Key West FL Real Estate, Homes with Pool for Sale

4 Beds ⋅ 4 Baths ⋅ 620913 MLS

Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island--a unique feature in the community. For the ultimate convenience, a private elevator services all four floors of the home, transporting you from the air-conditioned two-car garage to the spectacular rooftop terrace where you can view daily sunrises over the Historic Key West Marina and sunsets over Mallory Square, both a very short walk away. The top floor features a rare full bathroom and a flexible bonus room ideal for a home office or guest suite. Whether you're mixing drinks at the custom wet bar or lounging on the terrace, this level serves as the ultimate private retreat for taking in breathtaking panoramic views. Peace of mind is built into the architecture with full impact-rated windows and doors and a durable metal roof, ensuring the home is as secure as it is beautiful. The third floor has two primary bedrooms featuring large walk-in closets and balconies. The lifestyle offered here is unparalleled, situated just one block off the vibrant energy of Duval Street. You are steps away from the island's best dining and boutiques, yet you can retreat instantly to the quiet security of a gated community. Spend your afternoons lounging by the large tropical community pool and cabana area, enjoying a level of comfort and convenience unsurpassed in the heart of Old Town. With a rare two-car garage and an unbeatable location, this residence captures the very best of the Florida Keys lifestyle.

119 Simonton St, Key West

$625,000

1 Beds ⋅ 1 Baths ⋅ 620905 MLS

Positioned directly across South Roosevelt Boulevard from Smathers Beach, it blends high-end modern finishes with expansive views of Key West's tranquil salt ponds. Interior highlights and upgrades include Carrara marble surfaces installed in both the kitchen and bathroom a wet bar, tiled floors flowing seamlessly throughout all living spaces, impact-resistant glass windows and doors for ultimate peace of mind. Other feature include large, covered private balcony capturing views of the salt ponds and the surrounding landscape, assigned parking with storage locker, and so much more. Resort-Style community amenities include a spacious, heated saltwater swimming pool, adjacent hot tub, and full-size tennis/pickleball courts, access to the resident clubhouse, dry saunas, and common area lounges. Other conveniences include barbecue area, EV charging station and a car wash. Make La Brisa your home today.

1901 S Roosevelt Blvd Unit 407N, Key West

$1,025,000

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

$2,475,000

3 Beds ⋅ 3 Baths ⋅ 620879 MLS

Experience the best of waterfront living at 3206 Riviera Drive, a beautifully updated canal-front home offering 60 feet of waterfront, exceptional privacy, and direct access to the Key West boating lifestyle. With no homes across the canal, the property enjoys peaceful water views and a uniquely private setting. Designed for both everyday living and entertaining, the open-concept interior is filled with natural light and seamlessly connects to the outdoors through a wall of impact-rated sliding glass doors. The chef's kitchen features premium cabinetry, a large center island, and a waterfront dining area overlooking the pool and canal. The home offers three spacious bedrooms, including two en-suite bedrooms, three full bathrooms, a dedicated laundry room, two-zone air conditioning, and a whole-home generator. Outside, the tropical backyard is built for enjoying the Keys. Relax by the newly renovated heated pool, entertain from the outdoor kitchen, unwind on the screened patio, or enjoy the convenience of an outdoor bathroom. Shell stone limestone walkways, lush landscaping, covered parking, and a fully gated lot complete this private waterfront retreat. Offering the perfect combination of luxury, comfort, and functionality, 3206 Riviera Drive is move-in ready and seller financing may be available.

3206 Riviera Dr, Key West

$849,900

2 Beds ⋅ 2 Baths ⋅ 620877 MLS

Coastal Living at Its Finest - 2-Bedroom Condo at La Brisa ! Wake up to ocean breezes in this beautifully appointed 2-bedroom, 2-bathroom condo located just steps from Smathers beach. Situated directly across the street from the shoreline, this bright and airy residence offers the perfect blend of comfort, convenience, and coastal charm. Inside, you'll find a spacious open-concept living and dining area filled with natural light, a modern kitchen , and two generously sized bedrooms with ample closet space. The primary suite features a private en-suite bathroom, while the second bedroom is ideal for guests or a home office. Relax on your private balcony with peaceful Salt Pond views, or take a short stroll across the street to sink your toes in the sand. This condo also offers amenities such as assigned parking, in-unit laundry, and access to a community pool, tennis courts and clubhouse. Perfect as a primary residence, weekend retreat, or investment property--this is beachside living made easy! Call for your private tour today !

1901 S Roosevelt Blvd Unit 104N, Key West

$2,350,000

6 Beds ⋅ 6 Baths ⋅ 620852 MLS

Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

287 & 289 Golf Club Dr, Key West

$800,000

2 Beds ⋅ 2 Baths ⋅ 620829 MLS

Old Town First floor 2 Bedroom, 2 Bath condo, pool side!. Low HOA- $600 a month/ $1800 a quarter. Great Old Town location, close to Restaurants, '' Walk on White' , Grocery store, and a short walk or bicycle ride to Duval street. This wonderful 2 bedroom, 2 bath condo is one of 4 units and is located steps from the shared pool. Unique to this condo is an outside covered area with a Grill, wet-bar, and seating, exclusively for use with this condo only. Additionally, this condo also has its own washer and dryer. This condo is in a Rental Program, please call listing agent for details. Being sold furnished. This Building has a new roof, and hurricane panels.

906 Truman Ave Unit 2, Key West

$670,000

2 Beds ⋅ 2 Baths ⋅ 620825 MLS

Let 101 Golf Club Drive be the key to your slice of paradise! This home is nestled mid-way in the Key West Golf Course Community which is gated with manicured lush vegetation, pools, fitness center, and a club house. From the home, the back faces unobstructed views of the 1st Fairway, while the front faces the quaint, white picket fence lined drive. Upstairs, each bedroom has its own bathroom and balcony, providing privacy to you and your family or guests. No need to make upgrades as new stainless steel appliances, hot water heater, flooring, & paint are throughout! The home has also been recently tented with warranty, giving an additional peace of mind your home is protected. Whether this is your full time home, vacation property, or investment, 101 Golf Club Dr is move in ready for you to start enjoying the Key West lifestyle!!

101 Golf Club Dr, Key West

$649,000

2 Beds ⋅ 2 Baths ⋅ 620820 MLS

There are homes that simply check the boxes--then there are homes that immediately feel like ''home.'' Tucked on a quiet, 1-way lane w/in Key West Golf Club, 19 Spoonbill enjoys a superbly tranquil setting overlooking the lush, colorful Butterfly Garden/pond. The pace seems to slow. From the newly built composite rear veranda/rear steps, the gentle trickle of water from the Butterfly Garden statue becomes part of the soundtrack. Tropical greenery creates a peaceful backdrop for morning coffee/afternoon relaxation/evening glass of wine. Exceptional Location. Community Center/Fitness Room/HOA Office are just steps away, while the spectacular lagoon-shaped community pool w/tropical waterfalls is only a short stroll through the garden or down the inviting lane. Everyday living feels a little more like a Key West escape. Inside/out, this pristine residence has been given an extraordinary level of care. Freshly painted throughout, the home is sparkling, warm & inviting! For the homeowner seeking a property where the hard work has already been done, this one is the answer. Impressive exterior renovation. The entire front fence/gate has been meticulously rebuilt, posts/pickets re-secured w/ stainless-steel fasteners, 5 new pressure-treated wood panels. Front lower veranda has been completely rebuilt, enhanced w/new composite picture framing, rich English Walnut composite decking/new stair stringers, posts wrapped in composite sleeves/new composite railings. Upper belt/trim on the front/rear replaced w/Azek, secured w/stainless fasteners. Side/rear fencing was carefully re-secured, new pickets/new gate added. Freshly painted white trim/soffits/gutters/rails/balusters complete the polished exterior presentation. 4 brand-new stainless Frigidaire Gallery Series appliances. Wainscoting accented stairwell/rich wooden stairs/flooring upstairs, 2 glorious upper verandas, new lighting fixtures, 2021 AC, tented in 2018/continued Orkin treatment plan, solar lighting. LOOK NO FURTHER

19 Spoonbill Way, Key West

$1,400,000

4 Beds ⋅ 2 Baths ⋅ 620808 MLS

This one is a must see! Spacious 4 bedroom, single family in the 'Pearlman Heights' neighborhood of New Town KW that has undergone recent renovations-upgrades. New roof, kitchen, windows (impact rated), on demand water heater, pool pump, Central AC condenser / air handler, light fixtures, ceiling fans, crown molding, interior doors & more. Nice set up for enjoying the KW weather or entertaining because the den, kitchen & dining areas flow out to the pool deck with 32 fl long in ground pool. No interior step downs or tripping hazards. Located on a one-way street with green dividing median on 17th St. Carport covers the off-street parking space plus additional on street parking. Has an exterior 15 X 7 storage / laundry room. Convenient location close to schools, medical offices, grocery stores & shopping, dining, etc..

1105 17th St, Key West

$12,500,000

6 Beds ⋅ 7 Baths ⋅ 620770 MLS

A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

32 Sunset, 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

$4,499,999

3 Beds ⋅ 3 Baths ⋅ 620745 MLS

Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

1500 Atlantic Blvd Unit 308, Key West

$599,000

1 Beds ⋅ 1 Baths ⋅ 620722 MLS

Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the privacy and simplicity of low maintenance island living. Inside, this 1 bedroom, 1 bathroom condominium feels bright, comfortable, and welcoming. The open living spaces flow naturally to two private outdoor decks, one at the front of the home that is perfect for enjoying the neighborhood atmosphere and another tucked just off the bedroom, surrounded by mature tropical landscaping for a more private escape. The community itself offers the amenities that make everyday living feel like a vacation, including a beautifully maintained heated swimming pool set among lush tropical grounds. An assigned off street parking space and a spacious locked storage area provide conveniences that are increasingly valuable in Key West. Located just 4 blocks from Duval Street, you can easily walk or bike to beaches, restaurants, galleries, shopping, and everything that makes island life so special, while still returning home to one of the quieter residential pockets of Old Town. Whether you are searching for a full time residence, a seasonal retreat, or simply a place where life naturally slows down, 816 South Street, Unit 4 offers an opportunity to experience the very best of Casa Marina living.

816 S St Unit 4, Key West

$2,089,000

3 Beds ⋅ 3 Baths ⋅ 620712 MLS

1706 Seminary Street delivers the space, flexibility, and outdoor lifestyle that can be surprisingly difficult to find in Key West. Set behind a new privacy fence on an expansive 7,480SF lot, the home is near an impressive collection of beautifully maintained and upscale residences, adding to the appeal of this desirable neighborhood. This completely renovated 3 bed, 3 bath home offers nearly 2,000SF of beautifully updated living space, including a versatile third bedroom with its own private entrance, ideal for visiting friends and family, a private home office, or potential rental use. At the heart of the home is a striking new kitchen featuring quartz waterfall countertops, custom cabinetry, new KitchenAid stainless steel appliances, and an open design that connects naturally to the surrounding living spaces. One of the home's most inviting spaces is the glass windows surrounding the family room, where abundant natural light and views of the tropical backyard create a connection to the outdoors. Outside is where this property truly comes into its own. Meandering pathways weave through lush tropical landscaping and connect multiple areas designed for enjoying the Key West lifestyle. A resort style L shaped lap pool anchors the backyard, complemented by 2 covered lounging areas, a Bahama inspired outdoor dining space, an outdoor shower, and a secure storage shed. Along the side of the property, another unique opportunity awaits. With a modification to the existing fence, there is potential for approximately 20ft of covered boat storage, an increasingly valuable feature for anyone looking to keep their boat protected from the Key West sun and weather. Private, beautifully renovated, and designed to make the most of its generous lot, the property offers a rare combination of indoor comfort, outdoor living, and everyday functionality. Whether enjoyed as a primary residence or an island retreat, everything is already in place to start living the Key West lifestyle.

1706 Seminary St, Key West

$995,000

2 Beds ⋅ 2 Baths ⋅ 620697 MLS

Embrace the laid-back lifestyle of the Florida Keys in this waterfront two-bedroom, two-bathroom condominium with beautiful water views. Soaring vaulted wood-beamed ceilings, a skylight, and expansive sliding glass doors fill the home with natural light while showcasing the sparkling water beyond. The open-concept living and dining areas flow seamlessly to a spacious wraparound balcony, creating the perfect setting to enjoy your morning coffee, entertain guests, or unwind with the island breeze. The functional kitchen opens to the main living area, making entertaining effortless. Located in Bay Villas, a boutique waterfront community of just nine residences, residents enjoy beautifully maintained grounds, a community pool, and inviting waterfront gathering spaces. Whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity, this waterfront retreat offers the relaxed charm that makes the Florida Keys so special.

32 Hilton Haven Rd Unit APT 5, Key West

$550,000

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

$499,000

2 Beds ⋅ 2 Baths ⋅ 620690 MLS

Welcome to this beautifully updated condo at 3930 S. Roosevelt Blvd. #N108, offering the perfect blend of comfort, convenience, and island living. Overlooking the sparkling community pool, this inviting residence features a tastefully remodeled kitchen with modern finishes, newer flooring throughout, and a bright, open living space designed for easy living and entertaining. Enjoy your morning coffee or evening cocktail with relaxing pool views, while the covered parking bay provides the added convenience and protection every Key West homeowner appreciates. Residents also enjoy outstanding community amenities, including a newly completed state-of-the-art fitness center, adding even more value to this desirable complex. Located just minutes from beaches, shopping, dining, and Old Town Key West, this move-in-ready condo is ideal as a full-time residence, vacation getaway, or investment property. Don't miss this opportunity to own a beautifully updated piece of paradise in one of Key West's most desirable locations. Call today to set up your showing. Very easy to show

3930 S Roosevelt Blvd Unit N108, Key West

$499,000

2 Beds ⋅ 2 Baths ⋅ 620689 MLS

This bright, private 2BR/2BA corner unit sits at the end of the west wing, with an extra window that fills the space with light and only one shared wall for real quiet. This unit comes with covered parking. The kitchen is outfitted with stainless steel appliances, and a full-size washer and dryer means laundry day never means leaving home. A covered parking space (#122) comes with the sale. Las Salinas Condominiums is one of the best-kept communities in Key West, and it shows. The pool is sun-drenched and inviting, and the fitness center may be the best on the island, with private access to cardio and strength rooms that are always spotless and always stocked with quality equipment. Monthly fees of $535 cover building insurance, exterior maintenance, and full on-site management, so ownership here is refreshingly hands-off. Step outside and you're close to a grocery store, a day spa, and a bus stop for easy island transportation. Just past the entrance, the two-mile Smathers Beach promenade is calling, whether that's a sunrise walk, a bike ride, or a spot to watch the sky change color every evening. Add in open-lot parking for a second vehicle, plus storage and bicycle rooms, and this is a home built for the way you actually want to live in Key West. Call today to schedule a private showing.

3930 S Roosevelt Blvd Unit W314, Key West

$1,800,000

4 Beds ⋅ 3 Baths ⋅ 620682 MLS

Wonderful Old Town Meadows home with 4 Bedrooms, 3 Baths, on a nearly 5000 sq ft lot, this property has a separate Guest Cottage, wrap around front porch, lap- pool, and more! Wood flooring throughout, with 2 living areas leading to the kitchen with Italian designed built in cabinetry . The Primary Bedroom is spacious, and has built-in Custom cabinetry. Steps from the kitchen is a lap pool , extensive decking, and lots of room for outside dining and relaxation. The Guest Cottage has a full bathroom, and exposed beam ceilings. The property is completely fenced and feels very private.There is a curb cut already- for potential off street parking. Buyer to verify!

1407 Petronia St, Key West

$1,099,000

2 Beds ⋅ 3 Baths ⋅ 620653 MLS

One of the greatest luxuries in Key West isn't extravagance--it's finding a home where life feels a little quieter, a little easier, and a little more connected to the island around you. That's exactly what you'll find at 97 Seaside North Court. Tucked inside the often-overlooked gated Seaside Residences community, this light-filled townhome offers something increasingly difficult to find in Key West--privacy, space, and a sense of calm.Natural light pours through eight additional windows found only in some end units, while mature palms and established mahogany trees create a backdrop of green from every room. Whether enjoying a quiet morning coffee, working from home, or entertaining friends, the four opposing balconies welcome the island breezes and connect the home to its peaceful surroundings. Built with solid masonry construction, impact-rated windows and doors, 16 solar panels paired with a Generac battery storage system, and an elevator that services every floor, this home was designed with comfort, durability, and resilience in mind. The ground-level screened enclosure with a garden offers exceptional flexibility as a home gym, yoga studio, covered dining area, or entertaining space.Residents enjoy a secure, well-maintained community with resort-style amenities including a swimming pool and fitness center, all within easy reach of Smathers Beach, Key West's longest stretch of sandy beach. Built in 2005 on a larger-than-average lot, with 1,824 square feet of air-conditioned living space, three full baths, an outdoor shower, garage, and even a rooftop stargazing deck. 97 Seaside Court North is now offered at an exceptional value within Seaside Residences--an opportunity to enjoy one of Key West's most desirable gated communities without compromising on space, quality, or lifestyle.

97 Seaside N, Key West

$450,000

2 Beds ⋅ 2 Baths ⋅ 620647 MLS

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

3312 N Northside Dr Unit 607, Key West

$4,995,000

4 Beds ⋅ 5 Baths ⋅ 620618 MLS

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat with private interior elevator accessing all floors . Completely reimagined, this one-of-a-kind residence showcases exceptional craftsmanship, sophisticated design, and effortless waterfront living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living areas, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the home is designed for both everyday living and grand-scale entertaining. An oversized island anchors the chef's kitchen, complemented by custom European-style cabinetry, premium quartz countertops, and an impressive suite of appliances including a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker and wine refrigerator, and Perlick refrigerator/freezer drawers. The inviting family room features an electric fireplace and a custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry, creating an ideal space for entertaining. Throughout the home, travertine flooring, custom built-ins, abundant hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, HVAC systems, 12 hurricane-rated sliding glass doors, and a whole-house generator. The luxurious primary suite features a custom walk-in closet, while every bedroom enjoys private balcony access. A guest suite features a zero-entry shower, offering added comfort and accessibility. Beautifully tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance everyday living. Residents enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West

$1,350,000

4 Beds ⋅ 5 Baths ⋅ 620612 MLS

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

1503 Atlantic Blvd, Key West

$375,000

2 Beds ⋅ 1 Baths ⋅ 620584 MLS

NEW LISTING! The Santa Clara condominium in Key West offers gated access, pool, tennis court, and parking. This fifth-floor unit has been recently renovated, featuring new flooring and an updated kitchen with beautiful countertops and stainless-steel appliances. Both bedrooms are generously sized, with the primary bedroom featuring a spacious walk-in closet. You can enjoy sunset views from your private balcony. Condo has onsite management and a laundry room is available on each floor. The property is centrally located near dining, schools, and shopping. It is ideal as a starter home or an investment opportunity.

3312 Northside Dr Unit APT 504, 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

$1,199,000

2 Beds ⋅ 4 Baths ⋅ 620515 MLS

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

33 Seaside S Ct, Key West

$725,000

1 Beds ⋅ 1 Baths ⋅ 620493 MLS

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

308 Margaret St Unit 3, Key West

$1,699,000

3 Beds ⋅ 4 Baths ⋅ 620477 MLS

Experience the best of Key West living at 809 Washington Street #102, located in the exclusive Casa Marina neighborhood. This exquisite 3-story townhome offers a 3-bedroom, 3.5-bath residence (sleeps 8-10) showcasing nearly 1,800 sq ft of sophisticated island style, featuring high-end finishes, bright open living spaces, a gourmet kitchen with stainless steel Viking appliances, seamless indoor-outdoor living, and one deeded parking space. Relax in your own private tropical oasis, complete with a heated pool and lush landscaping, perfect for entertaining and unwinding in paradise. With only a short walk to the beach, restaurants, famous Duval Street and entertainment, 809 Washington offers the perfect blend of island luxury and walkable Key West living and adventures.

809 Washington St Unit # 102, Key West

$1,850,000

2 Beds ⋅ 2 Baths ⋅ 620470 MLS

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

1115 South Street, Key West

$899,995

2 Beds ⋅ 2 Baths ⋅ 620468 MLS

Enjoy the view of the Salt Ponds & catch sunset from the balcony of this 2 bedroom / 2 bath Transient Licensed condo. Good investment opportunity to have your own place in Key West and generate rental income when you are not here to offset carrying costs. The condo comes fully furnished (turnkey) and has been updated with LVP flooring throughout, renovated baths with tiled, glass enclosed walk-in showers. The renovated kitchen is fully stocked with all dishes & supplies for rentals. There is a king bed in main bedroom with a queen in the second and a fold out murphy bed in the living room so the condo can accommodate up to 6 people. There is a community pool and spa with ample uncovered parking.

3625 Seaside Dr Unit # 25304, Key West

$950,000

2 Beds ⋅ 2 Baths ⋅ 620451 MLS

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

1800 Atlantic Blvd Unit 218B, Key West

$1,450,000

3 Beds ⋅ 2 Baths ⋅ 620448 MLS

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

2313 Fogarty Ave, Key West

$665,000

2 Beds ⋅ 2 Baths ⋅ 620447 MLS

3200 Harriet Avenue | Key West, FL Tucked away on a desirable corner lot, this spacious 2-bedroom, 1.5-bath townhouse offers 1,332 square feet of comfortable living and one of the largest floor plans in the community. Combining privacy, generous living space, and exceptional outdoor amenities, this home is a rare find in Key West. One of the property's most appealing features is the absence of HOA fees, allowing you to enjoy all the benefits of homeownership without monthly association dues or restrictive community fees. It's a rare opportunity to own a spacious townhouse with the freedom and flexibility typically associated with a single-family home. Step outside to your own private pool, creating the perfect setting for entertaining, relaxing, or enjoying the tropical island lifestyle year-round. The corner-lot location provides added privacy and outdoor space, making this home feel even more secluded. Inside, the well-designed floor plan offers bright, inviting living spaces with plenty of room to gather, work from home, or simply unwind after a day on the water. Conveniently located in New Town, 3200 Harriet Avenue is just minutes from shopping, dining, schools, beaches, and all that Old Town Key West has to offer. Whether you're looking for a primary residence, vacation home, or investment property, this home delivers an outstanding combination of space, privacy, and the quintessential Key West lifestyle.

3200 Harriet Ave, 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

$625,000

2 Beds ⋅ 2 Baths ⋅ 620312 MLS

One owner since new, this Key West Golf Club townhome has been maintained with a new roof, new A/C, and an updated kitchen and baths -- the major systems and finishes are already done. Tile runs throughout the first floor, which opens across the kitchen, dining, and living space, plus a half bath for guests. Upstairs holds two bedrooms and a full bath finished with durable, eco-friendly cork flooring -- a resilient, long-lasting surface prized for comfort underfoot and sustainability -- along with a permitted enclosure of the front balcony that adds livable space most units in the complex don't have, plus an in-unit washer/dryer and dedicated storage. Outdoor living wraps the home front to back: a covered front porch, two screened back porches, and a fenced yard built for grilling and entertaining. The community pool, gym, and Zen garden are steps away. The location is what sets this community apart. Key West Golf Club is the island's only gated golf-course community -- a Rees Jones-designed 18-hole course, on-site bar and grill, two pools, a fitness center, and 24-hour gated security. Old Town, the beaches, and the marinas are a quick car or bike ride away. HOA dues are reasonable and cover cable and common-area maintenance. Zoning allows 30-day minimum rentals, so the unit works for seasonal income, long-term tenancy, or part-time ownership. The numbers back it up: at 871 verified square feet, this is the largest 2-bedroom, 1.5-bath townhome currently listed in the community -- and at $718 per square foot, the lowest-priced per foot in its category. Owner financing may be considered for qualified buyers, adding flexibility rarely found in this market. One careful owner, move-in ready, priced to move, in a location that doesn't come around often. Schedule your private showing today.

1 Spoonbill Way, 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

$3,800,000

3 Beds ⋅ 3 Baths ⋅ 620343 MLS

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

619 Ashe St, Key West

$2,685,000

4 Beds ⋅ 5 Baths ⋅ 620332 MLS

Brand-new construction in one of Key West's most desirable residential neighborhoods, the Casa Marina area of Old Town, just blocks from upper Duval Street and four blocks from the beach. This 4 bedroom, 4.5 bath single-family home blends modern durability with relaxed island living, offering the ease of low-maintenance ownership in the highly sought-after X flood zone. Built in 2026 to Florida's toughest standards, the home features concrete board siding, impact doors and windows, and an elevated first floor. The construction is designed to withstand winds up to 180 MPH. Inside, spacious living areas with high ceilings flow comfortably to a private outdoor retreat with an inground pool and water features. All bedrooms are en-suite, with one located on the first floor. A $15,000 builder appliance credit allows you to choose the finishes and appliance brands, at cost, that best suit your lifestyle. Off-street parking adds everyday convenience, while reclaimed wood accents from the historic schooner Western Union bring a meaningful connection to Key West history into the architecture. Quiet, private, and close to everything, this home offers luxury, walkability, and the best of Key West living.

1316 Royal St Unit 6, Key West

$865,000

2 Beds ⋅ 1 Baths ⋅ 620303 MLS

Freshly relaunched and ready for its next chapter, this beautifully maintained 2-bedroom, 1-bath condo in Shipyard offers the Key West lifestyle everyone is looking for: easy living, a sought-after location, and true indoor-outdoor charm. Set on the second floor, the condo features two private balconies, one in front and one in back, perfect for enjoying tropical breezes, morning coffee, or a quiet moment after a day downtown. Inside, the open living area flows comfortably into a modern kitchen, creating an inviting space for relaxing or entertaining. A uniquely spacious bathroom, rarely found in Shipyard condos, adds extra comfort and practicality. Offered fully furnished, this home is move-in ready and well positioned for personal use or rental income. The lushly landscaped Shipyard community offers a pool, winding paths, and a peaceful setting just moments from Fort Zachary Taylor State Park, the waterfront, Truman Annex, and the restaurants, galleries, and energy of Duval Street. Whether you are looking for a Key West getaway, full-time island home, or investment property, this condo delivers location, lifestyle, and ease in one of Old Town's most desirable communities.

204 Southard St Unit 5, Key West

$2,999,000

3 Beds ⋅ 4 Baths ⋅ 620286 MLS

1627 Johnson St. -- A Legacy of Design, A Life Fully Lived. Some homes reveal themselves slowly -- and this is one of them. Designed by the late Michael Ingram, one of Key West's most celebrated architects, this was his final project and, for three years, his own home. He built it the way he lived -- with intention, precision, and an uncompromising commitment to quality that no passing glance from the street could convey. Step through the gate and the story becomes immediately clear. Completed in 2019 on an oversized 7,200-square-foot corner lot, the residence is enclosed by solid concrete walls that create a world entirely apart -- private, lush, and serene. Soaring vaulted ceilings, white oak floors, and six skylights flood the open living spaces with natural light. Impact-rated windows and doors, automatic electric blinds throughout, and a built-in generator ensure effortless comfort in every season. The kitchen features a gas stove, custom cabinetry, and a butler's pantry. The primary suite is finished in deep charcoal tones with an oversized shower. The current owner layered Ingram's architecture with a fearless, joyful personality entirely their own -- designer wallpaper in sweeping hues of hot pink crowns the guest room ceiling, setting the tone for interiors that are bold, tropical, and entirely alive. Offered fully furnished and move-in ready. Outside, the resort-style experience unfolds across an elevated pool with an infinity-edge waterfall, in-pool lounge chairs, and a bespoke weatherproof TV enclosure -- custom-designed to open automatically so you never have to leave the water. The surrounding IPE hardwood deck, prized for its density and natural resistance to the elements, frames it all beautifully. Mature palms, lush tropical plantings, a covered two-car carport, and a detached one-bedroom guest house -- ideal for visitors, rental income, or a private office -- complete a property that simply cannot be appreciated from the street.

1627 Johnson St, Key West

$3,495,000

4 Beds ⋅ 5 Baths ⋅ 620222 MLS

Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir package, open flow to the living and dining rooms. And it earns from day one. High six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

710 Caroline St, Key West

$868,000

2 Beds ⋅ 2 Baths ⋅ 620198 MLS

Rare opportunity to own a transiently licensed 2-bedroom, 2-bathroom condo in Key West, offering exceptional flexibility for personal use and short-term vacation rental income. Located within the sought-after Sunrise Suites community, this beautifully updated residence combines modern coastal style with a prime island location just minutes from beaches, Old Town, and Key West's most popular attractions. Inside, you'll find a bright, open-concept living space featuring elegant quartz countertops, contemporary white cabinetry, and a thoughtfully designed layout that maximizes comfort and functionality. The spacious primary suite and guest bedroom provide comfortable accommodations, while the open living and dining areas create the perfect setting for relaxing or entertaining. A private balcony offers the ideal place to unwind and enjoy breathtaking sunset views over the island. This turnkey condo is equipped with a beautifully updated kitchen, in-unit washer and dryer, and central air conditioning, making it equally appealing as a primary residence, second home, or investment property. Owners and guests enjoy access to resort-style amenities including a shared heated swimming pool, hot tub, tennis court, and beautiful walking and biking paths. The community's convenient location near Key West International Airport and just a short drive from Duval Street provides easy access to world-class dining, nightlife, shopping, fishing, and water sports. With its coveted transient rental license, updated interior, desirable amenities, and strong vacation rental potential, this Key West condo presents an outstanding opportunity to own a piece of paradise while generating income in one of Florida's most sought-after destinations.

3625 Seaside Dr Unit 25410, Key West

$1,799,765

3 Beds ⋅ 3 Baths ⋅ 620197 MLS

Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main home offers 2 bed, and 2 baths thoughtfully designed with bright, open living space and classic Key West character. Added value is the separate guest house featuring an open concept floor plan, a beautiful bathroom, with open first floor bedroom, and an additional sleeping area on the second floor overlook that accommodates up to six guests. Perfect for the extended family/friends, or income producing opportunities, this flexible space offers endless possibilities. End your day with a relaxing swim in your inground 15x15 pool while looking at the stars.

1523 Seminary St, Key West

$3,650,000

4 Beds ⋅ 3 Baths ⋅ 620188 MLS

Stunning possibilities abound for this home on a double lot on the best street in the much sought after Casa Marina neighborhood in Key West. 1017 Washington Street is a renovation away from being your trophy property. The existing house has lots of room with 2,604 square feet of finished space with 4 bedrooms and 2.5 bathrooms. The oversized lot has even more room with 10, 724 square feet, a large swimming pool and an outdoor shed perfect for outdoor kitchen and living space. The property has never flooded and sits above flood. The possibilities are endless. Come see it today.

1017 Washington St, Key West

$999,995

2 Beds ⋅ 2 Baths ⋅ 620187 MLS

Wonderful Home with a small cottage, pool, and off Street parking! New roof will be put on this month. The main home has an open living room with cathedral ceilings, and a loft . The kitchen has french doors leading to a large deck, and a private back fenced yard. Chicago brick surrounds the Salt Water pool and cottage, with lots of additional space. There are plans by Serge with Artibus Designs for an addition added on to the home if desired giving an additional bedroom, bath, dining room, etc. Wonderful property as is or expand for more square footage!

3808 Duck Ave, Key West

$1,799,000

3 Beds ⋅ 3 Baths ⋅ 620176 MLS

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

2101 Harris Ave, Key West

$1,849,000

2 Beds ⋅ 2 Baths ⋅ 620154 MLS

TRANSIENT investment opportunity awaits. Spacious 2bd/2ba situated in the centrally located waterfront community of 1800 Atlantic. Large covered balcony overlooks a lush tropical courtyard with huge beachfront pool, hot tub and distant ocean view. Offered fully furnished turnkey with a strong professionally managed vacation rental history and future rentals already in place. Recently underwent a full kitchen renovation. Convenient assigned covered parking space with a private storage area for bikes and beach toys. This unit also shares a large indoor storage unit with shelves for an additional $200. a month. This is an active vacation rental, showings preferred on turnover days.

1800 Atlantic Blvd Unit 315B, Key West

$1,300,000

3 Beds ⋅ 2 Baths ⋅ 620150 MLS

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

611 Grinnell St Unit 4, Key West

Browse All Key West FL Properties with Pool for Sale

Key West Homes with Pool

Angela Palma

Search

Resources

About