Team Kaufelt, Truman & Co. Real Estate

Team Kaufelt, Truman & Co. Real Estate BESTSELLERS. Team Kaufelt SELLS houses. Lots of houses. Big houses, little houses, medium houses. That's why we've sold over 27 million in 2017 so far.
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TEAMKAUFELT is proud to be recognized as the number #1 active real estate team per the MLS for the second year in a row, beating the market year over year by more than 20%. That's because they have marketing savvy and the know-how to use it.

419 Simonton Street A | Closed for $1.325MKey West Historic DistrictBuilt in 1889. Reimagined in 2026.Sold for $1.325M a...
05/23/2026

419 Simonton Street A | Closed for $1.325M
Key West Historic District
Built in 1889. Reimagined in 2026.

Sold for $1.325M after only 64 days on market at $1,225 per square foot — a reflection of what buyers continue to pursue in the Historic District: authenticity, design, and irreplaceable location.

Before it became one of Old Town’s most compelling residential restorations, this address lived many lives — including a chapter as a neighborhood flower shop woven into the fabric of Simonton Street. Today, it stands restored with intention: honoring the architecture and soul of Old Key West while delivering a completely modern standard of living.

This sale marks the second closing within the compound, leaving just one remaining opportunity:

419 Simonton Street C

A rare chance to own a piece of Key West history that has already proven its demand.

Represented by of

KeyWestHomes HistoricHomes FloridaRealEstate LuxuryHomes SimontonStreet TeamKaufelt

05/16/2026

Where the shower feels like rain in the jungle and the pool disappears into paradise.

Tucked away in the heart of Old Town at 419 Simonton Street C, this private retreat was designed to feel worlds away. An outdoor shower surrounded by exotic landscaping, tranquil water features, and a resort-style pool create the kind of atmosphere that defines luxury living in Key West. Every path, every palm, every detail was intentionally designed to blur the line between home and escape.

This is the side of Key West people dream about — and rarely find.

Listed exclusively by TeamKaufelt with Truman & Co.

The pool stops you first.Then the grounds take over.A property like this doesn’t exist anywhere else in Key West.Origina...
05/15/2026

The pool stops you first.Then the grounds take over.

A property like this doesn’t exist anywhere else in Key West.

Originally owned by David Wolkowsky and restored to museum-level standards, this iconic Casa Marina estate is a masterclass in architecture, landscape, and atmosphere.

40’ x 20’ heated pool.Custom water feature by .Rare double lot.22-foot ceilings.Indoor-outdoor living at an entirely different level.

Every path.Every reflection.Every detail was designed to be experienced.

Now offered at $4,995,000.

📍1014 Flagler AvenueCasa Marina District, Key West

Experience the complete listing at1014flagler.trumanandcompany.com

DM for private showing or details.

A brand-new home in Old Town.Hidden in plain sight.OPEN HOUSE | 419 SIMONTON ST, CSaturday | 12–2PNew construction in th...
05/13/2026

A brand-new home in Old Town.
Hidden in plain sight.

OPEN HOUSE | 419 SIMONTON ST, C
Saturday | 12–2P

New construction in the historic district is exceptionally rare — especially on one of Old Town’s most coveted blocks.

Completed in 2026 and quietly tucked away behind the charm of Simonton Street, this newly built residence offers something almost never found in Key West:

A private, refined retreat in the very heart of Old Town.

Thoughtfully designed for seamless indoor-outdoor living, the home blends contemporary luxury with the intimacy and character that make Old Town so desirable.

Now offered at $2,070,000 following a notable price adjustment.

Experience one of Old Town’s rarest offerings this Saturday from 12–2P.

Video, 3D Tour & More:
419simontonstreetc.trumanandcompany.com

Jackson Kaufelt | Truman & Co.
[email protected]
(305) 393-1267

05/12/2026

Who else is enjoying the Sunset in Key West this evening? This great white heron at Truman Waterfront Park understood the assignment! 🕊️🕊️🕊️

05/08/2026

Behind the gates of 816 Johnson Lane lies one of the most enchanting private gardens in Old Town Key West.

OPEN HOUSE
Saturday | 11AM–1PM

The Secret Garden House is a rare tropical sanctuary where lush layered landscaping, historic architecture, and indoor-outdoor living come together with effortless elegance. Towering palms, orchids, hidden pathways, shaded lounges, and candlelit corners create a setting that feels entirely removed from the outside world.

More than beautiful — this property feels transportive.

A truly iconic Key West compound designed for slow mornings, ocean breezes, intimate gatherings, and life lived connected to nature.

📍816 Johnson Lane, Key West

DM for private details or a showing.



KeyWestRealEsTate

05/07/2026

There’s a hidden garden in the middle of Old Town Key West… and most people have never seen it. 🌿

OPEN HOUSESaturday | 11AM–1PM📍816 Johnson Lane, Key West

For a limited time, this hidden sanctuary opens its gates to the public.

Known as The Secret Garden House, this historic island retreat feels worlds away — where winding tropical pathways, lush courtyards, and timeless architecture create a sense of rare tranquility and escape.

Originally rooted in Key West’s cigar cottage history and thoughtfully transformed over time, the property has become an iconic expression of indoor-outdoor island living — private, storied, and entirely authentic to the spirit of Old Town.

Offered at $1.175MListed by TEAMKAUFELT |

DM for private details or a personal tour.

Hidden on a quiet lane in the heart of Old Town Key West, The Secret Garden House is more than a home — it’s a private t...
05/07/2026

Hidden on a quiet lane in the heart of Old Town Key West, The Secret Garden House is more than a home — it’s a private tropical sanctuary where history, architecture, and nature exist in complete harmony.

Originally built as two cigar workers’ cottages in the early 1900s, the homes were thoughtfully joined and transformed into a one-of-a-kind compound celebrated for its iconic interpretation of tropical modernism and handcrafted island living. Featured in Design Within Reach Magazine and other notable publications, the property captures the soul of authentic Key West in a way few homes ever do.

Lush tropical gardens, intimate outdoor spaces, orchids, native palms, and a rare historic working well create a setting that feels worlds away. Inside, skylights, breezeways, disappearing sliders, exposed beams, and whitewashed interiors blur the line between indoors and outdoors with effortless elegance.

Private, artistic, and entirely authentic, this is the kind of Key West property rarely offered. 🌴

📍816 Johnson Lane, Key West

✨ OPEN HOUSE
Saturday | 11AM–1PM

Now being offered for the first time in its next chapter.

DM for additional information or a private showing.

Hidden on a quiet lane in the heart of Old Town Key West, The Secret Garden House is more than a home — it’s a private t...
05/07/2026

Hidden on a quiet lane in the heart of Old Town Key West, The Secret Garden House is more than a home — it’s a private tropical sanctuary where history, architecture, and nature exist in complete harmony.

Originally built as two cigar workers’ cottages in the early 1900s, the homes were thoughtfully joined and transformed into a one-of-a-kind compound celebrated for its iconic interpretation of tropical modernism and handcrafted island living. Featured in Design Within Reach Magazine and other notable publications, the property captures the soul of authentic Key West in a way few homes ever do..

Private, artistic, and entirely authentic, this is the kind of Key West property rarely offered.

816 Johnson Lane, Key West | $1,175M
Listed by TEAMKAUFElT |

OPEN HOUSE
Saturday | 11AM–1PM

Now being offered for the first time in its next chapter.



DM for additional information or a private showing.

Set apart from anything else on the market.A Casa Marina property with true scale, refined interiors, and grounds that f...
04/24/2026

Set apart from anything else on the market.

A Casa Marina property with true scale, refined interiors, and grounds that feel intentional at every turn.

Take it in.
Walk the space.

Built for how Key West living should feel.

Open house this Sunday
12–2 PM

Now offered at $5,230,000.

📍1014 Flagler Avenue
Casa Marina District, Key West

A standout property in one of the island’s most established neighborhoods.

DM for details or a private showing.

Explore the full listing at 1014flagler.trumanandcompany.com

Address

1205 Truman Avenue
Key West, FL
33040

Telephone

+13053931267

Website

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