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Handpicked Homes

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For Sale 1008 Fleming Street

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 1014 Truman Avenue Unit: 3

1014 Truman Avenue Unit: 3, Key West, FL 33040

$799,900

2 Beds
2 Baths
1,017 Sq.Ft.

Property description

1014 Truman Avenue - Modern Island Elegance in the Heart of Key WestWelcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath condo...

Property Details
For Sale 1028-1030 Truman Avenue

1028-1030 Truman Avenue, Key West, FL 33040

$2,250,000

4 Beds
8 Baths
4,013 Sq.Ft.

Property description

Prime Mixed-Use Investment Opportunity in Key West!Built in 2021 to current building codes, this exceptional four-unit commercial and residential compound is a rare find in the heart of Key West. A...

Property Details
For Sale 1114 Grinnell Street

1114 Grinnell Street, Key West, FL 33040

$3,499,000

5 Beds
4 Baths
2,349 Sq.Ft.

Property description

Exquisite Old Town residence just completed!Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. This historic structure has been reb...

Property Details
For Sale 1124 Catherine Street Unit: 201

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

$479,000

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

$679,000

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 1200-1206 White Street

1200-1206 White Street, Key West, FL 33040

$3,325,000

3 Beds
6 Baths
5,988.09 Sq.Ft.

Property description

New condo conversion! A rare investment opportunity to own a commercial mixed-use strip center located in the heart of Old Town Key West. Property consists of 4 newly converted commercial condo uni...

Property Details
For Sale 1200 White Street

1200 White Street, Key West, FL 33040

$810,000

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

$755,000

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

$855,000

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 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
Active Under Contract 1515 Patricia Street

1515 Patricia Street, Key West, FL 33040

$1,325,000

4 Beds
2 Baths
1,927 Sq.Ft.

Property description

Located in the heart of Midtown Key West, this beautifully renovated 4-bedroom, 2-bathroom home offers over 1,900 sq. ft. of stylish living space on a spacious 6,400+ sq. ft. lot. Recently updated ...

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 Open House: 10/26/2025, 1:00 PM - 3:00 PM 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 3841 N Roosevelt Blvd, #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 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 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 905 Grinnell Street

905 Grinnell Street, Key West, FL 33040

$2,095,000

8 Beds
4 Baths
3,383 Sq.Ft.

Property description

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 bui...

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 3930 S 3930 Roosevelt Boulevard Unit: N302

3930 S 3930 Roosevelt Boulevard Unit: N302, Key West, FL 33040

$584,000

3 Beds
2 Baths
1,075 Sq.Ft.

Property description

Welcome to Las Salinas, where island living meets investment potential. This 3-bedroom, 2-bath condo offers one of the best oversized, covered parking spots in the complex (fits 2 mid-sized cars)--...

Property Details

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