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Handpicked Homes

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Active Under Contract 31129 Avenue G

31129 Avenue G, Big Pine Key, FL 33043

$455,000

3 Beds
3 Baths
844 Sq.Ft.

Property description

MOTIVATED AND PRICED TO SELL. Introducing a charming and beautifully updated home in the heart of Big Pine Key. This three bedroom two and a half bathroom residence offers comfort, privacy, and mod...

Property Details
For Sale 1114 Grinnell Street

1114 Grinnell Street, Key West, FL 33040

$3,399,000

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 1151 Sugarloaf Boulevard

1151 Sugarloaf Boulevard, Sugarloaf Key, FL 33042

$1,649,000

3 Beds
2 Baths
2,144 Sq.Ft.

Property description

Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of...

Property Details
For Sale 1305 Elizabeth Street

1305 Elizabeth Street, Key West, FL 33040

$1,599,000

2 Beds
2 Baths
837 Sq.Ft.

Property description

Charming conch cottage on a generous size lot with refreshing pool and plenty of off street parking! This home is uniquely situated on a corner lot with many possibilities to expand on the footprin...

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 31047 Avenue I

31047 Avenue I, Big Pine Key, FL 33043

$655,000

3 Beds
3 Baths
1,500 Sq.Ft.

Property description

Discover the charm of island living in this beautifully maintained 3-bedroom, 2.5-bath home, ideally situated on a spacious 5,000 sq ft lot in the heart of Big Pine Key. Built in 2007, this elevate...

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 703 Elizabeth Street

703 Elizabeth Street, Key West, FL 33040

$2,299,000

3 Beds
2 Baths
1,404 Sq.Ft.

Property description

Perched at the highest island elevation referred to as Solares Hill you will find this timeless Old Town gem. A perfect blend of style and charm welcome you to an open concept floor plan with cathe...

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 3 Nassau Lane Unit: A

3 Nassau Lane Unit: A, Key West, FL 33040

$925,000

1 Bed
1 Bath
468 Sq.Ft.

Property description

Charming Key West Cottage on Historic Nassau LaneNestled along the picturesque and historic Nassau Lane, this delightful one-bedroom cottage offers a perfect blend of Key West charm and modern comf...

Property Details
For Sale 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 1014 Truman Avenue Unit: 202

1014 Truman Avenue Unit: 202, 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 West Welcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath cond...

Property Details
For Sale Open House: 2/8/2026, 1:00 PM - 3:00 PM 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 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 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 17245 Jamaica Lane

17245 Jamaica Lane, Sugarloaf Key, FL 33042

$825,000

3 Beds
2 Baths
1,248 Sq.Ft.

Property description

Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life--pad...

Property Details
For Sale 816 South Street Unit: 4

816 South Street Unit: 4, Key West, FL 33040

$629,000

1 Bed
1 Bath
640 Sq.Ft.

Property description

Experience the charm of this bright and airy 1-bedroom, 1-bathroom Southpark Condominium located in the prestigious Casa Marina neighborhood. Known for its tranquil atmosphere and prime location, t...

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 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 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

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