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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

$5,595,000

4 Beds
5 Baths
3,336 Sq.Ft.

Property description

Exceptional Old Town compound with pool, gardens, and two guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully a...

Property Details
For Sale 1523 Patricia Street

1523 Patricia Street, Key West, FL 33040

$4,650,000

4 Beds
3 Baths
3,154 Sq.Ft.

Property description

Discover the epitome of island elegance with this stunning Spanish Mediterranean-style home situated on an expansive 10,000+ sq. ft. corner lot in the heart of Key West. This exceptional property o...

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
Active Under Contract 1020 Southard Street

1020 Southard Street, Key West, FL 33040

$3,599,000

3 Beds
4 Baths
2,438 Sq.Ft.

Property description

This stunning Gingerbread-style home seamlessly blends historic charm with modern luxury right in the heart of Old Town . A covered wraparound porch welcomes you into a bright, window-lined foyer, ...

Property Details
For Sale 33 Cypress Avenue

33 Cypress Avenue, Key Haven, FL 33040

$3,595,000

4 Beds
5 Baths
4,102 Sq.Ft.

Property description

Enjoy sweeping water views from this exceptional Key Haven home overlooking Cypress Lake. With 4 spacious bedrooms and 4.5 baths, the residence blends comfort and luxury in every detail. Built in 2...

Property Details
For Sale 1109 Stump Lane

1109 Stump Lane, Key West, FL 33040

$2,400,000

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 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 1706 Seminary Street

1706 Seminary Street, Key West, FL 33040

$2,249,000

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 1229 5Th Street

1229 5Th Street, Key West, FL 33040

$1,995,000

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 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 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 17213 Starfish Lane

17213 Starfish Lane, Sugarloaf Key, FL 33042

$1,799,000

3 Beds
2 Baths
1,750 Sq.Ft.

Property description

Tropical Paradise and Boater's Dream! Welcome to this custom-built 3-bedroom, 2-bathroom home in the prestigious Sugarloaf Shores, just 15 minutes from Key West and a short boat ride to the most st...

Property Details
For Sale 17213 Starfish Lane

17213 Starfish Lane, Sugarloaf Key, FL 33042

$1,799,000

3 Beds
2 Baths
1,750 Sq.Ft.

Property description

Tropical Paradise and Boater's Dream! Welcome to this custom-built 3-bedroom, 2-bathroom home in the prestigious Sugarloaf Shores, just 15 minutes from Key West and a short boat ride to the most st...

Property Details
For Sale 1317 Newton Street

1317 Newton Street, Key West, FL 33040

$1,399,900

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 247 Golf Club Drive

247 Golf Club Drive, Key West, FL 33040

$1,325,000

3 Beds
3 Baths
1,600 Sq.Ft.

Property description

Tucked inside the private gates of The Sanctuary at the Key West Golf Club, 247 Golf Club Drive is a true standout. This freestanding residence sits on a large lot with sweeping views of the lush f...

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
For Sale 701 Spanish Main Drive Unit: 221

701 Spanish Main Drive Unit: 221, Cudjoe Key, FL 33042

$995,000

2 Beds
2 Baths
864 Sq.Ft.

Property description

Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath...

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
For Sale 3705 Eagle Avenue

3705 Eagle Avenue, Key West, FL 33040

$859,500

6,000 Sq.Ft.

Property description

Rare opportunity to own a vacant, buildable 6,000 sq ft lot in Key West's New Town neighborhood. Located on sought-after Eagle Avenue, and on one of the best blocks too, this prime residential parc...

Property Details
For Sale 3711 Eagle Avenue

3711 Eagle Avenue, Key West, FL 33040

$859,500

2 Beds
2 Baths
1,464 Sq.Ft.

Property description

Located on the very desirable upper end of Eagle Avenue, this duplex offers a compelling opportunity in one of Key West's most sought-after residential neighborhoods. The main house is a full renov...

Property Details

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