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TEAMKAUFELT | Marketing Your Key West Real Estate to the World

Key West Realtor
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Key West Real Estate Leading RE
Key West Real Estate
Key West Realtor

 

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Key West Luxury Homes | 810 Eisenhower Drive, Key West, FL | MLS# 614269

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1211 Olivia Street
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822 Georgia Street, Key West, FL | MLS# 612933

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KEY WEST, Florida 33040

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711 Ashe Street, Key West, FL | MLS# 612932

711 Ashe Street
KEY WEST, Florida 33040

  • 2Beds
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804 Ashe Street, Key West, FL | MLS# 612463

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3625 Sunrise Drive, Key West, FL | MLS #611844

3625 Sunrise Drive
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3075 Flagler Avenue, #1, Key West, FL 33040 | MLS #610149

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704 Eaton Street, Key West, FL 33040 | MLS #610059

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11 Father Tony Way, Big Pine Key, FL 33043

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218 Golf Club Drive, Key West, FL 33040

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1014 Flagler Avenue 618577

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901 Johnson Street 618506

901 Johnson Street
KEY WEST, Florida 33040

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419 Simonton Street A 618250

419 Simonton Street A
KEY WEST, Florida 33040

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419 Simonton Street C 618252

419 Simonton Street C
KEY WEST, Florida 33040

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910-914 Watson Street 617923

910-914 Watson Street
KEY WEST, Florida 33040

  • 5Beds
  • 7Baths
  • 4,387Sq ft
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Some homes are built; others are authored. This is one of the latter--an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been meticulously restored to museum-level standards with all-new systems, impact-rated windows and doors, and 10-foot doors and sliders throughout. The dramatic main living space is defined by soaring 22-foot ceilings, refinished custom teak columns and doors, expansive walls of glass, and a striking floor-to-ceiling built-in bookcase spanning the full height and length of the living room wall, complete with a concealed automatic disappearing television, while a thoughtfully designed chef's kitchen anchors the home with both beauty and functionality for everyday living and entertaining. Set on a rare, fully walled corner double lot spanning more than 11,700 square feet, the property is enveloped by indigenous and exotic landscaping and hardscape design by Craig Reynolds Landscape Architecture, creating a private, resort-style environment centered around an oversized 40′ x 20′ custom heated swimming pool and generous outdoor living areas--an extraordinary sense of scale and seclusion in the heart of Casa Marina. The main residence offers two bedrooms and two-and-a-half bathrooms, complemented by a separate one-bedroom, one-bath guest house with its own kitchen, washer and dryer, and private garden, providing ideal accommodations for guests, extended family, or additional flexibility, all located on one of the most desirable blocks in one of Key West's premier neighborhoods, where privacy, scale, architectural pedigree, and legacy converge. $6,495,000 Active

1014 Flagler Avenue KEY WEST, Florida

3 Beds 4 Baths 3,104 SqFt

More than a residence and rarer than legend, 910-914 Watson Street stands as one of the most iconic private estates in all of Key West--a once-in-a-generation offering where historic gravitas, tropical scale, and modern refinement converge behind gated walls in the heart of Old Town. Just moments from Truman Waterfront Park and beloved local favorites such as 5 Brothers Coffee and Cafe Sole, this historic estate delivers the rare combination of island ease and cultivated sophistication. Bathed in natural light, the home's timeless architecture artfully blurs the line between indoors and out, creating spaces that feel both expansive and intimate. Anchoring the tropical grounds is a resort-style pool and spa framed by tranquil water features and a serene koi pond. The experience is elevated further by an oversized covered pool loggia, designed for effortless island living and entertaining, featuring outdoor dining, a fully equipped outdoor kitchen, and a generous living area--all sheltered and inviting year-round. The enclosed, gated grounds offer rare privacy and practicality, including two-car garages and off-street parking for at least six additional vehicles--an exceptional luxury in Old Town. A dedicated dog run with motorized gate and lush landscaping complete the sense of a hidden tropical sanctuary. Spanning 4,387 square feet, the estate includes five bedrooms and six and a half baths, thoughtfully arranged for both togetherness and autonomy. A one bedroom suite resides in a separate guest house with its own entrance, front porch, and living space, ideal for a mother-in-law suite, long-term guests, or on-site grounds personnel. Set on an expansive 13,182 square-foot lot in the coveted X-500 Flood Zone, the property is equally suited for lively gatherings or quiet moments of retreat. $5,995,000 Active

910-914 Watson Street KEY WEST, Florida

5 Beds 7 Baths 4,387 SqFt

DOUBLE LOT. DOUBLE CORNER. CASA MARINA. A rare generational opportunity in Key West's iconic Casa Marina neighborhood--an internationally recognized landmark enclave defined by tropical estates and timeless island character. Held by the same family since 1977, this property sits on a highly desirable double corner lot with legal rental flexibility and exceptional long-term upside. The 1958 architectural gem offers privacy, presence, and classic Key West charm, with the opportunity to thoughtfully renovate or reimagine for today's living. The property offers a total of three bedrooms and four bathrooms including a separate studio apartment located above the garage with its own kitchen and bath, ideal for income, guests, or extended family. The outdoor setting is quintessentially Key West, with mature tropical landscaping, room for a pool, and two extraordinary specimen trees--one of the island's finest Lignum Vitae and a striking Jamaican Dogwood--adding natural beauty and irreplaceable heritage. All of this is just minutes from the best of the island lifestyle, including Higgs Beach, White Street Pier, dog parks, Louie's Backyard, and Salute, all within walking distance. This iconic residence is a rare Casa Marina offering where land, location, and landmark legacy truly speak for themselves. $2,950,000 Active

901 Johnson Street KEY WEST, Florida

3 Beds 4 Baths 2,507 SqFt

Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined kitchen with Fisher & Paykel and Bosch appliances, a walk-in pantry, under-cabinet lighting, and refined finishes throughout. Outdoors, a secluded patio is framed by vibrant tropical landscaping and includes a tranquil water-featured pool, outdoor shower, and dedicated golf cart parking--the preferred way to get around Old Town. Offered fully furnished with a curated interiors package by Ben Teague Design, the home is move-in ready and thoughtfully finished. Set within a well-structured HOA with no shared walls, and part of a three-residence property with two additional homes positioned at the front and parking conveniently located there, this residence represents Old Town living at its most refined--entirely new, intentionally designed, and quietly confident in every detail. $2,185,000 Active

419 Simonton Street C KEY WEST, Florida

2 Beds 3 Baths 1,367 SqFt 0.14 Acres

Located in the heart of Key West's Historic District, 905 Grinnell Street is a distinctive multi-unit property that blends architectural character with strong investment performance. Originally built as a church, the structure has been thoughtfully converted into four residential units totaling 3,383 square feet. Each unit is individually metered and currently leased, offering a stable and reliable return. The property offers stable, predictable cash flow in one of Florida's most desirable markets, with a central location that places it within walking distance of local shops, dining, and attractions. Whether expanding your portfolio or seeking a turnkey income-producing property, 905 Grinnell Street delivers a rare combination of historic charm, prime location, and investment performance. Rental numbers available upon request. $2,095,000 Active

905 Grinnell Street KEY WEST, Florida

8 Beds 4 Baths 3,383 SqFt 0.13 Acres

The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West--authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction completed in January 2026 and every system, surface, and finish entirely new. Offered fully furnished with a bespoke interiors program by Ben Teague Design, the residence is layered with thoughtful selections, timeless materials, and a quiet sophistication that feels both intentional and effortlessly livable. The home offers two bedrooms and two-and-a-half baths, including an upstairs primary bedroom that opens to a classic Key West porch, while a second porch downstairs extends the living space and reinforces the home's effortless indoor-outdoor rhythm. Architect-led design and professionally curated landscaping elevate the curb appeal to a truly top-tier example of Old Town style--timeless proportions, thoughtful detailing, and a presence that feels historic without feeling precious. The property is part of a thoughtfully structured HOA, which also includes one attached residential unit positioned to the rear of the main home, as well as a separate detached unit located at the back of the property--allowing for shared stewardship while preserving privacy and architectural integrity. Set on one of the highest elevation blocks in Old Town and located in the coveted X-500 flood zone, this is a rare opportunity to own a home where heritage, design integrity, and modern peace of mind converge on one of Key West's most iconic streets. $1,485,000 Active

419 Simonton Street A KEY WEST, Florida

2 Beds 3 Baths 1,123 SqFt

MARKETING KIT

ABOUT US

TEAMKAUFELT is proud to be recognized as the #1 active real estate team in Key West per the MLS for 2022 and 2023. In a year marked by extraordinary shifts in the marketplace we worked together to provide local expertise, real estate knowledge, and unmatched responsiveness.

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GET IN TOUCH

Lynn Kaufelt | 305.923.4276
Jackson Kaufelt | 305.393.1267
Ethan Perloff | 540.450.7315

teamk@trumanandcompany.com
www.teamkaufelt.com
1205 Truman Avenue | Key West, FL 33040

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Leading Real Estate Companies of the World
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TEAM KAUFELT

Truman & Company

1205 Truman Avenue
Key West, FL 33040
Mobile: 305.393.1267
Office: 305.292.2244
teamkaufelt@trumanandcompany.com
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