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Featured Properties

Handpicked homes and properties that represent the best of Key West living — luxury, location, and lifestyle.
For Sale 412 Frances Street

412 Frances Street, Key West, FL 33040

$11,500,000

15 Beds
18 Baths
5,731 Sq.Ft.

Property description

Heron House Court presents a unique chance to own a boutique guesthouse in the heart of Old Town Key West. This historic gem has been well maintained through the years & offers 15 deluxe rooms (14 ...

Property Details
For Sale 616 Eaton Street

616 Eaton Street, Key West, FL 33040

$7,495,000

5 Beds
7 Baths
4,000 Sq.Ft.

Property description

Nestled in the heart of Key West's historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and pains...

Property Details
For Sale 1006-1008 Fleming Street

1006-1008 Fleming Street, Key West, FL 33040

$4,998,000

4 Beds
5 Baths
3,336 Sq.Ft.

Property description

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across thre...

Property Details
For Sale 720D Simonton Street

720D Simonton Street, Key West, FL 33040

$4,990,000

4 Beds
4 Baths
2,441 Sq.Ft.

Property description

KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departu...

Property Details
For Sale 406 United Street

406 United Street, Key West, FL 33040

$4,699,000

4 Beds
5 Baths
3,624 Sq.Ft.

Property description

A Grand Historic Masterpiece! Few residences capture the true spirit of Old Town Key West quite like 406 United Street. Rooted in one of the island's most defining eras of growth and prosperity, th...

Property Details
For Sale 1113 Stump Lane

1113 Stump Lane, Key West, FL 33040

$4,595,000

4 Beds
5 Baths
2,985 Sq.Ft.

Property description

Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old To...

Property Details
For Sale 1501 Georgia Street

1501 Georgia Street, Key West, FL 33040

$3,699,000

4 Beds
5 Baths
2,810 Sq.Ft.

Property description

1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,...

Property Details
For Sale 1200-1206 White Street

1200-1206 White Street, Key West, FL 33040

$3,199,000

1 Bath
Sq.Ft.

Property description

PRIME INVESTMENT OPPORTUNITY! 3 Commercial Condos + 2 Residential Condos on White Street in X Flood Zone. Newly formed condo building on busy Old Town Street. 3 Commercial units 1st floor, 2 reside...

Property Details
For Sale 410 Louisa Street

410 Louisa Street, Key West, FL 33040

$2,699,000

3 Beds
3 Baths
2,002 Sq.Ft.

Property description

Experience the epitome of luxury in this exquisite 3BD/3BA residence nestled on a quiet Lane in the heart of Old Town Key West, just a stone's throw from the world famous Southernmost Point and 1 b...

Property Details
For Sale 1427 Washington Street

1427 Washington Street, Key West, FL 33040

$2,525,000

4 Beds
3 Baths
2,051 Sq.Ft.

Property description

Located in a charming midtown neighborhood sits this beautifully renovated 4BD/2.5BA Key West home with just over 2,000sf of living space. Upon entering the home you will find a first floor bedroom...

Property Details
For Sale 1109 Stump Lane

1109 Stump Lane, Key West, FL 33040

$2,395,000

3 Beds
4 Baths
1,724 Sq.Ft.

Property description

Nestled on a tranquil lane in Old Town Key West, this classic Conch home is designed for relaxed island living. The property offers multiple entertainment spaces both indoors and out, with the expa...

Property Details
For Sale 17210 Angelfish Lane

17210 Angelfish Lane, Sugarloaf Key, FL 33042

$2,299,999

3 Beds
3 Baths
2,288 Sq.Ft.

Property description

Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of ...

Property Details
For Sale 1116 Elgin Lane

1116 Elgin Lane, Key West, FL 33040

$2,249,000

3 Beds
2 Baths
1,516 Sq.Ft.

Property description

There are streets in Old Town that everyone knows, and then there are streets like Elgin Lane that most people never even realize exist. Quiet, tucked away, and remarkably private, this hidden lane...

Property Details
For Sale 1706 Seminary Street

1706 Seminary Street, Key West, FL 33040

$2,199,000

3 Beds
3 Baths
1,938 Sq.Ft.

Property description

Tucked behind a new privacy fence, 1706 Seminary Street is a fully renovated home where thoughtful design meets laid-back Key West living. Set on a generous 7,480 square foot lot, this 3-bedroom, 3...

Property Details
For Sale 3841 N Roosevelt Boulevard Unit: 315

3841 N Roosevelt Boulevard Unit: 315, Key West, FL 33040

$1,949,000

2 Beds
3 Baths
1,357 Sq.Ft.

Property description

Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two trans...

Property Details
For Sale 3841 N Roosevelt Boulevard Unit: 332

3841 N Roosevelt Boulevard Unit: 332, Key West, FL 33040

$1,949,000

2 Beds
3 Baths
1,357 Sq.Ft.

Property description

Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two trans...

Property Details
For Sale 1229 5Th Street

1229 5Th Street, Key West, FL 33040

$1,899,000

6 Beds
3 Baths
3,197 Sq.Ft.

Property description

Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CB...

Property Details
For Sale 408 William Street

408 William Street, Key West, FL 33040

$1,800,000

4 Beds
3 Baths
1,943 Sq.Ft.

Property description

Blending timeless character and modern comfort this home is nestled on one of Old Town's most coveted streets. Come discover this captivating home steeped in rich history. The kitchen has been thou...

Property Details
For Sale 1616 Atlantic Boulevard Unit: 3

1616 Atlantic Boulevard Unit: 3, Key West, FL 33040

$1,599,000

2 Beds
3 Baths
1,940 Sq.Ft.

Property description

OFFERED FULLY FURNISHED and completely renovated, this is the townhome buyers wait for and almost never get. Every finish, every furnishing, and every detail has been thoughtfully curated to delive...

Property Details
For Sale 1409 Olivia Street

1409 Olivia Street, Key West, FL 33040

$1,469,500

2 Beds
3 Baths
1,053 Sq.Ft.

Property description

Discover the rare convergence of Old Town authenticity and contemporary refinement in this meticulously restored 1945 conch cottage. Brought to life through a 95% rebuild by renowned architect Denn...

Property Details
For Sale 1317 Newton Street

1317 Newton Street, Key West, FL 33040

$1,299,900

2 Beds
3 Baths
1,386 Sq.Ft.

Property description

Step into island living with this beautifully updated home in one of Key West's most desirable neighborhoods. Recently painted inside and out, this cottage features stainless-steel appliances, glea...

Property Details
For Sale 3841 N Roosevelt Boulevard Unit: 222

3841 N Roosevelt Boulevard Unit: 222, Key West, FL 33040

$999,000

3 Beds
3 Baths
1,586 Sq.Ft.

Property description

Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatile vacation rental. Fully fu...

Property Details
Active Under Contract 3 Birchwood Drive

3 Birchwood Drive, Key Haven, FL 33040

$915,000

3 Beds
1 Bath
1,223 Sq.Ft.

Property description

Tucked away on a quiet street, 3 Birchwood Drive represents a rare chance to own in one of the most sought after neighborhoods near Key West, at a price point rarely seen. This 3 bedroom, single le...

Property Details
For Sale 3841 N Roosevelt Boulevard Unit: 213

3841 N Roosevelt Boulevard Unit: 213, Key West, FL 33040

$899,000

2 Beds
3 Baths
1,357 Sq.Ft.

Property description

Discover the ultimate fusion of luxury and part time usage with this transient-licensed, 2-bedroom, 2.5-bath condo in Key West. Perfectly suited for vacation rentals, it offers the flexibility of a...

Property Details

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