Tranquil Midtown Estate feels worlds away, while just minutes to delectable dining and nightlife in exciting Key West! Nestled on nearly a quarter-acre of gated, lush tropical gardens, this spacious 3/3 main house plus 1/1 guest house comes move-in ready; boasting elevated coastal design where modern finishes and amenities meet relaxed sophistication. Indulge in year-round temperate weather from a backyard oasis, masterfully outfitted for hosting memorable gatherings with a well-equipped outdoor kitchen with gas grill, gas burner, ample prep space and beverage cooler. Lounge poolside, cocktail in hand, in the shade of a large tiki hut and cool off in the stunning resort-style pool, complete with fountain waterfalls! Additional exterior features include brick paver pool deck and outdoor rain shower. Upon entry, the main house features an open-concept great room with walls of impact glass windows and doors, providing abundant natural light. The immaculate Chefs Kitchen, with quartz countertops, glass tile backsplash, premium stainless-steel appliances, and island with seating, allows for effortless entertaining. As a bonus, a Dutch door leads to a spacious butlers pantry with laundry. The primary suite enjoys privacy in its own wing, and comes equipped with luxurious en suite, walk-in closet, and access to a private garden. The separate guest wing offers two expansive bedrooms and two full bathrooms. The well-appointed guest house offers two floors, with living room and kitchenette on the main level, complete with serene pool views and impact glass doors leading out to a private, poolside composite deck. The upstairs guest bedroom offers loads of privacy and en suite bathroom. Enjoy an abundance of covered parking with two pergola carports and additional off-street parking. Located within a quiet, established neighborhood but in proximity to restaurants and convenience stores in town, this ideal location offers the best of both worlds!

Not a duplex! This beautiful property consists of two single family homes surrounded by tropical foliage. This one-of-a-kind compound blends island charm and character. Offering a 3 bedroom 4-bath Conch house with a large separate 1 bedroom 1 bath home with a full kitchen. The 3 bedrooms, 4 bath home has wall-to-wall Dade County pine with an open floor plan and a chefs kitchen. The open concept living space flows effortlessly into a sleek kitchen with quartz countertops, stainless steel appliances, and offers a tranquil escape just steps from the pool. The second, 1 bedroom, 1-bath home provides secluded privacy for visitors or a lucrative rental opportunity. Surrounded by lush, mature landscaping and brick pathways, the private courtyard creates a peaceful hideaway, perfect dip in the heated oversized pool. Steps from Key Wests vibrant restaurants, galleries, and historic landmark.

Tucked away on a quiet lane in the heart of Old Town Key West, this one-of-a-kind compound blends island charm and character. Offering three distinct dwellings wrapped around a serene brick courtyard and heated cocktail pool, this property is a rare gem providing ultimate privacy while just steps from world-class dining, shopping, and entertainment.The main house is a light-filled updated 2-bedroom, 2-bath home featuring vaulted ceilings, hardwood floors, and French doors that open onto spacious porches. The open-concept living space flows effortlessly into a sleek kitchen with quartz countertops, stainless steel appliances, and an island with seating perfect for gathering with friends. The primary suite includes an en-suite bath and an outdoor shower tucked away for a private island experience. The second bedroom opens directly to the courtyard, offering a tranquil escape just steps from the pool.A detached 1-bedroom, 1-bath guest cottage provides secluded privacy for visitors or a lucrative rental opportunity. The third structure, set amongst the tropical landscaping, is a flexible bonus space ideal as an art studio, office, or additional sleeping quarters.Surrounded by lush, mature landscaping and brick pathways, the private courtyard creates a peaceful hideaway, perfect for al fresco dining or a dip in the heated cocktail pool. With off-street parking, a whole-house generator, and a fully fenced perimeter, this property checks every box for island living at its finest.Moments from Key Wests vibrant restaurants, galleries, and historic landmarks, these cozy cottages offer a welcoming slice of paradise in one of the most sought-after areas of Key West.Schedule your private tour today and make this hidden paradise your own.

Welcome to The Chavez House, a beautiful 3-bedroom, 2 bath transient rental home proudly listed on the National Register of Historic Places. With a solid rental history, this property is a fantastic investment opportunity in the heart of the historic seaport neighborhood.Upon entering, youre greeted by a bright and inviting family room bathed in natural light--an ideal space for intimate conversations and gatherings. The main floor features a spacious primary en-suite bedroom with king-size accommodations, accentuated by Dade County pine walls and a thoughtfully designed bath with dual sinks, a tub/shower combination, and a separate pedestal sink room.The inviting dining area comfortably seats six and offers an option for outdoor dining on the lanai, creating an authentic island experience. The lanai, complete with a vaulted ceiling and tropical fan, serves as an excellent gathering spot for family and friends. The kitchen features a convenient breakfast bar for four, stainless steel appliances, white quartz countertops, and a vaulted shiplap-style ceiling. French doors lead to a private pool area where you can relax in the heated pool, surrounded by lush tropical landscaping.Ascend the beautiful wrap-around staircase to discover two additional queen bedrooms on the second floor, each featuring unique elements such as barn doors, vaulted ceilings, and ceiling fans. The shared bathroom includes a vanity sink and tub/shower combination, ensuring comfort for all guests.Located in vibrant Old Town, The Chavez House, is just a short stroll from the allure of Duval Street, the Key West Cemetery, and the Historic Seaport district. With its proven rental history, this Transient ensures the potential for lucrative income and offers a serene escape.Dont miss your chance to own The Chavez House--where historic charm meets modern living. Schedule your showing today!

This is one of the very few waterfront homes in Old Town Key West that comes with a private boat slip and open water views. The house features a large living room and kitchen area and a gorgeous sunroom with floor to ceiling windows overlooking the water and leading out to a spacious deck. A private path from the deck gives access to a heated pool that is part of the HOA fees that also include use of the dock. The house comes fully furnished, PLUS includes the boat and boat trailer. The private boat slip features a custom floating boat lift and there is easy open water access from the Garrison Bight Marina for fun during the day. This Meadows house is also walking distance to Duval Street for night time dining and entertainment. Plus two private, dedicated parking spots.. A rare gem that will not last!

Beautiful Meadows Masterpiece located one of Key Wests idyllic neighborhoods. Built in 2020 using the finest materials and craftsmanship, this home combines the best of Key West Architecture with modern luxury finishes.Exquisite Nickel-grooved walls and stunning hardwood floors that create a warm and inviting atmosphere. The coffered ceilings, adorned with Dade County Pine add that extra touch of sophistication, while the impact windows and slider patio doors provide both beauty and peace of mind.The spectacular chefs kitchen is a culinary dream, showcasing quartz countertops and a premium viking appliance package. Overlooking the living and dining area, it opens up via two large pocket sliders to sun-kissed patio and heated pool and also features two electric awnings providing an element of shade.Each of the four bedrooms is en suite, with custom closets, custom Bahama shutters and stunning bathrooms, finished with luxurious marble, quartz and iridescent tile, ensuring comfort and style for everyone.Exterior package is equally impressive, featuring decorative shutters, full irrigation and lighting, mature tropical landscaping providing lots of privacy and light composite decking. Chicago brick walkway and off street parking add to the propertys charm and functionality.Located in an x-flood zone, this home was constructed using the highest level of building codes and standards with many luxurious features, resulting in an exceptional home in a beautiful neighborhood.

Discover your dream home at the prestigious Truman Annex Community, situated on the serene Admirals Lane. This two-story detached single-family residence offers a perfect blend of comfort and elegance with 3 bedrooms and 3 full bathrooms. Enhanced by impact windows and doors, the house also features a private carport for added convenience. Adjacent to the property lies a shared community pool, ideal for relaxation and enjoyment. Inside, the main living area boasts exquisite travertine floors, creating a luxurious ambiance. Open the French doors to the composite wood back deck, where outdoor dining, barbecues, and lounging become a daily indulgence. The fully equipped kitchen is a culinary haven, catering to every chefs desires. With one bedroom on the first floor and two bedrooms on the second floor, each with a private bathroom, this home is designed for utmost comfort and privacy. Emphasizing its prime location, this property is just a stones throw from Duval Street, the Key West White House, and the Key West Harbor, all while being nestled within the security of a gated community. Live out your Key West dreams in this exceptional property that epitomizes the essence of island living.

Beautifully renovated mid-century home in the heart of Key West. This property is sited on a 9510 sq ft lot and offers a large in ground pool with 28 ft custom waterfall. This spacious 4BR+den home is ideal for guests and entertaining with large chefs kitchen, open living and dining area with impact rated sliders opening to pool area. Brand new kitchen with cabinet space galore, walk in pantry, wet bar with beverage fridge & glass washer, commercial refrigerator/freezer, built-in ice maker, induction range, double ovens and more. Split bedroom layout is a dream for guests including a main level en suite plus upper level luxury primary bedroom suite. Three bedrooms, 2.5 baths plus den on main level. Upper level boasts cathedral ceilings, primary bedroom with en suite full bath, and large dressing room/closet. Upper level living and additional kitchen space opens to the private rooftop deck with tree top views. Two laundry rooms, tankless water heaters, 3 NEW central AC units, and more! Heated pool, impact windows and doors. NEW electrical and plumbing, irrigation system, landscape, wifi extenders for both levels. Expansive outdoor areas for relaxing poolside, grilling, reading/dining under the covered porch, or swimming laps. Outdoor shower and half bath off pool area. Garage and driveway parking for autos or water toys. Offered furnished!

Welcome to 3615 Eagle Avenue, a stunning, spacious, custom built residence surrounded by its own private botanical garden. The oversized double door entryway indicates what awaits you on the inside. Large sweeping rooms with high cathedral ceilings, gorgeous tile floors, double doors opening to the garden from every room, all designed with one-level living and an emphasis on engaging one eye to the stunning nature that surrounds you. The chef in your family will dance with delight in the spacious kitchen built for creating and entertaining with new Sub Zero refrigerator, gas stove, two dishwashers, wine cooler, and ice machine. Each room has been upgraded with impact windows and doors with views of the luscious tropical delights that await you outside from every angle. Currently configured as a three bedroom with an additional spacious office that would easily convert to a fourth bedroom. Master suite privately located in front of the house with a newly renovated master bath that exudes luxury and style. The 12,000 sq. ft. lot encompasses a large thrilling botanical garden full of life with an emphasis on native plants and palms attracting all the local birds and butterflies. A covered pavilion overlooking the 33 pool and spa with a sand walkway that meanders through the tropical plants. A double car garage with built in storage with additional off-street covered parking for three more vehicles to store all the family toys. House is equipped with a generator, lots of storage, separate utility entryway, exterior lighting and irrigation. Book your showing today to see this extraordinary home as you wont be disappointed.

Experience the epitome of luxury in this exquisite 3BD/3BA residence nestled on a quiet Lane in the heart of Old Town Key West, just a stones throw from the world famous Southernmost Point and 1 block from the iconic Duval Street. Indulge in the unparalleled convenience of having Key Wests renowned restaurants, museums, and art galleries at your doorstep, with the beach a leisurely bike ride away. Step into the modern charm of this meticulously maintained home, which was thoughtfully constructed in 2002. Enjoy the convenience of an open floor plan that seamlessly combines the living, dining, and kitchen areas. Revel in the sleek and stylish stainless steel appliances, complemented by the elegance of granite countertops and custom cabinetry. High vaulted ceilings create an inviting sense of space, while a harmonious blend of tile and wood floors adds a touch of sophistication. Into the backyard oasis, where a delightful heated and chilled pool awaits, ensconced in the lush embrace of tropical foliage. The custom tiki hut beckons you to entertain in style, making this outdoor space perfect for hosting gatherings with family and friends. The grandeur of the primary bedroom is unparalleled, with a jaw-dropping en suite bath and an expansive walk-in closet, offering a retreat within your own home. Recent enhancements include fresh paint, the pools artful re-tiling and resurfacing, and the installation of a brand-new Central A/C system, ensuring your comfort and satisfaction. Dont let this extraordinary opportunity slip through your fingers!

Gorgeous tropical gardens greet you to this enchanting home in the coveted Casa Marina neighborhood. Enjoy a spacious 3 beds/ 2.5 baths with pool and off-street parking. While the home is complete with all the amenities one would expect in an island home the improvements are intentionally simple yet thoughtful to preserve its vintage charm. Through the front door you will be welcomed to a spacious sitting room that can adapt to your personal needs as a generous bonus space. Just past the two guest rooms with shared bath you will find a striking greatroom with soaring 2 story ceiling heights that flood the room with natural light. Enjoy the open yet dedicated dining room and a delightful petite kitchen that overlooks the pool and back gardens. The upstairs is reserved for the primary suite alone and boasts a unique balcony overlooking the great room for a spacious open and airy feel. Thoughtful improvements carry to the outside with low maintenance composite decking, full exterior paint just completed and storage for your extras. Come take a look at this gracious home awaiting someone to adore its thoughtful preservations and authentic charm.

Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

In the heart of it all, here is a home you are sure to fall in love with. This luxury home offers the perfect blend of comfort and convenience, ideal for both vacationers and full-time residents. Boasting 3 spacious bedrooms and 3 modern bathrooms, it provides everything you need for a relaxing and enjoyable stay. The inviting front porch is perfect for people-watching, while the private pool offers a refreshing escape. With two off-street parking spaces, youll never have to worry about finding a spot.Its prime location means youre just a short walk from a variety of attractions, including restaurants, the harbor front, shopping, and exciting water activities. The home underwent complete reconstruction in 2019, ensuring it has all the modern amenities and style youre looking for. Whether youre here to relax or explore, this home offers it all.

Excellent opportunity to purchase a luxurious, modern, and refined single family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living spaceand situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact rated windows & doors, flood panels for all doors, and 25 KW Generac stand by whole house generator. There is an abundance of windows & doors allowing for plenty of natural light throughout the home. True chefs kitchen features gorgeous cabinets & counter tops with all stainless steel appliances. Dual ovens, gas stove top range, and wine cooler make your kitchen complete. The kitchen opens up to your amazing living & dining room areas. From there you will find this opens up to a super nice covered outdoor patio area, in ground, salt water, and heated 27L X 9W Jacuzzi & pool with water fall. Ready to kick back and relax. Outdoor areas have travertine tiles throughout and have lush native tropical landscaping with lighting & irrigation systems. Property has a 1 car covered carport and CBS privacy fencing around entire property. This home is located within walking distance to Higgs Beach, White St. Pier, and a short distance to Key West Best restaurants, beaches, museums, and art galleries. This is truly a home where modern luxury meets Key West paradise. Listing agents are related to the sellers.

High Performing Monthly Vacation Rental Property! Gross Annual income for 2024 exceeded $110,000. 1017 Angela Street is a beautifully restored 3 bedroom, 3.5 bathroom home with a vibrant personality, nestled on one of the quietest streets in Old Town, just steps from Duval Street and the Historic Seaport. Over $350,000 in recent improvements, including newly remodeled first floor bathroom, new pool heater and pump, new hot water heater, new rear composite decking system, expanded dining room with impact rated French doors, new mini split AC units, and all new landscaping. Enjoy the convenience of modern amenities that this home offers, alongside playful, eclectic touches throughout. Relax and unwind in the private backyard oasis shaded by majestic mango trees, and featuring a heated pool and jacuzzi spa. The entire property is fenced and surrounded by lush tropical landscaping. Additional benefits include first floor primary bedroom, off-street parking in the driveway, and an outdoor shower. Home was tented for termites in 2022. This is Key West living at its finest!

Nestled on a tranquil lane in Old Town Key West, this classic Conch home offers an ideal blend of historic charm and modern amenities. The property features multiple entertainment spaces both indoors and outdoors, seamlessly connecting the expansive living area & kitchen to a covered patio & spacious pool deck. This home includes 3 bedrooms plus a poolside cottage. The gourmet kitchen is equipped with stainless steel appliances and custom cabinetry, flowing effortlessly into the island-style dining room. The main floor primary suite exudes a calming energy with its vaulted ceilings and glass doors opening onto the pool. Features include Dade County Pine walls, wood floors, open floor plan, and tall ceilings. The poolside cottage enhances the outdoor experience with an outdoor shower and an additional bathroom, providing ultimate convenience. Experience the casual yet elegant island lifestyle, where every detail has been thoughtfully designed for comfort and style.

Experience timeless elegance & modern luxury in this stunning Old Town Key West residence, built in 1866 & perched atop prestigious Solares Hill. Meticulously renovated, this historic gem blends rich heritage with contemporary comforts.Step into the foyer at the corner of Southard & Love, where preserved architectural details meet modern sophistication. Dade County pine adds authentic charm throughout, complementing the open-concept living & dining areas. High ceilings, natural light, & original hardwood floors enhance the seamless blend of old & new.The gourmet kitchen features top-of-the-line appliances, custom cabinetry, and quartz countertops, perfect for both casual meals & entertaining. The spacious island connects the kitchen to the living areas, creating a cohesive flow.This home offers four bedrooms, three with their own ensuite bathrooms. The main floor primary bedroom is a luxurious retreat with a spa-like bathroom, walk-in closet, & French doors offering serene island views. An additional main floor ensuite bedroom provides comfort for family or guests.The alternate primary bedroom retreat on the second floor with walk-in closet, vaulted ceiling & new ensuite bathroom boasts Dade County pine, an office or sitting area with a surround of French doors. Escape from it all on the second story hammock porch where a perfect breeze anxiously awaits. A third level bedroom completes this 3-story conch revival home.Outside, enjoy a private tropical paradise with lush tropical landscaping, sunlit multi-level deck, & a refreshing, heated & jetted cocktail dipping pool. The rare off-street parking spot adds convenience in this prime Old Town location.Renovated with care, the home features modern amenities like a state-of-the-art HVAC system and energy-efficient updates, ensuring comfort and style. Steps from Old Towns vibrant culture, dining, and entertainment.Owner is a licensed real estate agent in Florida & the listing agent.

Step into 1511 South Street -- a fully renovated private tropical residence where island living meets sleek, modern design. Beyond the gate lies a lush, low-maintenance paradise, perfect for entertaining. The main house features PGT impact windows and doors, vaulted ceilings, and a spacious open-concept design. The living, dining, and kitchen areas flow seamlessly together, with a commercial-style kitchen boasting high-end appliances and open shelving. For added convenience, the kitchen connects directly to the carport, making loading and unloading a breeze. French doors open to an 18 x 14 Caribbean-style dining loggia, seamlessly blending indoor and outdoor living alongside a custom outdoor kitchen by Paradise Grills. The heated pool has been recently resurfaced, complemented by new stonework and durable WEARDECK composite, creating a stylish and inviting outdoor oasis. Both bright, airy bedrooms open directly to the pool and landscaped side yard, while the spacious laundry room offers extra storage. Beyond the pool, the two-story guest cottage features a bedroom and full bath on the main level, plus a second bedroom and bath upstairs, along with walk-in closets. The guest cottage is equipped with its own generator for added peace of mind. Multiple outdoor storage closets, an air-conditioned attic over the carport, and a canvas-covered rear yard provide even more space to enjoy. Understated from the street, unforgettable once inside--this is Key West living at its finest.

Introducing a Stunning New Build (2023): A Luxury 5-Bedroom, 5-Bathroom Home Step into modern elegance with this newly constructed 3,062 sq. ft. masterpiece on a 5,040 sq. ft. lot. Thoughtfully designed with premium materials and meticulous craftsmanship, this home offers exceptional living spaces and luxurious features that redefine comfort. Boasting 9+ ceilings on both floors, complemented by 8 solid doors, this home exudes grandeur. Porcelain wood-style tiles throughout the first floor, paired with LVT flooring upstairs, provide durability and style. All-wood cabinetry, built-in closets, and custom trimwork highlight attention to detail.Impressive Design Elements: A chefs dream with a sprawling 17-foot island featuring dual-sided cabinetry and seating for 8. Outfitted with professional appliances, a 36 gas stove, vent hood, and a separate bar area with a wine fridge. Dual laundry rooms, located on both floors, make everyday chores effortless. Two distinct living areas--one on each floor--ensure a harmonious balance for family gatherings and private retreats. Primary suite located on the main floor, includes a spacious walk-in closet and a lavish bathroom with dual showerheads, a clawfoot soaking tub, dual vanities with lighted mirrors, and a private water closet. Guest Room includes private entrance, which offers both flexibility and privacy.Built by a Certified General Contractor, this home exceeds current building code standards and State-of-the-Art Features: Impact-resistant windows and doors Double-strapped roof trusses and stainless-steel fasteners Custom seamless gutters and downspouts Spray foam insulation in walls, ceilings, and attic Ice & Water shield secondary roof protection under reflective insulation and aluminum standing seam roof maintenance-free e

First Time on the Market! Surprising water views combined with maximum privacy are the signature advantages of this luxurious and well positioned Overlook home on the exclusive private island of Sunset Key. The original owners bought pre-construction and added many thoughtful upgrades and architectural improvements. This three story, 2 bedroom, 2 and a half bath home has been well maintained and never rented. Years of planting and care have gone into creating maximum privacy with lush landscaping in all directions. The pure realization of a true tropical escape: quiet, serene and secure, with no automobiles, world class amenities including an oceanfront restaurant and bar, full service spa, beautiful sand beaches, community resort style pool, tennis courts and fitness center. Plus Overlook has its own separate heated swimming pool as well. All of this just a quick ferry ride available every half hour to connect to all the action that Key West has to offer. A truly unique island experience! Check it out.