Islamorada Real Estate

Islamorada Real Estate

Welcome to Islamorada, a charming city located in Monroe County, Florida. Known as the "Village of Islands," Islamorada is a tropical paradise nestled in the heart of the Florida Keys. With its stunning natural beauty and laid-back island lifestyle, it's no wonder that Islamorada is a popular destination for both tourists and residents alike.

One of the main attractions of Islamorada is its breathtaking beaches and crystal-clear turquoise waters. Whether you're a fan of sunbathing, swimming, or water sports like snorkeling and fishing, you'll find plenty of opportunities to enjoy the great outdoors here. The area is home to several state parks and nature reserves, where you can explore lush mangrove forests, spot unique wildlife, and take in panoramic views of the surrounding islands.

In addition to its natural beauty, Islamorada also offers a vibrant cultural scene. The city is dotted with art galleries, boutique shops, and delicious seafood restaurants, where you can sample the local cuisine. The community hosts various events and festivals throughout the year, celebrating everything from music and art to food and fishing.

For those seeking a more active lifestyle, Islamorada offers a range of recreational activities. The city is renowned for its world-class fishing, with abundant opportunities for both offshore and backcountry angling. Whether you're a seasoned angler or a novice, the local charters and guides will ensure you have a memorable fishing experience.

Overall, Islamorada is a picturesque city that offers a unique blend of natural beauty, cultural attractions, and outdoor adventures. Whether you're looking for a vacation spot or a place to call home, Islamorada has something for everyone. Come and discover the enchanting charm of this tropical paradise in the Florida Keys.

Newest Listings in Islamorada

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 ⋅ 4 Baths ⋅ B26059747 MLS

LIVE, WORK & PLAY IN ISLAMORADA | RARE SC COMBO ZONING! Income + residence at MM 82.8 on high-visibility Overseas Hwy! Walk to beach, shops & dining. Street-to-street 50x150 lot w/ Old Hwy rear access & parking for work trucks, trailers & boats. COMMERCIAL OFFICE: Fully outfitted CBS bldg w/ 6" concrete roof, dual mini-splits, full bath, separate meter, 3-phase electric & impact shutters. RESIDENTIAL COMPOUND: 3B/3.5B CBS home split into 4 spaces (A, B, C & flex room w/ half bath). Impact glass, 2024 roof, 2025 panel/water heater & updated ACs. Outdoor laundry & furnishings incl. Offered turn-key w/ 40-yr business assets. NDA req'd. DO NOT DISTURB OCCUPANTS! APPT ONLY. Square Footage Breakdown: Total finished living area of 2,036 sq. ft. includes 1,560 sq. ft. residential compound + 476 sq. ft. commercial office building (2,629 sq. ft. total gross area under roof).

82891 Overseas Highway, Islamorada

A12061389 MLS ⋅ 24.9961° N Latitude BLDG.

Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily lot, giving you both immediate rental income and room to grow. In Islamorada, it's rare to find side-by-side multifamily parcels in such a convenient, desirable neighborhood. This CBS triplex is 2,409 sq ft on a 7,500 sq ft lot, with 3 rental units (1/1, 1/1, 2/2), full kitchens and baths, abundant on-site parking, and great outdoor living areas. Units 1 and 3 were renovated with updated interiors that attract solid tenants. In 2025, the dock electric was upgraded with a dedicated meter for dock power, one on each property. Next door, 121 Monroe Drive is an additional multifamily parcel of about 7,500 sq ft, ready for development. Add more units, a pool, covered parking with storage, or enhance outdoor spaces to create a cohesive compound and boost rental revenue. Multifamily waterfront land in Islamorada is limited, and demand for quality rentals remains strong. With recent upgrades and easy access to the mainland, this combined offering is a great opportunity for investors, 1031 buyers, or owner-operators who want a flexible Keys property with income today and room for future build-out and long-term appreciation. Free access to Founders Park, with sandy beach, swimming pool, boat ramp, playground, tennis, pickleball, walking paths, sports fields, dog park and daily fun activities and regular events.

127 & 121 Monroe Drive Unit 13, Islamorada

1 Beds ⋅ 1 Baths ⋅ A12056036 MLS

Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

81801 Old Hwy 754 Unit 754, Islamorada

6 Beds ⋅ 8 Baths ⋅ A12056007 MLS

Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Highway, Islamorada

4 Beds ⋅ 6 Baths ⋅ A12050889 MLS

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views. An arcaded hallway with a hand-tiled barrel-vaulted ceiling connects interiors featuring Italian finishes, exquisite marble details, five fireplaces, hand-painted ceiling frescoes, and a one-of-a-kind imported tile roof. Florentine windows, Juliette balconies, wrought-iron railings, copper gutters, and hand-carved marble corbels. The floor plan includes four bedrooms, with three guest suites on the main level and a private third-floor primary retreat. The chef's kitchen is appointed with top of the line appliances, a walk-in pantry, and dedicated prep kitchen. A pass-through window connects to the outdoor kitchen and covered dining. A formal dining room with a hand-painted ceiling fresco, wellness room, sauna, theater, and billiards lounge. Outside, an infinity-edge pool, sunken gazebo with swim-up seating, putting green, fountains, and tropical landscaping. Deep dockage, sand beach, and clear waters provide immediate access to fishing, diving, snorkeling, and boating. An air-conditioned boat room, skiff ramp, 4,000+ SF collector's garage, elevator servicing all 3 levels, C4/Sonos smart home, secure walled & gated grounds.

75090 Overseas Highway, Islamorada

3 Beds ⋅ 3 Baths ⋅ A12051290 MLS ⋅ Venetian Shores BLDG.

OCEAN ACCESS WATERFRONT OPPORTUNITY IN VENETIAN SHORES! Immaculate 2-story CBS concrete home offering the ultimate Florida Keys lifestyle! Situated on a 100' wide deep-water canal with NO FIXED BRIDGES and direct access to both the Atlantic Ocean and Florida Bay via Snake Creek, this is a boater's dream. Minutes to open water with a private dock featuring power and davits, perfect for large boats. This spacious home features 3 bedrooms, 2.5 baths with a flexible floor plan. The first floor offers 2 bedrooms, 1 full bath, family room, and bar area, while the second floor features the primary suite, oversized kitchen, dining room, laundry room, and half bath to maximize the spectacular waterfront views. Enjoy breathtaking sunsets and tropical breezes from the expansive wraparound covered porch. Additional features include beautiful hardwood floors, an oversized kitchen ideal for entertaining, brand-new saltwater pool (2026), three large exterior storage rooms, circular driveway, and fresh exterior paint (2025). Lovingly maintained and in immaculate condition, this home is ready for your personal updates to create the ultimate Keys retreat. Located in the highly desirable Venetian Shores community, known for its deep, wide canals, outstanding boating access, and optional homeowners association. Whether you're looking for a full-time residence, weekend getaway, or luxury waterfront escape, this is a rare opportunity to own in one of Islamorada's premier boating communities.

107 Valencia Drive, Islamorada

4 Beds ⋅ 5 Baths ⋅ A12032087 MLS

Private Bayfront Estate in desirable Islamorada offering a serene ambiance on an oversized parcel of pristine bayfront with breathtaking sunsets and unobstructed panoramic views of the Florida Bay. This exceptional waterfront retreat features an irreplaceable protected boat basin, concrete jetty, and T-dock providing superior deep-water dockage. Encompassing 4,000 square feet of beautifully designed living space, this remarkable residence includes 4 spacious bedrooms and 4.5 bathrooms. This home showcases an inviting kitchen and multiple expansive living areas all thoughtfully designed for ultimate comfort and entertaining, ideal for hosting family and guests or enjoying a private coastal escape. Step outside to your own tropical sanctuary with unforgettable sunsets, year-round outdoor living, and the sparkling waters of Florida Bay creating the ultimate Florida Keys lifestyle. A rare opportunity to own in one of Islamorada's most exclusive waterfront settings.

88110 Overseas Highway, Islamorada

7 Beds ⋅ 9 Baths ⋅ A11962802 MLS

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five generous en-suite guest bedrooms, a powder room, and a large laundry room. The lower level offers a separate one bed en-suite with its own entrance and patio. A Media room with adjoining bathroom is the ideal flex space. A 1,600 square foot three car garage and a carport area completes the lower level. All told, there is nearly 25,000 square feet under roof cover. The estate's tropical grounds are designed to complement the home's architecture. A private floating dock offers unimpeded views of Florida Bay. Located in the heart of Islamorada, this property offers rare walkability to some of the village's most recognizable attractions. This location allows you unparalleled access to the best of Islamorada's dining, entertainment, and waterfront lifestyle. Isla House represents a rare opportunity to own one of Islamorada's most unrivaled, captivating, and serene waterfront estates—a sanctuary of elegance, craftsmanship, and timeless island charm.

Islamorada

7 Beds ⋅ 10 Baths ⋅ A12022973 MLS

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly four acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The home's architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. The interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio.

82768 Overseas Highway, Islamorada

3 Beds ⋅ 3 Baths ⋅ A11857499 MLS ⋅ Port Antigua BLDG.

Rarely available, turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of IslamoradaTucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully designer-updated 3+ bedroom, 3.5-bath home delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge.Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. The interior staircase provides easy access to the home's main living areas. The property boasts 90 feet of deep-water dockage with immediate access to both the bay and the Atlantic Ocean--no bridges.The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles -- an uncommon convenience in this area.What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle. Whether you're seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals. Some Exterior Photos are AI-generated.

122 Court Contessa, Islamorada

2 Beds ⋅ 3 Baths ⋅ A11880379 MLS ⋅ Anglers Reef Un 111 BLDG.

Your dream getaway in the heart of the Florida Keys! This light-filled, spacious 2br/2bth home is located in the highly sought-after Angler's Reef community in Islamorada. Fully furnished, tastefully decorated and turnkey, this well-maintained property is perfect for ocean lovers or savvy investors alike.With over 12 years in a successful vacation rental program and an active vacation rental license, this home offers immediate income potential. Just bring your suitcase and start enjoying or earning from day one! Oceanfront community pool and marina, two private sandy beaches, gated community, pet friendly and direct ocean access. As a personal tropical retreat or a high-performing investment property, this home has it all. Don’t miss your chance to own a piece of paradise!

111 Anglers Way, Islamorada

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