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$1,949,000
2 Beds ⋅ 3 Baths ⋅ 616791 MLS
Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Positioned on open Gulf waters, the Suites private rooftop sundeck provides a front-row seat to Key West's spectacular sunsets. Throughout both units, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. This property presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

3841 N Roosevelt Blvd Unit 332, Key West
$615,000
1 Beds ⋅ 1 Baths ⋅ 618286 MLS
Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath residence located in the desirable 'A' building at Key West by the Sea. This bright and airy condo designed to capture natural light and showcase the stunning beach and ocean scenery. The unit was upgraded through the 2018 Airport Noise Improvement Project and includes hurricane-impact, sound-insulated windows and doors, providing exceptional tranquility throughout the home. Energy-efficient ductless mini-split A/C systems in both the living area and bedroom offer customized comfort year-round. Situated directly across the street from iconic Smathers Beach, this location is ideal for beach lovers and outdoor enthusiasts alike. Enjoy swimming, sunbathing, and watersports, or take advantage of the wide, paved beachfront promenadeâ€'perfect for biking, jogging, skating, or leisurely sunset strolls. The gated Key West by the Sea community offers resort-style amenities including two swimming pools, two tennis courts, a clubhouse, four conveniently located laundry rooms, bike racks, a car-wash station, and a pet walking area. The community is pet-friendly and well maintained, with condo fees covering building insurance, cable TV, security, pest control, and full grounds and building maintenance. After the first year of ownership, the unit may be rented with a minimum two-month term, adding flexibility and investment potential. Whether you're searching for a serene island retreat, a full-time residence, or a smart coastal investment, this oceanview condo delivers the best of Key West livingâ€'location, views, and lifestyleâ€'all in one exceptional package.

2601 S Roosevelt Blvd Unit 204A, Key West
$798,000
2 Beds ⋅ 1 Baths ⋅ 608965 MLS
Tare Down You can build your dream house to your specifications just 4 houses to the beach. Close to the White Street pier. Walk to pickle ball and tennis courts. Higgs beach is just 3 minutes away. Ride your bikes to Duval Street only 1.3 mile away. This large corner lot is perfectly located. Even the birds know when to fly South.

1521 Rose St, Key West
$2,199,000
6 Beds ⋅ 5 Baths ⋅ 617882 MLS
This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2 bath, open-concept living area & updated kitchen w/ quartz countertops, wine cooler, & pantry overlooking the pool. The master suite has a built-in office, a custom walk-in closet system, & updated bath w/walk in shower. Main Level - Guest Suite is freshly painted w/private entrance, full kitchen, dedicated laundry, & full bathroom. Upper Level -3 beds & 2 baths, w/d, private entrance, French doors & balconies overlook the backyard foliage & pool. The 2nd remodeled bathroom services the 2 bedrooms, 1 of which is used as a media room. The open Living room/Kitchen has built-in wall shelves, The secluded backyard features a heated/chilled saltwater pool w/custom water feature by renowned master potter Jay Gogin. The grounds are secured by unique bamboo fencing and include a refreshing outdoor shower. Whole-house Generac generator and a large Rheem on-demand gas tankless water heater. Front of the house features an elevated patio overlooking the street. metal roof, accordion/panel storm shutters, & 2 driveways as well as 3 off-street parking . Need 24 hour notice to show!

1609 United St, Key West
$599,000
2 Beds ⋅ 2 Baths ⋅ 618834 MLS
Welcome to your private slice of paradise at 3675 Seaside Drive, Unit 342. This highly sought-after end unit offers exceptional privacy, abundant natural light, and a tranquil coastal setting. The bright, open-concept floor plan is designed for effortless island living, with a spacious living and dining area that flows seamlessly from the well-appointed kitchen. The split-bedroom layout provides comfortable retreats, while generous storage enhances everyday convenience. Step onto your private balcony to enjoy refreshing ocean breezes and peek-a-boo ocean views overlooking the peaceful Salt Ponds Preserve - a protected area ensuring your natural backdrop will remain unobstructed for years to come. Beautifully maintained grounds, a recently renovated resort-style pool and heated spa, fitness center, tennis courts, and gated entry create an exceptional lifestyle in one of Key West's most desirable communities. With conventional financing now available, buyers have increased lending flexibility. Furnishings are negotiable, making this move-in-ready residence an outstanding opportunity to own your piece of paradise.

3675 Seaside Dr Unit 342, Key West
$329,000
1 Beds ⋅ 599086 MLS
Office Condo for Sale, centrally located in New Town on the 3rd floor of the Kennedy Center. This Professional Building caters to a diversity of innovative businesses and entrepreneurs in a friendly business environment. Unit 303 is approximately 1475sq.ft. with 6 private offices, large conference room, oversized waiting room/ workspace, and kitchenette. This building offers adequate off-street parking, elevators, and public restrooms on each floor. Included in the monthly Assoc Dues: water, electric, building maint, building insurance.

1010 Kennedy Dr Unit 303, Key West
$349,000
1 Baths ⋅ 599087 MLS
Office Condo for Sale, centrally located in New Town on the 3rd floor of the Kennedy Center. This Professional Building caters to a diversity of innovative businesses and entrepreneurs in a friendly business environment. Unit 307/305B is approximately 2058sq.ft. with 2 entrances, open floor plan with many workspace options, kitchenette, full bathroom, waiting area, private balcony. This building offers adequate off-street parking, elevators, and public restrooms on each floor. Included in the monthly Assoc Dues: water, electric, building maint, building insurance.

1010 Kennedy Dr Unit 307, Key West
$3,599,000
4 Beds ⋅ 5 Baths ⋅ 618829 MLS
1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymond Jungles, this striking 2,810sf residence sits on an expansive 8,800sf lot and captures the essence of tropical modernism. Clean lines. Soaring ceilings. Walls of glass. A seamless and intentional dialogue between indoors and out. This is true Mid Century Modern, authentically executed. A single story design with 4 bedrooms and 4.5 baths, wrapped in glass and stone, where skylights, pocket doors, and oversized windows flood the interiors with natural light. Every room frames the landscape, transforming the gardens into living artwork. Designed for both refined entertaining & comfortable family living, the home features stone floors throughout and a modern floor plan with garden views in every direction. Natural light fills the interiors, blurring the boundary between architecture and nature and creating a seamless indoor outdoor lifestyle that defines island living. At the heart of the home, a newly renovated showpiece kitchen elevates everyday life and gatherings alike, featuring dramatic Cambria quartz countertops with a waterfall island, warm wood cabinetry, pendant lighting, and stainless steel appliances. A full wall opens directly to the 55 foot heated and chilled saltwater pool and stone terrace, creating effortless flow for events large or intimate. The primary suite offers privacy and tranquil garden views, while all four bedrooms provide generous proportions and high ceilings. Oversized glass highlights the extraordinary tropical landscaping surrounding the home. The grounds showcase native and exotic flora from around the world, tropical atriums, a water garden with koi, multiple water features, an outdoor shower, and exceptional privacy inside & out. Properties of this caliber and architectural significance rarely become available, so don't wait, schedule your private showing today!

1501 Georgia St, Key West
$599,000
1 Baths ⋅ 616574 MLS
*****Investors!!!!!****** Eight (8%) Cap Rate. Fully Leased Office Condo to a very strong tenant with very little overhead. This is the easy investment you are looking for. 3 private offices with a large conference room, nice lobby and kitchen area. Great professional building with a wonderful mix of owners and tenants. Professionally managed building. Great location with amazing signage on North Roosevelt Blvd, one of the busiest streets in all of Key West. There is also an ocean view, so you can remember where you are! Please do not go to unit without listing agent, must make an appointment to show. Call today! All owners are Florida Licensed Real Estate Brokers and listings agent is also an owner of this office/condo.

3718 N Roosevelt Blvd, Key West
$1,375,000
4 Beds ⋅ 4 Baths ⋅ 617821 MLS
Ocean Views! Over 2730 interior sq ft townhome with Ocean Views! This is the largest floor plan at SeaSide Court. Boasting 6 balconies - 4 bed - 4 bath - 3 levels over private garage. Only one other of these largest floor plans has come up for sell in the MLS in three years! Concrete construction with impact rated windows & doors gives you lock it & leave convenience. Features stainless steel kitchen appliances, two garden tubs & four showers. For your convenience it has trash and laundry chutes on multiple floors plus parking for three cars (one inside private garage, one in exclusive space outside the garage and one is in open parking around the pool). No attached unit on one side of this town home. On the ground level you have garage, interior storage, laundry room and covered area leading out to a secluded (fenced) courtyard. This is a great space for entertaining, dinning, bar area, etc... to enjoy our mild winter weather. Some owners in this community have built small, private pools in their court yards (this one does NOT have a private pool). Up on the roof you'll find a small, private roof top deck for enjoying sunrises, sunsets, star gazing or working on your tan! The SeaSide complex is gated, has two pools and a club house with weight / work out room. The private elevator goes from the ground level up to all three levels & has just been serviced. The roof-top deck is accessible from a 'ships ladder' only. Proof of funds or mortgage pre-qual required before showing and must accompany all offers. HOA fees cover wind insurance but not flood. See documents tab for Assoc docs, budget, etc...

43 Seaside South Ct, Key West
$2,000,000
8 Beds ⋅ 4 Baths ⋅ 610098 MLS
Development Opportunity. (4) townhouse unit complex situated on a heavily landscaped 10,000 sq ft parcel. Comprised of (2) side by side duplexes legally subdivided as ( 4 ) individual, 750 sq ft licensed units, with (4) separate legal descriptions, parcel numbers, insurance policies, & utilities meters. At one time, there were four individual loans on each of the units as well. **** The only common area is the roof over each duplex, the shared wall between the units and walkways between, and on either side of each of the (2) duplexes. **** Each unit has its own laundry room addition directly off the kitchens with separate exterior screen doors - - (4) pairs of new washers & dryers. Current below market rents for each 2 bedroom, 1 bathroom unit runs between $2,225 to $2,900 with the lower rents soon to be increased. ***** Always operated as a successful rental property, the units were never sold off, which is definitely the Highest and Best use of the complex. Added value would be to install a lap pool/ patio area in the 100' wide back yard as a common use amenity. 2nd option - would be to provide a private pool area for each of the rear (2) units, giving each one half of the large rear yard, greatly increasing their sale value. Mature landscaping that has been well maintained surrounds the property and separates the units. Other valuable amenities are the over sized covered front porches with high open beamed ceilings offering additional square footage - and - valuable on site parking for 10 cars. The property has been continually well maintained - painted, new air conditioners, blinds & curtain rods on all windows. All roof screws were replaced & new ones added to code standards. ***** Under ''Documents Tab'', see the survey with legal descriptions for each unit, floor & site plan & aerial photo. (4) Windstorm, Flood, Fire & Liability policies in place. Call for additional information. Realtor owned.

2322-2324 Seidenberg Ave, 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
$799,000
3 Beds ⋅ 2 Baths ⋅ 618386 MLS
Enjoy relaxed island living in this spacious 3-bedroom, 2-bath condo located in the gated community of Key West by the Sea, directly across from Smathers Beach. This bright and comfortable residence offers an open living and dining area, a private balcony with tropical surroundings, and a thoughtful layout ideal for everyday living or hosting guests. Residents enjoy resort-style amenities including two swimming pools, tennis courts, a clubhouse, and beautifully landscaped grounds. Conveniently located near beaches, shopping, dining, and all the attractions of Old Town Key West, this condo is perfect as a primary residence, second home, or island getaway.

2601 S Roosevelt Blvd Unit 304C, Key West
$1,950,000
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