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Cudjoe Key Luxury Real Estate, Luxury Homes For Sale

Browse Cudjoe Key luxury homes and houses, Cudjoe Key ultra luxury single family homes for sale in the FLA Keys. Your source for the most exclusive properties with the hottest Cudjoe Key luxury real estate to hit the market, properties updated daily.

(124) PROPERTIES

COUNTY, FL 33042
$7,495,000
CUDJOE KEY, FL 33042
601 Old State

4 Beds 4.2 Baths Square Ft: 7541
Single Family Home - MLS#: 550240
Community: Sugarloaf Townsite - Mile Marker (MM) 20.0

Remarkable 9 acre open water Sugarloaf Estate. Exquisite 4 BR, 4 BA + 2 half main home boasts, 15 ft. ceilings, marble & cherry floors, dramatic mahogany staircase, formal dining , library & study w/wet… luxury homes

MLS 550240

COUNTY, FL 33042
$5,800,000
CUDJOE KEY, FL 33042
133 Barry

3 Beds 2.1 Baths Square Ft: 5484
Single Family Home - MLS#: 548254
Community: Barry Beach - Mile Marker (MM) 29.0

Luxury Home with 3.4 acres of development land & 1.68 of bay bottom. LDR from Monroe county - 47 ROGOs. luxury homes

MLS 548254

COUNTY, FL 33042
$4,899,000
CUDJOE KEY, FL 33042
1151 Ocean

5 Beds 4.1 Baths Square Ft: 3750
Single Family Home - MLS#: 548226
Community: Summerland Beach - Mile Marker (MM) 25.0

The Crown Jewel of Summerland Beach - Nothing like this fabulous, new, ocean front estate with private yacht basin in prestigious Summerland Beach. Approximately an acre of ocean frontage with incredible… luxury homes

MLS 548226

COUNTY, FL 33042
$4,200,000
CUDJOE KEY, FL 33042
16650 OLD STATE ROAD 4A

7 Beds 5 Baths Square Ft: 3150
Single Family Home - MLS#: 549945
Community: Sugarloaf Sub - Mile Marker (MM) 19.5

Tropical oceanfront compound in gated Esttate Enclave of multi-million dollar homes! 4.8 acres of buildiable upland with 3 homes on open water. Pier/dock on ocean & protected boat dock for up to 3 35'… luxury homes

MLS 549945

COUNTY, FL 33042
$3,950,000
CUDJOE KEY, FL 33042
822 FLAGSHIP

5 Beds 7 Baths Square Ft: 7068
Single Family Home - MLS#: 544938
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

This palatial luxury homes

MLS 544938

COUNTY, FL 33042
$3,900,000
CUDJOE KEY, FL 33042
1223 Ocean

4 Beds 3.1 Baths Square Ft: 3800
Single Family Home - MLS#: 548270
Community: Summerland Beach - Mile Marker (MM) 25.0

Simply the Finest home in the Finest Location! Superbly built & oriented to take advantage of the Direct Atlantic views and prevailing Southeasterly Breezes. This exemplary 4 bedroom 3.5 bath Luxury Estate… luxury homes

MLS 548270

COUNTY, FL 33042
$3,499,000
CUDJOE KEY, FL 33042
1446 Calle Bogota

4 Beds 4 Baths Square Ft: 3984
Single Family Home - MLS#: 549281
Community: Summerland Beach - Mile Marker (MM) 25.0

Nothing Like It! The dream of living on the water on a tropical island has now come together in this spectacular ocean front, point estate. This magnificent property is surrounded by water on 3 sides.… luxury homes

MLS 549281

COUNTY, FL 33042
$3,100,000
CUDJOE KEY, FL 33042
23069 Redfish

5 Beds 5.1 Baths Square Ft: 4430
Single Family Home - MLS#: 550147
Community: Cudjoe Acres - Mile Marker (MM) 21.5

Private gated Keys Estate with open water views. Chestnut & marble floors, gourmet kitchen, elevator, private boat basin, ramp & 2 lifts. Lounge by by your pool or beach. 5 bds/ 5.1 baths + a library… luxury homes

MLS 550147

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

3 Beds 3.1 Baths Square Ft: 4200
Single Family Home - MLS#: 551145
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 the unsurpassed watercolor views of… luxury homes

MLS 551145

COUNTY, FL 33042
$2,999,000
CUDJOE KEY, FL 33042
1355 Ocean

3 Beds 3 Baths Square Ft: 3094
Single Family Home - MLS#: 549685
Community: Summerland Estates - Mile Marker (MM) 25.0

Ocean Mar. Don't dream of a Caribbean life, live it. Where time stands still in our island paradise; Ocean Mar is the perfect home for the outdoor lover and fishing enthusiasts. The large picturesque… luxury homes

MLS 549685

COUNTY, FL 33042
$2,900,000
CUDJOE KEY, FL 33042
753 E Shore

4 Beds 3.1 Baths Square Ft: 3044
Single Family Home - MLS#: 551181
Community: Summerland Beach - Mile Marker (MM) 25.0

Keys resort-style living at it's finest! Stunning oceanfront 1/2 acre estate w/oceanfront pool, sandy beach, 320' dock w/3 lifts & lush tropical landscaping. Newly built home boasts soaring ceilings,… luxury homes

MLS 551181

COUNTY, FL 33042
$2,899,000
CUDJOE KEY, FL 33042
431 E Shore

4 Beds 3 Baths Square Ft: 5042
Single Family Home - MLS#: 543257
Community: Summerland Estates - Mile Marker (MM) 25.0

The moment you arrive at this Open Water Island Retreat, you will know you have found your home in Paradise. This Spacious Estate is an Investors Dream, since it is licensed by Monroe Ct. as a Transient… luxury homes

MLS 543257

COUNTY, FL 33042
$2,700,000
CUDJOE KEY, FL 33042
1263 Ocean

3 Beds 3 Baths Square Ft: 3030
Single Family Home - MLS#: 550704
Community: Summerland Beach - Mile Marker (MM) 25.0

OVERLOOKING THE ATLANTIC Direct Ocean Front 2 Acre Gated Resort in Prestigious SUMMERLAND BEACH ESTATES. Deep water access with your own private weather protected canal & concrete seawall, dockage, boat… luxury homes

MLS 550704

COUNTY, FL 33042
$2,497,000
CUDJOE KEY, FL 33042
516 E Caribbean

4 Beds 3.1 Baths Square Ft: 2358
Single Family Home - MLS#: 549520
Community: Summerland Key Cove - Mile Marker (MM) 25.0

Spectacular Glen Gray design, open water3 bedrooms 3 1/2 baths + study with wet bar &frig, boat basin,2 boat lifts, polysteel poured concrete home, granite counters, every detail is complete in this home,… luxury homes

MLS 549520

COUNTY, FL 33042
$2,495,000
CUDJOE KEY, FL 33042
924 Flagship

5 Beds 3.1 Baths Square Ft: 3800
Single Family Home - MLS#: 550057
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

Crown jewel of Summerland Key, the most sought after island of the lower keys. Located on Flagship Drive on the tip of the island with unobstructed sunset views. Crystal clear water and deep channels… luxury homes

MLS 550057

COUNTY, FL 33042
$2,475,000
CUDJOE KEY, FL 33042
1213 Ocean

4 Beds 3 Baths Square Ft: 2789
Single Family Home - MLS#: 551160
Community: Summerland Beach - Mile Marker (MM) 25.0

A distinctive property that highlights the beauty of the Florida Keys with lush landscaping and exceptional views across Niles Channel from a two story central living area & master suite that also over… luxury homes

MLS 551160

COUNTY, FL 33042
$2,399,000
CUDJOE KEY, FL 33042
855 Ocean

5 Beds 5 Baths Square Ft: 4071
Single Family Home - MLS#: 543768
Community: Summerland Beach - Mile Marker (MM) 25.0

At this Summerland Beach oceanfront estate, there is room for all and plenty to do, or not do. The magic of the ocean combined with the extensive lush landscaping offers complete privacy in this colossal… luxury homes

MLS 543768

COUNTY, FL 33042
$2,200,000
CUDJOE KEY, FL 33042
1243 Ocean

4 Beds 3 Baths Square Ft: 2006
Single Family Home - MLS#: 550131
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… luxury homes

MLS 550131

COUNTY, FL 33042
$1,999,000
CUDJOE KEY, FL 33042
16550 OLD STATE ROAD 4A

4 Beds 3 Baths Square Ft: 2845
Single Family Home - MLS#: 545162
Community: Sugarloaf Beach - Mile Marker (MM) 17.0

MAJOR Reduction-TRANQUILITY COVE offers Privacy & Seclusion, Direct Ocean Atlantic, Fantastic Water & Sunset Views & Fly Fishing Paradise in your Own Back Yard! This spacious 3+ bd 3 bath Estate is designed… luxury homes

MLS 545162

COUNTY, FL 33042
$1,999,000
CUDJOE KEY, FL 33042
1183 Ea Caribbean

3 Beds 3.1 Baths Square Ft: 3019
Single Family Home - MLS#: 550415
Community: Summerland Key Cove - Mile Marker (MM) 25.0

Rare, gated point estate in Summerland Cove. The advantages and views of open water without the problems. Privacy abounds in this fenced, more than 1/4 acre property surrounded by water on 3 sides. Beautiful,… luxury homes

MLS 550415

COUNTY, FL 33042
$1,999,000
CUDJOE KEY, FL 33042
414 E Caribbean

3 Beds 3.1 Baths Square Ft: 2766
Single Family Home - MLS#: 550466
Community: Summerland Key Cove - Mile Marker (MM) 25.0

Newly built 3/3.5 + Den CBS Oceanfront Pool home boasting nearly 3,000 SF! This property is abundant in amenities incl:oceanfront pool w/spa, concrete dock & cut-in boat slip. The well appointed home… luxury homes

MLS 550466

COUNTY, FL 33042
$1,990,000
CUDJOE KEY, FL 33042
21640 Overseas

4 Beds 3 Baths Square Ft: 3255
Single Family Home - MLS#: 550189
Community: Sacarma - Mile Marker (MM) 21.0

Barefoot on your beach, Absolutely spectacular Ocean Front Key West style home. Stunning open water views from your Master Bedroom, bath and extensive private sunset porch. Soaring ceilings and porches… luxury homes

MLS 550189

COUNTY, FL 33042
$1,899,000
CUDJOE KEY, FL 33042
3 Kings Cove

3 Beds 2.1 Baths Square Ft: 1832
Single Family Home - MLS#: 547408
Community: Misc Little Torch KE - Mile Marker (MM) 28.0

Kings Cove. 5 acre estate with one of the finest custom Key West designed homes around. 3 bedrooms 2.5 baths with walkaround porches, beautiful decks, forever views, heated swimming pool, paver decks,… luxury homes

MLS 547408

COUNTY, FL 33042
$1,800,000
CUDJOE KEY, FL 33042
633 SAWYER

3 Beds 3 Baths Square Ft: 3000
Single Family Home - MLS#: 544978
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Stunning open water views from this two story home. The property faces the southeast trade winds to catch the tropical breeze. Custom built with marble bathrooms, Jerusalem stone counter tops and porcelain… luxury homes

MLS 544978

COUNTY, FL 33042
$1,799,000
CUDJOE KEY, FL 33042
22572 Jolly Roger

5 Beds 3 Baths Square Ft: 2511
Single Family Home - MLS#: 550714
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,… luxury homes

MLS 550714

COUNTY, FL 33042
$1,798,000
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 luxury homes

MLS 536033

COUNTY, FL 33042
$1,790,000
CUDJOE KEY, FL 33042
4670 Dorn

2 Beds 2 Baths Square Ft: 1227
Single Family Home - MLS#: 548753
Community: Dorns Sub - Mile Marker (MM) 28.0

Enjoy fabulous open water sunset views from the hot tub in the screened porch, from the sun deck or from the small private beach. 2.65 acres of gated privacy adjacent to State and Federal preserves. Watch… luxury homes

MLS 548753

COUNTY, FL 33042
$1,699,000
CUDJOE KEY, FL 33042
1625 Niles

3 Beds 3 Baths Square Ft: 2026
Single Family Home - MLS#: 550498
Community: Misc Summerland Key - Mile Marker (MM) 25.0

Panoramic ocean views from this immaculate 3 bedroom, 3 luxury homes

MLS 550498

COUNTY, FL 33042
$1,689,000
CUDJOE KEY, FL 33042
717 La Fitte

3 Beds 3.1 Baths Square Ft: 2716
Single Family Home - MLS#: 545457
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, recently renovated with exquisite… luxury homes

MLS 545457

COUNTY, FL 33042
$1,599,000
CUDJOE KEY, FL 33042
917 E Shore

2 Beds 2 Baths Square Ft: 1496
Single Family Home - MLS#: 548204
Community: Summerland Beach - Mile Marker (MM) 25.0

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

MLS 548204

COUNTY, FL 33042
$1,595,000
CUDJOE KEY, FL 33042
14600 Old State

2 Beds 2 Baths Square Ft: 2538
Single Family Home - MLS#: 548426
Community: Sugarloaf Sub - Mile Marker (MM) 19.5

Spectacular 26.1 Acre Oceanfront Estate. Complete with 2 Houses, Horse Stables, Helipad, Electric Security Gate, Dock, and two current permits for docks on open water & deep water access. There is nothing… luxury homes

MLS 548426

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… luxury homes

MLS 548237

COUNTY, FL 33042
$1,495,000
CUDJOE KEY, FL 33042
342 CARIBBEAN

3 Beds 3 Baths Square Ft: 2687
Single Family Home - MLS#: 550742
Community: Summerland Key Cove - Mile Marker (MM) 25.0

Oceanfront Home with spectacular views of the open water. Deep water access, boat lift, boat basin, concrete seawall. Enchanting pool with spa. Paved patio area, drive way paved. Mature landscaping, fenced… luxury homes

MLS 550742

COUNTY, FL 33042
$1,450,000
CUDJOE KEY, FL 33042
321 Avenue D

4 Beds 2 Baths Square Ft: 4630
Single Family Home - MLS#: 550559
Community: Summerland Beach - Mile Marker (MM) 25.0

Great Open Water of Nile Channel and Ocean. 4BD/2BA Timber Framed single family home in Summerland Key. Home also has 1bd/1ba, 1000 sq ft apartment downstairs. luxury homes

MLS 550559

COUNTY, FL 33042
$1,450,000
CUDJOE KEY, FL 33042
22684 Jolly Roger

3 Beds 2 Baths Square Ft: 1896
Single Family Home - MLS#: 540331
Community: Cutthroat Harbor Est - Mile Marker (MM) 23.0

OCEANFRONT CBS HOME WITH CONCRETE FLOORS. Gorgeous Sunsets, large lot and a half, easy to upkeep landscape, wood dock and good boating access. Home features tile throughout, 3 spacious bedrooms, large… luxury homes

MLS 540331

COUNTY, FL 33042
$1,450,000
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,… luxury homes

MLS 551132

COUNTY, FL 33042
$1,300,000
CUDJOE KEY, FL 33042
441 N Airport

3 Beds 2 Baths Square Ft: 2256
Single Family Home - MLS#: 551151
Community: Summerland Key Cove - Mile Marker (MM) 25.0

Summerland Key's premier airport property is now for sale. Sprawling over a waterfront 1/2 acre this hangar home was built by one of the developers of the airport for himself. Custom built CBS w/2-plane… luxury homes

MLS 551151

COUNTY, FL 33042
$1,300,000
CUDJOE KEY, FL 33042
17110 La Brisa

2 Beds 1.1 Baths Square Ft: 1510
Single Family Home - MLS#: 549168
Community: Sugarloaf Shores - Mile Marker (MM) 17.0

''REDUCED TO INCLUDE ADJACENT LOT'' One of the Best/Largest Direct Western SUNSET & OPEN WATER VIEWS in Sugarloaf Shores! Enjoy this Easy Open Water Life Style Home w/Extra Large (2 Lots) 30,250 s/f.… luxury homes

MLS 549168

COUNTY, FL 33042
$1,299,000
CUDJOE KEY, FL 33042
353 Barry

6 Beds 4.1 Baths Square Ft: 3051
Single Family Home - MLS#: 549952
Community: Barry Beach - Mile Marker (MM) 29.0

Awesome Open Water Estate. 4 bedroom 3 bath main home and a 2/2 guest cottage. Open water view with your own private basin to protect you boat. A must see property and priced to sell. luxury homes

MLS 549952

COUNTY, FL 33042
$1,298,000
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

OWNER FINANCING, DIRECT ATLANTIC OCEAN VIEWS Enjoy the breath taking Views from your porches, living room, dining room and kitchen,this home is built for Keys style entertaining both inside and out. Large… luxury homes

MLS 547705

COUNTY, FL 33042
$1,295,000
CUDJOE KEY, FL 33042
20715 5th

4 Beds 3 Baths Square Ft: 3050
Single Family Home - MLS#: 547149
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

CUDJOE GARDENS TROPICAL RETREAT offers over 3,000 sq. ft. of living area and some of the best boating in the Lower Keys. Elegant yet casual, with wonderful space for entertaining. Take a dip in the screened… luxury homes

MLS 547149

COUNTY, FL 33042
$1,249,000
CUDJOE KEY, FL 33042
1023 Lagoon

3 Beds 2 Baths Square Ft: 2043
Single Family Home - MLS#: 550402
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

Grab a Margarita and Put Your Feet Up luxury homes

MLS 550402

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

3 Beds 3 Baths Square Ft: 2228
Single Family Home - MLS#: 548666
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

Over 2200 Sq. Ft. Custom CBS Home on one of the Best Islands the Keys has to offer. This home comes with 3 beds 3 baths stunning views from the porch & balconies, with a pool, dock & completely landscaped… luxury homes

MLS 548666

COUNTY, FL 33042
$1,200,000
CUDJOE KEY, FL 33042
2222 Middle Torch

4 Beds 2 Baths Square Ft: 2220
Single Family Home - MLS#: 550769
Community: Misc Middle Torch Key - Mile Marker (MM) 28.0

Lost treasure of the keys on Middle Torch. Secluded and private with peaceful water views over the bird sanctuary and the waters of Big Torch Key.Over 2 acres with new 4 bedroom 2 bath home.Water side… luxury homes

MLS 550769

COUNTY, FL 33042
$1,199,000
CUDJOE KEY, FL 33042
1086 Flagship

2 Beds 2 Baths Square Ft: 1156
Single Family Home - MLS#: 550863
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

Enjoy the fabulous Keys lifestyle in this adorable home located on Flagship DR, Summerland Key. Direct ocean front location makes for superior boating.24K boat lift, step down seawall, fish cleaning station… luxury homes

MLS 550863

COUNTY, FL 33042
$1,198,000
CUDJOE KEY, FL 33042
20942 W 6th

3 Beds 3 Baths Square Ft: 2772
Single Family Home - MLS#: 547039
Community: Cudjoe Gardens - Mile Marker (MM) 21.0

Custom CBS 2772 SF Jewel in Cudjoe Gardens!Elegant & Spacious w Southern Exposure on the Screened Lanai/Canal gives you winter warmth.Split floor plan features a Delightful open liv Rm/Kitchen area with… luxury homes

MLS 547039

COUNTY, FL 33042
$1,195,000
CUDJOE KEY, FL 33042
359 La Fitte

4 Beds 3 Baths Square Ft: 3057
Single Family Home - MLS#: 548631
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

Want it All? Custom built concrete 3 story contemporary home, has all the features of a retreat with all the comforts of home. 4 bedrooms with custom travertine baths allows privacy and comfort for your… luxury homes

MLS 548631

COUNTY, FL 33042
$1,179,000
CUDJOE KEY, FL 33042
737 La Fitte

4 Beds 3 Baths Square Ft: 1983
Single Family Home - MLS#: 548683
Community: Jolly Roger Estates - Mile Marker (MM) 28.5

Location, Location, Jolly Rogers Estate OPEN WATER!! Beautiful open water & sunrise views from this 4 bedroom 3 bath home. New Kitchen with granite counter tops, Viking stainless steel appliances. New… luxury homes

MLS 548683

COUNTY, FL 33042
$1,165,000
CUDJOE KEY, FL 33042
1005 Flagship

3 Beds 3 Baths Square Ft: 2750
Single Family Home - MLS#: 550229
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

SPACIOUS SUMMERLAND COVE ISLES HOME is a true Keys paradise! The 10,080 sf lot offers lush, tropical landscaping, a wonderful pool area, fenced back yard & 80 ft. concrete dock with boat lift & davits.… luxury homes

MLS 550229

COUNTY, FL 33042
$1,150,000
CUDJOE KEY, FL 33042
1146 Lagoon

3 Beds 2 Baths Square Ft: 1845
Single Family Home - MLS#: 549651
Community: Summerland Cove Isle - Mile Marker (MM) 25.5

Beautiful water views. Two story concrete block home an a point lot. Excellent boating with plenty of dockage & boat lift. Cool off in the in ground swimming pool. Big breezy porch takes in the water… luxury homes

MLS 549651



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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 (Realty World Freewheeler) are marked with the MLS Log and detailed information about them included the name of the listing brokers office.

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