Real Estate Strategy and Advisement Built for Today’s Market.
Our Services
Strategic Real Estate Advisory
Whether you're acquiring your first home, repositioning an investment portfolio, or executing a 1031 exchange, our advisory approach is grounded in market intelligence, asset analysis, and long-term value creation. We align your real estate decisions with your financial goals — residential, land, or commercial.
Data-Driven Valuation & Marketing Strategy
We go beyond listing, we launch. Every property benefits from a tailored marketing plan rooted in valuation modeling, buyer profiling, and local market comps. From residential homes to commercial assets and raw land, we position your property to outperform the market.
Acquisition, Disposition & Contract Execution
We oversee the full transaction lifecycle, from due diligence and permitting to contract strategy and closing logistics. Our proactive negotiation style ensures you're not just closing deals, you're capitalizing on them, while staying protected from liability and delays.
Leo Pond is a full-service real estate advisor with Four Seasons Sotheby’s International Realty, representing clients across Rutland County and the Killington region with a focus on residential, land, and commercial assets. With a background in investment strategy and a deep understanding of local submarkets, Leo delivers data-backed guidance through every stage of the real estate cycle, from site acquisition, comparative market analysis, and pricing strategy, to contract structuring and closing coordination.
Known for integrating technology, automation, and AI into his advisory model, Leo helps clients capitalize on market opportunities through smarter marketing, optimized deal flow, and strategic positioning. Whether assisting with highest and best use scenarios, repositioning underutilized land, navigating seller-financed deals, or executing value-add investments, Leo provides clients with clarity, agility, and a competitive edge in a fast-moving market.
When you work with Leo, you're not just hiring a realtor, you're gaining a real estate strategist, negotiator, and local advocate dedicated to maximizing your ROI and protecting your bottom line.
Leo Pond is a Real Estate Advisor with Four Seasons Sotheby’s International Realty in Rutland & Killington, Vermont.
Leo Pond is proud to be recognized as a Silver Preferred Agent with Sotheby’s Concierge Auctions, a distinction that reflects his familiarity with the platform, experience with unique luxury properties, and commitment to providing elevated service throughout the auction process. This recognition aligns with Leo’s broader approach to real estate—offering tailored, high-level marketing strategies for exceptional homes. With a background in law and real estate, and formal training in luxury property marketing through Sotheby’s International Realty, Leo brings a sharp, strategic perspective to every listing, ensuring clients receive world-class representation and results.
Contact Us
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