luxury houses with pool for sale Monroe County, United States (page 5)

The ultimate lock-and-leave Key West retreat awaits in the heart of Old Town! Perfect for those seeking a low-maintenance getaway this residence offers effortless luxury living and the convenience of a fly-in, fly-out lifestyle.Located on exclusive Admirals Lane within the award-winning TRUMAN ANNEX. The home features soaring 10-foot ceilings on all three levels, a bright open floor plan, and a stunning modern kitchen with quartz countertops and stainless-steel appliances.With 4 bedrooms and 3.5 bathrooms, the layout provides flexibility and comfort for family and guests. The first floor offers spacious living and dining areas that open through impact French doors to a private tiled patio surrounded by tropical landscaping--ideal for entertaining. The second floor includes a spacious primary suite with ensuite bathroom and a guest room with a separate bathroom. The stacked washer and dryer is located on the 2nd level. The third floor provides a private guest area with two bedrooms and a shared bath, each featuring tall ceilings and two queen beds per room.Impact windows and doors throughout, assigned covered parking, and access to the Truman Annex community pool add to the ease of ownership. Just steps from Duval Street, fine dining, and the waterfront, this home delivers the best of Key West living--lock it, leave it, and love it.

Seller Financing Available | Pre-Construction Waterfront Retreat | Deep Water | Sunrise Views Located right across from the island of Boot Key, this exceptional pre-construction offering combines protected deep-water living, open-water views, and one of the most desirable boating locations in Marathon. Explore scenic kayak trails for beginners and advanced paddlers, surrounded by rich nature and wildlife where dolphins and manatees are frequently seen. The property faces east for breathtaking sunrises, while Boot Key provides natural protection during stormscreating an ideal, secure harbor environment. With approx 60 feet of deep-water dockage, enjoy ample space for large or multiple vessels, excellent maneuverability, and direct access to world-class boating. Inside the harbor, convenience is unmatched with 5 restaurants and 3 gas docks just minutes away. Commencing soon on this with construction, the custom home is designed with modern coastal style and true Keys practicality. The residence will feature 3 bedrooms and 2.5 bathrooms, offering elevated living spaces perfectly oriented toward panoramic Boot Key Harbor views. Whether you're a dedicated boater, nature lover, investor, or seeking a peaceful Keys escape, this rare property delivers the ultimate blend of location, protection, and lifestyle. Seller will finance with half down!

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic districts, this property is just minutes away from famous landmarks, restaurants, and local shops. Take advantage of nearby beaches, water sports, and lush parks, offering a vibrant lifestyle for outdoor enthusiasts. This multifamily compound not only serves as a wonderful family home but also presents a lucrative rental opportunity in one of the most sought-after destinations in Florida. Don't miss your chance to own a piece of Key West history. Schedule a viewing today. Owner financing is available.

This breathtaking five-acre oceanfront estate, with 244 feet of private ocean frontage, is the crown jewel of the Florida Keys. From the moment you pass through the gates, you'll be captivated by a world of elegance, privacy, and unparalleled amenities. At the heart of this premier estate lies a resort-style pool oasis. The custom-designed 5,600+/- square foot main residence showcases exquisite craftsmanship. A separate 2,999 sq.ft. guest house offers a private retreat. A marina provide direct access to the world-famous waters of the Keys. Enjoy the gourmet kitchen, guest suites, movie theater and even the potential for a private hangar. This estate isn't just a home; it's a lifestyleyour personal resort blending tropical serenity, architectural excellence, and unmatched prestige.

Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal style. The lush tropical yard is a true paradise with all new low-maintenance landscaping, irrigation, evening lighting, and artificial turf.The 75-foot concrete dock offers deep-water access for large vessels (current owner has a 42' boat), complete with a new covered fish-cleaning station. Entertain with ease under the spacious covered patio or on the large upper deck overlooking the sparkling canal. The enclosed garage provides secure storage, while the newly paved driveway offers ample parking for vehicles, trailers, and even an RV--complete with hookup. Lower level storage and bonus space.Just minutes from the Summerland Key airstrip, this property offers the ultimate convenience--fly in and boat out! Experience the best of Keys living in one of the most desirable neighborhoods in the Lower Keys. Don't miss out on this one--your coastal haven awaits!

Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft. and is designed to showcase sweeping, unobstructed views of the Atlantic. The grand open living and entertaining space features soaring ceilings and walls of glass that frame endless turquoise water vistas, creating an airy coastal ambiance throughout.Step outside to your own private resort with a sparkling oceanfront pool and spa, surrounded by expansive decks ideal for sunset cocktails or gatherings with family and friends. A rare concrete dock with a cut-in boat slip provides quick, direct access to world-class fishing, diving, and boating--an extraordinary feature highly coveted in the Florida Keys.Outdoor living is elevated with a poolside summer kitchen, multiple lounging decks, and panoramic views in every direction. Upstairs, the spacious primary suite offers breathtaking ocean views, a private balcony, and the ultimate retreat for rest and relaxation.Additional features include impact windows and doors, a metal roof, and a chef's kitchen with granite countertops and stainless steel appliances.This is Luxury Coastal Living at its Finest--a premier oceanfront home offering rare amenities, deepwater access, and unforgettable views in one of the Florida Keys' most sought-after communities.

Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and diving.A protected 6-boat basin with room for extra boats is the centerpiece of the waterfront, complete with 25K and 16K lifts, a boat ramp, sandy beach, lookout point, and composite observation deck. After a day on the water, unwind in the lagoon-style saltwater pool with heater, chiller, and custom water features. The expansive tiki bar includes TVs, True refrigerator/freezer drawers, and an ice machine--perfect for effortless outdoor entertaining. Additional features include a firepit, private sandy beach, and a full outdoor kitchen equipped with built-in BBQ, Viking appliances, and True refrigeration.The upper level offers a bright and open Great Room with sweeping ocean views, a spacious dining area, and a chef's kitchen with stainless appliances. Two covered verandas provide ideal spaces for taking in the breezes and panoramic vistas. The primary suite features an office, en suite bath, walk-in closet with laundry, sunroom, and loft. Two additional upstairs guest rooms comfortably accommodate visitors, while the separate downstairs living area offers three more guest bedrooms for privacy and flexibility.Designed for hosting and convenience, the home is equipped with a Sonos sound system, property-wide Wi-Fi, abundant storage, a two-car garage with fishing lockers, and generous parking along a winding paver driveway. Lush, mature landscaping surrounds the property, creating a serene and secluded Sugarloaf Key retreat.Call for more information today!

This luxe, oceanfront estate will be sold at Luxury AUCTION Without Reserve on December 4, 2025! List price for REFERENCE ONLY. Offered in co-op. with Platinum Luxury Auctions. Inquire for details.Trophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by multi million dollar estates favored by celebrities and business leaders. Fly in and boat out! Located in one of the most exclusive areas of the Florida Keys, this one-of-a-kind estate offers the ultimate blend of luxury, privacy, and unmatched boating access. Set on a beautifully landscaped 37,400 sq ft lot with 120 feet of direct oceanfront, this residence is a rare opportunity to own a property designed for discerning buyers who demand the best. Boaters will be captivated by the 120,000 lb yacht lift, capable of hosting up to a 75 ft vessel--an extraordinary find in the Keys. The estate also features a private mooring buoy, two additional boat lifts, and a private boat basin. With exclusive bay bottom rights, this is a true boater's paradise. Inside, the home boasts 5 bedrooms, 4 full baths, and 2 half baths. The spacious guest suite features a separate sitting area currently set up as a gym with a half bathroom, and a large bedroom with ensuite bathroom. The open-concept living area showcases vaulted ceilings, a chef's kitchen with high-end appliances, and seamless indoor-outdoor flow to a sprawling tiled patio. Enjoy breathtaking views of the Atlantic and Little Palm Island from the raised pool, spa, and covered bar area, perfect for entertaining in style. The estate also includes a private beach, desalination plant, and backup generator, ensuring complete self-sufficiency. Additional highlights: one-car garage, large storage space, circular drive, and lush tropical grounds that evoke a luxury resort. Fly into paradise at Summerland Key Community Airport for residents only - helicopter and small aircraft. This exceptional property offers the pinnacle of Florida Keys living.

This super cute historic Old Town Key West 2,205 sq. ft. Conch-style home is perfectly positioned just steps from famous Duval Street and one block from the ocean, South Beach, and the Southernmost Point. If you're seeking the best location in Key West--walkable, vibrant, and effortless--this property is unmatched. The sun-filled first floor showcases timeless Dade County pine, cherry floors, and an open layout designed for easy island living. The spacious living and dining areas flow naturally into the chef's kitchen, complete with Silestone countertops, stainless-steel appliances and custom wood cabinetry. A cozy sitting room offers a quiet retreat, while a half bath with stackable washer/dryer adds convenience.Step outside to your private backyard oasis--lush landscaping, a covered pergola perfect for dining or lounging, and a sparkling pool create the ideal setting for relaxing or entertaining after a day exploring Old Town.The second floor offers two guest bedrooms with a shared full bath, plus a beautiful front balcony with peek-a-boo ocean views and the iconic Southernmost House--an ideal spot to unwind at sunset.The entire third floor is a luxurious primary suite, offering maximum privacy with reclaimed wood finishes, spray foam insulation, a spacious walk-in closet, and a spa-inspired bath featuring double Kohler body jets and a ceiling-mounted rain shower.Homes in this location--quiet, charming, and mere steps from Key West's best restaurants, galleries, beaches, and nightlife--are incredibly rare. This is the perfect retreat for buyers who want to enjoy the island on foot and live in the heart of everything.Come experience the best of Key West living. You will love this Old Town gem!