Key West Homes with Rain Gutters Exterior features

Key West Homes with Rain Gutters Exterior features

Welcome to Key West, Florida, a tropical paradise that embodies the spirit of island living. Nestled in Monroe County, this vibrant city is renowned for its stunning sunsets, rich history, and eclectic culture. With its charming streets lined with pastel-colored conch houses and lush palm trees swaying in the gentle ocean breeze, Key West offers a unique blend of relaxation and adventure.

As you explore the real estate options in this captivating city, you’ll discover homes that not only capture the essence of coastal living but also feature practical amenities, such as rain gutters. These exterior features are essential in this tropical climate, as they effectively manage rainwater runoff, protecting your investment and enhancing the longevity of your home.

Key West properties often boast outdoor spaces that invite you to soak up the sun, whether it's a spacious porch for morning coffee or a private garden for evening gatherings. Many homes are designed with rain gutters that seamlessly blend with the architecture, ensuring that your home remains both functional and aesthetically pleasing.

Living in Key West means embracing a lifestyle filled with outdoor activities, from snorkeling in crystal-clear waters to enjoying the vibrant nightlife. The community is welcoming, with an array of local cafes, art galleries, and shops that reflect the island's rich heritage.

If you're seeking a home that combines charm, practicality, and the allure of island life, Key West is the perfect destination. Explore the available properties today and take the first step toward your dream home in this enchanting city!

Newest Key West Homes with Rain Gutters Exterior features

1701 Laird St, Key West
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 621910 MLS
Striking contemporary design and total privacy converge in this elevated retreat, situated just moments from Higgs Beach and the White Street Pier. Set behind a distinct pivoting red gate and architectural wall, the home opens to a beautifully curated showcase of natural light and clean geometric lines. The entry foyer--featuring a bright desk nook and a floating open-tread staircase--leads into a living area enclosed by floor-to-ceiling glass and transom windows framing views of the lush grounds. The minimalist kitchen centers on crisp white finishes, custom cabinetry, and premium Bosch appliances, complemented by a stylish glass-door pantry for seamless storage. Designed for privacy, a main-level guest suite is tucked behind a pocket door, providing a self-contained wing complete with an ensuite bath and generous closet space. The entire upper level is reserved for the primary suite, highlighting a spacious walk-in closet and a beautifully appointed ensuite bathroom. Step outside the bedroom onto a private balcony to enjoy an open-air soaking tub set beneath the night sky. Outdoors, mature tropical foliage surrounds the property to create a completely private sanctuary. An expansive heated pool and sunbathing deck form the centerpiece of the backyard, while a covered dining pavilion featuring a built-in grill and counter space makes outdoor entertaining effortless. Tucked to the side, a tranquil Zen garden with a fountain offers a quiet spot to relax. This exceptional residence offers modern luxury and sophisticated living just steps from the ocean.

1701 Laird St, Key West
806 Truman Ave, Key West
$5,365,000
5 Beds ⋅ 6 Baths ⋅ 621899 MLS
Experience the best of Old Town Key West at 806 Truman Avenue, a beautifully appointed transient-licensed residence offering the rare combination of luxury island living and proven rental performance. This distinctive five-bedroom home features approximately 3,223 square feet of living space, thoughtfully designed for both private enjoyment and gracious entertaining. Tropical landscaping, covered porches, a private pool and spa, and separate guest accommodations create a relaxed resort atmosphere with the privacy and character buyers seek in a premier Key West property. Offered furnished, the residence is well suited as a primary home, second home, or high-end vacation rental. The property generated more than $400,000 in rental revenue in 2025, adding meaningful investment appeal to its lifestyle advantages. Situated in the 'X' flood zone, a lower-risk flood designation and outside FEMA's Special Flood Hazard Area. This can be an attractive ownership advantage compared with properties in higher-risk flood zones, particularly when evaluating insurance, flooding potential, and long-term carrying costs. Ideally located in the heart of Old Town, 806 Truman Avenue places owners and guests close to Key West's renowned dining, galleries, entertainment, beaches, and historic attractions. For the buyer seeking a refined island residence with transient-rental capability, established revenue, and exceptional Old Town appeal, 806 Truman Avenue presents a truly compelling opportunity.

806 Truman Ave, Key West
1119 Johnson St, Key West
$5,650,000
4 Beds ⋅ 4 Baths ⋅ 621891 MLS
Discover timeless design and effortless indoor-outdoor living in this custom-built 4-bedroom, 3.5-bath residence in Key West's coveted Casa Marina neighborhood. Completed in 2017, the home blends architectural elegance with comfortable everyday living, surrounded by lush landscaping and lighting throughout. At the heart of the home, a grand living room features soaring ceilings, cove lighting, and expansive NanaWall impact glass doors that open on both sides to both the pool and backyard patio. Designed for entertaining, the outdoor space features a substantial dining area and built-in kitchen. Inside, the kitchen and dining room are thoughtfully separated from the living room by a wall, with two connecting passages providing an easy flow between the spaces. The chef's kitchen showcases semi-precious dumortierite quartz countertops and premium Thermador appliances. A striking powder room features crushed Capiz shell wallpaper, an illuminated onyx sink, and a bronze waterfall faucet. The first-floor primary suite opens to an orchid potting garden on one side and an oversized outdoor shower on the other. Its bath features a private water closet and a six-foot window welcoming natural light. Upstairs, a bedroom or office offers a private terrace overlooking the pools, while two additional ensuite bedrooms share a den complete with a wet bar, and a full-size laundry room From the coral stone entry pathways over interconnected pools to the glass-railed staircase, and espresso Acacia wood flooring, thoughtful details distinguish this home. Additional amenities include a covered carport with a motorized door and EV charging, a whole-house generator, and a heated and chilled pool.

1119 Johnson 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
8 Golf Club Dr, Key West
$849,000
3 Beds ⋅ 3 Baths ⋅ 621697 MLS
Beautifully renovated 3-bedroom, 2.5-bath townhome offering a perfect blend of style, comfort, and outdoor living. The stunning chef's kitchen features custom wood cabinetry, quartz waterfall countertops, and a premium KitchenAid appliance package. Additional interior upgrades include a new central A/C system, wood flooring throughout, two completely renovated upstairs bathrooms, and the addition of a convenient half bath on the main level. Enjoy indoor-outdoor living with screened porches, weather- and UV-protective vinyl blinds on the rear deck, and an expanded backyard patio finished with flagstone pavers. The professionally designed tropical landscape, created by a landscape architect, includes irrigation, landscape lighting, and beautiful stone walkways that transform the entire property into a private island oasis. Additional improvements include impact-resistant windows, no-see-um screening, new gutters, hurricane shutters, and full screening and lattice around the base of the home. The under-house area has been enhanced with access panels, an insect and critter barrier, and additional storage space. Meticulously maintained and thoughtfully upgraded, this exceptional property offers quality craftsmanship and attention to detail at every turn. Every improvement has been carefully considered, creating a move-in-ready home that is as functional as it is beautiful. Please visit KWGCHOA.com for detailed community association information.

8 Golf Club Dr, Key West
813 Thomas St, Key West
$3,895,000
4 Beds ⋅ 3 Baths ⋅ 621693 MLS
Steps From Duval. Worlds Away. Morning coffee on the wraparound porch. An afternoon swim beneath the waterfall. Dinner under the stars. At 813 Thomas Street, every day feels like the best kind of Key West getaway. Set on a rare double lot in Flood Zone X and completely renovated in 2025, this island-contemporary residence pairs a 3-bedroom, 2-bath main home with a brand-new 1-bed, 1-bath guest cottage, giving family and friends a private retreat of their own. Inside, soaring ceilings, sun-drenched living spaces, and hardwood floors set an elegant tone. The chef's kitchen is the showpiece, with custom cabinetry, a sculptural quartz waterfall island, and a full suite of Thermador stainless steel appliances delivering professional-caliber performance with refined style. Whether it's a quiet breakfast or a dinner party for a crowd, this kitchen is ready for it. The entire second floor belongs to the primary suite, with a private balcony, walk-in closet, and spa-style bath featuring a deep soaking tub, double vanity, and separate shower. Impact French doors open to the outdoor living spaces. A motorized pergola covers the alfresco dining area and grill station or opens to the sky at the touch of a button. More than 500 square feet of decking wraps a 15' x 22' heated completely new saltwater pool with a Cosentino Dekton waterfall, surrounded by lush tropical landscaping and an outdoor shower. Gated driveway with off-street parking for two completes this move-in ready offering. The location is pure Old Town: stroll to Blue Heaven for brunch, tour the Hemingway Home and the Key West Lighthouse, catch the sunset at Fort Zachary Taylor, snap a photo at the Southernmost Point, or explore Duval Street and Bahama Village, all within walking distance. Homes like this in the heart of Old Town are rarely available. Schedule your private showing today!

813 Thomas St, Key West
64 Golf Club Dr, Key West
$975,000
3 Beds ⋅ 3 Baths ⋅ 621691 MLS
A rare find! Three bedrooms and three full bathrooms make this lovely golf course residence a standout opportunity. This home offers a comfortable and versatile layout with an updated kitchen and a convenient main level bedroom that can easily serve as a home office or guest room. A full bathroom on the main floor adds even more flexibility. Enjoy the peaceful golf course setting in a great location away from the direct path of golf balls. With its combination of space and a desirable location this is an opportunity you don't see come along often.

64 Golf Club Dr, Key West
1618 South Street, Key West
$4,400,000
4 Beds ⋅ 3 Baths ⋅ 621671 MLS
BRAND NEW CONSTRUCTION MIDTOWN WEST Meticulously crafted by a local luxury builder, this exceptional new 4 bedroom 3 bath residence combines superior construction, thoughtful architectural design and exquisite attention to detail to create effortless tropical elegance. Step inside to soaring 20-foot ceilings, a light-filled open floor complimented by 12'x40' tile flooring. A striking floating staircase with open wood treads adds architectural flair. The gourmet kitchen showcases custom Hanson and Bringle cabinetry, granite countertops and premium stainless steel Thermadore appliances, with a central island and built in wet bar. The second level features two bedrooms with a Jack-and-Jill bath, while the third level offers an expansive mezzanine, with wet bar and luxurious second primary suite with soaking tub and separate shower. Custom white oak flooring, motorized Hunter Douglas Pirouette window treatments and designer lighting reflect the exceptional quality throughout. Designed for seamless indoor-outdoor living, the lush tropical setting features a heated 10' x 20' saltwater pool with six-foot swim-out, outdoor shower and exquisite outdoor kitchen with built-ins, refrigeration and grilling area. Five private porches invite morning coffee, afternoon breezes and relaxed evenings under the stars, buffeted by lushly landscaped grounds. Quality is evident in every detail, from premium Andersen impact-resistant windows and a standing-seam metal roof to Hardie board siding, AZEK trim, extensive closed-cell insulation and dual high-efficiency Mitsubishi A/C systems. A two-car tandem garage completes this thoughtfully designed island retreat, where enduring craftsmanship meets sophisticated tropical luxury in a family friendly neighborhood. Completion date Jan '27. More images to follow. Front image has been digitally created.

1618 South Street, Key West
138 Golf Club Dr, Key West
$580,000
2 Beds ⋅ 2 Baths ⋅ 621596 MLS
VALUE now is even SWEETER! Adjusted Price! Welcome to 138 GC Dr. in the highly sought-after Key West Golf Club residential community. Surrounded by acres of open space, Rees-Jones designed 18-hole Championship Golf Course. INVITING, Ready for Immediate Occupancy, ''Fresh as a Daisy,'' Townhome. Waiting for you! Beautifully maintained home offers the perfect blend of island living, resort-style amenities. Featuring low maintenance ceramic tile downstairs, new Berber carpet upstairs, freshly painted interior/exterior, charming picket fence, abundant natural light, 4 VERANDAS! Ideal for full-time residents, those seeking a relaxing vacation retreat, or utilize your new home intermittently while enjoying 30-day vacation rentals to supplement expenses. Ideal for long-term income producing rental home, as housing demand is great for the hardworking ''locals,'' all while you await retirement. So many options. This home is a short stroll to Golf Pro Shop, Community Center Building w/Fitness Room is just down the lane, a hop-skip-and jump to the beautiful, large lagoon-shaped pool w/tropical waterfalls. There is a real ''spirit of community!'' Peaceful ambiance in end-unit location, providing that extra breathing room. Easy to navigate kitchen has white appliances and Formica countertops. Private outdoor veranda directly off the living room is perfect for entertaining/relaxing. Primary Bedroom has 2 closets and large adjacent private veranda, which overlooks scenic Spoonbill Way. Guest Bedroom has adjacent cozy veranda overlooking the mature tree-lined streetscape w/old fashioned street lanterns. KWGC has gated entry, 24-hr. Resident Serv, 2 fabulous pools, Fitness Rm., Butterfly Garden, so much more. Just minutes from Old Town KW, beaches, marinas, shopping, and vibrant dining options, this home offers the tranquility of a private community, easy access to the excitement KW has to offer. Enjoy picturesque views, gentle tropical breezes w/the unique charm of island living.

138 Golf Club Dr, Key West
1100 Johnson St, Key West
$4,995,000
4 Beds ⋅ 3 Baths ⋅ 621521 MLS
Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

1100 Johnson St, Key West
927 Thomas St Unit 1, Key West
$1,133,000
2 Beds ⋅ 3 Baths ⋅ 621479 MLS
Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

927 Thomas St Unit 1, Key West
317 Whitehead St, Key West
$6,895,000
6 Beds ⋅ 7 Baths ⋅ 621466 MLS
The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West
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