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3674 S Seas St, Big Pine
$859,000
2 Beds ⋅ 2 Baths ⋅ 619841 MLS
Set in the peaceful, natural surroundings of Port Pine Heights, this thoughtfully updated home offers the relaxed, unhurried lifestyle that makes this Lower Keys community so desirable. Over $100,000 has been invested in updates and improvements, allowing the next owner to enjoy a beautifully refreshed home without the time, expense, and uncertainty that often come with renovating. Recent updates include a reimagined kitchen layout with new cabinetry and quartz countertops, beautifully renovated bathrooms with tiled showers and new vanities, new composite decking with sleek aluminum railings. The screened porch has been upgraded with micro-mesh screening, while fresh interior and exterior paint, updated fixtures, and thoughtful finishing touches complete the improvements throughout. Boaters will appreciate the quick, convenient access to Pine Channel and Contents Key, making days on the water easy to enjoy. This home also offers an impressive 702 sq. ft. of fully air-conditioned storage space below, providing exceptional flexibility for storage, hobbies, gear, or additional workspace. Move-in ready, thoughtfully updated, and wonderfully connected to the laid-back beauty of island living.

3674 S Seas St, Big Pine

4 Coral Dr, Saddle Bunch
$450,000
2 Beds ⋅ 2 Baths ⋅ 619836 MLS
Affordable Living in the Florida Keys Has Arrived! Welcome to this charming 2-bedroom, 2-bathroom home offering comfortable living space, an open-concept layout, and inviting outdoor areas perfect for dining, entertaining, or simply enjoying our beautiful Florida Keys lifestyle. Step inside to a bright and open living room and kitchen just off the front entry. Both bedrooms are privately situated toward the back of the home. The Primary bedroom includes direct access to the backyard area, an ensuite bathroom with walk-in shower, and plenty of closet/storage space. Qualified buyers may have the opportunity to assume the current mortgage, VA and FHA buyers this home is a must see. Additional highlights include ample parking, a great neighborhood, and a convenient location just minutes from Bay View Park, Baby's Coffee, the famous Sugar Shark Market, and NAS Key West on Boca Chica. Come see this home now, at this price, this one will not last long!!

4 Coral Dr, Saddle Bunch

22939 Gasparilla Ln, Cudjoe
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 619835 MLS
Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.

22939 Gasparilla Ln, Cudjoe

88835 & 88845 Old Hwy, Tavernier
$40,000,000
8 Beds ⋅ 11 Baths ⋅ 619826 MLS
A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatched combination of scale, privacy, and future development flexibility in the Florida Keys. At 88845, a newly constructed 8,200SF estate sets a new standard for modern coastal luxury. Thoughtfully designed for both grand entertaining and private retreat, the residence offers 5 bedrooms, 6 full baths & 2 half baths, complemented by a dedicated office, control room, mudroom, and expansive 3-car garage with climate-controlled workshop. Interior finishes are curated at the highest level, including white diamond marble, teak wood flooring, custom millwork & a vapor fireplace, while a full-home sound system, elevator & advanced mechanical infrastructure provide seamless functionality. The chef's kitchen is equipped with top-tier Wolf, SubZero, & Cove appliances, dual dishwashers, farmhouse sinks, refrigerated drawers, wine storage & custom mahogany countertops-designed to accommodate both everyday living and large-scale entertaining. Outdoor living is equally impressive, anchored by a 120-foot resort-style pool with integrated spa, heating & chilling systems, & full smart control. A fully equipped summer kitchen, cabana bath, & multiple covered terraces create a true waterfront lifestyle experience. With 480 feet of water frontage, the protected basin offers exceptional boating capabilities, including 90 feet of dockage & room to expand, a 20,000lb lift, boat ramp & deep-water access. The adjacent parcel at 88835 provides over 3 acres of additional opportunity featuring a renovated 3-bedroom residence completed in 2022, with a transferable TDR allowing for the development of a substantially larger primary home. The property also includes a buildable lot & natural hammock buffer for added privacy. Together, these two properties present a generational opportunity to own a one of a kind waterfront compound.

88835 & 88845 Old Hwy, Tavernier

88845 Old Hwy, Tavernier
$27,000,000
5 Beds ⋅ 8 Baths ⋅ 619825 MLS
Set on over 2 acres along prestigious Millionaire's Row in Tavernier, this newly constructed oceanfront estate represents a rare convergence of scale, design, and functionality in the Upper Florida Keys. Encompassing 8,200 square feet of interior living space and over 16,000 square feet total, the residence is thoughtfully designed to accommodate both elevated everyday living and large-scale entertaining.The home features 5 bedrooms, 6 full baths, and 2 half baths, with all bedrooms offering en suite accommodations, custom closet build-outs, and refined finishes throughout. Additional interior spaces include a dedicated office, control room, mud room, and laundry room, providing both comfort and operational efficiency. A private elevator, whole-home sound system, and advanced mechanical infrastructure--including 600-amp service, multiple electrical panels, and five independent AC zones--underscore the property's level of detail and performance. Interior finishes are curated with a modern coastal aesthetic, highlighted by white diamond marble and teak wood flooring & a custom steel roof. The chef's kitchen is outfitted with top-tier Wolf, SubZero, and Cove appliances, including a 60-inch range, dual dishwashers, farmhouse sinks, and custom mahogany countertops--designed to seamlessly blend form and function. Outdoor living is equally exceptional, with 240 feet of oceanfront, anchored by a 120-foot resort-style pool, complete with multiple heating and chilling systems, a gas-heated spa, and full smart control. A fully equipped summer kitchen, cabana bath, and multiple covered entertaining areas create a true indoor-outdoor lifestyle experience. Additional highlights include a 3-car garage and fully equipped workshop with air conditioning, utilities, security systems, and custom lighting. The property is also zoned for weekly rentals, presenting a compelling opportunity for both personal enjoyment and income potential.

88845 Old Hwy, Tavernier

88835 Old Hwy, Tavernier
$15,000,000
3 Beds ⋅ 3 Baths ⋅ 619824 MLS
An exceptional opportunity on coveted Millionaire's Row in Tavernier, 88835 Old Highway offers over 3 acres of oceanfront property paired with a rare additional acre featuring a protected boat basin--delivering a unique blend of privacy, usability, and future potential in the Upper Keys. Completed in 2022, the existing 3-bedroom, 3 bath residence spans approximately 1,500 square feet and is thoughtfully designed with impact windows and doors, hardwood flooring, a steel metal roof, and a well-appointed kitchen featuring Viking appliances. Outdoor living is enhanced by shell stone porch flooring, covered parking, and professionally designed landscaping with turf for low-maintenance coastal living. The property is comprised of three distinct parcels, including a buildable lot (Lot 2A), the current homesite (Lot 2), and a natural hammock parcel (Lot 3A) that serves as a permanent privacy buffer from the road, preserving the integrity and seclusion of the estate. A highly valuable feature of this offering is the inclusion & rare opportunity to create a custom waterfront compound tailored to your vision, while maintaining immediate livability. With direct access to a private boat basin and expansive acreage rarely found in the Keys, 88835 Old Highway represents a compelling combination of current enjoyment, future development flexibility, and long-term value in one of the area's most desirable waterfront corridors.

88835 Old Hwy, Tavernier

100 Morris Ln Unit C13, Key Largo
$190,000
619819 MLS
PRICE REFLECTS $40,000 BELOW MARKET X WRECKAGE REMOVAL EXPENSE CONSIDERED! 38' boat deepwater dock slip (C13) at Manatee Bay Yacht Club, a private gated island marina. Located on border between Miami Dade and Monroe counties the marina is less than an hour from Miami downtown yet it's in the Keys. Access to the intracoastal and Atlantic ocean. Marina is well protected and considered a local hurricane hole. Amenities include sandy beach, boat ramp, pool, hot tub, laundromat, ice machine, toilets and showers. The slip comes with a private tiki-hut, dock box, and two parking places directly at the slip. The aluminum dock has water and electric hookup. 6-8ft draft. Brackish water is easy on the boat and restricts bottom growth. HOA $675 paid every(90 days) covers grounds, dock, and facilities maintenance, marina staff, water, sewage. Electricity is metered. Liveaboard ok. RV parking is not allowed. Airbnb/VRBO rental is not allowed. As-Is PRICED TO SELL well below market value *Submerged vessel currently onsite; vessel to be removed and funded by BUYER. Photos depict potential boat slip condition and may not reflect the current presence of the submerged vessel.

100 Morris Ln Unit C13, Key Largo

325 Calusa St Unit # 345, Key Largo
$417,000
1 Beds ⋅ 1 Baths ⋅ 619807 MLS
Own Your Own Piece of Paradise in Key Largo! Welcome to your slice of the Florida Keys, located in a desirable private, gated community in beautiful Key Largo. This amenity-rich neighborhood offers everything you need for both relaxation and recreation, including 24-hour security, a private boat ramp, children's park, basketball courts, tennis courts, racquetball and pickleball courts, laundry rooms and a community pool One of the standout features of this community is that it is among the few in Key Largo that allow short-term rentals, making this property not only a personal getaway but also an excellent income-producing investment opportunity. Situated on a desirable corner lot, this property includes a 2022 Forest River Grand Lodge featuring 1 bedroom, 1 bathroom, and two upstairs lofts, providing ample space for guests. The lot is large enough to accommodate all your toys, a large boat and jet ski-perfect for enjoying the Keys lifestyle. Additional highlights include: • Washer and dryer • Shed • Access to a recreation hall available for private events and gatherings Whether you're looking for a vacation home, an investment property, or both, this is a rare opportunity to own in one of Key Largo's most sought-after communities.

325 Calusa St Unit # 345, Key Largo

148 Iroquois St, Tavernier
$999,000
4 Beds ⋅ 3 Baths ⋅ 619796 MLS
Spacious 4 bed, 3 bath home in the desirable Indian Mound neighborhood on Plantation Key. Sitting on two lots totaling about 11,000 sq ft, there's plenty of privacy and extra space to enjoy. As you enter, you're welcomed by a large, open floor plan with high ceilings, giving the home a bright and airy feel. The kitchen features granite countertops, upgraded stainless steel appliances, and high-output tankless water heater with instant hot water. Tile flooring runs throughout the main level, with carpet upstairs. Just off the living room, there's a large screened-in outdoor space that's perfect for relaxing or entertaining. This ground-level, above-flood CBS home was built in 2010 and includes a metal roof, impact windows and doors, split-zone A/C, and ceiling fans throughout. It offers 2,361 sq ft of living space, along with exterior lighting and a fenced backyard. Located at 148 Iroquois St and close to local schools, it's a great option for anyone needing both space and convenience. The oversized lot gives you room for kids, pets, or even future additions, while the fenced yard adds an extra layer of privacy. The neighborhood also offers a boat ramp, making it easy to enjoy everything the Keys lifestyle has to offer.

148 Iroquois St, Tavernier

205 Stirrup, Marathon
$2,249,000
4 Beds ⋅ 3 Baths ⋅ 619793 MLS
Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

205 Stirrup, Marathon

27215 Mariposa Rd, Ramrod
$799,999
3 Beds ⋅ 3 Baths ⋅ 619792 MLS
NEW CONSTRUCTION! This charming 1,500 sqft home is a true retreat, perfectly positioned in the Lower Keys, just a moments walk from the popular Looe Key Tiki Bar and Boondocks restaurants. Tucked away in a quiet, low-traffic neighborhood, this property offers the ideal combination of peace and convenience, allowing you to embrace the relaxed Keys lifestyle. Inside, you'll find: A spacious, open floor plan that provides ample room to customize and make it your own. Effortless flow between the indoor living areas and the outdoor spaces, making it easy to take full advantage of Florida's year-round sunshine. A huge covered side porch great for entertaining and catching afternoon breeze! Additional features include: A newly constructed home built to the latest codes, ensuring lower insurance rates and added protection from tropical weather. This property seamlessly blends comfort, convenience, and the laid-back Florida Keys lifestyle. Seller's contractor can install pool and downstairs full sized garage, ask for details in pricing. Plans for both already obtained, and permit can be started right away. 12x22 Pool quote for $60,000! 1100 sqft garage for $30,000! Plugged swimming canal, no boating. Tenant occupied, please allow notice to schedule showings. Seller is licensed FL real estate agent.

27215 Mariposa Rd, Ramrod

no property photo
$325,000
619791 MLS
A rare opportunity awaits on Little Torch Key with this 6,000 sq. ft. vacant lot, offering the perfect canvas for your Florida Keys dream home. Located in a desirable Tier 3 building area, this property provides a smoother permitting path while still delivering the privacy and tranquility that make the Lower Keys so special. The lot is partially cleared, giving you a head start on site preparation while preserving the natural beauty of the island landscape. From the property, enjoy a subtle peekaboo view of the Gulf, where shimmering waters hint at the peaceful coastal lifestyle just beyond your doorstep. Whether you envision a tropical retreat, a full-time residence, or an investment build, this parcel places you minutes from world-class boating, fishing, and the laid-back charm of the Lower Keys. With its location, buildability, and gentle water views, this Little Torch Key lot is a standout opportunity in one of the most sought-after island communities.

Trinidad Ln, Little Torch

617 Front Unit D-54 Penthouse Week 37, Not Provided
$26,000
2 Beds ⋅ 2 Baths ⋅ 619789 MLS
Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Located just steps from the rooftop terrace, this unit also provides easy access to some of the best sunset views in Key West. Week 37 offers an ideal getaway, featuring warm weather, fewer crowds, and a relaxed island atmosphere. This condo is nestled in the heart of Old Town, just two blocks from Duval. And right next to the Historic Seaport Key West Marina. Walk downstairs or take the elevator to enjoy the Galleon's on-site Tiki bar with live music, the Pirates Cove restaurant, a private beach, a heated in-ground pool and hot tub, an exercise room, and a built-in BBQ grill. The Galleon resort also offers fantastic raffles for owners and daily poolside bingo. Place your unit with the on-site Galleon Concierge Management and place it in the rental pool. Rental prices for a 2-bed, 2-bath unit this week are approximately $3,885 to $ 6,195 per week. Dues are $1,585 (2025) paid annually, and taxes are approximately $262 per year. So, for less than $2K a year, stay at this incredible resort and enjoy for yourself, or rent it out. Jet skis and bikes are available on-site for rent. The week includes 1 unassigned parking space. This is a great opportunity to own a deeded week at an exceptional, highly rated resort! Photos of a similar penthouse unit, not the exact unit offered.

617 Front Unit D-54 Penthouse Week 37, Not Provided

325 Calusa St Unit # 81, Key Largo
$399,990
2 Beds ⋅ 2 Baths ⋅ 619785 MLS
Close to the pool, close to the beach, close to everything in popular Calusa Campground! This 2 bedroom Park model RV has been thoughtfully remodeled for comfort with a tiled shower, ice cold a/c, vinyl flooring & more. Huge metal overhang covers a tiled area perfect for outdoor living - including a tv, refrigerator & casita with kitchen & another full bath. There is plenty of parking onsite for your boat, golf cart and/or your vehicle under canopy. Another shed houses a full sized washer & dryer along with plenty of storage. Bayfront Pool, boat ramp, playground, club house, tennis, basketball courts & now a food truck is just a short walk away. Take in nightly sunsets from the beautiful Bayfront common area. Gated Calusa Campground has no rental restrictions - giving you tons of flexibility and revenue potential for AirBnB etc. Ideally located in the heart of Key Largo close to the new Publix, Tj Maxx, dining, fishing, diving and more! Best kept secret in Key Largo! Your getaway awaits!

325 Calusa St Unit # 81, Key Largo

107 Tavern Dr, Tavernier
$530,000
2 Beds ⋅ 1 Baths ⋅ 619783 MLS
In the heart of Historic Tavernier, this charming Keys cottage offers the kind of character that's getting harder and harder to find. Set on two lots with peekaboo ocean views, the property combines Old Florida charm, outdoor space, and boating convenience in one inviting package. Inside, the two bedroom, one bath home has a cozy, authentic Keys feel. This compact space is full of personality. Outside, a cute deck overlooks the above-ground pool, creating a relaxed setting for morning coffee or afternoon swims. The double lot provides extra breathing room and possibilities that are rare in this area. Located near a neighborhood boat ramp, you'll enjoy easy access to the water and the laid-back lifestyle that makes Tavernier so special. Plus, you're just minutes from great dining, shopping, and everyday essentials--because island living should feel effortless. Nearby local favorites include Cafe Moka, Old Tavernier Restaurant and Sunrise Market. Whether you're looking for a weekend getaway, a full-time cottage, or a property with classic Florida Keys charm, this one stands out.

107 Tavern Dr, Tavernier

437 Laguna Ave, Key Largo
$2,950,000
4 Beds ⋅ 4 Baths ⋅ 619782 MLS
Island living in prestigious Port Largo, one of Key Largo's most sought-after waterfront neighborhoods. Set on an oversized 14,215 sq. ft. waterfront lot, this furnished and move-in-ready pool home offers 50' of concrete dockage with boat lift and jet ski davits, deep-water ocean access, and exceptional space for enjoying the Florida Keys lifestyle. The home offers 4 bedrooms and 4 baths, including 2 primary suites. The owner's suite encompasses the third floor and features a private balcony retreat and spacious bath with soaking tub, separate shower, dressing table, and spa-like feel. On the main living level, a well-appointed kitchen features ample wood cabinetry, granite countertops, and stainless-steel appliances. A large outdoor balcony extends the living space and provides an inviting setting for morning coffee, coastal breezes, dining, or relaxed evenings. The expansive, fully fenced and gated yard is a standout feature, with a heated pool, generous covered outdoor areas, and plenty of room to entertain family and friends after a day on the water. A ground-level recreation room opens directly to the pool area, while 2 attached garages provide valuable storage and convenience--a rare find in the Keys. Ideally located near restaurants, shopping, Key Largo Community Park, and Jacobs Aquatic Center. With its oversized lot, waterfront setting, abundant outdoor space, and boating amenities, 437 Laguna Avenue offers a distinctive opportunity to enjoy the Keys lifestyle in Port Largo.

437 Laguna Ave, Key Largo

901 S Emerald Dr, Key Largo
$650,000
2 Beds ⋅ 2 Baths ⋅ 619780 MLS
LOVELY 2/2 HOME! WITH AN OVERSIZED CORNER LOT IN AN ABOVE FLOOD ''X'' ZONE. LOCATED IN SILVER SHORES AN ''OVER 55'' FULLY GATED COMMUNITY. THIS HOME COMES FULLY FURNISHED AND IT'S THE RIGHT SIZE FOR AN EXTENDED FAMILY OR GUESTS VISITING. IT HAS A LOVELY SUNROOM/FAMILY ROOM, PLUS THERE IS PLENTY OF ADDITIONAL PARKING ON THE REAR OF THE HOME TO PARK YOUR BOAT OR WATER TOYS. THE KITCHEN AND BATHROOMS HAVE BEEN TASTEFULLY UPDATED! SILVER SHORES FEATURES A 70' HEATED AND CHILLED POOL, TENNIS, BOCCE, SHUFFLEBOARD COURTS, PLUS A SMALL BOAT RAMP. THERE ARE PLENTY OF FUN ACTIVITIES, PARTIES, AND EVENTS, YOU WILL LOVE LIVING IN SILVER SHORES ON A FULL TIME, PART TIME, OR ON A SEASONAL BASIS. THE HOA NOW OWNS THE LAND AND LEASE. THE SELLERS HAVE PAID THE ENTIRE $81,791.82 AMOUNT OF THE SPECIAL ASSESSMENT. ONCE SILVER SHORES BECOMES A CONDOMINIUM ASSOCIATION A ''FEE SIMPLE'' DEED WILL BE ISSUED FOR YOUR PARCEL.

901 S Emerald Dr, Key Largo

112 Peace Ave, Tavernier
$769,000
4 Beds ⋅ 2 Baths ⋅ 619775 MLS
Located in the heart of Tavernier, ideally situated between Key Largo and Islamorada, this well appointed four bedroom, two bath home offers a blend of comfort, functionality, and relaxed outdoor living. The spacious downstairs garage and storage area present exceptional flexibility, ideal for multiple uses from hobby space to additional storage for boating and recreational gear. The fully fenced backyard, finished with low maintenance synthetic turf, creates a private setting with ample room to entertain or unwind, and space to add a pool if desired. The outdoor accommodations are elevated further with a fully equipped kitchen featuring a grill, refrigerator, sink, smoker space, and integrated sound system. Upstairs, a screened patio overlooks the backyard and opens to a serene nature preserve, offering a peaceful, private backdrop. Inside, the home features high end stainless steel appliances, a propane stove, and a thoughtful list of recent upgrades, including renovated bathrooms with new plumbing, new interior paint, a newer AC system, and a tankless water heater. A new washer and dryer add everyday convenience. Additional highlights include a 220-volt outlet and water access outside the garage, ideal for an ice machine or further customization. With additional covered parking for a boat trailer or RV on the side of the home, this property offers a practical yet elevated lifestyle in a prime Upper Keys location. Seller financing possible, inquire for details.

112 Peace Ave, Tavernier

591 Sombrero Beach Rd Unit APT 1B, Marathon
$684,000
2 Beds ⋅ 3 Baths ⋅ 619770 MLS
Perfectly positioned just steps from the pristine shores of Sombrero Beach, premier shopping, and vibrant nightlife, Lemon Cove stands in a class entirely its own. No other condominium residence in the area offers such a rare combination of generous private parking, breathtaking canal frontage, impeccably manicured grounds, and a resort-style pool -- all seamlessly curated for the discerning buyer. This exceptional 2-bedroom, 2.5-bathroom canal-front residence commands sweeping views of both the sparkling pool and tranquil canal, framed by generously proportioned living spaces and refined, upscale finishes throughout. Every detail has been thoughtfully considered, offering an effortless lifestyle where luxury and low-maintenance living exist in perfect harmony. For those who have envisioned waking each morning to the serene beauty of waterfront living -- without compromise -- this is your moment to live near the beach!

591 Sombrero Beach Rd Unit APT 1B, Marathon

331 Ave F, Big Coppitt
$775,711
4 Beds ⋅ 2 Baths ⋅ 619768 MLS
Live the Florida Keys lifestyle in this character-filled 4-bedroom, 2-bath home on Big Coppitt Key, approximately 10 minutes from Key West. With 1,415 square feet and two distinct living areas, the home offers exceptional flexibility for visiting family and friends, a home office, or simply room to spread out. An assumable mortgage with an approximate balance of $468,000 at 2.375% may be available, subject to lender approval and buyer qualification. The freshly updated kitchen features warm butcher-block countertops, a deep stainless-steel sink, subway-tile backsplash and stainless-steel range hood. Central air conditioning, tile floors and thoughtful improvements throughout make the home comfortable and ready to enjoy. Each living area has its own outdoor space, while the 4,900-square-foot lot provides generous off-street parking on a spacious paver driveway--ideal for multiple vehicles, a boat and the Keys lifestyle. Built in 1933, this home has experienced an island journey unlike most. Its story began with a connection to housing at the former Key West Naval Seaplane Base, part of the area's rich military and maritime past. In the 1960s, the structure made its way from Key West to Big Coppitt Key, beginning its new chapter on Avenue F. Today, that history is paired with a renewed coastal-cottage appearance featuring Bahama-style shutters, tropical landscaping and welcoming outdoor spaces. Two nearby neighborhood parks offer a playground, basketball court, outdoor fitness equipment, picnic areas and open green space. A convenient public boat ramp close to home provides boat-trailer parking and easy water access. Whether you are seeking a full-time Keys residence, seasonal island retreat or flexible home with room for family and guests, 331 Avenue F offers history, character and everyday access to the best of Lower Keys living.

331 Ave F, Big Coppitt

301 Buttonwood Cir Unit B, Key Largo
$3,950,000
5 Beds ⋅ 5 Baths ⋅ 619766 MLS
Stunning brand-new custom modern home with just the right amount of Keys flair, where no detail was overlooked from design to layout to finishes. Enter through a private electric gate onto this beautifully positioned corner lot, featuring covered parking, a lavish pool and hot tub, and a fully equipped outdoor kitchen, all surrounded by pristine, thoughtfully designed landscaping. A grand foyer welcomes you in, complete with a private elevator providing seamless access to every level. Designed with entertaining in mind, the home offers expansive living and dining spaces anchored by a gourmet kitchen, all flowing effortlessly into the outdoor areas to create the ultimate indoor-outdoor lifestyle. Boat lift included in the sale! The primary suite is a true retreat, featuring a spacious private balcony, a luxurious spa-style bathroom with soaking tub and separate shower, and a large walk-in closet. Four additional bedrooms, each with their own ensuite bathrooms, carry the same high level of craftsmanship and attention to detail throughout. Crowning the home is a rooftop deck with amazing ocean views, perfect for entertaining guests or enjoying a quiet, romantic evening. Come experience the quality, design, and thoughtfulness of this exceptional home for yourself.

301 Buttonwood Cir Unit B, Key Largo

301 Buttonwood Cir Unit A, Key Largo
$3,750,000
5 Beds ⋅ 5 Baths ⋅ 619767 MLS
Stunning brand-new custom modern home with just the right amount of Keys flair, where no detail was overlooked from design to layout to finishes. Enter through a private electric gate onto this beautifully positioned corner lot, featuring covered parking, a lavish pool and hot tub, and a fully equipped outdoor kitchen, all surrounded by pristine, thoughtfully designed landscaping. A grand foyer welcomes you in, complete with a private elevator providing seamless access to every level. Designed with entertaining in mind, the home offers expansive living and dining spaces anchored by a gourmet kitchen, all flowing effortlessly into the outdoor areas to create the ultimate indoor-outdoor lifestyle. Boat lift included in the sale! The primary suite is a true retreat, featuring a spacious private balcony, a luxurious spa-style bathroom with soaking tub and separate shower, and a large walk-in closet. Four additional bedrooms, each with their own ensuite bathrooms, carry the same high level of craftsmanship and attention to detail throughout. Crowning the home is a rooftop deck with amazing ocean views, perfect for entertaining guests or enjoying a quiet, romantic evening. Come experience the quality, design, and thoughtfulness of this exceptional home for yourself.

301 Buttonwood Cir Unit A, Key Largo

103 52nd St, Marathon
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 619765 MLS
Welcome to Casa Sirena, a refined waterfront retreat in Marathon offering comfort, privacy, and strong investment appeal. Seller Financing available! This five bedroom, three bath home includes a convenient outdoor pool bath and is ideally positioned with water frontage on two sides. Boaters will appreciate 100 feet of durable composite dockage, a jet ski lift, and a private boat ramp shared with just one neighbor. The home enjoys close proximity to Boot Key Harbor, with easy access to waterfront dining by boat, as well as a straightforward route to the Gulf via Knight Key Channel and immediate Ocean access. The surrounding Vaca Key and Boot Key provide a natural buffer, offering added protection from the elements. Outdoor living is central to the property, with lush tropical landscaping, a saltwater pool, tiki hut, and expansive wraparound patios accessible from all rooms. Inside, the open floor plan connects the living, dining, and kitchen areas, creating a comfortable and functional space. The kitchen is equipped with high end appliances suited for everyday use or hosting. Additional features include a spacious two car garage with ample storage, an extra washer and dryer, refrigerator, freezer, and workbench. The home is offered fully furnished and turnkey, ready for personal use or as a vacation rental. Privacy fencing, a security system, and gated dock and ramp access complete the offering.

103 52nd St, Marathon

29562 Saratoga Ave, Big Pine
$1,435,000
4 Beds ⋅ 2 Baths ⋅ 619761 MLS
Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and furnishings are negotiable in the sale. This elevated, solid concrete home offers quick access to both the Ocean and Gulf, just minutes from world-class adventures! Designed with the serious boater in mind, the property features a 75' concrete seawall, a 17k lb. boat lift, fish-cleaning station, and step-down dock for easy loading. This expansive 4-bed, 2-bath home is ideal for entertaining, with oversized common areas that flow seamlessly for memorable gatherings. The third-floor loft, currently used as a bonus bedroom, offers 360-degree views and a private retreat, while main-floor bedrooms are generously sized with walk-in closets for ample storage. The kitchen is well appointed with a double oven, sprawling counter space, walk-in pantry, and room to host with ease. Unique details throughout include a custom etched mirror in the primary bath that adds coastal charm. Step outside and embrace the Keys lifestyle! A spacious porch, accessible from both the living area and primary suite, is perfect for open-air dining and relaxing water views. Downstairs, the ultimate entertaining area includes a full bar with TV, a large swim spa, plus a 500 lb. ice machine and bait freezer for added convenience. The thoughtfully landscaped yard offers privacy and function, boasting a fenced backyard and ample space for RV or trailer storage. Covered parking provides unique, direct interior access out of the elements. Located in a quiet neighborhood close to dining and shopping, this home blends tranquility with convenience. It is more than a home; it is a waterfront escape ready to be enjoyed!

29562 Saratoga Ave, Big Pine

1911 Seidenberg Ave, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619758 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West

12a-14a 12th Ave, Stock Island
$3,100,000
7 Beds ⋅ 4 Baths ⋅ 619753 MLS
Some opportunities require no explanation and this is one of them. A12, A13, and A14 12th Avenue sit side by side on Stock Island's waterfront, combining for 120 feet of canal frontage across three 4,800-square-foot parcels. A12 is set on 4,800 square feet with 40 feet of direct canal frontage. The three-bedroom, two-bath home was thoughtfully designed for the way people actually live in the Keys. It features ample outdoor space, multiple seating areas, and the kind of privacy that's harder to find than square footage. A13 features four-bedrooms & three bathrooms + private dock. A generous layout that offers flexibility for family & guests. A14 is the adjacent ROGO exempt lot. Two private docks. 120 feet of waterfront. 2 dwellings + a ROGO-exempt lot ready for your vision.

12a-14a 12th Ave, Stock Island

13a-14a 12th Ave, Stock Island
$2,100,000
4 Beds ⋅ 3 Baths ⋅ 619752 MLS
80 Feet on One Of The Deepest Canals in the 33040 Zip Code. A13 and A14 12th Avenue sit side by side on Stock Island's waterfront, combining for 80 feet of canal frontage across two 4,800-square-foot parcels. A13 is an 1,820-square-foot CBS home that features four-bedrooms, three bathrooms home with a private dock on one of the deepest canals in the 33040 zip code. The layout offers flexibility for a primary residence, vacation retreat, or investment property. A14, the adjacent lot (currently land only and notably ROGO exempt) is a blank canvas. Most naturally positioned as an expansion of A13: a pool or a guest cottage, an enhanced outdoor living space, the world is your oyster. For those thinking bigger: this property is also available as part of a package offering 120 feet of canal frontage with a 6-foot draft. See listing for details. For those thinking even bigger; this property is also available as part of a package offering 120 feet of canal frontage. See listing #619753 for details.

13a-14a 12th Ave, Stock Island

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