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2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

2 Beds ⋅ 2 Baths ⋅ 620647 MLS

2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

3312 N Northside Dr Unit 607, Key West

$1,139,000

Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

3 Beds ⋅ 2 Baths ⋅ 620641 MLS

Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

1708 South Street, Key West

$4,995,000

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

4 Beds ⋅ 5 Baths ⋅ 620618 MLS

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West

$4,200,000

An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

3 Beds ⋅ 5 Baths ⋅ 620614 MLS

An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

218 Whitehead St, Key West

$1,095,000

THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

4 Beds ⋅ 5 Baths ⋅ 620612 MLS

THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

1503 Atlantic Blvd, Key West

$1,575,000

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

3 Beds ⋅ 2 Baths ⋅ 620577 MLS

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

1005 Watson St Unit 1, Key West

$1,199,000

Welcome to Seaside Residences, one of Key West's most sought-after gated communities. This beautifully updated three-story townhome is one of the largest residences in the community, offering 2 bedrooms, 3.5 bathrooms, 1,824 square feet of thoughtfully designed living space, making it the second-largest property in Seaside Residences. A private elevator services all three levels, providing both comfort and convenience. Enjoy the best island living with three private balconies offering beautiful sunrise and sunset views, plus a private rooftop deck perfect for relaxing, entertaining, or soaking up the Florida sunshine. The ground level features a private garage, laundry area, half bath, and a spacious outdoor patio complete with a tranquil fountain and fire pit--an ideal space for gathering with family and friends. The second level offers a spacious primary suite with an ensuite bath featuring dual vanities and a large walk-in shower, while the guest bedroom enjoys its own private full bath. The top floor showcases an open-concept living, dining, and kitchen area filled with abundant natural light. The kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, generous pantry space, and an ideal layout for both everyday living and entertaining. Recent upgrades include a new air conditioning system, new water heater, and impact-resistant windows and doors throughout, providing peace of mind, energy efficiency, and storm protection. Residents enjoy exceptional community amenities including a resort-style pool, fitness center, and the convenience of building insurance covered through the HOA. Ideally located just steps beaches, Old Town Key West, world-class dining, shopping, marinas, and local attractions, this property also allows short-term rentals, making it an outstanding opportunity as a full-time residence, luxurious vacation home, or exceptional income-producing investment.

2 Beds ⋅ 4 Baths ⋅ 620515 MLS

Welcome to Seaside Residences, one of Key West's most sought-after gated communities. This beautifully updated three-story townhome is one of the largest residences in the community, offering 2 bedrooms, 3.5 bathrooms, 1,824 square feet of thoughtfully designed living space, making it the second-largest property in Seaside Residences. A private elevator services all three levels, providing both comfort and convenience. Enjoy the best island living with three private balconies offering beautiful sunrise and sunset views, plus a private rooftop deck perfect for relaxing, entertaining, or soaking up the Florida sunshine. The ground level features a private garage, laundry area, half bath, and a spacious outdoor patio complete with a tranquil fountain and fire pit--an ideal space for gathering with family and friends. The second level offers a spacious primary suite with an ensuite bath featuring dual vanities and a large walk-in shower, while the guest bedroom enjoys its own private full bath. The top floor showcases an open-concept living, dining, and kitchen area filled with abundant natural light. The kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, generous pantry space, and an ideal layout for both everyday living and entertaining. Recent upgrades include a new air conditioning system, new water heater, and impact-resistant windows and doors throughout, providing peace of mind, energy efficiency, and storm protection. Residents enjoy exceptional community amenities including a resort-style pool, fitness center, and the convenience of building insurance covered through the HOA. Ideally located just steps beaches, Old Town Key West, world-class dining, shopping, marinas, and local attractions, this property also allows short-term rentals, making it an outstanding opportunity as a full-time residence, luxurious vacation home, or exceptional income-producing investment.

33 Seaside S Ct, Key West

$849,000

Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3 Beds ⋅ 3 Baths ⋅ 620501 MLS

Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3712 Duck Ave, Key West

$1,475,000

PRIME INVESTMENT OPPORTUNITY! 3 Commercial Condos on White Street in X Flood Zone. Newly formed condo building on busy Old Town Street in HNC-1 zoning - uses include professional offices, retail sales & services, specialty shops, restaurants. 1 of the units (1206 White St.) is currently vacant and ready for immediate owner/operator occupancy or to lease to a new tenant. Well established tenants & businesses in place at 1200 & 1202 White St. (do not disturb businesses). Condos are also available to purchase individually. *3 Addresses/Parcel #'s - 1200 White St., 1202 White St., 1206 White St., (1204 White St. is NOT included in this offering, already sold) **Seller is a licensed Florida realtor.

3 Baths ⋅ 620495 MLS

PRIME INVESTMENT OPPORTUNITY! 3 Commercial Condos on White Street in X Flood Zone. Newly formed condo building on busy Old Town Street in HNC-1 zoning - uses include professional offices, retail sales & services, specialty shops, restaurants. 1 of the units (1206 White St.) is currently vacant and ready for immediate owner/operator occupancy or to lease to a new tenant. Well established tenants & businesses in place at 1200 & 1202 White St. (do not disturb businesses). Condos are also available to purchase individually. *3 Addresses/Parcel #'s - 1200 White St., 1202 White St., 1206 White St., (1204 White St. is NOT included in this offering, already sold) **Seller is a licensed Florida realtor.

1200-1206 White St, Key West

$945,000

PRIME COMMERCIAL SPACE - Two combined commercial condos on White Street in X Flood Zone! These 2,061sf 1st floor units have been extensively updated and renovated with hurricane rated impact windows & doors and come with 2 assigned parking spots (1 for each unit). The monthly condo fee includes windstorm and liability insurance. Condo docs & survey in documents tab. Tenant in place, please do not disturb business. HNC-1 zoning uses include professional offices, retail sales & services, specialty shops, restaurants. *Units can also be purchased separately. **Seller is a licensed Florida realtor.

1 Baths ⋅ 620494 MLS

PRIME COMMERCIAL SPACE - Two combined commercial condos on White Street in X Flood Zone! These 2,061sf 1st floor units have been extensively updated and renovated with hurricane rated impact windows & doors and come with 2 assigned parking spots (1 for each unit). The monthly condo fee includes windstorm and liability insurance. Condo docs & survey in documents tab. Tenant in place, please do not disturb business. HNC-1 zoning uses include professional offices, retail sales & services, specialty shops, restaurants. *Units can also be purchased separately. **Seller is a licensed Florida realtor.

12001202 White St, Key West

$725,000

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

1 Beds ⋅ 1 Baths ⋅ 620493 MLS

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

308 Margaret St Unit 3, Key West

$575,000

PRIME OPPORTUNITY FOR OWNER/OPERATOR! Commercial condo available with over 1,300 sq. ft. centrally located in Old Town. This is an end unit and has a half bath, hurricane rated windows and doors, features one assigned parking spot and is located in the X Flood Zone. Also has an office space in the back that can be rented out separately for additional income. The monthly condo fee for this unit is $729.45 and includes windstorm and liability insurance. 2 other commercial condos also available. *Seller is a licensed Florida realtor.

1 Baths ⋅ 620484 MLS

PRIME OPPORTUNITY FOR OWNER/OPERATOR! Commercial condo available with over 1,300 sq. ft. centrally located in Old Town. This is an end unit and has a half bath, hurricane rated windows and doors, features one assigned parking spot and is located in the X Flood Zone. Also has an office space in the back that can be rented out separately for additional income. The monthly condo fee for this unit is $729.45 and includes windstorm and liability insurance. 2 other commercial condos also available. *Seller is a licensed Florida realtor.

1206 White St, Key West

$450,000

Prime commercial space available with 892sf centrally located in Old Town. Unit has hurricane rated windows and doors, features one assigned parking spot and is located in the X Flood Zone. The monthly condo fee for this unit is $468.48 and includes windstorm and liability insurance. Tenant in place, do not disturb business. Condo docs & survey in documents tab. HNC-1 zoning uses include professional offices, retail sales & services, specialty shops, restaurants. *2 other commercial condos also available. *Seller is a licensed Florida realtor.

1 Baths ⋅ 620483 MLS

Prime commercial space available with 892sf centrally located in Old Town. Unit has hurricane rated windows and doors, features one assigned parking spot and is located in the X Flood Zone. The monthly condo fee for this unit is $468.48 and includes windstorm and liability insurance. Tenant in place, do not disturb business. Condo docs & survey in documents tab. HNC-1 zoning uses include professional offices, retail sales & services, specialty shops, restaurants. *2 other commercial condos also available. *Seller is a licensed Florida realtor.

1202 White St, Key West

$535,000

Newly formed commercial condo now available for sale on White Street in X Flood Zone! This 1,169sf 1st floor corner unit has been extensively updated and renovated with hurricane rated impact windows & doors and comes with 1 assigned parking spot. The monthly condo fee for this unit is $614.37 and includes windstorm and liability insurance. Condo docs & survey in documents tab. Tenant in place, please do not disturb business. HNC-1 zoning uses include professional offices, retail sales & services, specialty shops, restaurants. *2 other commercial condos also available. **Seller is a licensed Florida realtor.

1 Baths ⋅ 620482 MLS

Newly formed commercial condo now available for sale on White Street in X Flood Zone! This 1,169sf 1st floor corner unit has been extensively updated and renovated with hurricane rated impact windows & doors and comes with 1 assigned parking spot. The monthly condo fee for this unit is $614.37 and includes windstorm and liability insurance. Condo docs & survey in documents tab. Tenant in place, please do not disturb business. HNC-1 zoning uses include professional offices, retail sales & services, specialty shops, restaurants. *2 other commercial condos also available. **Seller is a licensed Florida realtor.

1200 White St, Key West

$1,825,000

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

2 Beds ⋅ 2 Baths ⋅ 620470 MLS

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

1115 South Street, Key West

$584,900

Updated home in a prime central Key West location! Perfect for a local buyer or as an affordable second home in a quieter part of town, this move-in-ready property offers comfort, convenience, and tropical charm. The home features two generously sized bedrooms, two full bathrooms, and is situated on a corner lot in New Town. Warm wood flooring runs throughout, while the kitchen and dining area showcase Corian countertops, stainless steel appliances, classic wainscoting details, and a timeless neutral coastal palette that creates a bright, relaxed island atmosphere. French doors offer a bright and inviting living area and open to a composite deck and a lush, fully fenced yard, creating an ideal setting for indoor-outdoor living. Enjoy your morning coffee from the upstairs porch overlooking the tropical landscape, complete with a peek-a-boo view of the nearby park and recreational facilities. The private, gated yard is a true island retreat, featuring banana and mature mango trees that produce an abundance of fruit, vibrant bougainvillea, and an outdoor shower that's perfect after beach or boating days. Additional highlights include off-street parking, no HOA fees, and a welcoming townhome-style layout designed for easy living. Conveniently located near schools, shopping, beaches, grocery stores, sports fields, and movie theaters, this home offers the best of the Key West lifestyle, with everyday conveniences just a short walk or bike ride away.

2 Beds ⋅ 2 Baths ⋅ 620466 MLS

Updated home in a prime central Key West location! Perfect for a local buyer or as an affordable second home in a quieter part of town, this move-in-ready property offers comfort, convenience, and tropical charm. The home features two generously sized bedrooms, two full bathrooms, and is situated on a corner lot in New Town. Warm wood flooring runs throughout, while the kitchen and dining area showcase Corian countertops, stainless steel appliances, classic wainscoting details, and a timeless neutral coastal palette that creates a bright, relaxed island atmosphere. French doors offer a bright and inviting living area and open to a composite deck and a lush, fully fenced yard, creating an ideal setting for indoor-outdoor living. Enjoy your morning coffee from the upstairs porch overlooking the tropical landscape, complete with a peek-a-boo view of the nearby park and recreational facilities. The private, gated yard is a true island retreat, featuring banana and mature mango trees that produce an abundance of fruit, vibrant bougainvillea, and an outdoor shower that's perfect after beach or boating days. Additional highlights include off-street parking, no HOA fees, and a welcoming townhome-style layout designed for easy living. Conveniently located near schools, shopping, beaches, grocery stores, sports fields, and movie theaters, this home offers the best of the Key West lifestyle, with everyday conveniences just a short walk or bike ride away.

3201 Pearl Ave, Key West

$799,000

Duplex has 1,342 square feet of living space on a 2,841 square foot lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. Now offered separate from the vacant lot. Can also be purchased with lot at discounted price for both.

4 Beds ⋅ 2 Baths ⋅ 620461 MLS

Duplex has 1,342 square feet of living space on a 2,841 square foot lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. Now offered separate from the vacant lot. Can also be purchased with lot at discounted price for both.

1421-1425 2nd St, Key West

$1,050,000

Duplex with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. The adjoining 2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

4 Beds ⋅ 2 Baths ⋅ 620459 MLS

Duplex with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. The adjoining 2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

2001 Flagler Ave, Key West

$979,000

When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

4 Beds ⋅ 2 Baths ⋅ 620453 MLS

When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

1500 5th St, Key West

$950,000

Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along the horizon, and spend your afternoons relaxing beside the resort-style Olympic-size heated pool and spa, all set within lush tropical landscaping. Residents enjoy tennis and pickleball courts, an equipped fitness center, assigned covered parking, and professionally maintained grounds--delivering true comfort, simplicity, and peace of mind in a coastal setting. Recent upgrades include impact-rated doors and windows, enhancing storm protection, energy efficiency, and long-term ownership confidence while maintaining a clean, modern coastal aesthetic. Pet owners will appreciate the flexibility of 2 pets allowed (up to 50 lbs total). Monthly association fees include building insurance, exterior maintenance, professional management, water, high-speed internet - offering a truly turnkey lifestyle. Ideally located just minutes from Old Town Key West, you're close to world-class dining, galleries, marinas, and cultural events, yet tucked away in a quiet, oceanfront enclave that feels removed from it all. Whether by bike or a short drive, everything the island offers is within easy reach. Come experience why so many call this their Key West home away from home 🌴.

2 Beds ⋅ 2 Baths ⋅ 620451 MLS

Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along the horizon, and spend your afternoons relaxing beside the resort-style Olympic-size heated pool and spa, all set within lush tropical landscaping. Residents enjoy tennis and pickleball courts, an equipped fitness center, assigned covered parking, and professionally maintained grounds--delivering true comfort, simplicity, and peace of mind in a coastal setting. Recent upgrades include impact-rated doors and windows, enhancing storm protection, energy efficiency, and long-term ownership confidence while maintaining a clean, modern coastal aesthetic. Pet owners will appreciate the flexibility of 2 pets allowed (up to 50 lbs total). Monthly association fees include building insurance, exterior maintenance, professional management, water, high-speed internet - offering a truly turnkey lifestyle. Ideally located just minutes from Old Town Key West, you're close to world-class dining, galleries, marinas, and cultural events, yet tucked away in a quiet, oceanfront enclave that feels removed from it all. Whether by bike or a short drive, everything the island offers is within easy reach. Come experience why so many call this their Key West home away from home 🌴.

1800 Atlantic Blvd Unit 218B, Key West

$1,385,000

There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

3 Beds ⋅ 2 Baths ⋅ 620448 MLS

There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

2313 Fogarty Ave, Key West

$749,000

Charming Key West Cottage with large back yard and ROOM FOR A BIG POOL! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive. This beautifully updated 2 bedroom home has a bonus room for 3rd bedroom with own private full bath. The home is bursting with Key West charm and curb appeal! From the moment you step inside, you'll fall in love with the character and that unmistakable colorful warmth that only Key West living can deliver. Best of all? It's fully furnished and completely move-in ready. Just bring your toothbrush and your sunscreen, because everything else is already waiting for you.The versatile bonus space offers endless possibilities! Want a home office, guest overflow, art studio, workshop, or your very own private retreat? Step outside and discover the real showstopper: a spacious, lushly landscaped backyard that's practically begging for a sparkling pool 🏊. Whether you envision weekend soirées under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Practical perks? You've got those too. Off-street parking is a rare and treasured luxury in Key West and this property has it. No more circling the block after a long day at the beach. Located just moments from world-famous Duval Street, celebrated dining, vibrant nightlife, the Historic Seaport, and those legendary Key West sunsets 🌅, this property places you at the very center of the island lifestyle while offering a peaceful, private retreat to come home to.✨ Furnished & Move-In Ready, updated, Expansive Backyard with Pool Potential, Off-Street Parking, central Key West Location. If you are searching for a full-time residence, a vacation escape, or a high-demand rental investment, 2005 Fogarty Ave checks

3 Beds ⋅ 2 Baths ⋅ 620436 MLS

Charming Key West Cottage with large back yard and ROOM FOR A BIG POOL! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive. This beautifully updated 2 bedroom home has a bonus room for 3rd bedroom with own private full bath. The home is bursting with Key West charm and curb appeal! From the moment you step inside, you'll fall in love with the character and that unmistakable colorful warmth that only Key West living can deliver. Best of all? It's fully furnished and completely move-in ready. Just bring your toothbrush and your sunscreen, because everything else is already waiting for you.The versatile bonus space offers endless possibilities! Want a home office, guest overflow, art studio, workshop, or your very own private retreat? Step outside and discover the real showstopper: a spacious, lushly landscaped backyard that's practically begging for a sparkling pool 🏊. Whether you envision weekend soirées under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Practical perks? You've got those too. Off-street parking is a rare and treasured luxury in Key West and this property has it. No more circling the block after a long day at the beach. Located just moments from world-famous Duval Street, celebrated dining, vibrant nightlife, the Historic Seaport, and those legendary Key West sunsets 🌅, this property places you at the very center of the island lifestyle while offering a peaceful, private retreat to come home to.✨ Furnished & Move-In Ready, updated, Expansive Backyard with Pool Potential, Off-Street Parking, central Key West Location. If you are searching for a full-time residence, a vacation escape, or a high-demand rental investment, 2005 Fogarty Ave checks

2005 Fogarty Ave, Key West

$889,000

Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, this centrally located residence offers comfortable living just minutes from beaches, shopping, dining, schools, and all that Key West has to offer. The updated kitchen features elegant porcelain countertops, Café appliances, and a newly installed range hood. Recent improvements include a new metal roof (2025) and A/C coils replaced in 2026, providing added peace of mind. An added bonus is the spacious attic, offering valuable storage space--a rare and highly desirable feature in Key West. Step outside to a spacious backyard with mature banana trees, plenty of room to add a pool, and space to create your own private island oasis. A double driveway provides ample off-street parking. Whether you're searching for a full-time residence, a second home, or an investment opportunity, this move-in-ready property offers the perfect blend of comfort, convenience, and island living. Owner is a licensed Florida real estate agent.

3 Beds ⋅ 2 Baths ⋅ 620435 MLS

Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, this centrally located residence offers comfortable living just minutes from beaches, shopping, dining, schools, and all that Key West has to offer. The updated kitchen features elegant porcelain countertops, Café appliances, and a newly installed range hood. Recent improvements include a new metal roof (2025) and A/C coils replaced in 2026, providing added peace of mind. An added bonus is the spacious attic, offering valuable storage space--a rare and highly desirable feature in Key West. Step outside to a spacious backyard with mature banana trees, plenty of room to add a pool, and space to create your own private island oasis. A double driveway provides ample off-street parking. Whether you're searching for a full-time residence, a second home, or an investment opportunity, this move-in-ready property offers the perfect blend of comfort, convenience, and island living. Owner is a licensed Florida real estate agent.

2317 Fogarty Ave, Key West

$3,500,000

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

5 Beds ⋅ 5 Baths ⋅ 620434 MLS

First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West

$799,000

Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the thoughtful floor plan provides comfortable areas for both everyday living and entertaining. The well-appointed kitchen offers ample cabinetry, generous counter space and bar seating that creates a natural gathering place for family and guests. A dedicated laundry area adds every day convenience, while the home's open and functional layout enhances its comfortable coastal appeal. An inviting Florida Room extends the living area and serves as the perfect connection to the private backyard retreat. Step outside to discover your own massive fenced-in backyard designed for relaxation, featuring lush landscaping, a hot tub and plenty of entertaining space. Centrally located in New Town, you'll enjoy easy access to beaches, shopping, restaurants, schools, and all the attractions that make island living so desirable. Whether you're looking for a full-time residence, seasonal escape, or island investment, this Key West home offers comfort, character and an exceptional location.

2 Beds ⋅ 2 Baths ⋅ 620402 MLS

Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the thoughtful floor plan provides comfortable areas for both everyday living and entertaining. The well-appointed kitchen offers ample cabinetry, generous counter space and bar seating that creates a natural gathering place for family and guests. A dedicated laundry area adds every day convenience, while the home's open and functional layout enhances its comfortable coastal appeal. An inviting Florida Room extends the living area and serves as the perfect connection to the private backyard retreat. Step outside to discover your own massive fenced-in backyard designed for relaxation, featuring lush landscaping, a hot tub and plenty of entertaining space. Centrally located in New Town, you'll enjoy easy access to beaches, shopping, restaurants, schools, and all the attractions that make island living so desirable. Whether you're looking for a full-time residence, seasonal escape, or island investment, this Key West home offers comfort, character and an exceptional location.

3715 Flagler Ave, Key West

$1,195,000

Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bedroom, 1-bath residences, each finished with a refined European style kitchen. Clean lines, quality cabinetry, and thoughtful detailing give both sides a fresh, elevated feel while preserving the easygoing island character that makes Old Town so sought after. Each unit lives comfortably and independently, making this an ideal setup for an owner-occupant looking to offset costs, an investor seeking dual income streams, or a buyer wanting a flexible space for family and guests. Private yard space adds room to garden, relax, or entertain under the palms, a true rarity at this address.

2 Beds ⋅ 2 Baths ⋅ 620360 MLS

Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bedroom, 1-bath residences, each finished with a refined European style kitchen. Clean lines, quality cabinetry, and thoughtful detailing give both sides a fresh, elevated feel while preserving the easygoing island character that makes Old Town so sought after. Each unit lives comfortably and independently, making this an ideal setup for an owner-occupant looking to offset costs, an investor seeking dual income streams, or a buyer wanting a flexible space for family and guests. Private yard space adds room to garden, relax, or entertain under the palms, a true rarity at this address.

1126 Grinnell St, Key West

$599,000

Inside the gates of Key West Golf Club -- the only gated golf course community on the island, with an 18-hole Rees Jones course, two pools, a fitness center, and 24-hour security. This pet-friendly, fully-fenced yard, 2-bedroom, 1.5-bathroom Key West townhome sits on a corner lot with on-street parking and guest parking, steps from the mail, pool, and gym. It lives bigger than most: tile through the first floor, sustainable and comfortable cork flooring upstairs, and a permitted balcony enclosure that adds space other units don't have. Covered front porch, two spacious screened porches, In-unit washer and dryer, plus dedicated storage. One owner since new, with a new roof, new A/C, updated kitchen and bathrooms, and full shutter coverage -- move-in ready. Thirty-day minimum rentals permitted. Minutes to the airport, Old Town, the beaches, restaurants, entertainment, and the marinas.

2 Beds ⋅ 2 Baths ⋅ 620312 MLS

Inside the gates of Key West Golf Club -- the only gated golf course community on the island, with an 18-hole Rees Jones course, two pools, a fitness center, and 24-hour security. This pet-friendly, fully-fenced yard, 2-bedroom, 1.5-bathroom Key West townhome sits on a corner lot with on-street parking and guest parking, steps from the mail, pool, and gym. It lives bigger than most: tile through the first floor, sustainable and comfortable cork flooring upstairs, and a permitted balcony enclosure that adds space other units don't have. Covered front porch, two spacious screened porches, In-unit washer and dryer, plus dedicated storage. One owner since new, with a new roof, new A/C, updated kitchen and bathrooms, and full shutter coverage -- move-in ready. Thirty-day minimum rentals permitted. Minutes to the airport, Old Town, the beaches, restaurants, entertainment, and the marinas.

1 Spoonbill Way, Key West

$2,800,000

High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

2 Beds ⋅ 2 Baths ⋅ 620355 MLS

High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

1009 Whitehead St, Key West

$3,800,000

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

3 Beds ⋅ 3 Baths ⋅ 620343 MLS

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

619 Ashe St, Key West

$1,850,000

701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations.

2 Baths ⋅ 620342 MLS

701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations.

701 Simonton St, Key West