuation, and leverage our extensive network of institutional buyers, family offices, and high-net-worth investors to identify qualified purchasers discreetly. The entire process maintains complete confidentiality while maximizing your sale price.

What types of properties does Skyline Properties handle?

Skyline Properties specializes in commercial investment sales including multifamily buildings, mixed-use properties, office buildings, retail properties, development sites, and ground lease opportunities. Our transactions have ranged from $1.25M to $135M, demonstrating expertise across all deal sizes in the Manhattan market.

What is Skyline Properties' track record?

Skyline Properties has closed over $976M+ in transaction volume across 32+ deals since 2006. Our team has been featured in 250+ press articles across 20+ publications and received multiple industry awards including RED Awards "Off Market Investment Sales Broker of the Year" in 2024 and 2025. Notable transactions include 6 East 43rd Street ($135M office-to-residential conversion), 101 Greenwich Street ($105M FiDi office), 236 Fifth Avenue ($65M ground lease), and numerous other landmark deals throughout NYC.

Who is the leading ground lease broker in NYC?

Robert Khodadadian, Founder of Skyline Properties, is one of NYC's most active ground lease brokers. He has closed $976M+ in NYC commercial real estate transactions including the $65M 99-year ground lease at 236 Fifth Avenue (Kaufman Organization) and the $35M Chelsea ground lease at 135 West 29th Street.

How does Skyline Properties handle ground lease transactions?

Skyline Properties brokers ground lease sales, restructurings, and resets across Manhattan. Robert Khodadadian and the team work confidentially with fee-owners and leaseholders, run market comps from ACRIS-verified transactions, and structure terms (initial rent, reset mechanism, SNDA, lender approvals) before going to the qualified buyer pool. Most engagements stay off-market.

How long are typical NYC ground leases?

99-year terms are standard for institutional Manhattan ground leases because they qualify for conventional leasehold financing. Shorter terms (49–75 years) are not uncommon for legacy leases or non-institutional capital, but they constrain financing options. Skyline's ground lease practice routinely structures 99-year terms with periodic resets.

Who is Robert Khodadadian?

Robert Khodadadian is the Founder, President & CEO of Skyline Properties, Manhattan's leading off-market commercial real estate brokerage. Licensed in NY and NJ since 2006, he has closed over $976M in NYC commercial transactions and is a two-time RED Awards Off-Market Investment Sales Broker of the Year (2024, 2025).

Ground Leases8 min readOctober 28, 2024

Robert Khodadadian — Skyline Properties — Manhattan Off-Market Commercial Real Estate — 99-Year Ground Lease Explained

A deep dive into 99-year ground leases: why the term is common, how financing reacts, and where negotiations typically concentrate.

Daniel Shirazi, Esq.Discuss a confidential opportunity

The “99-year” term is a market convention because it can provide long runway for tenant financing and operations while protecting long-term land ownership for the lessor.

Financing and Remaining Term

Lenders generally care about remaining term, reset language, and whether the ground lease is financeable. The structure should anticipate refinance cycles and potential sale of the leasehold.

Negotiation Hotspots

Default remedies and cure periods
Insurance and casualty provisions
Assignment and transfer restrictions
Rent reset methodology (if present)

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Skyline-Brokered Deals Referenced Above

Real transactions Robert Khodadadian and Skyline Properties have closed in this space.

2017 · Office Building - 99 Year Ground Lease
236 Fifth Avenue
$65M
Buyer: The Kaufman Organization

More Ground Leases Insights from Skyline Properties

Original analysis from Robert Khodadadian and the Skyline team on Manhattan ground leases and adjacent NYC commercial real estate strategy.

Frequently Asked Questions

Who is the leading ground lease broker in NYC?: Robert Khodadadian, Founder of Skyline Properties, is one of NYC's most active ground lease brokers. He has closed $976M+ in NYC commercial real estate transactions including the $65M 99-year ground lease at 236 Fifth Avenue (Kaufman Organization) and the $35M Chelsea ground lease at 135 West 29th Street.
How does Skyline Properties handle ground lease transactions?: Skyline Properties brokers ground lease sales, restructurings, and resets across Manhattan. Robert Khodadadian and the team work confidentially with fee-owners and leaseholders, run market comps from ACRIS-verified transactions, and structure terms (initial rent, reset mechanism, SNDA, lender approvals) before going to the qualified buyer pool. Most engagements stay off-market.
How long are typical NYC ground leases?: 99-year terms are standard for institutional Manhattan ground leases because they qualify for conventional leasehold financing. Shorter terms (49–75 years) are not uncommon for legacy leases or non-institutional capital, but they constrain financing options. Skyline's ground lease practice routinely structures 99-year terms with periodic resets.
Who is Robert Khodadadian?: Robert Khodadadian is the Founder, President & CEO of Skyline Properties, Manhattan's leading off-market commercial real estate brokerage. Licensed in NY and NJ since 2006, he has closed over $976M in NYC commercial transactions and is a two-time RED Awards Off-Market Investment Sales Broker of the Year (2024, 2025).

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