Key West Homes with Updated/Remodeled Property Condition

Key West Homes with Updated/Remodeled Property Condition

Welcome to Key West, Florida, a vibrant island paradise nestled in Monroe County, where the sun shines brightly, and the ocean breeze whispers tales of adventure. Known for its stunning sunsets, rich history, and laid-back lifestyle, Key West is a dream destination for those seeking a slice of tropical living.

As you explore this enchanting city, you'll discover a diverse array of homes that beautifully blend modern comforts with the charm of island living. Our listings feature updated and remodeled properties that are perfect for anyone looking to embrace the Key West lifestyle. Imagine waking up in a beautifully renovated home that showcases contemporary design while paying homage to the island's historic architecture. These homes offer the perfect backdrop for your new life, whether you’re looking for a cozy retreat or a spacious family residence.

Key West is not just about picturesque homes; it’s a community rich in culture, art, and outdoor activities. Spend your days wandering through the historic Old Town, indulging in fresh seafood at local eateries, or enjoying water sports in the crystal-clear waters. With a vibrant nightlife and a welcoming community, you’ll find that Key West is not just a place to live—it’s a lifestyle.

If you're ready to make your move to this tropical haven, our updated and remodeled homes are waiting to welcome you. Experience the magic of Key West and find your perfect home in this island paradise today!

Newest Key West Homes with Updated/Remodeled Property Condition

3635 Seaside Dr Unit 205, Key West
$525,000
2 Beds ⋅ 2 Baths ⋅ 621888 MLS
Enjoy the relaxed Key West lifestyle at Salt Ponds, a residential condominium community surrounded by tropical landscaping and a peaceful island atmosphere. This inviting home offers a comfortable setting for everyday living or a seasonal retreat, with convenient access to Key West's beaches, dining, shopping, and Old Town. A welcoming opportunity to enjoy island life in a well-established community. Private carport included.

3635 Seaside Dr Unit 205, Key West
923 Fleming St, Key West
$5,300,000
7 Beds ⋅ 6 Baths ⋅ 621882 MLS
A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

923 Fleming St, Key West
1104 Packer St, Key West
$2,249,000
4 Beds ⋅ 4 Baths ⋅ 621864 MLS
Some places in Key West you visit. This one you call home. 1104 Packer St is a storybook Conch cottage, full of surprises & charm. Inside, a grand foyer & tall ceilings welcome you in, and the home opens with a warmth that feels instantly familiar. Hardwood floors run throughout & original pulley windows nod to the island's history. Enjoy morning coffee or evening sundown from your own front porch. The open living & dining room is wrapped in windows framing your backyard oasis, with vaulted ceilings & natural light in every corner. French doors open to the pool, so gatherings flow easily from table to terrace. The large kitchen, with new Bosch appliances, Viking range & tons of storage, overlooks the pool & living/dining areas allowing the host to be part of the celebration. Step outside & the world softens. The new heated saltwater pool, installed 2026, shimmers beside travertine decking & an undercover porch/lanai, a private sanctuary for long afternoons & quiet evenings. When night falls & the island hushes, stretch out on a lounge chair & count the stars. The large ensuite primary bedroom is a true retreat, with a stunning new bath: two vanities, a classic clawfoot tub for long, quiet soaks & a spa-like shower. A third bedroom/office has a private entrance. Upstairs, a second guest bedroom offers an ensuite bath, & and private ensuite guest cottage keeps visitors comfortable & independent. Recent remodel includes new roof, AC, heated saltwater pool, tankless water heater, refreshed kitchen w/new appliances, & remodeled primary bath. Just arrive & exhale. This private home sits in a quiet, desired location, low risk flood zone only steps from Duval St, restaurants, entertainment & the beach. Old Conch soul, thoughtfully modern, ready to be yours. Come home to 1104 Packer St.

1104 Packer St, Key West
1004 Watson St Unit 1, Key West
$895,000
3 Beds ⋅ 2 Baths ⋅ 621844 MLS
Historic Old Town Key West charm, completely reimagined with the luxury and convenience of modern living. Located in the desirable X Flood Zone, this extraordinary townhome has undergone an extensive, top to bottom transformation. Far more than a visual renovation, the home features under the hood all new plumbing and electric wiring and systems. The beautifully redesigned interiors, contemporary finishes, and thoughtful upgrades throughout makes nearly everything feels brand new. One of only two units, the property enjoys an exceptionally low HOA fee of just $35 per month, covering common area insurance, maintenance, and reserves. Even better, this stunning home is offered fully furnished as shown. Just bring your toothbrush and begin enjoying the island lifestyle on the day of closing. Inside are two inviting bedrooms, two beautifully renovated full bathrooms, and a versatile bonus area with a Murphy bed for guests or a home office. The primary suite features a private ensuite bath, while both bathrooms showcase luxurious tiled walk-in showers and modern fixtures. The completely reimagined kitchen features a Frigidaire refrigerator, THOR gas range, ZLINE microwave, Samsung smart dishwasher, island sink with disposal, GE Profile all-in-one washer/dryer, wine cooler, and beverage cooler. Soaring cathedral ceilings and two expansive skylights fill the living space with natural light. Central air conditioning and a supplemental mini-split provide year-round comfort. Outside, a private tropical retreat awaits, complete with a spacious deck, built-in seating, propane fire feature, string lights, privacy fencing, and full size hot tub. A rare opportunity to enjoy the character of historic Key West with the freshness of a thoroughly reinvented home. Ideal as a primary residence, second home, or potential monthly rental. Completely reimagined, beautifully furnished, and move in ready.

1004 Watson St Unit 1, Key West
115 Front St Unit APT 101, Key West
$2,250,000
3 Beds ⋅ 3 Baths ⋅ 621771 MLS
Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

115 Front St Unit APT 101, Key West
817 Pearl St, Key West
$825,000
1 Beds ⋅ 1 Baths ⋅ 621769 MLS
Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by! Home Owners insurance is $ 1471.58, Flood Insurance is $ 1463.00

817 Pearl St, Key West
2827 Harris Ave, Key West
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 621768 MLS
This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

2827 Harris Ave, Key West
711 Olivia St, Key West
$2,895,000
3 Beds ⋅ 3 Baths ⋅ 621758 MLS
Fully restored historic 3BD/3BA with 1,600 sq ft of total living space in the heart of Old Town, with pool, private guest cottage, and off-street parking, located in X flood zone and offered turnkey. Some historic homes ask their next owners to take on a century of hidden repairs. This one asks only that you move in. With great care and pride, the owner restored the house from foundation to roof: a new foundation, new windows and siding, all-new electrical and plumbing, and every system beneath the surface brought current. The result is the character of an Old Town classic with the soundness of a home built today, and none of the worries that usually come with an older house. Inside, the main house is arranged as a 2BD/2BA, with both bedrooms ensuite, giving each occupant a private retreat of their own. Outside, the pool sets the tone for long winter afternoons in the tropical sun. Beside it, a separate 1BD/1BA guest cottage gives visiting family or friends their own quarters and bath, so everyone can share the season while keeping their privacy. Off-street parking for one car, a true premium in Old Town, makes arrivals and departures easy. The home is offered fully turnkey, with interiors curated by local designer Amie Woeppel, so a seasonal owner can arrive, unpack, and start living, with nothing left to fix or furnish. Every choice reflects an owner who restored this house to be lived in and loved, not simply sold. From the front door, Duval Street is a six-minute walk, with a wide selection of restaurants and bars along the way. Old Town history, rebuilt from the ground up and ready for its next chapter.

711 Olivia St, Key West
3315 Donald Ave, Key West
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 621749 MLS
***Beautifully maintained, thoughtfully improved, and ready for its next chapter in Key West!*** Discover 3315 Donald Avenue, a home where quality, comfort, and island living come together beautifully! Tucked into desirable Buttonwood Court, this inviting 3-bedroom, 2-bath residence offers soaring vaulted ceilings, premier lighting, warm natural wood cabinetry, granite countertops, a spacious kitchen island, and a convenient pantry. The open, welcoming interior flows through sliding glass doors to a screened rear porch overlooking a natural wildlife area. Here, beautiful sunrises greet you from the back of the home, creating a peaceful setting for morning coffee or simply enjoying the natural surroundings. Pride of ownership is evident throughout, with thoughtful improvements, quality finishes, and inviting outdoor spaces designed for easy Key West living. Enjoy the convenience of being just minutes from Old Town's restaurants, galleries, entertainment, and waterfront attractions while returning home to a quieter neighborhood setting. With its appealing combination of location, comfort, and exceptional care, this property presents a wonderful opportunity for locals looking to put down roots or anyone ready to make Key West home. **A home that's been cared for with intention and is ready to be enjoyed from day one!**

3315 Donald Ave, Key West
1320 Eliza St, Key West
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 621742 MLS
Welcome to 1320 Eliza Street, a beautiful historic Key West home filled with Old World charm and character. Once serving as a local schoolhouse, this unique property sits on a stunning, tropically landscaped corner lot in a quiet neighborhood, offering the perfect combination of history and privacy in Old Town, Key West. Featuring four (4) bedrooms, two (2) full bathrooms, and two (2) half bathrooms, this home offers plenty of space for family and guests, both indoors and out. A brand-new roof was recently installed, and the home has just been tented, providing added peace of mind. The main residence offers generous living spaces that open beautifully to the lush tropical gardens surrounding the home. The spacious living room flows directly onto a covered porch, allowing you to enjoy the wonderful Key West weather year-round. The chef's kitchen is perfect for preparing everything from a gourmet dinner to a casual meal with family and friends. The first-floor primary bedroom offers plenty of room for a king-size bed, along with a spacious walk-in closet. The second guest bedroom features its own en-suite bathroom and private front porch, giving guests their own special place to relax and enjoy the Key West lifestyle. Upstairs, you'll find a third bedroom along with an oversized walk-in storage area and ample closet space. Step outside and enjoy your own private tropical retreat. Beautiful gardens surround the heated and chilled swimming pool, creating a wonderful setting for entertaining or simply relaxing in the sunshine. Tucked away in the back corner of the property, the separate pool house offers additional privacy and flexibility, making it perfect for guests, a home office, or a quiet getaway. Complete with a half bathroom and outdoor shower, it offers what we like to call a true Key West bathroom! This home is a must see! Schedule your private showing today!

1320 Eliza St, Key West
410 Louisa St, Key West
$2,649,000
3 Beds ⋅ 3 Baths ⋅ 621735 MLS
Welcome to your private tropical retreat in the heart of Key West! Located on a quiet lane, just one block from Duval Street and a short walk to the Southernmost Point, this beautiful three (3) bedroom, three (3) bathroom home offers the perfect combination of location, privacy, and comfortable island living. Built in 2002 and meticulously maintained, the home features a spacious open floor plan connecting the living room, dining area, kitchen, and stunning outdoor space making it perfect for both everyday living and entertaining family and friends. Beautiful hardwood floors run throughout the home, while the kitchen features granite countertops, stainless steel appliances, and custom cabinetry. Two sets of French doors lead from the dining/living space and offer views of the beautiful backyard pool area. Currently set up as a den/office, the first guest bedroom is on the first floor of the home. Upstairs, the spacious primary suite features a large en-suite bathroom and an impressive walk-in closet. A laundry/utility room is at the top of the stairway landing, and across the hallway is an additional guest bedroom with private en-suite bathroom. With three bedrooms and three full bathrooms, there is plenty of room for family and guests to enjoy their own space and privacy. The backyard is where you will truly appreciate the Key West lifestyle. Surrounded by mature tropical landscaping and fully fenced for privacy, the heated and chilled swimming pool is perfect for enjoying year-round. New Trex decking surrounds the pool, creating a wonderful outdoor space for dining, entertaining, or simply relaxing in the sunshine. This home offers everything you could want in a Key West property: a fantastic Old Town location with driveway parking, a great floor plan, beautiful outdoor living space, and the privacy of a quiet lane, all just steps from the excitement of Duval Street. Call today to schedule your private showing!

410 Louisa St, Key West
3801 Flagler Ave, Key West
$2,229,000
3 Beds ⋅ 3 Baths ⋅ 621725 MLS
Welcome to 3801 Flagler Avenue in beautiful Key West! A stunning home designed for luxury, comfort, and privacy, offering the perfect indoor/outdoor island lifestyle. Situated on an oversized 9,500-square-foot lot, a rare find in Key West, this property features two separate structures, a spectacular two-tier saltwater pool with a tanning ledge and waterfall feature, and beautifully landscaped tropical grounds. The entire property feels like your own private resort. The main residence features one bedroom, one bathroom, a gourmet chef's kitchen, a spacious living area, and a beautiful second-floor loft. The open design and natural light give this home a peaceful, Zen-like feel. The second structure, located above the oversized two-car garage, provides the perfect accommodations for family and guests. Featuring two bedrooms, two bathrooms, and a generous living room, this separate living space offers exceptional comfort and privacy. Your guests will feel right at home while everyone enjoys their own personal space. Built for peace of mind and designed for effortless living, this newer-construction home offers exceptional features, including an elevated design above the FEMA AE-8 flood elevation, a whole-house generator, hurricane-impact windows and doors, and durable Hardi Board siding. Enjoy all the charm and beauty of Key West without the constant maintenance often associated with historic island homes. Step outside and discover your own tropical paradise. The beautifully landscaped grounds and stunning saltwater pool create a resort-style setting perfect for entertaining, unwinding or spending endless days soaking up the Florida Keys sunshine. Luxury, privacy, and convenience come together beautifully at 3801 Flagler Avenue. Owner is a licensed Florida Real Estate Broker. Call today to schedule your private showing!

3801 Flagler Ave, Key West
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