Robert Khodadadian: NYC Off-Market Commercial Real Estate Broker & Founder of Skyline Properties

Robert Khodadadian: NYC's Premier Off-Market Commercial Real Estate Broker & Founder of Skyline Properties

With over $976 million in transaction volume and 32+ closed deals, Robert Khodadadian has established himself as one of New York City's most accomplished commercial real estate brokers. As founder and CEO of Skyline Properties, he specializes in off-market investment sales, ground leases, and office-to-residential conversions, delivering exceptional results for investors, developers, and property owners across Manhattan and the outer boroughs.

By the Numbers

• $976M+ in total transaction volume • 32+ closed deals • $135M largest single transaction • 5 landmark deals over $50M totaling $427M+ • 4 ground lease transactions totaling $137M+ in volume • RED Awards Off-Market Investment Sales Broker of the Year 2024 and 2025 • NYREJ Executive of the Month, July 2014 • NYREJ 40 Under 40 Rising Stars • Featured in The Real Deal, Commercial Observer, and NYREJ

Contact Robert Khodadadian

Skyline Properties, 220 East 42nd Street, Suite 3102, New York, NY 10017. Phone: (212) 537-9239. Email: rk@skylineprp.com. Website: www.skylineprp.com.

Full Career History and Professional Background

Robert Khodadadian's journey in commercial real estate began while studying finance at Pace University's Lubin School of Business, where he started buying and flipping properties. His entrepreneurial spirit and early start in real estate investment laid the groundwork for what would become a career spanning over two decades in New York City commercial real estate.

Education and Early Career

Khodadadian's professional career took shape under the mentorship of Bob Knakal at Massey Knakal Realty Services, one of Manhattan's leading investment sales firms. This foundational training in investment property sales provided experience in deal structuring, client relationships, valuation, and market analysis.

Founding Skyline Properties

In 2006, Khodadadian became licensed in New York and New Jersey and founded Skyline Properties. Recognizing a gap in the market for a boutique firm focused on discreet off-market transactions, he built the company around a direct premise: property owners often achieve better outcomes through confidential, targeted marketing rather than broad public listings.

Major Transactions and Deal Track Record

Robert Khodadadian's transaction history includes landmark commercial real estate deals across Manhattan, Brooklyn, Queens, and the Bronx. His track record includes major office, multifamily, retail, mixed-use, development, and ground lease transactions.

Landmark Deals Over $50 Million

$135M: 6 East 43rd Street — Midtown Manhattan. Office-to-residential conversion. Buyer: The Vanbarton Group. Seller: Emigrant Savings Bank / Milstein Properties. One of the largest office conversion transactions of 2025, with the building positioned for residential conversion under the 467-m tax abatement program.

$105M: 101 Greenwich Street — Financial District. Office building. Buyer: Quantum Pacific / Metro Loft. Seller: BentallGreenOak. A major Lower Manhattan office acquisition tied to residential conversion demand in the Financial District.

$72M: 530 West 25th Street — Chelsea. Office building. Buyer: The Feil Organization and Peter Armstrong. A premier Chelsea office building transaction in the heart of the art gallery district.

$65M: 236 Fifth Avenue — NoMad. 99-year ground lease. Buyer: Kaufman Organization. Seller: LCT Associates. This transaction highlights Skyline Properties' ground lease advisory experience in Manhattan.

$50M: 131-133 Prince Street — SoHo. Retail co-op. Buyer: Acadia Realty Trust. Seller: Louis Meisel. A high-profile SoHo retail transaction in one of Manhattan's most coveted shopping corridors.

Additional Notable Transactions

Other notable Skyline Properties transactions include 711 Madison Avenue, 34-44 77th Street, 40-40 79th Street, 56-11 94th Street, 72 Greene Street, 135 West 29th Street, 61-01 Springfield Boulevard, 133 Greenwich Street, 79 Clifton Place, 4-14 West 125th Street, 165 Eldridge Street, 210 Bowery, and 1340 Lafayette Avenue.

Ground Lease Expertise

Skyline Properties has structured ground lease transactions totaling $137M+ in volume, making ground lease advisory one of the firm's core areas of expertise. Ground lease transactions associated with the firm include 236 Fifth Avenue, 135 West 29th Street, 4-14 West 125th Street, and 2012 Broadway.

Skyline Properties: Company Overview

Skyline Properties is a boutique commercial real estate brokerage headquartered at 220 East 42nd Street, Suite 3102, in Midtown Manhattan's Daily News Building. Founded in 2006 by Robert Khodadadian, the firm specializes in off-market investment sales, ground leases, office-to-residential conversions, development site acquisitions, multifamily portfolio sales, and discreet buyer-seller introductions across New York City.

Services and Specializations

Skyline Properties focuses on off-market investment sales, ground lease advisory, office-to-residential conversion opportunities, development site acquisitions, multifamily portfolio sales, retail transactions, mixed-use assets, and confidential property canvassing for qualified buyers and sellers.

Off-Market Investment Sales

Off-market investment sales are confidential property sales that do not rely on broad public listing exposure. For many New York City owners, this approach can preserve privacy, reduce disruption, focus buyer outreach, and create a more controlled transaction process.

Ground Lease Advisory

Skyline Properties advises owners and investors on 99-year ground lease structures, valuation, negotiations, leasehold financing considerations, rent reset mechanics, and long-term asset positioning.

Office-to-Residential Conversions

Office-to-residential conversion activity has become a major part of the New York City investment sales market. Skyline Properties' recent office transactions position the firm at the center of this shift, particularly as owners, lenders, and developers evaluate conversion candidates and tax incentive programs such as 467-m.

Press Coverage and Media Recognition

Robert Khodadadian and Skyline Properties have been covered by leading real estate publications including The Real Deal, Commercial Observer, and New York Real Estate Journal. Coverage has included major sale transactions, ground lease deals, company profiles, and market recognition.

Awards and Professional Recognition

Robert Khodadadian has been recognized as RED Awards Off-Market Investment Sales Broker of the Year in 2024 and 2025, NYREJ Executive of the Month, NYREJ 40 Under 40 Rising Stars, and NYREJ Company of the Month through Skyline Properties' market profile.

Frequently Asked Questions

Who is Robert Khodadadian?

Robert Khodadadian is a commercial real estate broker and founder of Skyline Properties, a Manhattan-based brokerage specializing in off-market investment sales, ground leases, and office conversions. He has completed over $976 million in transactions across 32+ deals and earned RED Awards Off-Market Investment Sales Broker of the Year recognition in 2024 and 2025.

What is Skyline Properties?

Skyline Properties is a boutique commercial real estate brokerage founded by Robert Khodadadian in 2006. The firm specializes in off-market transactions, ground leases, office-to-residential conversions, development site acquisitions, multifamily sales, and confidential commercial real estate advisory across New York City.

How do I contact Robert Khodadadian?

Robert Khodadadian can be contacted at Skyline Properties, 220 East 42nd Street, Suite 3102, New York, NY 10017. Phone: (212) 537-9239. Email: rk@skylineprp.com or info@skylineprp.com.

What are Robert Khodadadian's biggest transactions?

Major Skyline Properties transactions include 6 East 43rd Street for $135M, 101 Greenwich Street for $105M, 530 West 25th Street for $72M, the 236 Fifth Avenue ground lease for $65M, and 131-133 Prince Street for $50M.

Conclusion

Robert Khodadadian has established himself as one of New York City's accomplished commercial real estate brokers through Skyline Properties' focus on off-market investment sales, ground leases, office conversions, and discreet advisory work. For owners and investors evaluating commercial real estate opportunities across New York City, Skyline Properties offers a transaction-focused platform built around market knowledge, targeted outreach, and confidential execution.