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Cudjoe Key Luxury Real Estate, Luxury Homes For Sale

(95) PROPERTIES

COUNTY, FL 33042
$4,950,000
CUDJOE KEY, FL 33042
16750 Old State

6 Beds 5.1 Baths Square Ft: 5208
Single Family Home - MLS#: 555501
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

Unforgettable Keys Estate located behind a security gate, with lush tropical landscape, irrigation, bug mister, whole house generator, total remodel, beautiful views from every room,about 3 acres total.…

MLS 555501

COUNTY, FL 33042
$3,999,000
CUDJOE KEY, FL 33042
1446 Calle Bogota

4 Beds 4 Baths Square Ft: 4706
Single Family Home - MLS#: 556927
Community: Summerland Beach - Mile Marker (MM) 25.0

Situated on the southern tip of world Summerland Key this magnificent home has some of the most stunning views in the Keys. This 4 bedroom 4 bath home was built to perfection with over 4500 Sq Ft under…

MLS 556927

COUNTY, FL 33042
$2,999,999
CUDJOE KEY, FL 33042
974 Flagship

3 Beds 3.1 Baths Square Ft: 4200
Single Family Home - MLS#: 552235
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

Spectacular Oceanfront Location. Built like a fortress, concrete home with high impact windows & doors. Bronze doors welcome you at this estate home. Experience the unsurpassed watercolor views of the…

MLS 552235

COUNTY, FL 33042
$2,395,000
CUDJOE KEY, FL 33042
865 E Shore

5 Beds 4 Baths Square Ft: 3127
Single Family Home - MLS#: 556777
Community: Summerland Beach - Mile Marker (MM) 25.0

Casa Blanca. This Key West inspired ocean front estate sits on approximately 1/2 acre of pristine beach front property. Surrounded by flourishing tropical vegetation, this home has one of the few real…

MLS 556777

COUNTY, FL 33042
$2,350,000
CUDJOE KEY, FL 33042

4 Beds 3.1 Baths
Single Family Home - MLS#: 556152
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

MLS 556152

COUNTY, FL 33042
$2,350,000
CUDJOE KEY, FL 33042
20824 W 9TH

4 Beds 4.2 Baths Square Ft: 4069
Single Family Home - MLS#: 555147
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Remarkable newer built home in prestigious Cudjoe Gardens. With a very unique layout, enjoy 4 bdrms, 4 bth, 2 halfbaths, a separate guest quarter, office, gym, library loft, high ceiling living rm, fans…

MLS 555147

COUNTY, FL 33042
$1,950,000
CUDJOE KEY, FL 33042
1243 Ocean

4 Beds 3 Baths Square Ft: 2006
Single Family Home - MLS#: 553078
Community: Summerland Beach - Mile Marker (MM) 25.0

Tropical Sunrises - Immerse yourself in gorgeous sunrises over the Caribbean Ocean from this beautiful Summerland Beach location. This open water, pre-firm home sits on one of the largest parcels of land…

MLS 553078

COUNTY, FL 33042
$1,900,000
CUDJOE KEY, FL 33042
17 E Shore

5 Beds 5 Baths Square Ft: 3877
Single Family Home - MLS#: 552668
Community: Summerland Estates - Mile Marker (MM) 25.0

Amazing opportunity. A huge estate property located in the Summerland Beach area. The property includes approximately 13 acres and encompasses both sides of East Shore Drive and has three existing houses.…

MLS 552668

COUNTY, FL 33042
$1,900,000
CUDJOE KEY, FL 33042
185 La Fitte

2 Beds 2 Baths Square Ft: 1284
Single Family Home - MLS#: 556472
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

Extraordinary chance to purchase 3 LOTS on the open water with epic sunrise views & 180 ft of great deep water boating access. Enjoy your privacy with the numerous palms, concrete wall and electronic…

MLS 556472

COUNTY, FL 33042
$1,899,000
CUDJOE KEY, FL 33042
16606 Holly

3 Beds 3 Baths Square Ft: 1800
Single Family Home - MLS#: 556741
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

Magnificent point lot in Prestigious South Point. This huge gated property features lush landscaping and a custom heated pool. There is over 300' of open water frontage and 122' of protected seawall with…

MLS 556741

COUNTY, FL 33042
$1,799,000
CUDJOE KEY, FL 33042
25360 1st

4 Beds 3.1 Baths Square Ft: 3161
Single Family Home - MLS#: 556739
Community: Summerland Beach - Mile Marker (MM) 25.0

Big Boat Alert! Deepest Protected Dockage in the Lower Keys!! Magnificent CBS home with over 3000 SqFt under air. Legal guest quarters downstairs;bar; storage;garage;workshop;cathedral ceilings;billiards…

MLS 556739

COUNTY, FL 33042
$1,750,000
CUDJOE KEY, FL 33042
17011 Marlin , Unit West

3 Beds 3 Baths Square Ft: 1538
Single Family Home - MLS#: 555644
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

PARADISE FOUND! One of a Kind Open Water Estate Property, Great Boating, basin/ramp, extremely private ½ + acre with the most sought after southwestern location in Sugarloaf. 300 ft of exclusive PRIVATE…

MLS 555644

COUNTY, FL 33042
$1,699,999
CUDJOE KEY, FL 33042
22614 Jolly Roger

4 Beds 2.1 Baths Square Ft: 1924
Single Family Home - MLS#: 554912
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

This property consists of 2 lots directly facing the Atlantic Ocean. 4 bedrooms 2 1/2 baths with cathedral ceilings, screened porch, open BBQ deck, walk around deck, heated custom pool, dock, screened…

MLS 554912

COUNTY, FL 33042
$1,699,000
CUDJOE KEY, FL 33042
633 Sawyer

3 Beds 3 Baths Square Ft: 2710
Single Family Home - MLS#: 553503
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Stunning Open Water Views from this three bedroom three bath two story home. The property faces the southeast to catch the tropical breezes. Custom built with marble bathrooms, Jerusalem stone counter…

MLS 553503

COUNTY, FL 33042
$1,699,000
CUDJOE KEY, FL 33042
22572 Jolly Roger

5 Beds 3 Baths Square Ft: 2511
Single Family Home - MLS#: 553530
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

''Oceanfront Playground'' 5 Bed/3 Bath home with over 2000 Sq.Ft. of living area. This home boasts breath taking views of the Atlantic Ocean, 140 feet of waterfront, heated pool, private beach, 2 docks,…

MLS 553530

COUNTY, FL 33042
$1,650,000
CUDJOE KEY, FL 33042
385 South Point

3 Beds 3 Baths Square Ft: 2532
Single Family Home - MLS#: 536033
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

This custom home features the award winning architecture and landscape design work of D’Asign Source! Enjoy easy access to deep water, substantial enclosed storage and a pool from this stunning 3 bedroom…

MLS 536033

COUNTY, FL 33042
$1,599,000
CUDJOE KEY, FL 33042
855 Ea SHORE

4 Beds 4 Baths Square Ft: 3564
Single Family Home - MLS#: 543768
Community: Summerland Beach - Mile Marker (MM) 25.0

The magic of the ocean combined with the extensive lush landscaping offers complete privacy in this colossal estate. Features of the estate include 4 bedrooms and 4 bathrooms with 2 master suites, 2 zone…

MLS 543768

COUNTY, FL 33042
$1,577,000
CUDJOE KEY, FL 33042
1195 Thatch

3 Beds 3 Baths Square Ft: 2134
Single Family Home - MLS#: 555971
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

With unlimited open water views,300 ft of shoreline & a beautiful tropical pool with waterfall,this unique custom home has it all! Main house is 2/2 w/large modern kitchen, open living and dining areas…

MLS 555971

COUNTY, FL 33042
$1,500,000
CUDJOE KEY, FL 33042
16550 Old State Rd 4A

3 Beds 3 Baths Square Ft: 2845
Single Family Home - MLS#: 552094
Community: Sugarloaf Beach - Mile Marker (MM) 17.0

Tranquility Cove, a secluded 2 acre oceanfront gated estate on prestigious Sugarloaf Beach & just minutes to the magic of Key West. Resort-style property offers a lagoon-style pool w/waterfall, fountain…

MLS 552094

COUNTY, FL 33042
$1,500,000
CUDJOE KEY, FL 33042
5420 Dorn

3 Beds 2.1 Baths Square Ft: 1881
Single Family Home - MLS#: 556142
Community: Dorns Sub - Mile Marker (MM) 28.0

Gated estate quality property with 3.5 acres on beautiful, pristine Big Torch Key. This home consists of main house with multiple living areas, and a detached 4 car garage with mother-in-law quarters.…

MLS 556142

COUNTY, FL 33042
$1,500,000
CUDJOE KEY, FL 33042
21640 Overseas Hwy

4 Beds 5 Baths Square Ft: 4044
Single Family Home - MLS#: 553740
Community: Sacarma - Mile Marker (MM) 21.0

Spectacular 4 BR 5 BA oceanfront estate sprawling over 1.2 Acres w/sandy beach. Picture perfect ocean views & breezes are enjoyed from all living areas & on the upper & lower screened verandas. Fully…

MLS 553740

COUNTY, FL 33042
$1,499,000
CUDJOE KEY, FL 33042
20952 6th

3 Beds 2 Baths Square Ft: 2190
Single Family Home - MLS#: 548237
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Gorgeous custom built 3 bedroom 2 bath CBS home located in prestigous Cujoe Gardens. The exterior of this home features a heated swimming, brick paver patio, seawall with davit pads and a garage. The…

MLS 548237

COUNTY, FL 33042
$1,425,000
CUDJOE KEY, FL 33042
16624 Croton

3 Beds 3 Baths Square Ft: 2574
Single Family Home - MLS#: 555667
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

Gorgeous sunsets over the bay at this stunning 3 BR home located on one of Sugarloaf's premier point lots in prestigious South Point. The resort-style home boasts lots of amenities incl:waterfront pool…

MLS 555667

COUNTY, FL 33042
$1,350,000
CUDJOE KEY, FL 33042
19551 Indian Mound

3 Beds 3 Baths Square Ft: 2828
Single Family Home - MLS#: 556769
Community: Indian Mound Estates - Mile Marker (MM) 19.5

Truly remarkable oceanfront estate on Sugarloaf Key.Built to the highest standards in 2010. Almost 1 acre on Bow Channel. Sandy beach area, boat slip & lift. Home is gorgeous with hand picked granite…

MLS 556769

COUNTY, FL 33042
$1,295,000
CUDJOE KEY, FL 33042
1090 Gulf

2 Beds 2 Baths Square Ft: 1711
Single Family Home - MLS#: 552632
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

Point Estate! Rare point, private, gated property in Summerland Isles! Nearly 1/2 acre surrounded by water on 3 sides. Beautiful, completely remodeled, granite countertops, tigerwood floors, CBS/concrete…

MLS 552632

COUNTY, FL 33042
$1,249,000
CUDJOE KEY, FL 33042
717 La Fitte

3 Beds 3.1 Baths Square Ft: 2716
Single Family Home - MLS#: 556208
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

OPEN WATER SUNRISES in Jolly Roger Estates where oceanside boat access is one of the best in the Lower Keys. Fall in love with this Mediterranean-inspired residence,renovated with exquisite detail and…

MLS 556208

COUNTY, FL 33042
$1,195,000
CUDJOE KEY, FL 33042
95 Sacarma

5 Beds 3 Baths Square Ft: 2310
Single Family Home - MLS#: 553111
Community: Sacarma Bay - Mile Marker (MM) 21.0

Great Investment Opportunity! Resort-style oceanfront home w/beach, pool, dock & stunning sunset views over ocean. The beautifully decorated 5 BR home boasts a large great room w/open kitchen, fireplace…

MLS 553111

COUNTY, FL 33042
$1,150,000
CUDJOE KEY, FL 33042
66 Airport

4 Beds 2.1 Baths Square Ft: 2860
Single Family Home - MLS#: 553417
Community: Summerland Key Cove - Mile Marker (MM) 25.0

FLY IN AND BE FISHING IN THE ATLANTIC OCEAN IN MINUTES. This exceptional canal front home is located on the Summerland Air Strip. Four bedrooms, 2 & 1/2 baths plus a large office and an enclosed air plane…

MLS 553417

COUNTY, FL 33042
$1,085,000
CUDJOE KEY, FL 33042
28425 Jolly Roger

3 Beds 2.1 Baths Square Ft: 2656
Single Family Home - MLS#: 556089
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

Exceptionally designed with detailed elegance. This newly constructed stunning 3 level concrete home with impact windows & metal roof has panoramic ocean views with a private quiet location, & exceptional…

MLS 556089

COUNTY, FL 33042
$1,050,000
CUDJOE KEY, FL 33042
22388 Jolly Roger

3 Beds 2 Baths Square Ft: 1888
Single Family Home - MLS#: 554632
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

Soothing endless open water view makes time stand still while the stars twinkle brilliantly at night. Observe nature from the large open deck or from the cool interior of this 3 bdrms 2bth new home. Open…

MLS 554632

COUNTY, FL 33042
$999,000
CUDJOE KEY, FL 33042
22910 Hawkins

2 Beds 2.1 Baths Square Ft: 2048
Single Family Home - MLS#: 555160
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

Gorgeous Sunset views over the Bay at this 2,000 SF bay front home. Located on a gated 13,000 SF point lot at the end of a quiet neighborhood. Colossal great room w/high ceilings. Large porch offers great…

MLS 555160

COUNTY, FL 33042
$999,000
CUDJOE KEY, FL 33042
482 Brown

4 Beds 2 Baths Square Ft: 1912
Single Family Home - MLS#: 555495
Community: Ramrod Shores - Mile Marker (MM) 27.0

Dazzling sunrises & sunsets over the open water at this pristine bay front property. This architecturally stunning home offers 2,000 SF w/4 BR's, 2 BAs & Study. Gorgeous bay views are enjoyed from the…

MLS 555495

COUNTY, FL 33042
$999,000
CUDJOE KEY, FL 33042
21090 5th East

3 Beds 3 Baths Square Ft: 2398
Single Family Home - MLS#: 556738
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Spectacular Custom Built Canal Front 3 bedroom 3 bath home, granite counters custom kitchen with Five Star Convection Oven Dual Fuel Gas Burners Electric Oven Kitchen Aid frig & microwave & dishwasher,…

MLS 556738

COUNTY, FL 33042
$999,000
CUDJOE KEY, FL 33042
630 Bay Shore

3 Beds 3 Baths Square Ft: 2872
Single Family Home - MLS#: 554323
Community: Silver Shores Est - Mile Marker (MM) 27.0

Breathtaking open water views and stunning sunsets from this 2,872 sq. ft. 3 bedroom/3 bath home. Soaring ceilings and 9' sliding glass doors in the great room frame the sparkling torquoise blue gulf…

MLS 554323

COUNTY, FL 33042
$999,000
CUDJOE KEY, FL 33042
20942 6th , Unit West

3 Beds 3 Baths Square Ft: 2772
Single Family Home - MLS#: 553684
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Deep Water Access minutes to Ocean or Back country, Gorgeous Custom Built 2772 sq ft CBS Home sits on a 15,600 sq ft lot with 110' concrete seawall/dock + davits. Back of home faces the Southern Exposure.…

MLS 553684

COUNTY, FL 33042
$995,000
CUDJOE KEY, FL 33042
917 E Shore

2 Beds 2 Baths Square Ft: 1496
Single Family Home - MLS#: 554668
Community: Summerland Beach - Mile Marker (MM) 25.0

Huge Price Reduction! Your Private Tropical Resort Location. This estate plot is located in prestigious Summerland Beach, a community of beach front multi-million dollar homes. The large ocean front property…

MLS 554668

COUNTY, FL 33042
$995,000
CUDJOE KEY, FL 33042
1147 Flagship

3 Beds 2 Baths Square Ft: 2058
Single Family Home - MLS#: 551132
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

PANORAMIC OPEN WATER VIEWS right from your roof top balcony! Just seconds todeep water access, flow through swimming canal. This 3BD/2BA Summerland Cove home offers: cathedral ceilings, open floor plan,…

MLS 551132

COUNTY, FL 33042
$975,000
CUDJOE KEY, FL 33042
546 E Caribbean

3 Beds 3 Baths Square Ft: 2240
Single Family Home - MLS#: 547705
Community: Summerland Key Cove - Mile Marker (MM) 25.0

PRICE REDUCED on this MILLION DOLLAR VIEW HOME, Must see inside this is not a drive by. Owner Motivated,Bring all offers! Home is located in Summerland Key's most coveted community.3BD/3BA,Ocean Front…

MLS 547705

COUNTY, FL 33042
$900,000
CUDJOE KEY, FL 33042
359 La Fitte

4 Beds 3 Baths Square Ft: 3057
Single Family Home - MLS#: 556221
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

MLS 556221

COUNTY, FL 33042
$899,000
CUDJOE KEY, FL 33042
543 Dogwood

4 Beds 3 Baths Square Ft: 2372
Single Family Home - MLS#: 556762
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

Fantastically Constructed 4 bedroom 3 bath estate with beautiful views of the open water. This CBS home boasts concrete poured floors, open floor plan and soaring cathedral ceilings. New Kitchen, heated…

MLS 556762

COUNTY, FL 33042
$899,000
CUDJOE KEY, FL 33042
17110 La Brisa

2 Beds 2 Baths Square Ft: 1510
Single Family Home - MLS#: 556785
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

Fabulous sunsets over the sound from this impeccably renovated Keys cottage in Sugarloaf Shores. Located on a premier point lot the home boasts over 430' of waterfront w/protected dockage & ramp. Hardwood…

MLS 556785

COUNTY, FL 33042
$899,000
CUDJOE KEY, FL 33042
360 South Point

2 Beds 2 Baths Square Ft: 1428
Single Family Home - MLS#: 547406
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

CBS Open Water. This home has great bones with fantastic sunset views. Concrete seawall, mature landscaping, completely fenced, walk around deck and privacy! This home needs a little work but it is worth…

MLS 547406

COUNTY, FL 33042
$899,000
CUDJOE KEY, FL 33042
21070 5TH

3 Beds 3 Baths Square Ft: 2755
Single Family Home - MLS#: 554980
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Deep Water Access, No Bridges, Gorgeous CBS home, enter into the soaring foyer to the 12 ft ceiling, this 3 bedroom 3 bath with study/bedroom,large kitchen with double sink, granite counters plenty of…

MLS 554980

COUNTY, FL 33042
$890,000
CUDJOE KEY, FL 33042
589 Pattison

3 Beds 2 Baths Square Ft: 1892
Single Family Home - MLS#: 551535
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Beautiful, brand new construction of 2560 sq ft solid concrete home. Outstanding boating, deep water point lot. Beautiful porches throughout and a 1400 sq ft roof top deck with panoramic open water view.…

MLS 551535

COUNTY, FL 33042
$849,000
CUDJOE KEY, FL 33042
695 La Fitte

2 Beds 2 Baths Square Ft: 896
Single Family Home - MLS#: 551985
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

Open water sunrise views of New Found Harbor. Fantastic boating and beautiful water. Concrete home with Hurricane windows. Recent remodle , beautiful kitchen and baths. Tile floors. Sandy beach.Very relaxing…

MLS 551985

COUNTY, FL 33042
$847,000
CUDJOE KEY, FL 33042
840 Lagoon

4 Beds 2.1 Baths Square Ft: 1528
Single Family Home - MLS#: 545981
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

SUNSET DREAMS - Beautiful sunsets are included with this 4 bedroom 2.5 bath home. Located on a clear deep canal second in from openwater. Some features are a large open central living area opening out…

MLS 545981

COUNTY, FL 33042
$814,000
CUDJOE KEY, FL 33042
321 Avenue D

4 Beds 2 Baths Square Ft: 3630
Single Family Home - MLS#: 554461
Community: Summerland Beach - Mile Marker (MM) 25.0

Keys Beach house with cedar & cypress interior wood finishes. Natural sandy beach out front. Expansive open water views and situated to capture the south easterly sea breezes which flow through the house.…

MLS 554461

COUNTY, FL 33042
$799,000
CUDJOE KEY, FL 33042
1175 Thatch

3 Beds 2 Baths Square Ft: 1301
Single Family Home - MLS#: 556834
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

Sit in your screened-in lanai, sip a cup of coffee, while you look look out at amazing open water views. This 3 bedroom, 2 bath CBS home has a fenced, gated, corner double lot with plenty of parking and…

MLS 556834

COUNTY, FL 33042
$799,000
CUDJOE KEY, FL 33042
635 La Fitte

4 Beds 2.1 Baths Square Ft: 2676
Single Family Home - MLS#: 556427
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

BEACHFRONT with Boating! 80 ft of shoreline along the open water with incredible sunrise views. Huge 4 bedroom, 3 bath home w over 2600 sq ft of living space, 2nd floor master suite with panoramic views,…

MLS 556427

COUNTY, FL 33042
$799,000
CUDJOE KEY, FL 33042
90 Sawyer

3 Beds 2 Baths Square Ft: 1972
Single Family Home - MLS#: 556955
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Beautiful custom built canal front home with lush tropical landscaping in a great neighborhood. Open floor plan with custom details that include crown moulding, granite countertops, S.S. appliances, bar,…

MLS 556955



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The data relating to real estate for sale on this website 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 (Shoreline Properties) are marked with the MLS Log and detailed information about them included the name of the listing brokers office.

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