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240-250 11th St, Key Colony
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 621805 MLS
Two residences, two private pools, and 75 feet of dockage--an inviting combination of space, privacy, and waterfront living in Key Colony Beach. This full duplex brings family and friends together while maintaining the independence of two separate homes. Each offers two bedrooms, two bathrooms, and a generous 1,075 square feet, plus a private entrance, carport, and laundry. Inside, Old Florida character meets modern comfort. Vaulted wood ceilings grace the living, dining, and kitchen areas, while original terrazzo floors in one residence offer a nostalgic nod to the Keys of yesteryear. Updates in 2024-2025 include refreshed kitchens and fully renovated bathrooms with a modern coastal feel. Both backyards have been transformed into private tropical retreats, each with its own pool, tiki hut, bar/cabana area, and 37.5 feet of dockage. A connecting gate keeps the outdoor spaces private or opens them for gatherings. Oceanside boating with convenient Gulf access via nearby Vaca Cut. Ideal for extended families and friends sharing a Keys getaway, with room to enjoy one residence while renting the other--or rent both when away. Introduced to the vacation rental market in early 2025, the property has generated and booked $167,000 in 2026 gross rental revenue, with six weeks reserved for owner use. And then there's the location. Just a two-minute walk to Sunset Park, with restaurants and other island amenities an easy walk or bike ride away. A property that brings together the best of Keys living--time on the water, space for family and friends, and the flexibility to enjoy it on your own terms.

240-250 11th St, Key Colony
2827 Harris Ave, Key West
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 621768 MLS
This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

2827 Harris Ave, Key West
86 S Airport Dr, Summerland
$2,195,000
3 Beds ⋅ 3 Baths ⋅ 621715 MLS
RARE RUNWAY-TO-REEF LIVING Fly in. Boat out. Live the Florida Keys lifestyle few properties can offer. At 86 S Airport Drive on Summerland Key, aviation and boating come together in one exceptional property. This CBS 3-bedroom, 3-bath home sits directly on the runway and alongside a flow-through canal, offering the rare convenience of keeping your plane and boat close to home. Built for island living, the home features a durable metal roof and impact windows. Outside, a waterfront tiki invites you to unwind after a day on the water, while a 20,000-pound boat lift, commercial ice maker, and deep draft make this a compelling base for serious boaters. Follow the well-marked channel to the ocean, or head toward the Gulf via Kemp Channel. Explore offshore waters, cruise the backcountry, or spend an afternoon relaxing on the sandbars at Snipes or Marvin Key. Here, your next adventure can begin in the air or on the water. For the pilot who loves to fish, the fisherman who loves to fly, or anyone drawn to the freedom of both, this is more than a home - it's a distinctive way to experience the Florida Keys. Runway access and flow-through canal boating at one address make this a truly rare find! See the additional features on the Document tab. Airport information is available at: https://www.summerlandkeyairport.com/ Note: 2022 40' WorldCat is also for sale (separately).

86 S Airport Dr, Summerland
33 Pen, Islamorada
$2,195,000
3 Beds ⋅ 4 Baths ⋅ 621487 MLS
Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

33 Pen, Islamorada
1519 Johnson St, Key West
$2,190,000
5 Beds ⋅ 4 Baths ⋅ 621798 MLS
Discover island living at this spacious two-story, 5-bedroom, 4-bathroom retreat nestled in a quiet residential neighborhood right in the heart of Key West. Perfectly positioned this inviting property offers easy access to the beaches, tennis and pickleball courts, bocce courts, and the local dog park. Enjoy a leisurely bike ride to the vibrant energy of downtown Key West and Duval Street, then return home to your own private tropical escape. Inside, an open and welcoming floor plan features beautiful gray-blue tile flooring, a stylish kitchen, and generous living and dining areas designed for gathering with family and friends. With room to accommodate up to 14 people, the home offers exceptional flexibility for a large family, visiting guests, or those seeking a second home with income potential. The upper level provides two additional rooms, ideal for extra sleeping space, a home office, or a relaxing den. Step outside to a private backyard oasis featuring lush tropical landscaping, an expansive swimming pool, and a spacious deck perfect for outdoor dining, entertaining, and soaking up the Florida sunshine. A detached pool house adds another dimension of versatility, complete with a one-bedroom, one-bathroom studio and kitchenette--ideal for guests or additional living space. Offered fully furnished and with a history of vacation rental income, this property presents an exciting opportunity for investors seeking an income-producing asset or buyers looking to combine a personal island getaway with rental potential. Whether you envision a welcoming family retreat, a second home in paradise, or an investment in the Florida Keys lifestyle, 1519 Johnson Street offers space, flexibility, and a desirable central location to make it your own.

1519 Johnson St, Key West
216 Sonny Rd, Tavernier
$2,175,000
3 Beds ⋅ 2 Baths ⋅ 621826 MLS
First time on the market, this beautiful oceanside Key West/Bahama style home features 3 bedrooms/2 bathrooms, split floorplan for privacy, open living & entertaining area highlighted by soaring vaulted ceilings and abundant natural light. Spacious living area flows effortlessly onto an expansive lanai creating the perfect setting for outdoor dining, relaxing evenings, and enjoying the waterfront surroundings. The ground level features an impressive 2,376 square foot garage space (rarely found in the Keys) ideal for vehicles, boats, storage & workshop. Coveted corner lot with 215 feet of concrete dockage with davits. The canal provides direct ocean access to Tavernier Creek offering convenient & efficient passage to both the ocean and the bay, making this location especially desirable for anglers and cruisers alike. This is an opportunity to own a special waterfront home with exceptional dockage, oversized 10,000 square foot lot, tropical landscaping, and a paver driveway. This home is located near schools, shopping, restaurants, marinas (to fuel your boat). movie theater, and hospital.

216 Sonny Rd, Tavernier
581 12th St, Key Colony
$2,174,000
4 Beds ⋅ 2 Baths ⋅ 621230 MLS
Set along a canal in Key Colony Beach, this four-bedroom, two-bath home makes it easy to spend the morning on the boat and the afternoon by your own private pool. Inside, the open kitchen offers ample cabinetry, generous counter space, and bar seating that flows into the dining and living areas. The four-bedroom layout gives guests room to spread out, while the primary suite has its own bath and opens onto a covered deck. A dedicated laundry area adds everyday convenience. Out back, a spacious pool deck and covered entertaining area give you a choice of sun or shade. Rinse off in the outdoor shower after a day on the water, then settle in for dinner by the canal. Mature tropical landscaping frames the backyard, and substantial canal frontage with a seawall, dockage, and a boat lift makes it easy to keep your boat close at hand. With convenient boating access to both the Gulf and Atlantic, you can head out for fishing, diving, or snorkeling right from home. A metal roof, covered parking, and storage round out a property that's equally inviting as a full-time home or a place to get away to the Keys.

581 12th St, Key Colony
704 Grouper Ln, Key Largo
$2,160,000
3 Beds ⋅ 3 Baths ⋅ 619503 MLS
Wake up on the water in this turnkey, fully furnished coastal retreat in the heart of Key Largo. Complete with a modern, beach-chic design, this 3-bedroom, 3-bath home blends effortless luxury with true Florida Keys living. Outside, enjoy direct ocean access from your private dock with boat lift--just minutes to world-class fishing, diving and sandbars. After a day on the water, unwind in the resort-style pool with submerged bar stools, sun shelf, and turf yard perfect for lounging, grilling, and sunset cocktails. Walls of glass and multiple balconies frame sweeping ocean and canal views, filling the home with natural light. The open-concept main level features a stunning chef's kitchen with sleek cabinetry, quartz waterfall island, Bosch appliances, and gold accents, flowing into a relaxed living area designed for entertaining. The spacious primary suite is a true sanctuary with panoramic water views, private balcony, and spa-like bath boasting a freestanding soaking tub, oversized glass shower, and designer finishes. Guest rooms are thoughtfully furnished--including a bunk room--offering comfortable accommodations for family and friends. Offered fully furnished, down to the décor, this home is truly move-in ready--ideal as a primary residence, vacation escape, or high-end rental property. Experience the best of Keys waterfront living with style, comfort, and unbeatable ocean views

704 Grouper Ln, Key Largo
1419 Reynolds St, Key West
$2,150,000
2 Beds ⋅ 2 Baths ⋅ 621948 MLS
This residence in the coveted Casa Marina neighborhood presents a welcoming tropical retreat, where lush landscaping and coastal architecture set an immediate sense of privacy and ease. From the moment of entry, the home feels open and bright, with expansive windows that bring natural light across a well-balanced floor plan. The main living areas are designed for both comfort and flow, while ensuite bedrooms positioned on opposite sides of the open living space offer privacy and direct outdoor access. Outdoors, the private backyard stands out as a true highlight, featuring a large heated and chilled pool and a covered lanai designed for relaxed entertaining, complete with a wet bar and beverage cooler. The grounds are professionally landscaped and supported by irrigation, French drains, and automatic lighting enhancing both beauty and functionality. Additional conveniences include gated off-street parking on two sides, exterior storage areas, full-house central HVAC with an IR purifier, central vacuum system, wine and beverage coolers, ceiling fans, and integrated light dimming throughout. Located just minutes from the beach and within easy walking distance of nearby tourist areas, the property balances seclusion with accessibility. A property worth discovering with an open, charming feel and extra touches around every corner. Your island retreat awaits.

1419 Reynolds St, Key West
97501 Overseas Highway Unit 321, Key Largo
$2,150,000
4 Beds ⋅ 3 Baths ⋅ 621206 MLS
Waterfront living at Mariner's Club in Key Largo! One of only three residences in the entire community offering desirable views from both sides, this spacious 4BR/3BA residence enjoys open-water views on one side and marina views on the other--a rare distinction from most residences that face the parking area on one side. Offering 2,635 SF, the home features an expansive covered terrace ideal for indoor-outdoor living and entertaining. The generous floor plan includes a large living/dining area, stone flooring, abundant natural light, and a well-appointed kitchen with wood cabinetry, granite surfaces, stainless-steel appliances, double ovens, and breakfast area. The waterfront primary suite enjoys terrace access and beautiful views, while three additional bedrooms provide excellent space for family, guests, or office use. Located in a gated resort-style community with tropical grounds, pool amenities, marina surroundings, and easy access to the best of the Key Largo boating lifestyle. An exceptional combination of space, views, and location.

97501 Overseas Highway Unit 321, Key Largo
810 Carey Ln, Key West
$2,150,000
3 Beds ⋅ 2 Baths ⋅ 619599 MLS
Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. The home works beautifully as a two-primary suite layout, with the flexibility to convert one suite into a third bedroom or private study. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush landscaping. Located in the heart of Old Town, you're just moments from dining, shops, and the vibrant local scene, yet enjoy the peace and privacy of a hidden setting. Additional highlights include off-street parking--a rare and valuable convenience in this sought-after neighborhood. Whether you're seeking a full-time residence, vacation home, or investment property, this cottage captures the essence of Key West living. Possible Seller financing. .

810 Carey Ln, Key West
1724 Bahama Dr, Key West
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 618256 MLS
This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West. The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops, custom cabinetry, and stainless steel Thermador appliances. New tile flooring, updated lighting, and fully renovated bathrooms with clean modern finishes create a bright and comfortable interior throughout. The home also includes a new central air conditioning system and discreet security cameras that blend seamlessly into the design. A new roof adds peace of mind and makes this a true move in ready property. Outside, the home offers 56 feet of concrete seawall along a calm canal, providing excellent dockage potential and easy access for boating and paddleboarding. The outdoor space includes a bar and grilling area that is ideal for entertaining, along with a fully fenced yard finished with low maintenance turf for privacy and ease of care. The location is one of the home's strongest features. It is close to schools and the local high school and is within five minutes of grocery stores, restaurants, and beaches. Downtown Key West is approximately ten minutes away, offering quick access to Old Town, shopping, dining, and entertainment. This is a rare opportunity to own a fully renovated canal front home with flexible living space, boat ready frontage, and a central Key West location. One of the owners is a Licensed Florida Realtor.

1724 Bahama Dr, Key West
30468 Oleander Blvd, Big Pine
$2,150,000
3 Beds ⋅ 3 Baths ⋅ 617619 MLS
Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuring a two-bedroom, two-bath main house and a one-bedroom, one-bath guest cottage with views over Bogie Channel. Enjoy leisurely days entertaining under the large poolside tiki hut or on the covered platform at the end of the 463-foot pier—perfect for relaxing with family and friends while watching sunsets after a fun day on the water. The platform is equipped with a boat lift, floating jet ski dock, and an outdoor kitchen. The completely renovated, two-story CBS main home offers a spacious 1,950 sq. ft. living area with enough space to possibly add a third bedroom if needed. Large impact-resistant windows allow for views of peaceful sunrises and moonrises over the property and open water. The updated 536 sq. ft. frame-stucco guest cottage gives visitors their own comfortable retreat. Thoughtfully planned lighting enhances the 35,330 sq. ft. fenced property. Monroe County's small Palm Villa Park borders the southern edge, and the County owns the land directly across the street to the north, intended to remain undeveloped. Move-in ready and tastefully furnished, this tranquil slice of paradise is just minutes from local shops and restaurants, and only 30 miles from lively Key West. (Note: Living Area Sq. Ft. Source is the Property Record Card.)

30468 Oleander Blvd, Big Pine
1716 Laird St, Key West
$2,145,000
3 Beds ⋅ 2 Baths ⋅ 621461 MLS
Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Category 5 hurricane-rated construction, impact windows and doors, and Hardie board siding combine coastal style with storm protection. The home offers 3 bedrooms and 3 bathrooms, plus an office currently set up with bunk beds as a fourth sleeping space. Separate laundry room. The backyard is a gorgeous tropical retreat. A large heated pool and spa are surrounded by a gorgeous stone deck, lush landscaping and dramatic evening lighting. A huge poolside Tiki hut creates a spectacular setting for shaded dining, lounging and entertaining, while a putting green adds to the fun. Generous gathering areas and a completely fenced yard make this outdoor oasis perfect for sunny afternoons and unforgettable evenings beneath the palms. Inside, bright, open living and dining spaces flow into a beautiful kitchen with white cabinetry, stainless steel appliances, a blue tile backsplash and a generous island with seating. Balconies extend the living space outdoors. Beneath the home, a large covered area offers room to watch sports, relax and entertain, or serve as a carport. A permitted downstairs enclosure provides valuable storage and pool cabana. New construction, an elevated setting and an exceptional backyard come together in one remarkable property. Don't miss your opportunity to make this tropical escape your own!

1716 Laird St, Key West
58214 Overseas Hwy, Marathon
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 621687 MLS
LA PLAYA HOME, ***REDUCED, REDUCED*** YOUR SLICE OF PARADISE WITH ATLANTIC OCEAN FRONT AND OCEAN VIEWS FROM MASTER BEDROOM WITH BALCONY, KITCHEN, DINING, HUGE BALCONY OF KITCHEN AND DINING, HOME WITH UPDATES, TILE FLOORS, IMPACT WINDOWS AND DOORS, METAL ROOF, GRANITE COUNTER TOPS, UPDATED BATHROOMS, BEAUTIFUL 3 BED 2 BATH WITH MAIDS QTS, TWO CAR GARAGE, EXPANSIVE GROUNDS TO STORE RV'S AND BOATHS, PLENTY OF ROOM TO GROW, MINUTES FROM SHOPPING, DINING, GROCERY STORES, VIEW THIS OCEAN FRONT PARADISE IN GRASSY KEY.

58214 Overseas Hwy, Marathon
114 Spoonbill Rd, Tavernier
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 621120 MLS
Newly renovated 3-bedroom, 2-bath canal-front CBS home with direct bay access. The interior has been fully updated with tasteful coastal finishes, along with new impact windows and doors throughout. Enjoy 70 feet of concrete dockage with two boat lifts (24,000-lb and 15,000-lb) and a short idle to the bay, plus quick ocean access through Tavernier Creek. The wide lot offers ample space for trailer or RV parking. The ground level features covered parking and air-conditioned storage. Come experience why this neighborhood is so sought after, and see this quintessential Keys home for yourself.

114 Spoonbill Rd, Tavernier
499 Avenida Primiceria, Marathon
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 620036 MLS
Some locations make it easy to enjoy everything the Florida Keys have to offer, and 499 Avenida Primiceria just 7 houses in from Sombrero Beach is certainly one of them. Take a short stroll past just seven houses to Sombrero Beach, head out by boat with open water only minutes away, or spend the afternoon relaxing beside your private heated and chilled pool. This beautifully updated home has been designed for just that kind of easygoing lifestyle. Inside, the central living space welcomes you with soaring open-beam cathedral ceilings, a custom kitchen and an expansive floor plan that opens directly onto a screened porch overlooking the pool and dock. The primary suite occupies its own wing, separated from the guest bedrooms for added privacy. Recent improvements include plank tile flooring, impact-resistant windows and doors, updated bathrooms and a whole-house generator. Below, you'll find a garage, workshop, covered entertaining space and abundant storage. Outside, mature tropical landscaping and pea rock grounds create a private oasis with minimal upkeep. A 100' concrete seawall and 14,000 lb. boat lift complete the waterfront amenities. Come experience this distinctive Marathon retreat for yourself. Call today to arrange a private tour.

499 Avenida Primiceria, Marathon
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
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
662 Blackbeard Rd, Little Torch
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 619117 MLS
Pre-Construction Luxury Home | Jolly Roger Estates Introducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This CBS-built, fortress-like home is designed for durability, efficiency, and modern coastal living. The two-story floor plan offers 5 bedrooms, 4 bathrooms, and 2,886 square feet of living space, along with a spacious downstairs storage area--perfect for all your boating and outdoor gear. The property will feature a 10' x 23' swimming pool with an integrated jacuzzi, outdoor kitchen, and a TPO roof with a rooftop observation deck, ideal for taking in open water views, sunsets, and the surrounding Keys landscape. For boating enthusiasts, this home checks every box. The property will feature a 60' x 8' composite dock equipped with a 10,000-pound boat lift, set along deep, clear, flow-through canals with approximately 4 feet of draft-providing excellent accommodation for larger vessels and quick, easy ocean access with no bridges. Built with sustainability in mind, this Green Build Certified home includes features such as solar panels and a 1,000 gallon cistern, offering long-term value and reduced environmental impact. Conveniently located less than 5 minutes from restaurants, grocery stores, and shopping, and just 30 minutes from Key West, this property delivers the perfect balance of privacy, accessibility, and upscale waterfront living.

662 Blackbeard Rd, Little Torch
1609 United St, Key West
$2,099,000
6 Beds ⋅ 5 Baths ⋅ 622009 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
1125 Angela St, Key West
$2,099,000
5 Beds ⋅ 4 Baths ⋅ 621819 MLS
Rare old town 4 unit property. On the corner of Angela and Ashe streets. This property consists of a 2 bedroom unit and 3 1 bedroom units. All units have separate water and electric meters. Each unit has dedicated outdoor space. This is a perfect investment property. Buyers would need to verify use and refurbishment with the City. Currently two units have long term tenants. Two units are vacant. This is a great opportunity in a perfect location.

1125 Angela St, Key West
1501 Ocean Bay Dr Unit A 1, Key Largo
$2,099,000
3 Beds ⋅ 2 Baths ⋅ 620798 MLS
FRONT-ROW ATLANTIC OCEAN VIEWS! Discover a peaceful waterfront retreat in the intimate, 24-residence Key Largo Yacht Club community. This beautifully appointed 3-bedroom, 2-bath, three-story townhome offers breathtaking Atlantic Ocean views and spectacular sunrises from three private balconies, one on each level. Thoughtfully redesigned and remodeled in 2007, the residence features spacious, inviting living areas, coastal elegance, and the comfort of a move-in-ready home. Offered furnished, it's ready for you to immediately embrace the relaxed Florida Keys lifestyle. Boating enthusiasts will appreciate the rare deeded 50-foot boat slip with a four-post lift, conveniently located behind the garage, along with on-site dry boat storage and a community that permits jet skis. Whether enjoying your morning coffee overlooking the Atlantic, entertaining family and friends, or heading out for a day on the water, every day feels like a getaway. Privacy, tranquility, spectacular ocean views, and exceptional boating amenities come together in this extraordinary waterfront residence. Your Keys paradise awaits!

1501 Ocean Bay Dr Unit A 1, Key Largo
1040 81st Street Ocean St, Marathon
$2,099,000
3 Beds ⋅ 2 Baths ⋅ 620226 MLS
Enjoy sweeping ocean views from this beautifully designed Coastal Modern waterfront home in the heart of Marathon. Built with both style and durability in mind, this 3 Bedroom, 2 Bath CBS residence features concrete walls, floors, and roof, along with impact windows and doors for added peace of mind. Inside, oversized tile flooring and a bright open-concept layout create a clean, contemporary feel filled with natural light. The main living area flows comfortably to outdoor spaces, making the home ideal for relaxed Keys living and effortless entertaining. Two spacious guest bedrooms and a well-appointed guest bath provide inviting accommodations, while the private top-floor primary suite offers a peaceful retreat with access to the rooftop deck. An additional bonus space on the main level adds valuable flexibility and could serve as a possible 4th bedroom, office, pool cabana/dressing room or convenient guest overflow area. The rooftop deck is a true highlight, showcasing panoramic views of the turquoise Atlantic waters. Whether enjoying sunrise coffee, afternoon breezes, or evening cocktails under the stars, this elevated outdoor space captures the best of coastal living. After a day on the water, return to your concrete dock and unwind beside the canal-front pool with jets, or gather with guests on the expansive pavered patio overlooking the water. With multiple outdoor living areas, dockage, pool, and ocean views, the property is perfectly suited for boating, entertaining, and enjoying the laid-back island lifestyle. Conveniently located just minutes from restaurants, shopping, and the Marathon Airport, this property offers an exceptional blend of modern construction, coastal style, and Florida Keys waterfront living. With a proven rental history, this property also presents an outstanding investment opportunity for those seeking personal enjoyment and income potential in one of the Keys' most desirable destinations.

1040 81st Street Ocean St, Marathon
301 Little Miss Muffett Ln, Key Largo
$2,095,000
3 Beds ⋅ 2 Baths ⋅ 621228 MLS
Ocean's Edge Cottage -- a rare oceanfront opportunity in Key Largo, offering expansive open-water views, protected dockage and immediate direct access to the Atlantic. Situated on an oversized 60' x 90' peninsula-style corner lot, this unique property offers approximately 150 feet of shoreline with water on two sides, providing exceptional views from both inside and out. For the boating enthusiast, Ocean's Edge Cottage offers the best of both worlds: approximately 60 feet of concrete dockage in a protected area with a 17,000-lb boat lift, while still providing direct and immediate ocean access with no bridges. A natural coral breakwater provides additional protection while allowing water to flow freely along the north side, creating a clear swimming area where fish and marine life are frequent visitors. A private homeowners' oceanfront boat ramp provides additional convenience. The 3-bedroom, 2-bath home was designed to embrace its waterfront setting, with walls of glass capturing incredible water views from multiple sides of the main living and kitchen areas. The renovated kitchen features sparkling white cabinetry, granite countertops and stainless-steel appliances, complemented by an open-concept floor plan ideal for relaxed Keys living and entertaining. Additional features include impact-resistant windows and doors, an en-suite primary bedroom, interior laundry, outdoor shower and fenced yard. With open ocean in front, protected dockage for your boat and the Atlantic just moments away, Ocean's Edge Cottage delivers a combination increasingly difficult to find in Key Largo -- true oceanfront living without sacrificing protected boating.

301 Little Miss Muffett Ln, Key Largo
94 Sacarma Dr, Cudjoe
$2,060,000
5 Beds ⋅ 3 Baths ⋅ 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

94 Sacarma Dr, Cudjoe
5331 5th Ave, Stock Island
$2,050,000
6 Beds ⋅ 6 Baths ⋅ 620462 MLS
Attention Developers and Investors! This is a unique opportunity to acquire four parcels totaling 30,000 square feet of prime land just minutes from Key West. Ideally situated at Mile Marker 5, this property boasts a central location near some of the area's most sought-after resorts, dining establishments, and marinas. Whether you're looking to develop a new residential community, a commercial venture, or a combination of both, this land offers incredible potential. Its proximity to key attractions and amenities ensures a steady flow of visitors and residents, making it an ideal investment for future growth and profitability. 7 Electric Meters. 7 Water Meters. MU- Mixed Use Zoning. ROGO exempt for 6 or 7 units may be possible.

5331 5th Ave, Stock Island
5331 5th Ave, Stock Island
$2,050,000
6 Beds ⋅ 6 Baths ⋅ 620444 MLS
Attention Developers and Investors! This is a unique opportunity to acquire four parcels totaling 30,000 square feet of prime land just minutes from Key West. Ideally situated at Mile Marker 5, this property boasts a central location near some of the area's most sought-after resorts, dining establishments, and marinas. Whether you're looking to develop a new residential community, a commercial venture, or a combination of both, this land offers incredible potential. Its proximity to key attractions and amenities ensures a steady flow of visitors and residents, making it an ideal investment for future growth and profitability. 7 Electric Meters. 7 Water Meters. MU- Mixed Use Zoning. ROGO exempt for 6 or 7 units may be possible.

5331 5th Ave, Stock Island
3513 Sunrise Dr, Key West
$2,050,000
3 Beds ⋅ 3 Baths ⋅ 619190 MLS
Wake up in Key West and own your own piece of the island! Come enjoy a second-home outdoor living lifestyle on almost 1/4 acre private fenced-in landscaped tropical grounds corner lot with heated salt water pool, large porch and deck entertainment area and outdoor kitchen and BBQ area. The first floor is set to entertaining with French Saltillo (terracotta) floors throughout, a gourmet kitchen (with new appliances), dining room, open living room, bedroom and bath and a mother-in-law / guest bedroom/bath with private entrance. A dramatic flowing staircase leads to the second floor primary master ensuite bedroom with private balcony over-looking the large heated salt water swimming pool, private lush indigenous tropical exotic orchid gardens and gazebo. With private gated entrance, off-street parking, plenty of outside storage areas, and many on-site updates (automatic yard lights, timed irrigation system, Ring cameras throughout, Aquilink pool and fountain control, new roof and gutters, new A/C system, new water heater, new Kohler generator) to name a few. With close proximity to Old Town - Enjoy our local bars, restaurants, museums, art galleries and shops, beaches, and seaport activities (all within 10 minutes), then come home to a bit of peace and quiet. Comes furnished, this charming home available to purchase and close on at your earliest convenience

3513 Sunrise Dr, Key West
1 & 2 Aronovitz Ln, Key West
$2,033,000
2 Beds ⋅ 1 Baths ⋅ 618183 MLS
TWO OLD TOWN PROPERTIES. ONE RARE OPPORTUNITY. Tucked away on desirable Aronovitz Lane in the heart of Key West, this unique offering combines an existing 2-bedroom, 1-bath residence with an adjoining vacant parcel, creating exceptional possibilities for a buyer, investor, or builder. The vacant parcel offers the opportunity to rebuild its original two-unit footprint, while the existing home provides immediate use, income potential, or the foundation for a larger vision. Create a private Old Town compound, pursue new construction, maintain the existing residence while developing the adjoining parcel, or explore a long-term investment strategy. Additional features include off-street parking, Flood Zone X, above-flood construction, a metal roof, and an unbeatable Old Town location just moments from Key West dining, galleries, shopping, and waterfront attractions.

1 & 2 Aronovitz Ln, Key West

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