Refine Search
Sort by
$1,049,999
5 Beds 5 Baths 615085 MLS
MOTIVATED SELLERS!!! This isn't just a home, it's a lifestyle upgrade in the heart of the Keys. Welcome to a truly one-of-a-kind 5-bedroom, 4.5-bath residence that perfectly blends space, privacy, and versatility. Set on a generous 10,700 sq. ft. fully fenced lot, this property offers the freedom to live, entertain, and store all your toys, boats, RVs and multiple vehicles, with ease. Inside, a thoughtfully designed three-level layout creates the perfect balance of comfort and function. Multiple living areas give everyone their own space, while spacious bedrooms with large closets and abundant storage make everyday living effortless. The first floor is built for entertaining, featuring a private gym, half bath, and an oversized two-car garage, ideal for hosting or creating your own retreat. Upstairs, elevate your lifestyle with a custom home theater that transforms movie nights into an experience. Four screened-in patios and an open balcony invite you to enjoy the island breeze year-round, creating seamless indoor-outdoor living. Step outside to your private oasis, a saltwater pool with a tranquil water feature, surrounded by plenty of space for grilling, lounging, and unforgettable gatherings. Located just minutes from John Pennekamp Coral Reef State Park, shopping, and top schools, with Miami only an hour away, this home offers the perfect mix of convenience and escape. If you've been waiting for a home that truly has it all, this is it!

464 Lime Dr, Key Largo

$5,950,000
6 Beds 8 Baths 617710 MLS
Private Old Town property with built-in income and exceptional flexibility. Ideally located near the Historic Seaport and Fausto's, this three-residence property is currently configured with two leased units generating immediate income and a separate 3-bedroom owner's residence with pool. The rear owners unit offers 3 bedrooms and 3.5 baths with direct access to the tropical courtyard pool, while the upper 2-bedroom, 2.5-bath apartment and elegant Eaton Street facing 1-bedroom, 1-bath cottage provide established rental opportunities. Gated, private, and complete with three off-street parking spaces, this is a rare opportunity to live in the heart of Old Town while your property works for you--or maximize returns with a fully income-driven approach.

723 Eaton St, Key West

$640,000
2 Beds 3 Baths 618028 MLS
NEW LOWER PRICE!! This beautiful 2-bedroom, 2.5-bathroom condo offers everything you need for an stress-free retreat or your full-time piece of paradise. Step inside to a light and bright interior filled with upgrades and thoughtful finishing touches. Two screened lanais provide the perfect spot to relax, unwind, and soak in the stunning views of the lush tropical landscaping, sparkling pool, BBQ tiki hut, and the breathtaking Florida Bay sunsets. This condo comes with assigned parking, dockage and ground-level storage, ideal for keeping your fishing and diving gear just steps from your boat, making your water adventures effortless. Located in a prime spot, it's an easy commute to Miami for a quick weekend getaway or an extended stay in paradise. You'll also be close to the best shopping, dining, and nightlife the Florida Keys have to offer. BONUS: Enjoy peace of mind with the state-mandated engineering inspection complete and all restorative work finished. This is a rare opportunity to own a worry-free slice of paradise! Don't wait—schedule your private showing today and experience the best of bayfront living in the Florida Keys!

200 Harborview Dr Unit 101, Tavernier

$2,199,000
6 Beds 5 Baths 617882 MLS
This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2 bath, open-concept living area & updated kitchen w/ quartz countertops, wine cooler, & pantry overlooking the pool. The master suite has a built-in office, a custom walk-in closet system, & updated bath w/walk in shower. Main Level - Guest Suite is freshly painted w/private entrance, full kitchen, dedicated laundry, & full bathroom. Upper Level -3 beds & 2 baths, w/d, private entrance, 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, The secluded backyard features a heated/chilled saltwater pool w/custom water feature by renowned master potter Jay Gogin. The grounds are secured by unique bamboo fencing and include a refreshing outdoor shower. Whole-house Generac generator and a large Rheem on-demand gas tankless water heater. Front of the house features an elevated patio overlooking the street. metal roof, accordion/panel storm shutters, & 2 driveways as well as 3 off-street parking . Need 24 hour notice to show!

1609 United St, Key West

$599,000
2 Beds 2 Baths 618834 MLS
Welcome to your private slice of paradise at 3675 Seaside Drive, Unit 342. This highly sought-after end unit offers exceptional privacy, abundant natural light, and a tranquil coastal setting. The bright, open-concept floor plan is designed for effortless island living, with a spacious living and dining area that flows seamlessly from the well-appointed kitchen. The split-bedroom layout provides comfortable retreats, while generous storage enhances everyday convenience. Step onto your private balcony to enjoy refreshing ocean breezes and peek-a-boo ocean views overlooking the peaceful Salt Ponds Preserve - a protected area ensuring your natural backdrop will remain unobstructed for years to come. Beautifully maintained grounds, a recently renovated resort-style pool and heated spa, fitness center, tennis courts, and gated entry create an exceptional lifestyle in one of Key West's most desirable communities. With conventional financing now available, buyers have increased lending flexibility. Furnishings are negotiable, making this move-in-ready residence an outstanding opportunity to own your piece of paradise.

3675 Seaside Dr Unit 342, Key West

$1,975,000
4 Beds 2 Baths 618211 MLS
This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The nearly 5,000-square-foot lot stretches from Fleming Street to Stickeny Lane, offering ample off-street parking and a golden opportunity to expand your tropical living dreams. Nestled in the heart of Old Town, 1115 is just blocks from the historic Seaport and a stone's throw from the city's famous restaurants and nightlife. Early 1900s Sanborn maps even hint at an additional house on the property that may be rebuilt with city permissions (buyers to verify). The home still contains generous pockets of its original Dade County pine, along with historic windows and double balconies that invite sea breezes and sunset cocktails. Currently a legal duplex, each side offers 2 bedrooms and 1 bath. You can keep the duplex as-is, or transform it into a stunning single-family residence in the most sought-after neighborhood in all of Key West.

1115 Fleming St, Key West

$699,000
3 Beds 2 Baths 616379 MLS
Hidden Oasis in one of the best areas of all of the Florida Keys. This spacious and airy 3 bedroom 2 bath home features vaulted tongue and groove ceilings, impact windows and doors, a superior layout thats ready for its new owner. Perfectly situated in Key Largo minutes from John Pennekamp park, shops, dining, and so much more your new home gives you the very best the keys have to offer. Recently updated chef's kitchen with white shaker cabinets, stainless steel appliances, quartz counters, and marble backsplash. Freshly painted and ready for its new owner! Updated bathrooms gives the spa like experience. Washer and Dryer inside the home. Completely turn key home can be sold furnished, just bring your toothbrush! Come and see today!

239 Lignumvitae Dr, Key Largo

$4,600,000
5 Beds 6 Baths 617341 MLS
Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

117 Leoni Dr, Islamorada

$350,000
3 Beds 3 Baths 616142 MLS
Elevate your lifestyle with this Fractional Ownership at Fisherman's Cove, the Florida Keys' most exclusive private residence club. Located along Blackwater Sound in Key Largo, this luxurious retreat offers 2,300 square feet of beautifully designed living space, including three generously sized bedrooms along with three full sized bathrooms. The newly renovated interior offers a modern-contemporary look with a tropical island twist. A fully equipped gourmet kitchen with bar seating invites indulgence, while your expansive private balcony offers front-row views of the stunning surroundings. Whether you're enjoying the rooftop owners' deck, relaxing by the pool in one of three private cabanas, or venturing out to the water with access to the 26' Sea Fox or 24' Contender boats, every moment at Fisherman's Cove is a luxurious escape. With concierge and housekeeping services ensuring your every need is met, this is more than just a residence—it's a lifestyle. Conveniently located above Jimmy Johnson's Big Chill, you'll enjoy exquisite dining and entertainment. Fisherman's Cove is the ultimate in exclusive, high-end living, offering unparalleled access to the best the Keys has to offer. Owners enjoy the privilege of year-round flexibility -- typically 5-7 weeks annually -- with opportunities for additional stays as availability allows. This property cannot be rented out. Privileges are for owners only.

104000 Overseas Hwy Unit 5 - 5, Key Largo

$875,000
2 Beds 2 Baths 617600 MLS
Discover your dream waterfront getaway in the Florida Keys! This stunning 2-bedroom, 2-bath half duplex on 7th St in the highly sought after Key Colony Beach offers an unmissable opportunity. Boasting the widest canal in the area, it's a boater's paradise with ample dock space for large vessels and potential for a boat lift (with permits). Enjoy outdoor living at its finest with a new 9x16 chickee hut, installed in 2023 and equipped with electricity and a fan for ultimate comfort. The home is move-in ready, featuring a completely renovated kitchen with granite countertops, updated bathrooms, and impact windows and doors throughout, with the exception of one slider. A unique walkthrough connects the guest room to the master suite, adding to the home's charm and convenience. This home is in the vacation rentals and has bookings currebtly through April 18, 2026.

26 7th St, Key Colony

$885,000
4 Beds 2 Baths 617233 MLS
Beautiful corner-lot CBS home in the heart of Plantation Key. This 4-bedroom, 2-bath residence offers 1,964 sq. ft. of living space and is located with desirable X flood zone. Notable features include impact windows and doors, a spacious open floor plan, and a bonus family room ideal for entertaining or additional living space. The bright interior is filled with natural light, with a functional kitchen designed for everyday living and gatherings. Step outside to a covered porch overlooking tropical landscaped yard, creating a relaxing outdoor retreat. Additional storage spaces provides added convenience. Ideally located within walking distance to top-rated schools, dining, and local amenities, this home offers easy access to the best of the Florida Keys lifestyle. Homeowners park with a boat ramp; fantastically located for easy boating with immediate access to the ocean, as well as bay access through Tavernier Creek. (HOA membership) Pride of ownership is evident throughout--this is an excellent opportunity in a prime Plantation Key location.

160 Ridge St, Tavernier

$640,000
2 Beds 2 Baths 616992 MLS
Million dollar views! Ocean and Gulf views make this an affordable waterfront gem. Situated in a quiet and peaceful Bay Point neighborhood, this home is only 17 miles from Key West allowing quick city access and return to waterfront bliss. This Keys-style fish camp offers a waterfront, manufactured home with 2 bedrooms and 2 baths. The side yard was once an orchid house and could be returned as a leafy oasis or reconfigured for parking. Enjoy easy living on 62 feet of ocean front with spectacular sunset views! Renovate to make it your home, vacation/weekend get-away, employee housing, or rebuild as a brand-new ocean front house. Near famous Baby's Coffee Shop, pickleball and tennis courts, and a community playground.

4 Shore Dr, Saddle Bunch

$835,000
3 Beds 3 Baths 617435 MLS
Key Largo 3 Bedroom / 3 Bathroom CBS home located in an X flood zone and room for a pool! NEW METAL ROOF 2026. This well-maintained property sits on a nearly half-acre corner lot bordered by three streets, offering exceptional privacy. Approximately 1,600sf of additional land can be cleared, bringing the total clearable area to roughly 8,000sf -larger than most lots in the Keys and ideal for a pool, expanded outdoor living, or other custom improvements. With over 1,800 sq. ft. of living space, the layout offers great separation. The primary suite occupies its own wing with a walk-in closet, en-suite bath, and private screened porch. A Florida room creates a comfortable buffer from the main living area. Both guest bedrooms include en-suite baths, and one opens directly to a spacious screened porch that also connects to the living room. Built in 2004 with impact windows and doors, plus AC (2018) and a new water heater (2025). The homeowner's park is right around the corner, offering a clubhouse, boat ramp, and a neighborhood beach - perfect for launching kayaks or paddle boards or letting your dog cool off in the water. Move-in ready and turnkey, this home delivers privacy, comfort, and the Keys lifestyle all in one.

78 John Silver Dr, Key Largo

$9,500,000
6 Beds 11 Baths 610645 MLS
Casa Mañana Shores, located in the heart of Marathon, is a developer's dream or a private owner's potential paradise. This secured gulf front estate offers 3.86 acres of land and is surrounded by an eight foot concrete wall with three gated entrances. The property boasts approximately 540 linear feet of Highway frontage and 695 linear feet of water frontage. It offers 218 feet of concrete dockage, including a cut-in protected boat slip. There is even room for a helicopter landing pad. This unique property is zoned mixed-use commercial and comes with one commercial transferable building right. It is currently a private residence with a separate garage and workshop. The 10,852 square foot mansion is solid concrete construction with concrete pilings and copper pipes. It has ten bedrooms, six and a half bathrooms, and a sauna, game room and great room. Repairs are needed, and the interior needs substantial updating. An attached partially screened enclosure holds an impressive 12 ft deep swimming pool that measures 25 x 50 ft. The garage/workshop is a separate structure with two rooms with mini split air conditioning. The existing structures could be demolished for those with a vision, leaving you with a 3.86 acre blank canvas in the center of town. Its versatile designation offers multiple possibilities for residential and/or commercial use. Over the years it has previously housed a motel with a marina, a 19-unit trailer park, and a restaurant. This property lends itself to a variety of development or rehabilitation possibilites to create the vision of your dreams!

6500-6600 Overseas Hwy, Marathon

$2,444,000
2 Beds 2 Baths 618772 MLS
Rare opportunity to secure a prime waterfront homesite on highly desirable Duck Key. This is presenting the perfect canvas to design and build a custom island retreat exactly to your vision. Even better, the property is ROGO exempt, meaning no waiting for a new building permit -- a verified build right is already in place (letter on file). Boaters will appreciate the 82 feet of dockage, deep water dockage and exceptionally quick ocean access. Two davits that are 5,500 lbs each one and a turner on one of them. Center Island is a prime location for privacy on Duck Key. Navigate under the Seaview Bridge and head out through the Headpins for fast access to open water, or take the main channel route for larger sportfishing vessels. Enjoy all the lifestyle perks Duck Key is known for, including nearby dining at Hawks Cay Resort, a welcoming island community. that is golf cart friendly. Fly into Marathon airport with your own plane or Million Air and then drive 15 minutes to your island oasis. Whether you're planning a full-time residence or luxury vacation escape, this is your chance to build your dream home in one of the Florida Keys' most sought-after boating enclaves.

154 S Indies Dr, Duck Key

$9,700,000
4 Beds 7 Baths 617714 MLS
This custom-built, elevated two-story estate sits on a 7,300 SF point lot at the coveted tip of Adam's Cut Waterway, with 167 feet of waterfront offering panoramic views that open directly to Largo Sound with ocean access. More than a home, it is an unparalleled opportunity to own an iconic piece of Keys history—an architecturally significant retreat built to exceptional standards of strength, beauty, and design. Spanning 3,723 SF, the 4BR/5+2BA residence features a triple-poured concrete roof, 8 inches of concrete between floors, Italian La Finestra impact windows and doors, whole-house sound system, interior elevator, Shell Reef honed limestone floors, and concealed-hinge custom doors. The main level showcases a stunning light-filled living room framed by floor-to-ceiling windows, a remote-controlled drop-down TV, stone accent wall, and sleek wet bar—all opening to the expansive wraparound terrace overlooking Adam's Cut. An open dining area complements the chef's kitchen with a backlit polished Plume Quartz waterfall island, JennAir gas cooktop, integrated refrigeration, and Liebherr wine cooler. This floor includes three bedrooms, including a junior suite with private balcony and spa-style bath, plus a designer powder room, laundry room, and two additional ensuite guest rooms. The private principal suite spans the second floor, featuring a high-pitched ceiling, midnight bar, elevated bed platform, flexible additional room, and a spa-inspired bath. It opens to a private terrace with a rooftop infinity pool, swim-up bar, and jacuzzi for a true resort experience. Ground-level highlights include a grand covered terrace w/summer kitchen, Lynx grill, salt-chlorinated pool, teak ceilings, standalone bar, and cabana bath. A hidden gem is the brick-lined, temperature-controlled 200-bottle wine cellar w/ a decanting area. A 77' private dock w/ permitting in progress for a 30,000 lb boatlift, swim platform, and sunning areas complete this extraordinary Keys masterpie

180 Pompano Dr, Key Largo

$150,000
617655 MLS
Rare Monroe County Transferable Development Right (TDR) Unlock the Potential for an Attached Affordable Dwelling Unit! Seize a unique opportunity in the Florida Keys with this Transferable Development Right (TDR)—your key to adding an attached dwelling unit that meets Monroe County's affordable housing criteria. Whether you're a homeowner dreaming of expanded living options or a savvy investor seeking long-term value, this TDR opens the door to endless possibilities. With buildable rights in the Keys limited and increasingly valuable, this TDR offers a path to legal, compliant residential expansion—perfect for creating an additional income-producing unit, multigenerational space, or workforce housing solution. Why This TDR Is a Game-Changer: ✔ Receiver site must allow an attached dwelling unit, providing flexibility and design freedom. ✔ Must meet affordable housing criteria, making this ideal for workforce housing or long-term rental planning. ✔ A rare chance to explore multi-dwelling potential on your property. ✔ Perfect for homeowners, investors, or developers looking to maximize property utility in a county where development is highly regulated. Ever Dreamed of a Secondary Structure? This could be your moment. Imagine an additional living space for family, rental income, or future needs—all while staying within Monroe County's regulations. Not sure if your property qualifies as a receiver site? Contact us today and we'll help you confirm eligibility and explore the possibilities.

unincorp Monroe, Not Provided

$2,490,000
3 Beds 8 Baths 617030 MLS
**6%+ Cap Rate Opportunity ** Now offered at $2,490,000, this income producing Old Town property offers strong cash flow and immediate investor appeal. Located just steps from Duval Street, 402 Appelrouth Lane offers a rare investment opportunity in a premier X Flood Zone location. This mixed use property has income potential from residential and commercial units. With over 5000sqft of interior space this iconic structure showcases tall ceilings, historic architectural character and custom artistic details that give it Old Town Charm. Appelrouth Lane is known for strong foot traffic, established neighboring businesses and a desirable central location. just minutes from restaurants, galleries, shopping and Key West nightlife. Opportunities like this are exceptionally rare.

402 Appelrouth Ln, Key West

$899,000
3 Beds 2 Baths 618444 MLS
Spacious and well-designed 3-bedroom, 2-bathroom home offering a flexible and functional floor plan perfect for today's lifestyle. The main level features an open kitchen with center island, ample cabinetry, and stainless appliances, flowing seamlessly into a bright family room. A separate living room and dedicated office provide additional space for work, relaxation, or entertaining. The first floor includes a convenient guest bedroom and full bathroom, ideal for visitors or single-level living. Upstairs, you'll find a private primary suite with en-suite bathroom and walk-in closet, along with a second guest bedroom—creating excellent separation and privacy. Step outside to your own tropical retreat featuring a covered tiki-style deck and private backyard, perfect for outdoor dining and year-round entertaining. With its versatile layout, multiple living areas, and inviting outdoor space, this home is well suited for families, professionals, or those seeking strong rental potential. Conveniently located near local amenities and offering great value in today's market.

2012 Roosevelt Dr, Key West

$535,000
2 Beds 2 Baths 617289 MLS
Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day on the water. A resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area with tiki huts and more! Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in an exclusive gated community which adds a sense of security and prestige. This home is ready for you to move in and enjoy! Don't miss this rare opportunity to own a piece of paradise! Nightly Rentals Allowed! Plenty of potential for rental income.

701 Spanish Main Dr Unit 247, Cudjoe

$6,975,000
4 Beds 5 Baths 618703 MLS
Very few things in life live up to the hype--but living on ''The Creek'' exceeds it. The location is world-class, the people-watching and boating scene never gets old, and the level of construction top-notch. What makes this property even more extraordinary is that the home itself now matches the setting. Following a meticulous two-year, top-to-bottom renovation, this residence was completely reimagined--from structural improvements to the finest design details--resulting in a flawless, move-in-ready showpiece. The main living level commands attention the moment you walk in, with dramatic vaulted ceilings, exposed wood beams, and an open-concept living and kitchen area designed for unforgettable entertaining. Two bedrooms and 1.5 bathrooms complete this floor with style and comfort. The entire third level is dedicated to a private primary suite that feels like a retreat in the sky. Wake up to elevated views over the Creek from your own private porch, admire the craftsmanship of the tongue-and-groove ceilings, and enjoy a stunning spa-style bathroom featuring a soaking tub within the shower and--finally--a large walk-in closet rarely found in Keys homes. The ground level offers a fully independent guest quarters with its own bedroom, bathroom, and full kitchen. Two functional garages with durable coated floors and bright LED lighting, plus a cabana bath accessible from both inside and outside for pool days. And then there's the backyard--where this home shifts from impressive to unforgettable. A full outdoor kitchen, heated pool, and hot tub set the stage, but the dock steals the show: deep-water dockage with two boat lifts (22,000 lb and 18,000 lb) and plenty of space for visiting boats, because friends will come. Tropical landscaping, an exterior elevator, and thoughtful details throughout complete a property that simply refuses to compromise. If you're looking for ordinary, keep scrolling. If you want a home you'll never get tired of walking into, this is it.

228 Tide Ave, Tavernier

$1,399,000
616964 MLS
Discover a rare opportunity in the heart of Duck Key at 1 Trinidad Street — a premier parcel spanning over an acre in one of the most desirable neighborhoods in the Florida Keys. This exceptional property offers remarkable potential for new construction, redevelopment, or long-term investment. With its generous size, privacy, and prime location directly across from the Duck Key Clubhouse — and just steps from the pool, tennis courts, and social amenities — this site combines lifestyle appeal with investment value. Whether you're envisioning a luxury Keys estate, a multi-structure retreat, or a strategic hold for future growth, the possibilities are endless. The property carries density for up to 7 homes, and according to Monroe County, it aligns with the majority of criteria required for ROGO (Rate of Growth Ordinance) building right transfers. While formal approval must follow the county's established process, preliminary guidance supports the feasibility of securing those rights — offering a compelling path for developers and investors. Large parcels of this caliber are increasingly rare — build your vision and create something extraordinary on Duck Key.

1 Trinidad St, Duck