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88500 Overseas Highway Unit 208, Tavernier
$499,900
2 Beds ⋅ 2 Baths ⋅ 620763 MLS
Welcome to Summer Seas, a desirable waterfront community in the heart of the Florida Keys! This beautifully maintained 2-bedroom, 1.5-bath condominium offers the perfect blend of comfort, convenience, and island living. Enjoy a bright and inviting layout with an open living area, comfortable bedrooms, and a private balcony to relax and take in the tropical surroundings. The community features waterfront amenities, including a marina, pool, and easy access to the beautiful waters of the Florida Keys. Conveniently located near restaurants, shopping, boating, and everything Islamorada and Tavernier have to offer. Whether you are looking for a full-time residence, vacation getaway, or investment opportunity, this charming Keys retreat is ready to welcome you home.

88500 Overseas Highway Unit 208, Tavernier

701 Spanish Main Dr Unit 602, Cudjoe
$499,000
2 Beds ⋅ 1 Baths ⋅ 622015 MLS
Oceanfront Paradise Awaits! Unit 602 in Venture Out Experience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home with ocean views from the backyard home boasts: * Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 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 well cared for 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! * Plenty of rental income!

701 Spanish Main Dr Unit 602, Cudjoe

82770 Old Hwy, Islamorada
$499,000
621992 MLS
PRIME ISLAMORADA LOCATION | VILLAGE CENTER ZONING Excellent opportunity to own a 75' x 75' parcel comprising approximately 5,625 square feet in the heart of Islamorada, Florida Keys. This fenced and landscaped property offers an attractive setting in a desirable central location. Reportedly zoned Village Center (VC), a designation intended to accommodate a mix of commercial and residential uses, subject to applicable land development regulations and Village approvals. Whether you're an investor, business owner, or buyer exploring future possibilities, this property presents an opportunity to establish a presence in the Florida Keys. Buyer Due Diligence: All information, including but not limited to zoning, lot dimensions, permitted uses, development potential, building rights, availability of utilities, environmental restrictions, and applicable permitting requirements, is provided for informational purposes only and is not guaranteed by Seller or Listing Broker. Buyer and Buyer's representatives are responsible for independently verifying all information with Islamorada, Village of Islands, and other appropriate authorities. No representation or warranty is made regarding suitability for any particular use or the availability of development approvals.

82770 Old Hwy, Islamorada

701 Spanish Main Dr Unit 154, Cudjoe
$499,000
2 Beds ⋅ 2 Baths ⋅ 621700 MLS
Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean. Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private deck—an ideal spot for your morning coffee or evening entertaining. This tropical retreat sits on a large, lushly landscaped corner lot, offering both privacy and ample space. The home itself is in excellent condition and is move-in ready, featuring modern, high-end appliances and the peace of mind that comes with accordion hurricane shutters. The versatile layout includes significant bonus space underneath the house, perfect for storage, entertaining, working on projects or just relaxing in the shade in your hammock. This is not just a home; it's a prime investment. With nightly rentals allowed and plenty of opportunities for success on platforms like Airbnb and VRBO to help offset your costs. Don't miss your chance to own a piece of paradise. Schedule your private showing today!

701 Spanish Main Dr Unit 154, Cudjoe

473 W 105th St, Marathon
$499,000
2 Beds ⋅ 2 Baths ⋅ 621543 MLS
If you've been looking for a newer-construction Keys home that checks all the practical boxes--built above flood, impact windows and doors, and central air--473 W 105th St. in Marathon is worth a serious look. Built in 2022 to the latest building code, this 2-bedroom, 2-bath home offers 1,120 square feet of comfortable, low-maintenance island living with the peace of mind that comes from modern construction standards. Inside, the open living and dining area flows naturally into a full kitchen with rich wood cabinetry, dark countertops, and a complete appliance package. Crown molding and vinyl plank flooring run throughout the home, giving it a clean, finished feel. A dedicated laundry room with full-size washer and dryer adds everyday convenience. Outside, covered parking for two vehicles underneath the home on a concrete slab, plus additional off-street parking, provides practical storage and convenience. Located on the ocean side of Marathon at Mile Marker 53 with no HOA, this is a solid opportunity to own a move-in-ready Keys home built to modern standards. Please note: The above-ground pool and artificial turf shown do not convey with the sale.

473 W 105th St, Marathon

3312 Northside Dr Unit APT 707, Key West
$499,000
2 Beds ⋅ 2 Baths ⋅ 621440 MLS
Stunning Renovated 2-Bedroom Condo with Panoramic Ocean Views - Key West, FL Welcome to your slice of paradise! This beautifully renovated 2-bedroom, 2-bath condo on the 7th floor offers breathtaking, unobstructed ocean views and the best of island living in Key West. Step inside to find a bright and airy open-concept living space, complete with modern finishes, sleek tile flooring, and expansive windows that flood the unit with natural light. The updated kitchen features granite countertops, stainless steel appliances, custom cabinetry, and a stylish backsplash--perfect for entertaining or relaxing with a view. The spacious primary suite includes ocean views, a nice closet, and a en-suite bath. A second bedroom and full bathroom make this an ideal space for guests or a home office. Enjoy your morning coffee or evening wine from your private balcony overlooking the turquoise waters of the Atlantic. The condo also offers resort-style amenities including a pool,secure entry, and open parking. Located just minutes from Key West's world-class dining, shopping, and entertainment, this condo is your dream home in the heart of the island. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this one has it all. Don't miss your chance to own this ocean-view gem--schedule a private showing today!

3312 Northside Dr Unit APT 707, Key West

329 25th St, Marathon
$499,000
3 Beds ⋅ 3 Baths ⋅ 620207 MLS
Fabulous opportunity to live in the heart of the Keys in Marathon, Florida. This 3-bedroom, 2.5-bath townhome is located in the desirable gated community of Sisters Creek and offers one of the best locations in the neighborhood, situated right next to the resort-style pool. Enjoy open-concept living with an eat-in kitchen, pantry, all-wood cabinetry with pull-out drawers, stainless steel appliances, and a conveniently located half bath on the main living level. An additional den/office area provides flexible space for work, guests, or relaxation. Multiple exterior decks overlook the pool area and manicured tropical grounds, creating the perfect setting to enjoy the Keys lifestyle. A welcoming foyer entry leads to an interior staircase and the main living areas above. On the first level, you will find a substantial 12' x 16' enclosed storage room, providing exceptional space for bicycles, fishing gear, paddleboards, tools, holiday decorations, and all of your Keys lifestyle essentials. This detached townhome also features understory parking for two vehicles, gated entry with an electric security gate, and excellent access to Marathon's marinas, shops, restaurants, and nearby amenities. With a low HOA fee of just $302 per month, this home checks off so many boxes. Centrally located approximately one hour from Key West and one hour from Key Largo, you can enjoy the very best of the Florida Keys from this convenient Marathon location.

329 25th St, Marathon

63 Sugarloaf Dr, Sugarloaf
$499,000
617936 MLS
Welcome to the lowest priced waterfront lot with an active building permit and DEP and Army Corp mitigation fees paid on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq. ft., 4-bedroom, 3-bath coastal-style home -- with Army Corps dock approval already secured. Build today or customize plans to suit your vision. Sugarloaf Key is beloved for its larger lots, upscale homes, and stunning natural beauty. Enjoy crystal-clear water, endless mangrove creeks perfect for paddleboarding or kayaking, and the convenience of being just 15 minutes from Key West. The neighborhood is quiet, well-maintained, and filled with luxury homes offering the perfect setting for full-time living, a vacation retreat, or investment property. Opportunities like this are rare, a cleared path to build in the most coveted location in the Lower Keys. Create your ideal Florida Keys dream home now while you still can!

63 Sugarloaf Dr, Sugarloaf

10877 Overseas Highway Unit 7, Marathon
$499,000
1 Beds ⋅ 2 Baths ⋅ 614101 MLS
Price Improvement! This townhouse is enjoying a strong rental season and is attractively priced for an investor or owner-user. Call for details. Breathtaking townhouse with 7 DAY RENTALS ALLOWED, 1 BR 2 Bath on 7-acre waterfront complex located oceanside in Marathon, Fl. This retreat is designed to accommodate 4 people and is steps away from open ocean views, where you can fish off the docks, lounge under one of the many Tiki huts, or cool off in the swimming pool that overlooks the Atlantic. The clubhouse is equipped with a ice machine along with convenient grilling stations to cook your fresh catch. The vacation rental market in Marathon provides flexibility for those interested in generating additional income and allows for seven day rentals. This unit is set up for rentals with the City of Marathon and has a fantastic rental history available for review. Ocean Isles has easy access to the water with a private boat ramp for owners, allowing you to conveniently take your vessel in and out of the water. With protected boating access for owners at the Marina, featuring a new seawall, bulkhead, and docks, you'll have smooth sailing for all your water excursions. The central location of Ocean Isles in Marathon makes it the perfect home base for exploring all the Florida Keys. This townhouse has a Washer and Dryer hookup ready to go or there is a laundry facility available on the property.

10877 Overseas Highway Unit 7, Marathon

140 Tavern Dr, Key Largo
$498,000
1 Beds ⋅ 1 Baths ⋅ 621765 MLS
A rare opportunity to own a piece of Florida Keys history in the heart of Historic Tavernier. Built in 1934, this authentic Keys cottage dates back to a remarkable chapter in Florida Keys history, and when homes were built with character, craftsmanship & materials that are increasingly difficult to find today. It was an era when Henry Flagler's Overseas Railroad still connected the islands, Ernest Hemingway was writing & fishing in Key West, & the Florida Keys were a quiet collection of fishing villages, artists, pioneers & people drawn to a different way of life. From the original Dade County pine to the architectural details that reflect its nearly century-old roots, this is a home with a story to tell. Surrounded by mature tropical landscaping, the property has that timeless, old-Keys charm that simply can't be recreated with new construction. And the location is just as special as the home itself. Tucked within Tavernier's established historic district, you're just a short stroll from Old Settlers Park, Cafe Moka, locally loved restaurants, Sunshine Market, shops & even a spa. It's the kind of community where you can step outside your door, walk to your favorite morning coffee spot, run into familiar faces & enjoy a slower, more connected way of life. And because this is the Keys, access to the water is never far away. A nearby small beach for residents to enjoy the ocean water as well as a launch offers access for kayaks or small skiffs, & a convenient larger boat ramp is just up the road. Additionally, a marina across the road provides an options for larger vessels. Tavernier also puts you right between Key Largo & Islamorada, giving you convenient access to the everyday essentials of both communities. For the person who appreciates historic architecture, original craftsmanship & the beauty of preserving something with a story, this is an opportunity to own something truly special.

140 Tavern Dr, Key Largo

389 N Anglers Dr Unit 210, Marathon
$495,000
2 Beds ⋅ 2 Baths ⋅ 621925 MLS
Welcome to your ultimate coastal retreat. This two bedroom, two bath top end unit offers the perfect blend of privacy, convenience, and an unbeatable Florida Keys location situated in the highly desirable Sombrero Beach area. This coveted top-floor end unit lets you enjoy premium peace and quiet with no overhead neighbors and fewer shared walls. The bright and airy living space features a massive window that frames beautiful views of the sparkling pool, flooding the home with tropical sunshine. Everyday living is a breeze with an in-unit washer and dryer. The unit also comes with assigned parking spaces and a designated storage closet, perfect for stashing your beach gear, fishing poles, and coolers after a day in the sun. The community spaces extend your living room, with a heated pool for year-round enjoyment, a welcoming clubhouse for hosting friends, and a classic tiki hut for a cool drink in the shade. Assigned boat dockage available on a first come, first served basis. Whether you are looking for a lucrative vacation rental, a seasonal getaway, or a permanent slice of paradise, this condo delivers the quintessential beach lifestyle.

389 N Anglers Dr Unit 210, Marathon

1306 51st St, Marathon
$495,000
2 Beds ⋅ 1 Baths ⋅ 619582 MLS
Updated, elevated, and centrally located, this 2-bedroom, 1-bath half duplex offers an appealing combination of durable construction, modern finishes, and flexible Keys living. Located in the heart of Marathon and surrounded by mature native landscaping, the residence features CBS construction, an elevated design, a concrete roof, impact-resistant windows, and a newer HVAC system. Inside, the thoughtfully remodeled interior offers an open, comfortable layout with gray faux wood plank flooring, granite countertops, stainless steel appliances, and clean coastal finishes. Two covered parking bays beneath the home provide convenient space for vehicles, a boat, trailer, bicycles, fishing equipment, paddleboards, and the recreational gear that comes with Florida Keys living. Additional open parking and RV or trailer parking add to the property's everyday functionality. With seven-day minimum rentals permitted, the residence offers versatility as a primary home, seasonal retreat, employee-housing solution, or investment property, subject to applicable regulations. Separate electric and water meters provide additional convenience. Ideally positioned near shopping, dining, marinas, beaches, the community boat ramp, and daily conveniences, this move-in-ready property places the best of Marathon within easy reach. The adjoining half duplex is also available for purchase, creating a rare opportunity to acquire the entire property for expanded housing, multigenerational living, or investment potential.

1306 51st St, Marathon

6800 Maloney Ave Unit 13, Stock Island
$489,000
3 Beds ⋅ 3 Baths ⋅ 621956 MLS
Enjoy the Key West lifestyle in the waterfront community of Harbour Shores! This 3-bedroom, 3-bath home offers 1,222 square feet of comfortable living space with vaulted ceilings, central AC, and six closets, a rare find in Key West! The open floor plan connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. This home includes deeded land ownership, meaning you own both the home and the land with no lot rent. Harbour Shores offers residents access to a private community boat ramp and available dock rentals. The monthly HOA fee of $230 includes cable, sewer, and common area maintenance. With three bedrooms, three full bathrooms, generous storage, and deeded land ownership, this property offers an appealing combination of space, convenience, and value.

6800 Maloney Ave Unit 13, Stock Island

11400 Overseas Highway Unit 116, Marathon
$489,000
620752 MLS
One of Marathon's most iconic restaurants is now available for sale -- a rare chance to own and operate what many consider the best restaurant in the Florida Keys. Frank's Grill has operated at its current location since 2006, when the owner/chef relocated from what was previously regarded as one of Marathon's premier dining destinations. Today, Frank's Grill serves as the anchor tenant of Towne Square Mall, one of Marathon's busiest shopping plazas -- home to a steady flow of daily foot traffic and anchored further by a U.S. Post Office. This sale includes all FF&E (furniture, fixtures & equipment), current inventory, and proprietary recipes/assets. Walk in and start operating day one. Property & Licensing: • Seating: 47 inside / 10 outside (57 total) • 2COP Beer & Wine license currently in place Lease Terms: • New 5-year lease signed May 1, 2026 • Tenant option to renew after year 3 (subject to Assignment approval) With nearly two decades of brand recognition, a loyal local following, and an unbeatable high-traffic location, the goodwill alone in this business justifies the asking price. Opportunities to acquire an institution like Frank's Grill rarely come to market.

11400 Overseas Highway Unit 116, Marathon

201 E Ocean Dr Unit 1-211, Key Colony
$489,000
2 Beds ⋅ 2 Baths ⋅ 620688 MLS
Welcome to Casa Clara, one of Key Colony Beach's most sought-after oceanfront communities, where relaxed island living meets resort-style amenities. This inviting 2-bedroom, 2-bath condo offers an exceptional opportunity to enjoy the Florida Keys as a full-time residence, vacation getaway, or income-producing rental. Enjoy ocean views and refreshing sea breezes from both side patios, creating a seamless indoor-outdoor lifestyle. The condo is being sold furnished, including housewares, making it move-in or rental ready from day one. Casa Clara is a well-established oceanfront community of 83 residences that has been recently and completely renovated, offering over 500 feet of private white-sand beach that is cleaned daily. Resort-style amenities include an oceanfront swimming pool, tennis and pickleball courts, shuffleboard, a fishing pier with cleaning station, elevator access, on-site management, and beautifully landscaped courtyards, all overlooking the Caribbean-blue waters of the Atlantic. The walkable Key Colony Beach lifestyle is second to none--enjoy peaceful beach days, sunset strolls, and easy access to restaurants, shops, parks, marinas, charter boats, and a par-3 golf course. 14-day rentals are permitted, providing excellent flexibility and strong rental demand. The community also offers ample parking, nearby boat trailer storage, and allows one pet (per association policy)--a valuable feature in an oceanfront condo. Whether you're lounging by the pool, walking the beach at sunset, or welcoming guests seeking an authentic Florida Keys experience, this Casa Clara condo delivers comfort, lifestyle, and long-term value.

201 E Ocean Dr Unit 1-211, Key Colony

701 Spanish Main Dr Unit 659, Cudjoe
$487,000
2 Beds ⋅ 2 Baths ⋅ 620156 MLS
Seller is Motivated! Coastal Charm Meets Modern Comfort Welcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key. Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed kitchen. Recent updates include a brand-new refrigerator, ample cabinetry, and a modern island bar with additional seating, perfect for entertaining family and friends. Built with both comfort and durability in mind, the home features a reliable metal roof and a large ground-level storage enclosure for all your island essentials. Step outside to your private backyard retreat, complete with low-maintenance artificial turf and a cozy seating area, ideal for enjoying the Florida Keys sunshine. This property is a proven income-producing vacation rental with strong rental history and future bookings already in place. In 2025, the home generated $43,257.28 in rental revenue. As of June 2, 2026, it has already produced $18,472.78 year-to-date, with 8 future reservations estimated to generate an additional $13,092.57 in rental income that will transfer to the buyer. Conveniently located near the front gate of the community, this home offers easy access for pet owners, with a quick path for walking dogs just outside the neighborhood. You're also within walking distance of Venture Out's outstanding amenities, including a heated saltwater waterfront pool, swimming lagoon, private boat ramp, tennis courts, pickleball courts, bocce courts, basketball courts, marina store, community center, and more. Whether you're seeking a personal island retreat, a seasonal getaway, or an investment property with immediate income potential, this home offers the perfect combination of comfort, convenience, and Florida Keys charm.

701 Spanish Main Dr Unit 659, Cudjoe

701 Spanish Main Dr Unit 182, Cudjoe
$485,000
1 Beds ⋅ 1 Baths ⋅ 613336 MLS
Oceanfront Paradise Awaits! Unit 182 in Venture Out Experience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community. This beautifully maintained home boasts: * Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall. * Community Boat Ramp and boat washdown station. * Spacious Florida Room: Expand your living space with a delightful air-conditioned Florida room, perfect for relaxing and soaking in the coastal breeze. * 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 meticulously cared for 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! Plenty of potential for rental income.

701 Spanish Main Dr Unit 182, Cudjoe

55 Boca Chica Rd Unit 132, Big Coppitt
$485,000
2 Beds ⋅ 1 Baths ⋅ 617562 MLS
WATERFRONT & SUNSHINE! A rare opportunity with 50 feet of dockage--this waterfront mobile home is your perfect entry into the laid-back Keys lifestyle. Whether you're dreaming of a full-time coastal escape or a tropical vacation retreat, this charming home offers the ideal blend of comfort, convenience, and coastal charm. Located in a gated condominium community known for its relaxed atmosphere, residents enjoy two pools, laundry facilities, and a marina, making it an excellent lock-and-leave option for part-time or seasonal living. Inside, the home is nicely maintained with white kitchen cabinetry and a step-down family room that frames lovely views of the canal and marina. From the kitchen and family room, you can watch boats launching from the ramp across the water--an ever-changing backdrop of classic Keys boating activity. Sliding doors open to the outdoors where you'll savor those famous island breezes. A covered carport and a shaded outdoor sitting area make everyday living effortless--and ideal for unwinding during Happy Hour. Seaside Resort is known for its friendly vibe and resort-style amenities, all while being just a short drive to Key West. Here, you get the best of both worlds: island energy when you want it, and peaceful privacy when you don't. You own the land--a valuable advantage in the Keys. Please note: This is a no-pet community.

55 Boca Chica Rd Unit 132, Big Coppitt

30 Orange Dr, Key Largo
$484,900
1 Beds ⋅ 1 Baths ⋅ 620797 MLS
Adorable and Affordable! Turn-Key Conch House! Newly remodeled bath and kitchen with granite counter-tops, newer appliances and easy-slide cabinets. 1B/1B with bonus room perfect for overnight guests or office. Solidly built bungalow located in the x-flood zone (highest elevation in the Keys). Impact windows, 2020 roof, 2023 A/C unit and brand-new tankless water heater. Also includes an amazing hot tub. Furniture is negotiable. Ample on-site parking and storage shed. Includes a 2022 Wildwood camper behind private gates. Best sunset views close by. Voluntary Homeowners Park with private boat ramp, sandy beach and picnic pavilion. Welcome to island living! Just bring your toothbrush and bathing suit and let your Keys lifestyle begin!

30 Orange Dr, Key Largo

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