Shepard Skiff, Agent in NYC - Compass

Shepard Skiff

Licensed Associate Real Estate Broker | Licensed as James S. Skiff

  • Manhattan & Brooklyn co-operative, condominium and townhouse sales

    • Corporate Relocation

    • Investment Management

    • First Time Buyers

    • Staging and Marketing Resales

    • New Development

    • Landlord Representation

    • Certified Negotiation Expert, CNE


    • B.A, Trinity College, Political Philosophy

    • Minor Latin American Studies & Spanish


    About Shepard

    Shep joined Compass after 10 successful years at Sotheby’s International Realty, where he worked with some of the industry's top brokers, and developed a refined full service skill-set. The roster of deals closed illustrates a track record of experience in the full range of price points, neighborhoods, and property types in Manhattan and Brooklyn. From townhouses and cooperatives, to downtown lofts and new development, Shep understands the nuances associated with all aspects of NYC real estate.

    Both sellers and buyers alike benefit from Shep's seasoned understanding of the market from top to bottom. A keen listener and communicator, he guides his clients each step of the way with patience and purpose to achieve their goals. With years of deal making under his belt in a wide range of prices and locations, Shep has developed an instinctual foundation to effectively do his job and service his clients.

    A Certified Negotiation Expert (CNE), Shep is a shrewd and skilled negotiator, and has a track record of happy clients on both sides of the fence. Strengthened by the best-in-industry tools at Compass, in depth market analysis is critical to his analysis of value. He has developed relationships with industry leading professionals in: legal and estate planning, financing, insurance, interior design and construction which his clients also benefit from.

    Raised in New England and Los Angeles, Shep went to prep-school in Western Massachusetts and graduated from Trinity College in Hartford, CT, earning a B.A. in Political Science and Spanish. He speaks Spanish, having lived abroad in Cordoba, Spain as well as the Dominican Republic. He has a keen interest in music, and prior to real estate he headed up the Latin America and Caribbean territory for the Putumayo World Music label.

    An avid athlete, Shep played competitive lacrosse (prep-school 2 x All American and top 5 all time points leader at Trinity) and soccer in school and continues to play a range of racquet games (squash, court tennis, tennis & racquets). He is also a golfer and a 2 x NYC marathon runner. Sport, whether played individually or on a team, has shaped many of the redeeming qualities that Shep incorporates into his work as a broker. Patience, a diligent and intelligent work ethic, preparation, and a strong will to work with others (and yes, against) to achieve a favorable result for all parties involved.

    Shep also believes in a life balanced by paying back the opportunities he's been afforded. He volunteers for several organizations like Streetsquash, Harlem & Citylax, Back-on-my-Feet-Again NYC, Church of the Ascension Food Pantry & First Presbyterian Homeless Shelter. He is on the Vestry at the Church of the Ascension, an Episcopal church in Greenwich Village. Painting, guitar, and photography satisfy his creative side. A Brooklyn resident for 12 years, Boerum Hill is home to him.

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