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

Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rare opportunity to own a piece of Key West history nestled in one of the islands most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint thats almost unheard of in Old Town, along with the luxury of coveted off-street parking.Step inside to discover a thoughtfully updated interior that blends historic charm with modern comfort. The remodeled bathroom features stylish tilework, updated fixtures, and a spa-like feel, while the upgraded kitchen boasts contemporary cabinetry, sleek countertops, and stainless steel appliances--perfect for preparing everything from a quiet Key West breakfast to tropical cocktails on the patio.Surrounded by lush native foliage, the property offers a serene, private setting just steps from Duval Street, world-class dining, art galleries, entertainment, and more--while maintaining the tranquility of a quiet residential neighborhood.For investors, the unbeatable location just a short stroll from Duval Street, renowned restaurants, nightlife, galleries, and cultural attractions makes this property ideal for monthly vacation rentals or long-term leasing to locals. For second-home buyers, it offers an effortless blend of privacy and proximity to the action, in a quiet residential neighborhood. Truly your home away from home. And for the historic home lover, this residence offers a chance to preserve and personalize a piece of Key Wests architectural heritage with room to enhance over time and make it your own.With its historic architecture, upgraded amenities, and rare lot size, this home offers endless potential to create your tropical dream oasis. Whether youre looking for a charming island retreat, a vacation rental, or a full-time residence, 729 Windsor Lane delivers the perfect blend of location, lifestyle, and opportunity.

Great opportunity to own a single level luxury two bedroom/two bath condo at the exclusive Santa Maria Resort in Old Town Key West. Just steps from Key Wests vibrant downtown scene, this Santa Maria condo also has beach access PLUS a transient rental license with tons of income producing possibilities. This is resort living at its best with beautiful pool and grounds, off street parking and restaurant on site. Make plans to see it today.

This home offers a unique opportunity for flexible living or investment! Currently configured as a single-family residence, it has been approved by the City of Key West to be reverted back to a Multi-family, allowing for up to 4 units. Easily convert the home back to two studios with bath, 1 bedroom 1 bath and a 2 bedroom 1 bath. Welcome to 1409 Truman Avenue, a stunning Key West Eyebrow home that combines historical charm with modern amenities. The spacious layout and design make it easy to transition back to a mult-family configuration of a duplex, triplex or 4 units.. Each potential unit could offer comfortable living spaces, with the square footage allowing for a range of layouts to suit tenants needs.Based on comparable rentals in the area and the square footage of this property, each unit could command an estimated monthly rent of $3k to 6k monthly, each unit (seasonal variables) providing a lucrative investment opportunity. With the strong rental demand in Key West, this property is perfectly positioned to maximize its potential.Whether youre looking to generate income, create a multi-generational living space, or invest in the vibrant Key West market, this property is a rare find. Contact us for more details and to schedule a showing!

Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads directly to the water, offering easy access for boating and water activities. Whether youre a seasoned boater or a weekend enthusiast, this canal-front location provides fantastic opportunities for adventure right at your doorstep.The property offers plenty of storage space, ensuring room for all your gear and toys. Theres even space to add a pool for those sunny Florida days. A garage adds to the convenience, making this home both functional and full of potential.Dont miss the chance to own this piece of paradise, where comfort, coastal living, and a vibrant island lifestyle meet.

Key West Waterfront Retreat - Updated, Spacious & Boater-FriendlyWelcome to your island escape! This beautifully maintained 3-bedroom, 2-bathroom waterfront home offers the best of Key West living, combining modern upgrades, abundant outdoor space, and unbeatable boating access.Situated on a generous lot with an 80-foot seawall, this property is a true boaters dream--just a 10-minute boat ride to the pristine sandbars of Snipes, Marvin Key, and Mudd Key. Whether youre spending the day on the water or relaxing at home, this property provides the perfect balance of relaxation and adventure.Step inside to a bright and open living area, where natural light pours in through all-new impact windows and a new sliding glass door. These upgrades enhance both energy efficiency and storm protection. A new tankless water heater ensures continuous hot water, while a new roof and new A/C system (both installed in 2020) provide comfort and peace of mind.One of the standout features of this home is the covered back patio--the perfect spot to unwind, entertain guests, or enjoy an evening meal while taking in the ocean breeze. The spacious backyard offers ample room to add a pool, giving you the opportunity to create a true backyard oasis.Additional highlights include a covered carport and parking for up to five vehicles, offering plenty of space for guests, boats, or trailers. The home is located in a quiet, desirable neighborhood just minutes from Key Wests vibrant dining, shopping, and cultural attractions.Whether youre looking for a full-time residence, a vacation getaway, or a smart investment, this turnkey waterfront home checks all the boxes for island living with style, comfort, and convenience.

Welcome to 1409 Truman Avenue, a stunning Key West Eyebrow home that combines historical charm with modern amenities. Key Features, Historical Architecture, Enjoy high ceilings, beautiful Dade County Pine throughout, an open staircase, all signature elements of this classic Key West home. Spacious Layout, The home boasts 3 bedrooms one being a large master bedroom with a walk in closet, each with its own en suite bathroom, plus an additional half bath on the first floor. A bonus room on 2nd. floor which can be a 4th. bedroom, office, etc. Modern Kitchen, The kitchen, remodeled in 2019, features ample cabinetry, soapstone countertops, and two wine coolers. Bright and Open Living Spaces: A wall of floor-to-ceiling windows and French doors at the back of the house open onto a covered porch and a shaded yard. Upgrades, The property includes a brand new treated lumber fence on three sides, a whole-house generator, two separate central HVAC systems (4-ton for downstairs and 2-ton for upstairs), two on-demand electric water heaters, a RING home security system, and a CAT 5 network interface module station hardwired throughout. Location, Situated in the desirable Meadows neighborhood, the home is in the X flood zone and has a low portable flood insurance policy (buyer to verify). Its directly across from Bayview Park, offering recreational opportunities. Additional Benefits, Privacy and Security, The fully fenced lot ensures privacy, while the RING security system adds a layer of safety. Climate Control, With two separate HVAC systems, you can efficiently manage the climate on each floor. Neighborhood, The Meadows neighborhood is known for its charming streets and community feel. Being in the X flood zone provides peace of mind re: flood risks, and the proximity to Bayview Park means youll have access to green space, sports facilities, and community events. A short bike ride or walk to Duval St. to enjoy the many nuances that Key West offers.

For the first time, the Key West home of famed landscape architect and Martha Stewart co-star Fernando Wong is available. Welcome to your dream townhouse nestled in the heart of the exclusive Truman Annex, just steps away from the restaurants, shops and bars on Duval Street. This professionally decorated 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern comfort and island charm. As you step inside, youll be greeted by a light-filled open floor plan, featuring a charming living and dining area with tasteful furnishings and a well-appointed kitchen with new appliances. The home features furniture and lighting from Brown Jordan, Ralph Lauren, and Serna & Lilly. Recent renovations include all-new ceiling lights and stylish Legrande light switches and outlets. You will also love the new wood doors, renovated bathrooms, and a recently installed lush jungle landscape. The three beautiful outdoor areas and a strong rental history make this delightful vacation house a once-in-a-lifetime opportunity.

This Jolly Roger Estates treasure puts good times in the Atlantic and back-country waters within easy reach by boat; the owners of this custom-built home will consider all reasonable offers! The 2-story stilt home has exceptional character, multiple inviting porches and outdoor sitting areas. Abundant kitchen cabinets are topped with stunning quartzite counters and a full-length screened porch overlooks the oceanside canal. Designed by the renowned Keys architect, Glenn Gray, the air-conditioned living space totals 1820 sq. ft. on two levels with two bedrooms (one with a porch), one bath, washer and dryer on the main level; the primary bedroom with ensuite bath, his and hers closets, and porch with open water and neighborhood views are on the upper level. An oak staircase in the ground-level foyer connects the three levels. Not to be overlooked are two ground level storage rooms, the garage, an impressive outdoor shower and 60 ft. of canal-frontage for your boat(s). Additional features include Hardie plank siding, metal roof, impact resistant windows on the upper level, solar-assisted water heater, and a 2500-gallon cistern for catching rainwater as a supplemental water source for landscaping and washing vehicles. Make this your piece of Keys paradise!

Step into the laid-back charm of the Florida Keys with this spacious 1,500 sqft home, perfectly situated along a peaceful deep boating canal in the Lower Keys. Located in a tranquil, low-traffic neighborhood, this property offers a serene escape with plenty of room to enjoy life at your own pace.Inside the home: - An open, airy floor plan that allows you to spread out and personalize your living space. - A seamless connection between indoor and outdoor living, making the most of the Florida sunshine. - A private pool right outside the door--ideal for relaxing after a day on the water or enjoying the warm weather with family and friends.For those who love life on the water: - Direct access to deep-water canals, making it easy to get out on the water whenever you like. - A 10,000-pound boat lift to keep your boat safely stored and easily accessible. - Spend your days fishing, cruising, or exploring, and then come home to dock your vessel with ease while soaking in the breathtaking waterfront views.Additional highlights: - A lower enclosure with plenty of storage space for all your outdoor gear, tools, and pool toys, helping keep your home organized and clutter-free. - A newly built home that meets the latest construction standards, offering the added benefit of lower insurance costs and enhanced protection against tropical weather.This home perfectly blends comfort and convenience with the quintessential Florida Keys lifestyle. Whether youre lounging by the pool, boating on the canal, or enjoying the peace and quiet of your surroundings, its the ideal place to call home.Coming Summer 2025 - Please note that the current photos are for reference only, as construction is still in progress. Some design selections may be available for customization. Photos are of model home built by builder and do not fully represent this listing. The seller is a licensed Florida real estate agent.

Solid, Spacious & Ready for Your Island Lifestyle! This 3 BD/3 BA concrete block home is just 3 houses in from Pine Channel, offering quick open water access and a short ride to Looe Key Reef--a world-famous spot for diving, snorkeling, and fishing. The 12,000 lb. boat lift is already installed and hard-wired for safety and convenience.Built Pre-FIRM, the home allows for renovation flexibility and may qualify for lower flood insurance premiums. It also features impact-rated windows and doors, helping you secure some of the lowest possible insurance rates. Wind mitigation and elevation certificates are available.The open-concept great room flows into a chef-inspired kitchen with Cambria quartz countertops, gas cooktop, convection wall oven and microwave, and built-in seating that adds charm and extra storage. With custom cabinetry and generous workspace, this kitchen is both beautiful and functional.Theres ample room and existing architectural plans to add a sleek, modern elevator--ideal for aging in place or added convenience. The home also offers a garage for secure storage and an electric hookup for your RV--a rare bonus for Keys living!Whether youre relaxing inside, entertaining guests, or launching your next boating adventure, this well-maintained, feature-rich home is ready to deliver the best of Big Pine Key living.

Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood.Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from the back door--perfect for unwinding after a day on the water or enjoying sunny Florida afternoons.For boaters, the canal location offers easy water access, along with the convenience of a 10,000-pound boat lift to safely store your boat out of the water. After a day of fishing, cruising, or exploring, dock your vessel with ease and relax as you take in the beautiful waterfront views.The lower enclosure offers abundant storage space for all your tools, pool toys, and outdoor gear, keeping everything organized and clutter-free. Plus, with a newly built home designed to the latest building codes, youll benefit from low insurance rates, ensuring peace of mind and minimized risk from tropical weather.This home offers the ideal combination of comfort, convenience, and the laid-back Florida Keys lifestyle. Dont miss the opportunity to make it yours--schedule your private showing today!COMING SUMMER 2025 - photos of listing do not fully represent dwelling unit, subject to change. Photos are of model home. Construction process underway. Some build selections may be considered. Seller is licensed FL real estate agent.

Step outside to your own slice of paradise - a private oasis that beckons you to unwind and rejuvenate. The sparkling pool, adorned with stunning blue mosaic tiles, creates a mesmerizing focal point, while the soothing sound of its waterfall feature transports you to a world of tranquility. Surrounding the pool, a spacious deck provides the perfect setting for sunbathing, alfresco dining, or simply savoring the tropical ambiance.Lush, verdant landscaping envelops the property, creating a sense of privacy and serenity. Towering palms, vibrant foliage, and colorful flora paint a picture of tropical bliss, making every day feel like a vacation. The covered patio area, complete with comfortable seating, offers a shaded retreat for enjoying your morning coffee or evening cocktails.This property at 1118 Eaton Street isnt just a home; its a lifestyle. Immerse yourself in the laid-back Key West atmosphere, where every day feels like an escape. Whether youre seeking a permanent residence or a dreamy vacation getaway, this charming oasis offers the perfect blend of comfort, style, and island living. Your Key West adventure starts here - seize this opportunity to make your tropical dreams a reality.

At the best location in the heart of old town you will find this great duplex on Julia street in between Duval street and Whitehead street, 86 FOOTSTEPS TO DUVAL STREET. The back is a two bedroom two bathroom with a nice back yard. And in the front is a recently renovated one bedroom with two bathrooms with high ceilings and a great loft. It has an outdoor shower. A new A/C was installed 01/24. When you are sitting on your front porch its hard to believe that you are in between the two busiest streets as Julia street is a really quiet and cute street! Dont miss out on this great opportunity!

MODERN WATERFRONT HIDEAWAY - MOVE IN READY! Drive your boat straight into the Gulf of America. Boaters paradise. Amazing finishes and a vibrant modern interior this 4 bedroom, 2 bath Big Pine Key home will not disappoint. Situated in the peaceful neighborhood of Doctors Arm, within walking distance to No Name Pub and less than 3 minutes to open water (Atlantic through Bogie channel, gulf through Big Spanish channel or access the backcountry) this home is designed exclusively for someone inspiring to live the Florida Keys lifestyle in style. Close attention has been given to the quality of materials used in this recently upgraded home with improvements to include: remodeled kitchen & bathrooms with high-quality HGTV-style finishes, metal roof, life-proof vinyl plank floors, fresh paint, new lights, ceiling fans, and fixtures, updated receptacles and switches, and a new hot water heater. You walk in and it smells like West Elm, like you have been propelled to your own personal oasis. Nothing left to do but move in and start enjoying. For the outdoor enthusiast and fisherman, the property has 2 5,500 lb davits, 60 ft of dockage on a 40ft wide canal, a covered fish cleaning station with electricity and shower, an outdoor fridge, a small bait fridge, and Floating kayak launch. An open-plan kitchen and dining area with plenty of stylish appeal, integrated high-end stainless steel appliances, Thomasville soft close cabinets, quartz countertops with zellige tiles & upgraded fixtures. Four airy, light-filled bedrooms have plenty of storage and closet space and glass doors that open onto composite decking, adding to the feeling of space & openness. This stunning home makes an impact from the minute you lay eyes on it and is in a class of its own. Must make an appointment to view. Please contact agent for showing.

Dont miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of living space. The open-concept layout features a large living room, a well-appointed kitchen with an adjoining dining area, and plenty of natural light. Theres also a garage, laundry room, and potential to easily add a third bedroom.The separate 2-bedroom, 1-bath cottage spans 660 SqFt--perfect for rental income, extended family, or a private guest house.Outside, the expansive yard offers endless possibilities. With plenty of space for a custom patio, outdoor kitchen, or fire pit, its the ideal setup for entertaining, weekend gatherings, or simply enjoying the outdoors. Plenty of parking for multiple vehicles, a boat, or a trailer--perfect for those who need both space and versatility.Whether youre an investor or looking for a multi-generational living solution, this property is packed with potential and ready to make your vision a reality!

Prime Old Town Mixed-Use Property - Live, Work, or Invest! Ideally situated in Old Town Key West, this Historic Residential Office (HRO) zoned property offers a rare opportunity for both residential and commercial use. Previously, home to a successful spa, its perfectly suited for continuing as a business or transforming into a private residence. Filled with character, the space features stunning Dade County Pine walls, adding warmth and historic charm. The layout includes a one-bedroom apartment with a private rear entrance, making it ideal for someone who wants to run a business in the front while living on-site or creating an additional rental opportunity. One interesting piece of history was that this building was previously owned by a well known attorney here in Key West by the name of Helio Gomez. He served as Judge from 1963 to 1977 and he was the attorney for the infamous John Bum Farto. Located just one block from Duval Street, two blocks from the Hemingway House, and steps from the courthouse, this property offers prime visibility and accessibility. Whether youre an entrepreneur looking for a turnkey business location, an investor seeking a valuable addition to your portfolio, or a homeowner ready to bring your vision to life, this space is full of possibilities. Dont miss this chance to own a piece of Key West history in an unbeatable location. Note: This property is currently configured as a commercial space with 1 bedroom but has the potential to expand to up to a total of four bedrooms, pending submission and approval of all applicable permits with the City. Any future development or expansion must comply with all relevant sections of the Land Development Regulations, including meeting the definition of a single-family home and avoiding any conflicts with the definitions or restrictions related to lockout units.

NEW LISTING! Fantastic Key West location in the heart of Old Town Key West. Close to famous Duval Street, Historic Seaport, fine dining, galleries and more. Spacious two story home with 2,080 sq ft of living space. Three bedrooms and three full baths. Fenced yard. Patio Space. French Doors. Lanai area.

Tropical charm, flexible living, and a fantastic location--welcome to 2109 Seidenberg Avenue in the heart of Key Wests New Town. This updated 3-bedroom, 2-bath home includes a separate, fully equipped guest cottage--perfect for visiting friends and family or as a private space for extended stays.From the moment you arrive, youll feel the laid-back island vibe. Light flows through the homes open and airy layout, accented by beautiful hardwood floors and a remodeled kitchen with stainless steel appliances. The main home invites relaxation, while the tropical landscaping, mango tree, and welcoming front and back porches make enjoying island life a breeze.Enjoy peace of mind with hurricane impact windows and doors, plus a brand-new roof completed in July 2024. The low-maintenance turf front yard keeps things clean and green all year round, and the detached garage adds extra storage or parking flexibility.Whether youre looking for a primary residence, tropical retreat, or a Key West home with guest space built in, 2109 Seidenberg delivers. Just minutes from beaches, schools, shopping, and all the fun the island has to offer. The home comes fully furnished (minus a few personal paintings), so you can settle in and start enjoying island life from day one.

Enjoy absolutely stunning open water views and spectacular sunrises every morning from this gorgeous open waterfront property in Tropical Bay Estates. This spacious 3-bedroom, 2-bath home was completely remodeled in 2020 with beautiful finishes throughout. Enjoy a chefs kitchen, with top of the line appliances, and an abundance of cabinets and counter space, ideal for entertaining. Flooded with natural light, this gorgeous layout was designed to capture breathtaking views of the open water from every angle in the main living area, a tranquil backdrop, perfect for any occasion. Enjoy peace of mind with all new plumbing and all new updated electrical throughout. The concrete block construction with impact windows, metal roof, and foamed roof deck insulation, make this home an absolute fortress. Situated on Bogie Channel with excellent boating access to both the Atlantic and Gulf where you can enjoy world class fishing and diving in only a short run. You are also just around the bend by boat or car, from Bahia Honda State Park voted one of the best beaches in the U.S by Trip Advisor.

Welcome to 1911 Fogarty Avenue -- a beautifully updated Key West bungalow that masterfully blends historic island character with modern-day comfort. This 2-bedroom, 2-bath home is full of classic Key West craftsmanship, featuring original Dade County pine throughout and gracefully arched cove ceilings that bring warmth and elegance to every room.The remodeled kitchen is a chefs delight with custom cabinetry, granite countertops, stainless steel appliances, and stylish finishes that echo the homes vintage soul. French doors open from the kitchen inviting the outside in. Both bathrooms have been tastefully updated with clean, coastal design and high-quality fixtures.Step outside into your own private tropical sanctuary. The fully fenced backyard features lush landscaping, a spacious sun TREK deck, and a sparkling heated saltwater pool with a tranquil water feature. Entertain in style with a built-in outdoor kitchen and unwind under the palms with an outdoor shower -- perfect after a dip in the pool or a day at the beach. A separate pool house offers additional flexible space for guests, a home office, art studio, or personal retreat.Additional features include off-street parking, a den/study, and plenty of room for lounging, dining, or simply enjoying the laid-back Key West lifestyle.Centrally located in a quiet, established neighborhood, this home is just minutes from Old Town, beaches, local shops and restaurants. A rare and move-in ready slice of Key West living is waiting for you at 1911 Fogarty Avenue -- dont miss it!