Lower Keys Homes for Sale, Single Family Houses, MLS Home Listings

Step into the charm of this beautifully designed two-story Conch home, originally built in 1923 and thoughtfully expanded to offer the perfect amount of space.The historic character shines through with rare Dade County pine walls, while the open floor plan, Birch hardwood floors, and soaring 10-foot ceilings create a bright and inviting space. The kitchen is a chefs dream, featuring stainless steel appliances and an oversized split farmhouse sink. This home offers three ensuite bedrooms, each providing comfort and privacy.Step outside to enjoy the stunning Ipe wood decking, perfect for relaxing or entertaining. The newer heated and chilled pool is ideal for year-round enjoyment, whether youre cooling off in the summer or warming up on cooler nights.And you cant beat the location! Just one block from world-famous Duval Street and a few blocks from the Southernmost Point, this home puts you right in the heart of Key West. Stroll to galleries, dine at amazing restaurants, and enjoy some of the best local music in town--all just a short walk from your front door.Not only is this home perfect for personal use, but its also in a fantastic area for an investment property. With its prime location and desirable features, it has great potential for rental income.This home blends history with modern comfort--dont miss the chance to make it yours!

This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325 of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180 deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens to the Chefs Kitchen enhanced with sleek white cabinetry, stainless steel appliances, gas range, wall oven, walk-in pantry and center island for friends and family to gather around. The first floor is also home to a Guest Bedroom and Bath and the Primary Suite featuring a large bathroom, walk-in closet and direct access to the large screened veranda overlooking the water. The 2nd story offers an ensuite Guest Bedroom and Office/Den plus a Porch with amazing 360 degree sunrise to sunset views. Plenty of room for all off your toys with 1,450 sq. ft. of Garage and storage. The 2 additional adjoining lots is the perfect place for a pool, RV and accessories and ensures complete privacy. Storm ready with impact doors and windows and metal roof. Jolly Roger Estates is a small coastal community of waterfront homes just minutes to dining and shopping and the magic of Key West less than 30 minutes away.

Escape to your own slice of paradise at this Oceanfront retreat on the breathtaking shores of Big Pine Key. Perfectly situated on a 1/2-acre beachfront lot, this stunning home offers a rare blend of tranquility, elegance, and natural beauty. From unmatched sunrise to sunset views to the private sandy beach, this residence is the ultimate Florida Keys oasis. Step inside and be captivated by the expansive great room, featuring vaulted ceilings and a soaring 20 coral fireplace that serves as a dramatic focal point. Natural light floods the space, creating a warm and inviting atmosphere that seamlessly blends indoor and outdoor living. The spacious screened porch features a wet bar and provides the perfect vantage point to savor the coastal breeze while taking in the panoramic views of the Ocean. The split floor plan ensures privacy and comfort, with two generously sized bedrooms sharing an updated bathroom adorned with custom tile work. The primary suite is a true sanctuary, offering sweeping ocean views, a spa-like en-suite bathroom, and a walk-in closet. An additional loft space overlooks the great room, making it an ideal spot for a home office, reading nook, or a 4th bedroom. Designed for entertaining, the chefs kitchen boasts a large center island perfect for meal prep or hosting large gatherings. Outfitted with stainless steel appliances, this kitchen is a culinary dream come true. The outdoor living experience is unparalleled, with a rooftop deck perfect for sunbathing by day and stargazing by night. The private sandy beach and quiet neighborhood, home to the beloved Key Deer, provide an idyllic backdrop for relaxation. Built for peace of mind, this home features CBS construction, a standing seam metal roof, and a whole-house generator, ensuring safety and convenience year round. Whether youre looking to entertain guests, escape the hustle and bustle, or simply soak in the beauty of the Florida Keys, this retreat captures the essence of true coastal living!

Renovated, highest quality. New heated pool, ipe deck, new metal shingle roof, entire two bedroom is brand new.6,254 square feet of land, corner lot, park your RV, add guest house, etc. Two on site parking spaces. Home was renovated to convert to single family, currently set up as two units, one two bedroom, two bath with large sleeping loft and a one bedroom, one bath, (two legal units). Both floor plans attached, as is and the proposed conversion to single family. Tennis courts across the street. Keep as is and rent one side or easily finish conversion to single family. Room for your RV on the very large fenced lot. Current owners are licensed Florida Realtors.

LOCATION! LOCATION! LOCATION! You do not want to miss out on the opportunity to own one of the most sought after properties in Old Town Key West, a truly special home and lot that you MUST see in person. Permitted for transient license receivership HRCC1 (buyer to verify). The ONLY single family home on the market with DIRECT access to DUVAL Street via a walking lane. Remarkably secluded and completely hidden from view. The moment you step behind the gate, you will feel that you have entered your own tropical paradise. Add a pool and expand on this beautiful 4200 square foot lot. Zoned as a non contributing structure with HARC (buyer to verify), this is a restoration project. This is the first time the property has ever been on the market!

INVESTOR ALERT! Great opportunity to own a 3 unit building centrally located in Key West with off Street parking and plenty of room for a pool. The downstairs front unit is a 2BD/1BA, has an open floor plan with lots of windows allowing for plenty of natural light and a cute front porch. The upstairs unit is a 1BD/1BA and the rear third unit is another 2BD/1BA. The multi unit building sits on a nearly 4,000sf corner lot, consists of 2 structures and has just over 2,000sf of total living space. Located only a few blocks to Duval Street, the beaches, wonderful restaurants and many more of Key West attractions! Tenant occupied, minimum 24 Hour notice to show.

Effortless style, prime location, and outdoor living at its best. Welcome to your dream coastal beach cottage, tucked away in a quiet midtown neighborhood. This completely updated one-level home offers the perfect combination of privacy, convenience, and island charm. Just minutes from the beach and walkable or bikeable to Key Wests best restaurants and cafes, 1619 Rose Street is perfectly situated to embrace the ultimate island lifestyle.Step into a thoughtfully designed home with an open floor plan that flows seamlessly from the living area to the dining room, kitchen, and out to the expansive lanai. The master suite is a true retreat, with sliding glass doors opening directly to the pool area, a walk-through shower, and a custom-fitted walk-in closet.The centerpiece of this home is the lushly landscaped backyard oasis. Surrounded by tropical greenery, it features a heated pool, multiple outdoor living spaces, and a serene ambiance perfect for relaxing or entertaining. Completing this outdoor paradise is a detached one-bedroom, one-bath guest cottage with its own private deck overlooking the heated and chilled pool--ideal for visitors or a private home office.Modern design, thoughtful details, and the very best of Key West living await you in this stunning island retreat. Being sold furnished excluding artwork.

Located in the prestigious gated Truman Annex, this beautifully appointed 2-bedroom, 2.5-bath home offers refined coastal living just steps from Duval Street and Truman Waterfront. Thoughtfully designed with elegant finishes and an open, airy layout, this residence is perfect for those seeking a private sanctuary in Old Town.A private entrance welcomes you into a turn-key interior, where Serena & Lily accents and carefully curated decor create a sophisticated yet relaxed atmosphere. The kitchen features Bosch stainless steel appliances, an induction oven, a farmhouse sink, and a waterfall-edge peninsula with bar seating. The open-concept dining and living areas are designed for both comfort and style, with striking furnishings, a large wall-mounted TV, and plenty of space for entertaining. Two sets of French doors lead to a private, lushly landscaped patio, offering a peaceful retreat for outdoor dining and relaxation. A first-floor powder room adds convenience.Upstairs, 2 bedrooms each with a king size bed provide a luxurious escape. The primary suite boasts French doors opening to a covered balcony, perfect for enjoying the island breeze. The ensuite bath features dual sinks, waterfall faucets, and a beautifully tiled walk-in shower. Down the hall, the second bedroom is a tranquil retreat with ample closet space and access to a hall bath with a walk-in shower.The outdoor space is designed for year-round enjoyment, with a fully fenced paver patio, seating, and a grill. Just a short walk away, the heated community pool offers lounge chairs, shaded tables, and restroom facilities. A designated parking space is conveniently located just steps from the home.216 Fleming Street is just mere blocks away from world-class dining, shopping, and entertainment. This home presently has a transient license and future bookings through 2025 in place. Whether youre looking for a full-time residence, a vacation home, or an investment opportunity, this home offers it all.

Tucked away on one of Key Wests most private and secluded streets--seriously, if youve never been to 913 Watson Street, youve probably never been on this block--this meticulously reimagined historic home, built prior to 1912, is the epitome of island living. Located in the coveted Old Town neighborhood and Key Wests highest elevation (X-500 Flood Zone), this property seamlessly blends historic charm with modern conveniences. Every inch of this residence, completed in April 2025, has been thoughtfully revitalized with no expense spared. Were talking historic-approved impact-rated windows and sliding doors, a brand-new roof, plumbing, electrical, HVAC, and foundation piers, plus gleaming hardwood floors. Step inside the main house, where youll find a bright and airy one-bedroom, 1.5-bath layout featuring a stylish kitchen with all-new appliances, a dedicated laundry room, and tranquil garden and pool views. Oversized sliding doors blur the lines between indoor and outdoor living, leading you to a serene outdoor space complete with a saltwater cocktail pool, water feature, and composite decking--ideal for al fresco dining, lounging, or simply enjoying the tropical ambiance. Directly across from the main home is the separate guest house, which could serve as a second full bedroom or a spacious living room. This versatile space includes a large walk-in closet, en-suite bathroom, and tranquil pool views, offering both comfort and privacy. The property also features a large carport, offering ample space for parking. And lets talk location--walking and biking distance to Key Wests top restaurants, nightlife, and beaches, yet nestled on a street so private, it feels like a secret.

A true Historic Gem, meticulously restored to its former glory with a complete, ground-up revitalization. Every detail has been thoughtfully preserved and reimagined, blending timeless character with modern craftsmanship to create a stunning masterpiece that honors the past while embracing the future.Experience the ease and elegance of one-level living in this Island Inspired Retreat. This tropical haven features two impeccably styled bedrooms, each with its own Spa-like en-suite and spacious closets for effortless organization. Accent wood wall finishes add warmth and character while the hand selected tropical wallpaper, infuses each space with a vibrant, vacation-like ambiance.The Charming finished half-story on the second floor is a dream hideaway designed for fun, comfort and unforgettable memories. This inviting space features four built-in bunks, creating a cozy camp-like retreat thats perfect for grandkids, visiting family or extra guests.Each bunk is adorned with luxurious hand-selected linens, making it as stylish as it is comfortable. Whether its laughter-filled sleepovers or quiet afternoon naps, this whimsical bunk room promises to be a favorite spots for guests of all ages. The Spacious, thoughtfully designed kitchen is a gathering place for making memories, perfect for hosting family, friends and special occasions. The oversized island offers plenty of space for meal prep, casual dining or simply enjoying a cup of coffee while chatting with loved ones. From the Kitchen, youll enjoy the picturesque views of the beautifully appointed tropical living and dining area, featuring elegant wallpaper, a Featured Wood Finished Wall, gorgeous window covering, custom blinds and a stunning coordinated furniture package. The open layout also connects to the private new pool and patio area, perfect for relaxed get-togethers, holiday celebrations or quiet evenings under the stars. Addn features inc, 3 OSP, Turnkey, Above Flood, Storage, privacy.

Freshly renovated throughout and nestled on one of Old Towns most coveted streets, youll discover this captivating home steeped in rich history. The kitchen has new granite counters, new stainless-steel appliances & has been opened up to completely transform the space creating a modern feel and functional room. The Richard Roberts home, originally transported from Green Turtle Cay, Bahamas in 1847, stands as a cherished Key West icon. With 4 or 5 bedrooms, 3 baths, plus an office space (or 5th bedroom), its versatile floor plan offers endless possibilities. Enjoy the outdoors with four inviting porches (two on each side), warm wood pine walls, and heart pine floors throughout, this residence has earned 2 stars through the years from the Historical Florida Keys foundation. A wonderful great room or downstairs primary suite effortlessly spills onto a side yard deck & jacuzzi. Access to the second floor is via an outdoor staircase and the third floor hosts a generous bedroom and bath suite or could also serve as two bedrooms. This historically significant home is a true Key West landmark. Just 3 blocks from Duval St. & the waterfront, its quiet neighborhood is walkable to all the shops, galleries & fine restaurants.

A Historic Masterpiece originally built prior to 1912 and completely updated to the highest quality in the legendary Meadows neighborhood of Key West. 1317 Olivia Street is a two-story designer home perfectly paired with exotic tropical landscaping, custom swimming pool and water feature, IPE Brazilian hardwood decking, and sophisticated outdoor shower. The spacious master bedroom offers privacy and comfort, complete with a walk-in closet and custom built-in dresser. At the heart of the home, the chefs kitchen features a natural quartzite island with a waterfall edge flowing effortlessly into the open dining and living area with hardwood floors throughout. Here youll find 12 foot saw-tooth vaulted ceilings and low hung floating cabinetry along the entire western wall, creating a striking visual anchor for the room. A full bathroom is conveniently located off the kitchen, adding ease for guests. The living space extends to a dramatic wall of accordion-style impact sliding doors, opening to the saltwater pool and lush gardens that softly illuminate at dusk. Thoughtfully designed outdoor areas include sunbathing spaces, outdoor dining, and multiple seating areas, making it an ideal island retreat. With off-street parking, an X-Flood zone location, a whole house generator, and a minimalist yet impeccable design, this home is a unique opportunity to experience the Key West lifestyle with privacy and elegance in one of its most desirable neighborhoods.

Welcome to paradise at 22562 Jolly Roger Dr in beautiful Cudjoe Key! This custom built, 4-bedroom, 2-bath home features open water views, a designer kitchen with high-end finishes and Viking appliances. In addition, on the first floor there are two guest bedrooms, an office and bathroom. The second floor is where you will find the third bedroom as well the primary bedroom complete with private balcony, ensuite bathroom and walk in closet. Outside the property boasts double decker porches, covered hot tub, full swim spa, and new dock. In addition to the garage there is ample room for vehicles, boats and extra storage. The property is equipped with RV electrical and sewer hookups for added convenience. The property features impact windows and doors and is a stones throw from American Shoal, Lighthouse, Looe Key Reef, and Square Grouper restaurant.

This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone elses overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890 Sanborn maps show an additional house on the property, that may be able to be rebuilt with permission from the city (buyers to verify). The home has plenty of the original Dade County pine waiting for restoration. Also featuring historic windows and double balconies. Currently the home is a legal duplex, each a 2 bedroom, 1 bath apartment. Buyers could retain the duplex or transform it into a stunning single family residence in the most sought after neighborhood in all of Key West.

Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated windows and doors installed in 2016, including custom 5-panel EuroWall stacking doors that create a seamless indoor-outdoor flow. Modern elegance is evident throughout, with stainless cable railings and a zero-grout tiled walk-around porch. Offered furnished with Restoration Hardware and Room & Board pieces valued at approximately $45,000 (art excluded), also includes TVs.The outdoor spaces feature a heated pool featuring a Coralina stone deck sourced from the Dominican Republic, designed to stay cool underfoot. New pool equipment, including a heater and pump installed in 2018. Boating enthusiasts will appreciate the 21.5 wood dock with a Slide-Moor Dock system, complete with water access, as well as a floating dock system perfect for kayaking and paddleboarding. The propertys tropical landscaping, accented with solar yard lighting & cozy lounge areas create wonderful, private space to enjoy serenity or entertain guests.The gourmet kitchen, updated in 2022, features quartz countertops, modern blue cabinets, and Samsung Bespoke appliances. Dont miss your chance to own this luxury retreat in the heart of Cudjoe Key. Just 22 miles to Key West and 3 hours from Miami. Fantastic bar/ restaurant/ and coffee shop within walking distance!

This home is not a drive by! Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainers dream place. All new paint inside. New Roof as of 01/2025.This home is NOT a drive by- must see inside. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding .... Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking appliances, chefs kitchen, wet bar, icemaker & additional drink fridges. Large Tiki Hut with fans, concrete heated pool and chiller too. Bring your big Boat and Smaller one too.....2 boat lifts (20K and 12K), boat house, outdoor shower, swat mosquito system, RV hookup, Terminix warranty, video surveillance, large storage shed, full home surge protection, ample storage inside and out. All tropically landscaped, paver driveways & yard fenced for your pets and privacy. Full concrete seawall & covered boat slip. Home is offered mostly furnished and outdoor furniture is included too. Location! Location! Location! New Paint inside-neutral color. And New Roof 2025.

MOTIVATED SELLERS all offers considered! Smugglers Cove is keys living at its finest, nestled in the mangroves exuding privacy. This unique gated custom-built waterfront property is located on Bogie Channel with easy access to the Gulf & Atlantic. Offering split level living with legal ground level accommodations featuring stainless steel appliances, induction stove, a hammered copper farmhouse style sink, and a distinct 16 concrete countertop, custom bath with washer and dryer. The second floor is the master suite; with its own petite kitchen area, living room, office, bonus room, and separate washer and dryer. This is a dream property for fishing & lobster enthusiasts or nature lovers, you are surrounded by a wildlife sanctuary! Moor your boat up to the jetdock with seagate or out of the water onto the custom jetdock with kayak launch in your private 20ft deep boat basin/lagoon brimming with sea life. The owner is including 2 kayaks & Penn fishing poles. This stunning property features 2 private beaches, a 60ft pool, and a hot tub island which is encompassed by bamboo to allow absolute privacy. You will enjoy lush mature landscaping with automated irrigation to make upkeep easy. This property is equipped with state of the art security system, fully customizable solar lighting, a 6 fence, circular drive offering ample off street parking to accommodates all of your guests and has plenty of space for a RV and all of your toys! Life Is Great Behind The Gate! Workshop, bar, banquet, bbq area and greenhouse. 10% allotment to add on is also available, buyer to verify.

Discover the Ultimate Family Friendly Oasis or Fishermans retreat in this beautifully renovated concrete, single-level canal-front Home. Situated on an oversized lot of 8000 sq. ft. this 3BD/3BA residence offers the perfect combination of peace, privacy and endless outdoor enjoyment.Located at Mile Marker 6, Key Haven offers excellent access to world class fishing and the open waters of both the Gulf and the Atlantic with no bridge restrictions, and a consistent 3ft draft. The tea-shaped cancel provides easy navigation, while the 14,000 lb private boat lift and 80ft. of concrete seawall gives you all the protection and flexibility you need for a variety of watercraft vessels.After a day on the water, relax under the Brand-new Oversized Tiki Hut, the ideal spot to cool off and soak in the breathtaking waterfront views. The newly built pool adds a luxurious touch and creates an outdoor oasis with so much space to enjoy the Beautiful Weather that the Florida Keys is known for.Interior has been redesigned and remodeled and now offers a modern open plan concept with large kitchen at the epicenter of the Home and waterviews from every rooms.Large Private Master suite with King Bed and separate sitting area, large En-suite Bathroom and oversized closet offers all the space you will need.Two additional Bedrooms and 2 Full Baths, appointed with new finishes and furniture offer all the comforts for a growing family and all your visiting friends.Two new ACs, New hot water heater, all New Appliances and finishes with a low maintenance exterior means a no Honey Do list for years to come, so that when you come to your Key West home, you can relax and Enjoy.Plenty of room for parking an assortment of vehicles, Trailers or an RV.Vacant and ready for immediate occupancy!

3801 Flagler offers bold and expressive spaces, making it a unique property for those who appreciate modern design and thoughtful details. As the personal home of an architect and a licensed Florida real estate broker, the spirit of this place is a combination of style and function that feels both casual and elegant. The property is a large 9,500 SF corner lot with two separate structures. The over 1000 sq ft main house has 18-foot vaulted ceilings, a beautifully designed chefs kitchen, a serene bedroom, a spa-inspired bath, and a concrete and metal stair leading to an intimate 286 SF loft space. A unique highlight of this home is the oversized, climate-controlled two-car garage, which is perfect for car enthusiasts or those who desire separate space for a home gym, workshop, studio, or other accessory uses. The driveway offers off-street parking for two vehicles. The garage currently houses a restored 1974 Toyota Land Cruiser, available for purchase under separate negotiation. Above the garage, nestled among the treetops, is a 696 SF guest suite with flexible living/office space, a bedroom, a full bath, a coffee bar, and a large walk-in closet. The finished floors are elevated above the FEMA flood zone AE-8, and the recent renovations and additions have created a safe and stylish home that will endure for years to come. The outdoor spaces take advantage of coastal breezes, and the abundance of mature landscaping creates a tropical paradise perfect for pets and play. A two-tiered pool and surrounding deck provide a postcard setting for relaxing, unwinding, or entertaining. The custom corrugated metal and wood shiplap fencing that surrounds the property offers privacy, security, and a striking statement that sets the mood for what exists inside. The property is offered turnkey, minus the artwork and owners items. Dont miss the opportunity to own this distinctive property. Call for a private showing today.

This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance of restaurants, art galleries, and Duval Street, the location is ideal. A spacious porch with classic painted Cuban tiles provides a relaxing outdoor retreat, while reclaimed heart pine flooring extends throughout the interior. The open floor plan offers a seamless view from the living room to the pool deck, making it perfect for both relaxation and entertaining. The original tongue-and-groove Dade County Pine has been carefully removed, refinished, and reinstalled, creating a warm and inviting atmosphere.The L-shaped kitchen overlooks the heated dip pool and features custom craftsman shaker cabinets and quartz countertops. The master suite is conveniently located on the first floor, complete with an en-suite bathroom and walk-in shower. Two guest bedrooms, each with en-suite baths and vaulted ceilings, are located on the second floor.This home has been completely rewired, replumbed, and foam-insulated, ensuring compliance with modern building codes. A new foundation and a reinforced metal shingle roof have been added, along with fabric hurricane shutters for protection and insurance benefits. Smart switches, appliances, locks, and wired ethernet connectivity allow for remote home management via phone.The property is located in the X Flood Zone! The propertys historic charm makes it a remarkable piece of Key West history. Owner is a Lic. FL Real Estate Agent.