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3312 Northside Dr Unit 605, Key West
$350,000
1 Beds ⋅ 1 Baths ⋅ 621897 MLS
Move-In Ready Island Living with Ocean Views at The Santa Clara Condominium in Key West! Discover your own slice of paradise at The Santa Clara Condominium in this beautifully renovated and furnished 1-bedroom, 1-bath residence, ideally situated on the 6th floor with stunning ocean views from your private balcony! Thoughtfully updated and tastefully furnished, this inviting residence features a beautifully renovated kitchen with stainless steel appliances, tile and laminate flooring, hurricane-resistant windows and doors, and a comfortable, functional layout. Step outside onto your private ocean-view balcony, where you can sip your morning coffee, unwind with your favorite evening beverage, and enjoy the refreshing island breezes. Embrace the best of resort-style living with an impressive array of community amenities, including a swimming pool, tennis court, secure building entry, on-site laundry facilities, plenty of parking, and well-maintained common areas. Extensive renovations were recently completed, and continued improvements enhance the community's appeal. Location, location, location! Nestled in the heart of Key West's desirable New Town neighborhood, The Santa Clara Condominium offers convenient access to fantastic restaurants, shopping, movie theater, sports complexes, beaches, medical facilities, schools, and the airport, and so much more. All the excitement of historic downtown Key West is just a short drive away. Whether you're a first-time homebuyer, savvy investor, seasonal resident, or simply searching for the perfect island getaway, this turnkey condo offers an exceptional combination of comfort, convenience, and tropical charm. Move right in, relax, and start enjoying the Key West lifestyle you've been dreaming of! Opportunities like this don't come along every day. Schedule your private showing today!

3312 Northside Dr Unit 605, Key West
18 Hilton Haven Road, Key West
$5,195,000
5 Beds ⋅ 6 Baths ⋅ 621709 MLS
Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75' by 300' bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living room's custom hand built beamed wood cathedral ceiling and a majestic staircase. The sunroom features French doors that open to views of the pool and harbor. The expansive backyard includes a covered dining area, a 45' waterfront deck overlooking the dock and boat lift. The chef's kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to a rear private deck and dock. Completing the first floor is the laundry room, half-bath, full bath, and a charming guest bedroom. The sunroom with wet bar and bathroom provides access to the one car garage, and second staircase leading to the second floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. The property must be seen to truly appreciate it. https://show.tours/v/2qnvjWF

18 Hilton Haven Road, Key West
5607 College Rd Unit # B302, Key West
$1,375,000
2 Beds ⋅ 2 Baths ⋅ 621674 MLS
Experience waterfront living at its finest in this rare top-floor residence at Sunset Marina. Boasting breathtaking, unobstructed open-water views and spectacular year-round sunsets, this 2-bedroom, 2-bathroom condominium offers 1,171 square feet of thoughtfully designed living space. The spacious layout provides the perfect balance of comfort and functionality, featuring a generous living area, dedicated dining space, and well-appointed kitchen, along with two bedrooms ideal for accommodating family and guests. Boating enthusiasts will appreciate the full-service marina located just steps below, offering convenient access to everything needed for a day on the water. With direct access to the Gulf and a short boat ride to the Atlantic Ocean, this property is truly a boater's paradise. Sunset Marina is a gated, resort-style community offering a swimming pool, spa, and clubhouse. Additional conveniences include one covered parking space and private storage in the garage. Located just minutes from the heart of Key West and directly across from the island's only golf course, this exceptional residence combines waterfront tranquility with easy access to world-class dining, entertainment, and recreation. Whether you're searching for a full-time residence or an island getaway, this is a rare opportunity to enjoy the very best of the Key West lifestyle.

5607 College Rd Unit # B302, Key West
5607 College Rd Unit C103, Key West
$1,350,000
2 Beds ⋅ 2 Baths ⋅ 621605 MLS
Discover a rare resort-style waterfront lifestyle in Key West--an offering seldom found elsewhere on the island. At Sunset Marina, tranquil marina views, spectacular sunset views, tropical surroundings and exceptional deep water boating access come together just minutes from Key West's dining, entertainment and nearby 18-hole golf course. This move-in-ready, two-bedroom, two-bath condominium features an open-concept layout with volume ceilings, updated flooring, a water filtration system and an updated chef's kitchen with premium appliances. Overlooking the picturesque marina, the private balcony takes center stage of the living area and features electric screens for comfortable outdoor living, with access from both the main living area and the spacious primary suite. Enjoy morning coffee, waterfront breezes and relaxed evenings taking in the everchanging sunsets in your own coastal sanctuary. Set within manicured tropical grounds, Sunset Marina offers a private entrance, scenic waterfront boardwalk, heated pool, hot tub and clubhouse with a kitchen. This distinctive combination of waterfront amenities, boating convenience and resort-style surroundings presents a rare opportunity to experience Key West at a more relaxed pace. Ideal for low maintenance fly in and boat out. Lock and leave! Convenient access to the elevator and stairs, assigned covered parking and enclosed storage add everyday ease, while shared areas accommodate kayaks, bicycles and scooters. The full-service marina features a modern concrete floating dock system and direct open-water access, providing an exceptional gateway to the waters of the Florida Keys. Boat slips may be purchased separately, subject to availability. Ready for immediate occupancy, this waterfront residence invites you to settle in and begin enjoying the Key West lifestyle.

5607 College Rd Unit C103, Key West
5 Mccoy Cir Unit # 5, Key West
$1,299,000
2 Beds ⋅ 3 Baths ⋅ 621523 MLS
BOAT SLIP INCLUDED WITH OWNERSHIP! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the coastal lifestyle you've been looking for: a townhome-style residence with a deeded boat slip, unobstructed open water views, ample parking, and direct sightlines to your boat from the balcony. This 1,387 sq. ft. home features a thoughtfully designed three-level layout with generous storage, covered parking, and multiple outdoor living spaces. The main level offers an open kitchen and living area, convenient half bath, and a spacious balcony overlooking the water, your boat slip, and the open horizon beyond. Upstairs, two bedrooms each feature their own ensuite bathroom, offering comfort and privacy. Below, the covered garage provides ample room for boating gear, fishing equipment, bikes, tools, and everything needed for a day on the water. A private patio adds another outdoor space to relax or prepare for your next adventure. The deeded boat slip is a true highlight, comfortably accommodating a 25-foot boat with dual engines. Walk directly to your boat and enjoy effortless access to the water whenever adventure calls! With dedicated parking, abundant storage, breathtaking water views, and HOA coverage that includes insurance and exterior maintenance, this property combines convenience with the ultimate Key West waterfront lifestyle. An added benefit: Flagler's Landing is not subject to Florida's milestone inspection or Structural Integrity Reserve Study (SIRS) requirements. Come see it by land or by boat! Pull up to the slip and we'll give you a tour!

5 Mccoy Cir Unit # 5, Key West
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
32 Hilton Haven Rd Unit APT 5, Key West
$995,000
2 Beds ⋅ 2 Baths ⋅ 620697 MLS
Embrace the laid-back lifestyle of the Florida Keys in this waterfront two-bedroom, two-bathroom condominium with beautiful water views. Soaring vaulted wood-beamed ceilings, a skylight, and expansive sliding glass doors fill the home with natural light while showcasing the sparkling water beyond. The open-concept living and dining areas flow seamlessly to a spacious wraparound balcony, creating the perfect setting to enjoy your morning coffee, entertain guests, or unwind with the island breeze. The functional kitchen opens to the main living area, making entertaining effortless. Located in Bay Villas, a boutique waterfront community of just nine residences, residents enjoy beautifully maintained grounds, a community pool, and inviting waterfront gathering spaces. Whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity, this waterfront retreat offers the relaxed charm that makes the Florida Keys so special.

32 Hilton Haven Rd Unit APT 5, Key West
901 Eisenhower Dr, Key West
$4,750,000
6 Beds ⋅ 5 Baths ⋅ 620662 MLS
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West
901 Eisenhower Dr, Key West
$4,750,000
7 Beds ⋅ 5 Baths ⋅ 620661 MLS
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West
3312 N Northside Dr Unit 607, Key West
$385,000
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
9 Mccoy Cir Unit 9, Key West
$1,249,000
2 Beds ⋅ 2 Baths ⋅ 620045 MLS
Sweeping Gulf views. Private deeded boat dockage. Effortless Key West elegance. Situated in the coveted enclave of Flagler's Landing, this elevated waterfront residence captures breathtaking open-water views from virtually every room--offering a front-row seat to world-famous Key West sunsets. Spanning ~1,387 sq. ft. of light-filled living space, the home is thoughtfully designed for effortless entertaining. The main level features an open-concept layout anchored by a gourmet kitchen, complete with a custom coral stone island (seating for six), custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a brand-new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony create seamless indoor-outdoor flow for evening breezes and sunset entertaining. A half bath completes the main level. A spiral staircase leads to the upper level, where a built-in bookshelf hall opens to a front-facing balcony. Both serene bedrooms feature walk-in closets and expansive water views. The primary and guest suites share a spacious full bath equipped with a glass walk-in shower, large vanity, and a jacuzzi-style tub. Outside and below, additional amenities include ground-level covered parking, dedicated storage, a laundry area, and a private ground-floor brick patio. For boating enthusiasts, the home includes a deeded shallow-draft slip suitable for a ~24 ft. boat, along with access to a community heated concrete pool. Situated moments from beaches, dining, shopping, and marinas, this home presents a rare opportunity to own a luxury retreat in an exclusive Key West community.

9 Mccoy Cir Unit 9, Key West
Rat, Key West
$850,000
2 Baths ⋅ 619620 MLS
FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West
3312 Northside Dr Unit 405, Key West
$343,400
1 Beds ⋅ 1 Baths ⋅ 616493 MLS
IMPORTANT UPDATE TO NOTE: SELLER IS OFFERING A $5,000 BUYER CREDIT THAT CAN BE USED FOR CLOSING COSTS OR TO PREPAY CONDO FEES!! Excellent as an investment, primary residence, second home, or rental property. This condo is conveniently located in a shopping area with easy access to Duval and US 1. It is one of the few gated communities in Key West with secure entry. You have ample parking, storage, pool, tennis court, laundry, on site management, etc. The unit has newer flooring, newer AC unit, updated electrical panel, updated kitchen, newer appliances, even impact rated hurricane windows & doors. Don't miss this opportunity.

3312 Northside Dr Unit 405, Key West
3424 N Roosevelt Blvd, Key West
$5,200,000
3 Baths ⋅ 617330 MLS
Prime Commercial Property in Iconic Key West - High Visibility & Versatility! This property offers a rare opportunity to own a substantial commercial footprint in one of Florida's most iconic destinations. Whether you're expanding a brand, launching a new concept, or investing in Key West's vibrant market, 3424 N Roosevelt Blvd is a strategic asset with flexible potential. Location Highlights include: • Strategic Location - Located on Key West's main commercial corridor • Proximity - 7 minutes (2.5 miles) to Key West International Airport • Exceptional Visibility - High traffic exposure from both locals and tourists • Surrounded by Amenities -Including hotels, restaurants, banks, shops, fitness centers, and grocery stores. Property Details • Building Square Footage: 3,420 sq ft • Building w/ Tiki: 7,491 sq ft • Lot Square Footage: 36,002 sq ft • Frontage: 155 feet Current Use • Vehicle - Rentals Currently operates as a successful vehicle rental business. • Service Department - Features a care center with six service bays. Business Opportunity sold separately, inquire with agent.

3424 N Roosevelt Blvd, Key West
2613 Gulfview Dr, Key West
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 618065 MLS
Rare WATERFRONT home on the island of Key West, an incredible value priced well below the last comparable sale. Tucked behind the gates of the exclusive Gulf View Pointe community, a rare opportunity awaits to own a waterfront townhome in Key West. This three-bedroom, three-full-bath residence offers the luxury of a private pool and includes a dedicated carport. As you step through the front door, you are welcomed into a bright, open home filled with natural light. The spacious kitchen flows seamlessly into the dining and living areas, all offering beautiful water views overlooking the backyard. The first floor also features a bedroom--currently used as a workshop--and a full bathroom. Upstairs, you'll find two bedrooms, each with its own ensuite bath and private deck. The primary suite's deck offers stunning water views. Outdoor living is a highlight of this property. The backyard features a large covered deck leading to the pool, all positioned westward to capture afternoon sun and spectacular sunset views. Plans and permits for your own private dock are already underway. Ideally located, this home offers convenient proximity to local stores and restaurants and is just a bike ride away from everything downtown Key West has to offer. Whether relaxing poolside, enjoying sunset views, or heading out to explore the island lifestyle, every day is framed by comfort, convenience, and the natural beauty of the Gulf.

2613 Gulfview Dr, Key West
1010 Kennedy Dr Unit 400, Key West
$237,700
599771 MLS
Unique opportunity to own a office condo located on the 4th floor of the Kennedy Center. Unit 400 approximately 2337sq.ft., with an oversized top floor terrace overlooking Key West's New Town area & canopy, shared with unit 402. Unit 400 is Bank Owned and is divided into 5 private offices w/ large bull-pen area, reception, storage, and kitchenette. Shared restroom facilities on each floor, also included in monthly condo dues: water, electric, bldg. maint. & insurance.

1010 Kennedy Dr Unit 400, Key West
3424 N Roosevelt Blvd, Key West
$1,500,000
3 Baths ⋅ 617342 MLS
Key West Jeep Adventures - Turnkey Tourism Business in Paradise Business Overview: Key West Jeep Adventures is a thriving, turn-key adventure rental company located in the heart of Florida's most iconic island destination. Specializing in premium Jeep Wrangler rentals, this business offers tourists the ultimate way to explore the Florida Keys in style and comfort. With a strong brand presence, high customer satisfaction, and a fleet of well-maintained, island-ready vehicles, this is a rare opportunity to own a profitable lifestyle business in paradise. Highlights: • Diverse Fleet: A mix of 2-door and 4-door Jeep Wranglers, many with convertible tops and custom island-themed wraps. • Prime Location: Centrally located in Key West with high visibility and easy access for tourists arriving by plane, cruise, or car. • Established Brand: Strong online presence, 5-star reviews, and a loyal customer base. • Proven Profitability: Consistent year-over-year revenue growth with scalable operations. • Turnkey Operation: Includes all vehicles, booking systems, website, marketing assets, and trained staff. • Partnership Ready: Relationships with local hotels, resorts, and travel agencies already in place. Growth Potential: Opportunities abound to expand services into guided tours, mapped excursions, or additional rental offerings such as scooters, e-bikes, or paddleboards. With Key West's year-round tourism and growing demand for experiential travel, the sky's the limit. Ideal Buyer: Perfect for an entrepreneur seeking a lifestyle business, an investor looking for a high-margin tourism asset, or a strategic buyer in the travel or adventure rental space. PRICE: $1,950,000 BUSINESS OP, INVENTORY: $2,700,000 SOLD SEPERATLY

3424 N Roosevelt Blvd, Key West
3841 N Roosevelt Blvd Unit 632, Key West
$749,000
2 Beds ⋅ 3 Baths ⋅ 612515 MLS
Experience Ultimate Elegance at Key West's Marriott Beachside Resort. This offering includes two luxurious, fully furnished units—a Signature King Room and a Resort View Suite—each designed to deliver an exceptional blend of comfort and sophistication. Together, they provide flexibility as a full-time residence, vacation retreat, or income-producing rental property with two coveted TRANSIENT RENTAL LICENSES and a strong rental history. The Signature King Room, spanning 283 sq.ft. is an intimate retreat ideal for accommodating up to two guests. It features elegant finishes, high-end furnishings, and stunning attention to detail, making it a perfect haven for relaxation. The Resort View Suite, generously sized at 1074 sq. ft, can comfortably accommodate up to four guests. Its open floor plan includes a designer kitchen with a Subzero refrigerator, KitchenAid stove, GE microwave, range hood, Bosch dishwasher, dual stainless-steel sinks, and garbage disposal, all accented by crown molding and baseboards. The dining area is illuminated with dimmable lighting, creating the perfect ambiance for gatherings. The primary suite is a sanctuary with a sunken jetted tub, tiled shower stall, and dual vanities, while 16-inch tile flooring extends throughout, adding a refined aesthetic. Resort living is elevated with access to a private beach, a heated waterfront pool and spa, and a poolside bar and grill. On-site gourmet dining, valet parking, and concierge services are available to meet your every need, with optional on-site rental management providing a seamless investment opportunity. The secured building includes a garage and assigned parking for convenience and peace of mind. Positioned on open Gulf waters, the property's private sundeck provides panoramic views, offering the perfect backdrop for serene mornings or captivating sunsets. This property is an extraordinary opportunity to embrace the best of Key West living.

3841 N Roosevelt Blvd Unit 632, Key West

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