33040 Real Estate Homes For Sale - (Single Family Houses) in 33040 Zip Code

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.

Tucked behind swaying palms and lush tropical landscaping, this elegant and timeless waterfront estate captures the essence of Florida Keys living--from breathtaking sunset views to exceptional outdoor spaces. Whether youre lounging on your private beach or entertaining by the pool, every moment here is a reminder of why you chose island life.Inside, sun-drenched living areas showcase wide-open Gulf views and an abundance of natural light. The gourmet kitchen is thoughtfully designed with custom cabinetry, high-end appliances, and a spacious island--ideal for both everyday living and entertaining. Upstairs, the master suite features panoramic water views and a generous walk-in closet. Three additional bedrooms are located on the upper level, with a fifth bedroom and full bath on the main level offering added flexibility.Designed for seamless indoor-outdoor living, the home opens to a private deck, sparkling pool, and an observation dock--perfect for catching every sunset. Additional features include a copper patina roof, a 3-car covered carport, full generator, ample storage and a wave runner lift.Located in the prestigious, gated community of Shark Key, just minutes from Key West, this estate offers access to resort-style amenities including a clubhouse, inland swimming lagoon and beach, plus pickleball and tennis courts.24 Cannon Royal Drive is everything you love about the Keys--all wrapped into one exceptional waterfront property.

Welcome to 3300 Riviera Drive--an exceptional, turn-key, waterfront, residential estate featuring 4 bedrooms and 4.5 bathrooms. Nestled on three lots in a serene enclave just minutes from Old Town, this meticulously maintained property features 3,577 Sq. Ft. of living space and redefines Key West luxury, comfort and convenience. Step inside to discover an expansive open-concept living space bathed in natural light, with elegant finishes that include custom cabinetry, granite counters and hardwood floors. The gourmet remodeled kitchen, complete with high-end appliances including two dishwashers and a generous island, flows effortlessly into a spacious great room--ideal for entertaining. Wall to wall impact-rated sliders lend to an indoor/outdoor feel throughout the space, and lead to an expansive outdoor living area that overlooks the pristinely landscaped, resort-like grounds. Retreat to the primary suite, a private sanctuary featuring serene water views, wrap-around balcony, a spa-inspired bath with a steam shower and ample, two walk-in, closet space. Additional bedrooms, all with ensuite bathrooms, offer flexibility for guests, home office, or fitness needs. A gracious guest house, one bedroom and one bathroom, is located above the two car garage which gives your guests total privacy.Outdoors, lush tropical landscaping surrounds a stunning pool and patio, creating a peaceful ambiance with sunset views over the canal. A private sea-wall with boat lift offers direct access to open water -- perfect for boating enthusiasts. Additionally, an electric gate leads to a climate-controlled two-car garage, ideal for storing vehicles. A two car carport is also located just out side of the garage, you can park four vehicles that will be covered from the elements, you just cant find this in Key West.Built with security and peace of mind in mind, the concrete property is elevated and includes impact-rated windows and doors throughout. Call today!

Welcome to one of Shark Keys landmark estates--a custom-built, beautiful Mediterranean-inspired home. This exclusive property offers timeless architecture, open water views, and an unparalleled island lifestyle.Nestled on the northern end of Shark Key and set back from the road for privacy, this 5,300-square-foot estate sits on a 21,075-square-foot lot with breathtaking open water views. Designed for comfort and entertaining, the home features 4 bedrooms, 4.5 bathrooms, a private office, a home theater, an elevator, a full bar, and expansive balconies and elegant terraces that invite you to take in stunning sunrises and peaceful water views.Each of the bedrooms has an ensuite bathroom and private balcony, while the primary suite boasts incredible water views. The outdoor living spaces are equally impressive, featuring a pool, hot tub and ample room for entertaining and lounging. Theres also space to add an observation dock for a flats boat.Enjoy the exclusive amenities of Shark Key, including pickleball, tennis courts and a private sandy beach. Located just minutes from Key West, yet offering a private retreat, this estate is truly one of a kind.This lovingly maintained home presents an exciting opportunity to update and make it your own while preserving its classic Mediterranean charm.Dont miss this rare offering--schedule your private showing today!

Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. A recently sold $3.5M, 4000 sq. ft. home was torn down just to obtain a buildable lot on Hilton Haven. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock while overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75 by 300 bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living rooms custom hand built beamed wood cathedral ceiling and a majestic staircase. The current sunroom, converted into a dining room, features French doors that open to views of the pool and harbor. The expansive deck leads down to the lower entertaining level. The chefs kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to the rear private deck and dock. Completing the first floor are the laundry room, a half-bath, a full bath, and a charming guest bedroom. The sunroom with a wet bar and bathroom provides access to the one car garage, and second staircase leading to the second-floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. https://show.tours/e/4vNFpvG

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12 ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chefs dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views perfect for outdoor lounging. Two charming, detached guest houses each with full baths and one offering a living room and kitchenette allows secluded spaces for all to enjoy. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill that provides the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear ocean, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Dont miss the opportunity to be able to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent.

Property is being sold with MLS #614840This waterfront home on a canal in Key West is ready for your creative touch! With 3 bedrooms, 2 bathrooms, a large 9794 sqft lot and there is plenty of room for the boating enthusiasts. It has a large in ground pool and outdoor fire pit area. **You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase or both homes. Make this a large family compound or reconfigure to one large estate. The possibilities are endless.**

Property is being sold with MLS #614841This 3 bedroom 3 bathroom home is located on Riviera canal in Key West. It sits on a 10,000+sqft lot, has a newer pool, outdoor kitchen, 24,000lb boat lift, and outdoor shower. There is plenty of parking, air-conditioned storage and large patio for outdoor entertainment. With its original cuban tile and vaulted ceilings if offers a charming old Key West vibe. **You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase of both homes located at 3608 & 3612 Sunrise Drive.Make this a large family compound or reconfigure to one large estate. The possibilities are endless.**

3608 Sunrise Drive & 3612 Sunrise Drive are located next door to each on Riviera canal in Key West. You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase or both homes. Make this a large family compound or reconfigure to one large estate. The possibilities are endless.See MLS#s 614840 & 614841 for more photos and property details.

This Key Haven Estate rests on over 15,000 square feet of land with more than 260 linear feet of water access all while boasting over 6500 square feet of the finest living accommodations in the Florida Keys. The main Home has 5 Bedrooms and 4 and 1/2 bathrooms, the guest house has 3 bedrooms and 3 bathrooms. 39 Evergreen has the finest finishings all encased in 11 inches of solid concrete using insulated concrete forms and solid poured floors and stairs. Utilizing this type of Construction not only provides tremendous safety and privacy but allows for the impact glass windows and doors to be protected by hidden European style roll down shutters. The home has a vast 60 long pool with multiple levels, waterfalls and 6 seats to the swim up bar in the custom gazebo, perfect for entertaining, or when you are finished in the homes Private 400+ Square foot Gym. This home can accommodate over 9 vehicles in its 3800 Square Foot garage and has a Generator and Fire Suppression system for additional safety and security.

Timeless European Elegance! This custom 4BD/5BA Mediterranean villa in gated Shark Key offers 5,180 SF of luxurious living. Features include soaring ceilings, gourmet Viking kitchen, office, game room, and stunning open-water views. Enjoy indoor-outdoor living with expansive decks, pool, fireplace, and multiple entertaining areas. The spacious primary suite includes a sitting area, wet bar, dual walk-ins, and private terrace. Additional highlights: Borano mahogany doors, elevator-ready design, chair lift, impact windows/doors, dual garages, and first-floor guest suite. Amenities include private lagoon, beach, tennis, pickleball & clubhouse. Furnished with exclusions.

Located on iconic Millionaires Row in the heart of Old Town Key West, this extraordinary estate offers a rare combination of timeless charm, modern luxury, and unmatched privacy. With two stunning homes both with impact rated windows and doors on one oversized lot, this tropical compound is an exceptional opportunity to own one of the most unique properties in Key West.The main residence, a beautifully restored historic home, features four ensuite bedrooms, including a flexible downstairs suite that doubles as a den or office. Classic Dade County pine walls, high ceilings, and an abundance of natural light create a warm yet sophisticated atmosphere. The gourmet kitchen is outfitted with custom cabinetry, sculpted marble countertops, Sub-Zero and Wolf appliances, and complete with a built-in wine cooler and coffee center. A spacious 12-person dining room and wraparound porch invite relaxed island entertaining with elegant flair.The newly built guest house offers two additional ensuite bedrooms, soaring vaulted ceilings, exposed beams, a cozy loft, and a fully equipped kitchen with Miele appliances and stunning artisan tile. Ideal for hosting guests or enjoying extended family stays in total comfort and style.At the center of the estate lies a tropical paradise, designed by renowned landscape architect Craig Reynolds. A sparkling saline pool, cascading waterfall, outdoor shower, and private half bath make this backyard feel like your own private resort.With reclaimed river wood floors, rare off-street parking for two, every inch of this property has been crafted for beauty, durability, and ease of island living.1109 Fleming Street isnt just a home--its a rare slice of paradise in the best location Key West has to offer.

Motivated Seller! Discover luxury living in this stunning 4BD/3.5BA custom home in the exclusive gated community of Shark Key. Featuring 3,875 SF of refined space, this residence offers soaring ceilings, designer finishes, a gourmet kitchen with Wolf & Miele appliances, and seamless indoor-outdoor living. Enjoy a heated infinity pool, spa, and breathtaking Gulf sunsets. Dual primary suites, office/flex room, EuroCave wine bar, and lush tropical surroundings complete this waterfront oasis. Private, secure, and built to impress.

With its special transient license, The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. Whats interesting is that most of the rental income comes from monthly rentals, so you can expect almost as much income without a transient license. This extraordinary home is situated on one of the largest lots (14,183 SF) in Truman Annex and is being offered as the ultimate turnkey property. There are a total of 5 bedrooms and 4 bathrooms: 3 bedrooms and 2 bathrooms in the main house and two 1 bedroom, 1 bathroom private cottages. This expansive property includes a covered seating and dining area under the gazebo, which overlooks the resort-style heated pool and outdoor kitchen. The value of this home is not only its privacy with exotic landscaping, but its ability to generate income when you are away. Schedule your private showing of The Royal Compound to appreciate the uniqueness of this one-of-a-kind property!

Set against the backdrop of one of Key Wests most prestigious streets, this extraordinary estate is a masterpiece of luxury and refinement, offering an unmatched blend of Palm Beach elegance and Key West historical charm. Moments away from waterfront dining, beaches and tennis and pickleball courts, 1101 Casa Marina Court is a home like no other. With a deeply rooted rich history, this rare property spans half a city block, commanding attention with its vast landscaped grounds,sweeping open spaces, and a stunning pool surrounded by an elaborate courtyard with a meditation garden--ideal for grand entertaining or peaceful relaxation.This estate built was by A. Maitland Adams in the early 1930s, who was said to be a partner of Charles Thomas, Ernest Hemingways fishing companion.If the walls could talk at this iconic residence, it would tell you that this is the very home where renowned author Philip Caputo penned Indian Country and where Gregory Peck and Harry Truman played cards in the dining room. The home features five bedrooms and four and a half bathrooms, including a second-story guest apartment that offers privacy and versatility. Recent updates to the home include travertine marble floors, new roof (2025), high-impact windows and doors, a chefs kitchen, and a welcoming fireplace. Located in the coveted and exclusive Casa Marina neighborhood, this home radiates a sense of timeless elegance and modern luxury. Set on nearly half an acre, this corner estate is the finest of its kind in Key West, offering a lifestyle that is nothing short of spectacular.With every detail thoughtfully curated, this property is a rare opportunity to own a piece of island history, sophistication, and unparalleled beauty.

Nestled in the heart of Key Wests historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern elegant designs. With 5 bedrooms, 5 full baths & 2 half baths, the home spans 4,000sf on a large 12,478sf lot. The 2-story primary home contains the living room, dining room, kitchen, 2 office spaces/dens, one of which could be a bedroom if desired, 2 half baths on the living level & a spectacular 2nd floor primary suite with office/ laundry & an enormous outside covered deck for private lounging. Thoughtful renovations include a stunning glass wall that opens between the outdoor dining pavilion & the top of the line kitchen w/ functional pass-through windows from the kitchen to the pool area. Reclaimed hardwood floors & tall ceilings ensure a perfect balance of historical character & contemporary functionality. The substantial living area, accented by natural light, offers a warm & inviting atmosphere & the gorgeous central pool w/ a water feature creates a stunning outdoor oasis & is perfect for entertaining. Surrounding the pool & outdoor dining pavilion are 2 phenomenal guest houses, housing a total of 4BD/4BA plus a full 1,512sf attic w/ staircase that is built for storage. Lots of off-street parking is offered along w/ a carport & small garage. Everything is new, from the hard wood floors & bathrooms to the salt generated heated pool & generator. This property is a rare offering that combines historical significance, luxurious living & an unbeatable location in one of Key Wests most coveted neighborhoods. Located in the X flood zone just 2 blocks from both Duval St. & the Historic Seaport, it is walkable to all the wonderful restaurants, galleries & shops.

Exclusive opportunity to own one of the largest TRANSIENTLY licensed properties in Old Town Key West. 11 Br, 11Ba, 2 pools, 2 transient licenses, and off street parking for 4+ vehicles. The Watson House is Located centrally on Key Wests most iconic street and only 1 block off Duval street. The Grand Estate is comprised of a 7 Bedroom Mansion and a 4 bedroom Villa. Each home offering a private pool.The mansion was refitted by a local designer in July 2022, including fresh paint and new furniture. Upon entering the mansion you will be greeted with 12 foot soaring ceilings, 2 first floor guest rooms with bath, parlor, living room, dining room and kitchen. The kitchen opens up to a private pool with decking and lounge chairs. A large family style outdoor table is provided for dining al fresco. Heading back inside you will take the Victorian staircase to the second floor. On the second floor you will find 4 bedrooms with en suite baths. The front primary suite offers a private balcony overlooking Simonton Street. A secondary balcony is provided for the rear primary suite overlooking the pool. Take the spiral staircase to the third floor and you will discover a large third floor private suite. Bright and airy the suite provides a living room, wet bar and balcony overlooking the pool. All three floors can also be accessed by exterior and interior staircases. Going back into the parking area, you will take a side entrance to the villa. The villa was renovated to the studs in 2014 with modern and sleek finishes. The villa offers 4 bedrooms and 4 baths, full kitchen, living room, private pool and outdoor bar. The 2 transient licenses give versatility for the property to be rented as an 11 bedroom and 11 bath estate or rented separately as a 7br main house and 4br villa. There are few large estates in Key West, which gives way to its popularity and advance bookings.