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Featured Properties

27358 Jamaica Ln, Ramrod
$899,000
3 Beds ⋅ 2 Baths ⋅ 620276 MLS
Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with water on 2 sides this property offers 150' of waterfront including a deep water basin, excellent dockage and easy access for boating, fishing, kayaking, or paddle boarding right from your backyard. Offering a flexible floor plan with separate living spaces on each level, this property is ideal as a full-time residence, vacation getaway, or investment opportunity. Upstairs, you'll be welcomed into a bright and inviting Great Room that serves as the heart of the home, with sliding doors leading to a screened lanai overlooking the canal where you can enjoy the island breezes. The functional kitchen offers plenty of space for everyday living and effortless entertaining, while the spacious primary bedroom and full bathroom provide a comfortable retreat. Downstairs offers two additional bedrooms, a full bath, laundry room, and a separate living area, providing plenty of space for guests or extended family. Storm ready with CBS construction, impact windows and doors and metal roof. Outdoor living takes center stage with an expansive yard and outdoor shed for convenient storage for all your boating and fishing gear. With quick ocean access from the canal, boaters can be on the water in no time, enjoying world-class fishing diving, Looe Key and endless adventures throughout the Florida Keys. Conveniently located on Ramrod Key, home to two popular outdoor restaurants with live entertainment, miniature golf and convenience store just a quick bike ride away, marina with boat ramp, and just a short drive from Key West, this waterfront retreat captures everything people love about life in the Florida Keys.

27358 Jamaica Ln, Ramrod

1116 Eaton St, Key West
$889,000
2 Beds ⋅ 1 Baths ⋅ 621609 MLS
Charming Old Town Key West Cottage with Private Pool & Rooftop Deck Welcome to 1116 Eaton Street, Key West, Florida 33040--a charming 2-bedroom, 1-bathroom single-family cottage in the heart of Old Town Key West. This beautifully maintained 749 sq. ft. home combines classic island character with comfortable living and exceptional outdoor spaces, including a private heated pool and rooftop deck. Inside, the efficient floor plan is filled with natural light and features inviting living spaces and two bedrooms positioned for privacy. The kitchen and living area flow naturally together, creating a comfortable setting for everyday living or entertaining. Step outside to enjoy your private pool and multiple outdoor living spaces. The heated pool provides a refreshing place to relax, while the rooftop deck offers an elevated setting for morning coffee, sunset drinks, dining, or entertaining. The location is exceptionally walkable, with convenient access to Duval Street, historic architecture, restaurants, galleries, shopping, nightlife, the Key West Seaport, and other Old Town destinations. Enjoy the privacy of a residential cottage while remaining close to the energy and attractions that make Key West so desirable. Whether you're searching for a full-time residence, second home, or investment property, this **Key West home with a private pool** offers a rare combination of location, outdoor living, and Old Town charm. Highlights: 2 bedrooms | 1 bathroom | 749 sq. ft. | Private heated pool | Rooftop deck | Multiple outdoor living spaces | Single-family home | Highly walkable Old Town location | Under $1 million. Experience the charm and convenience of Old Town Key West at 1116 Eaton Street.

1116 Eaton St, Key West

8 Cactus Dr, Big Coppitt
$875,000
3 Beds ⋅ 2 Baths ⋅ 621430 MLS
Up in the Air, Down to Earth: Your Escape on Big Coppitt! Built up on stilts, the way homes out here were meant to be built, this 3 bedroom, 2 bath home puts the living space where the light and breeze are, with a massive covered footprint below for parking, entertaining, and storage. Upstairs, the living, dining, and kitchen flow together the way a home should when real life actually happens in it. Stone counters, stainless appliances, an island, and windows everywhere that frame palm trees instead of your neighbor's fence. A favorite part might be the evenings though. Sit out on the deck and watch a storm roll across the Gulf, and once it clears, the skies out here are dark enough that you'll actually see the stars. The yard is fully fenced and secure, so if you've got dogs, they finally get room to run. Garden beds are already growing, there's a storage shed, a grill ready to go for whenever you feel like cooking outside, and an outdoor shower tucked in the corner for rinsing off after the beach or a day in the sun, with still enough open lawn for a pool or a fire-pit. You're twenty minutes from Key West whenever you want the restaurants, the noise, the whole scene. Then you come home to your retreat and never think twice about parking. Geiger Key Marina is very close too, a real locals spot for kayaking, paddle boarding, good food, and cold drinks, with water views that hold their own against anything in Key West. Three bedrooms, two baths, about 1,550 square feet of living space, elevated construction, covered parking and storage below, and a fully fenced oversized lot. Come see it. I think you'll feel it the second you walk up.

8 Cactus Dr, Big Coppitt

420 W Indies Dr, Ramrod
$850,000
3 Beds ⋅ 2 Baths ⋅ 617696 MLS
Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a standing-seam metal roof, impact doors and windows, and engineered wood flooring throughout. The open kitchen is both stylish and functional, featuring marble countertops, a large center island with electric and USB connections, a 5-burner propane stove, perfect for entertaining. All three bedrooms are comfortably sized, and both bathrooms have been beautifully remodeled with high-end finishes and bidet toilets. The elevated home provides a bright, airy interior and a comfortable retreat above the ground level. Downstairs, the outdoor living space is designed for relaxed Florida Keys living. A spacious covered lanai with bar and multiple seating areas creates an inviting place to gather, while the fully fenced 7,131 sq. ft. oversized corner lot offers privacy and room to enjoy the outdoors. Additional features include a gas fire pit, outdoor shower with hot water, lemon and lime trees, and convenient boat tie-downs. Boaters will appreciate the composite dock with 11,000-lb davits and quick access to deep water via the clear flow-through canal. This turnkey property is an excellent opportunity to enjoy the Lower Keys lifestyle with modern upgrades, exceptional boating, and outstanding outdoor amenities.

420 W Indies Dr, Ramrod

210 Golf Club Dr, Key West
$836,000
2 Beds ⋅ 3 Baths ⋅ 621063 MLS
WELCOME TO THE SANCTUARY-where privacy, tropical beauty, classic Key West style come together! Beyond the 2nd set of gates @ Key West Golf Club, this pristine courtyard spa home enjoys an enviable END LOCATION along a picturesque palm-lined lane. A RARE distinction: the ONLY one of 21 Sanctuary spa homes offering covered-carport access directly into the private courtyard/side yard! Classic KW charm begins at the wide front veranda, framed by vibrant tropical landscaping, polished stone & freshly painted exterior. Inside, natural light fills the inviting open floor plan w/taller ceilings & easy indoor/outdoor flow. The spacious island kitchen features granite countertops, abundant cabinetry/storage, all stainless-steel appliances, new dishwasher, mosaic tile backsplash & new 5-light Tiffany-style fixture delicately adorns the island. Extended granite surfaces offer generous prep space while the island opens beautifully to the great room. Cozy recessed lighting sets the ambiance, spacious enough to allow for beautiful dining setting. Double French doors off the living room reveal a private tropical courtyard--brick pavers, lush established gardens & covered outdoor living surround your own inground jacuzzi spa. Morning coffee, alfresco dining or an evening soak beneath the palms...this is quintessential Keys living! Upstairs are 2 generously sized bedrooms, each w/soaring vaulted ceilings & private en-suite bath. Primary bath offers expanded granite countertop, vessel-style sink, porcelain tub/shower glass doors & clever built-in towel storage. Guest bedroom is spacious w/a bath featuring upgraded lighting & tiled corner shower. Extras include on-demand hot water heater, storm shutters for most doors/windows, stack W/D, under-stair storage, termite protection plan. Enjoy KWGC's 24-hr Resident Services, 2 stunning pools (one w/tropical waterfalls), clubhouse/fitness center, lush Rees Jones-designed 18-hole golf course. A private Sanctuary retreat distinctly its own

210 Golf Club Dr, Key West

22968 Drake Ln, Cudjoe
$819,500
3 Beds ⋅ 2 Baths ⋅ 621169 MLS
Welcome to 22968 Drake Lane -- a charming canal-front home located on the desirable Cudjoe Key, one of the Lower Keys' wonderful communities. Set on a generous 7,500 SF lot with direct canal access and a private boat lift, this property is a true dream for anglers, divers, and boaters looking to get out on the water in minutes. with quick access to the backcountry flats as well as the open water beyond. Inside, the approximately 1000SF living area feels bright and spacious thanks to high ceilings throughout the main living areas. The updated kitchen, featuring granite countertops and stainless steel appliances, perfect for entertaining or everyday island living. Glass sliders lead from the living area out to a large covered porch, where you'll enjoy a peek-a-boo open bay view -- an ideal spot for morning coffee, evening cocktails, or simply soaking in the classic Florida Keys lifestyle.Downstairs, an oversized garage which holds 2 cars and possibly more offers abundant space for vehicles, boats, kayaks, fishing gear, and all the toys that come with life on the water, plus additional storage to keep everything organized. Located on Cudjoe Key in the heart of the Lower Keys, this home offers a peaceful, laid-back setting while remaining just minutes from the vibrant restaurants, nightlife, and culture of Key West. Enjoy easy access to some of the best fishing, diving, and snorkeling grounds in the world, right from your own backyard.Whether you're searching for a full-time residence, a weekend retreat, or a smart investment in one of the most desirable stretches of the Florida Keys, this canal-front gem checks every box. Boat lift, water access, and some updated finishes at this price point are increasingly rare in the Lower Keys market -- schedule your private showing today before this one is gone! A Bonus, this one has the potential for a partial seller financing to the right Buyer and low insurances.

22968 Drake Ln, Cudjoe

1160 Ave A, Big Pine
$799,000
4 Beds ⋅ 4 Baths ⋅ 621309 MLS
Set on a spacious 13,750 sq. ft. double lot, this 4 bedroom, 4 bath home offers 2,284 sq. ft. of living space surrounded by lush tropical landscaping and an exceptional collection of 16 varieties of fruit trees. Originally built in 1981 and extensively renovated following Hurricane Irma, the residence features Hardie Board siding and trim, impact windows, seamless gutters and a comfortable interior designed for everyday island living. Inside, soaring ceilings create a bright, open feel, with all 4 bedrooms located upstairs for added separation from the main living spaces. The kitchen features granite countertops, lighted cabinetry, a propane range and generous double pantry storage. From the living room, views extend across the front porch to the surrounding fruit trees, bringing the tropical setting into everyday living. The spacious primary suite includes a sitting area, walk-in closet with automatic lighting, and en-suite bath. The front porch is designed for enjoying the setting, with built-in seating and umbrellas creating a shaded place to relax among the tropical landscape. You can even pick fresh star fruit right from the porch. A rear porch with a hot tub provides additional outdoor living space, while automatic low-voltage landscape lighting illuminates the grounds after sunset. The property features 16 varieties of tropical fruit trees, including mango, avocado, guava, star fruit, banana, coconut, sapodilla and more. A 2-car garage adds excellent storage and functionality with remote-controlled barn-style doors, roll-down shutters, and a pulley system for elevated storage. Additional features include Hardie Board siding and trim, impact windows, seamless gutters, 30-amp service and electric on-demand hot water. With its expansive lot, abundant outdoor living areas and remarkable tropical landscape, this property offers a distinctive slice of Florida Keys living.

1160 Ave A, Big Pine

701 Spanish Main Dr Unit 171, Cudjoe
$799,000
2 Beds ⋅ 2 Baths ⋅ 621307 MLS
YOUR OCEAN FRONT FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully maintained 2-bedroom, 2-bath elevated home combines incredible ocean views, exceptional boating access, and resort-style living in one of the Lower Keys' most desirable waterfront communities. Step inside to soaring ceilings, abundant natural light, and expansive windows that bring the beautiful ocean views into the home. Covered outdoor spaces invite you to embrace the Keys lifestyle, from morning coffee overlooking the water to evening cocktails after a day on the boat. The primary suite features a king bed and ensuite bath, while the guest bedroom offers a queen bed and its own private covered porch. Boaters will love the 35' concrete seawall with heavy-duty dock posts, cleats, swim ladder, and two fish-cleaning tables. Below the home, covered parking, generous outdoor living space, and a 12'x12' concrete storage enclosure provide plenty of room for all your boating, fishing, and island gear. Venture Out offers an incredible resort lifestyle with a heated pool, hot tub, marina, fuel dock, boat ramps, pickleball, tennis, bocce, basketball, playground, recreation hall, pavilion, 24-hour gated security, and more. Nightly rentals are permitted, and the home generated approximately $100,000 in gross rental revenue in 2025, providing an attractive added benefit when you're not enjoying it yourself. Sold turnkey and ready to enjoy, this is your opportunity to own a waterfront retreat and experience the Florida Keys lifestyle from day one. Seller financing may also be considered with acceptable terms.

701 Spanish Main Dr Unit 171, Cudjoe

27 N Lake Dr, Summerland
$799,000
3 Beds ⋅ 1 Baths ⋅ 620897 MLS
Welcome to the Mango Cottage on Summerland Key! Tucked away on a quiet dead-end street, this 3 bedroom, 1 bath canal front CBS home combines the laid back Florida Keys lifestyle with excellent boating access and a few features you simply don't find everywhere. Surrounded by multiple mature fruit trees, including several mango trees! This property has a distinctly tropical feel from the moment you arrive. Inside, the home offers an open floor plan, a bright kitchen with a skylight, and a spacious Florida room featuring a cool Hemingway style bar, the perfect spot to mix a drink, entertain friends, or unwind after a day on the water. An good sized laundry and utility room provides plenty of additional storage and functionality. CBS construction and a post-Irma metal roof add to the home's appeal. Out back, the pavered yard creates a low maintenance outdoor living space with plenty of room to add a pool. A 60-foot concrete dock puts your boat right outside your door, with excellent access from Summerland Key and marine fuel and ice conveniently located just down the canal. The location also puts you close to Ace Hardware, fantastic local restaurants, and everyday conveniences while still enjoying the peace of a tucked away residential dead end street. Aviation enthusiasts will appreciate the neighborhood's unique private airstrip setting, offering the potential for a true fly in/fly out Keys lifestyle. With tropical fruit trees, great boating, a concrete dock, generous outdoor space, and plenty of classic Keys character, Mango Cottage is ready for its next chapter.

27 N Lake Dr, Summerland

22822 Buccaneer Ln, Cudjoe
$799,000
2 Beds ⋅ 2 Baths ⋅ 620174 MLS
SELLER ACCEPTING BACK-UP OFFERS: Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal. Access to both the Atlantic and Gulf is easy and achievable in minutes, making it an ideal base for fishing, boating, and enjoying the Keys lifestyle. One of the home's standout features is its exceptional privacy. With no neighbors across the canal and no neighbors on one side, you'll enjoy peaceful water views and a secluded atmosphere rarely found in canal-front properties. Outside, the property features a 10,000-pound boat lift and davits, providing ample accommodations for your vessels. Downstairs, you'll find enclosed storage for all your gear along with covered parking. Mature tropical landscaping surrounds the property, creating a lush island setting. An RV hookup adds even more flexibility for guests and additional recreational vehicles. Inside, the home offers a wonderful open-concept layout. The kitchen features an abundance of hardwood cabinetry and a center island, creating an inviting space for cooking and entertaining. Off the living room, a spacious screened in deck is accessed through a fully opening sliding glass door, seamlessly blending indoor and outdoor living. High ceilings and beautiful cypress pine accents throughout the home add warmth and character, perfectly complementing the relaxed coastal lifestyle. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this waterfront gem combines privacy, character, boating amenities, and the relaxed island lifestyle that makes Cudjoe Key so desirable.

22822 Buccaneer Ln, Cudjoe

29034 Rose Dr, Big Pine
$785,000
2 Beds ⋅ 1 Baths ⋅ 620040 MLS
Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is filled with natural light and designed for comfortable island living, boasting high exposed-beam ceilings, adding character and depth to the space. The spacious kitchen features solid wood cabinetry, while recent updates to the bathroom, bedrooms, and bedroom flooring give the home a fresh coastal feel. A large pocket sliding glass door disappears into the wall, creating seamless indoor-outdoor living and opening to an expansive covered back porch measuring approximately 36' x 12', perfect for entertaining, dining, or relaxing canal-side. New composite decking and front porch railings were completed in 2024, adding durability and style, and additional updates include a new HVAC system, new tankless water heater, new siding, and new impact windows throughout. The primary suite offers walk-in closets and direct porch access, while the laundry area is conveniently located on the back balcony. Offered with new furnishings both inside and out, this move-in-ready Keys getaway is ideal as a full-time residence, vacation home, or investment opportunity. Don't miss the opportunity to check out this Big Pine Key gem!

29034 Rose Dr, Big Pine

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