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

606 Grinnell St, Key West
1104 Truman Ave, Key West
$2,290,000
5 Beds ⋅ 4 Baths ⋅ 619930 MLS
MOTIVATED SELLER! Prime Old Town Key West Location with 55 ft of Truman Avenue Frontage and Fantastic Off Street Parking. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with 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. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. 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. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use.

1104 Truman Ave, Key West
1104 Truman Ave, Key West
$2,290,000
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
1504 Flagler Ave, Key West
$1,599,999
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
800 Elizabeth St, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619904 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
1 Golf Club Dr, Key West
$1,350,000
1 Baths ⋅ 619883 MLS
Real estate only. No business included. By appointment only, do not disturb business. This commercial building sits on over 1 acre of land at the entrance to the Key West Golf Club community, just off College Road. Currently configured with large showroom, 7 offices, two separate entrances one ADA compliant full bath and full reception area. Plenty of parking in adjoining parking lot, plus additional parking in rear. (Over 12 spaces) Close to Lower Keys Medical Center and quick access to US 1. The property will be delivered vacant at closing. Seller is a Florida real estate broker.

1 Golf Club Dr, Key West
34 Golf Club Dr, Key West
$839,900
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
1911 Seidenberg Ave, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619758 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West
800 Fleming St Unit Unit C1, Key West
$2,399,000
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
800 Elizabeth St, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619700 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
1320 South Street, Key West
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 619665 MLS
Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in closet, providing privacy and convenience for family and guests alike. The main level is designed for living and entertaining, large open floor plan. An additional bedroom and bath on main floor with a door to the pool/deck area. The chef's kitchen is a standout, equipped with high-end stainless steel appliances including a 48-inch Viking gas range, refrigerator, ice maker, dishwasher, built-in steamer, wine cooler, and rich cherry cabinetry. Additional highlights include: Efficient 2-zone HVAC system, Impact windows and sliding glass doors, Beautiful Tigerwood flooring throughout. The exterior is equally impressive, featuring durable Hardi plank siding for low maintenance, Ipe wood decking, and a private pool surrounded by lush tropical landscaping. The fully fenced yard creates a serene and secluded outdoor retreat. The house also offers two off-street parking spaces, plus ample street parking for guests. A rare opportunity to own a spacious, well-appointed home in a prime location--this one truly has it all.

1320 South Street, Key West
1220 Georgia St, Key West
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 619619 MLS
Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

1220 Georgia St, Key West
810 Carey Ln, Key West
$2,150,000
3 Beds ⋅ 2 Baths ⋅ 619599 MLS
Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush landscaping. Located in the heart of Old Town, you're just moments from dining, shops, and the vibrant local scene, yet enjoy the peace and privacy of a hidden setting. Additional highlights include off-street parking--a rare and valuable convenience in this sought-after neighborhood. Whether you're seeking a full-time residence, vacation home, or investment property, this cottage captures the essence of Key West living. Possible Seller financing. .

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

1017 Angela St, Key West
2805 Flagler Ave, Key West
$874,999
3 Beds ⋅ 2 Baths ⋅ 619565 MLS
This sophisticated residence features off-street parking for two vehicles or a boat and is just a block away from the community boat ramp. Recent upgrades include hardie board siding, acoustic, and hurricane-rated doors and windows. An independent storage shed that offers additional storage space. The backyard provides a serene outdoor area perfect for enjoying the island lifestyle. The focus on high-quality finishes, expansive outdoor living, and an inviting design radiates luxury and comfort, making it ideal for entertaining friends and family. The location provides convenient access to exceptional dining, coffee shops, shopping, as well as recreational amenities such as sports venues and schools. Its proximity to the beach and downtown, coupled with low-maintenance landscaping, enhances its appeal and renders it a perfect choice for embracing the island lifestyle with luxury and comfort.

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

846 Olivia St, Key West
214 Eanes Ln, Key West
$3,300,000
4 Beds ⋅ 4 Baths ⋅ 619548 MLS
Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance--an increasingly valuable feature in today's market. This unique property is configured as two separate units, featuring a main two-story residence and a detached guest quarters, with a combined total of 2,573 square feet of living space. The detached unit is separately licensed and equipped with its own electric and water meters, providing true independence and strong income-producing potential. The main home offers a spacious and functional layout designed for island living. The first floor includes multiple living areas, with a generous living room, separate dining space, family room, and a well-appointed kitchen that opens to outdoor patio and deck areas--perfect for entertaining. Upstairs, you'll find three bedrooms, including a primary suite, along with multiple bathrooms and private balconies that capture the charm of Key West. The detached unit provides a private retreat complete with a bedroom, bathroom, kitchenette, and living space--ideal for guests, extended family, or rental income. Additional highlights include off-street parking for two vehicles, a rare and valuable feature in Old Town, as well as inviting outdoor spaces designed for relaxing and entertaining. Whether you're looking for a primary residence with additional income, a second home with flexibility, or a pure investment opportunity, 214 Eanes Lane delivers versatility and value in one of Key West's most sought-after neighborhoods.

214 Eanes Ln, Key West
3029 N Roosevelt Blvd Unit APT 11, Key West
$679,500
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
1319 Newton St, Key West
$1,750,000
3 Beds ⋅ 2 Baths ⋅ 619504 MLS
Discreetly tucked within the storybook streets of the coveted Meadows, this enchanting Key West residence is a rare expression of timeless elegance and island sophistication. Rich in history yet effortlessly refined, the home invites you into a world where classic Conch architecture meets curated, modern luxury. From the moment you enter, the ambiance is unmistakable--soaring ceilings, warm Dade County Pine, and bespoke craftsmanship create an atmosphere that is both grand and inviting. Every space has been thoughtfully composed, balancing texture, light, and artistry to deliver a home that feels as beautiful as it is livable. Beyond the interiors, a private tropical sanctuary unfolds. Surrounded by lush greenery and designed for complete seclusion, the poolside setting evokes a boutique resort experience. Whether basking in the sun, enjoying the gentle sound of water, or hosting intimate evenings under the glow of ambient lighting, this outdoor retreat is nothing short of extraordinary. The upper-level primary suite offers a serene escape, complete with its own sitting area and a covered balcony that captures the essence of relaxed island mornings and golden-hour evenings. Guest accommodations are equally inviting, offering comfort, privacy, and flexibility for hosting family or discerning visitors. Offered turnkey, the home presents a seamless opportunity for immediate enjoyment--whether as a private coastal retreat or a high-performing luxury rental. Every detail has been considered to ensure effortless living without compromising character or authenticity. Just moments from the vibrancy of Old Town, yet worlds away in feel, this is a residence that embodies the true spirit of Key West--elegant, intimate, and undeniably captivating.

1319 Newton St, Key West
3034 Riviera Dr, Key West
$3,398,000
3 Beds ⋅ 4 Baths ⋅ 619475 MLS
Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled canal frontage, complete with a new 24k lb boat lift and ~58' of new seawall, offering seamless ocean access. Step inside to experience the spacious living areas, illuminated by tons of natural light, with tile flooring throughout. Marvel at the attention to detail in the updated kitchen featuring a waterfall island and all new stainless steel appliances. Outside, a heated salt pool, equipped with automation and a water feature, invites you to unwind amidst the lush turf and enchanting landscape lighting. Relish in unparalleled privacy with a comprehensive privacy wall and fencing, enhanced by a Mosquito Nix system for a pleasant outdoor experience. Enjoy the added conveniences of a whole-house automatic generator and on-demand gas water heater. Nestled in an environment that offers the best waterfront living, your lifestyle is enhanced by limitless opportunities for boating and fishing--right from your backyard: automatic front gates, circular driveway, and awning-covered parking round out this unparalleled offering. Elevate your life with this matchless blend of luxury and oceanic freedom!

3034 Riviera Dr, Key West
224 Golf Club Dr, Key West
$875,000
2 Beds ⋅ 3 Baths ⋅ 619444 MLS
Stylish ''Spa'' home within the enclave of The Sanctuary of the Key West Golf Club. An open floor plan greets you to this light filled home that overlooks a private backyard oasis with dip pool, covered brick patio and maintenance free yard. Thoughtful kitchen updates including sleek quartz countertops with waterfall edge, stainless appliance package and new island lighting. The upstairs enjoys 2 spacious bedrooms each with renovated ensuite bathrooms. Spacious covered porches off of 1st and 2nd floor and deeded carport complete this carefree tropical retreat!

224 Golf Club Dr, Key West
1213 Truman Ave Unit A, Key West
$3,900
1 Baths ⋅ 619434 MLS
Old Town Professional Space available in excellent location on Truman Ave / US-1 directly across the street from the Harvey Government Complex. Four rooms comprising approximately 1020SF and attic storage space 540SF. Private bathroom and a shared parking space. Tenant pays for electricity, water, and the Waste Management trash account.

1213 Truman Ave Unit A, Key West
1320 6th St, Key West
$2,200,000
5 Beds ⋅ 4 Baths ⋅ 619406 MLS
Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units, each offering great rental income potential. Your chance to make money and have a home in paradise. Newly remodeled kitchen in the rental home. Enjoy the large inviting pool and well-maintained grounds, all just minutes from downtown Key West. Whether you're looking for a lucrative rental property or a versatile family compound, this unique property is a perfect choice. Don't miss your chance to own this gem in the heart of Key West! Prime Corner Lot enjoy the benefits of a corner lot with enhanced privacy and curb appeal. The property has ample parking and features a three-vehicle covered carport, along with additional off-street parking that can accommodate your boat or RV. The layout and landscaping provide a sense of seclusion, ensuring a comfortable living experience for tenants. This multi-family property is a rare find, combining practicality, privacy, and profitability. Don't miss out on this outstanding investment opportunity!

1320 6th St, Key West
1109 Stump Ln, Key West
$2,199,000
3 Beds ⋅ 4 Baths ⋅ 619404 MLS
On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

1109 Stump Ln, Key West
68 Merganser Ln, Key West
$648,900
2 Beds ⋅ 2 Baths ⋅ 619363 MLS
Beautifully finished, lovingly maintained, and fully furnished 2-bedroom, 1.5-bath townhome in the Key West Golf Club. Situated at the end of the cul-de-sac, in the most convenient location of the golf club, this home is easy to access and provides plenty of parking. The end-unit gives additional privacy and natural light, along with a screened-in wraparound porch surrounded by lush landscaping to extend your entertaining space outdoors. Inside, the cheerful home welcomes you with thoughtfully selected furnishings that maximize the space, fresh, tropical paint colors, as well as updated floors, kitchen, and bath. The first floor is an open floor plan with half bath, kitchen, dining area and living room that opens to the covered porch. The second floor has two bedrooms and a full bath. This location in the community provides plenty of off-street parking for you and your guest, right outside the door. Residents of this gated community enjoy 24-hour security, a fitness center, walking paths, clubhouse, and two resort-style pools.

68 Merganser Ln, Key West
912 James St Unit 2, Key West
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 619306 MLS
Tucked away in the Historic Seaport District, this unique three-bedroom, two-and-a-half-bath condo offers privacy, charm, and flexibility in an exceptional location. Set behind a gated rear entry, the property features a private pool, deck, and lush mature tropical landscaping. The main cottage includes a spacious primary suite with en suite bath, inviting living and dining spaces, a large kitchen, and laundry. A separate guest cottage offers two additional bedrooms and a full bath. Just moments from dining, shopping, and more, this is a wonderful opportunity for an island home, guest retreat, or rental investment.

912 James St Unit 2, Key West
1019 Eaton St, Key West
$1,799,000
3 Beds ⋅ 2 Baths ⋅ 619235 MLS
Tucked within the charm of Old Town Key West, this historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the island's most recognized destinations. Set on a deep 4200+ square foot lot stretching from Eaton Street to Thompson Lane, the property offers 3 bedrooms and 2 baths in a setting designed for both everyday living and relaxed entertaining. Recognized as a 2016 Preservation Award Winner, this lovely home reflects thoughtful preservation of its architectural style while incorporating modern updates. Inside, a light-filled living area, and a main-level primary bedroom create a comfortable and functional layout. The open design flows naturally to the outdoor spaces, while the updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, tile backsplash, and dedicated prep space, along with additional storage and an interior laundry area. French doors extend the living space outward to a covered deck and courtyard. The outdoor setting is a defining element of the home, centered around a private heated pool, covered lounge area and outdoor bathroom. Gorgeous palms and lush plantings frame the backyard, creating a private garden atmosphere with brick walkways and a spacious courtyard for dining and gathering, while string lighting enhances the space for evening ambiance. The deep lot includes off-street parking with a brick-paved driveway accessed from Thompson Lane, a valuable feature in Old Town. Just moments from the Historic Seaport, Duval Street, and some of Key West's most loved local spots, this location provides convenient access to dining, shopping, and live entertainment. With its combination of location, outdoor living spaces, and off-street parking, this property presents a compelling opportunity for use as a primary residence or vacation home in Old Town Key West..

1019 Eaton St, Key West
2330 Staples Ave, Key West
$999,000
1 Beds ⋅ 1 Baths ⋅ 619196 MLS
Discover a rare investment opportunity in the heart of Key West. This spacious corner duplex lot at 2330 Staples St and 1428 6th St offers incredible potential with two separate addresses and alley access for three convenient side entrances. The large lot features a charming, spacious cottage complete with a full kitchen, a bedroom with ample closet space, a stylish bathroom, and an attached garage--perfect for comfortable living or rental income. The second unit has been demolished, providing a blank canvas to rebuild your dream home or expand your investment portfolio. Alternatively, you can choose to demolish the existing cottage and build two brand-new units on this generous lot. Mature landscaping surrounds the property, offering privacy and a serene atmosphere. With two separate ROGOs ready to go and the Staples side of the lot free from flooding, you can start building immediately. Don't miss this unique chance to own a versatile property in a prime Key West location with endless possibilities. Whether you're looking to renovate, rebuild, or develop, this property is your gateway to maximizing value and enjoying the vibrant lifestyle of Key West. Act now and make this exceptional property yours!

2330 Staples Ave, Key West
564 Porter Ln, Key West
$1,350,000
2 Beds ⋅ 3 Baths ⋅ 619140 MLS
President's Walk townhome in the Truman Annex. This is a two-bedroom, 2.5-bathroom unit that also includes a deeded carport. It is a great location close to the community pool and all the downtown attractions that Key West has to offer. It features an open floor plan with kitchen, half bath, dining and living areas that open to the rear and side yard! Upstairs are two-bedroom ensuites with vaulted ceilings and each with their own private bath and porches. The windows and doors are combination of wood and impact. It has a non-transient rental license that allows monthly or longer rentals.

564 Porter Ln, Key West
25 Kingfisher Ln, Key West
$750,000
2 Beds ⋅ 3 Baths ⋅ 619138 MLS
Tucked away on a quiet private cul-de-sac in the highly sought-after Key West Golf Club community, 25 Kingfisher Lane offers a rare blend of privacy, convenience, and island charm. With easy parking and an exceptional setting, this light-filled residence stands out from the rest.This beautifully positioned home features an expansive wraparound deck, larger than most, along with additional windows that flood the interior with natural light. Located within a gated community, it perfectly captures the essence of relaxed island living. Enjoy tranquil golf course and lagoon views from the back porch, an ideal spot for morning coffee or unwinding in the evening breeze. The open-concept living and kitchen area flows seamlessly to the outdoor spaces, creating a perfect setting for entertaining or simply relaxing in peaceful surroundings.Offering 2 bedrooms and 2.5 baths, the upstairs layout includes two en-suite bedrooms, providing comfort and privacy for residents and guests alike. The oversized side yard adds valuable outdoor space that is ideal for lounging, gardening, or enjoying the Florida sunshine. Residents of the Key West Golf Club community enjoy resort-style amenities, including a lagoon-style pool, a second neighborhood pool, fitness center, on-site management, and 24-hour gated security.Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, this home delivers the perfect combination of comfort, lifestyle, and classic Key West appeal.

25 Kingfisher Ln, Key West