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$1,121,665
3Beds
3Baths
1,591Sqft
Big Pine, Florida, 33043, United States
Wake up to endless water views and wind down with breathtaking Keys sunsets at this peaceful island retreat. Set on a quiet corner lot, this 3-bedroom, 3-bath home offers the perfect blend of privacy, comfort, and classic Keys charm.
Homes and Land
$1,121,665
3759 Seagrape Street
3Beds
3Baths
1,591Sqft
Big Pine, Florida, 33043, United States
Wake up to endless water views and wind down with breathtaking Keys sunsets at this peaceful island retreat. Set on a quiet corner lot, this 3-bedroom, 3-bath home offers the perfect blend of privacy, comfort, and classic Keys charm. A wraparound screened in porch with six sets of sliding glass doors fills the home with natural light and cooling tropical breezes, while rich pecky cypress accents add warmth and character throughout. Across the street, a community park provides a serene green space, and for boaters, the location is idealjust minutes to Pine Channel, about 20 minutes by boat to the Content Keys, and easy access to the Atlantic. Outdoor living shines with a spacious screened patio, a 10' x 10' tiki hut for entertaining, and a 10,000-lb boat lift ready for your next adventure. Located in the highly sought-after Port Pine Heights neighborhood, this exceptionally tranquil community is known for its natural beauty and frequent visits from Key deer. With a residents-only park just around the corner and some of the most peaceful surroundings in the Lower Keys, this is more than a homeit's the island lifestyle you've been dreaming of.
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Homes and Land
$1,121,665
3759 Seagrape Street
3Beds
3Baths
1,591Sqft
$1,121,665
Big Pine, Florida, 33043, United States
$2,900,000
3Beds
4Baths
1,700Sqft
Big Pine, Florida, 33043, United States
Spectacular Open-Water Retreat with Unmatched Sunset View This exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve.
Homes and Land
$2,900,000
29581 Richard Road
3Beds
4Baths
1,700Sqft
Big Pine, Florida, 33043, United States
Spectacular Open-Water Retreat with Unmatched Sunset View This exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve. The property features over 200 feet of concrete seawall, a 35' x 15' boat basin making it ideal for waterfront living. Step inside this impressive concrete-built home, where water views surround the main living area. The spacious living room showcases vaulted wood ceilings and abundant natural light. The home offers three en-suite bedrooms, plus an additional full bath conveniently located off the kitchen. Designed for true Florida Keys living, the resort-style in-ground pool and tiki hut are perfectly positioned to take in the spectacular western sunset views, creating an unforgettable setting for relaxing evenings and waterfront entertaining. Additional highlights include: Impact windows and slidersLarge attached garage Separate utility/storage building Exceptional privacy Direct ocean access This is a rare opportunity to own a private, west-facing luxury estate that seamlessly blends modern construction, boating convenience, and breathtaking sunset views.
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Homes and Land
$2,900,000
29581 Richard Road
3Beds
4Baths
1,700Sqft
$2,900,000
Big Pine, Florida, 33043, United States
$899,995
2Beds
2Baths
798Sqft
Key West, Florida, 33040, United States
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.
Homes and Land
$899,995
3625 Seaside Drive
2Beds
2Baths
798Sqft
Key West, Florida, 33040, United States
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.
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Homes and Land
$2,950,000
3Beds
2Baths
2,312Sqft
Plantation Key, Florida, 33070, United States
Dont let the address fool you, this home has easy bay access! Welcome to relaxed waterfront living in the Village of Islamorada, where open water views and nightly sunsets set the tone for an effortless Keys lifestyle. This inviting three-story home is designed to capture light, breezes, and the beauty of its surroundings.
Homes and Land
$2,950,000
149 Lake Road
3Beds
2Baths
2,312Sqft
Plantation Key, Florida, 33070, United States
Dont let the address fool you, this home has easy bay access! Welcome to relaxed waterfront living in the Village of Islamorada, where open water views and nightly sunsets set the tone for an effortless Keys lifestyle. This inviting three-story home is designed to capture light, breezes, and the beauty of its surroundings.Inside, vaulted tongue-and-groove ceilings and an airy open floor plan create a warm coastal ambiance, while expansive impact windows and doors frame sweeping water views. The main living spaces flow seamlessly together, making it easy to entertain or simply unwind after a day on the water. Three comfortable bedrooms and two baths provide plenty of room for family and guests.Step outside to enjoy open terraces on both levels--perfect for morning coffee, sunset cocktails, or watching boats glide by on their way to Florida Bay just minutes away. Boaters will appreciate the concrete dock and quick access to some of the Keys most spectacular waters.Thoughtfully equipped with impact windows and doors and a whole-house generator for peace of mind, this waterfront retreat blends comfort, practicality, and the timeless charm of Islamorada living--where every evening ends with a sunset over the bay.
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Homes and Land
$2,950,000
149 Lake Road
3Beds
2Baths
2,312Sqft
$2,950,000
Plantation Key, Florida, 33070, United States
$2,800,000
3Beds
3Baths
2,049Sqft
Key West, Florida, 33040, United States
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.
Homes and Land
$2,800,000
508 Grinnell Street
3Beds
3Baths
2,049Sqft
Key West, Florida, 33040, United States
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.
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Homes and Land
$2,800,000
508 Grinnell Street
3Beds
3Baths
2,049Sqft
$2,800,000
Key West, Florida, 33040, United States
$4,695,000
3Beds
3Baths
1,973Sqft
Lower Matecumbe, Florida, 33036, United States
Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-level living with elevator access in the highly sought-after waterfront Keys community. Completed in 2024/2025 by renowned local contractor CBT Construction, the home blends modern luxury with a relaxed tropical elegance.
Homes and Land
$4,695,000
241 Tollgate Boulevard
3Beds
3Baths
1,973Sqft
Lower Matecumbe, Florida, 33036, United States
Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-level living with elevator access in the highly sought-after waterfront Keys community. Completed in 2024/2025 by renowned local contractor CBT Construction, the home blends modern luxury with a relaxed tropical elegance. The state-of-the-art kitchen is designed to impress as well as maintain functionality. The kitchen features quartz finishes, top-quality appliances, a professional gas range and oven, ice maker, and expansive cabinetry and counter space. This kitchen is ideal for entertaining, gathering, and everyday living especially if you have more than one chef in the house! A generous counter bar provides additional seating for guests and spectators alike. Three exceptionally spacious bedrooms create a comfortable retreat, with two offering ensuite baths, all complementing the homes gracious island-inspired design. The ground floor enclosure has approximately 900sq ft of additional useable space for enjoyment hobby and workshop and garage areas. Exact square footage not warranted.Boating enthusiasts will appreciate protected yacht dockage on Hurricane Creek, complete with a 15,000 lb boat lift and approximately 5-6 feet of controlled depth, depending on tide. Additional highlights include a swimming pool, whole-home generator, and private access to the owners neighborhood park. Owner occupied--advance notice is appreciated. Schedule your private showing today.
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Homes and Land
$4,695,000
241 Tollgate Boulevard
3Beds
3Baths
1,973Sqft
$4,695,000
Lower Matecumbe, Florida, 33036, United States
$3,995,000
4Beds
4Baths
2,669Sqft
Key Largo, Florida, 33037, United States
This resort-style oceanfront home is the perfect vacation home or primary residence, offering unparalleled views of the Atlantic Ocean along with a heated pool and hot tub, beach area with wood fire pit, propane tiki torches, pavilion, and deep water dockage with a boat lift. The spacious interior features 4 bedrooms and 4 bathrooms across three levels.
Homes and Land
$3,995,000
802 Bonito Lane
4Beds
4Baths
2,669Sqft
Key Largo, Florida, 33037, United States
This resort-style oceanfront home is the perfect vacation home or primary residence, offering unparalleled views of the Atlantic Ocean along with a heated pool and hot tub, beach area with wood fire pit, propane tiki torches, pavilion, and deep water dockage with a boat lift. The spacious interior features 4 bedrooms and 4 bathrooms across three levels. The main living area on the second floor includes high wood ceilings, panoramic ocean views, an oceanfront balcony, and a bedroom with an adjacent bathroom. The third floor is dedicated to the primary suite, complete with a private balcony for a birds-eye view. The ground level includes two additional bedrooms with en-suites and a large laundry room. Additional highlights include a garage for boating and dive gear, impact windows and doors, gated entry, paver driveway, and parking for multiple vehicles. Located at mile marker 95 in Key Largo, enjoy world-class fishing and diving right from your backyard.
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Homes and Land
$3,995,000
802 Bonito Lane
4Beds
4Baths
2,669Sqft
$3,995,000
Key Largo, Florida, 33037, United States
$3,900,000
4Beds
4.5Baths
2,807Sqft
Key Largo, Florida, 33037, United States
Welcome to The Lookout, a premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart of Key Largo. Centrally located to all that Key Largo has to offer, yet discreetly set within a private, gated community, this residence offers a rare balance of accessibility and seclusion.
Homes and Land
$3,900,000
48 E Playa Largo Boulevard
4Beds
4.5Baths
2,807Sqft
Key Largo, Florida, 33037, United States
Welcome to The Lookout, a premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart of Key Largo. Centrally located to all that Key Largo has to offer, yet discreetly set within a private, gated community, this residence offers a rare balance of accessibility and seclusion. Built to the highest structural standards to withstand coastal conditions, the home reflects a commitment to longevity, performance, and refined design.The residence is offered fully furnished with a designer-grade interior package, delivering a cohesive, turnkey experience. Clean architectural lines, premium materials, and thoughtfully curated interiors define the living spaces, while expansive ocean-facing terraces extend the homes livability outdoors. Open-concept living and dining areas are designed for both everyday use and entertaining, with each bedroom suite offering privacy and comfort.Owners enjoy exclusive access to a private clubhouse, resort-style pool, and landscaped grounds. Directly across the street, Playa Largo Resort & Spa, Autograph Collection provides full access to world-class dining, spa services, beach amenities, and water-based activities, enhancing both lifestyle and rental appeal. The community is intentionally limited in scale, preserving a residential atmosphere while benefiting from resort infrastructure just moments away.A defining attribute of this offering is the flexibility of ownership and rental strategy. New owners may elect to participate in the Playa rental management program with full resort privileges or self-manage and rent independently, providing uncommon control over use and income. With nightly rentals permitted, this premier oceanfront residence is equally suited as a refined weekend retreat, a rental income opportunity, or a long-term hold in one of the Florida Keys most established resort communities. Quiet, secure, and impeccably positioned.
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Homes and Land
$3,900,000
48 E Playa Largo Boulevard
4Beds
4.5Baths
2,807Sqft
$3,900,000
Key Largo, Florida, 33037, United States
$4,500,000
4Beds
4.5Baths
3,756Sqft
Key Largo, Florida, 33037, United States
Mahogany Bay in Key Largo is comprised of 4 Balinese style homes located on almost 5 beautiful acres on the Florida Bay. This Bali inspired home commands privacy along with spectacular water and sunset views from the great room, gorgeous kitchen, large open terraces, and the primary suite with a private terrace. There are 2 additional guest suites.
Homes and Land
$4,500,000
101954 Overseas Highway
4Beds
4.5Baths
3,756Sqft
Key Largo, Florida, 33037, United States
Mahogany Bay in Key Largo is comprised of 4 Balinese style homes located on almost 5 beautiful acres on the Florida Bay. This Bali inspired home commands privacy along with spectacular water and sunset views from the great room, gorgeous kitchen, large open terraces, and the primary suite with a private terrace. There are 2 additional guest suites. The interior features an open floor plan with 9 ceilings, impact resistant doors and windows, high end stainless appliances, custom millwork, quartz countertops, marble and wood flooring, spa-like bathrooms, and 8 interior wood doors. This homes exterior features include a private heated pool with spa, covered area for parking, and additional poolside seating for entertaining, privacy landscaping, metal roofing, garage, and plenty of parking in the area behind the home. This special property also includes a separate one bedroom, one bath guest cottage complete with living area, kitchenette, and an expansive porch all appointed with the same design and custom finishes as the main house.
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Homes and Land
$4,500,000
101954 Overseas Highway
4Beds
4.5Baths
3,756Sqft
$4,500,000
Key Largo, Florida, 33037, United States
$10,900,000
6Beds
4.5Baths
4,394Sqft
Lower Matecumbe, Florida, 33036, United States
A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1/2 acre lot with panoramic water views from every room. Offering 220 linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge.
Homes and Land
$10,900,000
186 & 165 Bayview Drive
6Beds
4.5Baths
4,394Sqft
Lower Matecumbe, Florida, 33036, United States
A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1/2 acre lot with panoramic water views from every room. Offering 220 linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys.Private showings available by appointment.
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Homes and Land
$10,900,000
186 & 165 Bayview Drive
6Beds
4.5Baths
4,394Sqft
$10,900,000
Lower Matecumbe, Florida, 33036, United States
$3,800,000
4Beds
4.5Baths
2,574Sqft
Upper Matecumbe Key Islamorada, Florida, 33036, United States
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios.
Homes and Land
$3,800,000
82779 Old Highway
4Beds
4.5Baths
2,574Sqft
Upper Matecumbe Key Islamorada, Florida, 33036, United States
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime.Some interior photos are from comparable villas within the property and not exact villa listed.
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Homes and Land
$3,800,000
82779 Old Highway
4Beds
4.5Baths
2,574Sqft
$3,800,000
Upper Matecumbe Key Islamorada, Florida, 33036, United States
$3,100,000
3Beds
3.5Baths
1,488Sqft
Lower Matecumbe, Florida, 33036, United States
Artfully updated canal-front pool home on beloved Sunset Drive! This delightful residence was recently remodeled from top to bottom by a local and renowned builder and features a bright open floor plan, modern kitchen with stainless steel appliances, and coastal-inspired finishes throughout. Bonus pre-firm 1BA/1BA downstairs.
Homes and Land
$3,100,000
114 Sunset Drive
3Beds
3.5Baths
1,488Sqft
Lower Matecumbe, Florida, 33036, United States
Artfully updated canal-front pool home on beloved Sunset Drive! This delightful residence was recently remodeled from top to bottom by a local and renowned builder and features a bright open floor plan, modern kitchen with stainless steel appliances, and coastal-inspired finishes throughout. Bonus pre-firm 1BA/1BA downstairs. The exterior offers a private pool, spacious lounging areas, and substantial dockage suitable for a large vessel, providing immediate access to open water. Clean lines, natural light, and thoughtful updates create a move-in-ready retreat to relax and absorb the peacefulness of island life. Dont miss this delightful waterfront offering in one of the Florida Keys most desirable boating locations!
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Homes and Land
$3,100,000
114 Sunset Drive
3Beds
3.5Baths
1,488Sqft
$3,100,000
Lower Matecumbe, Florida, 33036, United States
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