Monroe Homes with Pool

Monroe Homes with Pool

Welcome to Monroe County, Florida – a sun-soaked paradise that perfectly blends natural beauty with vibrant community life. Nestled in the heart of the Florida Keys, Monroe County boasts stunning coastal landscapes, crystal-clear waters, and a rich tapestry of cultural experiences. Whether you're an outdoor enthusiast, a water sports lover, or someone who enjoys the charm of quaint island towns, Monroe County has something for everyone.

One of the standout features of this idyllic region is its stunning homes with pools. Imagine stepping into your own private oasis, where you can soak up the Florida sunshine while lounging by your sparkling pool. These homes are not just residences; they are a lifestyle choice. With many properties offering breathtaking views of the ocean or lush tropical gardens, you’ll find that having a pool is not just a luxury, but a gateway to relaxation and entertainment.

Monroe County’s real estate market is as diverse as its residents, featuring charming cottages, luxurious waterfront estates, and everything in between. The allure of owning a home with a pool here is undeniable, offering the perfect setting for family gatherings, barbecues, or simply unwinding after a long day.

As you explore the possibilities of calling Monroe County home, let the warmth of the sun and the inviting waters inspire your next chapter. Dive into the vibrant lifestyle that awaits you, where every day feels like a vacation in your own backyard. Embrace the charm of Monroe County and discover the perfect poolside retreat that suits your dreams!

Newest Monroe Homes with Pool

9 Beds ⋅ 10 Baths ⋅ A12067078 MLS

One of the Florida Keys' most significant newly completed trophy estates, now making its market debut fully completed and never occupied. This one-of-a-kind waterfront residence offers 18,736 SF of interior living space and more than 29,000 SF under roof on approximately 1.72 acres with 200 feet of ocean frontage. A property of this scale, quality and waterfront presence has become exceptionally difficult to replicate under today's development environment, making it as irreplaceable as it is exceptional. Designed for the most discerning owners, the estate features 9 bedrooms, 9.5 bathrooms, a detached guest residence, private elevator, 9-car garage, and an extraordinary indoor-outdoor living experience highlighted by a newly completed 100-foot infinity-edge pool, separate beach-entry pool, and expansive waterfront terraces, unveiling an outdoor environment never before presented to the market. Included in the offering is a deeded 60-foot boat slip at Bonefish Marina, located approximately two minutes from the residence, providing immediate access to world-class boating and fishing. Marathon International Airport is approximately five minutes away, allowing seamless arrival by private aircraft. Contemporary architecture, exceptional craftsmanship, absolute privacy, and one of the most exclusive waterfront settings in the Florida Keys define this truly irreplaceable trophy estate. One of the Florida Keys' most significant newly completed trophy estates, presented fully completed and never occupied. Situated on approximately 1.72 acres with 200 feet of ocean frontage, this extraordinary residence represents a level of scale, quality and waterfront presence that has become exceptionally difficult to replicate under today's development environment in the Florida Keys.Offering approximately 18,736 square feet of interior living space and more than 29,000 square feet under roof, the residence has been thoughtfully designed to deliver an exceptional indoor-outdoor lifestyle while maintaining the highest standards of privacy, craftsmanship and contemporary architecture.Highlights include 9 bedrooms, 9.5 bathrooms, a detached guest residence, private elevator, garage with nine doors, a spectacular 100-foot infinity-edge pool, beach-entry pool and expansive waterfront terraces designed for entertaining and enjoying the Florida Keys lifestyle.The property also includes a boat slip at nearby Bonefish Marina, located approximately two minutes from the residence, while Marathon International Airport is approximately five minutes away, offering exceptional convenience for owners and guests arriving by private aircraft.Property Highlights• Newly completed and never occupied• Approximately 18,736 SF interior living area• More than 29,000 SF under roof• Approximately 1.72-acre waterfront estate• Approximately 200 feet of ocean frontage• Detached guest residence• Private elevator• Garage with nine doors• 100-foot infinity-edge pool• Beach-entry pool• Boat slip included• Marathon International Airport approximately five minutes away• Contemporary architecture• Exceptional craftsmanship• Designed for privacy, entertaining and the Florida Keys lifestyleAvailable Upon Request• Floor Plans• Survey• Property Presentation• Professional Photography• Cinematic Video• Drone Footage• Additional Property DocumentationPlease contact the Listing Agent for additional information, property presentation, supplemental documentation and private showing arrangements.This is not simply a luxury residence—it is a trophy asset in a market where opportunities to create comparable waterfront estates have become exceptionally limited

2405 Coco Plum Drive, Marathon

4 Beds ⋅ 4 Baths ⋅ A12064940 MLS

Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level includes 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen, making it ideal for guests, multi-generational living, or maximizing short term rental income.Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.

74049 Overseas Highway, Islamorada

3 Beds ⋅ 2 Baths ⋅ A12066813 MLS

Your Keys retreat! A cozy open-concept home featuring modern finishes, a renovated kitchen, and abundant natural light. Situated in an exclusive community with a marina, resort-style pool, boat ramp, and sports courts. Ideal as a primary residence or a vacation getaway in Key Largo!

94825 Overseas, Key Largo

3 Beds ⋅ 2 Baths ⋅ A12066638 MLS

Extensively renovated CBS pool home in desirable Duck Key featuring luxury finishes, smart-home technology, and contemporary coastal design. This beautifully updated Florida Keys retreat offers an exceptional blend of modern style and island living, highlighted by a dramatic multi-story screened porch that captures natural light, tropical breezes, and seamless indoor-outdoor living. The designer kitchen serves as the heart of the home, showcasing an oversized quartz waterfall island, premium smart appliances, custom cabinetry, and a spacious walk-in pantry. Throughout the home you'll find soaring tongue-and-groove ceilings, oversized interior doors, designer lighting, and high-end finishes throughout. The luxurious bathrooms have been thoughtfully redesigned with custom tile work, floating vanities, LED mirrors, premium fixtures, and spa-inspired showers that create a true resort-style experience. Thoughtful upgrades and attention to detail are evident throughout every room. Outside, enjoy a beautiful new pool surrounded by an expansive paver deck, creating the perfect setting for entertaining or relaxing in the Florida Keys sunshine. The impressive screened outdoor living area offers a unique architectural feature, providing an inviting space to enjoy island breezes year-round. Elevated construction provides abundant enclosed storage and versatile additional space ideal for hobbies, fitness equipment or storage needs. Professionally prepared engineering plans for a future expansion are also available, offering additional flexibility and value for future owners. Located in the sought-after community of Duck Key, just minutes from world-class boating, fishing, waterfront dining, and resort amenities. A rare opportunity to own a fully renovated luxury home in one of the Florida Keys' most desirable island communities.

209 Corsair Road, Duck Key

5 Beds ⋅ 6 Baths ⋅ A12064822 MLS

“Discover Sunset Paradise – a stunning new construction Gulf-front retreat built in 2023 in the heart of Marathon, Florida Keys. This turnkey, fully furnished single-family home offers approximately 3,219 square feet of luxurious living space on a spacious 0.43-acre lot with direct open-water Gulf access.Boasting 5 bedrooms and 4.5 bathrooms (main house plus a separate guest cabana with A/C), this property sleeps up to 12 and is ideal for large families, multi-generational getaways, or premium vacation rentals. Built with durable concrete construction (CBS), it features bright, coastal-inspired interiors with panoramic Gulf views, a gourmet kitchen, and expansive living areas that flow seamlessly to outdoor entertainment spaces. It also includes a 4-car garage.Step outside to your private waterfront oasis: enjoy a beautiful heated pool with jacuzzi (perfect for year-round use, including winter), covered decks, and a massive 74-foot concrete dock ideal for boating, fishing, kayaking, or simply relaxing by the water. Additional highlights include a pergola, fish-cleaning station, bait freezer, and ample room for boat trailer storage.This home is a proven income producer with an active short-term rental license and established bookings through VRBO, Airbnb, and the highly regarded local management company Florida Keys Vacation Rentals. It is sold fully furnished and turnkey – ready for immediate enjoyment or continued rental success.

735 50 Street Unit Gulf, Marathon, Key West

4 Beds ⋅ 4 Baths ⋅ A12064763 MLS

Experience luxury waterfront living at 8 Poisonwood Road, a beautifully renovated 4-bedroom, 4-bathroom CBS residence on a private, direct ocean-access canal in one of Key Largo's most desirable neighborhoods. Built for the ultimate boating lifestyle, this exceptional home features a metal roof, impact windows and doors, and over 3,900 square feet of thoughtfully designed living space.The open-concept second level showcases panoramic canal views and seamlessly blends the chef's kitchen, dining area, and spacious living room. Premium finishes include granite countertops and backsplashes, a custom wet bar, glass railings, warm LED lighting, and roller shades throughout.The private third-floor primary suite features a spa-inspired bath with dual vanities, a frameless glass shower, a large walk-in closet, and a private balcony with peek-a-boo ocean views. The first floor offers three guest bedrooms, two full baths, a spacious entertainment area, and convenient poolside access to a full bathroom.Enjoy over 700 square feet of covered outdoor living, a designer pool completed in 2026, professionally landscaped low-maintenance grounds, a 60-foot concrete dock, concrete water-entry steps, and three canal aerators for crystal-clear water. With immediate access to world-class fishing, diving, snorkeling, and the Atlantic Ocean, this exceptional property delivers the very best of the Florida Keys waterfront lifestyle.

8 Poisonwood, Key Largo

3 Beds ⋅ 2 Baths ⋅ A12063421 MLS ⋅ Puerta Del Sol BLDG.

Charming 3-bedroom, 2-bath elevated home in the heart of Marathon. This beautifully maintained property captures the relaxed island lifestyle with open living spaces, vaulted ceilings, and coastal finishes throughout. Enjoy outdoor living under the covered entertaining area complete with lounge seating, dining space, bar, and grill. The low-maintenance yard features tropical landscaping, plenty of parking, and room for a boat or trailer. Perfect as a vacation home or full-time residence, located minutes from beaches, marinas, and local dining. Live the Keys dream!

230 66th Street Unit Ocean, Marathon

6 Beds ⋅ 6 Baths ⋅ A12064182 MLS

Crafted for waterfront living, this custom 6-bedroom, 5.5-bath bayfront estate offers expansive Florida Bay views, seamless indoor-outdoor living, and an unparalleled boating lifestyle. Offered fully furnished and turnkey, recent owner enhancements include elegant marble flooring throughout the lobby and staircase. Walls of glass and 20-foot bifold doors flood the home with natural light, while an elevator provides access to all three levels. The second level is home to the primary suite with Florida Bay views, a custom beverage bar, a private retreat space, and a reimagined boutique-inspired closet with glass-enclosed wardrobes and integrated storage. The spa bath features Spanish porcelain tile, dual vanities, a dual shower, soaking tub, and TOTO toilets. Three additional ensuite guest bedrooms and a laundry room complete this level. The upper level is designed for entertaining with a chef's kitchen featuring Miele appliances, Italian Pedini cabinetry, porcelain countertops, and an oversized island overlooking the living and dining areas. Additional owner enhancements include a glass-enclosed Miele wine gallery, curated designer furnishings, and a new 40K boat lift. KEF audio, integrated security, covered terraces, a saltwater pool, summer kitchen, putting green, and a rooftop terrace complement two additional ensuite guest bedrooms and a powder bath. Outdoors, 125 feet of protected dockage with 40K and 20K boat lifts complete the ultimate Florida Keys waterfront lifestyle.

39 Mutiny Place, Key Largo

4 Beds ⋅ 3 Baths ⋅ B26058151 MLS

This exceptional waterfront estate on a deep water canal with a 50ft dock on a double lot is situated in the heart of Plantation Key. The property features a grand three story residence framed by established palm trees and a striking, patterned paver driveway. The expansive grounds are clean but unplanted, offering a clear blank canvas for you to design your ultimate custom tropical landscaping and privacy screening. The backyard focuses entirely on the water, featuring a lagoon style pool with cascading waterfalls, rock formations, and elevated sun decks. A private waterfront dock provides instant access to boating, fishing, or cruising to the open waters of Florida Bay.

168 INDIAN MOUND Trail, Tavernier

3 Beds ⋅ 2 Baths ⋅ A12061754 MLS

Gorgeous 3 bedroom 2 bathroom home on a spacious corner lot, with plenty of room for boats and RVs. Updated and remodeled bathrooms, open concept kitchen, laundry room and stainless steel appliances . This property is situated in one of the highest elevations in the area, Property is surrounded by beautiful mature trees and it has an in-ground heated pool, lots of space to enjoy the open air, just a block away from the community park and boat ramp. Enjoy ramp access for boat launching, fishing, kayaking or to just take in a spectacular sunset on the water! You can either walk, bike, or take a ride on a golf cart to the park/ramp area. You also have nearby Founder's Park, with excellent recreation, boat ramp access, public beach, a huge pool as well as several local festivals throughout the year, FREE for local residents. Property features a VOLUNTARY HOA, $250 annually. Seller offering $10K in contributions towards buyer's closing costs!

157 Navajo Street, Tavernier

3 Beds ⋅ 3 Baths ⋅ A12061248 MLS

Rare Florida Keys boater's paradise on the golf course! This Marathon waterfront gem offers deep, wide canal access with direct routes to the Gulf and Atlantic, plus a 100-ft composite dock outfitted with a fish cleaning station, 12,000 lb boat lift, and 5,000 lb davit — bring the yacht, the sportfish, and all the toys. Enjoy front-row views of the Florida Keys Country Club golf course, just minutes from Sombrero Beach, the crown jewel of Marathon's beaches.Outdoor living is unmatched: a heated 26' x 13' pool, screened porch, fully equipped outdoor kitchen, and outdoor shower create the ultimate entertaining setup year-round. The oversized 6" reinforced concrete driveway with rebar is engineered to handle heavy equipment, trailers, or yacht storage with ease.Inside, impact windows and doors provide peace of mind and efficiency throughout. A convenient downstairs half kitchen adds flexibility for guests or multigenerational living, complemented by a legal downstairs enclosure — rare, permitted living space that adds real value.Golf course views, beach proximity, and true yacht-ready waterfront — this Keys property checks every box. Schedule your private showing today!

2557 Sombrero Boulevard, Marathon

3 Beds ⋅ 3 Baths ⋅ A12057185 MLS

Welcome to your dream escape in the Florida Keys. This spacious 3-bedroom, 3-bath oceanfront townhome in the highly sought-after Bonefish Yacht Club Townhomes offer the perfect blend of coastal and laid-back island living. Set within an intimate marina community of just 34 residences nestled among lush tropical landscaping, this home feels both private and resort-like and also conveys with a deeded boat slip in Bonefish Marina (B-34). Enter through the foyer and up to two levels of open living, with 1,769 sq. ft. thoughtfully oriented for comfort, water views, and easy entertaining. The chef's kitchen features generous cabinetry, ample counter space, and an inviting eat-in island that flows seamlessly into the main living area, where sliding glass doors open to a spacious waterfront balcony overlooking the Key Colony Channel. The primary suite is a serene retreat with its own private balcony, walk-in closet, and ensuite bath, while two additional bedrooms offer flexible space for guests, family, or a home office, each with access to well-appointed baths. On the ground level, a private garage and generous storage provide the perfect place for fishing gear, paddleboards, and all your Keys lifestyle essentials. Residents enjoy a temperature-controlled pool, expansive sun deck, tiki lounge with wet bar, tennis and pickleball courts, and a private sandy beach. New roof in 2023 and new A/C in 25 with 12 year warranty.

95 Coco Plum Dr & Slip B-34 Unit 4, Marathon

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