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29635 Saratoga Ave, Big Pine
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 619377 MLS
Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This beautifully built 3bedroom, 2bath CBS home offers the perfect blend of durability, comfort, and laid-back Keys living. Constructed with poured concrete floors and designed for peace of mind, the home features a tiled interior, a tiled roof, and convenient accordion shutters throughout. Step outside and embrace the tropical lifestyle, lush surroundings, charming paver walkways, and multiple spaces designed for relaxation and entertaining. Unwind in the screened porch as ocean breezes roll through, or soak your cares away in the hot tub beneath the stars. A cozy gazebo creates the perfect shaded retreat for afternoon cocktails or morning coffee. For boating enthusiasts, this property is a dream come true. Enjoy quick access to open water with your private seawall and boat lift, making every day a perfect day to be on the water. Additional storage provides room for all your gear, from fishing rods to paddleboards. Whether you're seeking a full-time residence, weekend escape, or investment opportunity, this home captures the essence of tropical living where every day feels like a vacation.

29635 Saratoga Ave, Big Pine
00000 Lagoon Dr, Summerland
$1,450,000
618940 MLS
Excellent opportunity to build your dream in paradise. This 6,140 sq foot lot with 70.65 ft. of water frontage has a beautiful open water and ocean view. This is the last lot available in this established subdivision Summerland Cove. Easy access to both the Atlantic Ocean and the Gulf of Mexico.

00000 Lagoon Dr, Summerland
1616 Atlantic Blvd Unit APT 18, Key West
$1,449,000
2 Beds ⋅ 3 Baths ⋅ 621689 MLS
Casa Caselles is an exclusive 19-residence gated community nestled along the Atlantic Ocean in Key West. This inviting two-bedroom, two and a half bath townhome offers the perfect blend of comfort, privacy, and island living. Enjoy the convenience of covered parking and a beautifully landscaped private courtyard, creating your own tropical retreat. Upstairs, the spacious living area offers an open, airy atmosphere with a seamless connection between indoor and outdoor spaces. A dedicated dining area flows naturally into the kitchen, providing an inviting setting for everyday living and entertaining. Surrounded by lush tropical landscaping, Casa Caselles offers residents a beautiful beachfront community pool and a peaceful setting just moments from everything Key West has to offer. Whether you're looking for a full-time residence or a private island escape, this townhome presents a wonderful opportunity to enjoy the Florida Keys lifestyle in one of Key West's intimate oceanfront communities. Schedule your private showing today and experience Casa Caselles for yourself!

1616 Atlantic Blvd Unit APT 18, Key West
1505 Johnson St, Key West
$1,449,000
3 Beds ⋅ 3 Baths ⋅ 617589 MLS
POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This property consists of a partially updated main home totaling 1233 sq ft with 2bd/2ba and a bonus room. A newly constructed elevated 256 sq ft guesthouse with a kitchenette and bathroom. Professional landscaping, pavers and low maintenance artificial grass lead to the brand new heated pool. Irrigation and landscape lighting installed. Main house needs some renovations throughout but has been partially updated and is perfectly livable. Must see!!

1505 Johnson St, Key West
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
646 William St, Key West
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 621406 MLS
644 William Street The property being sold is 644 William Street. The current property record/card reflects both 644 and 646 William Street, although the property being conveyed is 644 William Street. The structure at 644 William Street is a two-and-a-half-story home currently configured as a duplex and is in need of renovation. The first floor consists of two bedrooms and two bathrooms. The second floor contains two bedrooms and one bathroom. A stairwell provides access to the third floor, which is currently unfinished and is not completed or configured as living space. In its current condition, the property contains four bedrooms and three bathrooms of finished living area, with additional unfinished space on the third floor. The property is currently being used/configured as a duplex and will require renovation.

646 William St, Key West
1518 Sunrise Dr, Big Pine
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 620815 MLS
Discover your paradise in the heart of Big Pine Key! This beautifully maintained 3-bedroom 2-bath CBS, stilted home offers the perfect blend of Lower Keys Island charm and all the modern comforts. Step inside to find a bright, wide-open living space designed for relaxed Keys living and entertaining, with plenty of room for family & friends. Outside, your private backyard oasis awaits. Take a refreshing dip in the sparkling pool/hot tub, lounge in the tropical sun, or entertain your guests in the expansive outdoor living areas amidst the lush tropical landscaping. Whether you're enjoying morning coffee watching the sunrise over the Bay or unwinding with a cocktail after a day on the water, this home is designed for year-round enjoyment. Located in the tranquil Tropical Bay Estates community, you'll be literally minutes from world-class fishing, boating diving, nature trails within the natural beauty of the fabulous Lower Keys. Whether you're searching for a full-time residence, a vacation retreat or a profitable vacation investment rental, this exceptional property offers the laid-back island lifestyle you've been dreaming of. Come experience the best of the Florida Keys-where every day feels like a vacation.

1518 Sunrise Dr, Big Pine
7070 Overseas Hwy, Marathon
$1,400,000
4 Beds ⋅ 4 Baths ⋅ 620015 MLS
7070 Overseas Highway in the heart of Marathon presents an incredible mixed-use investment opportunity in a prime Overseas Highway location with outstanding visibility and endless potential. Formerly operating as a flower shop, Marathon florist, this versatile commercial property offers flexibility for a wide range of business ventures, income-producing opportunities, or redevelopment concepts. The property features approximately 4,168 finished square feet and is zoned for mixed use, making it appealing for a variety of uses! The high-traffic location provides exceptional exposure along one of the Florida Keys' busiest corridors. Looking to expand income potential? The second floor includes three residential rental units, creating immediate revenue opportunities: • One spacious 2-bedroom unit • Two 1-bedroom units Whether you are an investor seeking multiple income streams, an entrepreneur ready to launch a business in the Keys, or someone searching for a live/work opportunity, this property offers exceptional flexibility and long-term value. With mixed-use zoning, strong visibility, rental income potential, and a sought-after Marathon location, 7070 Overseas Highway is truly a rare opportunity for business investments, ventures, and future growth.

7070 Overseas Hwy, Marathon
140 S Bay Harbor Dr, Key Largo
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 619995 MLS
Your Dream Beach Home Awaits! 🌴Majestic Single Family Home for SaleLocation: Nestled in a quiet residential area, this stunning home sits on a spacious corner lot (50 x 100 ft) surrounded by beautiful gumbo limbo trees and vibrant tropical foliage.Key Features:Spacious Living: Approx. 1800 sq. ft. of living space 2 stories of comfort and style Ground Level: Welcoming entrance with a glass door leading to a small foyer 2 Large Bedrooms with ample natural light 1 Full New Bath featuring a high glass shower Each bedroom includes a new AC split One bedroom offers a glass door opening to a private back patio--perfect for relaxation! Upper Level: Expansive Living Room and Dining Room with an open layout Modern Kitchen with granite countertops Huge Master Bedroom with a private bath and an abundance of windows, creating a bright and inviting atmosphere High ceilings enhance the sense of space and light Separate entrance for added convenience Exterior Highlights:Unique lush setting with a wall surrounding the propertyMain gate entrance on Main StreetHuge Front Patio--ideal for entertaining or enjoying the outdoorsRoom for a pool to create your personal oasisAdditional Information:Fully furnished (included in the sale)Lease option available for a minimum of 6 months- The best to offer is the magnificent HOA park with private beach . Face time video available .Easy to show--vacant and ready for you!

140 S Bay Harbor Dr, Key Largo
233 Jolly Roger Dr, Key Largo
$1,399,000
2 Beds ⋅ 2 Baths ⋅ 622039 MLS
BRAND-NEW WATERFRONT CONSTRUCTION WITH IMMEDIATE BAY ACCESS! Discover exceptional waterfront living in the desirable Pirates Cove subdivision! Built by renowned Curry Dixon Construction, this beautifully crafted 2-bedroom, 2-bathroom concrete home offers quality construction, modern coastal living, and an unbeatable location for boating enthusiasts. Situated on a wide canal with immediate access to Florida Bay, this property boasts 50 feet of waterfront and a brand-new composite wood dock, providing the perfect setting to enjoy the Florida Keys lifestyle. Inside, the thoughtfully designed living space captures beautiful bay views directly from the living room, bringing the natural beauty of the Keys right into your home. Built with durability and future possibilities in mind, the home features solid concrete construction, including a concrete roof topped with a decorative metal roof for architectural appeal. This unique design also offers the potential for a future second-story addition, subject to applicable approvals and structural requirements. Additional features include a covered carport and private single-car garage, providing plenty of room for vehicles, storage, and boating essentials. RARE OPPORTUNITY TO EXPAND! The adjacent waterfront property at 33 Jolly Roger is also available for purchase, featuring a brand-new matching composite dock with a 25,000-pound boat lift and a ROGO exemption letter. Purchase both properties to enjoy an impressive 100 feet of waterfront with the opportunity to build an additional home, create an expansive waterfront estate, or potentially sell the additional building right separately, subject to applicable regulations and approvals. An exceptional opportunity to own brand-new construction with immediate bay access and incredible expansion potential in the Florida Keys!

233 Jolly Roger Dr, Key Largo
1507 19th St, Key West
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 621998 MLS
Beautifully Maintained Pool Home with Water Access in Key West! Discover the perfect blend of comfort and island living in this beautifully maintained 3-bedroom, 2.5-bath pool home, ideally located in Key West's desirable New Town neighborhood. This inviting residence features a bright, open floor plan filled with natural light, spacious living areas, and a wet bar perfect for entertaining. The primary suite offers a private ensuite bath and direct access to the pool, creating a seamless indoor-outdoor lifestyle. Step outside to your own tropical retreat! A charming flagstone pathway leads to a private floating dock on Sunrise Canal, ideal for launching kayaks, paddleboards, and small personal watercraft. Enjoy a short scenic journey through the waterways connecting to the Gulf and Atlantic waters, where you can explore Key West's beautiful backcountry. Relax poolside surrounded by lush tropical landscaping or unwind in the peaceful courtyard featuring a charming fountain. Additional highlights include a spacious covered carport with parking for multiple vehicles, ample outdoor storage, and a separate laundry room. Conveniently located near shopping, dining, beaches, and everything Key West has to offer. (This property has never been rented.) A wonderful opportunity to own a tropical pool home with recreational water access and enjoy the best of the Florida Keys lifestyle!

1507 19th St, Key West
94220 Overseas Hwy Unit 1D and 28' Boat Slip, Tavernier
$1,399,000
2 Beds ⋅ 3 Baths ⋅ 621711 MLS
BAYFRONT OPPORTUNITY | Sunset Hammock, Unit 1D Direct bayfront living with a 28-foot boat slip! Rarely available, Unit 1D at Sunset Hammock offers a special opportunity to enjoy the waterfront lifestyle in one of Key Largo's unique and tranquil gated communities. Featuring 2 bedrooms, 2.5 bathrooms, and over 1,523 square feet of living space, this residence offers open, expansive views overlooking the bay and marina. Enjoy beautiful sunsets, peaceful waterfront surroundings, and the convenience of having your boat just steps away with your own 28-foot boat slip. Sunset Hammock is an intimate waterfront community with only 40 residences, creating a private and peaceful atmosphere that is increasingly hard to find in the Florida Keys. Additional features include covered carport parking and ample downstairs storage for your boating equipment, kayaks, fishing gear, and all the essentials for enjoying life on the water. Amenities feature Pool, Beach If you have been searching for a direct bayfront property in a private, gated community with boating access, open water views, and a tranquil setting, this is an opportunity you won't want to miss! Experience the sunsets, embrace the boating lifestyle, and discover the special charm of Sunset Hammock in Key Largo.

94220 Overseas Hwy Unit 1D and 28' Boat Slip, Tavernier
27416 Tobago Ln, Ramrod
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 621530 MLS
**OPEN HOUSE | SUNDAY NOV. 1 FROM 11:00AM - 1:00PM** Welcome to 27416 Tobago Lane, where waterfront living and the Florida Keys lifestyle come together. This home offers open-water views and an abundance of indoor and outdoor spaces designed to make the most of island living. Boaters will appreciate the 10,000-lb boat lift and Jet Ski davit, while the fenced yard, lush tropical landscaping and multiple outdoor areas create your own private retreat. One of the home's most memorable features is the 3rd-story observation and sun deck. Take in the open-water views and ocean breeze during the day, then enjoy unobstructed stargazing and meteor showers at night. Tucked into the tropical landscaping you'll also discover a private meditation garden, orchid garden, mature fruit trees and a charming outdoor shower -- special spaces that give this property a personality all its own. Inside, high-end custom finishes and electric fireplaces add comfort and character, while an enclosed garage and oversized storage rooms provide the practical space that's so valuable in the Keys. Recent improvements include a 2025 A/C system along with a 2026 pool pump and saltwater system. Whether your perfect Keys day means heading out on the boat, relaxing by the pool, enjoying the gardens or ending the evening under the stars, 27416 Tobago Lane offers so many ways to enjoy life in the Florida Keys. Come see what makes this home special.

27416 Tobago Ln, Ramrod
1221 Ashby St, Key West
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 621518 MLS
Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

1221 Ashby St, Key West
27383 Saint Martin Ln, Ramrod
$1,399,000
4 Beds ⋅ 3 Baths ⋅ 621339 MLS
Offering twice the space and an exceptional waterfront lifestyle, this 4 bedroom, 3 bath Ramrod Key home offers 2,242 sq. ft. of living space on a 6,000 sq. ft. canal-front lot and includes the adjacent 6,000 sq. ft. lot, creating a combined 12,000 sq. ft. property with plenty of room to enjoy the Florida Keys lifestyle. Boaters will appreciate the 10,000 lb. boat lift, while brand-new Trex dock provides a fresh setting for days spent along the water. Designed with family and guests in mind, the main level features a welcoming living room with a fireplace and direct access to the rear deck overlooking the canal. A well-appointed kitchen is complemented by a conveniently located pantry and laundry area just off the kitchen, while a guest bedroom and full bath complete this level. Upstairs, the primary ensuite offers its own fireplace, creating a comfortable private retreat. Two additional guest bedrooms feature balcony access, while a bonus living room provides a versatile second gathering space with direct access to the upper rear deck. With waterfront decks extending from both living areas, the home makes it easy to transition from indoor living to the outdoors and enjoy the canal views. A spacious 2-car garage provides abundant room for vehicles, boating gear and recreational equipment, complemented by 658 sq. ft. of permitted downstairs storage. A metal roof installed in 2017 adds another notable feature to the home. Whether gathering across multiple living areas, relaxing on the waterfront decks or heading out by boat for a day on the water, this property offers the space and versatility to make the most of life in the Keys. With an adjacent lot included in the sale, generous storage and a layout made for spending time together, it is easy to see why the sellers describe it simply as ''the perfect family house.''

27383 Saint Martin Ln, Ramrod
1220 122nd St, Marathon
$1,399,000
4 Beds ⋅ 3 Baths ⋅ 620915 MLS
Discover Exceptional Waterfront Living on a Protected Lagoon in Marathon! Nestled in a quiet and highly desirable Marathon neighborhood, this beautifully updated 2,328 sq. ft. waterfront residence offers the ultimate Florida Keys lifestyle. Offered turnkey and fully furnished--with seller financing options available--this property also holds incredible potential as a weekly vacation rental. Inside, enjoy bright, open living areas featuring 4 bedrooms and 3 full bathrooms, plus a generous bonus room/den--perfect for a home office, media room, or potential 5th bedroom. The showstopping interior features a rare, one-of-a-kind indoor pool! In a truly unique layout, every bedroom features French doors that open directly onto the indoor pool deck, offering private access for family and guests alike. Step outside to 30 feet of dockage on a protected lagoon with quick access to the Ocean and Gulf. Don't miss this rare opportunity for luxury, tranquility, flexible purchasing terms, and income-generating potential!

1220 122nd St, Marathon
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
51 Drost Dr, Cudjoe
$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
1126 Grand St, Key Largo
$1,399,000
2 Beds ⋅ 2 Baths ⋅ 617647 MLS

1126 Grand St, Key Largo
209 Corsair Rd, Duck Key
$1,398,000
3 Beds ⋅ 2 Baths ⋅ 620387 MLS
Extensively remodeled 3-bedroom, 2-bath CBS pool home in Duck Key offering 2,076 sq. ft. of living space, smart-home technology, contemporary design, an ocean view, and exceptional indoor-outdoor living. The comprehensive remodel features sleek modern finishes and clean architectural lines throughout. The remodeled kitchen features an oversized quartz waterfall island, premium smart appliances, custom cabinetry, and a spacious walk-in pantry. High-contrast finishes, oversized interior doors, and designer lighting complement the home's sophisticated contemporary style. Both bathrooms have been completely redesigned with custom tilework, floating vanities, LED mirrors, premium fixtures, and large spa-inspired showers. Upstairs, the loft area and guest bedroom feature vaulted tongue-and-groove ceilings, adding warmth and architectural character to the modern interior. Outdoor living is highlighted by a new in-ground pool, expansive paver pool deck, and dramatic multi-story screened porch, creating generous space for entertaining, relaxing, and enjoying the Florida Keys climate. Elevated CBS construction provides substantial enclosed storage and flexible ground-level bonus space for storage, fitness equipment, hobbies, and other uses. Professionally prepared engineering plans for future expansion are also available. Located in Duck Key in the Middle Florida Keys, with convenient access to boating, fishing, waterfront dining, and nearby resort amenities. A distinctive opportunity for buyers searching for a remodeled Duck Key pool home with smart-home technology, contemporary finishes, ocean views, and extensive screened outdoor living.

209 Corsair Rd, Duck Key
34 Key Haven, Key Haven
$1,395,000
4 Beds ⋅ 2 Baths ⋅ 621790 MLS
4 BEDROOMS. 60 FT OF WATERFRONT. JUST $800/SF IN KEY HAVEN! Discover an exceptional opportunity to enjoy the boating lifestyle at 34 Key Haven Road. This 4 bedroom, 2 bathroom waterfront home offers 1,743 SF of living space, a wide canal, and quick access to both the Atlantic and Gulf. Set on a 6,000 SF lot, the home combines comfortable island living with the features boaters appreciate most. Inside, a bright, open layout centers around an updated kitchen with quartz countertops and stainless steel appliances, connecting naturally to the living and dining areas. Sliding glass doors from the main living space and primary bedroom open to a spacious covered patio overlooking the water. The flexible floor plan includes a fourth bedroom with a separate entrance, ideal for guests, a private office, or additional living space. Outside, 60 feet of concrete seawall provides generous dockage, making spontaneous days on the water part of everyday life. A metal roof, accordion shutters, CBS construction, and elevated setting add practical appeal and low insurances. Located just minutes from Key West, this home delivers the space, waterfront access, and relaxed lifestyle that make Key Haven so desirable. Whether you're searching for a full-time residence or your own boating retreat, 34 Key Haven Road deserves a closer look!

34 Key Haven, Key Haven
219 Sombrero Beach Rd Unit # 2, Marathon
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 620960 MLS
Welcome to 219-2 Sombrero Beach Road, a 4-bedroom, 3-bath waterfront retreat where mornings can begin with a walk to Sombrero Beach, afternoons can be spent on the boat, and evenings end around your private pool beneath the palms. The location is the difference. From here, one of Marathon's most loved beaches is just moments away, while 31 feet of private dockage puts the ocean within easy reach. Whether the day calls for fishing offshore, snorkeling, a sandbar run, or simply staying home by the pool, this property makes it remarkably easy to enjoy the reasons people come to the Florida Keys in the first place. Inside, 1,840 square feet offers four spacious bedrooms, three baths, an open living area, abundant natural light, and a relaxed coastal atmosphere designed for gathering. Outside, tropical landscaping surrounds a private pool and cabana-style entertaining area, creating a secluded space for long afternoons, dinners outside, and time with family and friends. And for buyers looking beyond the lifestyle, the numbers deserve attention. The property generated $115,000 in rental income in 2025, offering an established income history in one of Marathon's most recognizable vacation destinations. Current annual insurance costs are also notably attractive for a waterfront property, with approximately $4,262 for wind and $1,520 for flood insurance. That combination is difficult to replicate: Sombrero Beach within walking distance, your boat at the dock, a private pool in the backyard, four bedrooms for family and guests, and the ability to generate meaningful vacation-rental income when you're away. This isn't simply a place to own in the Florida Keys. It's a property designed to let you actually use them. Beach. Boat. Pool. Income. It's all here.

219 Sombrero Beach Rd Unit # 2, Marathon
1261 Ave A, Big Pine
$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
252 Pescayo Ave, Marathon
$1,395,000
613825 MLS
Open water views. 7876 sq ft lot with Building Right and Dock Permit at 252 Pescayo Ave just off Coco Plum Dr in Marathon, Fl 33050 89'+/-waterfrontage X 160' ave depth. Active Mangrove Fringe Clearing Permit.

252 Pescayo Ave, Marathon
1724 Rose St, Key West
$1,390,000
5 Beds ⋅ 4 Baths ⋅ 621031 MLS
Welcome to 1724 Rose Street, a spacious single-family home on a generous corner lot in a quiet Midtown neighborhood, close to Key West's beautiful beaches. The main level features an inviting open-concept kitchen, dining, and living area, along with three bedrooms and two baths. Freshly painted inside and out, the home is move-in ready while offering an opportunity to add your own personal touches and updates. The upstairs addition was done in 2016 offering two additional studio spaces. Both studios provide exceptional flexibility and could potentially be configured with a separate entrance, making them ideal for guests, extended family, a home office, or additional living accommodations. The large corner lot offers off-street parking for 2-3 vehicles, plus abundant on street parking. Out back, the spacious yard has plenty of room to create your own private oasis, with space for a large pool, outdoor lounging and entertaining areas, plus ample storage. With its flexible layout, generous lot, parking, and desirable Midtown location, this property offers numerous possibilities--from a comfortable home for a large family to monthly vacation rental use or employee housing. A rare opportunity to create a spacious Key West retreat with room to grow, customize, and enjoy the island lifestyle.

1724 Rose St, Key West
94825 Overseas Highway Unit 108, Key Largo
$1,390,000
3 Beds ⋅ 3 Baths ⋅ 615301 MLS

94825 Overseas Highway Unit 108, Key Largo
341 9th St, Key Colony
$1,380,000
3 Beds ⋅ 3 Baths ⋅ 621875 MLS
Waterfront Living in the Heart of Key Colony Beach! Discover the perfect blend of space, comfort, and the Florida Keys boating lifestyle in this beautifully updated 3-bedroom, 2.5-bath half duplex offering just over 2,000 square feet of living space. The spacious interior features updated flooring throughout, a beautifully updated kitchen with stainless steel appliances, and plenty of room for entertaining family and friends. A two-car garage provides ample space for vehicles, storage, and all your Keys lifestyle essentials. Boating enthusiasts will appreciate the 37.5 feet of dockage with low-maintenance Trex decking, along with easy ocean access and convenient bay access through Vaca Cut, making it effortless to enjoy a day on the water. The freshly painted exterior adds to the property's appeal. Located in the desirable island community of Key Colony Beach, you'll enjoy easy access to a wealth of amenities, including a Par 3 golf course, pickleball courts, parks, scenic biking and walking paths, local restaurants, and the beloved Sunset Park, where breathtaking sunsets are part of everyday life. Whether you're searching for a full-time residence or a Florida Keys getaway, this waterfront property offers the space, boating access, and island lifestyle you've been looking for. Come experience why life is better on the water in Key Colony Beach!

341 9th St, Key Colony
5607 College Rd Unit # B302, Key West
$1,375,000
2 Beds ⋅ 2 Baths ⋅ 621674 MLS
Experience waterfront living at its finest in this rare top-floor residence at Sunset Marina. Boasting breathtaking, unobstructed open-water views and spectacular year-round sunsets, this 2-bedroom, 2-bathroom condominium offers 1,171 square feet of thoughtfully designed living space. The spacious layout provides the perfect balance of comfort and functionality, featuring a generous living area, dedicated dining space, and well-appointed kitchen, along with two bedrooms ideal for accommodating family and guests. Boating enthusiasts will appreciate the full-service marina located just steps below, offering convenient access to everything needed for a day on the water. With direct access to the Gulf and a short boat ride to the Atlantic Ocean, this property is truly a boater's paradise. Sunset Marina is a gated, resort-style community offering a swimming pool, spa, and clubhouse. Additional conveniences include one covered parking space and private storage in the garage. Located just minutes from the heart of Key West and directly across from the island's only golf course, this exceptional residence combines waterfront tranquility with easy access to world-class dining, entertainment, and recreation. Whether you're searching for a full-time residence or an island getaway, this is a rare opportunity to enjoy the very best of the Key West lifestyle.

5607 College Rd Unit # B302, Key West
241 Sombrero Beach Rd Unit # 1, Marathon
$1,375,000
4 Beds ⋅ 3 Baths ⋅ 620983 MLS
Prime waterfront living on Sombrero Beach Road! This vibrant 4BD/3BA retreat (1,840 sq. ft.) delivers the total Florida Keys lifestyle. Walk to sandy Sombrero Beach, keep your boat at your private 30-ft dock with direct ocean access, and relax in your secluded tropical backyard with a private in-ground pool. An ideal personal getaway or income generator, boasting $45k+ rental income in 2025 and $60k+ in 2026. Beach, boat, pool, and proven performance--schedule your private tour today!

241 Sombrero Beach Rd Unit # 1, Marathon
9 Jade Dr, Big Coppitt
$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

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