Islamorada FL Real Estate & Homes for Sale

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Beds:
3
Baths:
4.00
Sq.Ft.:
2,374
Status:
NEW LISTING
MLS#:
A12073183
Type:
Other
Subdivision:
PORT ANTIGUA PLAT NO 5 &
Lot size:
0.13 Acres
Year built:
2021
Courtesy: The Keyes Company Lourdes Martin-Rosa 305-505-8050
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ADDITIONAL INFORMATION

Rarely available turnkey Deepwater Boater's retreat with a Private Bayside beach in the heart of the fishing capital of the world. Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in the Florida Keys, this fully renovated 3-bedroom, 3.5-bath concrete residence 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. Designed for serious boaters, the property boasts 90 FT of deepwater dockage with immediate access to both the bay and the Atlantic Ocean - NO BRIDGES, no delays, just open water within minutes. The home is completely updated with a seamless indoor-outdoor flow ideal for entertaining or extended stays. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles - an uncommon convenience in this area. What truly sets this home apart is access to a rare, highly coveted private bayside beach, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle that is seldom available in a single property. 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.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,596
Status:
Active
MLS#:
A12064940
Type:
Other
Subdivision:
LOWER MATECUMBE BEACH
Lot size:
0.5 Acres
Year built:
1970
Courtesy: Luxe Properties Kimberly Farias 786-339-6583
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ADDITIONAL INFORMATION

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 offers a handicap-friendly layout, with a 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen. 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.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,036
Status:
Active
MLS#:
B26059747
Type:
Residential
Subdivision:
OCEAN VIEW
Lot size:
0.17 Acres
Year built:
1958
Courtesy: Keys Properties of the PB's 561-330-4802
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ADDITIONAL INFORMATION

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).

Beds:
4
Baths:
4.00
Sq.Ft.:
2,624
Status:
Active
MLS#:
620828
Type:
Multi-Family
Subdivision:
Mat Ocean Beach (75.0)
Lot size:
0.53 Acres
Year built:
1970
Courtesy: Homecoin.com 888-400-2513
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ADDITIONAL INFORMATION

Welcome to your own private slice of Atlantic Ocean Paradise!. an Oversized Oceanfront Lot! Over 1/2 acre (23,500 sqf) Estate boasting 100 feet of absolute astonishing direct shoreline with ever changing crystal clear turquoise Atlantic Ocean waters plus an additional 100'x200' (20,000 sqf) of submerged Ocean Land. Arrive to expansive grounds, your own Private dock and what many consider exceptional,rare and extraordinary among Oceanfront homes/estates in all Islamorada is your own Private concrete boat ramp! Ideal for launching your pontoon, bay boat or jet skis with ease plus a generous parking for RVs, boats, trailers, and guests. Inside the main residence, discover three beautiful bedrooms and three full baths, with Spectacular Ocean view from most every room, complemented by a charming separate cottage with its own bedroom, bathroom, and full kitchen ideal for guest!Step outside to a sparkling chill/heated swimming pool where you can sip your morning coffee or evening cocktail while overlooking endless ocean views and the natural coastal wildlife. It's exclusive , it's unique and it's a true gem!. It's The Kind Of Oceanfront setting with a True Resort-Like Feel Everyday!.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
A12054415
Type:
Other
Subdivision:
EXECUTIVE BAY CLUB
Year built:
1980
Courtesy: Related ISG International Real Samira Ramirez 786-426-5767
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ADDITIONAL INFORMATION

Turnkey and beautifully updated townhouse in the prestigious Executive Bay Club in Islamorada! This spacious 2-bedroom, 2-bath residence and a loft with room for two additional beds,offers 1,344 sq. ft. of living space. Ideally located in one of the community’s best locations, with no parking directly in front for added privacy. Enjoy newly renovated resort-style amenities, a new community roof, giving peace of mind. Adjacent to Founders Park and nestled in a bay-to-ocean community, this property is perfect as a vacation retreat, primary residence, or income-producing investment. Start creating unforgettable family memories—and generate rental income when not in use. Paradise is here. Schedule your private showing today and experience the Florida Keys lifestyle for yourself. Welcome HOME -Island Living at it's best! + unforgettable sunsets

Beds:
6
Baths:
8.00
Sq.Ft.:
6,577
Status:
Active
MLS#:
A12056007
Type:
Other
Subdivision:
MATECUMBE OCEAN BAY SEC 2
Lot size:
0.77 Acres
Year built:
2025
Courtesy: American Caribbean Real Estate
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ADDITIONAL INFORMATION

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.

Beds:
1
Baths:
1.00
Sq.Ft.:
550
Status:
Active
MLS#:
A12056036
Type:
Other
Subdivision:
Strattons
Year built:
1988
Courtesy: American Caribbean Real Estate Joy Martin 305-451-4008
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,800
Status:
Active
MLS#:
A12051550
Type:
Single Family
Subdivision:
WHITE MARLIN BEACH SEC 1
Lot size:
0.16 Acres
Year built:
1990
Courtesy: Move Miami, LLC. 305-301-0525
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ADDITIONAL INFORMATION

Waterfront Islamorada Pool Home with Private Beach Access to White Marlin Beach. Experience the best of the Florida Keys in this beautifully updated waterfront retreat in Islamorada, designed to accommodate up to 12 guests and perfect for family vacations, multigenerational gatherings, or extended stays. The spacious layout features a main living area upstairs, while the ground level offers a private 2-bedroom, 1-bath guest suite with its own kitchenette and separate entrance, ideal for guests, extended family, or a dedicated workspace. Step outside to enjoy the newly completed pool, breathtaking waterfront views, and private beach access to White Marlin Beach. Designed for relaxation and entertaining, the property offers inviting outdoor living spaces, a barbecue grill, and smart TVs throughout the home. A golf cart is also available for rent, making it easy to explore the area. Conveniently located near some of Islamorada’s most popular waterfront restaurants, marinas, fishing charters, shops, and local attractions, this home places you at the center of the Florida Keys lifestyle. Whether you're boating, fishing, kayaking, dining at local favorites, or simply relaxing poolside while taking in spectacular sunsets, this exceptional waterfront home offers the perfect combination of comfort, convenience, and island living.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
620621
Type:
Other
Subdivision:
Strattons (82.5)
Year built:
2014
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

50' X 22' boat slip at the World famous Lor E Lei marina. Excellent in-town location, you know you're going to boat over here anyway so you might as well tie up for the night! Enjoy the sunsets, unwind, Uber home, or use for your fishing business, so many possibilities. A rare find.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,632
Status:
Active
MLS#:
A12051290
Type:
Other
Subdivision:
VENETIAN SHORES NO 2
Lot size:
0.16 Acres
Year built:
1994
Courtesy: Keller Williams Legacy Patty Accorto 954-804-3149
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A11927254
Type:
Single Family
Subdivision:
Safety Harbor
Year built:
1968
Courtesy: Paradise Florida Keys Real Est 305-393-0523
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ADDITIONAL INFORMATION

Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,016
Status:
Active
MLS#:
A11928539
Type:
Condo
Subdivision:
PLANTATION BY THE SEA
Year built:
1977
Courtesy: Main Assets Corp 954-447-2988
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ADDITIONAL INFORMATION

Beautifully maintained 2-bedroom, 2 bath townhouse condo located oceanside in the heart of Islamorada. This turn-key residence offers effortless island living with no updates needed—simply move in and enjoy. The home features a new A/C system installed in 2022, new appliances added in 2024, and fully replaced air ducts completed in 2024 for improved comfort and efficiency. Impact windows throughout provide security and storm protection, while electric blackout blinds add convenience and privacy. The interior is bright, clean, and exceptionally well cared for, making it ideal as a primary residence, vacation home, or weekend retreat. Situated in one of the most desirable areas of the Florida Keys, this property offers the perfect blend of comfort, style, and coastal living. Don’t miss the opportunity to own a truly turn-key condo in beautiful Islamorada. Schedule your showing today.

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A11952214
Type:
Condo
Subdivision:
Palms of Isla (80.0)
Year built:
1976
Courtesy: LoKation 954-545-5583
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ADDITIONAL INFORMATION

Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic. Perfectly situated near Bud & Mary's Marina and just minutes from Islamorada's most beloved restaurants, this location captures the very best of island living. This property is truly a must-see—and it's priced to sell. Seller will consider all reasonable offers.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,464
Status:
Active
MLS#:
A11955613
Type:
Single Family
Subdivision:
PORT ANTIGUA PLAT NO 2
Lot size:
0.38 Acres
Year built:
1986
Courtesy: Pine River Realty, LLC. 786-556-3434
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ADDITIONAL INFORMATION

Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

Beds:
7
Baths:
9.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A11962802
Type:
Single Family
Subdivision:
Upper Matecumbe
Year built:
2026
Courtesy: American Caribbean Real Estate 305-451-4078
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ADDITIONAL INFORMATION

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.

Beds:
6
Baths:
7.00
Sq.Ft.:
6,680
Status:
Active
MLS#:
A11972240
Type:
Single Family
Subdivision:
ISLAMORADA, TOWNSITE OF
Lot size:
1.68 Acres
Year built:
2005
Courtesy: Beycome of Florida LLC 804-656-5007
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ADDITIONAL INFORMATION

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
A11973593
Type:
General Commercial
Year built:
1951
Courtesy: Paradise Florida Keys Real Est 305-393-0523
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ADDITIONAL INFORMATION

This is an exceptionally rare chance to secure a versatile mixed use commercial property in Islamorada's most established business corridors. With prominent highway frontage, excellent visibility, and steady traffic exposure, theses three building are ideally positioned for a wide range of commercial uses. making it an appealing option for investors and owner-operators. The building features a practical, adaptable layout suitable for professional offices, medical or wellness services, boutique retail, administrative operations, or specialty businesses. Large front-facing windows bring in natural light and enhance street presence, creating an inviting entry point for customers and clients. The footprint also supports the creation of private offices, treatment rooms, or storage areas, allowing businesses to tailor the space to their operational needs. On-site parking adds significant value, providing convenient access for customers and employees--an important advantage in Islamorada's commercial zones. Excellent signage opportunities ensure strong brand exposure. Easy ingress and egress make the location suitable for both destination-based and walk-in business models. Surrounded by established businesses, restaurants, marinas, and residential neighborhoods, the property benefits from a diverse and active customer base. Islamorada's strong local economy enhances the long-term appeal of this location. Totally renovated in 2019. Business is not part of thr sale.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,337
Status:
Active
MLS#:
A12006598
Type:
Condo
Subdivision:
EXECUTIVE BAY CLUB
Year built:
1980
Courtesy: Compass Florida, LLC 305-316-0660
View additional info

ADDITIONAL INFORMATION

Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys’ most desirable communities.

Beds:
2
Baths:
2.00
Sq.Ft.:
989
Status:
Active
MLS#:
A11994749
Type:
Condo
Subdivision:
PLANTATION BY THE SEA
Lot size:
2.16 Acres
Year built:
1977
Courtesy: The Keyes Company 305-247-7221
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ADDITIONAL INFORMATION

Location! Location! Location! Beautiful 2 bedroom 2 bath furnished condo. Located in oceanfront building in Islamorada. Dock available for boat to load and unload. Elevator to first floor. Master has a large balcony and walk in closet. Additional storage unit on main floor. Covered parking, guest parking, heated pool, 400 ft. fishing pier/dock for loading and unloading only, club house, gym, sauna, BBQ picnic/grassy area. Available May 1, 2026. LANDLORD OFFERING ALL UTILITIES INCLUDED FOR 3100 (WIFI CABLE WATER ELECTRIC ETC)

Beds:
8
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12009440
Type:
Single Family
Subdivision:
Strattons Subdivision Pb2-
Year built:
1984
Courtesy: LoKation 954-545-5583
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ADDITIONAL INFORMATION

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. Seller will consider all reasonable offers. The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Bird's Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle. A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys.

Beds:
1
Baths:
1.00
Sq.Ft.:
550
Status:
Active
MLS#:
B26036550
Type:
Condo
Subdivision:
HOTEL CONDOMINIUM AT CHEEC
Year built:
1988
Courtesy: United Realty Group, Inc 561-235-2127
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ADDITIONAL INFORMATION

Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income producing condotel in the Sport Fishing Capital of the World. This 27-acre oceanfront Islamorada resort set in a lush tropical landscape has everything from fine dining restaurants, spa and wellness, fitness center, three resort style pools, two tiki bars, par 3 golf course, four lighted tennis courts, pickleball, basketball, bicycles, huge pier for fishing, kayaking, paddleboarding, and more. This top floor corner unit is a beautifully appointed one king bedroom with expansive master bath, kitchen and private screened in balcony. Accomplished on-site professional management has delivered high occupancy and rental rates far above many other lodging properties in the Keys!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,000
Status:
Active
MLS#:
A12035866
Type:
Condo
Subdivision:
PLANTATION BY THE SEA
Lot size:
2.16 Acres
Year built:
1977
Courtesy: The Keyes Company 305-247-7221
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ADDITIONAL INFORMATION

WAKE UP TO A BREATHTAKING OCEAN VIEW IN THIS RARELY AVAILABLE OCEANFRONT CONDO COMMUNITY! LOCATED ON MILLIONAIRE'S ROW IN HIGHLY DESIRABLE ISLAMORADA/PLANTATION KEY. ENJOY A SPARKLING OCEANFRONT HEATED POOL, A 300 FT FISHING PIER/DOCK TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING. KAYAK STANDS FOR THOSE THAT PREFER NON MOTORIZED ACTIVITIES. BBQ'S WITH COMPLIMENTARY PROPANE, AND THE COMMUNITY ROOM OFFERS A FULL KITCHEN WITH POOL TABLE, FLAT SCREEN TV, CARD TABLE, AND TABLE TENNIS. LIVE LIKE YOU ARE ON VACATION ALL YEAR LONG! INSIDE THE CONDO, BOASTS AN OPEN CONCEPT LIVING SPACE, 2 LARGE BEDROOMS THAT ARE FULLY FURNISHED. ALL YOU NEED ARE YOUR CLOTHES AND YOUR TOILETRIES! CONDO OFFERS THE PERFECT BLEND OF COMFORT AND CONVENIENCE, UPDATED KITCHEN WITH WOOD CABINETRY, RECESSED LIGHTING, AND AMPLE STORAGE. THE SPLIT-BEDROOM LAYOUT PROVIDES ADDED PRIVACY, WHILE THE PRIMARY SUITE BOASTS A STUNNING OCEAN VIEW. ADDITIONAL FEATURES INCLUDE A NEW HOT WATER HEATER, A HALF BATH ON THE MAIN LEVEL, A DESIGNATED COVERED PARKING SPACE, GUEST PARKING, ENJOY RESORT-STYLE AMENITIES INCLUDING A HEATED POOL, COMMUNITY ROOM WITH KITCHEN, DOCK/FISHING PIER, FITNESS CENTER, SAUNA, AND MORE. IDEALLY LOCATED TO ENJOY ALL THE FLORIDA KEYS HAS TO OFFER, THIS MOVE-IN-READY RENTAL IS THE PERFECT PLACE TO CALL HOME! ALSO, CLOSE BY AND WITHIN WALKING DISTANCE IS FOUNDER'S PARK, SHOPS, AND POPULAR GOURMET RESTAURANTS. LANDLORD WILL DECREASE RENT TO '$3,000 IF TENANT WISHES TO PAY THEIR OWN ELECTRIC.

Beds:
5
Baths:
7.00
Sq.Ft.:
5,153
Status:
Active
MLS#:
620457
Type:
Single Family
Subdivision:
Safety Harbor (74.0)
Lot size:
0.23 Acres
Year built:
2017
Courtesy: Coastal Realty of the Florida Keys 305-664-0077
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ADDITIONAL INFORMATION

Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed living space, set just 2 lots from the bay and across from a tranquil mangrove preserve that enhances both privacy and natural beauty. Boaters will love the setup - 100' of dockage with 2 elevator boat lifts (20,000lb and 15,000lb), plus easy access to Everglades National Park and the Atlantic Ocean through the 65' Channel 5 Bridge. Inside, the home feels open, bright, and refined. There are 5 ensuite bedrooms and 2 half baths, each bedroom featuring its own ductless A/C along with the central system. The primary suite includes a cozy sitting area, his-and-hers closets, and partial bay views. A secondary primary suite opens directly to the pool deck, offering privacy for guests or family. The top level centers around a stunning great room with vaulted ceilings, fireplace, and a chef's kitchen with high-end appliances - the perfect setting for entertaining. On the lower level, a relaxed family room with fireplace and wet bar creates another comfortable gathering space. Additional features include laundry on both floors, an elevator, 2-car garage, and gated circular drive. Out back, the saltwater pool, outdoor kitchen, and sound system create a true resort-style atmosphere. The east-facing orientation means warm morning sunshine, shady afternoons, and gentle ocean breezes. With CBS construction, metal roof, whole house generator and impact windows and doors, this home blends luxury, comfort, and peace of mind. This is waterfront living for those who value both elegance and ease - the Keys lifestyle at its finest.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12046316
Type:
Other
Subdivision:
MATECUMBE SANDY BEACH
Lot size:
0.74 Acres
Courtesy: Pine River Realty, LLC. 786-556-3434
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ADDITIONAL INFORMATION

A truly once in a generation opportunity to build your dream estate in the heart of Islamorada's coveted Lower Matecumbe. This exceptional vacant homesite is one of the few remaining parcels of its size available in all of Islamorada, offering an incredibly rare combination of breathtaking ocean views and expansive wide canal views. Encompassing over 32,000 square feet, this extraordinary property provides the perfect canvas for a custom waterfront residence designed to capture spectacular sunrises, refreshing ocean breezes, and the unmatched beauty of the Florida Keys. Its unique setting offers the best of both worlds--open water vistas in the front and a wide canal in the rear, creating an unparalleled lifestyle for boating enthusiasts and those seeking privacy, space, and unforgettable scenery. Opportunities to acquire a property of this caliber have become increasingly scarce in Islamorada, where large vacant parcels are exceptionally limited. Whether you're envisioning a private family compound or a legacy waterfront estate, this one-of-a-kind offering represents a chance to create something truly extraordinary in one of the Florida Keys' most desirable destinations.

Beds:
6
Baths:
3.00
Sq.Ft.:
2,684
Status:
Active
MLS#:
620458
Type:
Multi-Family
Subdivision:
Misc Upper Matacumbe (82.0)
Lot size:
0.18 Acres
Year built:
1958
Courtesy: Cypress Realty, Inc. 239-275-3321
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ADDITIONAL INFORMATION

3 plex ( 3 separate units) in the heart of downtown Islamorada. A total of 6 bedrooms and 3 baths. Two of the units are remodeled. Walk to Shopping, Boutiques, Bars, Restaurants, World Wide Sportsman/Bas Pro Shops, Florida Keys Brewery. Or take your street legal golf cart. Currently fully rented on annual leases. Would make great 30 days rentals or really great employee housing. Do not miss this opportunity. Two separate electric meters and one water meter.

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.


Andrea Conner, License #298336, Xome Inc., License #C24582, [email protected], 844-400-9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 7506


The data relating to real estate for sale on this web site comes in part from the IDX Program of the High Country Association of REALTORS®. The data is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.



Islamorada 33036 Real Estate

Islamorada is located in Florida. Islamorada, Florida 33036has a population of 7,051. Islamorada 33036 is less family-centric than the surrounding county with 16.45% of the households containing married families with children. The county average for households married with children is 20.65%.

The median household income in Islamorada, Florida 33036 is $77,423. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Islamorada 33036 is 55.3 years.

Islamorada Weather

The average high temperature in July is 89.3 degrees, with an average low temperature in January of 62 degrees. The average rainfall is approximately 47.7 inches per year, with 0 inches of snow per year.

Islamorada Map

Islamorada Real Estate Market Conditions

  • Median sales price

    $1,002,500
    26.6%
    change since last quarter
  • # Active listings

    229
    30-day change

Islamorada Schools and Demographics

Education near Islamorada, FL

City County
High School Graduates 96.13 92.07
College Degree - 2 year 10.44 7.93
College Degree - 4 year 39.54 35.69
Graduate Degree 11.76 9.88
Expenditures per Student 20,907 20,907
Students per Teacher 14.7 14.7

Elementary Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Big Pine Academy PK - 08 177 12.6 33043
Gerald Adams Elementary School PK - 05 544 13.3 33040
Horace O'Bryant School PK - 08 1,059 14.3 33040
Key Largo School PK - 08 847 14.1 33037
Key West Montessori Charter School KG - 08 149 16.6 33040
Monroe Virtual Instruction Program (District Provided) KG - 05 6 33040
Ocean Studies Charter KG - 05 104 11.2 33070
Plantation Key School PK - 08 435 12.8 33070
Poinciana Elementary School PK - 05 663 15.1 33040
Sigsbee Charter School KG - 08 478 17.1 33040
Stanley Switlik Elementary School PK - 05 566 14.2 33050
Sugarloaf School PK - 08 526 15 33042
Treasure Village Montessori Charter School PK - 08 213 14.2 33036

Middle Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Glynn Archer Elementary School PK - 05 394 15.8 33040

High Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Coral Shores High School 09 - 12 733 17.4 33070
Key West Collegiate School 09 - 12 78 15.3 33040
Key West High School 09 - 12 1,193 16.8 33040

Ungraded Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
* Keys Center 08 - 12 11 11 33040
Academic Connections for Excellence 06 - 12 11 33040
Adult/Vocational/Community Education AE - AE 0 33040
Hurricane Island Outward Bound 06 - 12 12 33037
Marathon School 06 - 12 667 18.5 33050
Monroe Virtual Academy (Course Offerings) 06 - 12 0 33040
Monroe Virtual Franchise 06 - 12 4 33040
Monroe Virtual Instruction Program KG - 12 0 33040

Demographics near Islamorada, FL 33036

Zip Code City
Neighborhood Type Small town
Population 7,051 82,244
Population Density 1,094 84
Median Age 55.3 48
People per Household 2.2 2.4
Median Household Income 77,423 73,153
Average Income per Capita 60,315 50,050

Real estate near Islamorada