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.

09/26/2026

Old Town has plenty of history. What it rarely has is a brand-new secret.

419 Simonton Street · Unit C, Key West is now ACTIVE on the market!

A standalone residence within an intimate complex of just three condominiums. Brand-new construction with cathedral ceilings, a kitchen worth canceling reservations for, and interiors furnished by Ben Teague Design.

Outside, a private patio, water-feature pool and outdoor shower create a retreat of its own—all tucked away just one block from Duval Street.

2 Bedrooms | 2.5 Bathrooms
Brand-New 2026 Construction
Private Pool
Fully Furnished
Golf Cart Parking

OPEN HOUSE
Sunday, September 27
11 AM–1 PM

See more at the link in bio or DM us for a private showing.

CAN KEY WEST STILL BE A HOME FOR WRITERS?Lynn Kaufelt interviewed and quoted in The New York Times.In a new article for ...
08/01/2026

CAN KEY WEST STILL BE A HOME FOR WRITERS?

Lynn Kaufelt interviewed and quoted in The New York Times.

In a new article for The New York Times, writer Dorie Chevlen (Dorie Chevlen) examines the future of Key West’s celebrated literary culture—with Lynn featured as a distinctive voice in the island’s enduring story.

Photography by Mark Hedden (Mark Hedden)

Lynn is the author of “Key West Writers and Their Houses,” an intimate exploration of the homes and lives of the writers who shaped Key West. Her connection to that legacy extends well beyond the page.

The Key West Literary Seminar (Key West Literary Seminar) was founded in 1983 by Lynn’s late husband, novelist David A. Kaufelt. Lynn served as its first director and later as president of its board, helping carry forward the literary tradition they championed together.

The Seminar’s stewardship of the Elizabeth Bishop House—seen in this carousel—is more than an act of historic preservation. For Lynn, it is a living link between Key West’s extraordinary literary past and the writers who still call the island home today.

Can Key West preserve that legacy while making room for the writers who will define its next chapter?

Read the full New York Times story at the link in our bio—and tell us what you think.

KeyWest

The Secret Garden House Closed by Teamkaufelt & Elizabeth Chamberlain (Elizabeth Chamberlain | 816 Johnson Lane, Key Wes...
07/24/2026

The Secret Garden House

Closed by Teamkaufelt & Elizabeth Chamberlain (Elizabeth Chamberlain | 816 Johnson Lane, Key West
Sold for full ask with only 2 days on the market.

There’s a hidden garden in the middle of Old Town Key West… And in just two days, it found its next chapter.

TEAMKAUFELT brought this historic property to market with a carefully considered launch: distinctive visual storytelling, targeted exposure, and an opening-day open house that welcomed more than 100 people through the gates.

The response was immediate.

Multiple offers followed, and within two days we secured a full asking-price contract with no contingencies and a quick closing for our sellers.

That kind of result begins with understanding what makes a property truly special, then presenting it in a way that allows the market to feel it.

Rooted in Key West’s cigar cottage history and surrounded by a remarkable tropical garden, 816 Johnson Lane offered architectural integrity, privacy, and an authenticity that could not be replicated.

It is always a pleasure working alongside Elizabeth Chamberlain, whose professionalism and collaborative approach helped bring the right buyers to this very special property.

We would also like to thank closing agent Richard McChesney (thecoastalservice), whose experience and persistence helped navigate a unique title issue and bring the transaction to a successful close.

Congratulations to our sellers and to the new stewards of The Secret Garden House.

Considering selling in Key West? DM SECRET GARDEN for a private look at the strategy behind this sale.

THIS IS THE PLAY.1503 Atlantic Boulevard is now live in Key West.Big lot. Pool. Atlantic Boulevard address. Multi-unit f...
07/13/2026

THIS IS THE PLAY.

1503 Atlantic Boulevard is now live in Key West.

Big lot. Pool. Atlantic Boulevard address. Multi-unit flexibility. And the kind of upside that gets harder to find every year.

Set on an approximately 8,050 SF lot with roughly 2,750 SF of living area, this property gives the next owner something rare in Key West: room to think bigger.

Renovate it. Reimagine it. Hold it as income. Create the tropical compound. The aerials show the scale. The outdoor spaces show the setting. But to understand the upside, you need to get inside.

1503 Atlantic Blvd, Key West
Offered at $1,350,000

DM TEAMKAUFELT📍Key West Real Estate to get inside.

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! 🕊️🕊️🕊️

Address

1205 Truman Avenue
Key West, FL
33040

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