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1022 Fleming St, Key West
$1,600,000
4 Beds ⋅ 2 Baths ⋅ 616423 MLS
Invest in Key West with this legal Duplex which can be easily converted to a single family home! Step into a piece of Key West history with this light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit. Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit is currently rented. It boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

1022 Fleming St, Key West
923 Eaton St, Key West
$1,600,000
3 Beds ⋅ 2 Baths ⋅ 611879 MLS
Price just reduced—arguably the best value in Old Town. Welcome to 923 Eaton Street, where Old Town charm meets laid-back island living. Just steps from the Historic Seaport and a short stroll to Duval, this beautifully updated home blends classic Key West architecture with modern comfort—and you can walk everywhere. Inside, original Dade County Pine, hardwood floors, and a renovated kitchen and baths bring warmth and style. Upstairs, two bright bedrooms offer a peaceful retreat, while a first-floor bunk room adds flexible space for guests. But the real surprise is out back: a lush, deep lot that feels like your own private resort. With tropical landscaping, a 10x20 heated saltwater pool, outdoor shower, lounge area with a mounted TV, and total privacy, the backyard is unexpectedly peaceful—especially for a location just steps from the Seaport and Duval. Tucked away at the rear of the lot is a large, newer shed—hidden from view but incredibly practical. Perfect for bikes, beach gear, or anything you want kept secure while you're away. The home is move-in ready with a newer metal roof, ductless AC, impact-rated sliding doors. Offered fully furnished and turn-key, this is an ideal full-time residence, second home, or income-producing property—ready to sell and ready to enjoy. At this new price, it won't last.

923 Eaton St, Key West
1525 Von Phister St, Key West
$1,600,000
3 Beds ⋅ 2 Baths ⋅ 616833 MLS
Elevated, fully renovated and perfectly located on one of Key West's most idyllic streets, 1525 Von Phister is a beautiful 3BD/2BA modern single level home, designed to impress today's sophisticated buyer. Easy proximity to multiple beaches, restaurants and Key West attractions this highly desirable midtown location is an excellent family friendly neighborhood that offers a wide tree lined street and quiet Key West Living. Completely remodeled in 2015 with new impact windows throughout and single panel disappearing sliding glass doors in both the master suite and kitchen. Spacious rear porch accessible from the kitchen and master suite overlook the private sun-filled oasis with tall mature landscaping offering excellent privacy and security. The exterior rear porch is one of the homes best features. First and foremost, it overlooks the 30ft. lap pool while offering plenty of room for hosting family and friends in the warm winter evenings and provides excellent shade for those who want sun protection. Large oversized master suite with double closets, luxury master bath finished with new cabinets, quartz stone, large soaking tub, separate shower, linen closet and double vanities will not disappoint. Cathedral ceilings and multiple windows with custom electric blinds allow multiple views to the tropical plants and garden. Kitchen is well appointed with plenty of prep space for the family chef with additional breakfast bar that also can serve as an office area. Modern stainless steel appliances, quality cabinetry and a stunning large window above the sink. Lots of space outside with a covered carport for two off street vehicles and additional room for bikes and storage. Completely fenced in with electric gates so you can easily secure your house and vehicles while traveling off the Island. Being Sold Furnished and Turnkey to further ease the move-in transition.

1525 Von Phister St, Key West
626 Margaret St, Key West
$1,590,000
3 Beds ⋅ 2 Baths ⋅ 616780 MLS
Welcome to this captivating historic Conch home, where the essence of Key West island luxury comes alive. This charming residence boasts a classic front porch that beckons you to sit back and enjoy the tropical breeze, making it an ideal space for leisurely mornings or cozy evenings. Upon entering, you are greeted by a sun-drenched interior adorned with Dade County pine hardwood flooring and high ceilings that create an inviting and spacious atmosphere, perfect for both relaxation and entertaining. The heart of this home lies in its kitchen, a culinary haven equipped with stainless steel appliances, 6 burner Viking stove top, pantry space, and a comfortable seating area. The open design allows for seamless flow from the kitchen to the back patio, making it effortless to host gatherings or enjoy quiet family meals by the pool. Step outside to discover a relaxing pool area, complete with an air-conditioned poolside guest cabana. This versatile space features a wet bar and a cozy seating area that easily transforms into a pull-out sofa bed, ideal for hosting friends and family or enjoying a peaceful afternoon by the pool. Ascend to the second floor to find a striking stained glass window that adds a touch of elegance to your arrival. Here, you'll discover a generous master suite, boasting cathedral ceilings and an abundance of closet space, creating a serene retreat. Additionally, a bonus room is currently set up as a home office, providing flexibility for your lifestyle needs. A delightful guest bedroom completes this level, featuring access to a private rooftop terrace that overlooks the inviting pool, perfect for unwinding at sunset or enjoying morning coffee in solitude. This historic Conch home is not just a residence; it is a lifestyle, offering a harmonious blend of modern conveniences and timeless charm. With its ideal location, you are just moments away from all that Key West has to offer—vibrant nightlife, exquisite dining, and stunning beaches.

626 Margaret St, Key West
7 Mccoy Cir Unit # 7, Key West
$1,568,750
2 Beds ⋅ 3 Baths ⋅ 619839 MLS
New Listing! Discover a stunning waterfront home in Key West, complete with covered parking and a boat slip. This idyllic island retreat is situated in the heart of Key West, and it boasts breathtaking Gulf views. This elevated home at Flagler's Landing is offered furnished-just bring your boat and clothes. You can enjoy waterfront vistas from both your living area and bedrooms. The main living floor features an expansive open floor plan, which includes a dining area, a powder room, and sliding doors that lead to a generously sized private balcony. The kitchen is equipped with stainless steel appliances and a breakfast bar for casual dining. The primary suite includes a walk-in closet and an en suite bath with a double vanity, as well as a bonus closet and picturesque water views. The second bedroom also offers beautiful water views and comes with its own en suite bath. The upper landing provides space for a home office desk or a cozy reading nook with access to a balcony. The laundry facilities are conveniently located on the bedroom level. There is central air conditioning throughout the home. It includes covered parking and a patio area, along with the 24' boat slip for your nautical adventures. POOL!

7 Mccoy Cir Unit # 7, Key West
404 Porter Ln Unit 16, Key West
$1,565,000
2 Beds ⋅ 2 Baths ⋅ 617424 MLS
404 Porter Lane is located in the sought after Porter Court community where properties rarely come on the market. Duval, shops and restaurants are only a short stroll away. This corner unit is flooded with natural light from windows on three sides. It features private front and rear porches plus a separate gate to the deeded parking. A cathedral ceiling and tall windows in the living room opens the space to the outdoors and views of tropical foliage. This stunning home is being sold fully furnished with the high end custom furnishings that create a sophisticated yet relaxed island atmosphere. The dining room is adjacent to the upgraded kitchen with stainless appliances and a breakfast bar. A first floor bedroom with adjoining bath is perfect for guests or as a first floor primary. A pantry and storage closet is also on the first floor. The large primary suite encompasses the entire second floor and offers complete privacy. The walk in closet has custom built-ins for added convenience. The primary bath has double vanities and a large shower. The attic has been insulated and finished into usable storage space with pull down stairs for easy access. All the doors and windows were recently replaced and upgraded to hurricane rated. Porter Court is an enclave of only 19 units. It features a large pool and hot tub/spa in the center of the courtyard. Dues include flood and windstorm insurance, landscaping, maintenance, cable and internet. This home is in immaculate, move in condition and being sold furnished. Just move in and enjoy your life in Key West.

404 Porter Ln Unit 16, Key West
3405 16th, Key West
$1,550,000
3 Beds ⋅ 3 Baths ⋅ 621303 MLS
A private Key West retreat designed for easy indoor-outdoor living. This stylish 3-bedroom, 2.5-bath home offers a relaxed tropical setting with generous living spaces that open effortlessly to the pool and expansive patio. The oversized lot creates a true sense of privacy, with multiple areas for lounging, dining and entertaining beneath the palms and tiki-covered spaces. A 14' x 28' pool anchors the backyard, while thoughtful updates, a metal roof, outdoor shower and abundant parking add everyday functionality. Conveniently located in New Town, this home captures the laid-back Keys lifestyle with space to unwind, entertain and enjoy island living at its best.

3405 16th, Key West
1030 Sandys Way, Key West
$1,550,000
4 Beds ⋅ 3 Baths ⋅ 620042 MLS
Tucked behind the gates of the exclusive Marquesa Court, an intimate enclave of just nine private residences, this exceptional home offers privacy, security, and a central Key West location that places you moments from everything the island has to offer. Built in 2006 above flood elevation and thoughtfully constructed with impact-rated doors and windows, this well-designed residence combines peace of mind with timeless comfort. The spacious floor plan features 4 bedrooms and 3 full bathrooms, offering flexibility for full-time living, a second home, or hosting family and guests. The oversized primary suite is a true retreat, complete with a generous spa-inspired bath featuring a jacuzzi tub, separate shower, private water closet, and direct access to the upstairs balcony overlooking the pool and the tranquil backdrop of the adjacent nature preserve. The first-floor fourth bedroom offers excellent versatility--ideal as a guest suite, home office, or den. What truly sets this property apart is the rare combination of privacy, gated exclusivity, and natural serenity, creating a peaceful residential feel while remaining centrally located in Key West. A wonderful opportunity for the next owner to enjoy island living in one of Key West's most desirable hidden neighborhoods.

1030 Sandys Way, Key West
1311 Pine St, Key West
$1,550,000
3 Beds ⋅ 3 Baths ⋅ 617223 MLS
Tucked away on one of The Meadows most charming and secluded streets, this storybook Key West cottage offers the perfect blend of island character and modern comfort. Featuring three bedrooms and two and a half baths, the flexible layout includes an expansive upstairs primary suite, a first-floor bedroom with an en suite bath, and a third bedroom with a convenient half bath — perfect for guests or a home office. Sunlight filters through vaulted ceilings and bright, open living spaces, while the updated kitchen and dining area provide the ideal setting for entertaining. Step outside to enjoy the newly landscaped backyard complete with a private pool, spa, and whimsical outdoor shower — a tranquil retreat surrounded by lush tropical greenery. Relax on the inviting front porch and take in the neighborhood's quiet charm, all while being just minutes from the island's best dining, galleries, and attractions. Offered fully furnished, this home is move-in ready and captures the essence of casual Key West living in an X-Zone location.

1311 Pine St, Key West
115 Front St Unit 301, Key West
$1,550,000
2 Beds ⋅ 2 Baths ⋅ 617119 MLS
Third floor Harbour Place condominium in the historic Navy Administration building featuring high ceilings and large windows. Enter your private foyer where you have a full bath and a guest bedroom. Large living and dining areas overlook Truman's Little White House. The primary bedroom is just down the hall and has its own private balcony overlooking the entrance to the building and Truman's Little White House. It has one covered parking space #92. Includes a non-transient rental license.

115 Front St Unit 301, Key West
1223 Flagler Ave, Key West
$1,550,000
4 Beds ⋅ 3 Baths ⋅ 616436 MLS
Discover your own private oasis in the heart of Key West! This spacious 4BR/3BA two-story home offers over 2,200 sq ft of living space designed for both relaxation and entertaining. Located in desirable Midtown, just minutes from the Casa Marina, Higgs Beach, and White Street Pier, you'll enjoy the perfect balance of island living and everyday convenience. Step inside to find an open floor plan with multiple living and dining areas, a modern kitchen with stainless steel appliances and wine cooler, and flexible spaces ideal for guests or family. The home's layout includes two bedrooms on each level, providing privacy and options for hosting or working from home. Outside, the resort-style backyard is the true highlight: a heated pool with expansive deck, surrounded by lush tropical landscaping and tall privacy fencing. Enjoy the covered lanai for dining al fresco, rinse off in the outdoor shower after a day at the beach, or simply unwind in the shade of palm trees. This fully fenced property is perfect for both peaceful relaxation and lively gatherings. Additional features include off-street parking for 2-3 vehicles, central air, laundry room, ceiling fans, and negotiable furnishings. With a 30-day minimum rental allowance, this property also offers excellent potential as a vacation rental or investment. Whether you're seeking a year-round residence, second home, or income-producing property, 1223 Flagler Avenue delivers the best of Key West living with comfort, charm, and convenience.

1223 Flagler Ave, Key West
604 Whitehead St, Key West
$1,500,000
2 Baths ⋅ 618495 MLS
Prime standalone commercial opportunity in the heart of Old Town Key West! Located near high-traffic corner of Whitehead Street and Southard Street, this turnkey building is currently operating as office space and offers outstanding visibility plus ample off-street parking. The flexible layout includes two conference rooms, four private offices, a built-in reception desk, full bath + half bath, kitchen, kitchenette, and an outdoor patio and several entrances. Corner location, strong street presence, and a highly functional interior make this a rare chance to secure a standalone commercial property in one of Key West's most active corridors. A perfect blend of exposure, convenience, and versatility. Zoned HRO (Historic Residential/Office) and located in the X Flood Zone.

604 Whitehead St, Key West
928 Truman Ave Unit 101, Key West
$1,500,000
8 Beds ⋅ 5 Baths ⋅ 613024 MLS
Old Town Multi-Use Property Located on Truman Avenue, this versatile property offers both reliable income and future potential. Currently comprised of five legal long-term rental apartments, it's an excellent option for investors seeking steady cash flow or employee housing. Unit 101, a CBS structure, also offers potential for commercial conversion (buyer to verify), while the remaining apartments continue generating income. Property Highlights: 8 Bedrooms / 5 Bathrooms $11,650 Monthly Rental Income Net Income: $112,461.46 (includes management fees) 7.12% Cap Rate at $1.58M Located in an X Flood Zone This is currently the lowest-priced multi-unit property in Old Town with 5 legal units in an X flood zone, making it a standout opportunity. Blend dependable rental income with strong investment returns.

928 Truman Ave Unit 101, Key West
1217 Petronia St, Key West
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 617743 MLS
A Classic Key West Winter Retreat in the Heart of the Meadows. Tucked away on one of the quiet, one way streets of the historic Meadows, this elevated Key West home offers a rare opportunity to enjoy Old Town living as it was meant to be - charming, neighborly and removed from the bustle of tourism, yet moments from everything that makes the Island special. Built entirely of original Dade County Pine, the home exudes warmth and craftsmanship, with rich hardwood floors and timeless architectural details throughout. The main residence features two comfortable bedrooms and two and a half baths designed for relaxed living and easy entertaining. A charming sleeping loft provides flexible space for visiting family or grandchildren, with reading nooks and an office space. Outdoors, a separate pool house sits adjacent to the refreshing dipping pool, creating the perfect ambiance for quiet afternoons, morning swims or evening cocktails under the Island sky. Thoughtful storage and off street parking add convenience rarely found in Old Town. The Meadows is beloved for it's sense of community - a neighborhood where neighbors know one another, streets invite evening strolls and island life unfolds at an unhurried pace. Elevated, secure and full of character, this home is ideal for those seeking a lock and leave winter residence that blends history, comfort and the authentic spirit of Key West. A place to slow down, settle in and make winter feel like home.

1217 Petronia St, Key West
613 Olivia St, Key West
$1,500,000
4 Beds ⋅ 2 Baths ⋅ 617260 MLS
Welcome to 613 Olivia Street in the Heart of Old Town Key West! This historic residence just might be one the oldest standing homes in all of Key West. The current owner has occupied this home for several decades and is now willing to let a new owner take over the care of this historic property. Ready for your vision, this home is located in the X-Flood Zone and awaits restoration to its full potential. Ideally located within walking distance of all that Key West has to offer, yet far enough away to enjoy peace and quiet. Currently set up as a four (4) bedroom and one and half (1.5) bathrooms, with 1,680 sq ft of living space. Walk right into your ground floor living room, kitchen, two bedrooms and one full bathroom. On the second floor are two guest bedrooms and a half bathroom. Step out back to a spacious Old Town, Key West yard, that is ready for you to bring your own design vision to life. This truly one-of-a-kind property is filled with more history and charm than you can count. Make it your own and impress neighbors and visitors alike with your personal touches and design vision. Call today for a private showing!

613 Olivia St, Key West
3735 Eagle Ave, Key West
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 618137 MLS
BRAND NEW LISTING! Introducing a prestigious corner lot on Eagle Avenue. This Mediterranean-style home is a true gem located in the heart of Key West. The home features a sun-drenched foyer that welcomes you into a spacious living area. The updated kitchen showcases Taj Mahal Quartzite countertops and custom cabinetry. Home offers three generous bedrooms and three bathrooms. The private primary suite overlooks the pool area and includes dual bathrooms for effortless morning routines. Outdoor spaces are ideal for al fresco dining by the pool or relaxing on the lanai. There's also a bonus space that is perfect for a home office, art studio, or gym. This home comes furnished and turnkey, making your move to paradise seamless. The property features a beautifully landscaped tropical fenced yard with outdoor lighting, a garage for convenient off-street parking and storage, outdoor shower, central AC. Located just minutes from beaches, parks, the airport, and Old Town Key West.

3735 Eagle Ave, Key West
1409 Olivia St, Key West
$1,469,500
2 Beds ⋅ 3 Baths ⋅ 618492 MLS
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 Dennis Beebe, this 2-bedroom, 2.5-bath residence in the coveted Meadows neighborhood represents the pinnacle of quality-driven restoration. Every surface tells a story of craftsmanship: rounded wall finishes and extensive trim work create flowing visual warmth, while reclaimed Dade County pine adorns feature walls and a restored captain's ladder. Heart pine flooring anchors the living spaces, complemented by custom hardwood doors and complete plantation shutters throughout. Cathedral ceilings amplify the home's embracing character, enhanced by a thoughtfully curated lighting package that transforms ambiance at will. Surprise elements throughout add to its charm: seaglass gate knobs, koi fish porch lights flanking a transom-topped entry with historic corbels, hidden medicine cabinets, and extensive built-ins with locking storage. Both the primary suite and kitchen open through double doors to a private back deck with hot tub, while a generous walk-in closet with aromatic cedar lining provides luxurious storage. Kohler fixtures, granite countertops, stainless appliances, and central air provide contemporary comfort. Professional landscaping with automatic irrigation and timed lighting creates an immersive tropical sanctuary behind reclaimed brick pathways. The property driveway accommodates a Jeep, golf cart, or Mini Cooper, while dual-layer hurricane protection (teak shutters plus Kevlar backing) ensures peace of mind. Three structural piers provide added stability. Fully furnished, freshly painted, and permitted for 28-day+ rentals in HMDR zoning, this is more than restoration, it's a masterclass in doing it right!

1409 Olivia St, Key West
no property photo
$1,450,000
2 Baths ⋅ 619788 MLS
For Statistical Purposes Only

316 Petronia St, Key West
1332 Duncan St, Key West
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 614522 MLS
This one-of-a-kind Conch house effortlessly blends island charm with modern sophistication. Featuring three spacious bedrooms and four luxurious bathrooms, the home boasts stunning wall-to-wall Dade County pine that adds character and warmth throughout. The open floor plan is ideal for both entertaining and everyday living, seamlessly connecting the living area to a chef-inspired kitchen. The kitchen is a culinary dream, with sleek quartz countertops, top-of-the-line stainless steel appliances, and ample space for creating gourmet meals. Just beyond the kitchen, step into a private outdoor oasis. Surrounded by lush, mature landscaping and beautiful brick pathways, the serene courtyard leads to an oversized heated pool - perfect for a relaxing dip or enjoying the tranquil surroundings. Located just steps from Key West's vibrant dining, art galleries, and historic landmarks, this home offers the best of both seclusion and convenience. A truly special retreat that invites you to experience island living at its finest.

1332 Duncan St, Key West
2800 Staples Ave, Key West
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 616662 MLS
Discover a rare opportunity to own a stunning property in one of Key West's most desirable neighborhoods. Nestled on a spacious corner lot, 2800 Staples Avenue blends modern comfort with tropical charm. This beautifully renovated home offers 4 bedrooms and 3.5 bathrooms with an open-concept floor plan ideal for entertaining or relaxing in paradise. Bright, airy living spaces showcase vaulted ceilings and a chef's kitchen with stainless appliances, quartz countertops, wine cooler, and large island. Enjoy your spacious primary suite with a sleek ensuite bath featuring a soaking tub, separate shower, and dual vanity. The split floor plan provides privacy for guests or family. Step outside to your private oasis with lush landscaping, a sparkling new pool, and ample space for outdoor dining and lounging. The covered porch invites you to savor island breezes, while the fully fenced yard ensures privacy and tranquility. Additional features include ample storage, impact windows and doors, and close proximity to schools, parks, shopping, and dining. Minutes from Key West's historic Old Town and world-famous beaches, this home delivers the ultimate island lifestyle. Don't miss this Key West gem—schedule your private showing today. Furniture in photos is virtually staged.

2800 Staples Ave, Key West
1616 Atlantic Blvd Unit 3, Key West
$1,450,000
2 Beds ⋅ 3 Baths ⋅ 618157 MLS
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 deliver a truly coastal lifestyle. Set within the exclusive, gated oceanfront enclave of Casa Caselles, this solid concrete home has been meticulously renovated with a focus on timeless materials and modern convenience. Mahogany staircases anchor the interior with warmth and craftsmanship, while electric blinds, smart TVs, and a full security system bring effortless, lock and leave peace of mind. The kitchen and living spaces are both beautiful and functional, featuring LG ThinQ appliances and a layout designed for everyday ease and entertaining alike. Impact doors and windows enhance durability and storm protection, while walk in closets provide storage rarely found in townhomes of this size. With 2 bedrooms, 2.5 baths, and 1,940 square feet of interior living space, the home flows naturally across multiple levels, complemented by outdoor areas that capture ocean breezes and sunrises. With no rentals allowed, Casa Caselles feels more like a private retreat than a condominium, and opportunities to purchase a renovated, fully furnished residence of this caliber are exceptionally rare. If you are looking for the best, the search stops here.

1616 Atlantic Blvd Unit 3, Key West
1033 Catherine St, Key West
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 618868 MLS
STATISTICAL PURPOSES ONLY

1033 Catherine St, Key West
1305 Elizabeth St, Key West
$1,442,400
2 Beds ⋅ 2 Baths ⋅ 617771 MLS
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 footprint or add an additional pool side cottage. An open floor plan welcomes you through French doors to this delightful cottage. Enjoy high ceilings, wood floors with 2 bedrooms and 2 full bathrooms. The primary suite enjoys a sweet front porch perfect for relaxing. This property is situated on very edge of Old Town that nestles up to the Casa Marina area and is just a couple of blocks to the quieter end of famous Duval Street.

1305 Elizabeth St, Key West
1421 Reynolds St, Key West
$1,429,821
4 Beds ⋅ 3 Baths ⋅ 619646 MLS
1421 Reynolds is a beautifully renovated mid century modern home located 3 blocks from Higgs Beach, one of Key West's best beaches and the perfect spot to watch the sunset. You will see the ocean from your driveway. You can walk or bike to Duval street, but live just far enough away to enjoy peace and tranquility. The spacious floor plan offers 4 bedrooms and 3 bathrooms. Vaulted ceilings throughout give it a sense of open space and the sliding glass doors in the great room open all the way for indoor outdoor living. All impact doors and windows allow lots of natural light to flood into the modern renovation in every room. Off street parking and room for a pool make this a rare opportunity in one of Key West's most coveted neighborhoods, the Casa Marina. In the front you will find a private zen garden adding outdoor space to the master bedroom. The kitchen has all stainless appliances with Viking, Samsung smart fridge and JennAir. This home was designed to enjoy the best Key West has to offer, from the interior to the outdoor space to the neighborhood itself. You will find yourself swimming in the ocean for sunset, walking to the Casa Marina Hotel for drinks overlooking the ocean, and having dinner on the beach at Salute's or Louie's Backyard. Owner/listing agent is a licensed FL Real Estate Broker.

1421 Reynolds St, Key West
1119 Simonton St Unit A1 & A2 & C1, Key West
$1,425,000
2 Beds ⋅ 2 Baths ⋅ 619049 MLS
Charming Old Town Duplex located in the heart of old town. Ideally located on Simonton Street this charming duplex places you just steps from Duval Street, along with world-class dining, boutique shopping, beaches, and neighborhood parks. This versatile property is the perfect Key West residence, second home, or income-producing investment. Live in one side and rent the other, or maximize its potential as a full rental property. The home welcomes you with a classic front porch and a private, fenced courtyard surrounded by tropical landscaping--complete with a relaxing hot tub, ideal for enjoying the Key West lifestyle. Inside, the property features updated kitchens, ductless A/C units, and an in-unit washer and dryer. Additional highlights include off-street parking and X Flood Zone. An additional lot (C-1) is included in the sale, featuring a converted storage for added flexibility. Whether you're looking for an island retreat or an investment opportunity in one of Key West's most desirable locations, this Simonton Street property captures the essence of Old Town living. Also available to be purchased separately as two half duplexes. See MLS #619050 and #619052

1119 Simonton St Unit A1 & A2 & C1, Key West
1413 Olivia St, Key West
$1,410,000
3 Beds ⋅ 2 Baths ⋅ 614503 MLS
Stunning and impeccably maintained, this 3 bed, 2 bath Conch home in the highly sought-after Meadows neighborhood seamlessly blends historic charm with modern luxury. The custom-designed kitchen is a chef's dream, featuring new quartz countertops, sleek backsplash, remodeled cabinetry, and stainless steel appliances. Rich Brazilian hardwood floors run throughout, and a powerful 17.5kW Generac generator ensures uninterrupted comfort. Inside, soaring ceilings and an open-concept living space are bathed in natural light from expansive windows. At the rear of the home, you'll find a versatile bonus space perfect for a home office, reading nook, or creative studio. Sold fully furnished with all-new pieces from Royal Furniture, this home offers a true turnkey experience. Step outside onto the durable Trex deck, surrounded by lush, professionally landscaped gardens—your own private tropical retreat. Or relax on the welcoming front porch and soak in the charm of Key West living. The fully fenced yard offers added privacy and peace of mind. Don't miss your chance to own a slice of paradise—call today to schedule your private showing!

1413 Olivia St, Key West
613 Virginia St, Key West
$1,400,000
3 Beds ⋅ 3 Baths ⋅ 616829 MLS
For Statistical Purposes

613 Virginia St, Key West
708 Bakers Ln, Key West
$1,400,000
1 Beds ⋅ 1 Baths ⋅ 618002 MLS
Positioned on a rare 5000 Sq Ft. lot at one of the highest natural elevations on the Island, this property represents an exceptional opportunity in the heart of Old Town Key West - where location is everything. Set beneath a canopy of established trees, the site offers shade, privacy and a sense of timeless Old Town Character that is increasingly hard to find. Currently improved with a livable one-bedroom, one bath residence, the true value lies in the land itself. The existing structure provides flexibility - whether as a holding asset, future redevelopment or new build - allowing the next owner to capitalize on one of the most desirable settings in Key West. A full 10 out of 10 walkability Score, steps from world class dining, renowned live music cafes, galleries and the vibrant cultural fabric that defines the Island Lifestyle. A leisurely four minute walk to Duval St. underscores the property's unmatched proximity while maintaining a quieter, more refined residential feel. Opportunities of this caliber, high elevation, generous size lot, premier walkability and a blue chip location - are exceedingly rare. 708 Bakers Lane is a property for the discerning buyer who recognises that in Key West, land in the right spot is the ultimate luxury investment.

708 Bakers Ln, Key West
514 Margaret St, Key West
$1,400,000
5 Beds ⋅ 4 Baths ⋅ 618128 MLS

514 Margaret St, Key West
515 Petronia St, Key West
$1,400,000
2 Beds ⋅ 2 Baths ⋅ 618308 MLS
Introducing 515 Petronia Street, a rare Old Town offering where refined island living aligns with proven investment fundamentals. Ideally positioned between Simonton and Duval Streets, this 2-bedroom, 2-bath residence places Key West's most iconic dining, shopping, and nightlife just steps away, while maintaining a private, resort-style atmosphere. A gated entry opens to a tranquil poolside courtyard, setting the tone for seamless indoor-outdoor living. French doors connect the living spaces to the outdoors, and each bedroom enjoys access to its own private patio. The kitchen features custom wood cabinetry, granite countertops, & stainless steel appliances including a gas range. Bathrooms are updated with clean, contemporary finishes, dual vanities with vessel sinks, polished chrome fixtures, & discreetly integrated in-unit laundry. The fully enclosed backyard retreat serves as the home's centerpiece, anchored by a recently resurfaced swimming pool, multiple lounge areas, and an expansive covered outdoor bar and entertaining pavilion complete with refrigeration, mounted televisions, and ambient lighting. Mature palms and tropical landscaping provide exceptional privacy and a true resort-style setting. The property benefits from high-quality, low-maintenance improvements, including a 2018 roof with Berridge Victorian metal shingles, Hardie plank siding, and Azek decking. A rare advantage in Old Town, two off-street parking spaces enhance both convenience and long-term desirability. An established professional vacation management program is already in place, offering a seamless transition for buyers seeking immediate income with minimal operational involvement. Whether held as a refined second home, a professionally managed asset, or a strategic blend of both, 515 Petronia Street represents a compelling Old Town acquisition defined by location, scarcity, quality construction, and enduring value.

515 Petronia St, Key West