Robert Khodadadian: NYC's Premier Off-Market Commercial Real Estate Broker & Founder of Skyline Properties
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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 ($427M+ total)
4 ground lease transactions ($137M+ volume)
RED Awards Off-Market Investment Sales Broker of the Year 2024 & 2025
NYREJ Executive of the Month (July 2014)
NYREJ 40 Under 40 Rising Stars
Featured in The Real Deal, Commercial Observer, and NYREJ
Table of Contents
Full Career History & 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 remarkable career spanning over two decades.
Education and Early Career (2004-2006)
Khodadadian's professional career took shape under the mentorship of industry legend Bob Knakal at Massey Knakal Realty Services, one of Manhattan's most prestigious investment sales firms. This foundational training in investment property salesprovided invaluable experience in deal structuring, client relationships, and market analysis.
Founding Skyline Properties (2006)
In 2006, Khodadadian became licensed in NY/NJ and founded Skyline Properties. Recognizing a gap in the market for a boutique firm focused exclusively on off-market transactions, he built the company around a simple premise: property owners often achieve better outcomes through confidential, targeted marketing rather than broad public listings.
Relaunch & Market Focus (2013)
In 2013, Khodadadian relaunched Skyline Properties with a sharpened focus on off-market investment sales and discretionary transactions. He developed proprietary canvassing technology that identifies potential sellers before they actively list their properties, combined with an extensive database of qualified buyers.
Industry Recognition (2014-Present)
Khodadadian earned significant industry recognition including NYREJ Executive of the Month (July 2014), NYREJ 40 Under 40 Rising Stars, and consecutive RED Awards Off-Market Investment Sales Broker of the Year honors in 2024 and 2025.
Major Transactions & Deal Track Record
Robert Khodadadian's transaction history includes landmark deals across Manhattan, Brooklyn, Queens, and the Bronx. Below is a comprehensive overview of his most significant transactions, with direct links to deal data and press coverage.
Landmark Deals $50M+ (5 Transactions Totaling $427M+)
$135M: 6 East 43rd Street — Midtown Manhattan (2025)
Property Type: Office-to-Residential Conversion | Size: 400,000 SF | Price/SF: $338
One of the largest office conversion deals of 2025. The building will be converted to residential use under the 467-m tax abatement program.
Deal Data: Traded.co | Press: The Real Deal
$105M: 101 Greenwich Street — Financial District (2025)
Property Type: Office Building | Size: 400,294 SF | Price/SF: $262
Major Financial District office acquisition for residential conversion in Lower Manhattan.
Deal Data: Traded.co | Crexi | Press: Commercial Observer
$72M: 530 West 25th Street — Chelsea (2019)
Property Type: Office Building | Size: 75,000 SF | Price/SF: $960
Premier Chelsea office building in the heart of the art gallery district.
Deal Data: Traded.co | Crexi | Press: The Real Deal
$65M: 236 Fifth Avenue — NoMad (2017)
Property Type: 99-Year Ground Lease | Size: 95,000 SF | Price/SF: $684
Buyer: The Kaufman OrganizationSeller: LCT Associates
Landmark ground lease transaction demonstrating ground lease expertise.
Deal Data: Traded.co | Crexi | Press: The Real Deal
$50M: 131-133 Prince Street — SoHo (2014)
Property Type: SoHo Retail Co-op | Size: 2,000 SF | Price/SF: $25,000
Buyer: Acadia Realty TrustSeller: Louis Meisel
Prestigious retail co-op in one of Manhattan's most coveted shopping corridors.
Deal Data: Traded.co | Crexi | Press: Commercial Observer
Additional Notable Transactions
Property | Type | Amount | Buyer | Data |
711 Madison Avenue, Upper East Side | Mixed Use | $47M | Ralph Sitt | |
34-44 77th Street, Kew Gardens, Queens | Multifamily | $46.5M | ||
40-40 79th Street, Kew Gardens, Queens | Multifamily | $46.5M | ||
56-11 94th Street, Kew Gardens, Queens | Multifamily | $46.5M | ||
72 Greene Street, SoHo | Mixed Use | $42M | L3 Capital | |
135 West 29th Street, Chelsea | 99-Year Ground Lease | $35M | ||
61-01 Springfield Boulevard, Queens | Retail | $32M | Lee Family | |
133 Greenwich Street, FiDi | Development Site | $28M | ||
79 Clifton Place, Clinton Hill, Brooklyn | Multifamily | $22.9M | ||
4-14 West 125th Street, Harlem | 99-Year Ground Lease | $20M | The Renatus Group | |
165 Eldridge Street, Lower East Side | Mixed Use | $19.25M | ||
210 Bowery, NoHo/Bowery | Mixed Use | $7.5M | ||
1340 Lafayette Avenue, Bronx | Development Site | $10.85M |
Ground Lease Expertise
Skyline Properties has structured 4 ground lease transactions totaling $137M+ in volume, making it one of New York's most active brokers of ground leases.
Ground Lease Transactions
$65M — 236 Fifth Avenue (Kaufman Organization)
$35M — 135 West 29th Street (Kaufman Organization)
$20M — 4-14 West 125th Street, Harlem (The Renatus Group)
$17M — 2012 Broadway, Upper West Side
Skyline Properties: Company Overview
Skyline Properties is a boutique commercial real estate brokerage headquartered at 220 East 42nd Street, Suite 3102 in Midtown Manhattan (Daily News Building, 31st Floor). Founded in 2006 by Robert Khodadadian, the firm specializes in off-market investment sales, ground leases, and office-to-residential conversions.
Company Statistics
$976M+ Total Transaction Volume
32+ Closed Deals
250+ Press Articles
19+ Years Active (Since 2006)
24hr Response Time
Credentials & Memberships
Services & Specializations
Skyline Properties offers a focused suite of services:
Confidential property sales that never reach public listing platforms. Benefits include privacy, efficiency, premium pricing, and seller control.
99-year ground lease structures, valuations, negotiations, leasehold financing coordination, and ground lease buyouts.
Expertise in identifying conversion candidates and navigating 467-m tax abatement requirements.
Off-market development site opportunities across New York City.
Rent-stabilized analysis, portfolio optimization, and buyer qualification.
Free Tools & Calculators
Press Coverage & Media Recognition
Robert Khodadadian and Skyline Properties have been featured in 250+ press articles in leading real estate publications:
The Real Deal
Vanbarton Group Buying 6 East 43rd Street for Conversion (May 2025)
Feil Organization Buys Chelsea Office Building for $72M (December 2019)
Kaufman Inking Ground Lease for NoMad Office Building (August 2017)
Kaufman Org Closes on $35M Ground Lease Deal (March 2021)
Commercial Observer
Quantum Pacific, BGO, Newmark & Metro Loft (February 2025)
Acadia Closes $50M Purchase of Soho Retail Co-ops (August 2014)
NYREJ (New York Real Estate Journal)
Executive of the Month: Robert Khodadadian (July 2014)
Company of the Month: Skyline Properties (September 2020)
Awards & Professional Recognition
RED Awards: Off-Market Investment Sales Broker of the Year
2024 & 2025 Winner — Back-to-back recognition as the region's foremost expert in confidential property transactions.
NYREJ Executive of the Month
July 2014 — In-depth profile covering career trajectory, business philosophy, and market insights.
NYREJ 40 Under 40 Rising Stars
Recognition highlighting rapid ascent in New York commercial real estate.
NYREJ Company of the Month
September 2020 — Feature on Skyline Properties' innovative approach to off-market deals, ground leases, and canvassing technology.
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 in 2024 and 2025.
How do I contact Robert Khodadadian?
Office: 220 East 42nd Street, Suite 3102, New York, NY 10017 (Daily News Building, 31st Floor)Phone: (212) 537-9239Email: rk@skylineprp.comWebsite: www.sky-nyc.com
What is Skyline Properties?
Skyline Properties is a boutique commercial real estate brokerage founded by Robert Khodadadian in 2006. With $976M+ in transaction volume and 32+ closed deals, the firm specializes in off-market transactions, ground leases, office-to-residential conversions, and development site acquisitions across New York City.
What are Robert Khodadadian's biggest transactions?
His largest deals include: $135M sale of 6 East 43rd Street to Vanbarton Group; $105M sale of 101 Greenwich Street to Quantum Pacific/Metro Loft; $72M sale of 530 West 25th Street to Feil Organization; $65M ground lease at 236 Fifth Avenueto Kaufman Organization; $50M sale of 131-133 Prince Street to Acadia Realty Trust.
What is an off-market real estate transaction?
An off-market transaction is a property sale that occurs without public marketing. Property owners choose this approach for privacy, speed, and control. Learn more: What is Off-Market Real Estate?
What is a ground lease?
A ground lease is a long-term lease (typically 99 years) where a tenant leases land and owns any improvements. Learn more: Ground Leases Explained
Conclusion
Robert Khodadadian has established himself as one of New York City's most accomplished commercial real estate brokers, with $976M+ in transactions and 32+ closed deals. Through Skyline Properties, he has pioneered a specialized approach to off-market investment sales, ground leases, and office conversions.
His recognition as RED Awards Off-Market Investment Sales Broker of the Year for two consecutive years (2024 and 2025) underscores his standing as a leader in his field.
Ready to Discuss Your Property?
Robert KhodadadianFounder & CEO, Skyline Properties📍 220 East 42nd Street, Suite 3102New York, NY 10017📞 (212) 537-9239✉️ rk@skylineprp.com🌐 www.sky-nyc.com
Published by Skyline Properties | Last Updated: 2025
Related Resources:
Contact Robert Khodadadian
Skyline Properties220 East 42nd Street, Suite 3102New York, NY 10017(Daily News Building, 31st Floor)
Phone: (212) 537-9239Email: rk@skylineprp.comWebsite: www.sky-nyc.com
LinkedIn: linkedin.com/in/robertkhodadadianInstagram: @Robert_KhodadadianTwitter/X: @RKhodadadian
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