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Featured Properties

$1,225,000
3 Beds 3 Baths 621211 MLS
Welcome to 14 Spoonbill Way, an exceptional single-family residence nestled within the sought-after golf club community offering a relaxed, resort-style lifestyle in Key West. With 3 bedrooms, 2.5 baths, a spacious bonus room currently configured as a bunk room, and beautiful golf course and lake views, this home offers the ideal blend of comfort, versatility, and effortless entertaining. The main level is designed for gathering, with an open-concept floor plan that seamlessly connects the kitchen, dining area, and living room. Whether hosting friends for dinner or enjoying a quiet evening at home, the space feels bright, open, and inviting. The living area extends naturally outdoors to a generous back deck overlooking the golf course and lake, creating an idyllic setting for morning coffee, alfresco dining, or cocktails at sunset. Upstairs, the primary suite offers a peaceful private retreat with its own deck and a generously sized walk-in closet--an uncommon and highly desirable feature that sets this home apart from others in the community. Two additional bedrooms and a full bathroom complete the second floor. Life in the golf club community is about more than just the home. Residents enjoy access to an array of resort-style amenities, including two swimming pools, a fitness center, a beautiful butterfly garden, and more. 14 Spoonbill Way enjoys an especially convenient position within the community, located in close proximity to the larger resort pool and with nearby guest parking--an added advantage when entertaining. From its thoughtfully designed open living spaces and distinctive primary suite to its tranquil golf course and lake views and enviable access to resort amenities, 14 Spoonbill Way captures the essence of relaxed Key West living. A rare opportunity to enjoy a private residence with the amenities and atmosphere of a resort, all in Key West's desirable golf club community.

14 Spoonbill Way, Key West

$1,200,000
2 Beds 2 Baths 619901 MLS
Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to open water, and inviting outdoor spaces designed for relaxing after a day on the water. Spend mornings on the screened porch, enjoy afternoon breezes from the private balcony off the primary bedroom, and make the most of a waterfront setting that brings the best of island living together in one place. Inside, the home features an open floor plan with tile floors, high ceilings, a bright living and dining area, and a kitchen with a breakfast bar. The main bedroom includes a walk-in closet and direct balcony access, creating a private spot to enjoy the tropical surroundings. Outside, boaters and water lovers will appreciate the approximately 40-foot dock, dedicated skiff launch/ramp, canal frontage, and quick route to open water. The dock and waterfront setup provide a convenient place to keep a boat, launch a skiff, or head out for a day on the water with ease. The property also offers a garage and carport area, giving plenty of room for parking, storage, and Keys gear. Located in Sugarloaf Shores, this home offers peaceful island living with convenient access to dining, entertainment, and world-class recreation in nearby Key West.

17286 Jamaica Ln, Sugarloaf

$1,199,000
4 Beds 3 Baths 620193 MLS
Discover a rare combination of privacy, waterfront living, and spacious outdoor enjoyment on this nearly half-acre canal-front property in Big Pine Key. Boasting approximately 130 feet of waterfront, this unique location at the end of the canal offers minimal boat traffic, easy boating access to both the Atlantic Ocean and Gulf waters. Set behind lush tropical landscaping and a gated entrance, the fenced 19,762-square-foot lot creates a private retreat surrounded by mature palms, fruit trees, orchids, and vibrant native plantings. The heated swimming pool serves as the centerpiece of the outdoor living area, complemented by a large screened patio perfect for relaxing, entertaining, or enjoying the peaceful garden setting. Designed with boaters and outdoor enthusiasts in mind, the property offers ample room for multiple vessels, RV parking, and trailer storage, with convenient access through a separate gate. The ground-level residence spans approximately 2,166 square feet and features four bedrooms, two and one-half updated bathrooms, an upgraded kitchen, laundry room, impact-resistant windows and doors, a newer mini-split air conditioning system, and a ceramic tile roof installed in 2017. Additional highlights include abundant storage space, a dedicated workshop area, and extra refrigeration and freezer capacity for fishing gear and supplies. Offered furnished, this home is ready to be enjoyed from day one. Located just a short distance from Big Pine Community Park, residents can enjoy pickleball, tennis, basketball, walking paths, playgrounds, waterfront picnic areas, and community events. Whether you're seeking a full-time residence, vacation home, or private waterfront escape, this property offers the space, seclusion, and Keys lifestyle that are becoming increasingly difficult to find.

30985 Hibiscus Dr, Big Pine

$1,195,000
3 Beds 2 Baths 619184 MLS
Turnkey and move-in ready, this exceptional waterfront home is being offered fully furnished--including furniture, dishes, cookware, and linens--so you can start enjoying the Florida Keys lifestyle from day one. Situated on an oversized 18,000 sq. ft. double lot with 150' of canal frontage in a quiet, peaceful Big Pine Key boating community, this solid concrete 3BD/2BA home features a desirable split floorplan, tile floors, granite countertops, ample storage, attached garage, impact windows and doors, accordion shutters, and a metal roof. Boaters will love the easy access, including a 75' concrete dock with a 17,000 lb boat lift. The sellers have plans to extend the concrete seawall across the second lot, creating the potential for an additional 75' of dockage. Enjoy outstanding access via Bogie Channel with quick routes to both the Atlantic Ocean and Gulf waters, putting world-class fishing, diving, sandbars, and minutes to Bahia Honda State Park and beach. Outdoor amenities include screened and open porches, a tiki hut, outdoor shower, fenced yard, 50-amp RV service, and abundant parking for boats, trailers, and recreational equipment. The spacious double lot and tranquil setting create the perfect backdrop for relaxing island living while still being close to all the Lower Keys has to offer. A rare opportunity to own a fully furnished, move-in ready waterfront home with exceptional boating access and future dockage potential in the Lower Florida Keys. The unique community zoning allows for marine business and income potential from marine-related services.

29534 Geraldine St, Big Pine

$1,150,000
2 Beds 2 Baths 620012 MLS
Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the highest natural elevation on the island, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed during the Henry Flagler railroad era, the home has been thoughtfully updated while preserving the warmth and authenticity that make Key West architecture so iconic. Inside, rich Dade County pine walls, hardwood flooring, and tall ceilings create an inviting atmosphere filled with natural texture and timeless charm. Impact windows and curated high-end finishes blend seamlessly with the home's historic roots. The kitchen was designed with both style and function in mind, featuring dade county pine countertops and a collection of premium appliances including a Sub-Zero refrigerator and Big Chill gas range. Flexible living areas allow the home to function as either a spacious two-bedroom retreat or a three-bedroom layout depending on your needs. Outdoor living is equally special. A lush backyard filled with mature tropical landscaping and fruit trees creates a private island setting that feels worlds away from the bustle of town, with space to potentially add a pool in the future. The welcoming front porch serves as a timeless gathering space, perfectly suited for morning coffee, evening cocktails, and enjoying the laid-back rhythm of Old Town living. Just a short stroll from Truman Waterfront Park, Fort Zachary Taylor Beach, galleries, restaurants, and marinas, this property captures the essence of classic Old Town living -- historic, relaxed, and unmistakably Key West.

709 Chapman Ln, Key West

$1,150,000
2 Beds 2 Baths 619610 MLS
Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay homage to the home's rich heritage. Recent enhancements have elevated the home's functionality and aesthetic appeal including a new foundation, beautiful new flooring, tastefully updated bathrooms, and fresh paint inside and outside. The home features high ceilings with exposed beams and French doors that open to a private patio. This outdoor space is perfect for morning coffee or evening gatherings under the stars. The second-floor primary suite offers a private sanctuary, complete with a walk-in closet and an en-suite bathroom featuring a classic clawfoot tub. The downstairs bedroom is generously sized and includes a walk-in closet. The private patio, accessible through French doors, is ideal for alfresco dining and relaxation. The front porch offers a quiet spot to enjoy the tranquility of Elgin Lane, a quiet lane that ensures privacy and minimal traffic. A designated off-street parking space adds to the convenience of this property. A private walkway provides direct access to Eaton Street, placing local bakeries, shops, and the vibrant Seaport just steps away. Situated less than a block from the renowned Old Town Bakery and just two blocks from the lively Seaport, this home offers unparalleled access to Key West's finest dining, shopping, and entertainment venues. Whether you're seeking a serene personal retreat or a lucrative investment property, this residence offers an exceptional opportunity to own a piece of Key West's storied history.

1025 Elgin Ln, Key West

$1,139,000
3 Beds 2 Baths 620641 MLS
Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

1708 South Street, Key West

$1,099,000
3 Beds 2 Baths 621076 MLS
This waterfront home features impact windows and doors throughout, providing reliable security and peace of mind. Boating enthusiasts will appreciate the direct canal access with no bridges to open water, making it easy to head straight out for a day on the water. The canal-side setup includes a 30' long concrete dock, giving you a dedicated spot to tie up your boat right behind the house. Inside, the home boasts a light-filled 3-bedroom, 2-bathroom open layout designed for comfortable coastal living. The updated kitchen is a chef's delight, complete with granite countertops, stainless steel appliances, a Frigidaire gallery refrigerator, and a built-in wine rack. Additional interior highlights include a dedicated laundry room and a primary bathroom with a large soaking tub in the en-suite. Downstairs, you will find versatile utility and storage space perfect for keeping all your gear organized. Nestled in the desirable island neighborhood of Breezeswept Estates on Ramrod Key, this home offers an authentic Florida Keys lifestyle with direct access to crystal-clear waters, world-class diving, snorkeling, and premier fishing. Launch with ease from a public boat ramp less than two miles away, and spend your weekends exploring popular nearby sandbars. After a day on the water, take a quick walk or bike ride to several local restaurants. This location seamlessly combines quiet neighborhood charm with unbeatable access to the best marine adventures in the Keys.

27334 Guadaloupe Ln, Ramrod

$1,099,000
3 Beds 2 Baths 618854 MLS
Pride of ownership makes this house a home buyer's dream. This 3 bed, 2 bath, 1492sf home sits on an oversized fully fenced lot with beautiful landscaping, 14x32 heated, saltwater pool, large screened porch w/stairs to the pool & outdoor living space offering a private retreat for you to enjoy the laid-back Florida Keys lifestyle. Located in Breezeswept Beach Estate in Ramrod Key, this home is walking distance to restaurants, shopping and a short drive into famous Key West and all that it has to offer! Built in 2016 and beautifully maintained 2018 updates: porcelain tile floors, kitchen/bathroom cabinets, granite counters & stainless appliances. Large kitchen w/center island, dedicated dining area, bonus bar seating and laundry room with utility sink and washer/dryer tucked behind the kitchen. This unique floorplan has a private master suite with separate water closet, dual sinks, and walk-in closet. Two additional bedrooms on the opposite side of the house with a walk-in closet and lots of natural light. Large guest bathroom with jacuzzi tub and upgraded cabinets/countertops. Open concept living is ideal for entertaining in your large family room open to the kitchen and dining area and access to the screened porch and pool area. Custom blinds, plantation shutters, freshly painted exterior, parking for your cars, boats and water toys. 299sf enclosure offers plenty of storage. This home can be fully furnished for vacation rentals, or choose to furnish with your own style. Ramrod Key & the Florida Keys offer many activities such as snorkeling, scuba diving, fishing, & boating from your private dock. Minutes to the Atlantic Ocean and the Gulf and home to the most amazing blue waters and abundant sea life. Metal roof, impact windows/doors, Hardie-board siding and a 10,000lb boat lift makes this house a must see! Insurances approx $5,400 for wind/flood and homeowners combined.

27414 Guadaloupe Ln, Ramrod

$1,095,000
4 Beds 3 Baths 621049 MLS
Room to gather, room to grow - 211 Shore Avenue is a beautifully built 2018 retreat offering the space, security, and peace of mind today's Keys families are searching for. Set on a fully fenced 7,500sf lot behind an electric sliding driveway gate, 211 Shore Avenue offers the rare combination of privacy, space, and everyday livability that growing families search years for in the Keys, all just a short drive from Key West. Inside, 2,250sf of thoughtfully designed living space unfolds across two floors featuring four bedrooms and three full bathrooms, giving everyone in the family a place to call their own. The primary suite is a genuine retreat, complete with a private balcony and a spa-style en-suite bath featuring a walk-in shower and a deep soaking tub, the kind of quiet escape that makes the everyday feel a little more special. A dedicated second-floor laundry room keeps busy family life running smoothly, while a separate pantry off the kitchen adds the everyday storage that makes hosting, meal prep, and stocking up for island living effortless. Step outside, and this home truly shines as a gathering place, there's space for every kind of moment -- quiet morning coffee, sunset cocktails, or a full house of family and friends for a weekend cookout. And with a whole-home generator, impact windows/doors and low insurances, this is a home built for real Keys living, comfort and peace of mind, no matter what the season brings. Location adds even more to love. Big Coppitt Key offers the quieter, more residential side of the Lower Keys, while keeping Key West's restaurants, marinas, and famous sunsets a short distance away. Families will appreciate easy access to schools, nearby grocery stores, everyday shopping, and much more, all within easy reach. It's the best of both worlds: peaceful, low-key island life, with everything you need never far away. 211 Shore Avenue isn't just a house, it's a place for a family's next chapter to begin!

211 Shore Ave, Big Coppitt

$1,024,000
2 Beds 2 Baths 619409 MLS
Boater's dream waterfront on Ramrod Key with no-bridge ocean access, dual boat lifts, and open Atlantic access in minutes. Offered fully furnished and turnkey, this is Keys living at its best. Welcome to Breezeswept Dockside Retreat, designed for those who want to spend more time on the water. Situated on a 40' wide canal with approximately 3' control depth, you'll enjoy quick access to the Atlantic, Looe Key Reef, world-class fishing, diving, backcountry sandbars, and nearby Picnic Island. A fuel and dive shop are conveniently located at the north end of the canal. Launch from your backyard with 60' of composite dockage (2022), a 14,000-lb and 6,000-lb boat lift, making this property ideal for multiple vessels and serious boating enthusiasts. Inside, the open-concept living area flows onto a full-length covered verandah overlooking the canal. Outside, relax in the private saltwater pool, entertain on the spacious deck, and enjoy tropical landscaping after a day on the water. Property Highlights: • Turnkey, fully furnished • No-bridge ocean access • 60' composite dock (2022) • 14K & 6K boat lifts (2022) • Saltwater pool (2019) • Metal roof (2018) • A/C (2022) • Lower enclosure (2021) • 28-day rentals allowed • Flood Zone AE • Voluntary HOA • Low insurance: under ~$7K wind/homeowners + assumable flood policy (~$520) Rarely does a waterfront home combine immediate boating access, premium dockage, a private pool, and turnkey convenience in one exceptional Lower Keys property.

27416 Cayman Ln, Ramrod

$1,000,000
3 Beds 2 Baths 620253 MLS
Mermaid Landing: Investment Opportunity & Coastal Retreat Discover a one-of-a-kind property in the Florida Keys that offers unparalleled flexibility -- Mermaid Landing. This 3-bedroom, 2-bathroom home is perfect for savvy investors or those seeking a personal paradise, featuring rare access to a beach on the Gulf of Mexico. Located just 15 minutes from Key West, the property currently generates income with a long-term tenant while offering the ultimate coastal lifestyle. The 33,000 sqft lot is a treasure trove of potential. A partially fenced yard with a double gate provides ample parking for vehicles, boats, and RVs. This property is as versatile as it is attractive. The true gem? Direct access to a beach that lets you step straight from your artificial turf yard onto the Gulf shoreline, delivering breathtaking water views that most can only dream about. Newly renovated with a spacious primary bedroom and modern kitchen, Mermaid Landing seamlessly transitions between a profitable investment and a personal sanctuary. The existing tenant ensures immediate income potential, while the property's design offers endless possibilities for rental management or personal use. More than just real estate, this is your ticket to Florida Keys magic. Whether you're an investor seeking reliable returns or a buyer wanting a coastal retreat, Mermaid Landing delivers. With its prime location, access to a beach, and incredible versatility, this property is a rare find. Don't miss your chance to own something extraordinary. Schedule an exclusive viewing today and prepare to be captivated by the endless possibilities of Mermaid Landing.

813 2nd St, Big Coppitt

$999,000
3 Beds 2 Baths 620987 MLS
Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

506 Grinnell St, Key West

$999,000
4 Beds 3 Baths 620041 MLS
This newly built 2026 home on Stock Island delivers what buyers rarely find in the Florida Keys: true new construction, built to current code, with a fully legal guest suite and insurance costs designed to be as manageable as possible -- all priced under $1M. The main residence offers 3 bedrooms, 2 bathrooms, and over 1,500 square feet of thoughtfully designed living space elevated 18 feet above grade. Interiors feature waterproof and scratch-proof luxury vinyl plank flooring, quartz countertops, stainless steel appliances, and in-unit washer and dryer. HardiePlank siding, impact-rated doors and windows, and a metal roof complete a build package engineered for Keys living. Central air conditioning keeps the main home comfortable year-round. The elevated guest suite -- positioned at 9 feet with its own private entrance below the main home -- adds one bedroom, one bathroom, and approximately 500 square feet of additional living space, complete with quartz countertops, stainless steel appliances, in-unit laundry, and a mini-split system. Live in one, rent the other, or house extended family with total privacy. Similar properties are bringing in over $6500 per month in rent. The fully fenced, rock-covered lot provides covered parking under the home and additional off-street parking out front -- a genuine premium in the Keys. Stock Island puts you one bridge from Old Town Key West, with marinas, restaurants, and the energy of the Keys right at your door.

49g Miriam St, Stock Island

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