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$2,750,000
4 Beds ⋅ 6 Baths ⋅ 620392 MLS
Resort-style living just got better! Turnkey waterfront living in prestigious Port Largo. This rare turnkey property offers a legally permitted duplex with ocean views, exceptional flexibility, and strong income potential in one of Key Largo's most desirable waterfront communities. The residence features two side-by-side townhomes, each with 2 bedrooms and 2.5 bathrooms, for a total of 4 bedrooms, 4 full baths, and 2 half baths. Every bedroom includes a private en-suite bath, providing comfort and privacy for owners and guests. Situated on 75 feet of waterfront, the property boasts a brand-new heated saltwater pool, concrete dock, and 20,000-pound Neptune boat lift. The wide, 80-foot deep-water canal offers quick ocean access, placing you on the first channel to the Atlantic with ocean views and easy access to world-class fishing, diving, and boating. Built entirely of concrete and fully renovated, this home combines durability with modern coastal style. Tastefully updated kitchen, flooring, baths, and more, this home was thoughtfully designed. Located on sought-after Marina Avenue, just steps from the private Port Largo homeowners' park, you'll enjoy beautiful sunrise views from the balconies and the privacy of a nature preserve directly across the street. The ground level includes a spacious storage room, covered parking, and a spacious tiki hut perfect for outdoor living and entertaining. Additional features include all impact windows and doors, an electric gated entrance on both sides, separate electric and water meters for each unit, and furnishings and décor included. Ideal as an investment property, family compound, or waterfront retreat, this unique Port Largo opportunity delivers the best of the Florida Keys lifestyle. Call today. Owner/Agent.

139 Marina Ave, Key Largo
$759,000
3 Beds ⋅ 2 Baths ⋅ 620391 MLS
3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size laundry room and on-demand hot water heater. Large master bedroom with en-suite bathroom, dual sink vanity and large walk-in closet. 2 guest bedrooms and full guest bathroom. Large covered porch off the main living/kitchen area, fenced on 3 sides. Newer downstairs storage room, room for boat/trailer; boat ramp is one street over and you are less than a mile from Sugarloaf Elementary and Middle school. Quick access to Key West and bases.

19543 Navajo St, Sugarloaf
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 620387 MLS
Extensively renovated CBS pool home in desirable Duck Key featuring luxury finishes, smart-home technology, and contemporary coastal design. This beautifully updated Florida Keys retreat offers an exceptional blend of modern style and island living, highlighted by a dramatic multi-story screened porch that captures natural light, tropical breezes, and seamless indoor-outdoor living. The designer kitchen serves as the heart of the home, showcasing an oversized quartz waterfall island, premium smart appliances, custom cabinetry, and a spacious walk-in pantry. Throughout the home you'll find soaring tongue-and-groove ceilings, oversized interior doors, designer lighting, and high-end finishes throughout. The luxurious bathrooms have been thoughtfully redesigned with custom tile work, floating vanities, LED mirrors, premium fixtures, and spa-inspired showers that create a true resort-style experience. Thoughtful upgrades and attention to detail are evident throughout every room. Outside, enjoy a beautiful new pool surrounded by an expansive paver deck, creating the perfect setting for entertaining or relaxing in the Florida Keys sunshine. The impressive screened outdoor living area offers a unique architectural feature, providing an inviting space to enjoy island breezes year-round. Elevated construction provides abundant enclosed storage, flexible bonus space, and room for hobbies, fitness equipment, or additional storage needs. Professionally prepared engineering plans for a future expansion are also available, offering additional flexibility and value for future owners. Located in the sought-after community of Duck Key, just minutes from world-class boating, fishing, waterfront dining, and resort amenities. A rare opportunity to own a fully renovated luxury home in one of the Florida Keys' most desirable island communities.

209 Corsair Rd, Duck Key
$2,299,000
2 Beds ⋅ 3 Baths ⋅ 620384 MLS
Enjoy endless ocean views from this charming Florida Keys waterfront retreat. Sitting on the edge of the Atlantic just one house in from open water, this stilted 2-bedroom, 2.5-bath CBS home also offers possible 3-bedroom flexibility and is a true boater's dream with 85 feet of waterfront frontage, concrete seawall, a 13,500 lb boat lift, deep-water dockage, and instant access to the Atlantic. The channel is slightly right as soon as you come out of the canal, placing you just minutes from Sombrero Light and some of the best boating, fishing, and diving the Keys have to offer. The home features a spacious, light-filled layout with a large living area, generous waterside windows, and sliding glass doors that frame the ocean views and open to east-facing covered porches on two levels. Inside, you'll find a comfortable eat-in kitchen with stainless steel appliances, abundant natural light, generous storage, walk-in closets, and impact windows and doors for added peace of mind. Outdoor living is the highlight, with a new waterfront pool and hot tub, expansive deck, large waterside porch, fenced yard, tropical landscaping, and multiple spaces to relax, dine, entertain, or simply take in the ocean breeze. Additional features include a garage, CBS construction, metal roof, travertine-paved driveway, inviting covered patio areas, and a large front yard offering flexibility for additional parking, boat/RV storage, or future use. The home is also available furnished, offering added convenience for those ready to start enjoying the Keys lifestyle right away. With open water just moments away, this Marathon property offers the perfect blend of boating, ocean views, poolside relaxation, and laid-back Keys living. This one is a must-see to truly appreciate.

1400 W 63rd St, Marathon
$879,000
2 Beds ⋅ 2 Baths ⋅ 620382 MLS
Welcome to the gem of the Florida Keys--beautiful Key Colony Beach! This impeccably maintained half duplex offers the perfect blend of island charm, comfort, and investment potential. Boaters will appreciate the approximate 30 feet of dockage with a 10,000 pound Boat Lift and quick, easy access to the open ocean for world-class fishing, diving, and boating adventures. Built for peace of mind, the home features impact-resistant windows and doors along with a durable metal roof. Inside, you'll find a bright and inviting open-concept floor plan designed for easy living and entertaining. The updated kitchen offers granite countertops, stainless steel appliances, and a convenient dining area. Spacious bedrooms feature double closets and generous storage, while the primary suite includes an ensuite bath with granite countertops and a large soaking tub/shower combination. Currently operating as a weekly vacation rental, this property is licensed for 7-night rentals. Whether you're searching for a personal Keys retreat, an income-producing investment, or both, this property checks all the boxes. Enjoy everything Key Colony Beach has to offer, from nearby waterfront dining and golf to beautiful beaches, parks, and endless water activities. Your Florida Keys escape--and investment opportunity--awaits!

271 3rd St, Key Colony
$849,000
1 Beds ⋅ 1 Baths ⋅ 620379 MLS
This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Tucked away on a quiet one-way street, this tropical retreat is just a short stroll to Cafe Sole, Little Pearl, Fausto's Food Palace, local bakeries, and charming boutiques. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West
$459,000
1 Beds ⋅ 1 Baths ⋅ 620376 MLS
Least expensive Condo at OP, this 1/1 has Impact windows and sliders with a nice Ocean view. Enjoy the direct Ocean Access Marina, Jr. Olympic pool and 14 person spa, Private Oceanfront Cafe & Lounge, Nice beach area with Tiki's , Lighted Pickle ball & Tennis courts. Boats have to be under 28ft and insured. Owners may rent their place or live here full time and Homestead their OP condo. OP is a gated community with 24/7 security and a fire sprinkler system in every room of every condo. This owner never rented their place so there are no rental numbers.

500 Burton Dr Unit 2304, Tavernier
$435,000
1 Beds ⋅ 1 Baths ⋅ 620374 MLS
Wake up to waterfront balcony views, spend your days on the water, and generate rental income--all from this beautifully renovated and fully furnished retreat at Coco Plum Terraces. This bright and airy condo features a designer kitchen with white shaker cabinetry, quartz countertops, stainless steel appliances, and a coastal-inspired glass tile backsplash. Recent upgrades include impact windows and impact sliding glass doors, a smart thermostat, Blink video doorbell, new window screens, a new A/C condenser (June 2026), and an outside connection for generator. Coco Plum Terraces offers an exceptional waterfront lifestyle with a heated waterfront pool, tiki hut, trailer parking, and optional boat slips accommodating vessels up to 40 feet. Boaters will appreciate deep-water dockage and direct ocean access with no bridges. Weekly rentals are permitted, making this an opportunity for both personal enjoyment and investment income. Just minutes from Coco Plum Beach, dining, shopping, and world-class fishing, Unit 111 delivers the perfect blend of comfort, convenience, and Florida Keys charm.

105 Ave D, Unit 111, Marathon
$609,000
3 Beds ⋅ 3 Baths ⋅ 620363 MLS
This move in ready townhome is located within the Islander Village HOA, a Local's Only Workforce Community. Seller offering to pay up to $15,000 of Buyers Closing Costs. Low insurances (approx. $4,200 a year) and low HOA dues ($165 a month) make this a fantastic opportunity for local buyers. FHA and VA financing accepted, and Buyer assistance programs available for qualified buyers. The home is elevated and above a garage for 2 cars. On the first floor are the kitchen, dining and living room as well as a 1/2 bath, 9' ceilings and covered front and back porches. Upstairs their is a large primary bedroom with 3 closets, two additional bedrooms and 2 full bathrooms. The home has very low insurances due to a metal roof and impact windows and doors. This locals community has a pool, dog park and an additional small park. If you live and work in Monroe County and want to join the Islander Village family please call for more information.

5030 5th Ave Unit 62, Stock Island
$780,000
620362 MLS
Build your dream home on this prime cleared oceanfront lot with open, no bridges access in the exclusive residential community of Key Largo Ocean Resort (KLOR), at MM 94.8. Spanning 22 acres, this 24 hr. guard-gated community reflects the uniqueness of coastal design homes and ocean living, framed by swaying palms and sea breezes. KLOR boasts an array of resort amenities including a full-service marina, boat ramp, clubhouse, swimming pool, fitness center, tennis, basketball and pickleball courts, children's playground, an iconic fishing pier, community events and so much more! Boat slips are not deeded. Property is ROGO exempt; easy to build. Seize the opportunity to build your own retreat in a highly desirable Upper Keys community. Friendly rental restrictions, minimum of 30 days.

94825 Overseas Highway Unit 123, Key Largo
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 620361 MLS
Waterfront coastal retreat in a quiet neighborhood, just 3 houses from open water! This beautifully renovated 3-bedroom, 2-bath stilt home offers coastal comfort with modern updates and relaxed waterfront living. Enjoy breathtaking sunsets from the screened-in balcony, or head down to the 70 ft dock with a 12,000 lb boat lift, perfect for boating enthusiasts. The fenced-in yard features lush fruit trees and outdoor space to unwind, plus room for an RV with 30 amp service. A spacious downstairs provides plenty of storage, making this home as functional as it is inviting. A rare opportunity to own a move-in-ready waterfront home in a peaceful setting!

29162 Bougainvillea Ln, Big Pine
$1,325,000
2 Beds ⋅ 2 Baths ⋅ 620360 MLS
Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bedroom, 1-bath residences, each finished with a refined European style kitchen. Clean lines, quality cabinetry, and thoughtful detailing give both sides a fresh, elevated feel while preserving the easygoing island character that makes Old Town so sought after. Each unit lives comfortably and independently, making this an ideal setup for an owner-occupant looking to offset costs, an investor seeking dual income streams, or a buyer wanting a flexible space for family and guests. Private yard space adds room to garden, relax, or entertain under the palms, a true rarity at this address.

1126 Grinnell St, Key West
$2,499,000
6 Beds ⋅ 4 Baths ⋅ 620359 MLS
Fantastic 6 Bedroom, 4 Bath 3,248 sq. ft. waterfront pool home in Key Colony Beach, an upscale coastal community of waterfront homes that allows weekly rentals and offers a plethora of amenities including gorgeous beaches, a beach club, golf, tennis, pickleball, restaurants, parks, shopping and more! World-class fishing and diving are just minutes from your 75' concrete dock on a 100' wide crystal clear canal offering quick ocean access. After a day on the water relax by your waterfront pool or take a bike ride to one of the great restaurants the island has to offer. The 2-story home is perfect for large families and guests with living areas on both floors and 2 Primary Suites. The home has been beautifully updated including new impact doors and windows and metal roof installed in 2023. The tropically landscaped yard offers lots of curb appeal and privacy. This home is zoned for duplex and with a few modifications can be turned into one. Please ask your agent for more details. Can be sold Turn Key!

581 10th St, Key Colony
$239,000
620358 MLS
An exceptional opportunity to build your custom Florida Keys retreat in the highly sought-after Key Largo Ocean Resort. This buildable homesite is ROGO exempt, allowing you to move forward with construction without the uncertainty of waiting for building rights--an increasingly rare and valuable advantage in the Florida Keys. Located within one of Key Largo's premier gated communities, this property offers the perfect setting for a full-time residence, vacation home, or investment property. Enjoy resort-style amenities including a beautiful clubhouse, heated swimming pool, marina with direct ocean access, private boat ramp, tennis and pickleball courts, basketball court, playground, and 24-hour gated security. Ideally situated just an hour from Miami, Key Largo Ocean Resort provides the perfect balance of convenience and island living. Spend your days boating, fishing, diving, or simply relaxing while enjoying everything the Florida Keys lifestyle has to offer. Whether you're ready to build now or planning for the future, opportunities to own a ROGO-exempt homesite in this desirable waterfront community are becoming increasingly limited. Don't miss your chance to create the custom home you've always envisioned in one of Key Largo's most sought-after neighborhoods.

94825 Overseas Highway Unit 1, Key Largo
$675,000
3 Beds ⋅ 2 Baths ⋅ 620357 MLS
Completely remodeled home with designer features. Looking for a modern up dated home. This home is for you. New roof, new kitchen, updated bathrooms, Impact windows and door. custom fencing and land scapng. Privacy fencing surrounding this home makes this home a private Oasis, Walking distance to the Sailing Club, Multiple Sunset Celebration point an fine restaurants. biking distance to Key Largo Park and Jacobs Aquatic center, professional Pickle ball courts, and the YMCA t the park.

123 Ocean Bay Dr, Key Largo
$879,000
3 Beds ⋅ 2 Baths ⋅ 620345 MLS
Beautiful ground level three-bedroom home with impact windows and doors and metal roof for your security. Fully furnished with artwork and kitchenware for your convenience. Window treatments and an oversized kitchen counter for your entertaining pleasure. Open porch in the back to enjoy the quiet outdoors. Roomy bedrooms for you and your family. Beautiful beach area in the neighborhood and County boat ramp and park close by, just a few streets away. Move right into this great home.

106 S Bay Harbor Dr, Key Largo
$625,000
2 Beds ⋅ 2 Baths ⋅ 620312 MLS
One owner since new, this Key West Golf Club townhome has been maintained with a new roof, new A/C, and an updated kitchen and baths -- the major systems and finishes are already done. Tile runs throughout the first floor, which opens across the kitchen, dining, and living space, plus a half bath for guests. Upstairs holds two bedrooms and a full bath finished with durable, eco-friendly cork flooring -- a resilient, long-lasting surface prized for comfort underfoot and sustainability -- along with a permitted enclosure of the front balcony that adds livable space most units in the complex don't have, plus an in-unit washer/dryer and dedicated storage. Outdoor living wraps the home front to back: a covered front porch, two screened back porches, and a fenced yard built for grilling and entertaining. The community pool, gym, and Zen garden are steps away. The location is what sets this community apart. Key West Golf Club is the island's only gated golf-course community -- a Rees Jones-designed 18-hole course, on-site bar and grill, two pools, a fitness center, and 24-hour gated security. Old Town, the beaches, and the marinas are a quick car or bike ride away. HOA dues are reasonable and cover cable and common-area maintenance. Zoning allows 30-day minimum rentals, so the unit works for seasonal income, long-term tenancy, or part-time ownership. The numbers back it up: at 871 verified square feet, this is the largest 2-bedroom, 1.5-bath townhome currently listed in the community -- and at $718 per square foot, the lowest-priced per foot in its category. Owner financing may be considered for qualified buyers, adding flexibility rarely found in this market. One careful owner, move-in ready, priced to move, in a location that doesn't come around often. Schedule your private showing today.

1 Spoonbill Way, Key West
$2,800,000
2 Beds ⋅ 2 Baths ⋅ 620355 MLS
High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

1009 Whitehead St, Key West
$699,000
2 Beds ⋅ 1 Baths ⋅ 620354 MLS
Welcome to 629 Powell Drive in Little Torch Key, the lowest-priced fully stilted CBS home currently available in the Lower Florida Keys. This elevated 2-bedroom, 1-bath canal-front home offers the ideal combination of affordability, boating access, and island living. Built for peace of mind, the home features a 2018 metal roof, accordion shutters on the doors, and panel shutters for the windows. Relax on the spacious east-facing porch, perfectly positioned to capture the prevailing trade winds while enjoying peekaboo open water views and cooler afternoon temperatures. Situated on a generous 7,400-square-foot lot, the property offers a huge paver driveway with ample room for multiple boats, trailers, RVs, and guests. The backyard provides plenty of space for a resort-style pool, creating the ultimate Keys retreat. Boaters will appreciate the deep, clean canal, concrete dock, and quick ocean access through Pine Channel, offering outstanding fishing, diving, and snorkeling opportunities. Downstairs, a massive enclosed storage area provides plenty of room for all your gear and water toys. Located in a desirable waterfront neighborhood with a community boat ramp and within walking distance of one of the Lower Keys' most popular waterfront tiki bars, this property delivers everything buyers love about the Florida Keys lifestyle at an exceptional value.

629 Powell Ave, Little Torch
$1,099,000
3 Beds ⋅ 3 Baths ⋅ 620351 MLS
Welcome to this beautifully updated 3-bedroom, 2.5-bath waterfront home situated on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Thoughtfully renovated throughout, this spacious two-story home offers bright, comfortable living with plenty of room for family and guests. Inside, you'll find a large living room filled with natural light, a versatile office/den, and an updated kitchen and dining area designed for everyday living and entertaining. Boaters will appreciate the canal access to Pine Channel, providing quick access to both the Atlantic Ocean and Gulf waters. The screened porch overlooking the canal offers a comfortable spot to relax, dine outdoors, or enjoy the peaceful waterfront setting. Outside, the expansive double lot provides plenty of room for parking, pets, and outdoor activities. The open space beneath the home offers endless possibilities for storage, a workshop, recreational space, or an outdoor living area. There's also ample room to add a pool and create your own private backyard retreat. Located in a desirable, family-friendly neighborhood, this move-in-ready property combines generous indoor and outdoor space, waterfront access, and the relaxed lifestyle that makes the Florida Keys so special.

1615 Fern Ave, Big Pine
$259,000
2 Beds ⋅ 1 Baths ⋅ 620349 MLS
Prime redevelopment opportunity just minutes from Key West! This 1959 single-wide mobile home sits on a desirable lot and is ready for its next chapter. The property is vacant and offered as-is, with no repairs or improvements to be made by the seller. There are no HOA or association fees, adding flexibility for future use or redevelopment. Due to the age of the structure, this is a cash-only purchase. Proof of funds is required prior to scheduling a showing.

60 Ed Swift Rd, Big Coppitt
$772,000
2 Beds ⋅ 2 Baths ⋅ 620348 MLS
Million-dollar sunsets. Turnkey investment potential. Unmatched Keys lifestyle. This beautifully remodeled fifth-floor Moon Bay condominium includes breathtaking Florida Bay views and expanded living space created by enclosing and incorporating the original balcony into the interior of the home. Sold fully furnished and turnkey, this exceptional property is ready from day one as your personal Keys retreat, income-producing rental home, or both. Weekly rentals are permitted, making this a great condominium for owners who enjoy the Keys during lobster season, holidays, and long weekends while generating rental income the rest of the year. Features include covered parking, abundant indoor and outdoor storage, custom cabinetry, and an optional boat slip with lift available directly in front of the unit. Moon Bay includes a waterfront pool, marina, tennis/pickleball courts, clubhouse, private beach, walking and biking trails, paddleboards, kayaks, gated entry, and resort-style amenities. Located near Adam's Cut for quick ocean access to world-class diving, fishing, and boating. Roll out of bed and onto a dive boat by walking next door to Amoray Dive Center. A short walk to the World Famous Caribbean Club, where the movie Key Largo was filmed, or to multiple waterfront sunset bar/restaurants just minutes away. Dazzle at the spectacular nightly sunsets as well as the annual Blackwater Sound Fourth of July fireworks from the comfort of your living room. Just steps away from Rowell's Waterfront Park with concerts, swimming, a dog park, and community events throughout the year. Only 57 minutes from Miami International Airport, this is an ideal Keys retreat, income-producing rental or both--easy to enjoy, easy to rent, and impossible to forget.

104350 Overseas Highway Unit A509, Key Largo
$549,000
2 Beds ⋅ 2 Baths ⋅ 620346 MLS
Canal-front Paradise Awaits! Incredible view from your back deck! Unit 424 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall. * Community Boat Ramp and boat washdown station. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This home has been very well cared for and updated and is ready for you to move in and enjoy. * Gated Community: Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! * Excellent rental income potential!!

701 Spanish Main Dr Unit 424, Cudjoe
$365,000
620344 MLS
Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living. Located within the gated waterfront community of Venture Out, owners enjoy access to outstanding amenities including a marina, boat ramp, fuel dock, heated saltwater pool, hot tub, pickleball and tennis courts, community activities, and more. With boating, fishing, diving, and breathtaking Keys sunsets just moments away, this is your opportunity to embrace the Florida Keys lifestyle you've been dreaming about. Come see why so many choose to call Venture Out home.

701 Spanish Main Dr Unit LOT 557, Cudjoe
$3,800,000
3 Beds ⋅ 3 Baths ⋅ 620343 MLS
First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

619 Ashe St, Key West
$1,850,000
2 Baths ⋅ 620342 MLS
701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations.

701 Simonton St, Key West
$999,000
2 Beds ⋅ 2 Baths ⋅ 620338 MLS
Completely renovated and move-in ready, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of coastal charm and boating convenience. The interior showcases quality upgrades throughout, including tile flooring, warm wood accents, impact windows and doors, and a thoughtfully designed kitchen featuring a propane stove for the culinary enthusiast. Natural light fills the open living spaces, creating an inviting atmosphere ideal for relaxing or entertaining. For boaters, the location is hard to beat. Enjoy quick and easy access to both the Atlantic Ocean and Gulf waters through nearby Vaca Cut, making it simple to spend your days fishing, diving, or exploring the Florida Keys by boat. Whether you're looking for a full-time residence, vacation getaway, or investment property, this updated home delivers the Keys lifestyle you've been dreaming of. Property is in the heart of Marathon so close to amazing restaurants, Marathon Airport, Million Air, grocery stores, Sombrero Beach and more! Seller has purchased new trex decking material for a new front porch area along with on the dock ready for new buyer to have installed, engineered plans and drawings already completed!

11490 2nd Ave, Marathon
$1,799,000
2 Beds ⋅ 2 Baths ⋅ 620337 MLS
Experience the Florida Keys lifestyle on a double lot in Marathon's sought-after Little Venice. This 2 bed/2 bath waterfront retreat boasts open-water views, 100' of concrete dockage with a 20,000 lb boat lift, and a resort-style outdoor living area built for entertaining. The backyard features a pool(heated or chilled), hot tub, poolside cabana with sink and refrigerator, mature tropical landscaping, and expansive decks for soaking up sunsets or unwinding after a day on the water. Practical boating amenities include power, water, lighting, and a fish-cleaning station; RV hookups and ample parking accommodate guests and all your toys. Inside, cathedral ceilings create a bright, airy living space while every bedroom enjoys its own private bath for comfort and privacy. Notable updates and systems: newer metal roof, tankless water heater, large laundry/utility room, and abundant storage. Located in a weekly-rental zone, the property offers strong income potential as a primary home, vacation getaway, or investment. From open-water vistas to thoughtful outdoor spaces, this home captures everything the Keys have to offer.

11563 4th Ave, Marathon
$685,000
3 Beds ⋅ 2 Baths ⋅ 620336 MLS
Affordable Florida Keys Living with Weekly Rental Potential in the Heart of Marathon Whether you're searching for a full-time residence, a vacation retreat, or an income-producing investment property, this charming 3-bedroom, 2-bath Conch cottage offers exceptional value in today's market. This property blends classic Keys character with modern upgrades and desirable rental flexibility. Newly renovated the home is move-in ready and designed for easy island living. Interior features include quartz countertops, stainless steel appliances, impact-resistant windows, and energy-efficient mini-split A/C systems that help keep utility costs low. The low-maintenance lot provides ample parking and storage, making it ideal as a primary residence, second home, or vacation rental. Situated in a weekly rental area, this property offers excellent income potential while allowing owners to enjoy their own slice of paradise. Conveniently located just minutes from world-class boating, fishing, waterfront dining, shopping, and all the attractions that make the Florida Keys such a coveted destination, this Little Venice gem combines affordability, convenience, and investment opportunity. Don't miss this rare opportunity to own an affordable piece of the Florida Keys with the flexibility to enjoy it, rent it, or both. Schedule your private showing today!

11554 5th Ave, Marathon
$1,295,000
2 Beds ⋅ 1 Baths ⋅ 620334 MLS
Welcome home! Charming Old Town Key West Cottage with Off-Street Parking. Situated on a desirable corner lot in Old Town, this 2-bedroom, 1-bath conch cottage offers the quintessential Key West lifestyle. Inside, natural light highlights the home's historic Dade County pine walls and original wood floors, blending timeless character with modern comfort. The updated kitchen and dining area create an inviting space for entertaining, flowing seamlessly into the living room and extending to a private outdoor retreat. Located in the desirable X flood zone, this property combines historic charm, modern updates, and an exceptional location--everything you need to experience the best of Key West living.

1124 Watson St, Key West