$299,900 Amazing BUSINESS Opp built over the past 5 yrs in the heart of Islamorada & the Keys (Ocean Reef to Big Pine Key) A Street Legal (Old Hwy) Golf Cart Rental Co ready for its new owner to ROLL with! Included in this Business Sale: 7 Luxury Golf Carts Lithium ECO Battery & Gas Carts valued at appx 14k ea. They are 2023 or newer which sell for appx 20k per cart- 8X16 Single Wide Trailer valued at appx $2K-tent valued at appx $5K. Also included: Name, Logo, Website, All Social Media, Marketing, Phone Number & Clients. Current owner will work with new owners making sure all networks built over decades of Keys experience and knowledge is passed on. Expenses are limited to Rent, Insurance and Phone. There are no other golf cart rental companies like it in the Upper and Middle Keys! RIDE in Style! A11877016 MLS Amazing BUSINESS Opp built over the past 5 yrs in the heart of Islamorada & the Keys (Ocean Reef to Big Pine Key) A Street Legal (Old Hwy) Golf Cart Rental Co ready for its new owner to ROLL with! Included in this Business Sale: 7 Luxury Golf Carts Lithium ECO Battery & Gas Carts valued at appx 14k ea. They are 2023 or newer which sell for appx 20k per cart- 8X16 Single Wide Trailer valued at appx $2K-tent valued at appx $5K. Also included: Name, Logo, Website, All Social Media, Marketing, Phone Number & Clients. Current owner will work with new owners making sure all networks built over decades of Keys experience and knowledge is passed on. Expenses are limited to Rent, Insurance and Phone. There are no other golf cart rental companies like it in the Upper and Middle Keys! RIDE in Style! 0000 Overseas Highway, Islamorada
$849,000 This exceptional canal-front vacant lot on Lower Matecumbe Key represents a truly prime piece of cleared real estate. The permit for this property is being picked up 6/12/26. Seize this rare opportunity to build your dream home in a highly sought-after Keys location. B26046353 MLS This exceptional canal-front vacant lot on Lower Matecumbe Key represents a truly prime piece of cleared real estate. The permit for this property is being picked up 6/12/26. Seize this rare opportunity to build your dream home in a highly sought-after Keys location. 149 Iroquois Drive, Islamorada
$710,000 Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income producing condotel in the Sport Fishing Capital of the World. This 27-acre oceanfront Islamorada resort set in a lush tropical landscape has everything from fine dining restaurants, spa and wellness, fitness center, three resort style pools, two tiki bars, par 3 golf course, four lighted tennis courts, pickleball, basketball, bicycles, huge pier for fishing, kayaking, paddleboarding, and more. This top floor corner unit is a beautifully appointed one king bedroom with expansive master bath, kitchen and private screened in balcony. Accomplished on-site professional management has delivered high occupancy and rental rates far above many other lodging properties in the Keys! 1 Beds ⋅ 1 Baths ⋅ B26036550 MLS Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income producing condotel in the Sport Fishing Capital of the World. This 27-acre oceanfront Islamorada resort set in a lush tropical landscape has everything from fine dining restaurants, spa and wellness, fitness center, three resort style pools, two tiki bars, par 3 golf course, four lighted tennis courts, pickleball, basketball, bicycles, huge pier for fishing, kayaking, paddleboarding, and more. This top floor corner unit is a beautifully appointed one king bedroom with expansive master bath, kitchen and private screened in balcony. Accomplished on-site professional management has delivered high occupancy and rental rates far above many other lodging properties in the Keys! 81801 Overseas Highway Highway Unit 714, Islamorada
$1,300,000 A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout living areas. Eat in kitchen offers large island, snack counter and full size wine cooler. Dishwasher installed 12/25. There is also a hot water dispenser. Dining area and living area open to enclosed patio with private spiral staircase leading to resort styled amenities. Impact glass on all windows. Primary bedroom offers more spectacular views, built in furnishings and is 14x14. Modification in primary bathroom leads to large walk in closet. Washer replaced 2025, dryer 2024, AC 2021. Building inspections complete with no pending assessments. Private Marina dredged 2025. Outside storage cage included. RARE covered parking. Enjoy resort style pool, hot tub, tennis, pickleball, nature trails, gazebos, boat ramp, clubhouse with fitness, pavilion with ice machine, docks rentable for up to 30ft boat (almost always available), tiki huts, electric vehicle chargers, guest parking, open lot for boat storage, and private marina. Chandelier in dining area excluded. Beach area overlooks marina. Owner agent. 2 Beds ⋅ 2 Baths ⋅ B26016320 MLS ⋅ Ocean Harbour BLDG. A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout living areas. Eat in kitchen offers large island, snack counter and full size wine cooler. Dishwasher installed 12/25. There is also a hot water dispenser. Dining area and living area open to enclosed patio with private spiral staircase leading to resort styled amenities. Impact glass on all windows. Primary bedroom offers more spectacular views, built in furnishings and is 14x14. Modification in primary bathroom leads to large walk in closet. Washer replaced 2025, dryer 2024, AC 2021. Building inspections complete with no pending assessments. Private Marina dredged 2025. Outside storage cage included. RARE covered parking. Enjoy resort style pool, hot tub, tennis, pickleball, nature trails, gazebos, boat ramp, clubhouse with fitness, pavilion with ice machine, docks rentable for up to 30ft boat (almost always available), tiki huts, electric vehicle chargers, guest parking, open lot for boat storage, and private marina. Chandelier in dining area excluded. Beach area overlooks marina. Owner agent. 87851 Old Highway Unit M5, Islamorada
$3,999,999 Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living. 2 Beds ⋅ 2 Baths ⋅ B26001957 MLS Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living. 77340 Overseas Highway, Islamorada
$50,000 A-1 Urgent Care & Family Practice Center - Islamorada, Florida KeysAre you a Doctor looking to purchase an established practice or know a Doctor in the Market? This Medical practice has ben established for 20 years and has steadily grown over time.Located in Islamorada, there are few other medical offices for clinics or pediatrics making this a very interesting opportunity for any interested Medical personnel. F10555238 MLS A-1 Urgent Care & Family Practice Center - Islamorada, Florida KeysAre you a Doctor looking to purchase an established practice or know a Doctor in the Market? This Medical practice has ben established for 20 years and has steadily grown over time.Located in Islamorada, there are few other medical offices for clinics or pediatrics making this a very interesting opportunity for any interested Medical personnel. 99198 Overseas Highway, Islamorada
$3,300,000 74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. Commercial fishing zoning allows for uses such as a restaurant, seafood market, marine outfitter, charter or fishing headquarters, or other enterprises aligned with the working waterfront. 3 Baths ⋅ R11164709 MLS 74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. Commercial fishing zoning allows for uses such as a restaurant, seafood market, marine outfitter, charter or fishing headquarters, or other enterprises aligned with the working waterfront. 74560 Overseas Highway, Islamorada
$1,150,000 ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking, metal roof & impact doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing! 2 Beds ⋅ 3 Baths ⋅ F10546467 MLS ⋅ Anglers Reef BLDG. ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking, metal roof & impact doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing! 102 Anglers Way, Islamorada
