Divider
Content Divider

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

Total Listings 622
Order By:

$2,799,000
Key West
Martello Towers   - MM: 1.00
3 Bed, 3 Baths, 2,001 SqFt Days Listed: 18
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Blending the elegance of Danish modern architecture with the laid-back charm of island life in Key West is 1110 Johnson Street. The spacious 2000 sq ft, three-bedroom, two-bathroom home which also boasts a den and breakfast nook sits on a large, private 7500 sq ft land parcel located in the prestigious Casa Marina district on the most coveted, quiet, one-way street. The property offers plenty of room for privacy, relaxation and entertaining. Enjoy just a two-block walk to the Atlantic Ocean, Higgs Beach, White Street Pier and Salute which adds to your lifestyle options. There is also easy walking distance to the location of the monthly Walk on White event (art walk) and the weekly Key West Artisans Market (during season). With limited car traffic, Johnson Street is very quiet and perfect for jogging, dog walking and bicycling. The homes unique, widely admired front double doors are a focal point of the home. The grandiose living room opens fully to an expansive 510 sq ft covered screened in porch which is perfect for dining, entertaining and enjoying the quiet outdoors. In the evenings, crickets chirp softly as ocean breezes blow through the palms on the property. The home feels far removed from the rest of the busy world and very much in touch with nature. But if desired the screened porch could be closed in to add to the indoor living space. Additional features include a carport, off-street parking for up to three vehicles and a large, gated and bricked patio backyard shaded by a bottle brush tree which is surrounded by large ferns. There is potential for adding a second story for open ocean views, mother-in-law quarters/4th bedroom, a 12 x 24 ft pool and a pool house which makes this home even more enticing (architect plans available). Its truly a rare opportunity for anyone looking to embrace the Key West lifestyle while enjoying the ultimate in privacy, tranquility and modern comforts.

$2,799,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,223 SqFt Days Listed: 439
-19.91% ($696,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

First time on the market in over 50 years! This property is a plant lovers paradise. The owner spent his entire life collecting plants and seeds from all over the world and created a quiet serene and private oasis in the middle of Old Town Key West, on a huge oversized lot. Some of the rare plants and palms are found nowhere else in the continental United States. The main house has many structural upgrades, but the best thing is that the existing carport has HARC approved plans to turn it into a large guest cottage or studio. This is an artist/musicians dream. Quiet solitude in the middle of Key West to stimulate creative juices, or just to chill out in paradise.

$2,800,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 2,049 SqFt Days Listed: 106
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

$2,850,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 21.00
2 Bed, 2 Baths, 1,577 SqFt Days Listed: 70
-4.68% ($140,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp

Unobstructed Ocean views, you will love this Private Oasis! Enjoy the Cudjoe Key lifestyle in this fabulous 2 bedroom, 2 bath home. Built in 1984 with a well-planned 1577 sqft floorplan, perfectly situated on a corner, oceanfront 24,829 sqft lot. This beautiful home will sell fast!! Granite kitchen countertops, brand new stainless steel appliances, new AC, new tankless water heater, impact doors and windows and much more! Master bedroom on the top floor has the most spectacular ocean views and sunrises. Double sliding doors lead out to a huge private observation deck. The pool is hands down the show stopper of this property. Soak up the sun in this huge full size pool and a hot tub, or enjoy the sunsets while grilling out with your guests on the extra large pool deck. There is a screened in patio just off the living room with direct ocean views, comfortable outdoor furniture to relax on and enjoy your morning coffee. Located at the end of dead-end street, the home sits on the ocean end of the canal. Property includes a private boat ramp and dock with room for a 25 foot boat and plenty of room to park multiple boat trailers in the yard. With views of American Shoal Lighthouse in the distance, this homes location is great for trips to the reef, as well as back country for flats fishing. Some of the best fishing spots in the Florida Keys are just minutes away! Situated between Key West and Marathon, we are in the ideal location. Just a 25 minute drive into Key West you can enjoy Sunset Celebrations at Mallory Square, have a stroll down Duval Street, and dine at some of the best restaurants in the Florida Keys. Only 25 mins to the north towards Marathon you can enjoy Bahia Honda State park and Sombrero beach.

$2,895,000
Key West
Webb Realty Co Subdivision   - MM: 1.00
4 Bed, 4 Baths, 2,880 SqFt Days Listed: 176
-12.14% ($400,000) 2 Price Changes : Last Change 45 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, A FAREWELL TO ARMS. This sprawling single story property spans an impressive 8100 square feet, occupying a prominent corner lot, with a reimagined interior floor-plan. Constructed with white-painted Savannah brick over a wood frame, this residence exudes classic charm with a modern twist. Tall ceilings and a welcoming fireplace create an inviting atmosphere. Sliding glass doors seamlessly connect the interior to the outdoor patio, allowing for a harmonious blend of indoor and outdoor living spaces. The outdoor space is a tropical paradise, complete with a heated pool and soothing water feature. The main house features 3 bedrooms, 2 bathrooms, and a laundry area. Two of the bedrooms share a bathroom, while the primary suite offers a generously sized bathroom with a bath tub, double sinks, and an indoor and an outdoor shower. Enjoy the airy ambiance of the open floor plan, with a spacious living room and dining area that together span over approximately 1200 square feet. The modern kitchen is well-appointed, with easy access to the pool area and the charming conch-style 1/1 guesthouse. The main house has a semi-circular driveway and can accommodate 3-4 cars. The guesthouse also includes its own entrance on Walton Street and an off-street parking space.

$2,925,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
4 Bed, 4 Baths, 3,656 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Fully renovated and redefined mid-century home, perfectly tailored for modern island living. Located on one of the most desirable streets in Key West, this turnkey property sits on an oversized 9,500 square foot lot in the heart of the island. Offering over 3,600 square feet of thoughtfully designed living space, the home features four bedrooms, four full bathrooms and a bonus room ideal for guests or a home office. The layout offers privacy and flexibility, with main-level guest rooms and an upstairs suite featuring cathedral ceilings, a spa-like bath and a spacious closet. The open-concept design is made for entertaining, with a sleek chefs kitchen featuring custom cabinetry, double ovens, an induction range and a walk-in pantry. Two laundry rooms and a second kitchen area upstairs add extra convenience and flexibility.Slide open the expansive glass doors and step into your own private resort. The living space transitions effortlessly to the outdoors, where youll find tropical landscaping, multiple lounge areas, a covered porch for dining or relaxing and a heated lap pool with a stunning 28-foot custom waterfall. Theres also an outdoor shower and a dedicated poolside half bath.Additional upgrades include new electrical and plumbing systems, three new central AC units, an irrigation system and a full furnishings package. The home also includes garage and driveway parking.Modern, stylish, and centrally located--this is Key West living at its finest.

$2,949,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,426 SqFt Days Listed: 143
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover your dream home at the prestigious Truman Annex Community, situated on the serene Admirals Lane. This two-story detached single-family residence offers a perfect blend of comfort and elegance with 3 bedrooms and 3 full bathrooms. Enhanced by impact windows and doors, the house also features a private carport for added convenience. Adjacent to the property lies a shared community pool, ideal for relaxation and enjoyment. Inside, the main living area boasts exquisite travertine floors, creating a luxurious ambiance. Open the French doors to the composite wood back deck, where outdoor dining, barbecues, and lounging become a daily indulgence. The fully equipped kitchen is a culinary haven, catering to every chefs desires. With one bedroom on the first floor and two bedrooms on the second floor, each with a private bathroom, this home is designed for utmost comfort and privacy. Emphasizing its prime location, this property is just a stones throw from Duval Street, the Key West White House, and the Key West Harbor, all while being nestled within the security of a gated community. Live out your Key West dreams in this exceptional property that epitomizes the essence of island living.

$2,950,000
Key West
Moffats Subdivision   - MM: 2.00
4 Bed, 4 Baths, 2,449 SqFt Days Listed: 80
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Not a duplex! This beautiful property consists of two single family homes surrounded by tropical foliage. This one-of-a-kind compound blends island charm and character. Offering a 3 bedroom 4-bath Conch house with a large separate 1 bedroom 1 bath home with a full kitchen. The 3 bedrooms, 4 bath home has wall-to-wall Dade County pine with an open floor plan and a chefs kitchen. The open concept living space flows effortlessly into a sleek kitchen with quartz countertops, stainless steel appliances, and offers a tranquil escape just steps from the pool. The second, 1 bedroom, 1-bath home provides secluded privacy for visitors or a lucrative rental opportunity. Surrounded by lush, mature landscaping and brick pathways, the private courtyard creates a peaceful hideaway, perfect dip in the heated oversized pool. Steps from Key Wests vibrant restaurants, galleries, and historic landmark.

$2,950,000
Key West
Benj Alburys Subdivisiond   - MM: 2.00
3 Bed, 3 Baths, 2,397 SqFt Days Listed: 138
-9.23% ($300,000) 2 Price Changes : Last Change 60 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Median - Dockage: Boat Slip

This is one of the very few waterfront homes in Old Town Key West that comes with a private boat slip and open water views. The house features a large living room and kitchen area and a gorgeous sunroom with floor to ceiling windows overlooking the water and leading out to a spacious deck. A private path from the deck gives access to a heated pool that is part of the HOA fees that also include use of the dock. The house comes fully furnished. The private boat slip features a custom floating boat lift and there is easy open water access from the Garrison Bight Marina for fun during the day. This Meadows house is also walking distance to Duval Street for night time dining and entertainment. Plus two private, dedicated parking spots.. A rare gem that will not last!

$2,950,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,519 SqFt Days Listed: 105
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Tucked away on a quiet lane in the heart of Old Town Key West, this one-of-a-kind compound blends island charm and character. Offering three distinct dwellings wrapped around a serene brick courtyard and heated cocktail pool, this property is a rare gem providing ultimate privacy while just steps from world-class dining, shopping, and entertainment.The main house is a light-filled updated 2-bedroom, 2-bath home featuring vaulted ceilings, hardwood floors, and French doors that open onto spacious porches. The open-concept living space flows effortlessly into a sleek kitchen with quartz countertops, stainless steel appliances, and an island with seating perfect for gathering with friends. The primary suite includes an en-suite bath and an outdoor shower tucked away for a private island experience. The second bedroom opens directly to the courtyard, offering a tranquil escape just steps from the pool.A detached 1-bedroom, 1-bath guest cottage provides secluded privacy for visitors or a lucrative rental opportunity. The third structure, set amongst the tropical landscaping, is a flexible bonus space ideal as an art studio, office, or additional sleeping quarters.Surrounded by lush, mature landscaping and brick pathways, the private courtyard creates a peaceful hideaway, perfect for al fresco dining or a dip in the heated cocktail pool. With off-street parking, a whole-house generator, and a fully fenced perimeter, this property checks every box for island living at its finest.Moments from Key Wests vibrant restaurants, galleries, and historic landmarks, these cozy cottages offer a welcoming slice of paradise in one of the most sought-after areas of Key West.Schedule your private tour today and make this hidden paradise your own.

$2,990,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
4 Bed, 4 Baths, 2,812 SqFt Days Listed: 339
-6.53% ($209,000) 2 Price Changes : Last Change 122 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Tranquil Midtown Estate feels worlds away, while just minutes to delectable dining and nightlife in exciting Key West! Nestled on nearly a quarter-acre of gated, lush tropical gardens, this spacious 3/3 main house plus 1/1 guest house comes move-in ready; boasting elevated coastal design where modern finishes and amenities meet relaxed sophistication. Indulge in year-round temperate weather from a backyard oasis, masterfully outfitted for hosting memorable gatherings with a well-equipped outdoor kitchen with gas grill, gas burner, ample prep space and beverage cooler. Lounge poolside, cocktail in hand, in the shade of a large tiki hut and cool off in the stunning resort-style pool, complete with fountain waterfalls! Additional exterior features include brick paver pool deck and outdoor rain shower. Upon entry, the main house features an open-concept great room with walls of impact glass windows and doors, providing abundant natural light. The immaculate Chefs Kitchen, with quartz countertops, glass tile backsplash, premium stainless-steel appliances, and island with seating, allows for effortless entertaining. As a bonus, a Dutch door leads to a spacious butlers pantry with laundry. The primary suite enjoys privacy in its own wing, and comes equipped with luxurious en suite, walk-in closet, and access to a private garden. The separate guest wing offers two expansive bedrooms and two full bathrooms. The well-appointed guest house offers two floors, with living room and kitchenette on the main level, complete with serene pool views and impact glass doors leading out to a private, poolside composite deck. The upstairs guest bedroom offers loads of privacy and en suite bathroom. Enjoy an abundance of covered parking with two pergola carports and additional off-street parking. Located within a quiet, established neighborhood but in proximity to restaurants and convenience stores in town, this ideal location offers the best of both worlds!

$2,995,000
Key West
White & Pierce Diagram   - MM: 1.00
3 Bed, 3 Baths, 1,615 SqFt Days Listed: 148
-7.85% ($255,000) 2 Price Changes : Last Change 35 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

TRANSIENT LICENSE - - Discover your dream Transient Vacation Rental in the heart of mid-town Key West! This beautifully refreshed home boasts a light and airy atmosphere and is sold fully furnished with rentals on the books and ready to go. Featuring three bedroooms, including a spacious primary suite and three baths, this property offers an inviting open living and kitchen area, highlighted by soft hues and vibrant tropical accents. Dine al fresco in the charming attached pavilion, perfect for enjoying the lush surroundings.Each bedroom provides direct access to different areas of the yard, enhancing the privacy and outdoor experience for every guest. The luxurious primary suite opens to the pool area through stunning French doors, while the primary bath features a spacious, tiled walk-in shower. The second bedroom, decorated with inspiring Key West art, offers a tranquil retreat with two twins that may be turned into a king. The versatile third bedroom is on the opposite side of the house with remodeled bath ensuite.Nestled in a quiet residential neighborhood, this home is just a short bike ride from the beautiful beaches on the south side of the island and the vibrant Duval Street, with the Casa Marina area even closer. This home is the ultimate vacation getaway!

$2,999,000
Key West
Riviera Shores   - MM: 3.00
5 Bed, 5 Baths, 3,124 SqFt Days Listed: 221
-22.10% ($851,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

SELLER IS MOTIVATED! WILL CONSIDER ALL REASONABLE OFFERS! Beautiful canal front home in Key West with pool and garage! Spacious main house plus guest apartment with separate entrance. Expansive nearly 14,000 square foot lot with a gated privacy fence. Main house has 3 bedrooms plus a den and 3 full baths. Large light filled rooms for entertaining including grand foyer, dining room, and the perfect living room with walls of windows showcasing canal & water views! Kitchen has wood flooring, built-in cabinets, stainless steel appliances and leads to the dining area. Kitchen opens to breezeway to garage, laundry room and courtyard. Bedrooms offer large closets and two have private access to pool/decks.. Primary bedroom suite has double closets, en suite bath and pool /water views. Central AC, terrazo flooring, laundry room, cedar lined closets, and garage.Upstairs guest suite has a 2 bedroom/1 bath apartment with kitchen and balcony with tree top canal views. Plenty of room for boat and auto parking. Lovely decked areas for relaxing poolside or enjoying the canal views while dining. Kayak from your backyard! Large lot 104x130 fenced and secluded with no neighbors on other side of the canal.

$2,999,000
Stock Island
Maloney Subdivision Subdivisi   - MM: 5.00
1 Bed, 1 Baths, 1,200 SqFt Days Listed: 41
Multi-Units - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Discover an exceptional investment opportunity with this sale, featuring a total of 4 parcels encompassing 30,000 square feet of prime real estate. This property includes two commercial units, totalling1,108 square feet of versatile space perfect for your business ventures. In addition, there are six (6) residential units, boasting a combined total of 6 bedrooms and 6 bathrooms across 4,597 square feet, making it ideal for rental income or multi-family living. Plus, take advantage of a vacant lot that provides endless possibilities for development or expansion. Dont miss your chance to own this diverse and valuable property!

$2,999,500
Key West
Mills Place   - MM: 1.00
2 Bed, 2 Baths, 1,770 SqFt Days Listed: 131
Townhouse - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Vacation rental Ocean and Harbor view unit in Truman Annex. Beautiful sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered balcony right off the main living area with living room, dining room and kitchen. The second storys primary bedroom and bath opens out to its own private balcony. Highly desirable Old Town location in Mills Place condominiums in Truman Annex.

$2,999,999
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 1,596 SqFt Days Listed: 159
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

$3,000,000
Key West
Prog Land Imp Co Diag   - MM: 0.00
4 Bed, 4 Baths, 2,276 SqFt Days Listed: 113
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Experience the true essence of Tropical living in Key West with this exquisite mid-century estate, the perfect blend of a private sanctuary and a highly coveted transient license, making it a lucrative income-producing asset. Located on an expansive corner lot, this property is enveloped by lush foliage, ensuring the utmost privacy and a serene ambiance that feels worlds away yet remains just moments from the vibrant heart of Key West. As you enter through the winding brick pathways, you are greeted by mature landscaped gardens and multiple outdoor spaces designed for both relaxation and entertaining. The heart of this oasis is a stunning 35-foot heated pool accompanied by a covered pavilion, offering the ideal setting for leisurely afternoons or elegant gatherings. The main residence showcases nearly 2,000 square feet of thoughtfully designed living space, featuring a primary bedroom suite with a glass enclosure sitting area that invites natural light to cascade throughout. Two additional guest bedrooms and a spacious living/dining area open through multiple sets of French doors, seamlessly blending indoor and outdoor living. Adding to the propertys allure is a separate studio guest cottage. This flexibility allows you to enjoy a tropical getaway during your visits while maximizing rental potential from the main house offering the best of both worlds. Ideally situated just a short stroll from pristine beaches, the iconic White Street Pier, and premier tennis and pickleball courts, this estate provides an unmatched opportunity to own a private oasis in one of the most sought-after destinations.

$3,100,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
5 Bed, 5 Baths, 2,711 SqFt Days Listed: 196
-6.06% ($200,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Stately Key West home has undergone a stunning renovation but maintains classic Keys charm with a beautiful wood staircase, stained glass window and transom, Dade County pine walls, and wraparound porches on both levels. Centrally located in Key West this home is the perfect island residence with POOL! The main level offers plenty of room for entertaining with large spaces for conversation, dining, games, cooking, and more. Spacious chefs kitchen with breakfast bar and natural design elements throughout. Kitchen flows to the sitting area with designer bar space and wall of sliding glass doors opening to the pool and a pass-through window to covered porch area. Main level offers one bedroom with outdoor access and a full bath. The upper level boasts four additional bedrooms including primary suite. The primary bedroom is a resort like retreat with elegant spa tub, large walk-in shower with multi-jets, rain forest shower, linear drain and walk-in closet. The primary also features access to deck space perfect for morning coffee. Bedroom with en suite bath and deck access. The other upstairs two bedrooms share an en suite full bath. Perfect tree top views from upstairs on the wraparound porch. The third level is currently a music room and offers access to the widows walk for top of the island views! Lovely private outdoor areas with mature tropical landscape. Pool area with tiki hut offers covered space for reading or relaxing. Garage has room for parking or storing your island water toys. Laundry room on second floor and bonus washer & dryer in garage. Elevator to each floor. Central AC. This is the perfect island home!

$3,141,000
Key West
Riviera Shores   - MM: 3.00
3 Bed, 3 Baths, 2,386 SqFt Days Listed: 69
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 58ft.Concrete

Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled canal frontage, complete with a new 24k lb boat lift and ~58 of new seawall, offering seamless ocean access. Step inside to experience the spacious living areas, illuminated by tons of natural light, with tile flooring throughout. Marvel at the attention to detail in the updated kitchen featuring a waterfall island and all new stainless steel appliances. Outside, a heated salt pool, equipped with automation and a water feature, invites you to unwind amidst the lush turf and enchanting landscape lighting. Relish in unparalleled privacy with a comprehensive privacy wall and fencing, enhanced by a Mosquito Nix system for a pleasant outdoor experience. Enjoy the added conveniences of a whole-house automatic generator and on-demand gas water heater. Nestled in an environment that offers the best waterfront living, your lifestyle is enhanced by limitless opportunities for boating and fishing--right from your backyard: automatic front gates, circular driveway, and awning-covered parking round out this unparalleled offering. Elevate your life with this matchless blend of luxury and oceanic freedom!

$3,150,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 2,697 SqFt Days Listed: 127
-13.70% ($500,000) 4 Price Changes : Last Change 12 Days Ago
Townhouse - Active - Waterfront No
Side of Island: Median - Dockage: None

Old Town Villas at Key West is a luxurious gated development just 1 block off of Duval Street. This townhome has 3 bedrooms, 3.5 baths on 4 floors. A private elevator in each unit takes you from the 2 car garage to the rooftop terrace. Just under 2,700 SF of solid concrete construction accompanied with high end appliances, a large community pool & cabana area.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-16-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA