Selling your home
Your property deserves the world's attention.
Selling a home in the Upper Keys isn't like selling anywhere else. The buyers are discerning, the market is singular, and the strategy has to match both. Leslie Leopold and Annie Hagen have spent over two decades doing exactly that.
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LeslieLeopold
Leslie has built her reputation on honesty, integrity, and exceptional client service — representing sellers with professionalism, discretion, and unwavering dedication, regardless of a property's price point. She has represented everything from island cottages to some of the Florida Keys' most exceptional waterfront estates.
Annie Hagen
Born and raised in Islamorada, Annie pairs a lifelong understanding of these communities with innovative marketing — professional photography and video, social media, and digital advertising designed to maximize exposure for every listing. She is passionate about showcasing the very best of the Florida Keys.
Local Knowledge. Global Reach. Proven Results.
Most buyers searching for Florida Keys property begin their search somewhere else — New York, Chicago, London, São Paulo. Reaching them long before they ever set foot on the island requires a very specific kind of exposure.
Sotheby's International Realty connects our listings to a buyer pool no independent brokerage can assemble. But the network is only part of it. The other part is knowing exactly how to position your property — what story to tell, what price to anchor, and which buyers to pursue first.
Together, Leslie and Annie combine decades of proven experience with a fresh, modern approach to real estate. Their mother-daughter partnership blends trusted guidance, innovative marketing, and genuine local expertise, offering clients exceptional representation from waterfront estates and investment properties to family homes throughout the Florida Keys.
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$27,750,000
8 BD · 10 BA · 10,228 sq ft · Oceanfront
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How we sell your Keys home.
Every seller comes to us with different goals, different timelines, and a different relationship to the home they're leaving behind. This is our process. Consider it a starting point.
01
Valuation & Strategy Session
We review recent comparable sales, current inventory levels, and the unique characteristics of your property. We'll tell you what we think the market will bear and what strategy gets you there. If the timing isn't right to sell, we'll tell you that too. Honesty first.
02
Preparation & Presentation
We coordinate professional photography, aerial drone footage, and video walkthroughs. Our staging consultations are thoughtful, not generic, we know what Keys buyers respond to. Every image is edited to showcase natural light, water views, and the irreplaceable sense of place that makes these properties extraordinary.
03
Sotheby's Global Marketing
Through Ocean Sotheby's International Realty, your property is exposed to over 1,000 offices across 81 countries. Sotheby's clients are often the buyers of record-setting properties, and they come pre-qualified, internationally connected, and ready to transact at the highest level. No other brokerage in the Florida Keys offers this reach.
04
Local & Regional Outreach
Leslie and Annie's three decades of Keys relationships translate directly to buyers. We know who is quietly looking, which agents represent serious buyers, and which past clients are ready to upsize. Private showings with pre-qualified prospects often happen before a property hits the MLS, reducing days on market and protecting seller privacy.
05
Offer Management & Negotiation
Our buyer relationships extend well beyond the MLS. When appropriate, we leverage three decades of agent and client connections to create early interest — shortening timelines and, when a seller needs it, maintaining discretion throughout the process.
06
Contract to Close
We coordinate every piece — inspections, title work, lender communication, attorney review, and final walk-through. Keys transactions have unique complexities: flood zone insurance, deed restrictions, and Keys-specific environmental considerations. We navigate all of it. Our sellers close on time, informed at every step, and without unwelcome surprises.
A global stage for your Keys property.
When you list with Leslie and Annie, your property enters a marketing ecosystem that no independent Keys brokerage can offer. The Sotheby's International Realty network is the world's premier luxury real estate platform — and for sellers of exceptional properties, that distinction is measurable.
The buyers who close on record-setting Keys properties don't find them through local searches. They find them through Sotheby's — and they close with agents they trust.
Leslie Leopold and the OceanSIR team have been nothing short of exceptional. From helping us buy our first Keys property years ago to selling it last year at the record-breaking price for the Upper Keys, Leslie has been with us every step of the way. Having her by my wife and I’s side for some of the biggest and most meaningful transactions of our lives has been invaluable. Leslie is the ultimate ‘iron fist in a velvet glove’—incredibly knowledgeable, calm, and focused, yet tough and determined when it matters most (as every real estate deal inevitably requires). As we prepare to embark on the journey of finding our next home, there’s no doubt Leslie and her team will be in our corner.
The Keys to the Islands
Upper Keys Real Estate: Midyear 2026 Market Report
The numbers are in and for buyers, sellers, and anyone watching the Upper Keys real estate market, the first half of 2026 tells a compelling story.
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Villa Lago Named Sotheby's Extraordinary Property of the Day
We are proud to announce that Villa Lago — 75090 Overseas Highway, Islamorada — has been selected as the Sotheby's International Realty® Extraordinary Property of the Day, featured across the brand's global social media channels to an audience of more than one million followers worldwide.
Ready to find your place in the Keys?
Buying, selling, or simply curious what your property is worth. No pressure — just honest conversation from people who know this place better than anyone.