Robert
Founder, President & CEO of Skyline Properties. Focused on Manhattan off-market investment sales, ground leases, and complex NYC transactions.
Overview
Robert Khodadadian founded Skyline Properties in 2006 and relaunched the firm in 2013 after training at Massey Knakal Realty Services under the mentorship of Bob Knakal. With $976M+ in closed NYC commercial real estate transactions, he is known for discreet, relationship-driven sourcing and structuring across off-market investment sales, ground leases, multifamily portfolios, development sites, and office-to-residential conversion advisory. His career began while studying finance at Pace University's Lubin School of Business, where he started buying and flipping properties.
Credentials
Awards & Recognition
Media & Publications
Featured in leading real estate industry publications:
Expertise
Where he spends his time in NYC commercial real estate:
Career
Early Career
Started out in real estate and finance, then narrowed his focus to NYC commercial investment sales.
Licensed & Founded Skyline Properties
Became licensed in New York (since 2006) and founded Skyline Properties.
Relaunch & Market Focus
Relaunched the firm focused squarely on off-market investment sales and confidential transactions.
Recognition (NYREJ)
Named NYREJ Executive of the Month (July 2014), along with other industry recognition.
Landmark: 131–133 Prince Street ($50M)
Record SoHo retail co-op sale, covered widely in the industry press.
Ground Lease Landmark: 236 Fifth Avenue ($65M)
A 99-year ground lease on Fifth Avenue in NoMad, and the core of Skyline's ground lease practice.
Chelsea Office: 530 West 25th Street ($72M)
Major Chelsea office sale in the gallery district.
$50M+ Landmark Deals
Major NYC office and conversion transactions, including 101 Greenwich Street ($105M+) and 6 East 43rd Street ($135M).
Today
Advising clients on off-market investment sales, ground leases, and office-to-residential conversions in NYC.
About Robert Khodadadian: Inside the Practice
Robert Khodadadian is the Founder, President & CEO of Skyline Properties, Manhattan’s Off-Market Investment Sales Authority. Licensed in New York since 2006, he has closed $976M+ across 32+ NYC transactions and is the 2025 RED Awards Off-Market Investment Sales Broker of the Year.
Robert Khodadadian is the Founder, President & CEO of Skyline Properties, a New York City commercial real estate brokerage specializing in off-market investment sales, ground leases, and office-to-residential conversions. Licensed in New York since 2006, Robert founded Skyline Properties that same year and relaunched the firm in 2013 with a sharpened off-market focus after training under Bob Knakal at Massey Knakal Realty Services. He has closed $976M+ across 32+ Manhattan transactions, including the $135M Vanbarton 6 East 43rd Street office-to-residential conversion (2025), the $105M Quantum Pacific + Metro Loft acquisition of 101 Greenwich Street (2025), the $72M Feil/Rigby Chelsea office (2019), the $65M Kaufman ground lease at 236 Fifth Avenue (2017), and the record $50M Acadia Realty Trust acquisition of 131-133 Prince Street (2014). He is the 2025 RED Awards Off-Market Investment Sales Broker of the Year, a Pace University Lubin School of Business alumnus, and a member of REBNY and NAR.
Robert Khodadadian is the Founder, President & CEO of Skyline Properties, a New York City commercial real estate brokerage specializing in off-market investment sales, ground leases, and office-to-residential conversions. Over two decades in the Manhattan investment-sales market, Robert has closed more than $976M in commercial real estate transactions across office, multifamily, retail, ground lease, and development-site asset classes, most of it brokered confidentially without ever reaching the public market.
Licensed in New York since 2006, Robert founded Skyline Properties the same year and relaunched the firm in 2013 with a sharpened focus on off-market execution. His early bet was that the best NYC commercial real estate sellers and buyers wanted a disciplined, confidential process instead of broad public exposure. A decade of consistent closings has borne that out: the $135M Vanbarton Group acquisition of 6 East 43rd Street (one of NYC’s largest 467-m office-to-residential conversions, 441 units with a $300M Brookfield construction loan), the $105M Quantum Pacific + Metro Loft acquisition of 101 Greenwich Street (the largest confidential FiDi office trade of 2025), the $72M Feil Organization + Rigby Asset Management acquisition of 530 West 25th Street in Chelsea, the $65M Kaufman Organization ground lease at 236 Fifth Avenue in NoMad, and the record $50M Acadia Realty Trust acquisition of 131-133 Prince Street in the SoHo Cast-Iron Historic District ($16,667/SF, still a benchmark SoHo retail co-op comp).
Robert was named the 2025 RED Awards Off-Market Investment Sales Broker of the Year by Connect Media / Connect CRE, recognition that puts him in a narrow group of NYC commercial brokers who have built repeatable off-market practices instead of relying on one-off relationships. He has been featured in 250+ press articles across Commercial Observer, The Real Deal, Crain’s New York Business, Bisnow, the New York Times, New York Post, Multi-Housing News, and the New York Real Estate Journal, including NYREJ Executive of the Month (July 2014), NYREJ 40 Under 40 Rising Stars, NYREJ Company of the Month (Skyline Properties), and the NYREJ 35th Anniversary featured profile.
Robert holds memberships in the Real Estate Board of New York (REBNY) and the National Association of Realtors (NAR). He is an alumnus of Pace University’s Lubin School of Business. Robert personally leads every Skyline Properties assignment. There is no junior hand-off, no marketing-team intermediary, and no public exposure unless the seller asks for it. Direct line: (212) 537-9239 · info@skylineprp.com.
“Twenty years in Manhattan commercial real estate taught me one thing: the deals worth doing are the ones the public market never sees. Confidentiality, single-point-of-contact execution, and a curated buyer pool — that’s the discipline.”
A note on representation
Why senior-led execution matters at the $50M+ tier
Most Manhattan brokerages run a partner-on-pitch, associate-on-execution model. The principal pitches the listing in a polished deck, an analyst builds the OM, junior brokers handle the tour calls. By the time you’re at LOI, the person who promised you discretion isn’t in the room. The conversation about price-and-terms moves to someone who wasn’t at the kitchen table.
Skyline Properties is structured differently because Robert leads every assignment personally. The first phone call, the comp work, building the buyer pool, the LOI negotiation, the closing: one person handles every step. There’s no telephone game between you and the counterparty. For a $50M+ NYC commercial transaction, that single-point-of-contact accountability is the difference between a clean close and a re-trade six weeks before the wire goes out.
The track record ($976M+ across 32+ documented closings, including $135M Vanbarton, $105M Quantum Pacific, $72M Feil/Rigby, the $65M Kaufman ground lease, and the $50M Acadia record) is what that discipline produces.
Practice Areas: Where Robert Brokers
Robert Khodadadian and Skyline Properties cover every major commercial asset class in Manhattan and Brooklyn. These are the practice areas where Robert has the deepest closed-deal record.
Off-Market Investment Sales
Confidential commercial real estate transactions closed without public marketing. Skyline Properties’ pre-qualified network of institutional investors, family offices, REITs, and private equity, together with 20+ years of relationships with multi-generational Manhattan owners, makes Robert one of NYC’s most consistent off-market dealmakers. Off-market practice details →
99-Year Ground Leases
Manhattan ground-lease specialist on both fee and leasehold positions. Notable: $65M Kaufman Organization ground lease at 236 Fifth Avenue (NoMad), $35M Kaufman Organization ground lease at the Haymarket Building (135 West 29th Street). Robert co-authored several NYREJ pieces on ground-lease structure, rent resets, and subordination. Ground lease practice →
Office-to-Residential Conversions (467-m)
Conversion specialist on NY State RPTL §467-m candidate sourcing and execution. Brokered the $135M Vanbarton 6 East 43rd Street conversion (441 units, 111 affordable) and the $105M Quantum Pacific + Metro Loft 101 Greenwich Street conversion. The June 30, 2031 commencement deadline shapes every 467-m advisory engagement. Conversion practice →
Multifamily Portfolio Sales
Manhattan and Brooklyn multifamily: free-market apartment buildings, rent-stabilized portfolios, pre-war elevator stock, walk-ups, and mixed-use multifamily. Post-HSTPA pricing discipline on rent-stabilized assets is a Skyline Properties specialty. Active acquisition mandates across Upper East Side, Upper West Side, Lower East Side, Williamsburg, and beyond. Multifamily practice →
Development Sites & Air Rights
NYC development site brokerage: as-of-right sites, air rights, multi-lot assemblages, TDR transactions. Submarket coverage from Chelsea’s High Line corridor through Brooklyn’s Williamsburg/Bushwick/Bed-Stuy growth markets. Underwriting framework grounded in real comparable land sales, current construction costs, and projected stabilized exit cap rates. Development site practice →
Retail & Mixed-Use
Manhattan retail specialty includes the record $50M Acadia Realty Trust acquisition of 131-133 Prince Street ($16,667/SF SoHo retail co-op benchmark) and the $20M Acadia acquisition of 210 Bowery. SoHo, NoLita, NoMad, Flatiron, and Madison Avenue corridor coverage; mixed-use retail-over-residential active across every Manhattan submarket. SoHo commercial real estate →
Notable Closed Transactions: Robert’s Manhattan Track Record
Six landmark closings that anchor Robert Khodadadian’s $976M+ Manhattan track record. Each links to the full deal page with buyer, seller, capital structure, and press coverage.
Frequently Asked Questions About Robert Khodadadian
Who is Robert Khodadadian?
Robert Khodadadian is the Founder, President & CEO of Skyline Properties, a New York City commercial real estate brokerage specializing in off-market investment sales, ground leases, and office-to-residential conversions. He has closed $976M+ in NYC commercial real estate transactions and is the 2025 RED Awards Off-Market Investment Sales Broker of the Year.
How long has Robert Khodadadian been in NYC commercial real estate?
Robert has been licensed in New York since 2006, which puts him 20+ years into the Manhattan commercial real estate market. He founded Skyline Properties in 2006 and relaunched the firm with an off-market focus in 2013.
What deals has Robert Khodadadian brokered?
Robert’s landmark closings include the $135M Vanbarton 6 East 43rd Street office-to-residential conversion, the $105M Quantum Pacific + Metro Loft 101 Greenwich Street acquisition, the $72M Feil Organization 530 West 25th Street Chelsea office sale, the $65M Kaufman Organization ground lease at 236 Fifth Avenue, and the $50M Acadia Realty Trust acquisition of 131-133 Prince Street ($16,667/SF SoHo retail record). Total closed volume is $976M+ across 32+ transactions.
What awards has Robert Khodadadian won?
Robert is the 2025 RED Awards Off-Market Investment Sales Broker of the Year, NYREJ Executive of the Month (July 2014), NYREJ 40 Under 40 Rising Stars, NYREJ Company of the Month (Skyline Properties), and was featured in the NYREJ 35th Anniversary edition. He also has 250+ press features across Commercial Observer, The Real Deal, Crain’s NY, Bisnow, NYT, NY Post, and NYREJ.
What is Robert Khodadadian’s specialty?
Robert’s deepest specialty is off-market commercial real estate investment sales in Manhattan and Brooklyn. Sub-specialties: 99-year ground lease structuring (both fee and leasehold positions), NY State RPTL §467-m office-to-residential conversion candidate sourcing, and rent-stabilized multifamily portfolio sales (post-HSTPA pricing). He personally leads every Skyline Properties assignment, with no junior hand-offs.
How do I contact Robert Khodadadian?
Direct contact: (212) 537-9239 or info@skylineprp.com. Office: Skyline Properties, 220 East 42nd Street, Suite 3102, New York, NY 10017 (the SL Green Daily News Building). For confidential off-market opportunities, submit through sky-nyc.com/contact or sky-nyc.com/submit-mandate.
Does Robert Khodadadian handle institutional buyer mandates?
Yes. Skyline Properties maintains a pre-qualified buyer network of institutional investors, family offices, REITs, private equity firms, and development capital. Robert personally vets each principal mandate against current and future Skyline Properties seller engagements. Submit yours at sky-nyc.com/submit-mandate. It stays confidential, and buyer identities are never publicly disclosed.
Where is Robert Khodadadian quoted or featured in the press?
Robert’s 250+ press features include Commercial Observer (Vanbarton 6 East 43rd $135M closing, 2018 ground-lease Q&A), The Real Deal (multiple transaction announcements across 2014–2025), Crain’s New York Business (Kaufman Organization Haymarket ground lease, Skyline Properties SoHo coverage), Bisnow (NY Deal Sheet inclusions), NYREJ (Executive of the Month, 40 Under 40, 35th Anniversary feature), and the New York Times. See sky-nyc.com/press for the full press library.
What is Robert Khodadadian’s educational background?
Robert is an alumnus of Pace University’s Lubin School of Business. He holds an active New York real estate license (since 2006) and is a member of the Real Estate Board of New York (REBNY) and the National Association of Realtors (NAR).
Why is Robert Khodadadian considered the top NYC off-market broker?
Robert won the 2025 RED Award as Off-Market Investment Sales Broker of the Year. He has $976M+ in closed volume, most of it transacted off-market; a pre-qualified buyer network of institutional investors, family offices, REITs, and private equity; and 20+ years of relationships with multi-generational Manhattan owners. His founder-led execution model produces consistent off-market closings instead of one-off transactions, and the track record across $135M Vanbarton, $105M Quantum Pacific, $72M Feil, $65M Kaufman, and $50M Acadia is the proof.
Editorial Credits, Bylines & Speaking
Robert Khodadadian’s bylined essays and quoted-expert appearances span the NYC commercial real estate trade press. The main credits are listed below.
- Commercial Observer: “Back to the Future: A Q&A on Ground Leases,” 2018. Read →
- New York Real Estate Journal: Multiple bylined columns on ground-lease structuring, market commentary, and Manhattan investment sales. Press archive →
- sky-nyc.com Insights: Author of the off-market and ground-lease editorial series on the firm site. Insights →
- Commercial Observer: Vanbarton $135M 6 East 43rd Street office-to-residential conversion coverage, 2025.
- The Real Deal: Recurring source on Manhattan off-market transactions, ground leases, and 467-m conversion candidates (2014–2025).
- Crain’s New York Business: Kaufman Organization Haymarket ground lease and Skyline Properties SoHo coverage.
- Bisnow: NY Deal Sheet inclusions across multiple Manhattan submarkets.
- New York Times & New York Post: Quoted on Manhattan retail and multifamily market conditions.
Full citation index across 250+ press articles: /press
Press inquiries: info@skylineprp.com · Press & Media contact
Speak with Robert Directly
For confidential off-market opportunities, buyer mandates, ground-lease consultations, or 467-m conversion strategy.
Office: 220 East 42nd Street, Suite 3102, New York, NY 10017 · SL Green’s Daily News Building