Divider
Content Divider

Lower Keys Real Estate for Sale, Homes and Condos in the Florida Keys

Total Listings 655
Order By:

$3,400,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
3 Bed, 3 Baths, 2,295 SqFt Days Listed: 360
-42.86% ($2,550,000) 18 Price Changes : Last Change 57 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Davit Pads25f

Perched on the oceanfront, this extraordinary Cudjoe Key estate boasts breathtaking views from every vantage point, including the rooftop deck. The solid concrete construction, complete with impact-resistant doors and windows, concrete dock, and poolside cabana featuring a bar, sink, and ice machine, ensures a luxurious haven. Lush landscaping, meticulously maintained on a weekly basis, adds to the propertys allure. Upon entering the coded-entry home, a stunning living, dining, and kitchen area unfolds, complete with quartz countertops, stainless steel appliances, and a convenient laundry room. The kitchens center island is spacious and includes refrigerator and freezer drawers, a cooktop and barstools, making it a great entertaining area. The main levels ensuite bedroom, featuring double beds and a jack-and-jill bathroom, offers direct access to the oceanfront patio and a spiral staircase leading down to the pool. Ascend to the master suite, where a lavish bathroom awaits, complete with a jetted tub, double sinks, programmable commode, and walk-in shower, all set against the backdrop of dazzling ocean views. A third ensuite bedroom, features a walk-in shower, single sink, and expansive mirror, with the king-size bed positioned to maximize the stunning vistas. The private outdoor area, complete with a mermaid-adorned pool, large BBQ area, and cabana room, is perfect for outdoor entertaining. World-class fishing and diving opportunities are minutes away, with the Gulf and Atlantic within easy reach. This idyllic location also offers a front-row seat to the marine life of Cudjoe Bay, including porpoise, ospreys, sharks, stingrays, and manatees. Situated in a highly sought-after area of Cudjoe Key, this estate is surrounded by excellent restaurants and boasts wonderful views of the American Shoals Lighthouse.

$3,450,000
Key West
Kamien Plat #2   - MM: 2.00
5 Bed, 5 Baths, 3,081 SqFt Days Listed: 104
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Extraordinary transformation of this luxurious elevated midtown home boasting 5 spacious bedrooms each with stunning designer ensuite baths. Originally built in 1997 with a full scale ground up renovation completed in 2024, this home boasts the gorgeous custom details at every turn. The elevated main floor of the home features an open floor plan and wet bar that leads seamlessly to a sprawling deck, new pool and outdoor shower. You will find one of two primary suites on this floor as well as one of two laundry facilities and powder room. The 2nd and 3rd floor feature 4 generous ensuite bedrooms each with great closet space and impact sliding glass doors to balconies. Enjoy a dedicated laundry room with quartz and counters and generous storage. In addition to 3100+ sq.ft. of a/c living space. you will marvel at the outdoor living beneath the home featuring an outdoor living room with T.V , dining space and games area. Off Street parking behind an electronic gate as well and additional driveway. Come to take a look at the countless designer details that set this home apart.

$3,455,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,223 SqFt Days Listed: 412
-1.14% ($40,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

First time on the market in over 50 years! This property is a plant lovers paradise. The owner spent his entire life collecting plants and seeds from all over the world and created a quiet serene and private oasis in the middle of Old Town Key West, on a huge oversized lot. Some of the rare plants and palms are found nowhere else in the continental United States. The main house has many structural upgrades, but the best thing is that the existing carport has HARC approved plans to turn it into a large guest cottage or studio. This is an artist/musicians dream. Quiet solitude in the middle of Key West to stimulate creative juices, or just to chill out in paradise.

$3,491,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
16 Bed, 16 Baths, 6,000 SqFt Days Listed: 140
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 1714 Bertha St and 1716 Bertha St are two fourplexes with 16 bedrooms and 8 baths, 8 units of 2/1 each, comprising 6,000 sq ft of Floor Living Area on 8,755 sq ft of land, offered with the vacant lot adjacent to 1714 Bertha St, a bonus 5,765 sq ft lot comprising a total of 14,529 sq ft of land. Both buildings have new metal roofs as of 2024. Property Data Cards can be found in Documents.

$3,495,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 1,650 SqFt Days Listed: 22
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to your private oasis in the heart of Old Town Key West, where modern luxury meets historic charm. This beautifully renovated home perfectly blends timeless island architecture with sleek, contemporary comforts, offering an unparalleled living experience just steps from the Seaport and world-renowned Duval Street. Behind its classic facade, an airy, open floor plan awaits, thoughtfully designed for effortless indoor-outdoor living. Soaring vaulted ceilings crown the expansive living, dining, and kitchen space, where folding glass doors dissolve the boundaries between inside and out. The gourmet chefs kitchen features a premium Sub-Zero and Wolf appliance package, ideal for preparing island-inspired meals at home. Step outside to a lush backyard retreat anchored by a stunning saltwater pool--heated and chilled for year-round enjoyment--with a relaxing sun shelf, tranquil waterfall, and optional scupper cascades. A fully equipped poolside gazebo with a built-in grill, refrigerator, and ice maker invites unforgettable alfresco gatherings under the stars. The flexible layout includes two elegant bedroom suites and a versatile den with an adjacent full bath, perfect for guests or a home office. The first-floor primary suite offers a serene escape with a luxurious king bed and spa-inspired bath, while upstairs, a second bedroom shares a full bath and a convenient laundry area. Additional features enhance both comfort and value, including hurricane-rated windows and panels, roof certification, and a coveted X-flood zone location--offering significant savings on insurance costs. A private off-street parking space adds to the ease of island living. Tucked away on a quiet residential street yet just moments from the best of Key West, this exceptional home offers the rare opportunity to own a fully updated historic property in one of the islands most sought-after neighborhoods--where every day feels like a vacation, and every evening invites you to savor the sunset.

$3,499,000
Cudjoe Key
Cudjoe Acres   - MM: 21.50
6 Bed, 6 Baths, 4,976 SqFt Days Listed: 42
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Experience the epitome of island luxury in this custom built 5,000 sq. ft. ICF (super energy efficient insulated concrete forms) constructed estate, where masterful design, refined finishes, and breathtaking ocean views come together in perfect harmony. Situated on over an acre of prime oceanfront land, this gated and walled compound offers the ultimate in privacy, serenity, and sophisticated coastal living. Step into the light-filled, open-concept Great Room, where walls of impact doors frame sweeping views of the Atlantic Ocean. Designed to impress, the heart of the home is the chefs kitchen featuring custom concrete countertops, top-of-the-line appliances, and a layout that blends functionality with effortless entertaining. The main residence includes 4 generously sized en-suite bedrooms, all thoughtfully designed to provide a seamless balance of comfort and elegance. The expansive primary suite is a true retreat, offering stunning ocean views, a spacious layout, and a spa-inspired bath. Each guest suite is tastefully appointed to create a tranquil, private experience. For added versatility, a separate 2 bedroom guest house, complete with private entrances, serves as an ideal mother-in-law suite or a luxurious space for extended family and guests to enjoy their own secluded oasis. Step outside into your own resort-style paradise and entertain in style with a summer kitchen, multiple lounging areas, and an elevated pool featuring a waterfall, swim-up bar, and submerged seating. With over an acre of lush tropical grounds and direct oceanfront access, this property is a dream for water enthusiasts, anglers, and watersport lovers alike. This rare offering is more than a home, its an extraordinary lifestyle defined by luxury, privacy, and the natural beauty of the Florida Keys. A truly unique opportunity that must be experienced to be fully appreciated.

$3,600,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,890 SqFt Days Listed: 132
-7.57% ($295,000) 2 Price Changes : Last Change 45 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Impeccably preserved historic residence located in the heart of Old Town Key West. Discover the enticing charm of Key West and stroll through the majestic tree lined streets from 715 Frances Street. A rare combination of Key West luxury and historic architecture, this beautiful eyebrow home is perfectly positioned on a large spacious lot on sought after X Flood zone keeping you high and dry.Three beautifully appointed bedrooms, all ensuite upgraded bathrooms with a master on the ground floor and two bedrooms on second Floor.Recently completed 360 sq. ft. gazebo completes the property adding a stunning entertainers dream with outdoor kitchen, dining and seating area overlooking large saltwater pool, jacuzzi, and private garden.Gourmet kitchen finished with custom cabinetry, large countertops, gas Viking stove, Subzero appliances and glass chandeliers.Property is being sold turn key and is beautifully appointed with a stunning designer furniture package and interior plantation shutters.Additional features include full house generator, outdoor storage, off street parking for car and golf cart, outdoor shower, 2 new AC units and dehumidifier, new pool heater and chiller, new landscape lighting, new Ipe decking, Oolite stepping stones and bench, 3 new on-demand tankless hot water heaters, kevlar shutter package for entire house & 5 Camera security system.

$3,675,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 2,438 SqFt Days Listed: 78
-2.00% ($75,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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, leading to an elegant living and dining area. Throughout, gorgeous pine floors and walls highlight the homes timeless character.The open gourmet kitchen, featuring high-end appliances, flows into the living room and out to the covered loggia through vanishing pocket doors, creating seamless indoor-outdoor living. With 3 or 4 bedrooms, the main floor offers two en-suite bedrooms + a custom office, while upstairs, a spacious sitting room with a breakfast bar leads to the primary suite, complete with dual closets and a private balcony overlooking the heated pool and lush backyard.Designed for relaxation and entertaining, the large covered back porch offers serene views of the tropical landscaping and tranquil pool waterfall. A gazebo-style outdoor living space expands your backyard retreat and could easily convert back into a guest cottage as it once was.A rolling front gate, off-street parking, and a charming front porch perfect for people-watching complete this exceptional property.

$3,695,000
Key West
Tropical Bldt & Investment Co   - MM: 2.00
4 Bed, 4 Baths, 2,197 SqFt Days Listed: 167
-5.13% ($200,000) 2 Price Changes : Last Change 46 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Newly reimagined, tucked behind a picturesque white picket fence and lush tropical gardens lies, 1231 South Street. Designed to embody the relaxed elegance of the Key West lifestyle, this Conch-style retreat is a true sanctuary, featuring a main residence and a completely private guest cottage. Thoughtfully blending modern updates this single-story residence invites you to experience the essence of island living. Begin your mornings on the wraparound porch surrounded by vibrant greenery on an 8,500 SQ FT lot, expertly designed by Craig Reynolds landscape architects. This remarkable property features 4 bedrooms and 3 baths, meticulously designed for comfort and style.The spacious (24 x 20) living area features soaring ceilings and abundant natural light are perfect for hosting large gatherings. Throughout the home you will find freshly painted walls.The kitchen and dining room have been repositioned to flow naturally. The kitchen has been newly outfitted with Quartz counters. Maple cabinets, and a Wolf stainless-steel gas range complete this space . The expansive primary ensuite bedroom offers a walk-in closet, vaulted ceiling, and access to the private outdoor shower. A second ensuite bedroom includes outdoor access, a generous closet, and a unique loft space perfect for additional storage or quiet relaxation. Separate from the home you will find a private one bedroom guest cottage with an additional bath ideal for overnight guests.Outdoors, a free-flowing saltwater lagoon pool with a stone waterfall anchors the private oasis, perfect for al fresco dining. The fenced backyard offers ultimate privacy, while the covered patio, complete with ceiling fans and skylights provides a haven for conversations or watching the game. Additional features of this property include 2 private outdoor showers, laundry room, and a custom-designed carport.1231 South is located just blocks from White Streets galleries, beaches, Old Town and all Key West has to offer!

$3,749,000
Key West
Tropical Bldt & Investment Co   - MM: 2.00
4 Bed, 4 Baths, 1,802 SqFt Days Listed: 583
-5.69% ($226,000) 2 Price Changes : Last Change 78 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

If you are looking for Key West Luxury Island living at its best, then here it is 1235 Washington St. Island modernization with ultra-luxury high end finishes. This newly renovated residence is built above the current base flood elevation and designed to the latest building codes. Home features 4bedrooms/4 bathrooms of unparalleled style & sophistication. Complete with designer kitchen, build in cabinetry from Italy, quartz counter tops, and high end appliances. Home is built with CBS construction, spray foam insulation, hurricane impact windows & doors, and V-crimp metal roof which will help lower insurances and provide low maintenance. Interior has 10 ft. ceilings throughout and a grand vaulted ceiling in the living room area. Brand new salt water pool with water feature and separate pool house/guest quarters designed with carefree life style adds to the exceptional value of this amazing home. Home is furnished with new modern furniture inside and out and is available for purchase but not included in purchase price. Sit on your super beautiful front porch with tiger wood finishes and enjoy all Key West has to offer. Home is located on a 5,348 S.F. corner lot in one of the most prestigious and desirable areas of Key West. Lush tropical landscaping, irrigation, outdoor lighting, and off St. Parking completes this very desirable luxury property. Just a short distance too many of Key West fine restaurants, galleries, museums, White St. pier, & beaches. Dont miss out on this excellent opportunity to own this impressive and newly renovated luxury residence at 1235 Washington St.

$3,750,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,665 SqFt Days Listed: 328
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

Zen Villa represents a rare opportunity in the heart of Old Town, Key West, comprised of three homes on a spacious 5,891 SF lot. The main residence at 400 Aronovitz Lane is a luxurious 3-bedroom, 4-bathroom contemporary island estate and an active vacation rental, while 621 and 623 Whitehead Street offer two charming 1-bedroom, 1-bathroom cottages, currently rented long-term.The main home redefines island elegance, welcoming you with an airy lounge boasting 18-foot cathedral ceilings, a chic wet bar with granite countertops, a beverage cooler, and an ice maker. The open-concept living and dining areas flow effortlessly into multiple outdoor spaces, creating the ultimate indoor-outdoor lifestyle. Expansive sliding glass doors open to a tropical poolside oasis designed by Craig Reynolds, featuring a heated pool with a tranquil water feature, lush landscaping, ambient lighting, and a refreshing outdoor shower.The first-floor primary suite is a serene retreat with a spa-like bathroom, marble finishes, and a steam shower. The chefs kitchen is a showstopper, equipped with a large granite island, Sub-Zero and Thermador appliances, and custom lighting. Upstairs, the second primary suite opens to a private covered porch with an outdoor shower. A cozy guest bedroom with a soaking tub provides direct access to a covered patio.Zoned Historic Residential Office (HRO) with an ADA-compliant entrance, this flexible property offers endless possibilities for live-work or investment use. Just steps from Duval Street, Truman Waterfront Park, and Fort Zachary Taylor Beach, the property is located in the coveted X-Flood Zone and features 3+ off-street parking spaces. Dont miss the chance to own a piece of paradise--schedule your private tour today!

$3,750,000
Key West
Tropical Bldt & Investment Co   - MM: 2.00
4 Bed, 4 Baths, 2,585 SqFt Days Listed: 519
-5.06% ($200,000) 2 Price Changes : Last Change 65 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

BRAND NEW CONSTRUCTION. Four bedrooms, 4.5 bathrooms including guest quarters and pool. High end trim package includes Thermador appliances with wet bar, 58 bottle dual temperature wine cooler, beverage center, ice maker, induction stovetop. Upstairs and downstairs laundry. Riva European white oak wood flooring manufactured in Spain, white Thassos marble in primary first floor bath. Free standing bathtub in beautiful shower enclosure in second floor bath. Euro sliders that create a 16 foot opening to Ipe decking, oolite walking paths with crushed granite. Saltwater pool with all Pentair equipment, automation for heater/chiller, waterfall, LED lighting, 65K BTU multi speed pump. Remote controlled gate for secure off street parking and separate secure off street golf cart space. Lush landscaping with lighting and irrigation. Warranties still in place. Owner is Florida licensed real estate agent.

$3,750,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
4 Bed, 4 Baths, 3,228 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Boat S

BOATERS PARADISE FOUND with an unobstructed sunset view over open water year round on oversized corner lot with water on 2 sides at the very end of a private road offering picture perfect sunsets in a protected bay! Boasting 323 of water frontage, this property includes 175 of open water and 148 of canal frontage featuring a 90 concrete dock, and a private kayak launch. The main level of the home features a wrap-a-round deck, a spacious living area, including a large master bedroom and bathroom with jacuzzi tub, separate shower & his & hers vanities, 2nd bedroom, half bathroom and a chefs kitchen with Sub Zero Fridge. The third level has a private bedroom, bathroom and balcony accessible by a spiral staircase. On the opposite side of the home is a private mother-in-law/teen suite that could be separated and or rented separately with an open floor plan that includes a large living area, 2 Story tongue & groove West Indies Great room w/wet bar and its own updated kitchen with brand new SS appliances overlooking the water! Smart home panels & security cameras thruout. The home is being sold fully furnished w/exception of a few personal items. Outdoor living including new Giant 16ft Swim Spa w/55 jets, blue tooth ss & fiber optic lights that fits 14 people, outdoor sun TV, pool table, lounge chairs, multiple hammocks & grill. Boat Dockage is super with room for up to 42 ft boat plus a floating Jet Ski Dock that holds 2 Jet Skis! Plenty of parking underneath 12ft concrete pillars for all the guests w/an efficiency for storage as well! Easy access with channel directly in front of home, super fishing spots & reefs! Only 20 mins to Key West w/plenty of shopping, Nightlife and super restaurants. Home was recently tented & has fresh paint, lighting, updated electrical. Home is entirely fenced & Gated w/privacy PVC fencing. The best of all is the wide open water & gorgeous sunset views! Owner/Agent

$3,750,000
Key West
Gg Watson Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,721 SqFt Days Listed: 131
-16.67% ($750,000) 3 Price Changes : Last Change 72 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key Wests historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a light-filled sanctuary where 14-foot cathedral ceilings crown an expansive open-plan living, dining, and chefs kitchen area. French doors seamlessly blend indoor and outdoor living, inviting you to a private paradise. The spacious kitchen features Caesarstone Quartz countertops, a Sub-Zero refrigerator, a Wolf gas range, Fisher & Paykel double-drawer dishwasher, beverage drawers, and a microwave drawer. Outdoors, indulge in Key West living at its finest with a sparkling heated swimming pool, a large deck for entertaining and sunbathing, a serene waterfall, and lush tropical landscaping. A covered sitting area offers the perfect spot to unwind. There is a Sonos sound with Focal low-profile speakers to fill the air with your favorite tunes throughout the main house. The main house features two guest rooms, a shared bathroom and a washer and dryer conveniently located between them, and a luxurious primary suite with its own washer and dryer. Impact windows and doors ensure peace of mind, while privacy fencing and off-street parking for two cars provide unmatched convenience. A super cute, separate guest house completes this property, offering two ensuite bedrooms, a kitchenette, a dining area, and a loft sitting space--perfectly positioned at the back for ultimate guest privacy. A storage shed for pool toys and tools ensures everything has its place. This Key West masterpiece is a rare gem, blending timeless charm with modern luxury. Dont miss the chance to own your own slice of paradise in this superb location! Easy to show! Video link https://n9.cl/1114packer

$3,795,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
4 Bed, 4 Baths, 2,628 SqFt Days Listed: 96
-4.53% ($180,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builders constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between interior and exterior space. The house features elegant tile floors throughout the first floor, while the second level is distinguished by luxurious hickory wood flooring. The dining room is tailored to accommodate a bespoke layout, complete with ambient mood lighting and refined cove molding. A a generously proportioned bedroom and bathroom, complete with private access to the pool area, are nestled at the rear of the first floor. This stunning four-bedroom, five-bathroom residence boasts an impressive 2,628 square feet of living space, set amidst a meticulously landscaped 5,600 square-foot lot. The masterful landscaping is the work of a renowned expert, celebrated for work on the most exclusive properties in the Florida Keys. The main bedroom of this stunning residence boasts a robust layout and sliding doors that open onto the upstairs balcony. The expansive wrap-around balcony also provides access to the two additional bedrooms, each featuring its own bathroom. The propertys reflective metal cool roof is engineered to optimize energy efficiency and provide year-round comfort. Moreover, three independent air conditioning units ensure a consistently cool environment. There is also a 500 gallon underground gas tank and a 2.2kw house generator. Additional features include off-street parking for multiple vehicles, a private driveway, and secure electronic gates and security camera system, solidifying this propertys reputation as a masterpiece of timeless craftsmanship. Once you step inside, its allure will undoubtedly capture your heart.

$3,799,000
Key West
Gwynn Subdivision   - MM: 1.00
5 Bed, 5 Baths, 2,960 SqFt Days Listed: 218
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Introducing Blu on White one of Key Wests most stunning historic single level residences in desirable Old Town Key West. Exceptional location scoring a full 10 on the walkability scale with easy access to the beaches, White St. Pier, an array of galleries, restaurants and cafes.Taking full advantage of the generous 5800 sq ft. lot, this 5BD/4BA home offers so much space and versatility with almost 3000 sq ft. of interior living space. Currently configured as a 4BD/3BA main house with a separate 1/1 apartment with private entrance. The apartment is perfect for a nanny, mother in law and also offers an excellent source of income as it comes with a transient license which will permit nightly rentals. Current owner operates the apartment as a nightly vacation rental and numbers can be provided upon request. The main house is currently being operated as a monthly vacation rental with a strong rental history and excellent future bookings, which will convey with the sale.Originally two historic shotgun homes, this home has been expertly merged to create a breathtaking great room addition that overlooks the stunning saltwater pool and garden. Featuring a high vaulted ceiling with post and beam design, wide plank wood floors, skylights for additional natural lighting, built-in bookshelves and large impressive impact sliders creating an enviable ambiance you will never want to leave.Prepare to be captivated by the heart of the home, the luxuriously appointed kitchen, crafted with the finest materials & unparalleled design, this culinary haven is perfect for any aspiring chef and those who love family gatherings, with gas Viking stove & appliances, European style open shelving, excellent prep space and large interior dining area. Additional features include oversized saltwater pool, private tropical landscaped garden and cozy shaded Gazebo, storage shed and so much more.The epitome of a fine Key West Historic Home combining luxury and versatility

$3,799,000
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 3,171 SqFt Days Listed: 146
-10.61% ($451,000) 6 Price Changes : Last Change 40 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this versatile property is situated in the X flood zone and offers four off-street parking spaces. The main house, a meticulously renovated mid-century modern gem, welcomes you with a grand entrance foyer that flows into a spacious living, dining, and media area. Perfect for entertaining, the space features a working fireplace and a 76-inch TV. The gourmet kitchen boasts solid wood cabinetry, Bosch and Thermador appliances, an induction cooktop, column fridge/freezer, wine cooler, and an impressive 13-foot quartz waterfall island. Impact sliding doors open to a stunning saltwater pool complete with a sun ledge, slide, and waterfall. Surrounded by tropical landscaping, this backyard oasis also features an outdoor shower, fully equipped kitchen, and plenty of space for entertaining. The main house offers four bedrooms, each with generous closet space and outdoor access. The primary bedroom includes a new custom walk-in closet with solid maple built-ins. Another ensuite bedroom has been transformed into a stylish home office with a built-in Murphy bed. The two additional bedrooms share an elegant bathroom featuring a luxurious soaking tub and shower. Adjacent to the main house is a charming two bedroom, two bath Conch-style cottage that provides the perfect guest retreat or mother-in-law suite. This home features a fully equipped kitchen, Dade County pine accent walls, and a tranquil outdoor space to relax under the shade of swaying palm trees. Dont miss the chance to see this unique compound that provides the perfect blend of history, luxury, and the ultimate Key West lifestyle!!

$3,945,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
4 Bed, 4 Baths, 3,817 SqFt Days Listed: 164
-17.80% ($854,000) 3 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift150ft.Concr

Exquisite LUXURY Waterfront Estate in the prestigious Cudjoe Gardens. A STUNNING TURNKEY PARADISE, SOLD AS IS WITH HIGH END DESIGNER FURNISHINGS & DECOR FROM RESTORATION HARDWARE, POTTERY BARN, & SERENA AND LILY. ALSO 2 HOBIE CATS. This Custom Built Home with a total of 5,373sf under roof is a masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling waterfront ELEVATED corner lot of 16,500sf with 260FT of water frontage and deep draft. This gorgeous property offers an unparalleled tropical lifestyle, perfect for those who demand the best in comfort and elegance.Property Highlights4 Bedrooms + Office/Studio: Spacious, sunlit rooms designed for relaxation and productivity, including a versatile office or creative studio space which could be a 5th Bedroom.4 Full Bathrooms: Impeccably designed with high-end fixtures and finishes.Gourmet Kitchen: A chefs dream, featuring state-of-the-art appliances, custom cabinetry, and expansive Quartz countertops ideal for entertaining.Imported Italian & Moroccan Flooring: Stunning, high-quality flooring that enhances the luxurious ambiance throughout.12-16 Ft Ceilings: Create an open, airy feel while showcasing architectural sophistication.Saltwater Pool: Dive into the generously sized, chilled & heated concrete pool with water feature, lights and lounging platformOutdoor Kitchen: Stainless Steel Appliances, Spacious layout, Perfect for entertaining.2 Boat Lifts, 20k and 10kAdditional Amenities3 A/C Units: Individually climate-controlled zones, including the 3-car garage for comfort and convenience.Full Property Generator, 1000 gallon Propane Tank, Full Security System, Phantom SunShades for Screened in PorchThis meticulously designed property combines sophisticated interiors with exceptional outdoor living spaces. Located in a prime area of Cudjoe Key, this home offers privacy, stunning water views, and direct access to the pristine waters of the Lower Key

$3,999,000
Key West
Old Town Unlisted   - MM: 1.00
7 Bed, 7 Baths, 3,015 SqFt Days Listed: 135
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This property has a glamourous three bedroom, three and a half bath owners unit with private pool and hot tub, plus three lucrative long-term rentals. It is the entire Lighthouse View Condominium Association, currently inactive. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence with its heated pool and hot tub is secluded in the rear with a pretty garden and brick terrace. A free-standing two story building contains a great room, splendid kitchen and half bath downstairs. Above is a bright and breezy master suite with cathedral ceilings and skylight. In addition, there are two guest cottages, each with one bedroom, one bath and a pretty front porch. On the deck between the cottages is an outdoor wet bar and there is an outdoor shower by the pool. The other apartments are in a building at the front of the property. Downstairs are two one bedroom-one bath units. Upstairs is a glamorous two bedroom-one bath with a big, wonderful deck under the trees.

$3,999,000
Key West
Old Town Unlisted   - MM: 1.00
7 Bed, 7 Baths, 3,015 SqFt Days Listed: 140
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

This is the entire four-unit Lighthouse View Condominium Association. It is currently four lucrative long-term rentals. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence is secluded in the rear with its own private heated pool, hot tub and expansive garden with brick terrace. A free-standing two story building contains a great room, splendid kitchen and half bath downstairs. Above is a bright and breezy master suite with cathedral ceilings and skylight. In addition, there are two guest cottages, each with one bedroom, one bath and a pretty front porch. On the deck between the cottages is an outdoor wet bar and there is an outdoor shower by the pool. The other apartments are in a building at the front of the property. Downstairs are two one bedroom-one bath units. Upstairs is a glamorous two bedroom-one bath with a big, wonderful deck under the trees.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 05-20-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA