Charming remodeled 1929 Old Town Key West home on iconic Margaret Street, offering privacy, new impact windows & doors, flooring and timeless island feel. Set back from the street, this three-bedroom, two-bath residence feels like a peaceful retreat while remaining close to Duval Street and the historic seaport. The outdoor living space features a beautiful pool and spa area surrounded by a spacious deck, perfect for relaxing and entertaining. A small separate pool house with a half bath adds convenience and flexibility (not included in square footage). A rare opportunity to enjoy classic Key West charm with exceptional outdoor living in a prime location.
Located in the heart of Old Town Key West's sought-after White Street Gallery District, this beautifully renovated 2-bedroom, 1-bath condo offers the perfect blend of island charm, outdoor living, and investment potential. A rare highlight is the expansive private outdoor space, featuring two distinct areas: an open-air sun deck ideal for relaxing and entertaining, and a screened lanai with built-in seating designed for dining and social gatherings year-round. Inside, the residence is filled with natural light from abundant windows and showcases classic Key West character with original Dade County Pine. The updated interior includes a modern kitchen and renovated bath, and the condo is offered fully furnished for immediate enjoyment or continued rental use. The spacious primary bedroom features an oversized closet, while the second bedroom functions perfectly as a guest room or home office. A washer and dryer are conveniently located within the unit. The building boasts a new metal roof and is located in the desirable X Flood Zone—key advantages for storm security and lower insurance costs. Additional features include coveted off-street assigned parking, exterior storage closet, and a proven rental history, having been successfully rented seasonally and monthly for over 12 years. BONUS: Neighboring 1 BR unit also available @$769k! An exceptional opportunity to own a turnkey Old Town condo with outdoor living, strong rental performance, and a prime gallery district location.
1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath condominium has been masterfully remodeled with designer finishes, offering a home that's as stylish as it is functional. Step inside to a sunlit, open-concept living space where clean lines and bamboo hardwood floors set a contemporary tone. The spacious chef's kitchen anchors the main floor with Samsung appliances, custom cabinetry, and a butcher block island that doubles as the perfect gathering spot for friends and neighbors. From morning coffee to evening cocktails, this is the heart of the home—where Key West stories begin. Upstairs, the airy loft-style second bedroom and bath create a private retreat with flexible space for guests or a home office. The primary suite is a sanctuary of calm, complete with a spa-like bathroom featuring HansGrohe fixtures and artistic touches that reflect the island's vibrant spirit. Every detail here is designed for comfort and ease: an HVAC system, Samsung washer/dryer, hot-water heater, and keyless entry make for effortless, low-maintenance living. A small private outdoor nook gives you a spot to soak up the island air—perfect for an afternoon read or greeting the day with sunshine and palm trees. The lifestyle at 1014 Truman Avenue is as compelling as the home itself. Just a short stroll brings you to Bayview Park for tennis, the Casa Marina District, white-sand beaches, and Old Town's world-class dining and nightlife. Tucked within the X-flood zone and in pristine condition, this home delivers both peace of mind and the ultimate in island convenience. Whether as a full-time residence or your tropical getaway, this condo is the definition of contemporary Key West living: vibrant, sophisticated, and unmistakably relaxed. Schedule your private showing today!
Experience the charm of this bright and airy 1-bedroom, 1-bathroom Southpark Condominium located in the prestigious Casa Marina neighborhood. Known for its tranquil atmosphere and prime location, this condominium is just a short stroll from Higgs Beach, the beloved Salute! on the Beach, and the iconic Louie's Backyard, where you can enjoy breathtaking ocean views and savor fine dining. Enjoy two inviting outdoor spaces: a welcoming front deck perfect for people-watching and a private deck off the primary bedroom, ideal for relaxing among lush, mature tropical landscaping. Convenience is key with an assigned off-street parking spot and a spacious indoor locked storage area, keeping your belongings secure and organized. Resort-style amenities include access to a heated pool, surrounded by beautifully maintained tropical grounds within this private compound. Located only four blocks from Duval Street, you'll enjoy the best of Key West's dining, shopping, and entertainment, all while savoring the peace and privacy of your own tropical oasis. If you've ever dreamed of living every day like a vacation, don't miss this chance to own a piece of paradise!
This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West. The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops, custom cabinetry, and stainless steel Thermador appliances. New tile flooring, updated lighting, and fully renovated bathrooms with clean modern finishes create a bright and comfortable interior throughout. The home also includes a new central air conditioning system and discreet security cameras that blend seamlessly into the design. A new roof adds peace of mind and makes this a true move in ready property. Outside, the home offers 56 feet of concrete seawall along a calm canal, providing excellent dockage potential and easy access for boating and paddleboarding. The outdoor space includes a bar and grilling area that is ideal for entertaining, along with a fully fenced yard finished with low maintenance turf for privacy and ease of care. The location is one of the home's strongest features. It is close to schools and the local high school and is within five minutes of grocery stores, restaurants, and beaches. Downtown Key West is approximately ten minutes away, offering quick access to Old Town, shopping, dining, and entertainment. This is a rare opportunity to own a fully renovated canal front home with flexible living space, boat ready frontage, and a central Key West location. One of the owners is a Licensed Florida Realtor.
Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined kitchen with Fisher & Paykel and Bosch appliances, a walk-in pantry, under-cabinet lighting, and refined finishes throughout. Outdoors, a secluded patio is framed by vibrant tropical landscaping and includes a tranquil water-featured pool, outdoor shower, and dedicated golf cart parking—the preferred way to get around Old Town. Offered fully furnished with a curated interiors package by Ben Teague Design, the home is move-in ready and thoughtfully finished. Set within a well-structured HOA with no shared walls, and part of a three-residence property with two additional homes positioned at the front and parking conveniently located there, this residence represents Old Town living at its most refined—entirely new, intentionally designed, and quietly confident in every detail.
Solid CBS 3-bedroom, 2-bath home situated on a 5,000 sq ft lot in desirable Midtown Key West. This well-maintained residence features a functional split floor plan with a private primary suite and bright, open living spaces that flow seamlessly to the outdoors. The kitchen offers ample cabinetry, pantry storage, and a comfortable dining area. The living room opens through sliding glass doors to a private backyard retreat showcasing an expansive heated saltwater above-ground pool with a wide-entry shallow area and tranquil water feature. Mature tropical landscaping, including mango and sapodilla trees, provides exceptional privacy, while the generous pool deck offers ample space for lounging and entertaining. Additional highlights include central A/C, storm shutters, ample off-street parking, and a large storage shed. Ideally located near schools, beaches, dining, and shopping, this property offers durability, comfort, and authentic island living.
The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West—authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction completed in January 2026 and every system, surface, and finish entirely new. Offered fully furnished with a bespoke interiors program by Ben Teague Design, the residence is layered with thoughtful selections, timeless materials, and a quiet sophistication that feels both intentional and effortlessly livable. The home offers two bedrooms and two-and-a-half baths, including an upstairs primary bedroom that opens to a classic Key West porch, while a second porch downstairs extends the living space and reinforces the home's effortless indoor-outdoor rhythm. Architect-led design and professionally curated landscaping elevate the curb appeal to a truly top-tier example of Old Town style—timeless proportions, thoughtful detailing, and a presence that feels historic without feeling precious. The property is part of a thoughtfully structured HOA, which also includes one attached residential unit positioned to the rear of the main home, as well as a separate detached unit located at the back of the property—allowing for shared stewardship while preserving privacy and architectural integrity. Set on one of the highest elevation blocks in Old Town and located in the coveted X-500 flood zone, this is a rare opportunity to own a home where heritage, design integrity, and modern peace of mind converge on one of Key West's most iconic streets.
Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!
Meticulously renovated 1866 Conch Revival perched atop Solaris Hill in the heart of Old Town and Steps from Old Town's vibrant culture, dining, and entertainment. This historic gem blends rich heritage with contemporary comforts offering an open Floor plan, 2 primary bedroom options (one on first level), X Flood Zone, cocktail pool, hammock porch and more! Step into the foyer at the corner of Southard & Love, where preserved architectural details meet modern sophistication. Dade County pine adds authentic charm throughout, complementing the open-concept living & dining areas. High ceilings, natural light & hardwood floors enhance the seamless blend of old & new. The gourmet kitchen features top-of-the-line appliances, custom cabinetry and quartz countertops. The spacious island connects the kitchen to the living areas, creating a cohesive flow. 4 bedrooms, 3 with renovated ensuite bathrooms. The main floor primary bedroom is a luxurious retreat with a spa-like bathroom, walk-in closet, & French doors offering serene island views. An additional main floor ensuite bedroom provides comfort for family or guests. The alternate primary bedroom retreat on the second floor with WIC, vaulted ceiling & newly renovated ensuite bathroom boasts Dade County pine, an office or sitting area with a surround of French doors and hammock porch with a perfect breeze anxiously awaiting. A third level bedroom completes this stunning home. Outside, enjoy a private tropical paradise with lush tropical landscaping, sunlit multi-level deck, & a refreshing, heated & jetted cocktail dipping pool. The rare off-street parking spot adds convenience in this prime Old Town location.
MOTIVATED SELLERS offering possible Seller Financing....Reduced again! NEW PRICE: This exceptional turnkey three-bedroom, three bath and one half-bath residence is located in the prestigious Casa Marina neighborhood, one of Key West's most sought-after enclaves. Showcasing timeless Spanish Colonial architecture, the home offers a bright, open floor plan enriched with elegant architectural details and enchanting stained glass accents throughout. The main level is warm and inviting, featuring a graceful arched entry that flows seamlessly into expansive living and dining areas, a well-appointed kitchen, and a full bath--ideal for both refined entertaining and relaxed island living. Just beyond the kitchen, a stunning loggia with spa, creates an extraordinary outdoor living and dining space, framed by arched openings that overlook the private pool and lush rear yard. Upstairs, three beautifully appointed bedrooms feature rich wood flooring, wood ceilings, and 3 skylights that bathe the spaces in natural light. The primary suite is a true retreat, offering a generous private sundeck with serene views, also accessible from the pool deck via a dramatic spiral staircase. Additional luxury amenities include covered parking, privacy fencing, a whole home generator, and an unbeatable location in an elegant neighborhood close to world-class dining, beaches, and all the vibrant offerings of Key West.
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!
Welcome to Old Key West luxury living in this beautifully appointed 2-bedroom, 2-bathroom condo, ideally located in an X flood zone. This residence features hardwood floors, high ceilings, crown molding, granite countertops, and stainless steel appliances, creating a refined yet relaxed island aesthetic. The open-concept layout flows effortlessly for everyday living and entertaining, while the two balconies offer the perfect spot to enjoy the Island breeze. An updated kitchen, and thoughtful finishes throughout complete this elegant retreat. Step outside to lush tropical landscaping, exterior evening lighting, and a resort-style heated pool just steps from your front door. Enjoy the convenience of one assigned off-street parking space and the unbeatable location walking distance to downtown restaurants, art galleries, world-famous sunsets and the energy of Duval Street. You are steps away from Truman Waterfront and Fort Zachary Taylor State Park. This is a rare opportunity to own a private slice of paradise that perfectly balances tranquility, walkability, and classic Key West charm. PARKING - FULL SIZE LAUNDRY- POOL- CENTRAL AC!
Welcome to 1505 Rose Street in Key West, Florida! This legal duplex is perfect -- feels just like a single family home with a nice guest house, but can easily be rented out to two different tenants if need be. A well-planned ground level home with a large pool and backyard for you to enjoy that perfect Key West weather. Location is key on this home, situated in a very nice quiet neighborhood, and just a short walk to the beach or a bike ride to all that Key West has to offer. Location, Location, Location! When you walk into the ground floor first unit home you are greeted with two (2) bedrooms and one (1) bathroom with an open kitchen and living room. Great space with a large living room. The second home is behind the first and is a two (2) bedroom and (2) bathroom, with the primary/master on the second floor in this unit. This unit could easily be the pool house or guest house if being used as a single family property. The backyard is fitted with a good size in-ground pool with plenty of room to soak up some sun, or just sit back and enjoy a beautiful dinner under the stars. This home is made for making great memories. Call today for your private showing!
Welcome to 1505 Rose Street in Key West, Florida! This legal duplex is perfect -- feels just like a single family home with a nice guest house, but can easily be rented out to two different tenants if need be. A well-planned ground level home with a large pool and backyard for you to enjoy that perfect Key West weather. Location is key on this home, situated in a very nice quiet neighborhood, and just a short walk to the beach or a bike ride to all that Key West has to offer. Location, Location, Location! When you walk into the ground floor first unit home you are greeted with two (2) bedrooms and one (1) bathroom with an open kitchen and living room. Great space with a large living room. The second home is behind the first and is a two (2) bedroom and (2) bathroom, with the primary/master on the second floor in this unit. This unit could easily be the pool house or guest house if being used as a single family property. The backyard is fitted with a good size in-ground pool with plenty of room to soak up some sun, or just sit back and enjoy a beautiful dinner under the stars. This home is made for making great memories. Call today for your private showing!
Nestled in the prestigious Casa Marina neighborhood, 1120 Seminary Street offers the quintessential Key West lifestyle with a perfect blend of charm, luxury, and tropical serenity. Located in an X Flood Zone. This enchanting bungalow boasts 2 bedrooms and 2.5 baths within the main home, where an open floor plan invites effortless entertaining and everyday living. Rich Dade County Pine accents on select walls add a touch of historic character to the bright, inviting interiors. Step outside, and you'll find your own private paradise. Lush tropical landscaping surrounds a serene water feature that could be converted into a Plunge Pool or Koi Pond, offering endless possibilities for relaxation and ambiance. Tucked away, there's a private outdoor shower perfect for relaxing and recharging in complete tranquility. Beyond the main home, a separate guest cottage awaits, equipped with a kitchen and bath--ideal for hosting visitors or creating a private retreat. Situated just moments from Higgs Beach and the vibrant energy of Duval Street, this home offers the perfect blend of seclusion and accessibility. Whether you're seeking a full-time haven or a seasonal retreat, 1120 Seminary Street is a rare gem in one of Key West's most coveted neighborhoods. Don't miss the opportunity to make this extraordinary property your own. Schedule your private tour today and discover the epitome of tropical luxury living.Some photos have been virtually staged.
This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated—so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. The nearly 5,000-square-foot lot stretches from Fleming Street to Stickeny Lane, offering ample off-street parking and a golden opportunity to expand your tropical living dreams. Nestled in the heart of Old Town, 1115 is just blocks from the historic Seaport and a stone's throw from the city's famous restaurants and nightlife. Early 1900s Sanborn maps even hint at an additional house on the property that may be rebuilt with city permissions (buyers to verify). The home still contains generous pockets of its original Dade County pine, along with historic windows and double balconies that invite sea breezes and sunset cocktails. Currently a legal duplex, each side offers 2 bedrooms and 1 bath. You can keep the duplex as-is, or transform it into a stunning single-family residence in the most sought-after neighborhood in all of Key West.
Discover your perfect docking solution with this 60 foot boat slip (65 foot LOA) located at the sheltered and protected Sunset Marina in Key West. Positioned on the Gulf side of Key West, this slip provides deep water access, ideal for both large and small vessels. At the entrance to the property owners will find an electric gate providing increased security. Owners will enjoy the exclusive access to the fabulous pool and private events room just steps away from the dock. The slip is equipped with essential amenities such as freshwater and shore power, ensuring your boat is well-maintained and ready for your next adventure. Whether you're a local or a seasonal visitor, this slip offers a secure and convenient spot for your vessel. Don't miss this opportunity to secure a premier boat slip in one of Key West's finest marinas.
3605 Eagle Avenue Key West Situated on one of Key West's most desirable streets, this private compound on Eagle Avenue offers a rare combination of space, privacy, and refined island living. Set on a double corner lot totaling 12,000 sq ft, the property is fully enclosed, offering enhanced privacy and a tranquil, resort-like setting. The main residence features 3 bedrooms, 2.5 baths, and approximately 1,765 sq ft of thoughtfully designed living space with a comfortable open floor plan ideal for entertaining. The spacious primary suite serves as a private retreat, complete with a large en suite bath featuring a walk-in shower and oversized Jacuzzi tub. A separate guest cottage offers 1 bedroom, 1 bath, and approximately 625 sq ft, providing excellent flexibility for guests, extended family, or additional living space. The professionally landscaped grounds are a standout feature, enhanced by landscape lighting and irrigation, and centered around a large pool set within an exceptionally private backyard. Outdoor amenities include a hammock and swing area, outdoor shower, and multiple areas for entertaining or quiet relaxation beneath the palms. Additional highlights include a whole-house generator, security system, one-car garage, and generous off-street parking. Surrounded by notable luxury homes, Eagle Avenue is known for its quiet atmosphere, large lots, and enduring desirability. A rare opportunity to own a private Key West compound offering privacy, flexibility, and presence on one of the island's most sought-after streets. Seller is a licensed real estate agent
Impeccably renovated Midtown retreat with guest cottage on a corner lot, framed by a classic white picket fence. This beautifully updated property offers a rare combination of charm, modern upgrades, and flexibility in one of Key West's most desirable residential neighborhoods. The 2-bedroom, 2-bath main house has been thoughtfully renovated throughout, featuring a brand-new kitchen, new metal roof (2022), new refrigerator, fully restored terrazzo floors, upgraded storage, and a fully renovated primary suite with ensuite bath and walk-in closet. Additional improvements include new central A/C ductwork, hurricane-rated sliding glass door, smart thermostat, retractable awning, new washer and dryer, and a new hot water heater. A generator with transfer switch adds peace of mind, while a newly built shed with hurricane tie-downs provides practical storage. The property is fully landscaped, including a native butterfly garden, creating a private tropical setting ideal for indoor-outdoor living. The separate 1-bedroom, 1-bath guest cottage offers excellent rental or guest accommodations with its own private entrance. The cottage features newly installed split A/C units, a renovated kitchen and bathroom with upgraded electrical and plumbing, hurricane-rated windows, and a new on-demand water heater. Cottage has option to come fully furnished. Set on a quiet corner lot, the fully enclosed fenced yard enhances privacy while offering both off-street and ample street parking—a true luxury in Key West. With a total of 3 bedrooms and 3 full baths, this property presents a compelling opportunity for full-time living, a second home, or a residence with strong rental income potential. Move-in ready, meticulously upgraded, and ideally located—this Midtown Key West home checks every box.
At the end of wide, quiet cul-de-sac, life naturally slows, sunsets linger, 20 Kingfisher reveals itself as a private island retreat @ KW Golf Club. Inviting brick walkway, lush tropical landscaping, river rock, lead to freshly painted front steps, welcoming front veranda that set the tone, refined, thoughtfully cared for. This home feels loved the moment you arrive. Inside, warmth & craftsmanship take center stage. Rich heart pine flooring grounds the main level, continuing up the staircase. Elegant, functional fully remodeled kitchen features custom cottage-style wooden cabinetry, soft-close drawers, luxurious granite countertops, beautiful built-in storage beneath the breakfast bar. All upgraded stainless appliances complete the space: new dishwasher, radiant cooktop range w/double ovens/convection, microwave, French-door refrigerator/freezer, every detail chosen for beauty & performance. From the living area, the home opens to a captivating, expanded screened rear veranda overlooking the lake, the #2 tee box & S.W. sky that delivers breathtaking sunsets. When the Royal Poinciana bursts into bloom, its fiery canopy becomes a work of art, reflected in the water, glowing at dusk, unforgettable! Upstairs, the home transforms into a tranquil private retreat. High-end luxury vinyl plank flooring w/padded underlayment provides a cushioned ''walking on air'' feel, waterproof, elegant, designed for long-term comfort. 2 spacious en-suite bedrooms anchor the 2nd level, defined by cozy architectural charm w/gentle eaved rooflines, adding character & intimate cottage feel. The primary suite is inviting w/a generous double closet & large built-in storage. En-suite bath is a true showpiece, featuring new pendant lighting, fully tiled walk-in shower w/built-in bench, wrapped in vibrant royal blue/burgundy ceramic tile. Guest bdrm. is mirrored image w/lg. extended closet. 3rd bdrm. is office/study. Private heated resurfaced pool upgraded w/steps/railing is divine. So much more!
Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels both timeless and current. LOCATED IN X Behind its unassuming facade lies a surprisingly expansive interior offering four bedrooms and four baths, including three bedrooms with three baths on the main level and a private upstairs bedroom with its own bath, ideal as a guest suite, apartment-style retreat, or income-producing space. An additional office or flex space off one of the bedroom suites allows work and relaxation to coexist effortlessly. The single-level main floor is designed with intention each bedroom enjoys privacy while remaining easily accessible. Interior details include travertine and Ipe Brazilian hardwood floors, wood-clad ceilings, and a gourmet kitchen outfitted with stainless steel appliances and a wrap-around peninsula that naturally becomes the heart of the home. Whether hosting friends or enjoying everyday living, the flow is intuitive and inviting. French doors throughout the home create a strong connection to the outdoors. One bedroom opens directly to the pool, while another enjoys a peaceful, tucked-away deck perfect for morning coffee or quiet reflection. The primary suite is a true sanctuary, featuring vaulted ceilings, a spacious marble bath with multi-jet shower, walk-in closet, and direct access to an expansive Ipe sundeck. Outside, a large heated pool anchors a lush, private oasis surrounded by tropical landscaping and a privacy fence ideal for entertaining or unwinding in complete tranquility. A shaded loggia adds yet another layer of livable outdoor space. Off-street parking, LOCATED IN X FLOOD ZONE provides rare Old Town convenience!
Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers. The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction in a prime setting. Paired with this is an existing 2-bedroom, 1-bath home, ideal for island living, income production, or incorporation into a larger architectural vision. Whether you're a builder seeking scarce development rights, an investor looking to maximize returns, or a buyer with a long-term Key West strategy, this is a once-in-a-market opportunity with limitless potential. Quietly tucked away yet steps from Key West's most celebrated dining, galleries, and waterfront experiences. This is Old Town Key West at its absolute best.
OFFERED FULLY FURNISHED and completely renovated, this is the townhome buyers wait for and almost never get. Every finish, every furnishing, and every detail has been thoughtfully curated to deliver a truly coastal lifestyle. Set within the exclusive, gated oceanfront enclave of Casa Caselles, this solid concrete home has been meticulously renovated with a focus on timeless materials and modern convenience. Mahogany staircases anchor the interior with warmth and craftsmanship, while electric blinds, smart TVs, and a full security system bring effortless, lock and leave peace of mind. The kitchen and living spaces are both beautiful and functional, featuring LG ThinQ appliances and a layout designed for everyday ease and entertaining alike. Impact doors and windows enhance durability and storm protection, while walk in closets provide storage rarely found in townhomes of this size. With 2 bedrooms, 2.5 baths, and 1,940 square feet of interior living space, the home flows naturally across multiple levels, complemented by outdoor areas that capture ocean breezes and sunrises. With no rentals allowed, Casa Caselles feels more like a private retreat than a condominium, and opportunities to purchase a renovated, fully furnished residence of this caliber are exceptionally rare. If you are looking for the best, the search stops here.
***BRAND NEW ROOF JUST INSTALLED *** 1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $130,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing. The layout includes two spacious 2-bedroom / 1-bath units and an upstairs 3-bedroom / 2-bath residence, providing multiple rental strategies and value-add potential. A standout feature is parking for up to 7 vehicles--a true luxury in Key West and a major draw for tenants. Large Shed on property with two dedicated spaces that could be converted into a workspace. Ideal for investors seeking steady returns or employers looking for quality workforce housing, this triplex combines strong income, practical design, and exceptional parking in one compelling opportunity. Please note some photos were digitally staged and or altered to protect tenant privacy.
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The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.
Key West is located in Florida. Key West, Florida has a population of 26,776. Key West is more family-centric than the surrounding county with 23.73% of the households containing married families with children. The county average for households married with children is 20.65%.
The median household income in Key West, Florida is $75,638. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Key West is 44.2 years.
The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.6 degrees. The average rainfall is approximately 43.8 inches per year, with 0 inches of snow per year.
