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$1,678,000
4 Beds ⋅ 4 Baths ⋅ 619991 MLS
Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown--don't miss it.

2519 Staples Ave, Key West
$2,500,000
8 Beds ⋅ 4 Baths ⋅ 619978 MLS
Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

1409 Whalton St, Key West
$1,170,000
3 Beds ⋅ 3 Baths ⋅ 619952 MLS
Hidden away on one of Old Town's most storied streets, 1016 Varela St. Rear is the kind of Key West address that feels like a private discovery. Originally constructed in the 1920s, this piece of living Key West history has been thoughtfully renovated while honoring the character that only a century of island life can impart. Tucked discreetly behind the street, the fully restored 3-bedroom, 3-bathroom residence offers a rare sense of seclusion in the heart of historic Old Town -- without sacrificing a single step of the legendary walkability that defines this neighborhood. Duval Street, world-class dining, the harbor, and the full tapestry of Key West life are all moments away on foot. Arrive home to a covered front porch -- the quintessential Key West perch for morning coffee or evening cocktails. Inside, soaring cathedral ceilings flood the living spaces with light and volume, while refinished hardwood floors, an updated kitchen, and impact windows throughout speak to a renovation done with care and intention. The private rear yard offers room for a pool, a rare opportunity to create your own tropical retreat in the heart of Old Town. A separate upstairs apartment with its own private entrance offers exceptional flexibility: a sanctuary for a young adult, an elegant in-law suite, or an income-producing rental that helps carry the property. For the discerning buyer, two details stand above the rest: 1016 Varela Rear sits in an X flood zone -- the premier flood designation in the Keys, carrying no flood insurance requirement -- and the property carries an assumable VA loan, a remarkable financial advantage for qualified buyers in today's market. In Old Town Key West, a century-old home with this much flexibility and this little compromise is extraordinarily rare. Welcome to your hidden corner of paradise.

1016 Varela St Unit Rear, Key West
$1,675,000
5 Beds ⋅ 3 Baths ⋅ 619947 MLS
Welcome to 606 Grinnell Street located in the heart of Old Town Key West, this charming duplex offers the perfect blend of classic Key West character and flexible living opportunities. The first-floor unit features 2 nice sized bedrooms and 1.5 baths, while the spacious second-floor unit offers 3 bedrooms and 1 bath, complete with a private rear balcony overlooking the backyard oasis. Both units feature full sized kitchens with great dining spaces, as well as living rooms too. A welcoming front porch adds to the home's island charm, creating the perfect spot to relax and enjoy the neighborhood atmosphere. Step outside to your private backyard retreat featuring a sparkling pool for your relaxation, ideal for entertaining, time off, or enjoying the Key West lifestyle year-round. Whether you're looking for an investment property, multi-generational living, or the option to live in one unit while renting the other, this versatile Old Town property offers endless potential. There's a convenient side door entrance for the 2nd unit upstairs, while having a lockout door in the first unit if you wanted access to upstairs. Nice thought for Indoor or Outdoor Access to upstairs. Just moments from world-famous Duval Street with lots of dining options, historical seaport, shopping, and nightlife experiences.

606 Grinnell St, Key West
$2,345,000
5 Beds ⋅ 4 Baths ⋅ 619927 MLS
FOUR UNIT Property in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

1104 Truman Ave, Key West
$1,799,999
7 Beds ⋅ 5 Baths ⋅ 619911 MLS
Endless possiblities! Three units to rent for the investor or live in one and produce income from the other units. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have two units with a 2/1 floor plan and a fire wall between units. All units have W/D hook ups and central air. Both units upstairs have balconies and seperate staircases for entry. Low maintence yardcare. Covered and dedicated parking with street parking as well. Great location close to downtown and the beaches. Owner is a general contractor and has lived in the home since 1972 and added the second story in 1994.

1504 Flagler Ave, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619904 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
$7,500,000
5 Beds ⋅ 5 Baths ⋅ 619886 MLS
At the end of prestigious Sunrise Lane, where land meets open water on 3 sides, 3750 Sunrise Lane stands as one of the most extraordinary waterfront offerings in Key West. Properties of this scale and setting rarely exist, and almost never come to market. Originally built in the 1950s and extensively rebuilt in 1999, this legacy estate sits on a 28,500sf peninsula, offering a rare scale, privacy, and waterfront presence that is nearly impossible to replicate. The 5,378sf residence blends timeless architecture with expansive indoor and outdoor living. The main level features gracious living spaces with heart pine floors, French doors, and light-filled rooms opening to wide terraces and tranquil water views. The home offers 5 bedrooms and 4.5 baths, including 3 first-floor bedrooms and a spacious primary suite designed for comfort and privacy. Upstairs, 2 guest bedrooms open to a covered balcony and rare widow's walk with panoramic views of the Atlantic, Gulf, and surrounding protected lands. At the heart of the home is an expansive family-style kitchen with a large breakfast room, bar seating, desk area, and rich wood cabinetry. A handsome den with a built-in wet bar creates a warm gathering space, while a studio/flex room offers versatility as an office, art studio, fitness room, or guest overflow. The grounds are equally remarkable, featuring mature tropical landscaping, a large swimming pool, and over 3,200sf of brick patios. Nearly 500 linear feet of seawall provide exceptional dockage with a concrete dock and 2 boat lifts offering immediate deep-water access to both the Atlantic and Gulf. An oversized finished 828sf garage with 4 garage doors adds rare flexibility and functionality. This legacy estate awaits restoration and the vision of its next owner. Its setting, structure, and scale create a once-in-a-generation opportunity to reimagine one of Key West's most significant waterfront properties.

3750 Sunrise Ln, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619758 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 619738 MLS
FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with generous cabinet space.. A fully enclosed porch is your place for morning coffee, chatting around the table or dining while overlooking the pool. Central air conditioning keeps things cool. Every window and door has been upgraded to impact, giving you peace of mind alongside the charm. Step outside and the magic continues. A sparkling pool with a waterfall feature and Trex decking invites you to linger. An outdoor shower makes coming in from the water effortless. The fully fenced front and back yards create a private tropical sanctuary, and off-street parking -- a true luxury in Old Town -- takes the stress out of coming home. The guest cottage is its own retreat, offering one bedroom, one bath, and a Murphy bed that makes the space as flexible as your plans. Whether it becomes a private getaway for family and friends, a creative studio or a detached office, it gives this property a versatility that is genuinely rare. The location is the final piece that makes everything click. A ten-minute walk from Duval Street -live music, art galleries, open-air restaurants, theaters and the electric pulse that makes Key West unlike anywhere else on earth. 7 minutes the other way brings you to the White Street District know for Fausto's Food Palace, where locals have shopped for generations, and the legendary Sandy's Café. This property comes fully turn-key, bedding, housewares, pool toys, bicycles, and yes, flip flops are included. Whether you wanting a second home, a monthly vacation rental or simply ready to walk through the door and start living living in paradise.

928 United St, Key West
$9,888,000
3 Beds ⋅ 2 Baths ⋅ 619724 MLS
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

1430 Vernon Ave, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619723 MLS
DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 619715 MLS
Seclusion meets striking contemporary design in this elevated sanctuary, positioned just moments from Higgs Beach and White Street Pier. Behind a signature pivoting red gate and architectural peekaboo wall, the residence unfolds as a curated experience of light and geometry. The entry foyer--anchored by a sun-drenched desk nook and an open-tread staircase--leads to a living space defined by floor-to-ceiling glass and transom detailing that frames the outdoor oasis like a living gallery. The culinary space is anchored by a sleek, minimalist aesthetic, featuring custom cabinetry, crisp white surfaces, and Bosch appliances. A glass-door pantry provides a sophisticated home for provisions, blending functional utility with the kitchen's clean geometry For guests, a private main-level suite is tucked away behind a discreet pocket door, offering an ensuite bathroom and ample closet space for a completely independent wing. The second floor is dedicated entirely to the primary retreat. This suite features a large walk-in closet and a refined ensuite bathroom. Just beyond the sleeping quarters is a private balcony where an open-air soaking tub offers a quiet moment of luxury under the stars. The exterior of the home is a masterwork of tropical landscaping, where beautifully mature and lush greenery wraps the property in total privacy. At the heart of the grounds is an expansive heated pool bordered by a large deck, perfect for sun-drenched afternoons. For the host, the covered outdoor dining pavilion is fully equipped with an integrated grill and ample countertop space for seamless entertaining. Nearby, a serene Zen garden with a tranquil fountain feature provides a quiet corner for meditation and reflection. This is more than a home; it is a sophisticated, high-design haven just steps from the ocean.

1701 Laird St, Key West
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 619703 MLS
Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

1224 2nd St, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619700 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619698 MLS
Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
$2,590,000
3 Beds ⋅ 2 Baths ⋅ 619667 MLS
Welcome to your Key West waterfront retreat. This 3bedroom 2bath home is featuring key upgrades already in place with a new roof, all new windows, updated electrical, fresh paint, and a beautiful brand new pool. Situated on an oversized 9,794 sq ft lot with room for your boat this home offers the ideal blend of comfort, outdoor living, and the flexibility to personalize over time. A rare opportunity to step into waterfront living in one of Key West's most desirable locations.

3612 Sunrise Dr, Key West
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 619665 MLS
Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in closet, providing privacy and convenience for family and guests alike. The main level is designed for living and entertaining, large open floor plan. An additional bedroom and bath on main floor with a door to the pool/deck area. The chef's kitchen is a standout, equipped with high-end stainless steel appliances including a 48-inch Viking gas range, refrigerator, ice maker, dishwasher, built-in steamer, wine cooler, and rich cherry cabinetry. Additional highlights include: Efficient 2-zone HVAC system, Impact windows and sliding glass doors, Beautiful Tigerwood flooring throughout. The exterior is equally impressive, featuring durable Hardi plank siding for low maintenance, Ipe wood decking, and a private pool surrounded by lush tropical landscaping. The fully fenced yard creates a serene and secluded outdoor retreat. The house also offers two off-street parking spaces, plus ample street parking for guests. A rare opportunity to own a spacious, well-appointed home in a prime location--this one truly has it all.

1320 South Street, Key West
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 619646 MLS
1421 Reynolds is a beautifully renovated mid century modern home located 3 blocks from Higgs Beach, one of Key West's best beaches and the perfect spot to watch the sunset. You will see the ocean from your driveway. You can walk or bike to Duval street, but live just far enough away to enjoy peace and tranquility. The spacious floor plan offers 4 bedrooms and 3 bathrooms. Vaulted ceilings throughout give it a sense of open space and the sliding glass doors in the great room open all the way for indoor outdoor living. All impact doors and windows allow lots of natural light to flood into the modern renovation in every room. Off street parking and room for a pool make this a rare opportunity in one of Key West's most coveted neighborhoods, the Casa Marina. In the front you will find a private zen garden adding outdoor space to the master bedroom. The kitchen has all stainless appliances with Viking, Samsung smart fridge and JennAir. This home was designed to enjoy the best Key West has to offer, from the interior to the outdoor space to the neighborhood itself. You will find yourself swimming in the ocean for sunset, walking to the Casa Marina Hotel for drinks overlooking the ocean, and having dinner on the beach at Salute's or Louie's Backyard. Owner/listing agent is a licensed FL Real Estate Broker.

1421 Reynolds St, Key West
$2,380,000
3 Beds ⋅ 2 Baths ⋅ 619644 MLS
Experience the ultimate Key West waterfront lifestyle with this private tropical retreat on the highly coveted Riviera Canal--one of the island's only canals offering direct boating access to world-class fishing and diving. Tucked behind a gated entrance, this beautifully landscaped property welcomes you into a lush, secluded garden setting that feels like your own hidden oasis in the heart of Key West. This meticulously maintained 3-bedroom, 2-bath ground-level pool home blends comfort, style, and functionality. Inside, you'll find elegant travertine flooring throughout, granite countertops, stainless steel appliances, and a wet bar--perfect for entertaining. The thoughtfully designed layout features two separate living areas, with both the main living space and the primary suite opening through hurricane-impact sliding glass doors to the backyard. Step outside to your private resort-style escape, where a stunning in-ground concrete pool overlooks the tranquil canal. Enjoy peaceful water views, frequent visits from manatees, and the natural privacy provided by protected mangroves across the water. The screened, covered lanai creates the perfect setting for outdoor dining and relaxation year-round. Boaters will appreciate the 15,000 lb boat lift, allowing you to go from home to open water in minutes. Additional premium features include a newer generator with large propane tanks, outdoor shower, electric gate, automated irrigation and landscape lighting, covered carport, and secure off-street parking for two vehicles. Located just minutes from Key West International Airport, dining, and local attractions, this exceptional property offers the perfect blend of convenience, privacy, and island luxury. Whether you're seeking a full-time residence or a vacation escape, this waterfront home is a rare opportunity to own a true piece of paradise.

3108 Riviera Dr, Key West
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 619619 MLS
Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

1220 Georgia St, Key West
$999,000
6 Beds ⋅ 2 Baths ⋅ 619618 MLS
Duplex with Solid Income - $91,800/Year This income-producing duplex offers two spacious units, each featuring 3 bedrooms and 1 bathroom--an ideal setup for steady, long-term rental demand. Currently leased at $3,850 and $3,800 per month, the property delivers a strong annual income of $91,800. Situated on a 4,400 sq. ft. lot in a desirable location near the coast, this property is just a short ride from the energy of downtown, making it highly attractive to tenants who want both convenience and lifestyle. Each unit is separately configured, providing flexibility for investors or owner-occupants. The rear unit benefits from off-street parking--a valuable feature in this market. Built with durable Indian Block construction, the property offers long-term structural integrity with room for future value-add opportunities.

1916 Seidenberg Ave, Key West
$1,500,000
9 Beds ⋅ 7 Baths ⋅ 619617 MLS
Right in the heart of Key West, this income-producing triplex is the kind of property investors are always asking for--strong numbers, solid layout, and a location that never goes out of style. The property features three spacious units, each offering 3 bedrooms and 2 bathrooms, making them highly desirable for long-term tenants. The front unit stands out with its single-level design--larger than the others and perfect for tenants who prefer the ease of one-story living. The two rear units are thoughtfully designed as two-story layouts, with living, kitchen, and entertaining space on the main level, and all bedrooms and bathrooms tucked upstairs for privacy. From an investment standpoint, the numbers speak for themselves. The units are currently rented at $6,500, $4,500, and $3,400 per month, bringing in a total annual income of $172,800 on long-term leases--steady, reliable cash flow in one of the most in-demand rental markets in the country. And then there's the location. You're just minutes from the coastline and a quick ride to downtown Key West, where all the restaurants, nightlife, and charm come together. Tenants love it here--which is exactly what you want as an owner. Whether you're looking to expand your portfolio or secure a high-performing asset in the Florida Keys, this triplex checks all the boxes.

1821 Harris Ave, Key West
$1,150,000
2 Beds ⋅ 2 Baths ⋅ 619610 MLS
Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay homage to the home's rich heritage. Recent enhancements have elevated the home's functionality and aesthetic appeal including a new foundation, beautiful new flooring, tastefully updated bathrooms, and fresh paint inside and outside. The home features high ceilings with exposed beams and French doors that open to a private patio. This outdoor space is perfect for morning coffee or evening gatherings under the stars. The second-floor primary suite offers a private sanctuary, complete with a walk-in closet and an en-suite bathroom featuring a classic clawfoot tub. The downstairs bedroom is generously sized and includes a walk-in closet. The private patio, accessible through French doors, is ideal for alfresco dining and relaxation. The front porch offers a quiet spot to enjoy the tranquility of Elgin Lane, a quiet lane that ensures privacy and minimal traffic. A designated off-street parking space adds to the convenience of this property. A private walkway provides direct access to Eaton Street, placing local bakeries, shops, and the vibrant Seaport just steps away. Situated less than a block from the renowned Old Town Bakery and just two blocks from the lively Seaport, this home offers unparalleled access to Key West's finest dining, shopping, and entertainment venues. Whether you're seeking a serene personal retreat or a lucrative investment property, this residence offers an exceptional opportunity to own a piece of Key West's storied history.

1025 Elgin Ln, Key West
$449,000
2 Beds ⋅ 1 Baths ⋅ 619604 MLS
Why buy in a condo complex? This charming renovated 2-bedroom, 1-bath residence offers an exceptional opportunity to own in the heart of Key West without sacrificing privacy or outdoor living. Thoughtfully updated throughout, the home features a modern kitchen with stainless steel appliances, dishwasher, and the convenience of an in-unit washer and dryer (an amenity not always found in Key West). Sharing just one common wall, the home lives much like a private cottage with its own entrance, parking, and a fenced backyard currently with a deck, designed for relaxing, entertaining, or enjoying island life. Recent renovations include hurricane-impact windows, updated plumbing, newer air conditioning, and stylish finishes that make this property truly move-in ready. Ideally located in Mid-Town along Key West's cross-town bike path, you'll enjoy quick access to beaches, shopping, dining, and Old Town. At $449,000, this is an outstanding alternative to condo living with the added benefits of private outdoor space, no shared hallways, and the comfort of a home that is ready to enjoy from day one. (condo docs to be filed). Call today for your personal tour.

2515 Staples Ave Unit Unit B, Key West
$2,150,000
3 Beds ⋅ 2 Baths ⋅ 619599 MLS
Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush landscaping. Located in the heart of Old Town, you're just moments from dining, shops, and the vibrant local scene, yet enjoy the peace and privacy of a hidden setting. Additional highlights include off-street parking--a rare and valuable convenience in this sought-after neighborhood. Whether you're seeking a full-time residence, vacation home, or investment property, this cottage captures the essence of Key West living. Possible Seller financing. .

810 Carey Ln, Key West
$2,550,000
3 Beds ⋅ 4 Baths ⋅ 619579 MLS
Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old Town cottage masterfully reimagined for the modern connoisseur. Tucked away on a tranquil lane, yet moments from the Historic Seaport and Duval Street, this three bedroom, three and a half bath home is the ultimate blend of calm island style and sophisticated Key West living. From the quintessential front porch to the vibrant, playful interiors, every inch of this home radiates personality. The heart of the residence features rare, historic Dade County Pine walls and floors bathed in natural light, creating a warm, textured backdrop for the home's contemporary finishes. The thoughtfully designed L-shaped layout effortlessly connects the chef's kitchen-complete with granite countertops and stainless appliances-to the bar and living areas. This social heart of the home seamlessly merges with an expansive dining area, where impact-rated French doors invite the island breeze, creating a natural environment for entertaining. The floor plan includes a coveted first-floor primary suite for ultimate convenience. The home's artistic soul is further defined by a series of custom murals by artist Haley Leeper, most notably the hand-painted staircase, which creates an artistic transition to the second floor. Upstairs features a second primary bedroom with a spa-inspired bath and an intimate reading nook and an additional guest suite. The backyard is a secluded oasis, boasting a heated pool and spa with an upgraded system, outdoor shower, and Trex decking. Framed by lush tropical foliage and a magnificent, mature mango tree, this space offers a level of privacy and shade. Complete with off-street parking and a distinguished track record as a top-performing monthly rental, 1017 Angela Street is a ''turnkey'' treasure that perfectly balances historic architectural significance with lucrative investment potenti

1017 Angela St, Key West
$874,999
3 Beds ⋅ 2 Baths ⋅ 619565 MLS
This sophisticated residence features off-street parking for two vehicles or a boat and is just a block away from the community boat ramp. Recent upgrades include hardie board siding, acoustic, and hurricane-rated doors and windows. An independent storage shed that offers additional storage space. The backyard provides a serene outdoor area perfect for enjoying the island lifestyle. The focus on high-quality finishes, expansive outdoor living, and an inviting design radiates luxury and comfort, making it ideal for entertaining friends and family. The location provides convenient access to exceptional dining, coffee shops, shopping, as well as recreational amenities such as sports venues and schools. Its proximity to the beach and downtown, coupled with low-maintenance landscaping, enhances its appeal and renders it a perfect choice for embracing the island lifestyle with luxury and comfort.

2805 Flagler Ave, Key West
$1,249,000
3 Beds ⋅ 3 Baths ⋅ 619554 MLS
Historic Old Town Key West home offering character, a prime location, and strong potential for a buyer looking to add value. Originally built in 1908 and positioned on a desirable corner lot, this 3-bedroom, 3-bath property is just moments from galleries, dining, the waterfront, and Key West's well-known sunsets. The interior features high ceilings, Dade County pine floors, and an open living and dining layout with good natural light. The kitchen includes gas cooking, ample storage, and a functional footprint that can be updated or reconfigured to fit your needs. Upstairs, the primary suite offers vaulted ceilings with exposed beams and an en-suite bath with mosaic tilework. Additional bedrooms provide flexibility for guests, roommates, or rental use. Exterior features include multiple porch areas, mature tropical landscaping, and a private yard. Off-street parking, a spacious pantry, and distinctive details such as a hand-carved Brazilian mahogany front door contribute to the home's overall value. Located in the heart of Old Town, this property presents an opportunity for a full-time residence, second home, or investment in one of Key West's most desirable neighborhoods.

846 Olivia St, Key West
$749,000
2 Beds ⋅ 2 Baths ⋅ 619553 MLS
First time ever on the market! This is an excellent opportunity to own a charming single-family home in Key West. Lovingly maintained and custom-built for the current owners, this property has remained in the same family for over 60 years. This tranquil residence features 2 bedrooms and 2 bathrooms and sits on a spacious 5,016 sq. ft. lot. The home includes off-street, covered parking for one vehicle. Recent updates include central A/C and a new water heater. A detached metal storage shed provides additional storage space. The backyard offers a relaxing outdoor area--perfect for enjoying the island lifestyle. Inside, tile flooring runs throughout the home for easy maintenance. The yard features mature tropical landscaping with local fruit bearing trees. Centrally located, this property is just minutes from shopping, schools, dining, and beaches. This mid-century modern home offers great potential for upgrades, renovations, or possible additions to suit your needs. The property is being sold as-is and is currently tenant-occupied, offering flexibility for investors or future homeowners ready to create their own vision. Listing agents are related to the sellers.

1618 Flagler Ave, Key West