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Handpicked Homes

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For Sale 1006 Seminary Street

1006 Seminary Street, Key West, FL 33040

$2,695,000

3 Beds
4 Baths
3,049 Sq.Ft.

Property description

MOTIVATED SELLERS offering possible Seller Financing....Reduced again! NEW PRICE: This exceptional turnkey three-bedroom, three bath and one half-bath residence is located in the prestigious Casa M...

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 Open House: 4/4/2026, 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 1317 Newton Street

1317 Newton Street, Key West, FL 33040

$1,175,000

2 Beds
3 Baths
1,386 Sq.Ft.

Property description

Charming 2BD/2.5BA Key West cottage nestled in the sought-after Meadows neighborhood. Recently refreshed inside and out, this home features newer stainless steel appliances, granite countertops in ...

Property Details
For Sale 3704 Eagle Avenue

3704 Eagle Avenue, Key West, FL 33040

$999,000

2 Beds
2 Baths
1,729 Sq.Ft.

Property description

This expansive 6,000 sq. ft. gated property is ideally positioned on a prestigious stretch of Eagle Avenue in the highly sought-after New Town neighborhood.The second floor features a spacious one-...

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

Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this prop...

Property Details
For Sale Open House: 4/4/2026, 1:00 PM - 3:00 PM 1008 Fleming Street

1006-1008 Fleming Street, Key West, FL 33040

$4,795,000

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 Open House: 4/4/2026, 1:00 PM - 3:00 PM 1113 Stump Lane

1113 Stump Lane, Key West, FL 33040

$4,450,000

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 719 Washington Street

719 Washington Street, Key West, FL 33040

$6,295,000

4 Beds
5 Baths
3,150 Sq.Ft.

Property description

Luxury Estate -- A Masterpiece of Light, Space & DesignA new benchmark for modern island living is rising in the coveted Casa Marina district, with completion set for March 2026. Crafted by renowne...

Property Details
For Sale 1513 Pine Street

1513 Pine Street, Key West, FL 33040

$1,899,000

2 Beds
3 Baths
1,717 Sq.Ft.

Property description

Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully crafted Key West home offers exceptional design, privacy, and outdoor living. Built new in 2008 with top-of...

Property Details
For Sale 1616 Atlantic Boulevard Unit: 3

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

$1,524,000

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 3 Nassau Lane Unit: A

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

$825,000

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 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
Active Under Contract 720-726 Emma Street

720-726 Emma Street, Key West, FL 33040

$1,599,000

8 Beds
10 Baths
2,432 Sq.Ft.

Property description

Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currentl...

Property Details
For Sale Open House: 4/4/2026, 10:00 AM - 12:00 PM 1706 Seminary Street

1706 Seminary Street, Key West, FL 33040

$2,149,000

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
Active Under Contract 419 Simonton Street Unit: A

419 Simonton Street Unit: A, Key West, FL 33040

$1,375,000

2 Beds
3 Baths
1,123 Sq.Ft.

Property description

The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West--authen...

Property Details
For Sale 3922 Gordon Road

3922 Gordon Road, Big Pine Key, FL 33043

$850,000

2 Beds
2 Baths
1,040 Sq.Ft.

Property description

Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordon Road is an elevated 2BR/2BA waterfront retreat in Big Pine Key offering the lifestyle buyers come here fo...

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
Active Under Contract 412 Frances Street

412 Frances Street, Key West, FL 33040

$10,500,000

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 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

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