Vermont Real Estate, Backed by Global Exposure.

Residential, Land, Commercial, and Investment Sales.

Meet Leo Pond

Leo was born and raised in Chittenden, Vermont, just north of Rutland. He began his real estate career at sixteen, conducting market research for a boutique brokerage firm. That early immersion in data-driven marketing set the foundation for a career defined by precision, performance, and strategic insight.

Building on that analytical foundation, Leo went on to serve in multiple marketing roles with the United States Ski Team and the Killington World Cup Foundation.

Leo holds a Specialization in Financial Management from Duke University as well as a Specialization in Tax, Real Estate, and Alternative Investment Strategies from the University of Illinois Urbana-Champaign, deepening his expertise in advanced finance, investment modeling, and capital structuring.

Today, Leo represents a wide range of clients, from first-time homebuyers and families looking to upsize or relocate, to investors and commercial property owners. His approach combines institutional-level financial analysis with a personal, client-focused perspective, ensuring each property decision aligns with both lifestyle goals and long-term economic growth.

Leo sits on the Board of Directors of The Mentor Connector Inc., The Barstow Memorial School, and the Rutland Northeast Supervisory Union. He is a “friend” of the Middlebury College Art Museum.

Recognized for his market insight and analytical perspective, Leo has been featured in Fortune, CNBC, Yahoo Finance, Realtor.com, The New York Times and Forbes.

Our Service Portfolio

  • Buying in Vermont takes more than a search filter. I help you understand resale value, spot red flags early, and negotiate terms that protect you. Whether this is your first home or a second home near Killington, Burlington, Stowe or beyond, you’ll have an advocate who knows the market and tells you the truth about it.

  • Selling well starts long before the sign goes up. I price your home from real market data, position it against the competition and market it to the right buyers. You get a clear plan and steady communication from the first walkthrough to closing.

  • I represent owners of commercial property across Rutland County and Vermont, from mixed-use buildings to commercial land. Your property is priced on its income and potential, then presented to qualified buyers with the numbers they need to act.

  • Before you buy a commercial property, you should know exactly how it performs. I break down income, expenses, financing and risk so you can make an informed offer. Then I negotiate terms that fit your goals.

  • Selling a rental or multifamily property means telling a clear financial story. I prepare the rent roll, expenses and projected returns so investors see the value right away. That helps you attract stronger offers and close with fewer surprises.

  • Every investment should be backed by numbers. I prepare cash flow projections, rent comparisons and financing scenarios so you can see how a property performs before you buy it. From an owner-occupied duplex to a small apartment building, you’ll buy with confidence.

  • We are real estate advisors for charitable or noncharitable gifts of Real Estate. We help fiduciaries understand their obligations, and then help them with estate and trust liquidations. We provide referrals and work in tandem with trusted, licensed local professionals who can help with Legal, Financial, and Tax Advisement.

Get Started

  • "Leo was a fantastic resource throughout my search for a home in the Chittenden area. His local knowledge and insight were incredibly helpful. He was always communicative, informative, and positive. Working with him was a pleasure. I'm looking forward to moving into a home I love. Thank you, Leo!

    Julie

  • “Extremely Quick Sale! Thank you!”

    -- Randall Gilmour Esq., Estate Admin

  • “Leo went above and beyond, keeping things on track and getting us to a swift sale.”

    -- Administrator, The Estate of Vera Kotzek

  • “Leo is the best! He made the entire process easy. I went through FOUR real estate agents before him and he got the job done on the first house we looked at (my dream house). He believed in me and helped me believe in the process. Sotheby's charges an admin fee- Leo was worth EVERY PENNY of that fee. I was sad to be done working with him. He's a true professional, working for a truly professional company.”

    -- Rebecca Hyjek, First Time Homebuyer

  • "Leo is highly communicative and a very motivated fellow. We got offers the day after the open house he set up, advertised, and ran. I strongly recommend you give him a call and consider contracting him as your real estate agent"

    -C.J. Young

  • "Leo is an amazing Real Estate Advisor! He goes above and beyond! He is knowledgeable, supportive and guided us through the whole process. Leo is truly a gem. Thank you Leo!"

    -Rebekah Stephens, Habitat for Humanity Rutland County Executive Director

  • "Leo was extremely cordial professional at the same time.very thorough in how he showed me around the property. He was patient in answering my questions and did not hurry through the process. He was willing to do whatever it took to help me move forward. and clearly explained what needed to be done. Great personality and easy to work with

    -Margaret Morin

  • "Leo did a great job for us! He is professional, courteous and a good communicator. Leo helped us get the best price for our property and we recommend him 100%!"

    -Diane Lafleymills

Select a convenient time and our team will implement comprehensive solutions tailored to your objectives with measured precision.

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