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THE ISLAND / THE HOMES / THE PEOPLE
Explore Key West.
SIGNIFICANT
SALES.
Distinctive homes. Remarkable addresses. A selection of closings that tell the story of our market.
Every property
has a point of view.
Some homes are defined by their architecture. Others by their gardens, their history or a setting that simply cannot be replicated.
At TEAMKAUFELT, led by Lynn and Jackson Kaufelt of Truman & Company, our perspective is shaped by years spent working in Key West’s most distinctive neighborhoods. These selected transactions show the range of properties and clients we have represented.
81 Cannon Royal Drive
A notable waterfront transaction in the team’s longer history. This Shark Key property closed for $6,225,000 in October 2016; it is included as a legacy sale, not a current-market comparable.
VERIFY THE SALEFlagship closings.
CLOSED / 2025810 Eisenhower Drive
SELLER REPRESENTED AUGUST 2025
A historic Victorian residence, restored for contemporary island living.
Original Dade County pine, period details, an expansive corner parcel and a secluded tropical setting give this 1912-era property a distinct sense of place.
4 bedrooms · 2,177 SF · 8,800 SF lot
VIEW THE PROPERTY
CLOSED / 2025802 Southard Street
SELLER REPRESENTED JUNE 2025
An architectural landmark with timeless Old Town character.
An exceptional corner residence distinguished by broad verandas, period craftsmanship and lush outdoor living. The closing underscores the continued appeal of distinctive historic homes.
4 bedrooms · 2,310 SF · Heated pool
VIEW THE PROPERTY
CLOSED / 2024704 Eaton Street
SELLER REPRESENTED OCTOBER 2024
A celebrated preservation story in the heart of Old Town.
An 1850s Old Town residence restored by Dale Earnhardt Jr. and Amy Earnhardt, with its preservation story featured on television. Original architectural details, expertly considered interiors and a custom pool give this home a distinct place in Key West design history.
3 bedrooms · 2,369 SF · Historic preservation
VIEW THE PROPERTYThe most compelling homes are not interchangeable. Neither should their representation be.
From landmark Old Town estates to Casa Marina retreats, the details matter: history, site, architecture, condition and the buyers who recognize their value.
Selected transactions.
SELLER REPRESENTED1017 Margaret Street
Architectural scale in an established Old Town address.
4 bedrooms · 2,400 SF · Closed Dec. 2023
EXPLORE SALE
SELLER REPRESENTED1501 Georgia Street
A landscape-led home with exceptional indoor-outdoor flow.
4 bedrooms · 2,810 SF · 55-foot pool
EXPLORE SALE
BUYER REPRESENTED901 Johnson Street
A rare Casa Marina acquisition with legacy potential.
3 bedrooms · 2,507 SF · 10,175 SF lot
EXPLORE SALE
SELLER REPRESENTED1308 Reynolds Street
Classic Conch Cottage. Pool, parking and a guest retreat.
3 bedrooms · 1,662 SF · Guest cottage
EXPLORE SALE
SELLER REPRESENTED419 Simonton Street A
Historic architecture, thoughtfully reintroduced.
2 bedrooms · 1,082 SF · Historic restoration
EXPLORE SALEA curated selection of closed transactions, not a complete sales history. Prices reflect reported closing prices, not asking prices. Seller and buyer representation are identified separately. Property details and closing information are based on MLS and public listing records and may be independently verified.
WHAT’S YOUR
HOME’S STORY?
Thinking about selling an exceptional Key West or Lower Keys property? Let’s talk about its position in today’s market—and the people most likely to appreciate it.
