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$575,000
1 Beds 1 Baths 618227 MLS
Quaint Key West Condominium - Discover 815 Pearl Street Unit 2, a charming 1-bedroom, 1-bath residence in the heart of Old Town. Light fills the open-concept living area, which flows seamlessly to a lush brick-paved courtyard via French doors. The efficient kitchen offers modern appliances, while the bedroom is a comfortable retreat with an en-suite bath. Enjoy your private fenced yard with space for alfresco dining, plus access to a shared pool surrounded by tropical landscaping. Located just blocks from Duval Street, beaches, dining, and shopping, this turn-key condo balances tranquility and convenience. Off-street parking and a low HOA fee (about $375/month, buyer to verify) make this an excellent value. Schedule your private showing today and experience island living at its finest!

815 Pearl St Unit 2, Key West

$535,000
2 Beds 2 Baths 618736 MLS
Welcome to your slice of paradise in beautiful Marathon! Perfectly situated near the airport for easy access, this thoughtfully remodeled CBS 2-bedroom, 2-bath home blends modern finishes with cozy coastal charm. Recently renovated with attention to detail, the interior features stylish updates, a warm and inviting ambiance, and a functional layout designed for comfort and relaxation. New Metal roof July 2024. Step outside to your private, fenced backyard oasis complete with a brick-paved patio and lush tropical landscaping -- including your very own banana tree. It's the perfect setting for morning coffee, evening cocktails, or entertaining under the island sky. Whether you're seeking a 7-day rental income opportunity or your own personal retreat in the Keys, this property offers flexibility, privacy, and island living at its best. Don't miss this opportunity to own a piece of paradise at an affordable price!

11231 2nd Ave, Marathon

$4,999,900
4 Beds 4 Baths 614893 MLS
Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chef's kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys' most sought-after locations.

75761 Overseas Hwy, Islamorada

$895,000
3 Beds 2 Baths 617033 MLS
Islamorada Tropical Retreat! Rare 3-bedroom 2-bath split plan condo in desirable Futura Yacht Club. Also available with a 39 ft. boat slip with a 24,000 lb boat lift as MLS#620148 for $1,100,000. Located in the heart of Plantation Key, this condo is in one of the most coveted boating locations in the Florida Keys with crystal clear water, spectacular nightly sunsets and easy boating access to both the bay and the ocean! This spacious condo is nicely updated inside and offers a private balcony overlooking the sports courts, grounds and gardens. Owners and renters alike enjoy the abundant community amenities, including an easy boat ramp, onsite boat/trailer storage, a huge pool with poolside club area, kayak storage, tennis and basketball courts and spacious grounds with shady picnic areas. After a day on the water, grab a cocktail and stroll over to the sandy beach area with sunset seating and shaded hammocks to enjoy spectacular Florida Keys sunsets! This first level condo allows for easy access via a single flight of nearby stairs or take the elevator to the lobby. Don't miss this opportunity and make sure you see the property video and 3D tour. Call today to arrange a private showing.

88540 Overseas Highway Unit 101, Islamorada

$1,710,000
4 Beds 2 Baths 617353 MLS
Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring by paddleboard or kayak, or heading out on your boat to world-class fishing and diving, this location makes it effortless. The backyard is designed for relaxation and connection, featuring a pool, spa, and multiple outdoor patio areas, all surrounded by lush, mature tropical landscaping. Inside, the home features a renovated kitchen, bright open living spaces, and a large enclosed back porch that extends your living area and overlooks the pool, spa, and canal. With four bedrooms, generous square footage, and seamless indoor-outdoor flow, the home is ideal as a primary residence, seasonal getaway, or investment property with tremendous upside. Located just minutes from Key West yet surrounded by the peace and natural beauty of Sugarloaf, this property offers the best of both worlds—space, privacy, and direct water access that's hard to find, along with the freedom to create your ideal island retreat.

1481 Sugarloaf Blvd, Sugarloaf

$375,000
1 Baths 615934 MLS
For the first time in 62 years Mr. C's Homemade Ice Cream is now being offered for sale representing a once-in-a-lifetime turnkey, legacy business. Located in one of the most highly visible shopping centers in Islamorada. Right across from Founders Park. This iconic, charming, and nostalgic ice cream shop has been a local favorite and a must-stop for visitors for over six decades. Everything is made in-house from the rich, creamy ice creams to the tropical gelatos and sorbets and signature waffle cones. This is a venture with a tremendous upside for a new owner ready to take it to the next level. Whether you're a hands-on operator, brand-builder, or investor seeking a location in the Keys with built-in cash flow and brand equity. The business name, FF&E, and recipes are included in the sale.

86701 Overseas Hwy Unit Unit 101, Islamorada

$414,000
1 Beds 1 Baths 618531 MLS
Experience the best of the Florida Keys boating lifestyle at this updated waterfront 1 BR and 1 BA remodeled and beautifully updated condominium in Marathon, Florida. Nestled along a peaceful 200-foot-wide deep-water canal with 6+ feet of control depth and no bridge restrictions, this Coco Plum Middle Keys retreat offers direct boating access ideal for sailboats, sportfish vessels, and cruisers. The water front condo includes an assigned boat slip accommodating vessels up to approximately 43 feet, making it easy to enjoy world-class fishing, sandbar excursions, and sunset cruises right from your backyard. Inside, sliding glass doors fill the home with natural light and open to a private waterfront balcony overlooking the canal. Coastal finishes and a turnkey design create a comfortable, low-maintenance space perfect as a primary residence, second home, or investment property. Air B&B host with all amenities, past and future guest bookings, and furnishings with the exclusion of a few personal items, can convey. Residents enjoy resort-style amenities including a heated pool, waterfront tiki huts with grilling areas, maintained dockage, and boat trailer parking. Located in Marathon in the heart of the Middle Keys, this waterfront condo is less than one mile from Coco Plum Beach and conveniently positioned along US-1, approximately 40 miles from Key West and 40 miles from Key Largo. Marathon International Airport, waterfront dining, shopping, and local marinas are all just minutes away. Private, peaceful, and ideally located, this rare Florida Keys waterfront condo combines deep-water dockage, rental flexibility, and effortless island living. Short-term rentals are permitted with a 7-night minimum, offering exceptional income potential in one of the Florida Keys' most desirable boating destinations (vacation rental license transfer subject to buyer inspection and governing authority approval). Seller is offering a $5,000 credit at closing- call for more details.

105 Ave D Unit APT 113, Marathon

$18,000,000
2 Baths 613627 MLS
''The Pulse of Islamorada'' ... Iconic Islamorada Restaurant & Cabana Bar available for Sale, Real Estate and Business included. Spanning over 1,000 feet of bayfront and 500 ft of Highway frontage, where the locals & visitors come from near & far to watch nightly sunsets over the bay, enjoy food & libations, and listen to live bands daily. This property includes over 5 acres of real estate (survey available), full service bar with 5 Cop liquor license, 250 seat outdoor restaurant, private party & tournament hosting area. New parking lot, lighting, & drainage completed in 2020 with plenty of parking to expand the business. Concrete building built in 2015/2016 for gift shop, bathrooms, laundry, prep kitchen, storage, and more. In addition, property includes main kitchen, special event tiki bar, dockage, beach, boat ramp, and more. Sale includes 4 on site building rights & 2 boat slips in the Islamorada Yacht Basin located adjacent to property. Room for expansion. Voted Best Sunset year after year. Additional information and financials available upon request. NDA and POF required. Contact Listing Agent . All information to be verified by Buyer/Buyer's Agent.

96 Madeira Rd, Islamorada

$6,750,000
607307 MLS
OCEANFRONT ACREAGE IN HEART OF ISLAMORADA! Discover a unique opportunity to own oceanfront acreage right in the heart of Islamorada, the jewel of the Florida Keys. This remarkable property encompasses over 7 acres of pristine upland, complemented by baybottom, and comes with a coveted building right, allowing you to create your dream estate. With an astonishing 700 feet of direct Atlantic beachfront, your oasis in paradise awaits. Nestled in the vibrant community of Upper Matecumbe Key, you have the canvas to craft your vision, with space for your main residence, a caretaker cottage, a detached guest house, a tennis court, and even a charming boardwalk leading to your very own private sandy beach. Not only does this piece of paradise offer unparalleled beauty and space, but it also boasts zoning that allows for weekly rental potential, making it a valuable investment. Seize the opportunity to make your waterfront dreams a reality in the Florida Keys. This is your chance to create a legacy estate that combines coastal luxury with the convenience of town living. Don't miss out on this once-in-a-lifetime opportunity!

82900 Old Hwy, Islamorada

$325,000
2 Beds 2 Baths 618497 MLS
You don't often hear 'affordable' and 'Duck Key' in the same sentence, but this top-floor end unit proves you can live on one of the Keys' most desirable islands without breaking the bank. The end-unit location means extra windows that flood the space with natural light, and your private patio is the perfect spot to unwind at the end of the day. Inside you'll find tile floors throughout, a full kitchen and two full bathrooms all in great shape. Both bedrooms are generously sized and can each accommodate king beds with room to spare. Here's where it gets really good. Everything you could want with island living is just steps from your door. Start your morning at the Club Duck Key pool or play pickleball with neighbors. If you want access for boating, Duck Key Marina has dry rack storage with easy in-and-out service. The newly remodeled Hawks Cay Marina offers wet slips, a boat ramp, and Angler & Ale restaurant overlooking the marina—perfect for lunch, dinner or happy hour. This is the luxury resort-style living that Duck Key is known for, and it's all within walking distance at a fraction of the price.

1129 Pebble Beach Lane, Unit 12, Duck Key

$2,160,000
4 Beds 4 Baths 618235 MLS
Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels both timeless and current. LOCATED IN X Behind its unassuming facade lies a surprisingly expansive interior offering four bedrooms and four baths, including three bedrooms with three baths on the main level and a private upstairs bedroom with its own bath, ideal as a guest suite, apartment-style retreat, or income-producing space. An additional office or flex space off one of the bedroom suites allows work and relaxation to coexist effortlessly. The single-level main floor is designed with intention each bedroom enjoys privacy while remaining easily accessible. Interior details include travertine and Ipe Brazilian hardwood floors, wood-clad ceilings, and a gourmet kitchen outfitted with stainless steel appliances and a wrap-around peninsula that naturally becomes the heart of the home. Whether hosting friends or enjoying everyday living, the flow is intuitive and inviting. French doors throughout the home create a strong connection to the outdoors. One bedroom opens directly to the pool, while another enjoys a peaceful, tucked-away deck perfect for morning coffee or quiet reflection. The primary suite is a true sanctuary, featuring vaulted ceilings, a spacious marble bath with multi-jet shower, walk-in closet, and direct access to an expansive Ipe sundeck. Outside, a large heated pool anchors a lush, private oasis surrounded by tropical landscaping and a privacy fence ideal for entertaining or unwinding in complete tranquility. A shaded loggia adds yet another layer of livable outdoor space. Off-street parking, LOCATED IN X FLOOD ZONE provides rare Old Town convenience!

1209 Packer St, Key West

$419,000
2 Beds 2 Baths 616979 MLS
Welcome home to your island retreat - a beautifully appointed 2-bedroom, 2-bath condo at Landings of Largo. Curated with modern coastal décor and ideal as a second home or a weekend escape from the city. This light-filled residence features a split floor plan offering privacy and comfort, with stylish touches throughout. The open kitchen boasts butcher block countertops, a tile backsplash, and a fresh, breezy aesthetic that reflects the laid-back elegance of coastal living. Just steps from the pool, this unit offers unmatched convenience within a resort-style community that feels like a permanent vacation. Enjoy access to two heated pools, tennis, pickleball, basketball, bocce courts, a fitness room, clubhouse, and outdoor grilling areas—all set within lush, tropical landscaping. Unit comes with two reserved parking spaces and guest parking is also available. Boaters and anglers will appreciate the private marina, recently renovated and complete with a boat ramp, fishing pier, and fish cleaning station. Launch boats or jet skis from the wide boat ramp with convenient 72-hour trailer parking. Cap off each day with breathtaking sunset views over the bay from the community's exclusive sunset dock. Ideally situated just a short one-hour drive from Miami and major airports, this Key Largo gem places you at the heart of it all. Enjoy effortless access to the area's top dining, shopping, world-famous fishing and scuba diving. Don't miss this opportunity to own your own slice of paradise in the Upper Keys.

98422 Windward Ave, Key Largo

$859,000
2 Beds 1 Baths 618512 MLS
Located in one of Key West's newer developments at The Captains House in Bahama Village, this second floor, single level condo blends crisp renovation with classic island style. Completed in 2023, the interiors pair hardwood and Spanish style tile flooring for an easy, low maintenance flow from living space to kitchen and bath. The kitchen is finished with quartz countertops, stainless steel appliances, an amazing view of the Key West Lighthouse perfectly framed from the kitchen sink, and a Spanish inspired tile feature brings warmth, texture, and color into the main living area. The bathroom continues the same design story with tile wrapping the glass enclosed shower, plus a quartz topped vanity and modern fixtures. Outside, an open-air rooftop deck is reserved exclusively for Unit #4. This signature feature is an elevated outdoor living space tucked away in the treetops for morning coffee, breezes at sunset, and stargazing at night. Separate stairs visible at the roofline serve another unit, while this deck space remains private to Unit #4. It's in the X Flood Zone, Pets are allowed with restrictions, and it's just a short walk to Ft. Zach Beach, Truman Waterfront Park & Duval Street for all the great restaurants, shopping, and live entertainment..

927 Thomas St Unit #4, Key West

$2,850,000
4 Beds 4 Baths 614443 MLS
One of the most sought-after canal properties in Jupiter. Welcome to 934 Penn Trail, a captivating waterfront residence in the heart of Jupiter, Florida. This single-story home, built in 1986, offers 2357 sq ft of living space, featuring 4 bedrooms and 2 full bathrooms and 2 half bathrooms. Interior highlights include an open floor plan, fireplace and a fully equipped kitchen as well as four comfortable bedrooms. The expansive outdoor space features a deck and patio as well as a screened porch for outdoor entertaining Florida style. Direct canal frontage and ample dock space with no fixed bridges to open water makes for unparalleled boating access. This home is located close to top rated schools, shopping, dining and recreational facilities.

934 Penn Trl, Other

$7,000,000
3 Beds 4 Baths 616249 MLS
An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity—an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter. The property is currently undergoing a full renovation with permits and detailed architectural drawings already in place, giving the next owner a priceless advantage: step in at the perfect moment to bypass years of costly planning, engineering, and permitting delays. The most complex and time-consuming site-work has already been completed. With the structure, dockage, and infrastructure well underway, you can now take the reins of a project designed to become one of the most iconic private estates in the Florida Keys. Spanning over 5 acres, this private island offers a main residence with soaring wood-beamed ceilings, panoramic water views, and open-air living powered entirely by solar. From sunrise over the Atlantic to sunsets over the Gulf, the views are endless and unforgettable. The elevated observation deck delivers dramatic 360-degree vistas, perfect for entertaining, stargazing, or simply enjoying total seclusion. The seller has already invested heavily to bring the island to this stage and the estimate is $1.8M anticipated to complete renovations. For a discerning buyer, this creates a rare chance to secure Melody Key at precisely the right moment—capturing significant upside and finishing the project exactly to your vision. There is a private airport in the neighborhood for those with private planes. The property comes with a full residential lot on a canal for boat launches with a seawall located at 1439 Hudgings Dr. Opportunities of this exclusivity simply do not exist elsewhere in the Keys. Melody Key is not just a property—it is a legacy waiting to be completed.

Melody, Summerland

$6,495,000
3 Beds 3 Baths 608546 MLS
Beautiful 200' of oceanfront property on Lower Matecumbe Key. This offering consists of one 100' lot, vacant with TDR & contiguously, a 100' lot with a triplex apartment building (3 TDRs),.This gives you endless possibilities for redevelopment of the property. The vacant lot has an additional 200' of bay bottom. Fantastic 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Recap: 200' of oceanfront made up of 1 vacant lot with TDR, 1 lot with 3 apartments, bay bottom on the vacant lot, for a total of 4 TDRs on the property Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada

$1,395,000
617612 MLS
An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west and 1.25 acres of lush protected vegetation on-site. A former 2,700 square foot residence once occupied the site and was later demolished with permit in 2021 after sustaining damage during Hurricane Irma. A ROGO Exemption Letter is in place, eliminating the wait to build. A single family home permit application was submitted in 2022 and can potentially be reopened or transferred to a new owner with the County. The U.S. Army Corps of Engineers previously approved a 412 foot dock permit in 2019, offering tremendous potential for future dockage. Plans for a residence, ACOE documentation, and dock drawings (including a 16,000 lb boat lift) are available upon request. Zoned Improved Subdivision, one dwelling unit may be built with a twenty percent open space requirement. This rare acreage invites imagination, whether creating a luxury waterfront retreat, private family compound, or legacy estate to hold for generations. With unmatched open water views, bay bottom rights, ROGO exemption, and a location rarely offered, this is a blank canvas for an extraordinary Keys estate. A once in a lifetime opportunity to build now and craft your vision on one of the most unique properties available in the Lower Keys.

1261 Ave A, Big Pine

$8,750,000
618856 MLS
Waterfront motel and marina property in Marathon offered with thirteen transferable transient building rights, highway frontage, and redevelopment potential. Sea Cove is located on Overseas Highway with approximately 200 feet of US-1 frontage, more than two acres of buildable uplands, and additional bay bottom ownership. The property has a long history of marina and lodging use and includes an existing boat ramp with direct boating access. The site has historically supported motel operations, marina services, and small retail activity. The offering includes the real estate together with thirteen transferable transient building rights that allow nightly rental use within the City of Marathon, subject to zoning and City approval if relocated. Previous planning and engineering work studied redevelopment of the site as a marina focused project. Concept plans illustrate a dry boat storage structure of approximately 33,000 square feet accommodating roughly 150 dry racks together with approximately 30 wet slips. Prior discussions have also included extended dockage approaching 550 feet and potential marina services including fueling facilities, subject to required approvals. The site includes significant waterfront area together with bay bottom ownership that has historically supported dockage and marina activity. Showings by appointment only. Please do not visit the property or speak with employees without listing agent present.

12685 Overseas Hwy, Marathon

$1,000,000
618582 MLS
Seller Financing possible. Commercial Mixed Use lot with seafood business, now available. Sale includes business, traps, both lobster and crab tags, 43' Torres boat and all equipment. Lot is part of the Fisherman's Pointe HOA ($800.00 annually) which includes a deeded and assigned boat slip at the newly renovated pier. Property has both water and sewer as well as a separate electric meter. The Mixed Use-Maritime (MU-M) zoning district is designed for areas essential to the commercial maritime industry, including boat storage, seafood processing, fishing equipment sales, and related retail, restaurant, and affordable housing uses. It encourages a pedestrian-oriented mix of commercial and maritime activities. The MU-M district is part of the City's broader efforts to manage water access and protect its maritime heritage.

212 20th St, Marathon

$2,450,000
3 Beds 4 Baths 616722 MLS
Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and convenience for family and guests. Beyond its beauty, this property is one of the rare few in Monroe County allowing nightly vacation rentals, boasting a highly successful rental history for those seeking both personal enjoyment and income opportunity. Every detail has been thoughtfully curated, impact windows and doors, corian countertops and two on-demand water heaters reflect quality and peace of mind. The boating enthusiast will appreciate one of the few marked channel systems leading directly to the Gulf of Mexico with the Atlantic Ocean just minutes away. Utilize the 220 sq ft extended dock for your vessel to some the best fishing, diving and boating in the continental U.S. Whether lounging poolside, entertaining on the spacious decks or heading out on the water this property offers an unmatched Keys experience. Rare, refined and ready for your investment this is open-water living at its finest.

31473 Warner Rd, Big Pine

$9,500,000
7 Beds 4 Baths 579482 MLS
Beautiful adjoining oceanfront gated estates available individually or together. Each parcel has a single family residence with vacation rental income potential and are zoned Suburban Commercial for development opportunities..*UPDATE: There are 50 TDRs (TREs) available, preliminarily reviewed by Monroe County and transferable to these parcels for higher development potential! This unique wooded acreage has a deep basin and channel for ocean access, with dolphin piling boat slips and boat ramp. Single Family Residences with ROGO exemptions for remodel/rebuild possibilities. Highest approval rate via Monroe County is for MIXED-USE COMMERCIAL development. (The 6.1 acre parcel may be sold together with contiguous 3.2 acre parcel@95325 Overseas Hwy, AK#1592986,RE#00483360 000000 13 62 38 PT TR 5&6 SOUTHCLIFF ESTS PB2-45 & PT GOV LOT 1 & ADJ BAY for grand total of 9.36 acres, includes 1137 sf 1970 2/1 cbs home, metal roof.) *Includes data for both parcels and for taxes. This is a duplicate listing. Broker part owner/family owned.

95351 Overseas Hwy, Key Largo