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$1,349,000
2 Baths ⋅ 621255 MLS
Situated in Duval Square along Key West's Duval Street, this approximately 1,592 SqFt commercial property consists of two combined condominium units currently configured as a restaurant. Step inside to a spacious dining area, a commercial kitchen, and an inviting layout designed to accommodate both locals and all of the visitors drawn to Key West each year. Outdoor seating adds to the island atmosphere and gives guests the opportunity to enjoy the tropical surroundings that define the Key West dining experience. For an owner-operator, this is an opportunity to put a new concept into an established restaurant space. For an investor, it offers ownership of commercial real estate in one of the island's most sought-after corridors. Bring your concept, your vision, and your appetite for opportunity to life!

1075 Duval St Unit C1 & C2, Key West
$6,750,000
5 Beds ⋅ 5 Baths ⋅ 621141 MLS
Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment. This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable neighborhoods. Enter through the white picket fence and tropical courtyard to your grand Key West estate, where every detail has been thoughtfully designed. The first floor is set for entertaining, featuring a spacious living area and a chef's kitchen with stone countertops, an oversized island, custom cabinetry, and premium Sub-Zero, Viking, and Wolf appliances. A generous walk-in pantry adds extra storage convenience. The primary suite, also on the ground level, overlooks the pool and boasts a spa-inspired bath with dual showers, a freestanding soaking tub (with air bubble massage) and a large walk-in closet with one of two laundry areas. Outdoors, enjoy your private resort-style backyard with an oversized pool, covered lounge, and outdoor kitchen complete with gas grill, ice maker, and mini-fridge, perfect to grill up those fresh catches or hotdogs for the kids. Sonos speakers throughout set the tone to enjoy a relaxed Key West lifestyle. A floating living room staircase leads to two inviting guest rooms and a full bath. Two additional bedrooms currently serve as offices, each with en suite baths and private entrances, ideal for guest suites, studios, or remote workspaces (one includes a kitchenette). A climate-controlled standalone workshop offers a perfect space for projects, hobbies, or extra storage. Designed for both resilience and comfort, the home includes impact-rated doors and windows, a 30 KW Cummins diesel generator with 500-gallon fuel tank, smart home automation for lighting and shades, and off-street parking for two vehicles.

411 Louisa St, Key West
$750,000
2 Beds ⋅ 2 Baths ⋅ 621130 MLS
Positioned in the coveted X flood zone, this 2-bedroom, 2-bathroom townhome perfectly blends Old Town charm with modern convenience. As one of only two units in an exclusive boutique setting, it provides exceptional privacy just steps from local wellness hubs, neighborhood cafes, and historic sites. The efficient galley kitchen is outfitted with granite countertops and stainless-steel appliances, while the primary suite serves as a tribute to island heritage with historic Dade County Pine. Outdoor living is seamlessly integrated with a classic front porch for morning coffee and a fully fenced rear deck designed for private, starlit dinners. Complete with a transferable A/C warranty, and the flexibility of a primary home or monthly rental, this residence offers an effortless Key West lifestyle.

1004 Watson St Unit 2, Key West
$799,000
2 Beds ⋅ 2 Baths ⋅ 621112 MLS
Welcome to 1422 Catherine Street in The Heart of Key West. Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom. The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new floors and totally updated. Outdoors is a perfect courtyard for dining under the stars or just hanging out and solving all the world's problems. There are also washer and dryer hook ups and an outdoor shower. This home is perfect for full time residents, second home or a great rental property. Call today for your private showing!

1422 Catherine St, Key West
$729,000
2 Beds ⋅ 1 Baths ⋅ 621035 MLS
This performing vacation rental sold as shown is an excellent property which exudes a sense of warmth and character from the moment you set eyes on it. As you approach the home, you are greeted by a picturesque facade that captures the essence of Key West architecture. The vibrant colors and tropical landscaping create a welcoming atmosphere that invites you to step inside and explore further. Upon entering the home, you are immediately struck by the inviting interior filled with natural light and coastal charm. The open layout seamlessly blends the living spaces, creating a perfect setting for both relaxation and entertaining. The home at 906 Truman Ave 1 also boasts a tranquil outdoor oasis, where you can unwind and enjoy the tropical breeze. Whether lounging on the deck or relaxing in the pool, this space offers a peaceful retreat from the hustle and bustle of everyday life. Overall, the home at 906 Truman Ave in Key West is a true gem that combines comfort, style, and the laid-back elegance of island living. It is a place where memories are made and dreams are realized. Professional Vacation Rental Management is available for this property.

906 Truman Ave Unit APT 1, Key West
$2,550,000
4 Beds ⋅ 4 Baths ⋅ 620994 MLS
Welcome to 1202 Royal Street, a beautifully reimagined and rebuilt Key West residence where thoughtful design, modern construction, and exceptional Old Town location come together. Featuring four (4) bedrooms and three-and-a-half (3.5) bathrooms, this property has been rebuilt from the ground up with meticulous attention to detail. Located in coveted Historic Old Town and the highly desirable X Flood Zone, 1202 Royal Street places you in the heart of everything that makes Key West special. Step through the stunning mahogany hurricane-impact front door into a bright interior with soaring ceilings, natural light, and a striking floating staircase leading to the second floor. The home flows effortlessly into an expansive open-concept kitchen and living area designed for both everyday living and entertaining. Open the home to your private backyard, where IPE decking, a heated and chilled pool, and separate hot tub create the perfect indoor/outdoor lifestyle and an ideal setting for entertaining family and friends. The ground-floor primary suite offers privacy from the rest of the home and features a beautiful ensuite bath. Upstairs, two additional bedrooms share a thoughtfully designed Jack-and-Jill bathroom, providing comfortable accommodations for family and guests. The detached guest house, configured as a legal duplex with separate water and electric meters, adds tremendous versatility. Use it as a luxurious pool house, private guest quarters, additional primary suite, or completely separate living space. Additional features include impact windows and doors, spray-foam insulation, IPE decking, two A/C zones in the main residence, ductless climate control in the guest house, fire sprinkler systems in both residences, and numerous additional upgrades throughout. Come experience 1202 Royal Street and discover what it means to live like royalty in Key West!

1202 Royal St, Key West
$3,700,000
3 Beds ⋅ 4 Baths ⋅ 620985 MLS
Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point. Step inside through iconic yellow doors into a bright, sunny retreat defined by historic Dade County pine walls, gingerbread balustrade details, high soaring ceilings, and rich natural light. The main level flows into an open-concept living area and a sleek white kitchen equipped with stainless steel appliances, ample prep space, and an oversized island with seating for six--perfect for gathering family and friends. Designed for indoor-outdoor living, double sliders spill out to a well-appointed, covered lanai featuring a large outdoor TV and a rare air-conditioned half bath. Beyond the lanai lies a private tropical oasis enveloped by lush palm trees and fencing. Take a refreshing dip in the 8' x 14' heated pool with its soothing water feature, lounge in the sunshine on the deck, or host alfresco dinners using the gas grill. The interior layout offers total comfort and privacy for guests. The main floor houses two king-bedroom suites complete with walk-in showers, including one with direct access to the poolside sanctuary. Tucked upstairs for added seclusion, the third ensuite bedroom features a queen bed, vaulted ceilings, and sunny exposure. Completely renovated with impact windows, and dedicated off-street parking, this property is designed for effortless ownership. Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West paradise.

530 Catherine St, Key West
$995,000
2 Beds ⋅ 2 Baths ⋅ 620885 MLS
Completely remodeled to the studs in 2024, this exceptional Key West condo is truly turn-key and move in ready. The home has been meticulously maintained and shows beautifully in every detail. Everything in the unit is new, from the finishes and fixtures to the systems. Central air conditioning and a security alarm are already in place for immediate comfort and peace of mind. This 953 sq. ft.unit features an oversized primary bedroom with a true walk-in closet, a spa inspired -large shower with a waterfall showerhead, and high-end details throughout. An additional 195 sq ft covered front porch expands the living space and is protected by premium motorized electronic screens that raise and lower at the touch of a remote-a significant high end upgrade. Located in a desirable three-unit condo association, the HOA fee covers exterior insurance and water, keeping ownership simple and predictable.. Enjoy classic Key West living with lush tropical landscaping including bamboo and a private heated pool. Super clean, super nice, and ready for immediate occupancy.

1116 Truman Ave Unit A, Key West
$779,000
2 Beds ⋅ 2 Baths ⋅ 620829 MLS
Turnkey Old Town Key West condo! 2 Bedrooms/2 Full Baths/ Fully Furnished/Pool-side/Rentals through March 2027! Welcome to your turnkey piece of Old Town Key West. This first-floor, poolside 2 Bedroom.2 Bath condo is fully furnished, ready to enjoy now, and comes with future rentals already booked through March 2027. Whether you're looking for a Key West getaway or an established vacation rental, this property offers the flexibility to do both. The open and comfortable layout features 2 Bedrooms and 2 Full bathrooms, making it especially appealing for vacation guests, couples traveling together, or personal use. The condo is being sold fully furnished, allowing the next owner to begin enjoying or renting it immediately without the time and expense of furnishing a property. Enjoy your own private covered outdoor living area with grill, wet bar, and seating-perfect for morning coffee, outdoor dining ,or relaxing after a day on the island. The shared pool is just steps away. Inside, you will find central air conditioning ,a washer and dryer, and a mix of tile and wood flooring. A new metal roof and hurricane panels provide additional piece of mind. Located on Truman Avenue in Old Town, you're within easy reach of Duval Street, White Street, the Historic Seaport, restaurants ,galleries, and the best of Key West. Walk or bike to explore the island, then return to your own comfortable retreat. For the investor, the established vacation rental set-up and bookings already in place through March 2027 provide an immediate opportunity for continued rental income. For the owner seeking a second home, this fully furnished condo is ready to enjoy from day one. Two bedrooms, two baths, private outdoor space, pool access and a prime Old Town location make this a truly turnkey Key West opportunity!

906 Truman Ave Unit 2, Key West
$3,180,000
3 Beds ⋅ 3 Baths ⋅ 620747 MLS
Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

1019 Whitehead St, Key West
$3,675,000
2 Baths ⋅ 620701 MLS
Rare chance to own a piece of the most iconic street in the Florida Keys. This turn-key commercial building at 1215 Duval Street is offered at a 7.0% cap rate with a solid, established long-time successful restaurant as the tenant and a lease already in place. (Note: the business is not for sale; the real estate and the income-producing lease are.) Positioned in the heart of Old Town's high-traffic corridor, the property benefits from year-round foot traffic, world-famous Duval Street exposure, and the enduring demand that makes Key West commercial real estate so limited and so coveted. With a dependable tenant and stabilized income from day one, this is a true passive, hands-off investment in one of the strongest small-market commercial locations in the country. Opportunities to acquire well-located Duval Street commercial real estate with an in-place lease and a proven tenant are exceedingly rare. Whether you're a 1031 exchange buyer seeking reliable cash flow or an investor looking to plant roots in paradise, 1215 Duval Street delivers location, income, and long-term upside. Schedule your private showing today.

1215 Duval St, Key West
$539,000
1 Beds ⋅ 1 Baths ⋅ 620692 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a new metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit 3, Key West
$479,000
1 Baths ⋅ 620599 MLS
The time is now to jump into The Key West Commercial investment opportunity in the Heart of Duval Street. This is perfect for you, a fully leased commercial condo to a long standing Key West Tenant, with a proven track record. The office/retail condo is completely upgraded with a completely new AC system - air handlers and ducts. Brand new storefront windows and front door with new aluminum frame impact rated. All floors, walls and paint have all been upgraded.. New lights and drop ceiling. All of the leg work has been professionally done, now just invest and enjoy your returns. Unit does come with one dedicated covered parking spot in the gated garage. The association is professionally managed, and is currently painting the exterior of the buildings. Monthly association dues are coming down and currently 1,554 which does include outside insurance, common area maintenance and exterior building maintenance. This unit is done and ready for you, call today for more details and to set up a showing! Today is the Day! Please do not disturb tenant, thanks! Must sign NDA for all details on the current lease.

1075 Duval St Unit STE C22, Key West
$1,575,000
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
$992,000
3 Beds ⋅ 2 Baths ⋅ 620547 MLS
Old Town 'Diamond in the Rough' near Bay View Park with the highly coveted Off-Street parking. Unique opportunity to acquire a corner lot of over 4,500 sq ft in quiet Old Town neighborhood. Good amount of yard space. No active or expired building permits or code cases. Being sold As-Is with no repair & no clean up. Does have an existing fiberglass pool surrounded by a wooden deck. There is an existing concrete pad behind a double fence that could provide secured off street parking. Side yard is 37 Ft from side of house to fence and 49 Ft wide. Back yard with pool and deck is 27 X 27. Lots of potential. Major renovation project. Probably needs cash buyer. Contract requires court approval due to guardianship. Proof of funds must accompany offer. Create your island oasis at 1119 Florida St.

1119 Florida St, Key West
$1,489,000
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
$999,000
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
$579,000
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
$479,000
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
$569,000
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
$2,385,000
3 Beds ⋅ 4 Baths ⋅ 620437 MLS
Limited time buyer incentive - as an added bonus, the sale now includes a low-mile 2021 Jeep Wrangler Sahara Convertible--giving you the complete Key West lifestyle with the perfect island ride from day one. Welcome to your quintessential Old Town retreat, where classic Key West character has been thoughtfully restored into a warm, inviting home designed for easy island living. This entire property has undergone substantial renovations & a comprehensive transformation. Beautifully reimagined & built for entertaining, the now 3-bedroom, 3.5-bath residence boasts nearly 1,900 sq ft of effortless indoor-outdoor living with every bedroom featuring its own en suite bath including an optional first-floor primary suite. Beneath a magnificent Royal Poinciana tree, the inviting front porch opens to bright, airy living spaces accented by white pine floors and a seamless flow designed for entertaining. The chef's kitchen showcases natural oak shaker cabinetry, Calacatta Miraggio Gold quartz countertops, Bertazzoni appliances, a Dade County Pine accent wall, and timeless finishes that blend warmth with sophistication. French doors lead to a private tropical oasis featuring Ipe hardwood decking, a newly rebuilt saltwater pool and spa, and lush, low-maintenance native landscaping. Upstairs, an expansive wraparound balcony overlooks a mature fruit-bearing mango tree--an unmistakable touch of Old Town charm. Additional highlights include off-street parking, the coveted X Flood Zone, and designer furnishings throughout, allowing for an effortless, move-in-ready experience. Ideally located just one block from vibrant White Street and a short walk or bike ride to the beach, Duval Street, restaurants, galleries, and waterfront attractions, this exceptional property is equally suited as a private island retreat, luxury vacation rental, or full-time residence.

1033 Catherine St, Key West
$3,500,000
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
$1,195,000
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
$2,800,000
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
$1,295,000
2 Beds ⋅ 1 Baths ⋅ 620334 MLS
Welcome home! Charming Old Town Key West Cottage with Off-Street Parking. Situated on a desirable corner lot in Old Town, this 2-bedroom, 1-bath conch cottage offers the quintessential Key West lifestyle. Inside, natural light highlights the home's historic Dade County pine walls and original wood floors, blending timeless character with modern comfort. The updated kitchen and dining area create an inviting space for entertaining, flowing seamlessly into the living room and extending to a private outdoor retreat. Located in the desirable X flood zone, this property combines historic charm, modern updates, and an exceptional location--everything you need to experience the best of Key West living.

1124 Watson St, Key West
$439,000
1 Baths ⋅ 620196 MLS
Lowest price commercial retail space in Old Town! This commercial condominium positioned along high-visibility Truman Avenue, offers an 8% CAP RATE and exceptional exposure amid a dynamic mix of shops, restaurants, and historic attractions. Ideal for retail, professional office, salon, or gallery use. Recent upgrades include new flooring, fresh interior paint, and a renovated bath delivering a clean, turnkey environment ready for immediate occupancy. Benefit from steady pedestrian and vehicle traffic in one of Key West's most established commercial corridors. Schedule your private tour today. Secure your business opportunity in the heart of Old Town Key West. HOA: $576/month -- includes building insurance, exterior maintenance, and common area care.

1012 Truman Ave Unit 6, Key West
$4,550
1 Baths ⋅ 620194 MLS
Prime retail leasing opportunity in the heart of Old Town Key West, just one block from Duval Street. This 805 SF storefront on Simonton Street benefits from exceptional visibility and strong year-round foot traffic from both locals and visitors. Surrounded by restaurants, boutiques, galleries, and lodging accommodations, the space is ideally positioned for a variety of retail, gallery, office, or service-oriented uses. Rare opportunity to secure a presence in one of Key West's most sought-after commercial locations. Base rent only; NNN expenses not included.

601 Fleming St Unit B, Key West
$750,000
2 Beds ⋅ 2 Baths ⋅ 620157 MLS
TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors. Whether you're lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Don't miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location. Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

508 Louisa St Unit 3, 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
$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