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$4,000,000 - $5,000,000 Florida Keys Homes For Sale - Real Estate

Total Listings 36
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$4,700,000
Plantation Key
Sunshine Estates   - MM: 90.50
5 Bed, 5 Baths, 4,100 SqFt Days Listed: 145
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Welcome to Paradise at 115 Spoonbill Road! This luxurious canal-front new construction home offers direct bay access and ocean access through Tavernier creek. Spanning 4,100 sq. ft. of air-conditioned space, this brand-new custom-built home features 5 spacious bedrooms and 6 elegant bathrooms.On the upper level, the serene master suite invites relaxation with a large walk-in closet, beverage center, expansive shower, and his-and-her sinks. Three additional guest suites--each with its own bathroom--a spacious living area, large laundry room, and a flexible bonus room perfect for a gym or office complete this floor.The lower level is designed for entertainment and convenience. The gourmet kitchen boasts top-of-the-line appliances, quartz countertops, a wine cooler, and custom cabinetry. The main living area, along with a guest suite and full bath, flows seamlessly to the outdoor oasis featuring an outdoor kitchen and gazebo, synthetic grass, a sparkling pool, and a full 70 feet of dockage--perfect for boating enthusiasts.

$4,775,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,716 SqFt Days Listed: 127
-2.55% ($125,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a wonderful, covered porch.Discover the timeless elegance of its living room, dining room, and a fantastic den with an open kitchen floorplan complete with Viking appliances. Step outside to enjoy your covered patio, private pool, and inviting outdoor living areas surrounded by lush tropical foliage. Driveway for two cars with one covered parking space.Perfectly situated for exploring Key Wests vibrant attractions, this home offers a rare opportunity to own a piece of island history while indulging in the ultimate Key West luxury lifestyle.

$4,850,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,148 SqFt Days Listed: 10
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, youre greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest . Included is a Truman Annex transient rental license allowing for weekly rentals, 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, the residence comes complete with all furnishings and future reservations, promising a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.

$4,850,000
Key West
Kamien Plat #2   - MM: 2.00
4 Bed, 4 Baths, 3,154 SqFt Days Listed: 120
-5.83% ($300,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover the epitome of island elegance with this stunning Spanish Mediterranean-style home situated on an expansive 10,000+ sq. ft. corner lot in the heart of Key West. This exceptional property offers over 3,100 sq. ft. of living space, featuring 4 spacious bedrooms and 3 full bathrooms. Step inside to find a light-filled living and dining area that seamlessly opens to a lush tropical oasis, complete with mature landscaping and an oversized heated saltwater pool--an entertainers dream. The chef-inspired kitchen is designed for those who love to cook, offering ample space and functionality. The first-floor primary suite is a true retreat, boasting an ensuite bathroom and charming French doors that lead to the expansive garden and pool area. Upstairs, youll find 3 additional generously-sized bedrooms and a full bath, perfect for family and guests. Adding to the homes appeal is a carport providing off-street parking for 2, a whole-home generator for peace of mind, and an ambiance that perfectly balances indoor and outdoor living. Experience the ultimate Key West lifestyle in this one-of-a-kind Key West residence!

$4,900,000
Key Largo
Point Pleasant   - MM: 99.50
5 Bed, 5 Baths, 3,208 SqFt Days Listed: 97
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat RampC

Where Paradise and Luxury Meet!Endless bay views can be yours in this luxurious bayfront, modern Caribbean-style pool home. Situated on an oversized bayfront lot, nearly a 1/2 acre, this stunning property offers breathtaking sunsets every evening.Built as a solid concrete fortress, this home is equipped with all-impact windows, doors, and a metal roof, providing unparalleled strength and peace of mind. With 5 bedrooms and 5.5 bathrooms, it is the perfect home for a large family, offering both elegance and security.Completely elevated above the flood zone, the residence exudes luxury throughout. The ground-level suite features a private entryway, a junior master lounge, and a separate living space. Upstairs, youll find three additional bedrooms along with an impressive master suite boasting an ensuite bath, a soaking tub, and a spacious walk-in shower.The resort-style pool, spa, and deck have been freshly refinished within the last two years. The pool system includes a salt system, an electric heater and chiller, and a propane system for enhanced efficiency. The property also features a private white-sand beach, a kayak and jet ski ramp, and a newly reinforced seawall spanning the width of the waterfront.The impressive pier dock includes two boat lifts:A 35,000-lb lift (1 year old)A 7,500-lb lift (4 years old)Additional upgrades include new air conditioning units, new hot water tanks, and a brand-new mini-split system in the garage.This is a rare opportunity to own a luxurious bayfront retreat where modern elegance meets the serenity of island living!

$4,950,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 2,985 SqFt Days Listed: 145
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover the perfect blend of historic charm and modern elegance in this fully renovated and expanded Key West home, tucked away on a picturesque lane. Offering 4 bedrooms, 4.5 bathrooms, and 2,985 square feet of thoughtfully designed living space, this property is a rare find. The light-filled interiors feature soaring cathedral ceilings and walls adorned with rich Dade County pine, seamlessly blending classic character with contemporary upgrades. Engineered wood floors flow throughout, while the downstairs master suite boasts a spa-like bathroom with marble floors and travertine walls. Entertain effortlessly with high-end Miele appliances in the gourmet kitchen and a custom bar complete with an icemaker. The home opens to a private outdoor oasis, where an ipe deck surrounds a heated and chilled saltwater pool. Two outdoor showers complete the tropical lifestyle experience. This 4,616-square-foot lot also includes two off-street parking spaces, 2 custom stair cases, Cummins diesel generator, impact glass windows for peace of mind, and a durable metal shingle roof. Additional features include two central A/C systems and the finest materials throughout, making this home as functional as it is beautiful. Whether relaxing in the elegance of your home or enjoying the vibrant lifestyle in Old Town Key West, this property is the best location for it all. Home is expected to be completed in the next 4-5 weeks. ***Images are renderings and are approximations of the finished product, not representations. ***

$4,950,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 2,907 SqFt Days Listed: 44
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift100ft.

Huge Price Improvement! Welcome to your waterfront paradise! This solid concrete, newly built 4-bedroom, 4.5-bath home offers unparalleled luxury finishes and an open floor plan designed for modern coastal living. The chefs kitchen is a culinary dream, featuring state-of-the-art appliances and an open layout flowing seamlessly into the spacious living and dining areas. Expansive balconies offer beautiful views and include a summer kitchen for outdoor dining and entertaining. The master suite is a private oasis on its own floor, complete with a sun deck, walk-in closets, and a large balcony perfect for relaxation.With a 100-foot seawall, a 25,000 lb boat lift, and a floating dock for jet skis, this property is an ideal base for water enthusiasts. Relax in the heated pool or enjoy the thoughtfully designed outdoor spaces for cooking and lounging. Just 20 minutes from Key West and 15 minutes from Marathon, this luxurious property combines convenience and tranquility. Furniture, boat, and jet ski are available as optional add-ons, making this turnkey retreat an exceptional opportunity to own your piece of paradise!

$4,950,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,100 SqFt Days Listed: 214
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout.Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation.On the main floor, the gourmet kitchen is a chefs dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock.This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

$4,975,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
3 Bed, 3 Baths, 1,264 SqFt Days Listed: 372
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

$4,995,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 3,026 SqFt Days Listed: 565
-7.48% ($404,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance.With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key Wests most coveted neighborhoods. Constructed in 1899 by renowned William Cash, this estate radiates a colonial grandeur, enriched with a cranberry cut -glass transom sophisticated dark green shutters & classic french doors.The current owners have meticulously restored the property using only the finest selection of materials, from river reclaimed old growth hardwood floors in living room and hallways, to stunning Blue Castle Limestone in master suite and kitchen and continued through the magnificent garden and pool to the separate guest quarters. Smarthome features have been introduced, including Zigbee Lights integrated with Home assistant, sensor mixs, Ecobee Thermostats, 6 Node Eero Mesh Network, Abode Alarm Systems & Nest protect Sensors.The master suite located on the ground level is a peaceful sanctuary with private library & den, exceptional ensuite, three sets of French doors and opens out to the magnificent saltwater pool and tropical landscaped garden. Two additional bedrooms on second floor in main house share a bath and private veranda.Separate cottage provides exceptional guest quarters and can be accessed from Roberts Lane for additional convenience. Stunning post & beam cathedral ceilings, Limestone floor, built-in bar and kitchenette and spacious living room offers excellent space for entertaining with deck and pool access.Additional features include, One off-street parking spot, equipped with Tesla charging station & new 2023 generator powered by dual propane tanks.Welcome to Key West Living at its finest.

$4,995,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 4,014 SqFt Days Listed: 227
-20.65% ($1,300,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this residence offers ample space for family and guests. Enjoy stunning ocean views from various vantage points within the home, enhancing the comfort and breathtaking natural beauty. The observation dock provides a perfect spot for relaxation, while the saltwater pool equipped with heater/chiller, ensures year-round enjoyment. Added features are quartz countertops, top-of-the-line appliances and the Residential Estate zoning allows weekly vacation rentals with a high-income stream.This combination of amenities creates an inviting atmosphere that reflects the privacy and charm of the Florida Keys lifestyle.

$4,999,000
Marathon
Crains Subdivision   - MM: 58.00
3 Bed, 3 Baths, 4,000 SqFt Days Listed: 176
-15.98% ($951,000) 2 Price Changes : Last Change 27 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin

Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 5,220 sq. ft. and is highlighted with a ton of amenities including two docks, 4 post boat lift, private sandy beach and an infinity-edge elevated pool blending seamlessly with the gulf and featuring a built-in table and chairs for relaxing or entertaining. Expansive covered areas by the pool offer shaded spots for lounging and has direct access to the living areas. Double entry doors with intricate carved wood details welcome you into a light-filled home. The open-concept living area is graced by large windows and sliding glass doors that frame panoramic views and create a seamless connection between indoors and outdoors. A striking marble fireplace serves as the focal point. Every element of this home reflects thoughtful design, from the impact-rated doors and windows, in-house elevator plus marble floors, exquisite cabinetry, and refined finishes enhancing the homes timeless appeal. The main kitchen is a chefs delight, featuring granite countertops, two wine coolers, and abundant cabinetry. A cozy dining nook encased in windows offers stunning gulf views, creating the perfect setting for every meal. The primary suite is a sanctuary of luxury, featuring panoramic gulf views, a two-sided fireplace, and direct access to the pool. The en-suite bathroom offers a private sauna, jetted tub, walk-in shower, and makeup counter, creating a spa-like retreat. The guest quarters are designed for comfort and independence, offering a morning kitchen and two guest suites. Each suite includes its own en-suite bathroom and generous closet space, ensuring privacy and convenience for visitors. The large office can also serve as a 4th Bedroom. Additional amenities include a home theater room complete with reclining seats and bar plus an oversized 3-car garage with lift.

$4,999,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 3,906 SqFt Days Listed: 376
-9.09% ($500,000) 1 Price Change : Last Change 43 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift150ft.

Enjoy this OPEN WATER luxury lifestyle in the coveted area of Buccaneer Point Estates in south Key Largo. Prepare to be captivated by this 5 bedroom, 4 bath extraordinary waterfront masterpiece that combines modern elegance and over 3,900 sq. ft of living space with a tropical paradise ambiance. Nestled on the shores of the bay, this custom-designed home has been thoughtfully crafted with discerning clients in mind. This rare offering promises a lifestyle beyond compare, where every moment is infused with the allure of the Florida Keys. As you step inside, ascend the interior stairs from the grand foyer to the main living level, where cathedral ceilings and an abundance of natural light create an inviting atmosphere. Revel in the breathtaking water views framed by expansive windows and doors, seamlessly blending the beauty of the outdoors with the comfort of your luxurious sanctuary. The heart of this residence lies within the great room, where a well-appointed double island creates the perfect setting for entertaining while the expansive porch areas beckon you to soak in the tranquil vistas. Designed to accommodate a large family or gathering of friends, this home boasts two master ensuites on each level, ensuring privacy and comfort for all. In addition, three guest bedrooms with adjoining bathrooms provide ample space for everyone to unwind and recharge. For water enthusiasts, this home is a dream come true with an inviting in-ground heated pool, surrounded by a custom paved deck area and lush privacy landscaping. The deep water pier dock features a boat lift and jet ski lift. The spacious four-car garage with dual doors, a second refrigerator, an ice maker, and the potential for a bar or summer kitchen makes it a versatile space for hosting unforgettable backyard gatherings.

$4,999,000
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 3,462 SqFt Days Listed: 131
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

Nestled along the pristine shores of Buccaneer Point, this exquisite bayfront estate offers an unparalleled fusion of opulence, tranquility, and sweeping water views, redefining luxury living in the Florida Keys. Perfectly positioned at the tip of the peninsula, this exceptional property offers breathtaking panoramic views of the bay from every major living area. Experience unrivaled privacy and serenity with conservation land bordering the property to the West, ensuring unobstructed vistas and a tranquil setting.This meticulously updated 5-bedroom, 4-bathroom estate combines modern elegance with resort-style amenities. The open-concept gourmet kitchen is a chefs delight, featuring high-end appliances, custom cabinetry, and seamless flow into the expansive living and dining spaces--all with stunning water views. A sleek glass elevator provides effortless access to all levels, making every part of this home easily accessible.Step outside to your personal paradise: a lush backyard with low-maintenance turf, a custom putting green, and an inground pool equipped with heaters for year-round comfort. Boating enthusiasts will appreciate the 15,000-pound boat lift, offering direct access to the bay for endless adventures on the water.Additional highlights include a spacious two-car garage, ample storage, and a quiet cul-de-sac location that ensures privacy. Whether youre relaxing poolside, savoring sunsets from the expansive balcony, or entertaining guests in style, this home truly embodies the ultimate in luxury coastal living.Dont miss the rare opportunity to own this spectacular bayfront retreat in coveted Buccaneer Point Estates--schedule your private showing today!

$4,999,900
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
4 Bed, 4 Baths, 3,001 SqFt Days Listed: 43
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chefs kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys most sought-after locations.

$4,999,999
Key Largo
Buccaneer Point   - MM: 98.00
5 Bed, 5 Baths, 4,732 SqFt Days Listed: 158
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift200ft.

Modern Coastal in Buccaneer Point Estates. This bay front solid CBS home tucked away near the end of a private street offers unparalleled privacy and the sought-after allure of waterfront living. Experience a masterpiece built to incorporate and withstand natures elements. Interior and features that draw on the natural backdrop fusing coastal design w/contemporary architecture. Upon entering the residence and ascending the stairs, panoramic waterfront views unfold across the entire home through floor-to-ceiling windows. Fluidity in design is the essence of the concept for this home. The kitchen is adorned with opulent finishes including sleek quartz countertops, lacquer kitchen cabinets, a natural wood island, recessed lighting, and Thermador appliances. This home offers 5 bedrooms, 3 full bathrooms, and 3 half bathrooms. Two spacious bedrooms share a bathroom on the main living level with an additional half bath in the hallway and additional 2 bedrooms located on the third floor share an adjoining bathroom. The primary suite features floor-to-ceiling windows overlooking the bay, two private balconies, an office nook, and a resort-style bathroom. Notable features in the primary suite include a custom walk-in closet, a dual entry rain shower, a stand alone jet tub, and marble tile throughout. Continue up the stairs to access the rooftop terrace where you can enjoy 360 degree sunset views, soak in the hot tub, entertain guests, and serve drinks from the enclosed wet bar! Complete with an elevator accessing each floor up to the third story. Outdoor amenities include an in-ground pool, artificial turf grass, mature landscaping, cabana pool space, a two-car carport, charging station and a pier dock offering deepwater dockage for all your vessels including a 20,000 pound lift and jet ski lift. This location offers unparalleled boating access with close proximity to Adams Cut & Tavernier Creek for ocean access. We invite you to experience the epitome of coastal living.

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 06-16-2025.
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