Welcome to 1116 Eaton Street, a quintessential Key West cottage for sale in Old Town Key West offering the perfect blend of island charm, modern comfort, and unbeatable walkability. Located in one of the most desirable neighborhoods in Key West, this beautifully maintained 2-bedroom, 1-bathroom home with a private pool delivers the ultimate Florida Keys lifestyle. Step inside this thoughtfully designed 749 sq ft Key West home, where natural light, efficient layout, and timeless finishes create a warm and inviting atmosphere. The open living space flows seamlessly into the kitchen, making it ideal for both everyday living and entertaining. Outside, your private tropical oasis awaits. Enjoy a heated pool, lush landscaping, and multiple outdoor living spaces including a roof top deck perfect for relaxing, dining, or hosting guests. Whether you're looking for a Key West vacation home, investment property, or full-time residence, this home checks all the boxes. Situated in the heart of Old Town Key West, you're just minutes from world-famous attractions including Duval Street, historic landmarks, dining, shopping, and the seaport. This walkable Key West property offers convenience without sacrificing privacy. Private Pool & Tropical Outdoor Area Prime Old Town Key West Location Ideal for Primary Residence, Second Home, or Investment Classic Key West Architecture with Modern Comforts Don't miss this rare opportunity to own a Key West home with a pool in Old Town under 1 million--where island living meets everyday convenience. Join me in experiencing 1116 Eaton Street, Key West, Florida 33040
A hidden gem nestled in our popular Sunrise Shores New Town district, this distinguished single family home is a testament to estates providing rare space, privacy and refined living. Not into ''downsizing'' - 3513 Sunrise Drive encompasses 3 bedrooms, 3 full baths, and this 2-story CBS home spans 2,569sf on an expansive 9,487sf landscaped completely fenced-in super-private corner lot. The first floor is set to entertaining with Mexican tile floors throughout, a gourmet kitchen (with new appliances), dining room, open living room, bedroom and bath and a mother-in-law / guest bedroom/bath with private entrance. Both the large covered porch and separate outdoor kitchen / BBQ area state, ''relax and invite your friends over!'' A dramatic flowing staircase leads to the second floor primary master ensuite bedroom with private balcony over-looking the large heated salt water swimming pool, private lush indigenous tropical exotic orchid gardens and gazebo. With private gated entrance, off-street parking, plenty of outside storage areas, and many on-site updates (automatic yard lights, timed irrigation system, Ring cameras throughout, Aquilink pool and fountain control, new roof and gutters, new A/C system, new water heater, new Kohler generator) to name a few. Enjoy our local bars, restaurants, museums, art galleries and shops, beaches, and seaport activities (all within 10 minutes), then come home to a bit of peace and quiet. Comes furnished, this charming home available to purchase and close on at your earliest convenience
Charming 2BD/2.5BA Key West cottage nestled in the sought-after Meadows neighborhood. Recently refreshed inside and out, this home features newer stainless steel appliances, granite countertops in the kitchen and baths, and beautifully updated tile bathrooms, along with numerous additional upgrades. The light-filled great room opens through French doors to a private outdoor oasis complete with a pool, hot tub, and gazebo--perfect for relaxing or entertaining. Offering flexible living, the home features a primary bedroom option on either the first or second floor. Ideally situated just minutes from both Old Town and New Town, this property combines classic Key West charm with modern improvements.
Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive 12,478sf lot. Set back from the street, it offers a level of privacy that is rare for such a central location. The main residence is designed for both everyday living & entertaining and has been furnished with new furniture & finishings adding a refined & move in ready touch. The fabulous kitchen, outfitted with top of the line finishes, opens through huge sliding glass windows to an outdoor bar & entertaining pavilion creating a seamless indoor & outdoor experience. Upstairs, the primary suite offers a quiet escape with its own office, laundry, and a generous covered porch. Throughout the home, reclaimed hardwood floors from the Biltmore, tall ceilings, and natural light highlight the balance between historic charm & modern upgrades. The outdoor space serves as the heart of the property, anchored by a heated & chilled saltwater pool with a tranquil water feature. Two detached guest houses provide a total of 3BD & 3BA, complemented by an additional cottage that can function as a 4th bedroom & bath or a private entertaining retreat. The versatility of this home is truly exceptional, ideal for hosting guests, extended stays, or creating secluded personal spaces. Additional features include a 1,500sf climate controlled attic for storage, off-street parking for up to 7 vehicles, a carport, and a golf cart garage. Positioned in the desirable X flood zone and just 2 blocks from Duval St. and the Historic Seaport, this property represents a rare opportunity to own a significant piece of Key West history, thoughtfully updated for modern living.
HARBOUR PLACE TRUMAN ANNEX. This waterfront gated community boasts amazing ocean views from the pool and patio areas. Unit 102 has an open floor plan that seamlessly connects the dining and living areas, leading out to a private balcony. This residence features two bedrooms, including a spacious primary suite with a large walk-in closet and a full bathroom. The second bedroom is also generous in size and offers plenty of closet space. As a first-floor unit, it provides easy accessibility without the need for elevators or stairs. Additionally, this unit comes equipped with a washer and dryer, along with a covered parking space. Features include central air conditioning, impact windows and doors, and it comes furnished. Harbour Place provides secure entry and a heated pool amidst beautifully landscaped grounds, all just steps away from Duval Street, shopping, theaters, Fort Zachary Beach, and the Amphitheater.
This move-in ready property offers the perfect blend of comfort, functionality, and island charm. Thoughtfully updated, the home features durable vinyl flooring throughout and energy-efficient mini-split systems in every room, providing individualized climate control and lower utility costs. The spacious layout is ideal for both full-time living and investment potential. A private driveway offers convenient off-street parking, while the fully fenced backyard creates a private outdoor retreat--perfect for entertaining, relaxing, or accommodating pets. Additional highlights include in-unit laundry and a clean, modern interior that makes this home truly turnkey. Located in a desirable New Town neighborhood, you're just minutes from shopping, dining, schools, and all that Key West has to offer. Whether you're looking for a primary residence, second home, or investment opportunity, 3700 Northside Drive checks all the boxes.
Spacious Key West townhome with no HOA! Expanded from its original floor plan, this well-maintained home now offers 3 bedrooms, 2 bathrooms, and nearly 1,400 sq. ft. of living space. There is also a bonus area not included in the square footage, perfect for a home office, hobby room, or extra storage. The kitchen features maple wood cabinetry, granite countertops, and stainless steel appliances. Outside, enjoy a low-maintenance fenced yard and plenty of off-street parking. A rare opportunity to own a versatile and spacious property in Key West with no HOA restrictions.
Escape to Sunset Key, a private island sanctuary where refined elegance meets effortless tranquility. Just a four-minute ferry ride--operating 24 hours a day--from the vibrant charm in the heart of downtown Key West, this serene enclave offers the rare balance of seclusion and accessibility, keeping the energy of Old Town within effortless reach at any hour. This exquisite three-bedroom, three-bath beachfront home is thoughtfully designed to capture the essence of elevated island living. Wake to sweeping water views from the primary suite, and enjoy the same serene vistas from the main living area, where natural light and coastal beauty take center stage. Step outside to your private pool and spa, where you can unwind to the rhythm of waves lapping along the shoreline, all while enjoying gentle sea breezes and breathtaking sunsets over the Gulf of Mexico. The expansive main-level primary suite provides a tranquil retreat, while two beautifully appointed guest suites upstairs ensure comfort and privacy for all. Rich hardwood floors and natural stone finishes flow seamlessly throughout, complemented by a warm, sophisticated island aesthetic. Set within a private island enclave, Sunset Key offers access to exceptional amenities, including a gourmet waterfront restaurant, full-service spa, state-of-the-art fitness center, private beaches, tennis courts, and convenient ferry service. Perfectly positioned within minutes of Old Town Key West yet blissfully removed from the crowds, this secluded setting delivers a truly elevated lifestyle--where every detail is designed for quiet luxury and effortless escape.
Tucked within the charm of Old Town Key West, this fully renovated historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the island's most recognized destinations. Set on a deep 4200+ square foot lot stretching from Eaton Street to Thompson Lane, the property offers 3 bedrooms and 2 baths in a setting designed for both everyday living and relaxed entertaining. Recognized as a 2016 Preservation Award Winner, this lovely home reflects thoughtful preservation of its architectural style while incorporating modern updates including a metal roof and a comprehensive renovation. Inside, hardwood flooring, a light-filled living area, and a main-level primary bedroom create a comfortable and functional layout. The open design flows naturally to the outdoor spaces, while the updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, tile backsplash, and dedicated prep space, along with additional storage and an interior laundry area. French doors extend the living space outward to a covered deck and courtyard. The outdoor setting is a defining element of the home, centered around a private heated pool, covered lounge area and outdoor bath. Gorgeous palms and lush plantings frame the backyard, creating a private garden atmosphere with brick walkways and a spacious courtyard for dining and gathering, while string lighting enhances the space for evening ambiance. The deep lot includes off-street parking with a brick-paved driveway accessed from Thompson Lane, a valuable feature in Old Town. Just moments from the Historic Seaport, Duval Street, and some of Key West's most loved local spots, this location provides convenient access to dining, shopping, and live entertainment. With its combination of location, updates, outdoor living spaces, and off-street parking, this property presents a compelling opportunity for use as a primary residence or vacation home in Old Town Key West..
MOTIVATED SELLER! The perfect Key West starter home. This charming CBS single-family residence is situated in Midtown. The interior shines with recent upgrades, including the renovated bathroom and butcher block countertops in the kitchen. The versatile layout features two bedrooms plus a dedicated den--complete with a closet--perfect for a home office or guest space. Step out back into the massive, fully fenced backyard. Plenty of space for a pool and/or outdoor kitchen. The covered carport and dedicated laundry room are added extras that make this the perfect place to call home!
Discover a rare investment opportunity in the heart of Key West. This spacious corner duplex lot at 2330 Staples St and 1428 6th St offers incredible potential with two separate addresses and alley access for three convenient side entrances. The large lot features a charming, spacious cottage complete with a full kitchen, a bedroom with ample closet space, a stylish bathroom, and an attached garage--perfect for comfortable living or rental income. The second unit has been demolished, providing a blank canvas to rebuild your dream home or expand your investment portfolio. Alternatively, you can choose to demolish the existing cottage and build two brand-new units on this generous lot. Mature landscaping surrounds the property, offering privacy and a serene atmosphere. With two separate ROGOs ready to go and the Staples side of the lot free from flooding, you can start building immediately. Don't miss this unique chance to own a versatile property in a prime Key West location with endless possibilities. Whether you're looking to renovate, rebuild, or develop, this property is your gateway to maximizing value and enjoying the vibrant lifestyle of Key West. Act now and make this exceptional property yours!
olid CBS construction home with a durable metal roof, ideally located within walking distance to marinas, restaurants, and local shops. This 3-bedroom, 2-bathroom property offers an elevated position with glimpses of the water from one side. Enjoy a spacious backyard perfect for entertaining, complete with an above-ground pool and plenty of room to relax or expand. The property also features off-street parking ideal for an RV or boat, plus ample street parking for guests. A great opportunity to own a well-built home in a prime Key West location with both convenience and lifestyle at your doorstep.
Rarely does a property of such storied provenance and grand scale grace the Key West market. This is a residence where history breathes. Commanding nearly half a city block in the prestigious Casa Marina district, 1101 Casa Marina Court is an architectural masterwork built by A. Maitland Adams in the early 1930s. Adams was said to be a partner of Charles Thompson, Ernest Hemingway's fishing companion. If the walls could talk at this iconic residence, it would tell you that this is the very home where renowned author Philip Caputo penned ''Indian Country'' and where Gregory Peck and Harry Truman played cards in the dining room. The 20,000 square foot estate seamlessly marries Palm Beach sophistication with island charm, commanding attention with its vast landscaped grounds of unparalleled beauty, sweeping open spaces, and stunning resort-style pool. Tucked behind the walls, awaits a vast courtyard complete with its own meditation garden--perfect for grand entertaining or peaceful relaxation. Along with gated off-street parking for two, the home features five bedrooms and four and a half bathrooms, including a second-story guest apartment that offers privacy and versatility. Recent updates to the home include travertine marble floors, new roof (2025), impact windows and doors, a chef's kitchen, and welcoming fireplace. Enjoy breathtaking open-water views and sunsets from the home's private widow's walk- an elevated retreat perfect for unwinding above it all. Moments away from waterfront dining, beaches, and pickleball courts, this corner estate offers an unparalleled lifestyle for those seeking a piece of island history redefined for modern luxury.
President's Walk townhome in the Truman Annex. This is a two-bedroom, 2.5-bathroom unit that also includes a deeded carport. It is a great location close to the community pool and all the downtown attractions that Key West has to offer. It features an open floor plan with kitchen, half bath, dining and living areas that open to the rear and side yard! Upstairs are two-bedroom ensuites with vaulted ceilings and each with their own private bath and porches. The windows and doors are combination of wood and impact. It has a non-transient rental license that allows monthly or longer rentals.
Tucked away on a quiet private cul-de-sac in the highly sought-after Key West Golf Club community, 25 Kingfisher Lane offers a rare blend of privacy, convenience, and island charm. With easy parking and an exceptional setting, this light-filled residence stands out from the rest.This beautifully positioned home features an expansive wraparound deck, larger than most, along with additional windows that flood the interior with natural light. Located within a gated community, it perfectly captures the essence of relaxed island living. Enjoy tranquil golf course and lagoon views from the back porch, an ideal spot for morning coffee or unwinding in the evening breeze. The open-concept living and kitchen area flows seamlessly to the outdoor spaces, creating a perfect setting for entertaining or simply relaxing in peaceful surroundings.Offering 2 bedrooms and 2.5 baths, the upstairs layout includes two en-suite bedrooms, providing comfort and privacy for residents and guests alike. The oversized side yard adds valuable outdoor space that is ideal for lounging, gardening, or enjoying the Florida sunshine. Residents of the Key West Golf Club community enjoy resort-style amenities, including a lagoon-style pool, a second neighborhood pool, fitness center, on-site management, and 24-hour gated security.Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, this home delivers the perfect combination of comfort, lifestyle, and classic Key West appeal.
Charming second-floor 1 bedroom, 1 bath condominium featuring a functional layout with a kitchen that offers modern appeal and a comfortable living space enhanced by tile flooring throughout. Large sliding doors open to a private balcony overlooking the tennis courts. The bathroom has been thoughtfully maintained with updated finishes. Located within the gated community of Santa Clara Condominiums, residents enjoy a variety of amenities including a heated pool, tennis court, laundry facilities on each floor, two elevators, secure building entry, backup generator, on-site management, and dedicated personal and bike storage. Conveniently situated near shopping, dining, and recreational facilities, this property presents a great opportunity as a primary residence, vacation getaway, or investment. No pets permitted. HOA fee includes building insurance, security, pest control, exterior & common area building maintenance.
Seller financing available and order has been completed for full property replacement with hurricane rated windows, door, and sliders. Poolside, pool view townhome. The home has just been re-freshed with an interior top to bottom paint job, exterior touch up, and new engineered vinyl plank floors have been installed on the main level. First floor is an open floor plan with half bath, kitchen, dining area and living area that opens to a covered porch. The second floor has two bedrooms and a full bath. The Key West Golf Club features a fitness center and a large community pool. Seller is a Florida real estate broker.
Welcome to 3011 Riviera Drive, nestled in the sought-after Riviera Shores neighborhood of Key West! This delightful 4-bedroom, 2-bathroom home boasts versatility and space, featuring a fourth bedroom with private access and an en-suite bathroom--ideal for guests or an in-law suite. The property sits on a generous 6,000 sq ft lot with a large fenced backyard, perfect for adding a pool. Relish in the tranquility of mature banana and mango trees, complemented by tall Christmas palms enhancing the front yard's allure. Enjoy off-street parking, a concrete driveway, and the nearby public boat ramp for aquatic adventures. The home includes modern comforts such as a durable metal roof, impact windows and doors, a new electric panel, storm shutters, and a privacy fence. Relax on the covered back patio, and appreciate the proximity to Key West's Old Town, beaches, schools, shopping, and businesses--truly an inviting retreat!
NEW PRICE!! Key West WATERFRONT Home with a POOL! This expansive two-story residence has everything you need, featuring a first-floor primary suite, ample off-street parking, and a canal for boating enthusiasts, along with a fantastic pool area complete with a tiki hut for shaded relaxation. With 4 bedrooms and 3 bathrooms, this home spans 2,080 sq. ft. and is just minutes away from Old Town Key West. Nestled on a cul-de-sac, Jamaica Drive is the perfect island oasis--simply drop your paddleboard in from your backyard! The kitchen is chef-ready, offering plenty of cabinet space and a large island. The open floor plan is designed for entertaining, seamlessly flowing to the backyard area with tiki hut, canal views, and a beautiful swimming pool. The first floor includes a primary suite with a luxurious bath, walk-in closet, and pool access. There are three spacious bedrooms located on the second floor. Additional features include central AC, ductless units, a workshop, soundproof windows, impact-rated doors, and hurricane panels. Saltwater pool with chiller and heater. Perfect canal home with seawall without leaving KW!
Ideally located on Simonton Street in the heart of Old Town, this charming half-duplex and lot is just steps from Duval Street and close to dining, shopping, beaches, and neighborhood parks. Perfect as a full-time island residence, second home, or investment property, this home offers the quintessential Key West lifestyle in one of the island's most desirable locations. The property features a welcoming front porch and a private patio surrounded by tropical landscaping--ideal for enjoying the island breeze and outdoor living that makes Key West so special. Inside, the home offers an updated kitchen and bath, ductless A/C units, and the convenience of an in-unit washer and dryer. An additional lot (C-1) is included in the sale, featuring a converted storage unit that provides flexibility. Additional highlights include off-street parking, X Flood Zone designation, and no HOA fees, offering both flexibility and low carrying costs. Whether you're seeking a peaceful island retreat or an investment opportunity in the heart of Old Town, this Simonton Street property captures the charm and lifestyle that define Key West living. Also available to be purchased with other half duplex. See MLS #619049
Ideally located on Simonton Street in the heart of Old Town, this charming half-duplex is just steps from Duval Street and close to dining, shopping, beaches, and neighborhood parks. Perfect as a full-time island residence, second home, or investment property, this home offers the quintessential Key West lifestyle in one of the island's most desirable locations. The property features a welcoming front porch and a private patio surrounded by tropical landscaping--complete with a relaxing jacuzzi, perfect for enjoying the island breeze. Inside, the home offers an updated kitchen, ductless A/C units, and the convenience of an in-unit washer and dryer. Additional highlights include off-street parking, X Flood Zone designation, and no association or HOA fees, providing flexibility and low carrying costs. Whether you're seeking a peaceful island retreat or a low-maintenance home in the heart of Old Town, this Simonton Street property captures the charm and lifestyle that make Key West so special. Also available to be purchased with other half duplex. See MLS #619049
Legal duplex in the heart of Old Town Key West offering flexibility for investors or owner-occupants alike. Each residence features a private entrance, in-unit laundry, electric meter, and thoughtful renovations that make the property truly turn-key. Classic Key West character shines throughout with vaulted ceilings, exposed beams, skylights, and beautiful wood floors creating a bright and airy feel. Updated kitchens, bathrooms, and high-end appliances add modern comfort while maintaining the home's historic charm. Perfect for living in one unit while renting the other, or as a full investment property. The home is fully fenced and includes an off-street parking space, just blocks from Duval Street
Situated along one of Old Town's most storied corridors, residence #6 at 616 Caroline Street offers a refined Keys lifestyle just steps from the Historic Seaport, Duval Street dining, galleries, and marinas. Tucked within a boutique setting, this private upstairs home balances character and comfort with a bright, welcoming living area and an efficient layout that makes everyday living—and easy lock-and-leave ownership—simple. Offered turnkey, the residence conveys fully furnished, allowing you to settle in immediately and enjoy the space from day one. The kitchen and downstairs bath are thoughtfully arranged to maximize storage and function, while the ensuite bedroom retreat provides a quiet place to unwind after a day on the water or in town. Large windows draw in natural light, and pleasant treetop views frame the Caroline Street streetscape. Within the intimate association, owners enjoy access to the community pool set amid well-kept common areas, adding a relaxed resort element to daily life. This rare Old Town offering delivers superb walkability to the waterfront, coffee shops, local markets, and sunset celebrations—whether you seek a full-time home base or an elegant pied-à-terre in the heart of Key West.
Enjoy the largest floor plan in the Santa Clara building with this spacious 2-bedroom, 2-bath condo in the heart of New Town Key West! Welcome to easy island living in tropical Key West, FL! This spacious 2-bedroom, 2-bath condo features the largest floor plan in the building and is conveniently located on the second floor with elevator access. The residence offers tile and laminate flooring, hurricane-resistant windows and doors, and a comfortable layout. Embrace a true resort-style lifestyle as residents enjoy outstanding amenities, including a large sparkling pool, tennis court, secure entry, on-site laundry facilities, and maintained common areas. The building has recently undergone extensive renovations with continued improvements, making this a wonderful opportunity to own in one of New Town's desirable communities. On top of that, this home is ideally located just minutes from some of Key West's finest dining, shopping, stunning beaches, downtown attractions, the airport, and medical facilities, ensuring that this property truly places the best of island living at your doorstep. Whether you're seeking a full-time residence, a smart investment, or the perfect vacation getaway, this condo delivers exceptional island lifestyle, comfort, and location. Don't miss your chance to own this slice of paradise. Schedule your private showing today and experience island living at its finest.
This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom suites. Located just steps from iconic Duval Street, the property provides convenient access to Old Town restaurants, shops, and nightlife while maintaining a quiet resort setting. Resort amenities include swimming pool, fitness center, and off-street parking. Planned improvements to the residences, pool, and fitness areas are scheduled for completion in 2027. The current owner has paid the majority of the special assessment associated with these upgrades. Owners may choose their own rental management company or participate in the on-site program. Suitable for buyers seeking an income-producing investment, second home, or a combination of both.
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Key West is located in Florida. Key West, Florida has a population of 26,776. Key West is more family-centric than the surrounding county with 23.73% of the households containing married families with children. The county average for households married with children is 20.65%.
The median household income in Key West, Florida is $75,638. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Key West is 44.2 years.
The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.6 degrees. The average rainfall is approximately 43.8 inches per year, with 0 inches of snow per year.
