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

711 Olivia Street is a rare gem that fuses timeless Conch-style architecture with sophisticated, modern upgrades. This 3-bed, 3-bath home has been meticulously remodeled, creating a private sanctuary that honors its historic heritage while offering all the comforts of -contemporary living. The open-concept layout welcomes you with premium flooring & abundant natural light, all designed to enhance the seamless flow between indoor and outdoor spaces. At the center of the home is a beautifully appointed gourmet kitchen equipped with high-end appliances, a gas range, expansive counters, and custom cabinetry.Significant enhancements have been made with no detail overlooked. All windows, French doors, and sliders have been upgraded to hurricane-rated impact glass, while the original HARC-protected front windows remain beautifully preserved with hurricane shutters for protection. The roof is securely tied to the structure and treated with a specialized coating that reflects heat and seals out humidity. The outdoor space is a lush tropical retreat, surrounded by professionally designed landscaping featuring mature palms & vibrant orchids supported by an irrigation system. A heated pool with updated plumbing and a new pump invites you to relax in style, complete with a spacious deck and an outdoor kitchen. Further upgrades include spray foam insulation beneath the main home and throughout the pool house to enhance energy efficiency & guard against moisture. New AC units provide reliable comfort year-round. Smart home technology, a security system, and ductless climate control elevate the living experience with comfort & peace of mind. Situated on a 3,350 sq. ft. lot in the highly desirable X flood zone, this home also offers the rare advantage of off-street parking. More than just a home--its a refined blend of historic charm and luxury living in one of Key Wests most coveted neighborhoods.

This mid-town multi-family home offers a remarkable living experience. Designed for comfort and privacy, it features 2 distinct apartments, each w/its own charm & functionality & it can become a 30 day vacation rental w/appropriate licensing. Downstairs: 2 spacious bedrooms & 2 well-appointed bathrooms. The Master has a walk-in closet system, a built-in office; the large Master bath a spacious shower. Open concept Living room/Kitchen features Pantry, quartz counter tops, built-in wine cooler, all overlooking the pool w/ water feature crafted by the renown Master Potter Jay Gogin. A guest suite w/private bath/entrance offers additional privacy & convenience. Upstairs: 3 bedroom/2 bath layout w/Master featuring built-in space saving mirrored closet & ensuite bath. French doors & balconies overlook the backyard foliage & pool. The 2nd remodeled bathroom services the 2 bedrooms, 1 of which is used as a media room. The open Living room/Kitchen has built-in wall shelves, w/ the Washer/dryer located in the hallway. The property is private; saltwater pool can be heated or chilled, it has unique bamboo fencing, & an elevated patio in front overlooking the street. Whole house Generac generator, large Rheem on-demand gas tankless water heater, metal roof, accordion storm shutters, & 3 off-street parking places round out this independent living experience.

Step inside 1511 South Street -- a fully reimagined Key West residence where modern design and island living come together in a private tropical oasis. Completed renovations in 2024/2025 have transformed both the main house and guest cottage into thoughtfully curated spaces with high-end finishes and effortless indoor-outdoor flow. Behind the gate, youll find a lush, low-maintenance landscape and multiple updated outdoor entertaining areas, perfect for gatherings or quiet relaxation. Complete privacy surrounds the property, allowing you to enjoy the serenity of island life just moments from the heart of Key West. Inside the main house, vaulted ceilings and an open-concept layout create a sense of space and light, with every room offering access to the outdoors through its own impact-rated door. The living, dining, and kitchen areas connect seamlessly, with a commercial-style kitchen featuring open shelving, high-end appliances, and direct access to the covered carport--ideal for everyday convenience. French doors open to an 18 x 14 Caribbean-inspired loggia and a custom outdoor kitchen by Paradise Grills, perfectly positioned alongside the heated pool. Surrounded by new stonework and low-maintenance WEARDECK composite decking, the pool area is just one of several outdoor spaces designed to make entertaining effortless. Each of the main houses bedrooms opens directly to the pool, while the large laundry room provides additional storage and functionality. Just beyond the pool, the two-story guest cottage offers flexibility and comfort, with a bedroom and bathroom on each level, generous walk-in closets, and a dedicated generator for added peace of mind. Additional features include multiple outdoor storage closets, an air-conditioned attic above the carport, and a canvas-covered rear yard that expands your living space even further. Understated from the street, yet unforgettable once inside--this property is a private retreat designed for the best of Key West living.

BRAND NEW CBS Construction ready for occupancy!!! Amazing New Oceanside Home with 4 Bedrooms, 3.5 Baths, in Beautiful Cudjoe Ocean Shores, (Custom Built by Dream Builders of the Florida Keys). This home offers Open Water Views, Instant Deep Draft Boating for Big Boat Action, Protected Concrete step-down Dock, Open Floor plan, Dining Area, two Master Suites, High Ceilings, Chefs Kitchen with high end finishes, Stainless Steel Appliances, Quartz Counter Tops, Kitchen Island and Designer Lighting. Custom Bathrooms with Tiled Baths, Seated Showers, California Closets, Aqua Guard (waterproof) Performance Wood Based Flooring, Solar System, Custom Concrete Pool with Pebble Tech Finish, Pool Heater and Chiller, Master Bedroom Balcony and Direct Atlantic Ocean access. This home is spacious with over 1900 sq/ft under air, covered porch with Open Water Views, Impact Doors and Windows, Metal Roof, Concrete Storage Room Downstairs ( with Impact windows), Two Tiled Exterior Stair Cases for easy access, Custom Paver Driveway, AE flood zone, Tropical Landscaping by Trees R Us with a beautiful artificial turf lounging area and more. This is a rare find in the Florida Keys...bring the big boat and toys!!! Landscaping and Artificial Turf will be completed by 4/25/25. Easy to show...dont miss this gem! Easy and fun to show call listing agent for showings.

Second floor Harbour Place condominium features 2 bedrooms and 2.5 baths. Relax on your private balcony and admire the beautiful sunsets and views of the ocean, gulf and all the activity in Key West harbor. Recently updated, this beautiful property is move-in ready and has spectacular views from the large windows and both bedrooms. Easily accessible by the conveniently located elevator. One of the few Harbour Place units with 2 parking spaces, #15 and 16. Video Tour: https://show.tours/v/4MqLYGD

This town house is in the award-winning Truman Annex and is located on a private lane surrounded by charming custom-built homes. The generous open floor plan features 10-foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with quartz countertops and stainless-steel appliances with a gas cook top. The large living and dining area feature custom built-ins and ample storage. The beautiful rear tiled patio enjoys ample room for outdoor living & entertaining and includes additional storage space. The 2nd floor has two generous size bedrooms with private baths. Impact rated windows and doors. Includes the special Truman Annex transient rental license with restrictions.

Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units, each offering great rental income potential. Your chance to make money and have a home in paradise. Newly remodeled kitchen in the rental home.Enjoy the large inviting pool and well-maintained grounds, all just minutes from downtown Key West. Whether youre looking for a lucrative rental property or a versatile family compound, this unique property is a perfect choice. Dont miss your chance to own this gem in the heart of Key West! Prime Corner Lot enjoy the benefits of a corner lot with enhanced privacy and curb appeal.The property has ample parking and features a three-vehicle covered carport, along with additional off-street parking that can accommodate your boat or RV.The layout and landscaping provide a sense of seclusion, ensuring a comfortable living experience for tenants.This multi-family property is a rare find, combining practicality, privacy, and profitability. Dont miss out on this outstanding investment opportunity!

CALLING ALL INVESTORS!! Excellent income producing rental property or employee housing with multiple units. All apartments are currently rented at below market rents. With its downtown location, low flood risk, turn-key income, and transient receivership zone, this property is perfectly positioned for savvy investors. Three 1bed 1bath units, One 2 bed 1 bath separate cottage. One studio. Please note that advanced notice is required to arrange showings, and not all units may be available for viewing as they are currently rented.No sign on property

Dona Calabash - Located just a half a block from the upper end of Duval Street this charming Old Town beauty has it all! Three bedrooms including a luxurious master suite with spa bath, two guest bedrooms and two full baths. The gourmet kitchen features commercial grade stainless appliances, granite countertops and plenty of storage. Rear French doors open to a covered deck and the refreshing pool and surrounding lush gardens. The adjacent cabana house has a beautifully appointed bath and cozy sleeping/sitting area. Features here also include high ceilings, hardwood Brazilian cherry floors, Dade County pine feature walls, gorgeous grounds and a convenient electric gate for the off street parking for multiple vehicles. This property has been meticulously designed and maintained for the discerning new owners! Walking distance to the ocean, restaurants, shops and nightlife and still have privacy & quiet, this special fully appointed property is a must see.! Very easy to show!

Epitome of Paradise!There is an enveloping comfort, an ease and repose, that beckons one away from the worlds cares and invites one to lounge, drift away, and dream in this gorgeous waterfront condominium.Enjoy a single level open floor plan with two bedrooms, two full baths and a convenient powder room.Exquisitely decorated to reflect the local island flavor with all new furniture and furnishings, just bring your favorite book!There are several quiet places to sit back and enjoy which includes a breathtaking wrap around deck with views of the inner harbor, the Ocean, Sunset Key, and beyond. The adjacent covered dining area is perfect for those opportunities to sip, dine and dream while embracing the light, the climate, the trade winds, The waterfront heated pool complex boasts of breathtaking views from dawn to dusk! There is also a covered assigned parking space, #23, a full time security team and a true gated community experience with close proximity to the local park, Duval Street and the local nightlife!

Gorgeous tropical gardens greet you to this enchanting home in the coveted Casa Marina neighborhood. Enjoy a spacious 3 beds/ 2.5 baths with pool and off-street parking. While the home is complete with all the amenities one would expect in an island home the improvements are intentionally simple yet thoughtful to preserve its vintage charm. Through the front door you will be welcomed to a spacious sitting room that can adapt to your personal needs as a generous bonus space. Just past the two guest rooms with shared bath you will find a striking greatroom with soaring 2 story ceiling heights that flood the room with natural light. Enjoy the open yet dedicated dining room and a delightful petite kitchen that overlooks the pool and back gardens. The upstairs is reserved for the primary suite alone and boasts a unique balcony overlooking the great room for a spacious open and airy feel. Thoughtful improvements carry to the outside with low maintenance composite decking, full exterior paint just completed and storage for your extras. Come take a look at this gracious home awaiting someone to adore its thoughtful preservations and authentic charm.

If you are looking for location and a historic home, this triplex is tucked away on one of Old Town Key Wests most peaceful lanes. This charming Conch home won the distinguished Historic Florida Keys Preservation Star in 1988 and has been in the same family for over 40 years--a true testament to its warmth, character, and enduring appeal.The main house features generously sized rooms, high ceilings, and Dade County pine walls, all beautifully restored by local craftsmen.Attached to the main house is a versatile studio apartment, originally part of the homes original footprint and easily convertible back into a grand primary suite. In addition, there is a detached studio cottage perfect for guests or additional income.Part of the historic preservation focused on the large wraparound front porch with delicate gingerbread trim. The original water cistern was turned into a pool. This residence is a living piece of Key Wests vibrant history. Jimmy Buffett used to live next door for some time writing his book and songs.Now available as part of an estate sale, dont miss your opportunity to be the next steward of this extraordinary legacy.

Embrace the unique opportunity for eco-friendly Key West living, with significantly reduced electric bills. The solar panel system, installed by Salt Air, features 39 high-efficiency solar modules, each delivering 327 watts, for a total capacity of 12.75 kilowatts. Designed for low maintenance, this system is fully covered under warranty for your peace of mind. The system is upgraded to ensure that panels unaffected by shading continue to generate power efficiently. It charges and stores the energy produced, and once fully charged, it sells any excess energy back to Keys Energy. This exceptional one level home features expansive impact windows and sliding glass doors, seamlessly blending indoor and outdoor spaces. The fully-equipped kitchen, anchored by a spacious eat-in island, is perfect for intimate dinners or hosting grand soirees.Step into the master bedroom, where sliding doors lead to your tranquil swimming pool and a private ensuite bathroom. Adjacent to the master suite, a convenient half-bath, and a versatile office space that could serve as an additional living space or extension to your master suite. The guest wing includes two bedrooms sharing a bath, along with a charming outside guest cottage complete with a full bathroom--ideal for a guest suite, gym, or art studio.Nestled in the coveted Midtown neighborhood, this home is just a short bike ride from Old Town and mere moments from Higgs Beach and White Street Pier. Dont miss the chance to experience this distinctive Key West gem, where modern luxury and sustainable living

If you are looking for location and a historic home, this wonderful home is tucked away on one of Old Town Key Wests most peaceful lanes. This charming Conch home won the distinguished Historic Florida Keys Preservation Star in 1988 and has been in the same family for over 40 years--a true testament to its warmth, character, and enduring appeal. The main house features generously sized rooms, high ceilings, and Dade County pine walls, all beautifully restored by local craftsmen. Attached to the main house is a versatile studio apartment, originally part of the homes original footprint and easily convertible back into a grand primary suite. In addition, there is a detached studio cottage perfect for guests or additional income. Part of the historic preservation focused on the large wraparound front porch with delicate gingerbread trim. The original water cistern was turned into a pool. This residence is a living piece of Key Wests vibrant history. Jimmy Buffett used to live next door for some time writing his book and songs. Now available as part of an estate sale, dont miss your opportunity to be the next steward of this extraordinary legacy.

Step into a piece of history, reimagined for modern luxury. This stunning 3-bedroom, 3-bath condominium is located in the historic Naval Administration Building within the prestigious, award-winning Truman Annex. Completely renovated to the highest contemporary standards, this one-of-a-kind residence boasts soaring exposed beam ceilings, ultra-thick concrete walls and ceilings for unparalleled privacy, and top-tier hurricane protection with impact glass doors and windows--high and dry for any storm. Every inch of this home is designed for effortless living, featuring a state-of-the-art smart house system controlled by iPad or remote, allowing you to adjust lighting, climate, blinds, and music with a tap. A dedicated server room houses a professional-grade electronics rack, ensuring seamless connectivity. The chefs kitchen is a masterpiece, showcasing high-end Miele stainless steel appliances, illuminated white onyx countertops, and LED accent lighting that shifts from white to multicolor to suit any mood.Luxury extends throughout, with custom-built furnishings and designer decor from a top South Florida designer included. Flor to ceiling porcelain tile bathrooms, elegant wall treatments, and expansive closet storage elevate the living experience. Motorized sheer shades throughout add a touch of sophistication, with additional smart blackout shades in the bedrooms. Edge-lit LED grid ceiling lights complete the sleek, modern aesthetic. The unit offers unparalleled views of Trumans Little White house, gardens, and his 1949 Lincoln Limousine. Harbor Place condominiums overlook Key West harbor with exquisite Ocean views and heated pool. This is not just a home--its a rare fusion of historic charm and cutting-edge innovation, set in Key Wests most exclusive gated community. Dont miss your opportunity to own a true showpiece in the heart of Truman Annex! Eligible for the special Truman Annex vacation rental license.

Prime Mixed-Use Investment Opportunity in Key West!Built in 2021 to current building codes, this exceptional four-unit commercial and residential compound is a rare find in the heart of Key West. A perfect 1031 Exchange candidate, this versatile property includes two licensed townhouse residences and two licensed commercial units, offering excellent income potential and flexibility.The commercial building, positioned street-side, is a two-story frame structure with high visibility on Truman Avenue. The ground floor offers approximately 1,112 square feet of open commercial space, while the second floor spans approximately 800 square feet and features a 30-foot-wide balcony overlooking Truman Avenue. An ADA-compliant elevator provides easy access to the second floor. Both levels include fully ADA-compliant restrooms, nine-foot-high ceilings, recessed lighting, ceiling fans, central air conditioning, washer and dryer hookups, and are pre-wired and plumbed for refrigerators and sinks. At the rear of the property, the residential portion consists of a two-story, common-wall duplex, with each unit offering approximately 1,015 square feet of living space. Designed for comfort and style, each unit features two bedrooms and two and a half bathrooms, vaulted ceilings in the upstairs bedrooms, spacious island kitchens, tile flooring, and private shaded rear decks. The property is thoughtfully designed with a beautifully landscaped common courtyard that separates the commercial and residential buildings, enhancing privacy and curb appeal. This turnkey mixed-use property presents a rare opportunity to own a high-quality, income-producing asset in one of Key Wests most desirable locations. Dont miss out on this exceptional investment! *Note: 3D Tour is only of the 2 residential units.*

Open Water, Elevated, Concrete Home in best Waterfront community with easy proximity to Key West. 117 Key Haven Road was built to stand the test of time. With its Elevated concrete construction, metal roof and impact windows and doors, this home offers excellent protection of your investment and safety for your family and high quality comfort.Its combination of large 9300 sq ft. lot, excellent deep water access and stunning open water views of the bay and Gulf of Mexico make this an amazing opportunity for the buyer looking for a waterfront home.Configured as a 3BD/2BA, all on one elevated level with master suite and wrap around balcony overlooking the open water.Renovated kitchen with stainless steel appliances and beautiful granite countertops provides excellent space to prepare and enjoy a dining experience.Two separate single car garages offer ample storage, additional off-street parking and boat trailer parking also available.Large concrete deck in the rear offers many options to those who love to entertain and enjoy the outdoors. Plenty of room for a pool and property can accommodate multiple boats.

Luxury Waterfront Fortress with Breathtaking Atlantic Ocean Views. Experience unparalleled coastal living with stunning, unobstructed views of the Atlantic Ocean and Kemp Channel from this oversized 12,000 sq. ft. corner lot. This one-of-a-kind CBS home is built for strength and style, offering the ultimate in durability and design. Featuring 4 bedrooms, 3 baths, and a spacious two-car garage, the home is elevated for maximum protection--perfect for safeguarding vehicles, marine toys, and personal gear. A top-of-the-line elevator provides seamless access, large chefs kitchen, impact-resistant windows and doors, a newer roof, fresh paint and lush landscaping with fruit bearing trees. Boating enthusiasts will love the 193 feet of direct waterfront, including 105 feet of deep, protected canal-front concrete dockage and davits, providing effortless access to Kemp Channel, the Gulf, and the Atlantic Ocean. Privacy is paramount with a fully fenced, elevated lot, an electric gated entrance, and a dual concrete driveway. Dont miss this rare opportunity to own a fortress of elegance and strength in one of the most sought-after waterfront locations. Schedule your private showing today!

This stunning Florida ranch-style home has been completely remodeled to offer a blend of modern luxury and comfortable living. From the moment you step inside, youll be captivated by the expansive open floor plan, which creates a seamless flow between the living spaces, ideal for both everyday living and entertaining.The heart of the home is the chefs kitchen, featuring high-end Cafe appliances with elegant bronze finishes, ensuring both style and functionality for any culinary enthusiast. Whether youre preparing a gourmet meal or enjoying a casual breakfast, the spacious layout offers ample room and top-of-the-line finishes that elevate the entire space.With four generously-sized bedrooms and three and a half baths, this home offers the perfect balance of privacy and shared space. Each bathroom is meticulously updated, offering sleek, modern fixtures and luxurious finishes. The master suite is an oasis of tranquility, complete with a spa-like ensuite bath designed for relaxation.Every detail of this home has been thoughtfully updated, including all new electric and plumbing systems, ensuring both convenience and peace of mind. The entire property is protected with brand-new impact-resistant glass, adding security and energy efficiency to the already impressive home.The oversized corner lot offers privacy and plenty of room for outdoor activities. The new in-ground pool is an entertainers dream, providing a private retreat where you can relax and soak in the Florida sunshine. The massive back porch is perfect for hosting gatherings, with ample seating under the cool breeze of ceiling fans. The space is designed with tropical landscaping, creating a lush, serene environment that enhances the homes connection to nature.This home combines the best of modern design with the timeless charm of its original style. With meticulous attention to detail and a perfect blend of indoor and outdoor living spaces.

Indulge in the pinnacle of luxury at this stunning three-story Old Town Key West residence, a property that simply must be seen. Located directly across from the historic Key West Lighthouse and just steps from the renowned Duval Street, this home offers unparalleled access to Key Wests finest attractions. A leisurely stroll takes you to the Southernmost Point and the Atlantic Ocean, mere minutes away. Located in the coveted X Flood Zone, one of Key Wests highest elevation points and boasting over 3,000 square feet of meticulously designed living space, including four bedrooms and four bathrooms featuring two master suites, this home effortlessly blends sophistication with contemporary comfort. The first floor showcases a generous eat-in kitchen, a versatile guest bedroom or sitting room, and two full bathrooms, while the expansive great room provides an ideal retreat for relaxation or entertainment. French doors open to reveal a spacious in-ground pool, perfect for enjoying refreshing breezes and ample outdoor space. The second and third floors house two additional master suites, each offering privacy and opulence. Embrace a lifestyle of refinement and coastal allure in this exclusive Key West haven. Ideally situated for walking or biking to renowned restaurants, enjoying live music, exploring galleries, spending the day at Fort Zachary Taylor State Park or savoring the vibrant energy of Duval Street.