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$665,000
2 Beds ⋅ 2 Baths ⋅ 620648 MLS
The lowest-priced condo currently available in highly desirable Building 4 This beautifully updated 2-bedroom, 2-bath D-model at Ocean Pointe is an exceptional opportunity. Featuring two private balconies-a rare and highly sought-after feature. You'll enjoy extra outdoor living space along with beautiful ocean views, tropical breezes, and breathtaking Keys sunrises. Offered fully furnished and turnkey, this condo is ideal as a vacation home, income-producing investment, or both. The open floor plan features an updated kitchen, granite countertops, stainless steel appliances, and a full-size washer and dryer. Both bathrooms have been renovated, and impact-resistant windows and sliding glass doors provide added security and peace of mind. The unit also boasts a strong history of successful short-term rentals. Ocean Pointe is a gated, resort-style waterfront community that allows nightly rentals with no restrictions on owner usage or property management. Amenities include a protected marina with direct ocean access, boat ramp, dry boat storage, heated Jr. Olympic-size pool, 14-person spa, pool bar, oceanfront café and lounge, private beach, boardwalk, observation pier, lighted pickleball and tennis courts, and 24-hour security. Whether you're boating to the reef, fishing, diving, relaxing by the pool, or simply taking in the incredible ocean views, this exceptional condo offers the perfect combination of luxury, flexibility, and the ultimate Florida Keys lifestyle.

500 Burton Dr Unit 4208, Tavernier
$450,000
2 Beds ⋅ 2 Baths ⋅ 620647 MLS
2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

3312 N Northside Dr Unit 607, Key West
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 620645 MLS
Welcome to 273 W Seaview Dr, your sanctuary in the heart of tropical paradise! This concrete fortress, built to withstand hurricanes, ensures peace of mind in any weather. The 3/2 house, completed in 2020, boasts modern amenities and stylish finishes, offering both safety and spaciousness. This property is perfect for a vacation home, allowing you to relax and enjoy the vibrant surroundings of Duck Key. The owner just recently added a pool as well. The sale of the property also included the garage connected to the property. Experience Florida's many attractions: no state income tax, an average of 230 sunny days annually, and stunning beaches. Duck Key also offers excellent public, private, and charter schools, as well as a welcoming, close-knit community. Embrace the island lifestyle and live securely and luxuriously in paradise!

273 W Seaview Dr, Duck Key
$739,000
2 Beds ⋅ 2 Baths ⋅ 620643 MLS
Two Oceanfront Balconies comes with this updated D model at Ocean Pointe. Remarkable Kitchen remodeling job , both baths too with Impact windows and sliders. Wow factor Ocean Views with all the amenities owners and guest want. Jr. Olympic pool with 14 person Spa, Pool Bar, Direct ocean access Marina with dry boat storage. Lighted Tennis & Pickle ball courts. Oceanfront Cafe & Lounge. No restrictions on owners use and No restrictions on who an owners uses to manage their property. This Condo is being sold fully furnished with Housewares. Use it as much as you like and rent it out when its not in use , it's the owners choice.

500 Burton Dr Unit 4206, Tavernier
$1,149,000
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
$259,000
620638 MLS
Live aboard boat slip offered in Sombrero Marina is 50' long accommodating up to 55' length boat; includes one allocated parking space. With beautiful views from your boat, enjoy all that Marathon has to offer. This slip is centrally located, and nearby you can play golf, go fishing and kayaking, spend a day at the beach, and more! End your days with a meal or a drink and some entertainment at The Dockside Bar and Grill located on premises. The Marina also has additional showers, restroom, and laundry available for use. Along with a dockmaster who can help with renting your slip out for additional income while you are not there. Current rental income for this slip size is $1,600/mo. Buyer is responsible for paying a 6% transfer fee to the state of Florida and there is a lease fee for the bay bottom. Don't miss out on this opportunity to live or invest in the Florida Keys at a low cost. *Boat is not sold with the slip- but owner is selling separately*

35 Sombrero Blvd Unit B31, Marathon
$549,500
1 Beds ⋅ 1 Baths ⋅ 620633 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This king bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 715, Islamorada
$600,000
2 Beds ⋅ 3 Baths ⋅ 620630 MLS
Don't miss this remodeled property with cheerful tropical touches that brighten every stay in the Florida Keys. This spacious two-story townhome offers 930 SF square of living space, approximately 30 additional SF than the typical 2 bedroom, 2 ½ bathroom properties in the area, making it an exceptional choice for a vacation getaway, investment property, or both. The home features a bright, open-concept first floor plan which includes a well-appointed kitchen equipped to satisfy even the pickiest chef, an expanded dining area, a comfortable living room, a convenient half bath, and a laundry closet with a washer and dryer. Upstairs the main bedroom with cathedral ceilings has an ensuite bathroom and porch, a second bedroom and a second bathroom have entrances on the hall. Enjoy the Florida Keys lifestyle from either the upstairs or downstairs private porches, where you can sip your morning coffee or unwind with a glass of wine while overlooking the sports fields and children's recreation area, which is currently being transformed into a water park. The enclosed backyard adds even more outdoor enjoyment and privacy. Centrally located in the heart of the Florida Keys on the grounds of Hawks Cay Resort, this townhome is within walking distance of restaurants, marina access, and a variety of water activities. Whether you're looking for a personal retreat, a vacation rental with excellent income potential, or the perfect combination of both, this property is ready to impress. Schedule your private showing today and discover all it has to offer!

7103 Harbor Village Dr, Duck Key
$549,500
1 Beds ⋅ 1 Baths ⋅ 620629 MLS
Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This double queen bed condotel, situated in the renowned Cheeca Lodge Resort and Spa, offers the perfect blend of luxury, convenience, and investment potential. Beautiful turn-key suite provides you with resort style living. Experience the epitome of luxury with 5-star dining options. Immerse yourself in the tropical paradise with 2 tiki bars, spa and fitness facility, and three heated swimming pools. Enjoy direct access to the beach and dock. Stay active with 6 lighted courts offering tennis, pickleball and basketball. Indulge in various water sports amidst lush tropical gardens. Nightly rentals allowed, providing a lucrative income stream. Onsite management ensures hassle-free property maintenance and guest services. Walking distance to outstanding restaurants, galleries, breweries, and boutiques. Proximity to Islamorada's famous art district adds cultural charm to the surroundings. Seize this rare opportunity to own a piece of paradise in one of Islamorada's most iconic and historic destinations.

81801 Overseas Highway Unit 716, Islamorada
$650,000
1 Beds ⋅ 1 Baths ⋅ 620626 MLS
A smart buy in the heart of the Upper Keys. This 1,429-square-foot single-family home sits on an oversized double lot (50x107 each) totaling 10,700 square feet -- a rare amount of land for Key Largo, offering room to expand, add a pool, or simply enjoy extra space that's increasingly hard to find on the island. Priced at a point that's tough to beat, it's ideal for an investor, first-time buyer, or anyone looking to build equity in one of South Florida's most in-demand markets. Sold as-is, this property is a strong candidate with the double lot adding meaningful upside for future development or expansion. Located in an X Flood Zone, the property offers a real advantage on insurance costs compared to many Keys homes in higher-risk zones -- a key factor for both owner-occupants and investors calculating carrying costs. Key Largo's year-round tourism and steady demand for both long-term and vacation rentals make this an opportunity worth a serious look. No direct water access further keeps carrying costs (insurance, HOA) more manageable than comparable waterfront listings nearby -- while still delivering easy access to Florida Bay, the Atlantic, and everything the Keys lifestyle offers just minutes away. Whether you're adding to a real estate portfolio or looking for an entry point into the Keys market with room to grow, 226 Lignumvitae is priced and positioned to perfom. Please call for details.

226 Lignumvitae Dr, Key Largo
$1,059,000
2 Beds ⋅ 2 Baths ⋅ 620624 MLS
A true Marathon canal-front classic, thoughtfully renovated for easy Keys living. This updated waterfront home offers 75 feet of dockage, a solar-powered boat lift, and no-bridge access to Boot Key Harbor and the Atlantic Ocean, making it an ideal setup for boaters, anglers, and anyone ready to enjoy the Florida Keys lifestyle. Upstairs, the bright open-concept living area features 2 bedrooms and 2 full bathrooms, new flooring, a refreshed kitchen with new appliances, and updated bathrooms with new vanities and fixtures. Impact windows and doors provide added peace of mind, while fresh interior and exterior paint, a new upstairs A/C system, and new ductwork enhance the home's comfort and functionality. The spacious lower level offers the flexible storage space every Keys owner appreciates--perfect for fishing gear, diving equipment, tools, paddleboards, bikes, and everything that comes with life on the water. Outdoor spaces are designed for relaxing, entertaining, and low-maintenance island living. Enjoy a rethatched tiki hut, an open patio finished with vinyl wood-plank decking, a new aluminum staircase and railing, a remote-controlled fence, a fenced backyard, and an irrigation system. Set on a 7,500-square-foot lot, the property offers plenty of room for boat and RV storage, additional parking, and everyday convenience. The home is being offered with furnishings negotiable, giving buyers the flexibility to create a turn-key retreat or personalize the space to their own style. Centrally located near Marathon restaurants, shopping, Sombrero Beach, Fishermen's Community Hospital, and all the best of the Middle Keys, the property works beautifully as a year-round residence, weekend getaway, or rental investment opportunity. With seven-day minimum rentals allowed, strong boating features, generous outdoor space, and thoughtful updates throughout, this canal-front home offers the flexibility, comfort, and Keys lifestyle buyers are looking for.

305 50th St, Marathon
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 620623 MLS
Single Family Residential Key Largo property with canal view. With FEMA MAP actualized and currently active since 02/18/2005. C3 Kitchen updated, bathrooms updated. Satisfactory condition for the age and type of structure. With canal frontage with dockage and inmediate open water access. Three bedrooms and two bathrooms and covered rear deck with canal view.

119 Peace Ave, Tavernier
$315,000
620621 MLS
50' X 22' boat slip at the World famous Lor E Lei marina. Excellent in-town location, you know you're going to boat over here anyway so you might as well tie up for the night! Enjoy the sunsets, unwind, Uber home, or use for your fishing business, so many possibilities. A rare find.

96 Madeira Rd Unit # 10, Islamorada
$989,000
2 Beds ⋅ 2 Baths ⋅ 620620 MLS
TURNKEY CANAL-FRONT RETREAT IN KEY COLONY BEACH! Welcome to your slice of paradise. Don't miss this incredible opportunity to own a fully furnished 2-bedroom, 2-bath half duplex on a desirable canal in Key Colony Beach. Whether your searching for the perfect vacation retreat, a full-time residence, or a high-demand investment property, this home offers it all Perfect for entertaining, the home features a spacious screened in outdoor patio, ideal for hosting family and friends. Unwind in the private Jacuzzi while enjoying the lush tropical landscaping that creates a peaceful oasis. Situated on a canal, this property offers the Keys lifestyle you've been dreaming of, with easy access to boating, fishing and waterfront living. Being offered fully furnished, this home is truly turnkey-just bring your toothbrush and fishing pole! Waterfront properties in Key Colony are in high demand making this an exceptional opportunity for both lifestyly buyers and savvy investors.

440 11th St, Key Colony
$489,000
2 Beds ⋅ 3 Baths ⋅ 620619 MLS
Discover breathtaking views from this stunning 2-story beach condo in The Cay, your private oceanfront community on Key Colony Beach. Nestled in a beautifully manicured, lushly landscaped courtyard, this well-maintained unit offers the perfect blend of luxury and low maintenance island living. Step inside to find a spacious living area with a convenient half bath on the first floor. Upstairs, enjoy two full bathrooms, including a private master bath in the large master bedroom. The generously sized second bedroom features its own balcony and accordion hurricane shutters. Natural light floods the interior, creating an open, inviting space ideal for relaxing or entertaining guests. Outside, an amazing terrace overlooks the sparkling pool, tropical gardens, and the Atlantic ocean beyond. Dine al fresco on your private balcony while taking in the stunning grounds of The Cay. This extraordinary property provides private white sandy beach access right outside your door, plus a refreshing pool for ultimate relaxation. With a 14-day minimum rental period, this condo has excellent investment potential in one of the Florida Keys' most desirable locations. Bonus Key Colony Beach lifestyle - Enjoy your own stretch of pristine white sandy beach and the convenience of walking to restaurants, the marina, the par 3 golf course, and Sunset Park. This is coastal living at its finest - schedule your private showing today before it's gone!

601 W Ocean Dr Unit 312D, Key Colony
$4,995,000
4 Beds ⋅ 5 Baths ⋅ 620618 MLS
Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat with private interior elevator accessing all floors . Completely reimagined, this one-of-a-kind residence showcases exceptional craftsmanship, sophisticated design, and effortless waterfront living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living areas, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the home is designed for both everyday living and grand-scale entertaining. An oversized island anchors the chef's kitchen, complemented by custom European-style cabinetry, premium quartz countertops, and an impressive suite of appliances including a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker and wine refrigerator, and Perlick refrigerator/freezer drawers. The inviting family room features an electric fireplace and a custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry, creating an ideal space for entertaining. Throughout the home, travertine flooring, custom built-ins, abundant hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, HVAC systems, 12 hurricane-rated sliding glass doors, and a whole-house generator. The luxurious primary suite features a custom walk-in closet, while every bedroom enjoys private balcony access. A guest suite features a zero-entry shower, offering added comfort and accessibility. Beautifully tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance everyday living. Residents enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West
$4,400,000
3 Beds ⋅ 5 Baths ⋅ 620614 MLS
An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

218 Whitehead St, Key West
$599,000
2 Beds ⋅ 2 Baths ⋅ 620613 MLS
Beautifully updated and move-in ready, this elevated Key Colony Beach half duplex is the perfect blend of island charm, comfort, and value! Step inside to a bright, inviting main living area featuring an updated kitchen with stunning new granite countertops, creating the ideal space for gathering with family and friends. Priced at just $599,000, this is one of the best opportunities to own in one of the Florida Keys' most desirable waterfront communities. Offering 2 bedrooms, 2 bathrooms, and 1,031 square feet of living space, this home also features a brand-new metal roof for added peace of mind. The spacious primary suite includes a walk-in closet and a private balcony overlooking the backyard--the perfect place to sip your morning coffee or relax in the evening while enjoying the tropical breeze. The expansive lower-level living and entertaining area provides the ultimate bonus space to unwind after a day on the water, watch the game, host friends, or simply embrace the laid-back Keys lifestyle. The generous backyard provides plenty of space to design your own private tropical oasis--add a pool, lush landscaping, or an outdoor kitchen to create the Florida Keys retreat you've always imagined. Location is everything, and this home delivers! Just steps from the Cabana Club, waterfront parks, pickleball and tennis courts, playgrounds, golf, restaurants, walking paths, and all the amenities that make Key Colony Beach one of the most sought-after communities in the Florida Keys. Whether you're searching for a full-time residence, a vacation escape, or an investment property, this home offers an unbeatable combination of location, exceptional value, and lifestyle. Don't miss your chance to own your slice of paradise at an incredible price!

310 3rd St, Key Colony
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 620612 MLS
THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

1503 Atlantic Blvd, Key West
$1,049,500
3 Beds ⋅ 2 Baths ⋅ 620610 MLS
Gorgeous 3 bedroom 2 bathroom home on a spacious corner lot, with plenty of room for boats and RVs. Updated and remodeled bathrooms, open concept kitchen, laundry room and stainless steel appliances . This property is situated in one of the highest elevations in the area, Property is surrounded by beautiful mature trees and it has an in-ground heated pool, lots of space to enjoy the open air, just a block away from the community park and boat ramp. Enjoy ramp access for boat launching, fishing, kayaking or to just take in a spectacular sunset on the water! You can either walk, bike, or take a ride on a golf cart to the park/ramp area. You also have nearby, Founder's Park, with excellent recreation, boat ramp access, public beach, a huge pool as well as several local festivals throughout the year, FREE for local residents. Property features a VOLUNTARY HOA, $250 annually. Seller offering $10K in contributions towards buyer's closing costs!

157 Navajo St, Tavernier
$1,875,000
4 Beds ⋅ 4 Baths ⋅ 620609 MLS
Rare canal-front duplex on Duck Key's prestigious Indies Canal with 70 feet of new composite dockage, sweeping canal views, and deep-water access to both the Gulf and Atlantic. New roof, new AC, and precast concrete construction throughout -- this is a solid, storm-ready build with significant insurance advantages over at-grade alternatives and no deferred maintenance surprises. Two self-contained side-by-side units, each 2BD/2BA with in-unit washer/dryer, private canal-view balcony, open floor plan, and under-house storage. Unit 1 is fully renovated -- granite counters, stainless appliances, new Kitchenaide soft close cabinetry, updated baths, tile floors throughout. Unit 2 features upgraded tile floors and a bright open canvas with kitchen and baths ready for your finish. The options here are unusually flexible: rent both units for strong 28-day vacation rental income, live in one and let the other pay your carry, or convert the entire structure to a single-family waterfront compound -- there's even room for a pool. That kind of optionality, in a precast concrete above-flood building with a new roof and new dock, simply does not exist elsewhere on Duck Key. Monroe County 28-day minimum rental applies. Sold as a complete duplex; cannot be split.

126 N Indies Dr, Duck Key
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 620538 MLS
Waterfront 3/3 Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , Split level living layout which works great as in law quarters ,open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in wrap around porch overlooking the water. 60 ' of Canal Frontage. 2 car garage, New AC, New appliances, large yard area plenty of parking , 60' Private Dock , Beautifully remodeled. Member of Founders Park with access to pickleball. swimming Pool , Beach, tennis and more. Own your own slice of paradise

135 Tequesta St, Tavernier
$645,000
1 Beds ⋅ 2 Baths ⋅ 620608 MLS
Oceanfront Luxury at Ocean Isles Fishing Village! Private Marina and Boat Ramp. Welcome to Unit 111--a masterclass in elevated condo island living. Built brand-new in 2022, this stunning 1-bedroom, 2-full bathroom, 850 sq ft oceanfront condo delivers the ultimate Florida Keys lifestyle. With the gated complex prime due-south orientation, you'll wake up to expansive, views of the Atlantic Ocean right from your downstairs balcony, and private master suite balcony. Step inside this two-story sanctuary to find a meticulously crafted open-concept living space. The first floor features a fully equipped kitchen with granite countertops, elegant coastal flooring, and a pristine full bath. Upstairs, the oversized master suite serves as your private retreat, complete with a second full bathroom and panoramic ocean vistas. Built high above flood elevation with solid CBS construction, impact windows, and a metal roof, this turnkey property offers total peace of mind. What truly sets this property apart is the highly coveted 7-night minimum rental allowance. This is a massive advantage in the FL Keys market, offering incredible short-term rental income potential when you aren't soaking up the sun yourself. The 7-acre gated resort amenities are unparalleled in the Middle Keys. Spend your afternoons at the Olympic-sized elevated waterfront pool, boasting some of the most stunning ocean views in town. Boaters will love the on-site, newly updated marina, private boat ramp, assigned slips, and fish-cleaning stations. Unwind under the tiki huts, host friends at the outdoor grilling areas, or relax in the air-conditioned community clubhouse. Whether you're looking for a high-performing vacation rental or your own slice of paradise, this is your gateway to the Keys dream.

10877 Overseas Highway Unit 111, Marathon
$899,000
4 Beds ⋅ 2 Baths ⋅ 620607 MLS
Waterfront Duplex with Income Potential in Big Pine Key! Live the Florida Keys lifestyle while your investment works for you. Welcome to 31032 & 31034 Hollerich Drive, a beautifully maintained waterfront duplex offering the perfect combination of island living and exceptional income potential. Located on a peaceful canal just steps from the Big Pine Community Park, this unique property features two spacious 2-bedroom, 1-bath residences, each with its own private entrance, private outdoor shower, and thoughtfully updated interior. Both units showcase bright, open floor plans with updated kitchens featuring stainless steel appliances, and ample cabinetry, along with renovated bathrooms, comfortable living areas, and spacious bedrooms. Whether you're searching for a primary residence, vacation home, or investment property, this duplex offers endless possibilities. Step outside and enjoy the laid-back Keys lifestyle with tropical landscaping, expansive gravel parking with room for boats and trailers, a detached storage building, and a relaxing canal-front setting perfect for enjoying the ocean breeze. Spend your mornings with a cup of coffee by the water, launch your next boating adventure, or simply unwind in your own tropical oasis. This versatile property is ideal for: -Living in one unit while renting the other -Generating income by leasing both units -Creating a family compound or multigenerational retreat -Seasonal or long-term rental opportunities Conveniently located near the Big Pine Community Park, shopping, dining, world-class boating, fishing, and all the natural beauty the Lower Florida Keys have to offer, this property truly has it all. Whether you're looking to invest, retire, or embrace the island lifestyle full-time, this rare waterfront duplex offers flexibility, charm, and endless possibilities. Own your piece of paradise while letting your investment help pay for it!

31032 Hollerich Dr, Big Pine
$5,200,000
4 Beds ⋅ 4 Baths ⋅ 620606 MLS
Experience the PINNACLE of luxury waterfront living at this exceptional oceanfront residence on prestigious Flagship Drive. Completely reimagined with uncompromising attention to detail, this exquisite 4-bedroom, 3.5-bath home blends sophisticated design with the relaxed elegance of the Florida Keys. From the moment you enter, you'll be captivated by the expansive open-concept floor plan, breathtaking ocean views, and refined finishes throughout. Oversized 41-inch porcelain tile flooring, designer lighting, premium fixtures, and custom craftsmanship create a timeless, contemporary aesthetic that complements the stunning waterfront setting. The chef-inspired kitchen flows seamlessly into the spacious living area, making it ideal for both everyday living and entertaining. Walls of glass invite natural light while framing spectacular turquoise water views. The luxurious primary suite serves as a private retreat with serene ocean vistas and a beautifully appointed spa-inspired bath. Three additional bedrooms and office provide comfortable accommodations for family and guests. Outdoor living is equally impressive. Multiple covered terraces offer the perfect place to relax while enjoying ocean breezes and unforgettable sunsets. The resort-style pool is complemented by a charming tiki hut, creating an inviting setting for entertaining or unwinding after a day on the water. Boaters will appreciate the exceptional dockage featuring two boat lifts, providing convenient access to the Atlantic Ocean for world-class fishing, diving, and boating. A spacious two-car garage offers ample room for vehicles, storage, and recreational gear. Perfectly positioned in one of the Lower Keys most desirable waterfront communities, this remarkable residence delivers an extraordinary combination of luxury, location, and the ultimate Florida Keys lifestyle. Every detail has been thoughtfully curated, creating a move-in-ready waterfront masterpiece that is as elegant as it is in

1046 Flagship Dr, Summerland
$820,000
3 Beds ⋅ 2 Baths ⋅ 620605 MLS
Experience resort living at its best in this beautifully remodeled 3-bedroom, 2-bath condominium, Gulf-front Faro Blanco gated community. This move-in-ready completely updated home features new hurricane-impact windows and doors, shell stone flooring throughout, plantation shutters, custom closet organizers, and a gourmet kitchen with hardwood cabinetry, soft-close drawers, stainless steel appliances, granite countertops, breakfast bar, and built-in wet bar with beverage refrigerator. Updated bathrooms include granite countertops and Toto bidet toilets. Relax on the screened lanai with partial Gulf views. This exceptional condominium provides the perfect blend of luxury, comfort, and resort-style living in one of Marathon's most sought-after waterfront communities.

2000 Overseas Hwy Unit APT 4G, Marathon
$1,199,000
3 Beds ⋅ 2 Baths ⋅ 617789 MLS
Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb boat lift and a quick ride to Looe Key, American Shoal, and the Adolf Bush wreck. The 1232 sq ft home sits on a 6,000 sq ft lot and features hurricane-impact windows, offering peace of mind and energy efficiency. The home has been tastefully remodeled within the last two years, including new kitchen and new bathrooms. Additional major upgrades include 2-year-old A/C the roof is just 4 years old. Bright, inviting, this home is ideal for enjoying the relaxed island lifestyle with world-class boating, fishing, and diving right at your doorstep. The supply lift will make it easy to transfer items to the second floor.

24347 W Caribbean Dr, Summerland
$3,100,000
5 Beds ⋅ 3 Baths ⋅ 620602 MLS
Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan. The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level includes two additional bedrooms and one bathroom, all above flood, perfect guest quarters with a full kitchen. Brand new exterior paint! Enjoy 75 feet of deep-water concrete dockage equipped with a 15,000 lb boat lift, providing excellent boating access. The home is solid concrete construction with a metal roof, fenced yard, and plenty of room for a pool. Port Antigua is known for its exceptional amenities, including one of the best private beaches in the Keys and a community boat ramp. With immediate access to Florida Bay and quick proximity to the Atlantic Ocean, this property offers the ultimate Florida Keys lifestyle--boating, water access, and island living at its finest. If you are seeking a waterfront property that has great rental history, this is the one!

117 El Capitan Dr, Islamorada
$499,000
1 Baths ⋅ 620599 MLS
The time is now to jump into The Key West Commercial investment opportunity in the Heart of Duval Street. This is perfect for you, a fully leased commercial condo to a long standing Key West Tenant, with a proven track record. The office/retail condo is completely upgraded with a completely new AC system - air handlers and ducts. Brand new storefront windows and front door with new aluminum frame impact rated. All floors, walls and paint have all been upgraded.. New lights and drop ceiling. All of the leg work has been professionally done, now just invest and enjoy your returns. Unit does come with one dedicated covered parking spot in the gated garage. The association is professionally managed, and is currently painting the exterior of the buildings. Monthly association dues are coming down and currently 1,554 which does include outside insurance, common area maintenance and exterior building maintenance. This unit is done and ready for you, call today for more details and to set up a showing! Today is the Day! Please do not disturb tenant, thanks! Must sign NDA for all details on the current lease.

1075 Duval St Unit STE C22, Key West
$989,000
3 Beds ⋅ 2 Baths ⋅ 620596 MLS
Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. Situated on a quiet street within Breezeswept Beach Estates, this well-maintained 3-bedroom, 2-bathroom stilt home perfectly balances premier boating access with a peaceful, scenic setting. The property's positioning is truly distinct. While the back of the home centers around a deep-water canal optimized for quick navigation to open water, the front looks out over tranquil salt ponds--treating you to wide-open, mirror-like sunset views without the interruption of forward neighbors. This home has direct ocean side access or easily head out back to the Gulf for some backwater fishing or spending the day at the sandbar via Niles Channel or Pine Channel. This property will stand out as a your own piece of paradise, a pristine basecamp for the serious waterman or anyone seeking an authentic island retreat. Key Features Include: *The heart of the home features a sleek kitchen with stainless steel appliances, complemented by fully updated bathrooms, and fixtures throughout. *Large windows capture the distinct natural light of the lower keys, making the interior feel bright, airy, and connected to the water. Enjoy waterfront views from every room in the house. *Unwind on the expansive, screened back porch overlooking your canal, or catch the evening colors shifting over the salt ponds from the front balcony. *The ground level features a massive, 600 sq. ft. fully enclosed storage enclosure, giving you a secure, dedicated space for dive tanks, fishing gear, and all your workspace needs.

673 Indies Rd, Summerland