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Handpicked Homes

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For Sale 1311 Grinnell Street

1311 Grinnell Street, Key West, FL 33040

$4,250,000

5 Beds
7 Baths
2,681 Sq.Ft.

Property description

Historic Casa Marina Gem - Fully Restored & Furnished! Experience timeless Key West charm blended with modern luxury in this stunning, fully restored historic home in the highly sought-after Casa M...

Property Details
For Sale 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 1221 20Th Street

1221 20Th Street, Key West, FL 33040

$1,199,000

3 Beds
2 Baths
1,826 Sq.Ft.

Property description

This spacious 3-bedroom, 2-bathroom home is ideal for entertaining and perfectly suited for large family gatherings. Nestled on an oversized, fully fenced corner lot, this tropical oasis features a...

Property Details
Active Under Contract 506 Emma Street

506 Emma Street, Key West, FL 33040

$2,499,000

3 Beds
3 Baths
1,608 Sq.Ft.

Property description

Luxury townhome situated in the prestigious community of Truman Annex. Very well appointed floor plan featuring 3 generous size bedrooms each with ensuite full bathrooms. Enjoy a gorgeous custom ki...

Property Details
For Sale Open House: 2/15/2026, 12:00 PM - 3:00 PM 1014 Flagler Avenue

1014 Flagler Avenue, Key West, FL 33040

$6,495,000

3 Beds
4 Baths
3,104 Sq.Ft.

Property description

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-win...

Property Details
Active Under Contract 1316 Petronia Street

1316 Petronia Street, Key West, FL 33040

$1,100,000

2 Beds
2 Baths
1,222 Sq.Ft.

Property description

Set in a terrific location, this home is full of potential for those with vision. While the property requires renovation, it offers the chance to transform it into a beautiful, personalized space i...

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 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 Open House: 2/15/2026, 1:00 PM - 3:00 PM 901 Johnson Street

901 Johnson Street, Key West, FL 33040

$2,950,000

3 Beds
4 Baths
2,507 Sq.Ft.

Property description

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...

Property Details
For Sale 1006 Seminary Street

1006 Seminary Street, Key West, FL 33040

$2,985,000

3 Beds
4 Baths
3,049 Sq.Ft.

Property description

This exceptional turnkey three-bedroom, three bath and one half-bath residence is located in the prestigious Casa Marina neighborhood, one of Key West's most sought-after enclaves. Showcasing timel...

Property Details
For Sale Open House: 2/15/2026, 12:00 PM - 2:00 PM 1310 Atlantic Drive

1310 Atlantic Drive, Key West, FL 33040

$1,950,000

3 Beds
3 Baths
1,672 Sq.Ft.

Property description

''A turnkey retreat designed for comfort, connection, and carefree living just minutes from the beach.''Discover serenity in this elevated 3-bedroom, 3-bath Key West retreat, built in 2013, includi...

Property Details
For Sale 1124 Catherine Street Unit: 201

1124 Catherine Street Unit: 201, Key West, FL 33040

$440,000

1 Bed
1 Bath
454 Sq.Ft.

Property description

Charming 1-bedroom, 1-bathroom condo offering 454 square feet of living space. The condo boasts an open floor plan with hurricanes rated windows, one assigned parking spot and also located in the X...

Property Details
For Sale 1124 Catherine Street Unit: 202

1124 Catherine Street Unit: 202, Key West, FL 33040

$639,000

2 Beds
1 Bath
677 Sq.Ft.

Property description

This bright and well-maintained condo offers the perfect blend of comfort and convenience in one of Key West's most desirable neighborhoods. Just a straight shot down the road to White Street Pier,...

Property Details
For Sale 1200 White Street

1200 White Street, Key West, FL 33040

$779,000

1 Bath

Property description

Newly formed commercial condo now available for sale on White Street in X Flood Zone! This 1,169sf 1st floor corner unit has been extensively updated and renovated with hurricane rated impact windo...

Property Details
For Sale 1202 White Street

1202 White Street, Key West, FL 33040

$689,000

1 Bath

Property description

Prime commercial space available with 892sf centrally located in Old Town. Unit has hurricane rated windows and doors, features one assigned parking spot and is located in the X Flood Zone. Tenant ...

Property Details
For Sale 1206 White Street

1206 White Street, Key West, FL 33040

$799,999

1 Bath

Property description

Prime commercial space available with over 1,300 sq. ft. centrally located in Old Town. Unit is an end unit and has hurricane rated windows and doors, features one assigned parking spot and is loca...

Property Details
For Sale 201 Coppitt Road Unit: 201A

201 Coppitt Road Unit: 201A, Big Coppitt, FL 33040

$350,000

1 Bed
1 Bath
536 Sq.Ft.

Property description

Enjoy gorgeous sunset views from this waterfront condo on Big Coppitt Key, just 10 minutes from downtown Key West. Perfectly positioned, this 2nd floor end-unit features extra windows and 180 degre...

Property Details
For Sale 906 Johnson Street

906 Johnson Street, Key West, FL 33040

$5,750,000

6 Beds
6 Baths
3,751 Sq.Ft.

Property description

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front...

Property Details
For Sale Open House: 2/15/2026, 12:00 PM - 2:00 PM 101 Front Street Unit: 23

101 Front Street Unit: 23, Key West, FL 33040

$1,875,000

2 Beds
3 Baths
1,216 Sq.Ft.

Property description

Completely renovated and move-in ready, The Foundry #23 in Key West's exclusive Truman Annex is a rare gem that blends historic charm with modern luxury. This beautifully updated townhome features ...

Property Details
For Sale Open House: 2/15/2026, 1:00 PM - 3:00 PM 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 Open House: 2/15/2026, 1:00 PM - 3:00 PM 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

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