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$625,000
1 Beds ⋅ 1 Baths ⋅ 620905 MLS
Positioned directly across South Roosevelt Boulevard from Smathers Beach, it blends high-end modern finishes with expansive views of Key West's tranquil salt ponds. Interior highlights and upgrades include Carrara marble surfaces installed in both the kitchen and bathroom a wet bar, tiled floors flowing seamlessly throughout all living spaces, impact-resistant glass windows and doors for ultimate peace of mind. Other feature include large, covered private balcony capturing views of the salt ponds and the surrounding landscape, assigned parking with storage locker, and so much more. Resort-Style community amenities include a spacious, heated saltwater swimming pool, adjacent hot tub, and full-size tennis/pickleball courts, access to the resident clubhouse, dry saunas, and common area lounges. Other conveniences include barbecue area, EV charging station and a car wash. Make La Brisa your home today.

1901 S Roosevelt Blvd Unit 407N, Key West
$599,000
1 Beds ⋅ 1 Baths ⋅ 620722 MLS
Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the privacy and simplicity of low maintenance island living. Inside, this 1 bedroom, 1 bathroom condominium feels bright, comfortable, and welcoming. The open living spaces flow naturally to two private outdoor decks, one at the front of the home that is perfect for enjoying the neighborhood atmosphere and another tucked just off the bedroom, surrounded by mature tropical landscaping for a more private escape. The community itself offers the amenities that make everyday living feel like a vacation, including a beautifully maintained heated swimming pool set among lush tropical grounds. An assigned off street parking space and a spacious locked storage area provide conveniences that are increasingly valuable in Key West. Located just 4 blocks from Duval Street, you can easily walk or bike to beaches, restaurants, galleries, shopping, and everything that makes island life so special, while still returning home to one of the quieter residential pockets of Old Town. Whether you are searching for a full time residence, a seasonal retreat, or simply a place where life naturally slows down, 816 South Street, Unit 4 offers an opportunity to experience the very best of Casa Marina living.

816 S St Unit 4, Key West
$550,000
1 Beds ⋅ 1 Baths ⋅ 620692 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a new metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit 3, Key West
$725,000
1 Beds ⋅ 1 Baths ⋅ 620493 MLS
''Seaport Sanctuary'' Located within the Land's End compound steps away from the Historic Key West Seaport and Harbor Walk. This 1 bedroom 1 bath conch cottage features an open floor plan with a storage loft, cathedral ceilings and hardwood floors. Nestled down a brick pathway across from the residents only heated pool. Professionally maintained landscaping surrounds this 6 freestanding conch home complex. Call today!

308 Margaret St Unit 3, Key West
$819,000
1 Beds ⋅ 1 Baths ⋅ 620379 MLS
This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. In addition, it is being sold completely turnkey! Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Tucked away on a quiet one-way street, this tropical retreat is just a short stroll to Cafe Sole, Little Pearl, Fausto's Food Palace, local bakeries, and charming boutiques. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West
$7,500
1 Beds ⋅ 2 Baths ⋅ 620225 MLS
Rare leasing opportunity in the heart of Old Town Key West. The property offers approximately 1,398 square feet, consisting of 1,078 square feet of ground-floor commercial space plus an additional 320-square-foot loft/workspace area. The space is well suited for a variety of retail, office, gallery, or service-oriented uses. In addition to the interior space, the property features usable front, side, and rear outdoor areas, including a large backyard that may be ideal for outdoor seating, storage, displays, events, or other complementary business uses. Located in a highly desirable Old Town location with excellent visibility and accessibility, this unique property offers flexibility that is difficult to find in the Key West market. Base rent only; NNN expenses not included.

408 Greene St, Key West
$639,000
1 Beds ⋅ 1 Baths ⋅ 620158 MLS
Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenience. Featuring two balconies, you can enjoy your morning coffee or unwind in the evening while soaking up the tropical vibes. The cozy living space is adorned with modern finishes, complemented by a well-equipped kitchen that makes entertaining a breeze. Located just steps from local attractions, exquisite dining, and vibrant nightlife, this apartment is an excellent choice for those seeking the ultimate island lifestyle. Experience your perfect getaway in this Key West gem!

1402 Olivia St Unit 2, Key West
$345,000
1 Beds ⋅ 1 Baths ⋅ 619359 MLS
Experience Key West sunsets and ocean breezes from this TOP-FLOOR unit! This one-bedroom, one-bathroom residence boasts a spacious and practical floor plan with private balcony. Recent enhancements include a NEW HVAC system, NEW electrical panel, NEW impact-resistant windows and doors and kitchen appliances. Situated near shopping centers, cinema, schools & dining, this unit makes an ideal entry-level home or investment property. The building has recently undergone renovations, with all special assessments paid in full. Santa Clara offers gated entry, parking, POOL, tennis courts and onsite management.

3312 Northside Dr Unit APT 712, Key West
$999,000
1 Beds ⋅ 1 Baths ⋅ 619196 MLS
Discover a rare investment opportunity in the heart of Key West. This spacious corner duplex lot at 2330 Staples St and 1428 6th St offers incredible potential with two separate addresses and alley access for three convenient side entrances. The large lot features a charming, spacious cottage complete with a full kitchen, a bedroom with ample closet space, a stylish bathroom, and an attached garage--perfect for comfortable living or rental income. The second unit has been demolished, providing a blank canvas to rebuild your dream home or expand your investment portfolio. Alternatively, you can choose to demolish the existing cottage and build two brand-new units on this generous lot. Mature landscaping surrounds the property, offering privacy and a serene atmosphere. With two separate ROGOs ready to go and the Staples side of the lot free from flooding, you can start building immediately. Don't miss this unique chance to own a versatile property in a prime Key West location with endless possibilities. Whether you're looking to renovate, rebuild, or develop, this property is your gateway to maximizing value and enjoying the vibrant lifestyle of Key West. Act now and make this exceptional property yours!

2330 Staples Ave, Key West
$344,000
1 Beds ⋅ 1 Baths ⋅ 619131 MLS
Charming second-floor 1 bedroom, 1 bath condominium featuring a functional layout with a kitchen that offers modern appeal and a comfortable living space enhanced by tile flooring throughout. Large sliding doors open to a private balcony overlooking the tennis courts. The bathroom has been thoughtfully maintained with updated finishes. Located within the gated community of Santa Clara Condominiums, residents enjoy a variety of amenities including a heated pool, tennis court, laundry facilities on each floor, two elevators, secure building entry, backup generator, on-site management, and dedicated personal and bike storage. Conveniently situated near shopping, dining, and recreational facilities, this property presents a great opportunity as a primary residence, vacation getaway, or investment. No pets permitted. HOA fee includes building insurance, security, pest control, exterior & common area building maintenance.

3312 Northside Dr Unit 205, Key West
$619,000
1 Beds ⋅ 1 Baths ⋅ 618779 MLS
This is a must see unique and airy tropical second story condo in the Southpark Condominium Association. Lush vegetation surrounds the property and the private pool area located in the beautiful Casa Marina neighborhood. This upstairs one Bedroom/ one Bathroom condo offers relaxation on either the front covered porch or the rear private deck with a motorized awning for your comfort and convenience. Inside the condo has hardwood/travertine flooring, Surround Sound stereo, stainless steel appliances, granite counters, brand new AC and washer/dryer inside the unit. Included with the condo is an off street assigned parking space, a large indoor locked storage space and a lovely heated pool area in a peaceful and quiet tropical setting. Location is everything and this property is just a short walk to Duval St (South Beach), Higgs Beach, tennis, pickleball and bocce courts, White Street Pier and some great restaurants (Louie's Backyard, Salute on the Beach, Four Marlins, La Te Da and many more) . This truly is a hidden gem and ready for you to make it your own ''Piece of Paradise''. Call for a private showing!

804 South St Unit APT 3, Key West
$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
$415,000
1 Beds ⋅ 1 Baths ⋅ 614786 MLS
Boutique commercial, ground floor office condo for sale in Old Town at Seafoam Condominiums. Only one of two Commercial units in the building. This 665 sf. office is turnkey and perfect for Professionals looking for a small office to own vs. paying rent every month. Great location and close to everything in Old town either by walking or biking. Exterior has several large pane windows for natural light inside. To enter off the sidewalk there are a set of gorgeous, hand made mahogany french doors. Also, there is an interior side door for private access. Interior has 12' ceilings and the layout includes front seating area with a receptionist window, administrators office and private office in rear. Half bath is ADA compliant. This unit has been totally renovated and ready to move in. Renovations include new Brazilian cherry wood floors & keystone flooring in the bathroom. upgraded electric and lighting, freshly painted, Central AC and wireless Security system. Seafoam building has coded entrance, atrium hallways and large in-ground concrete pool exclusively for Condo owners and guests. HOA fee of $1,286/mos. includes insurances and reserves. Includes Liability, Wind and Flood insurance. Building has never flooded and in X flood zone. Building is up to date with SIRS and milestone inspections. Additional $587/mos. special assessment for windstorm insurance. Same owner since 2008. Owner will consider lease with Option to Purchase. Asking rent is $4,000/mos.

812 Fleming St Unit 2, Key West
$849,000
1 Beds ⋅ 1 Baths ⋅ 618771 MLS
Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by!

817 Pearl St, Key West
$343,500
1 Beds ⋅ 1 Baths ⋅ 616493 MLS
A new price makes this 1 bedroom 1 bath condo the least expensive property for sale in Key West. 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
$799,000
1 Beds ⋅ 2 Baths ⋅ 618838 MLS
Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of BEACHFRONT living at the Key West Beachside Resort and Residences. This stunning Gulf View, Waterfront corner suite invites you to live like you are on vacation every day. This is a rare to come on the market opportunity, as there are only three one-bedroom units on the entire property, and this beachfront location remains the most desired. Inside, designer-grade finishes and furnishings create an atmosphere of refined elegance. Travertine flooring flows throughout the spacious living areas, complemented by an open gourmet kitchen featuring granite countertops, stainless steel appliances, and custom cabinetry. The well-appointed bedroom and two bathrooms provide ample space and privacy, while a sleeper sofa offers additional sleeping accommodations for guests. An oversized balcony provides a private retreat to enjoy the tropical breeze and breathtaking Gulf sunsets. Beyond your door, the resort's world-class amenities await, including a restaurant, bar, pool, spa, and fitness center. The on-site parking garage includes one deeded parking space, and there is a property shuttle for added convenience. This superb property offers incredible flexibility: use it as your private getaway, generate income through the onsite professionally managed rental program with no maximum stay restriction for owners, or both. The property boasts a proven track record of strong rental performance throughout 2025, demonstrating its appeal as a high-performing investment. Don't miss this prime opportunity to own a piece of paradise with lock and leave potential that is perfect for part-time residency and robust passive income. Reach out to learn more about how to make this your 2026 lifestyle.

3841 N Roosevelt Blvd Unit 121, Key West
$1,074,000
1 Beds ⋅ 1 Baths ⋅ 615746 MLS
Fully furnished TRANSIENT LICENSED condos in Coconut Mallory Marina & Resort — listed separately but offered together as a rare investment package. Known as The Poolside Cottages (Units #411 & #412), these charming 1BR/1BA cottages are conveniently located near the pool and feature private patios, vaulted ceilings, updated interiors, and sleeping space for up to six guests per unit. Each unit is turnkey and ready for immediate rental income, with dedicated laundry access and assigned parking included. Coconut Mallory offers two pools, a jacuzzi, lush tropical grounds, a private marina with boat access, and a laid-back Key West vibe guests appreciate. The resort's location provides easy access to Smathers Beach, Duval Street, Old Town, the airport, and local attractions. HOA fee covers electric, water, sewer, garbage, Wi-Fi, cable, exterior insurance, and common area care. A rare chance to own two transient-licensed rentals in one of Key West's hidden gems.

1445 S 1445 Roosevelt Blvd Unit 411, Key West
$625,000
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
$1,074,000
1 Beds ⋅ 1 Baths ⋅ 615748 MLS
Fully furnished TRANSIENT LICENSED condos in Coconut Mallory Marina & Resort — listed separately but offered together as a rare investment package. Known as The Poolside Cottages (Units #412 & #411), these charming 1BR/1BA cottages sit steps from the pool with private patios, vaulted ceilings, updated interiors, and sleeping space for up to six guests per unit. Each comes turnkey and ready for immediate rental income, with dedicated laundry access and assigned parking included. Coconut Mallory offers two pools, a jacuzzi, lush tropical grounds, a private marina with boat access, and a laid-back Key West vibe guests love. Stroll to Smathers Beach or hop on your bike to Duval Street — the location is ideal for visitors wanting both peace and quick access to Old Town, the airport, and island attractions. HOA fee covers electric, water, sewer, garbage, Wi-Fi, cable, exterior insurance, and common area care. A rare chance to own two transient-licensed rentals in one of Key West's hidden gems.

1445 S Roosevelt Blvd Unit 412, Key West
$998,000
1 Beds ⋅ 1 Baths ⋅ 618122 MLS
Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive. Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the heart of Key West. Inside, you'll find soaring wood-vaulted ceilings and warm floors features that hint to island's past. The airy loft adds extra space and character, while the private back deck invites unforgettable evenings dining under the stars. Out front, the iconic porch is made for slow evenings, and people-watching ... the classic Key West pastime. Just two blocks from Duval Street, this location is unbeatable, it's close enough to walk to the best restaurants, galleries, and shops, yet tucked away for peace and privacy. Even better, it's in the coveted X-Zone, so no flood insurance is required, and yes, it has its own, coveted off-street parking spot This isn't just a home, it's a private oasis. It's YOUR Key West story waiting to be written.

817 Terry Ln, 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
$1,100,000
1 Beds ⋅ 2 Baths ⋅ 617909 MLS
Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully renovated 1-bedroom, 1.5-bath home, plus sleeping loft and cabana, in the heart of Old Town Key West. Thoughtfully updated with quartz countertops, custom wood cabinetry, and top-of-the-line stainless steel appliances, this home seamlessly blends modern comfort with historic charm. A cozy sleeping loft offers extra space for guests or lounging, while a separate structure on the property can serve as a studio, guest room, or private cabana. Nestled on a generously sized lot in the desirable X flood zone, this home also conveys with a 1/10 interest in a private parking lot behind the residence—a rare Key West perk! Don't miss your chance to own a versatile and stylish island escape in one of Key West's most sought-after neighborhoods.

738 Olivia St, Key West
$2,950,000
1 Beds ⋅ 3 Baths ⋅ 615015 MLS
Completely remodeled from top to bottom, this turnkey restaurant in the heart of Old Town Key West offers a rare opportunity to own a fully updated and licensed 150-seat dining destination. Every inch of the property has been thoughtfully renovated, including brand-new electrical, plumbing, HVAC, flooring, lighting, and fixtures, creating a fresh, modern space that still captures the charm and character of historic Key West. The layout features expansive indoor-outdoor dining areas, a stylish full-service bar, and newly designed restrooms, all tailored for comfort, ambiance, and efficient flow. The commercial-grade kitchen is fully equipped with state-of-the-art appliances, ample prep space, and storage, making it ideal for high-volume service across a wide range of culinary concepts. Adding to its versatility, the property also includes a beautifully updated 1-bedroom, 1-bathroom apartment upstairs—perfect for on-site living, staff housing, or additional rental income.

532 Margaret St, Key West
$820,000
1 Beds ⋅ 1 Baths ⋅ 618001 MLS
Old Town Condo Near Duval: Bright 1-bedroom, 1-bath condo located in the heart of Historic Old Town Key West. Featuring high ceilings and an open floor plan, this residence is filled with natural light. Just steps from Duval Street, dining, shopping, and entertainment. Ideal as a vacation rental, investment property, or personal island retreat.OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

817 Eaton St Unit 1, Key West
$699,000
1 Beds ⋅ 1 Baths ⋅ 618077 MLS
Picture perfect condo located in 1 of 2 historic buildings totaling 8 units with a generous sized shared pool and lounging area. This setup is ideal for 1-2 people looking for a low maintenance island address in a quiet neighborhood walkable to all that Old Town, the Historic Seaport and Duval Street has to offer. This unit welcomes you with 10ft ceilings and Dade County pine walls and floors throughout. Enjoy the charming and peaceful screened in patio that brings the outdoor in just off of the living room. This one bedroom floor plan also enjoys a generous size ensuite bathroom and full size washer and dryer. The petite and efficient kitchen is all you need to complete your island home. If your looking for a slice of the island life to call your own this condo allows you to come and go with the ease of a well run condo association the handles all of the worries on your behalf!

1203 Newton St Unit 1, Key West