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Handpicked Homes

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For Sale Single-story home at 34 Key Haven Road with tall palms, a fenced lawn, and a basketball hoop.

34 Key Haven Road, Key Haven, FL 33040

$1,395,000

4 Beds
2 Baths
1,743 Sq.Ft.

Property description

Life on the water feels effortless at 34 Key Haven Road! Set along a wide canal in one of Key Haven's most desirable pockets, this 4 bedroom, 2 bathroom home is designed for those who want to be on...

Property Details
For Sale Two-story corner commercial building with pale yellow siding, a white metal roof, and storefronts.

1200+1202 White Street, Key West, FL 33040

$945,000

1 Bath
2,061 Sq.Ft.

Property description

PRIME COMMERCIAL SPACE - Two combined commercial condos on White Street in X Flood Zone! These 2,061sf 1st floor units have been extensively updated and renovated with hurricane rated impact window...

Property Details
For Sale Building at 1202 White Street with a low storefront and an upper section.

1202 White Street, Key West, FL 33040

$450,000

1 Bath
892.36 Sq.Ft.

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. The mon...

Property Details
For Sale Waterfront condominiums and palm-lined marina with boats docked in the foreground.

3841 N Roosevelt Boulevard 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 Waterfront condominiums and palm-lined marina with boats docked along the shore.

3841 N Roosevelt Boulevard 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
Active Under Contract Palm-lined grassy yard beside a white building, with two boat trailers on the lawn.

3705 Eagle Avenue, Key West, FL 33040

$825,000

Property description

**NOW OFFERING OWNER FINANCING** Build your Key West dream from the ground up! This rare, vacant 6,000sf lot sits on one of the most desirable blocks of Eagle Avenue in New Town - an established, r...

Property Details
For Sale Aerial view of a waterfront neighborhood, with a canal, palm-lined homes, and a vacant parcel.

1151 Sugarloaf Boulevard, Sugarloaf Key, FL 33042

$1,499,000

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 Modern single-story home with a metal roof, palm trees, and a landscaped front yard.

1100 Johnson Street, Key West, FL 33040

$5,200,000

4 Beds
3 Baths
2,058 Sq.Ft.

Property description

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated ...

Property Details
For Sale White house screened by mature trees, with a grassy front yard and gated entrance.

3711 Eagle Avenue, Key West, FL 33040

$825,000

2 Beds
2 Baths
1,464 Sq.Ft.

Property description

Prime redevelopment opportunity in the coveted upper section of Eagle Avenue, now offered with owner financing. This legal duplex is situated on one of the most desirable blocks in Key West, within...

Property Details
For Sale Light blue cottage with navy shutters, a covered porch, white picket fence, and brick driveway.

810 Carey Lane, Key West, FL 33040

$2,150,000

3 Beds
2 Baths
1,200 Sq.Ft.

Property description

Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, ...

Property Details
Pending White house with a lit poolside deck, French doors, and tropical landscaping at dusk.

419 Simonton Street c, Key West, FL 33040

$1,995,000

2 Beds
3 Baths
1,409 Sq.Ft.

Property description

Old Town has plenty of history. What it rarely has is a brand-new secret. Privately positioned behind one of Simonton Street's most storied facades, 419 Simonton Street C is a freestanding 2026 re...

Property Details
For Sale White gabled house with pale green shutters, a covered porch, and illuminated tropical landscaping at dusk.

812 Carsten Lane, Key West, FL 33040

$2,599,000

3 Beds
2 Baths
1,204 Sq.Ft.

Property description

Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. E...

Property Details
For Sale White Key West house with dark shutters, a picket fence, and brick walkway.

1212 Olivia Street, Key West, FL 33040

$2,475,000

3 Beds
2 Baths
1,750 Sq.Ft.

Property description

Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence...

Property Details
For Sale White two-story cottage with a covered porch, turquoise door and shutters, and a white picket fence.

1109 Stump Lane, Key West, FL 33040

$2,199,000

3 Beds
4 Baths
1,724 Sq.Ft.

Property description

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, wh...

Property Details
For Sale Two-story home with a brick lower floor, wooden privacy gate, and lush tropical landscaping.

1503 Atlantic Boulevard, Key West, FL 33040

$1,095,000

4 Beds
5 Baths
2,750 Sq.Ft.

Property description

THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility....

Property Details
For Sale Condo living and dining area with wicker chairs and ocean views through sliding glass doors.

1901 S Roosevelt Boulevard 208E, Key West, FL 33040

$1,349,000

3 Beds
2 Baths
1,395 Sq.Ft.

Property description

Direct ocean views await at this rarely available 3-bedroom, 2-bath condominium in Key West's gated La Brisa community, directly across from Smathers Beach. Whether you're seeking a full-time resid...

Property Details
For Sale House at 723 Eaton Street, with an orange front door, palms, and a white picket fence.

723 Eaton Street, Key West, FL 33040

$6,450,000

7 Beds
9 Baths
3,739 Sq.Ft.

Property description

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West wi...

Property Details
For Sale Modern glass-walled home beside an illuminated pool, framed by palm trees at dusk.

1014 Flagler Avenue, Key West, FL 33040

$4,700,000

3 Beds
4 Baths
3,104 Sq.Ft.

Property description

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot ...

Property Details
For Sale Open-plan kitchen and living room with a wood-topped island, stainless appliances, and a cable-railing staircase.

1014 Truman Avenue 202, Key West, FL 33040

$750,000

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 Aerial view of a palm-lined waterfront home with a swimming pool and landscaped grounds.

3750 Sunrise Lane, Key West, FL 33040

$6,200,000

5 Beds
5 Baths
5,378 Sq.Ft.

Property description

You can renovate a house. You can't recreate the land. At the end of Sunrise Lane, on a 28,500 SF peninsula with water on three sides, sits one of the most compelling residential sites in Key West....

Property Details
For Sale White Street storefront at 1206, with a metal roof and parked cars along the road.

1206 White Street, Key West, FL 33040

$575,000

1 Bath
1,389 Sq.Ft.

Property description

PRIME OPPORTUNITY FOR OWNER/OPERATOR! Commercial condo available with over 1,300 sq. ft. centrally located in Old Town. This is an end unit and has a half bath, hurricane rated windows and doors, f...

Property Details

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