Ianslistings.com Search Results

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.

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

$1,675,000

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.

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

$2,290,000

Four Apartment Property with Off Street Parking 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 a duplex or 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.

5 Beds ⋅ 4 Baths ⋅ 619927 MLS

Four Apartment Property with Off Street Parking 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 a duplex or 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

2601 S Roosevelt Blvd Unit APT 103C, Key West

$888,000

Now offered at $889,000, this 2-bedroom, 2-bath Key West beachfront condo sits ground-floor at Key West by the Sea, directly across from Smathers Beach, a rare setup that lets you walk to the sand without stairs, elevators, or commuting. At 1,221 square feet, the 3BR deeded layout lives comfortably open, with room to actually use the space rather than just pass through it. Dual-zone split A/C allows personalized comfort. Hurricane-impact, soundproof windows and doors provide enhanced security, energy efficiency, and peace of mind all year long. Inside, luxurious porcelain flooring runs throughout, paired with detailed bathroom tile work chosen to match the quality of the rest of the home. The kitchen carries soft-touch cabinetry and granite countertops -- quiet, durable choices that hold up well in a beach environment, which matters more here than most out-of-state buyers realize until they've owned property in the Keys for a few years. Key West by the Sea is a managed beachfront community with resort-style amenities, meaning pool, grounds, and building upkeep are handled for you offering low-maintenance, turnkey ownership that buyers relocating from out of state especially value. The building has never flooded, a track record that matters as much as the view when you're evaluating waterfront property in the Florida Keys. This stretch of South Roosevelt Blvd sits between the Atlantic shoreline and the island's laid-back Old Town core, across the street from Smathers Beach, close to Key West International Airport, and minutes from Duval Street, the historic Bight, and Higgs Beach. It's the kind of setting where morning coffee happens on the terrace with saltwater air and pool views, evenings mean sunset over the water instead of a screen, and life moves at the pace islanders have always known: bike rides instead of traffic, conch culture instead of chain restaurants. That's the island lifestyle longtime locals like myself have watched hold its value for decades.

3 Beds ⋅ 2 Baths ⋅ 619926 MLS

Now offered at $889,000, this 2-bedroom, 2-bath Key West beachfront condo sits ground-floor at Key West by the Sea, directly across from Smathers Beach, a rare setup that lets you walk to the sand without stairs, elevators, or commuting. At 1,221 square feet, the 3BR deeded layout lives comfortably open, with room to actually use the space rather than just pass through it. Dual-zone split A/C allows personalized comfort. Hurricane-impact, soundproof windows and doors provide enhanced security, energy efficiency, and peace of mind all year long. Inside, luxurious porcelain flooring runs throughout, paired with detailed bathroom tile work chosen to match the quality of the rest of the home. The kitchen carries soft-touch cabinetry and granite countertops -- quiet, durable choices that hold up well in a beach environment, which matters more here than most out-of-state buyers realize until they've owned property in the Keys for a few years. Key West by the Sea is a managed beachfront community with resort-style amenities, meaning pool, grounds, and building upkeep are handled for you offering low-maintenance, turnkey ownership that buyers relocating from out of state especially value. The building has never flooded, a track record that matters as much as the view when you're evaluating waterfront property in the Florida Keys. This stretch of South Roosevelt Blvd sits between the Atlantic shoreline and the island's laid-back Old Town core, across the street from Smathers Beach, close to Key West International Airport, and minutes from Duval Street, the historic Bight, and Higgs Beach. It's the kind of setting where morning coffee happens on the terrace with saltwater air and pool views, evenings mean sunset over the water instead of a screen, and life moves at the pace islanders have always known: bike rides instead of traffic, conch culture instead of chain restaurants. That's the island lifestyle longtime locals like myself have watched hold its value for decades.

2601 S Roosevelt Blvd Unit APT 103C, Key West

$1,599,999

Endless possiblities! Two units to rent for the investor or live in one and produce income from the other unit. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have a 2/1 floor plan and a mother in law lock out. All units have W/D hook ups and central air. 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.

7 Beds ⋅ 5 Baths ⋅ 619911 MLS

Endless possiblities! Two units to rent for the investor or live in one and produce income from the other unit. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have a 2/1 floor plan and a mother in law lock out. All units have W/D hook ups and central air. 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

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.

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

$839,900

Welcome to island living in the highly sought-after Key West Golf Club community! This beautifully maintained home at 34 Golf Club Drive offers the perfect blend of comfort, upgrades, and convenience in a gated neighborhood just minutes from Old Town Key West. This light-filled home features an open-concept living area with soaring ceilings, luxury vinyl plank flooring, and sliding glass doors that bring the outdoors in. The updated kitchen offers quartz countertops, white cabinetry, stainless steel appliances, and a functional layout ideal for entertaining or everyday living. Thoughtful upgrades include impact windows on the front and back of the home, hurricane shutters for major entrances and side windows, spray foam insulation in the crawl space, and a newer air handler installed approximately five years ago. A new rear fence and gate provide direct access to the golf course, while peaceful views of the 5th and 6th holes and lagoon create a relaxing island atmosphere. The upstairs bedrooms feature beautiful vaulted ceilings, adding charm and an airy feel throughout the upper level. Outdoor spaces are surrounded by mature tropical landscaping, perfect for relaxing or entertaining. Additional highlights include a termite guarantee already in place for added peace of mind and an assumable VA loan for military buyers with an exceptionally low 1.99% interest rate. Subject to lender approval and VA guidelines. Non-military buyers may not assume the loan due to the fact, the seller wishes to keep his Entitlement. Residents of the Key West Golf Club community enjoy access to resort-style amenities including two pools, a fitness center, gated security, and beautifully maintained grounds. Whether you're searching for a primary residence, second home, or investment opportunity, this property captures the essence of easy Key West living.

3 Beds ⋅ 2 Baths ⋅ 619859 MLS

Welcome to island living in the highly sought-after Key West Golf Club community! This beautifully maintained home at 34 Golf Club Drive offers the perfect blend of comfort, upgrades, and convenience in a gated neighborhood just minutes from Old Town Key West. This light-filled home features an open-concept living area with soaring ceilings, luxury vinyl plank flooring, and sliding glass doors that bring the outdoors in. The updated kitchen offers quartz countertops, white cabinetry, stainless steel appliances, and a functional layout ideal for entertaining or everyday living. Thoughtful upgrades include impact windows on the front and back of the home, hurricane shutters for major entrances and side windows, spray foam insulation in the crawl space, and a newer air handler installed approximately five years ago. A new rear fence and gate provide direct access to the golf course, while peaceful views of the 5th and 6th holes and lagoon create a relaxing island atmosphere. The upstairs bedrooms feature beautiful vaulted ceilings, adding charm and an airy feel throughout the upper level. Outdoor spaces are surrounded by mature tropical landscaping, perfect for relaxing or entertaining. Additional highlights include a termite guarantee already in place for added peace of mind and an assumable VA loan for military buyers with an exceptionally low 1.99% interest rate. Subject to lender approval and VA guidelines. Non-military buyers may not assume the loan due to the fact, the seller wishes to keep his Entitlement. Residents of the Key West Golf Club community enjoy access to resort-style amenities including two pools, a fitness center, gated security, and beautifully maintained grounds. Whether you're searching for a primary residence, second home, or investment opportunity, this property captures the essence of easy Key West living.

34 Golf Club Dr, Key West

$1,025,000

This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

2 Beds ⋅ 2 Baths ⋅ 619778 MLS

This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

1800 Atlantic Blvd Unit 427C, Key West

$1,250,000

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.

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

$2,399,000

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

2 Beds ⋅ 3 Baths ⋅ 619742 MLS

Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

800 Fleming St Unit Unit C1, Key West

$1,875,000

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.

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

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.

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

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.

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

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.

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

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.

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

$2,499,000

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.

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

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.

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

$2,380,000

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.

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

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.

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

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.

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

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 $4,500, $3,500, and $3,400 per month, bringing in a total annual income of $136,800 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.

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 $4,500, $3,500, and $3,400 per month, bringing in a total annual income of $136,800 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

$449,000

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.

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

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. .

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

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

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

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.

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

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.

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

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.

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

3029 N Roosevelt Blvd Unit APT 11, Key West

$679,500

Welcome to your slice of paradise in the highly sought-after Key Cove community in Key West, FL, where island living meets enjoyable comfort. This beautifully designed townhome offers the perfect blend of coastal charm and modern convenience. Featuring a bright, open-concept layout, the living and dining spaces flow seamlessly with the well appointed kitchen. Ideal for entertaining or unwinding after a long day. Enjoy outdoor living with the covered balcony off of the living room. The Living Room & Foyer has updated Engineered Hardwood - European French Oak Flooring in March 2023. Kitchen Tile updated in August 2025. The stairs and Hallway have Hardwood flooring as well updated in June 2021. New Hot Water Heater in August 2025 along with updated Kitchen Light and Faucet in March 2026. Most of the rooms in the home have been freshly repainted with Sherwin Williams Paint. Upstairs features two spacious bedrooms with high ceilings. A gorgeous bathroom with plenty of light. There's also a hall laundry room for easier lifestyle duties. This home features covered parking with a garage door. Plenty of space underneath for extra storage. Key Cove residents love the laid-back lifestyle. Convenient location for food shopping, dining and entertainment. Also, there's a Community Pool to hangout and enjoy your day. Whether you're searching for a full-time residence or a second home, this home delivers the Key West lifestyle you've been waiting for and more.

2 Beds ⋅ 2 Baths ⋅ 619544 MLS

Welcome to your slice of paradise in the highly sought-after Key Cove community in Key West, FL, where island living meets enjoyable comfort. This beautifully designed townhome offers the perfect blend of coastal charm and modern convenience. Featuring a bright, open-concept layout, the living and dining spaces flow seamlessly with the well appointed kitchen. Ideal for entertaining or unwinding after a long day. Enjoy outdoor living with the covered balcony off of the living room. The Living Room & Foyer has updated Engineered Hardwood - European French Oak Flooring in March 2023. Kitchen Tile updated in August 2025. The stairs and Hallway have Hardwood flooring as well updated in June 2021. New Hot Water Heater in August 2025 along with updated Kitchen Light and Faucet in March 2026. Most of the rooms in the home have been freshly repainted with Sherwin Williams Paint. Upstairs features two spacious bedrooms with high ceilings. A gorgeous bathroom with plenty of light. There's also a hall laundry room for easier lifestyle duties. This home features covered parking with a garage door. Plenty of space underneath for extra storage. Key Cove residents love the laid-back lifestyle. Convenient location for food shopping, dining and entertainment. Also, there's a Community Pool to hangout and enjoy your day. Whether you're searching for a full-time residence or a second home, this home delivers the Key West lifestyle you've been waiting for and more.

3029 N Roosevelt Blvd Unit APT 11, Key West

$1,799,999

Waterfront, turnkey, and completely private 2412 Linda Avenue delivers the ultimate Key West lifestyle. This fully renovated tropical retreat is designed for effortless indoor outdoor living offering the perfect blend of entertaining space and serene seclusion.The home features 2 bedrooms plus a flexible office/optional third bedroom with a bright open layout and a sunken living and dining area overlooking the pool and water through expansive windows.The primary suite is a standout, featuring a walk in closet and a spa inspired indoor outdoor ensuite with a dual head open air shower surrounded by lush palms. Outside the property lives like a private resort complete with a heated and chilled saltwater pool/spa, outdoor kitchen, and mature tropical landscaping. With direct water frontage you can easily enjoy the natural surroundings right from your backyard. Extensively improved and move in ready this home offers a seamless combination of comfort, style, and functionality.

2 Beds ⋅ 2 Baths ⋅ 619539 MLS

Waterfront, turnkey, and completely private 2412 Linda Avenue delivers the ultimate Key West lifestyle. This fully renovated tropical retreat is designed for effortless indoor outdoor living offering the perfect blend of entertaining space and serene seclusion.The home features 2 bedrooms plus a flexible office/optional third bedroom with a bright open layout and a sunken living and dining area overlooking the pool and water through expansive windows.The primary suite is a standout, featuring a walk in closet and a spa inspired indoor outdoor ensuite with a dual head open air shower surrounded by lush palms. Outside the property lives like a private resort complete with a heated and chilled saltwater pool/spa, outdoor kitchen, and mature tropical landscaping. With direct water frontage you can easily enjoy the natural surroundings right from your backyard. Extensively improved and move in ready this home offers a seamless combination of comfort, style, and functionality.

2412 Linda Ave, Key West

$1,100,000

With five bedrooms and three bathrooms, it seems perfect for families or hosting guests. The location ensures easy access to fantastic dining, coffee shops, and shopping, along with recreational options like sports venues and schools. The emphasis on beautiful finishes and an inviting floor plan suggests a luxurious yet comfortable living space, ideal for entertaining. Plus, the proximity to the beach and downtown, complemented by lush landscaping and tropical breezes, adds to its charm.

5 Beds ⋅ 3 Baths ⋅ 619531 MLS

With five bedrooms and three bathrooms, it seems perfect for families or hosting guests. The location ensures easy access to fantastic dining, coffee shops, and shopping, along with recreational options like sports venues and schools. The emphasis on beautiful finishes and an inviting floor plan suggests a luxurious yet comfortable living space, ideal for entertaining. Plus, the proximity to the beach and downtown, complemented by lush landscaping and tropical breezes, adds to its charm.

2922 Flagler Ave, Key West