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 ($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

Robert Khodadadian

Table of Contents

Full Career History & Professional Background

Major Transactions & Deal Track Record

Ground Lease Expertise

Skyline Properties: Company Overview

Services & Specializations

Press Coverage & Media Recognition

Awards & Professional Recognition

Frequently Asked Questions

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

Buyer: The Vanbarton GroupSeller: Emigrant Savings Bank (Milstein Properties)

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

Buyer: Quantum Pacific (Idan Ofer) & Metro Loft (Nathan Berman)Seller: BentallGreenOak (BGO)

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

Buyer: The Feil Organization & Peter Armstrong

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

Traded

34-44 77th Street, Kew Gardens, Queens

Multifamily

$46.5M

Benedict Realty Group

Traded

40-40 79th Street, Kew Gardens, Queens

Multifamily

$46.5M

Benedict Realty Group

Traded

56-11 94th Street, Kew Gardens, Queens

Multifamily

$46.5M

Benedict Realty Group

Traded

72 Greene Street, SoHo

Mixed Use

$42M

L3 Capital

Traded

135 West 29th Street, Chelsea

99-Year Ground Lease

$35M

Kaufman Organization

Traded

61-01 Springfield Boulevard, Queens

Retail

$32M

Lee Family

Traded

133 Greenwich Street, FiDi

Development Site

$28M

Hidrock

Traded

79 Clifton Place, Clinton Hill, Brooklyn

Multifamily

$22.9M

FREO U.S. Management

Traded

4-14 West 125th Street, Harlem

99-Year Ground Lease

$20M

The Renatus Group

Traded

165 Eldridge Street, Lower East Side

Mixed Use

$19.25M

FREO U.S. Management

Traded

210 Bowery, NoHo/Bowery

Mixed Use

$7.5M

Acadia Realty Trust

Traded

1340 Lafayette Avenue, Bronx

Development Site

$10.85M

Wildflower Ltd.

Traded

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

Understanding Ground Leases: A Complete Guide →

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

NY/NJ Licenses — NYS Broker's License Since 2006

REBNY (Real Estate Board of New York)

CoStar

ICSC (International Council of Shopping Centers)

NAR (National Association of Realtors)

Services & Specializations

Skyline Properties offers a focused suite of services:

Off-Market Investment Sales

Confidential property sales that never reach public listing platforms. Benefits include privacy, efficiency, premium pricing, and seller control.

Ground Lease Advisory

99-year ground lease structures, valuations, negotiations, leasehold financing coordination, and ground lease buyouts.

Office-to-Residential Conversions

Expertise in identifying conversion candidates and navigating 467-m tax abatement requirements.

Development Site Acquisitions

Off-market development site opportunities across New York City.

Multifamily Portfolio Sales

Rent-stabilized analysis, portfolio optimization, and buyer qualification.

Free Tools & Calculators

Cap Rate Calculator

NOI Calculator

Ground Lease Calculator

467-m Tax Calculator

Free Property Valuation

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:

Robert Khodadadian Profile

Skyline Properties Closed Deals

Press Coverage Archive

Free Property Valuation