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$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

$1,399,000
3 Beds 2 Baths 617068 MLS
Welcome to the extraordinary! Unique in design this 3 bedroom home in highly desirable community of Stillwright Point, one of Key Largo's most sought after waterfront communities. Approximately a 1/4 acre lot, 86ft of deep-water dockage and its own boat ramp make this a prime location for power or sail enthusiasts. The outside accommodations are complimented that with spacious rooms, large open kitchen, large dining and living area in a hexagonal design. From the main level and top floor there is an exceptional vantage point of the sound as well as full on view down the waterway as it bends behind the residence. While this home needs some updates, seller has loved and enjoyed it since 1995. It now awaits the next owner to transform this unusual and charming Keys treasure into their own piece of paradise.

Not Provided

$1,399,000
3 Beds 2 Baths 617709 MLS
Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while embracing modern luxury. Impact doors and windows, wide-plank engineered wood flooring, and an updated chef's kitchen with gas range create interiors that are both stylish and functional—ideal for relaxed living and elegant entertaining. The serene Primary Suite is a private sanctuary, featuring expansive picture windows that frame stunning views of the home's massive, newly refurbished waterfront pool, evoking a true resort-style experience. Designed for the boating enthusiast, the property offers deep-water dockage on a flow through canal with a concrete dock and 10,000-lb boat lift, providing effortless access to open water. A whole-house generator with automatic transfer switch ensures uninterrupted comfort and peace of mind year-round. Located within one of the Keys' most desirable waterfront neighborhoods, residents enjoy access to the Cudjoe Gardens Marina a full-service marina with fuel, bait, refreshments, and boat ramp, along with a beloved Bent Prop waterfront restaurant—all just moments from home This is a rare opportunity to own a historically significant, architecturally distinctive residence that seamlessly blends mid-century design, modern upgrades, and an unparalleled waterfront lifestyle.

51 Drost Dr, Cudjoe

$1,398,000
3 Beds 2 Baths 620387 MLS
Extensively renovated CBS pool home in desirable Duck Key featuring luxury finishes, smart-home technology, and contemporary coastal design. This beautifully updated Florida Keys retreat offers an exceptional blend of modern style and island living, highlighted by a dramatic multi-story screened porch that captures natural light, tropical breezes, and seamless indoor-outdoor living. The designer kitchen serves as the heart of the home, showcasing an oversized quartz waterfall island, premium smart appliances, custom cabinetry, and a spacious walk-in pantry. Throughout the home you'll find soaring tongue-and-groove ceilings, oversized interior doors, designer lighting, and high-end finishes throughout. The luxurious bathrooms have been thoughtfully redesigned with custom tile work, floating vanities, LED mirrors, premium fixtures, and spa-inspired showers that create a true resort-style experience. Thoughtful upgrades and attention to detail are evident throughout every room. Outside, enjoy a beautiful new pool surrounded by an expansive paver deck, creating the perfect setting for entertaining or relaxing in the Florida Keys sunshine. The impressive screened outdoor living area offers a unique architectural feature, providing an inviting space to enjoy island breezes year-round. Elevated construction provides abundant enclosed storage, flexible bonus space, and room for hobbies, fitness equipment, or additional storage needs. Professionally prepared engineering plans for a future expansion are also available, offering additional flexibility and value for future owners. Located in the sought-after community of Duck Key, just minutes from world-class boating, fishing, waterfront dining, and resort amenities. A rare opportunity to own a fully renovated luxury home in one of the Florida Keys' most desirable island communities.

209 Corsair Rd, Duck Key

$1,395,000
4 Beds 2 Baths 619542 MLS
Life on the water feels effortless at 34 Key Haven Road! Set along a wide canal in one of Key Haven's most desirable pockets, this 4 bedroom, 2 bathroom home is designed for those who want to be on the boat within minutes and back home just as easily. From the moment you arrive, the elevated setting and clean curb appeal set the tone. Step inside and the home opens up into a bright, modern layout where the kitchen naturally becomes the center of it all. With updated finishes and stainless steel appliances, it connects to both living areas, creating space to gather, relax, and entertain. As you move through the home, your attention is drawn toward the water. Sliding glass doors from both the main living area and primary bedroom lead to a spacious covered patio. Just a few steps down, the canal becomes an extension of your backyard, offering quick access to both the Atlantic and Gulf. The layout offers flexibility, including a fourth bedroom with its own entrance, ideal for guests, a home office, or additional privacy. Outside, a 60ft concrete seawall and generous dockage space make it easy to accommodate your boating lifestyle. With a metal roof, shutters, and an elevated lot helping to keep insurance costs very manageable, this is a home that blends practicality with the kind of lifestyle that makes the Keys so special. Simple, functional, and centered around the water, just the way it should be!

34 Key Haven, Key Haven

$1,395,000
617612 MLS
An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west and 1.25 acres of lush protected vegetation on-site. A former 2,700 square foot residence once occupied the site and was later demolished with permit in 2021 after sustaining damage during Hurricane Irma. A ROGO Exemption Letter is in place, eliminating the wait to build. A single family home permit application was submitted in 2022 and can potentially be reopened or transferred to a new owner with the County. The U.S. Army Corps of Engineers previously approved a 412 foot dock permit in 2019, offering tremendous potential for future dockage. Plans for a residence, ACOE documentation, and dock drawings (including a 16,000 lb boat lift) are available upon request. Zoned Improved Subdivision, one dwelling unit may be built with a twenty percent open space requirement. This rare acreage invites imagination, whether creating a luxury waterfront retreat, private family compound, or legacy estate to hold for generations. With unmatched open water views, bay bottom rights, ROGO exemption, and a location rarely offered, this is a blank canvas for an extraordinary Keys estate. A once in a lifetime opportunity to build now and craft your vision on one of the most unique properties available in the Lower Keys.

1261 Ave A, Big Pine

$1,390,000
2 Beds 2 Baths 616971 MLS
Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, 50 ft of coveted dockage, and boat slip with immediate bay access. Meticulously maintained and ready for carefree island living. The home's concrete, ground-level construction enhances both durability and ease of maintenance, while a fresh, clean aesthetic unfolds inside and out. Recent upgrades and improvements include brand new metal roof, impact windows and doors, new interior and exterior paint, new interior doors, energy efficient appliances, new sewer line, and re-thatched tiki hut. Updates to the attached pull through garage includes new door rollers, lock hardware, and upgraded flooring and wall finishes, all designed to keep the property in turnkey condition. This home is for those who embrace water-based recreation with easy bay and ocean access via Tavernier Creek, a boat slip with ramp through the garage, and new fish cleaning station with electric and water hookup. The voluntary homeowners association offers a bayfront HOA park with a new boat ramp, beach, and picnic area. With its ideal location and exceptional features, this canal home presents a unique opportunity to embrace the vibrant lifestyle of the Upper Keys.

251 Azalea St, Tavernier

$1,385,000
3 Beds 3 Baths 620283 MLS
Exclusive and seldom available offering in the gated community of Key Largo Yacht Club. Completely remolded turn key 3 Bedroom 3 Bath 2 Car garage with ocean views from all balconies. A deeded 30' Boat Slip that includes a 15,000 LB lift just steps from your door. This is a beautiful turn key unit completely furnished and decorated with no expense spared. The 1st level encompasses your own patio for entertaining and grilling. The 2nd level is all about the kitchen / dinning and living / family room experience. The 3rd level is completely dedicated to a magnificent primary suite with a large bathroom and walk-in closets. Located in a beautiful 10 acre secured / gated community of only 24 units this community includes a modern pool, club house, tennis / basketball courts and trailer parking and private boat ramp.

1501 Ocean Bay Dr Unit #10 - B7, Key Largo

$1,385,000
3 Beds 2 Baths 620016 MLS
Ocean Harbour condo with Atlantic ocean views and a boat slip in Islamorada. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space. The thoughtfully redesigned floor plan enhances the primary suite layout, adds a third bedroom, updates both bathrooms, and expands the living area by enclosing the porch as additional interior living space; maximizing functionality, comfort, and guest accommodations. Features updated appliances, hurricane impact glass, boat slip #33 and one covered parking space. Elevated waterfront living within this premier gated community featuring beach areas, oceanfront clubhouse, swimming pool, spa, gym, pickleball and tennis courts, EV charging station, boat ramp, and boat trailer storage. The beach tiki is ideal for entertaining with a grill, ice maker, and TV. Pets allowed with restrictions. Enjoy boating, fishing, kayaking, paddle boarding, nearby restaurants, medical care, boutique shopping, and art galleries. Bring your boat and experience the best of Florida Keys waterfront living.

87851 Old Hwy Unit M42, Islamorada

$1,375,000
4 Beds 3 Baths 620962 MLS
OPEN Saturday Aug 15 from 10-1! All this home needs is YOU! Located just one block in from the bay in Key Largo's popular Sexton Cove, this 2014 build offers 4 bedrooms, including an office/den/4th bedroom, 2.5 baths along with a laundry room and workshop! The spacious floorplan offers a nice sized living area with a proper dining space, and open kitchen with granite tops, wood cabinets and island for entertaining. The generous primary suite includes ample closet space & large en suite bath with shower, tub, dual sinks & water closet. With coveted Southeast exposure, the double decker covered porches overlook your 62ft concrete dock with davits and the 80ft wide canal - perfect for taking in the morning sunrise and afternoon cocktails! This solidly built home has been fortified with impact windows & doors, a metal roof and a new ac installed in 2026. Fully furnished down to the dishes along with a fully stocked workshop with a work bench, ice machine and more. Covered parking for 3 cars and tons of open space for your RV, boat trailer and even room for a pool! Sexton Cove offers a private boat ramp just down the street, membership is optional at just $150 per year. The 80ft wide, yet short canal offers direct access to the Florida Bay and the ocean beyond for excellent proximity to the world class fishing, boating and diving Key Largo is known for. Numerous bars & restaurants nearby that can be reached by car, foot or boat! Close enough to the mainland yet a world away.... call today and enjoy the beauty of Keys living!

3 Snipe Rd, Key Largo

$1,375,000
4 Beds 3 Baths 619317 MLS
WATERFRONT GEM. Located on Big Coppitt, this location is only five miles from Key West and all destination resort amenities, restaurants, and the downtown Historic District . Adjoined by 130' frontage of a deep canal and 80 feet of multi level concrete seawall, this Boater's paradise has quick access to the Key West Harbor, fabulous Coral Reef diving, offshore fishing and back country beaches, lobster diving and wrecks. An open floor plan with updated kitchen greets you upon entry of this elevated home. One ensuite bedroom and two additional guest bedrooms, share the second bath and laundry area round out the main floor. A large open composite deck faces the canal off the living area, providing over 400 sf of additional outdoor space. The third level is a master suite with large walk in closet and custom bath. The lower level includes a large 900 sf permitted storage area, covered parking for two vehicles from the paver driveway. Construction features include Hardi-board cement based siding and soffits, white metal roof, and plenty of yard for your toy storage, boat trailers, and guest parking. Plenty of Room for a pool and Tiki.

9 Jade Dr, Big Coppitt

$1,375,000
4 Beds 4 Baths 617821 MLS
Ocean Views! Over 2730 interior sq ft townhome with Ocean Views! This is the largest floor plan at SeaSide Court. Boasting 6 balconies - 4 bed - 4 bath - 3 levels over private garage. Only one other of these largest floor plans has come up for sell in the MLS in three years! Concrete construction with impact rated windows & doors gives you lock it & leave convenience. Features stainless steel kitchen appliances, two garden tubs & four showers. For your convenience it has trash and laundry chutes on multiple floors plus parking for three cars (one inside private garage, one in exclusive space outside the garage and one is in open parking around the pool). No attached unit on one side of this town home. On the ground level you have garage, interior storage, laundry room and covered area leading out to a secluded (fenced) courtyard. This is a great space for entertaining, dinning, bar area, etc... to enjoy our mild winter weather. Some owners in this community have built small, private pools in their court yards (this one does NOT have a private pool). Up on the roof you'll find a small, private roof top deck for enjoying sunrises, sunsets, star gazing or working on your tan! The SeaSide complex is gated, has two pools and a club house with weight / work out room. The private elevator goes from the ground level up to all three levels & has just been serviced. The roof-top deck is accessible from a 'ships ladder' only. Proof of funds or mortgage pre-qual required before showing and must accompany all offers. See documents tab for Assoc docs, budget, etc...

43 Seaside South Ct, Key West

$1,374,499
4 Beds 3 Baths 618156 MLS
Duck Key Pool Home with Legal Downstairs Living & Exceptional Flexibility. Beautifully updated 4BR/3BA pool home on the desirable island of Duck Key, thoughtfully renovated with permits and designed for comfortable coastal living. A standout feature of this home is the legal, permitted downstairs living area (pre-1973), which offers a private space complete with a living room, bedroom, bath, and kitchenette. This flexible layout is ideal for extended family, long-term guests, or creating a separate retreat within the home--an increasingly rare advantage in the Florida Keys. Upstairs, the main living area features updated finishes and generous closet space throughout, providing both comfort and functionality. The home is offered fully furnished and move-in ready, allowing for immediate enjoyment. Step outside to your own private tropical setting, featuring: a sparkling pool and tiki hut for entertaining; lush landscaping with pineapple, fig, starfruit, and avocado trees; a private putting green; and partial Atlantic Ocean views. Additional highlights include two attached garage spaces and access to a voluntary homeowners clubhouse. Conveniently located near Duck Key Marina and Hawk's Cay Resort amenities, with optional memberships available. A rare opportunity to own a versatile, move-in-ready home in one of the Florida Keys' most sought-after communities. Check out the marina and the perks of being a homeowner on Duck Key. https://www.duckkeymarina.com/ for boat slips, https://hawks-cay-resort.playbypoint.com/f/hawks-cay-resort/memberships, https://www.hawkscay.com/, and http://www.clubduckkey.com/ for memberships! All in your backyard.

247 W Seaview Cir, Duck Key

$1,350,000
4 Beds 5 Baths 620612 MLS
THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

1503 Atlantic Blvd, Key West

$1,350,000
3 Beds 2 Baths 618944 MLS
THIS IS FLORIDA KEYS LIVING AT ITS BEST!! Truly a Tropical Oasis, this Stunning 3 Bedroom 2 Bath Key Largo canal front retreat on a large corner lot with 65 feet of concrete dock and quick, one minute access to the Bay and Ocean thru Adams Cut will impress!! This 2006 impeccable home with all the modern luxuries you could want features gorgeous hard wood floors throughout. The open concept living area is beautifully presented with soaring vaulted ceilings, a huge kitchen island for entertaining, stainless-steel appliances and motorized window treatments and plantation shutters! Step into your spacious primary bedroom and enjoy a spa like bathroom where you can unwind and relax. Downstairs you will find a very large patio perfect for Sunday afternoon BBQ's with friends and family. The 65' concrete dock is equipped with a 15,000 lb boat lift and davits. Plenty of room for your water toys here!! This home has it all for the boating enthusiast! LOCATION! LOCATION!! Conveniently located in Lake Surprise, MM 106 Bayside. Absolutely one of Key Largo's premier neighborhoods, close to shopping, amazing restaurants and outdoor fun. A 20-minute drive to the mainland makes this home a perfect choice for those seeking the best of both worlds! Long Key Road is the first canal in from Blackwater Sound, you'll be out on the water in seconds. Don't miss this opportunity to own this stunning canal front home in Lake Surprise.

103 Long, Key Largo

$1,349,000
3 Beds 2 Baths 620916 MLS
Look no further--this exceptional property truly has it all. This beautifully maintained CBS home boasts open-water views and is situated on an oversized lot on an extra-wide, deep canal, great for bigger boats, and just three houses in from the end. You'll be up on plane in seconds, with unparalleled boating access to both the Atlantic and Gulf. Ideally located closest to the premier backcountry of the Lower Florida Keys, this is the perfect property for the fishing and diving enthusiasts and still only 20 minutes to Key West. Built by Tom Ryan Construction, this solid CBS 3-bedroom 2-bath home is almost 1,300 square feet, and has a spacious, open feel, created by the thoughtful layout and vaulted ceilings in the main living area. The kitchen features granite countertops, a convenient breakfast bar, and a dedicated dining area, making it ideal for both everyday island living and entertaining. The primary suite has a walk in closet and french doors leading out to the porch, while the second bedroom has a pocket door creating another convenient ensuite for guests. Most days you'll enjoy outdoor dining or cocktails and the relaxed island life from the covered, screened porch overlooking the canal with open water views of Kemp Channel. The views continue into the primary suite and kitchen, offering a beautiful waterfront backdrop throughout the home. The lower enclosure provides plenty of space for a vehicle, workshop, and storage. Two 500-gallon cisterns provide ample water for maintaining the lush tropical landscaping. The solid concrete step down seawall features davits each with a 5,500 lift capacity. This property is the ideal location to be able to spend a stellar day on the water, then head to Key West to one of the many fabulous restaurants for dinner, and finish the evening listening to live music or take in a show at one of our unique boutique theaters. You can have it all.

23057 Bluegill Ln, Cudjoe

$1,349,000
2 Beds 2 Baths 620478 MLS
Turnkey and income-producing, this beautifully updated waterfront half-duplex is the perfect opportunity to own a slice of paradise while continuing its successful vacation rental legacy. Ideally situated on a quiet canal with stunning water views in the highly desirable Key Colony Beach, this 2-bedroom 2-bath stilted CBS construction half-duplex offers the ideal blend of relaxation, boating, and investment potential. Inside you will find vaulted ceilings, abundant natural light, and coastal-inspired decor. With beautiful water views from the kitchen, dining, and living area. Step outside to your private tropical oasis featuring a new 50' dock with quick access to the open water, a fish cleaning station, and multiple outdoor entertainment areas. Don't miss out on the rare opportunity to own a high-performing vacation rental with stunning water views on beautiful Key Colony Beach.

101 N Coral Ln, Key Colony