Sugarloaf Key LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Total Listings 34
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$5,999,000 - Other (Sugarloaf Key) , FL

  • Beds: 10 Baths: 11
    Type: Single Family Home - MM: 17
  • MLS ID 114426
    Sq Ft: 10,036
  • Community: Sugarloaf Shores Days on Market: 1452
  • Waterfront: Yes - Waterview: Canal Front,Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Slip,Davits Other

Breathtaking 4.5 acre oceanfront estate on Sugarloaf Key. Sand Castle, formerly the Jerry Herman estate, offers multiple homes on a park-like parcel w/water on 3 sides. The elegant 8,219sf main home sits on its own beach, has 6BD/7.5BA, ocean views from most every room, custom pickled cypress walls & accents throughout, family room w/fireplace, formal dining room, sunroom & an enormous game room w/wet bar. Other amenities include a home office, pool, lagoon w/fountain & waterfall & a garage. Meander over a charming bridge to the 2BD/2BA, 745sf guesthouse w/its own covered boat slip & roundabout driveway. The grounds also include a 2BD/2BA, 1,072sf fully equipped caretakers home. Truly a rare opportunity to enjoy your own private Sandcastle!

$5,900,000 - Other (Sugarloaf Key) , FL

  • Beds: 7 Baths: 6
    Type: - MM: 16
  • MLS ID 121103
    Sq Ft: 3,340
  • Community: Sugarloaf Shores Days on Market: 23
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Lift

Remarkable gated and totally private 3.7 acre estate on 350 feet of natural white sandy beach on Atlantic Ocean. Nothing between you and Cuba except 90 miles of pristine ocean and American Shoal Lighthouse. Main house is a beautifully updated 1800 sq. ft., 3 bedroom, 2 bath modern island home with 2 guest cottages. Magnificent 500 ft. dock with a 45,000 lb. boat lift with 4.5 feet of water. Spectacular custom rock pool with waterfall grotto, complete with pool bar. Transient Licenses allow for exclusive vacation rentals which make this a great investment. International Airport nearby.

$5,900,000 - Other (Sugarloaf Key) , FL

  • Beds: 7 Baths: 6
    Type: - MM: 16
  • MLS ID 121129
    Sq Ft: 3,340
  • Community: Sugarloaf Shores Days on Market: 19
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Lift

3 Transient Homes - Remarkable gated and totally private 3.7 acre estate on 350 feet of natural white sandy beach on Atlantic Ocean. Nothing between you and Cuba except 90 miles of pristine ocean and American Shoal Lighthouse. Main house is a beautifully updated 1800 sq. ft., 3 bedroom, 2 bath modern island home with 2 guest cottages. Magnificent 500 ft. dock with a 45,000 lb. boat lift with 4.5 feet of water. Spectacular custom rock pool with waterfall grotto, complete with pool bar. Transient Licenses allow for exclusive vacation rentals which make this a great investment. International Airport nearby.

$4,400,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 6 Baths: 4
    Type: Single Family Home - MM: 17
  • MLS ID 566465
    Sq Ft: 5,000
  • Community: Sugarloaf Shores Days on Market: 37
  • Waterfront: Yes - Waterview: Oceanfront
  • Side of Island: Ocean Dockage: Boat Lift,Boat Ramp Other

Spectacular oceanfront gated estate. Private Marina with 4 docks and lift, Grotto style walk-in pool, tiki, 7,200 sqft covered living space, 19 rooms, 6 bedrooms, 4.5 baths.

$3,957,000 - Other (Sugarloaf Key) , FL

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 17
  • MLS ID 119751
    Sq Ft: 4,039
  • Community: Sugarloaf Shores Days on Market: 304
  • Waterfront: Yes - Waterview: Bay Front,Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Davits Other

Breathtaking Open Water Estate Home. Elevated & Built to exceed all building codes. This smart house has a 45,000kw whole house generator, including 500 gallon propane in ground tank. 4 Bedrooms all with ensuite baths plus office. German cabinetry, Meile & subzero appliances, hand blown Marauno light fixtures, elevator, custom Mahogany entrance doors with Marvin doors throughout. No expense was spared with this Masterpiece! Almost 10,000 sq Ft under Roof. Enjoy sunset while relaxing in the 40x40 pool with spa, waterfall & Gazebo. Extensive covered outdoor living areas. 4 car garage. 200 concrete dock w/davits on canal side & addnl 250 Natural Rip Rap wrapping around to the Ocean. Only minutes to the best fishing and diving in the Keys

$1,877,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 4 Baths: 5
    Type: Single Family Home - MM: 19
  • MLS ID 563737
    Sq Ft: 2,222
  • Community: White Heron Estates Days on Market: 355
  • Waterfront: Yes - Waterview: Bay Front,Canal Front,Gulf Front,None,Open Water
  • Side of Island: Bay/Gulf Dockage: None

Large and Private Estate Located At The End Of A Private Rd. Consists of Main Ground Level House, Decks and Walk Ways, CBS Ground Level Cottage, Guest House with storage & Laundry Room, Pool & Bath House, Horse Stables and lots of Land With Natural Keys Landscape. 2 Canal Lots on Open Water w. Vested Rights Permits and Plot #5 & man made beach area. Sunset Views. See Document and Supplement Tab.

$1,675,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 5 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 562353
    Sq Ft: 3,208
  • Community: Sugarloaf Shores Days on Market: 495
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin,Davits

Mini Estate, private, OPEN WATER, boat basin, heated pool, dock & davits, fresh water pond. This large home has it all. Five bedrooms 3 baths. Three floors, main floor.. 2 bedrooms 1 bath, living room, dining & kitchen. Step down to Master suite with your own washer & dryer. Lower level 2 bedrooms 1 bath,TV area and laundry room. Enjoy this gem in the heart of Sugarloaf Key.

$1,600,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 565004
    Sq Ft: 3,014
  • Community: Sugarloaf Shores Days on Market: 198
  • Waterfront: Yes - Waterview: Bay Front,Canal Front,Open Water
  • Side of Island: Ocean Dockage: Basin,Boat Lift,Boat Slip,Davit Pads

Why fly 6,000 miles to the South Pacific when you can have it here in the Florida Keys? This Polynesian-style home is located on a prime open water point lot in Sugarloaf Shores, just minutes from Key West. Once here you will enjoy fabulous boating, kayaking, & paddle boarding through winding creeks abundant in wildlife and just a short distance to the ocean for the best fishing and diving the Key

$1,549,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 2 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 566530
    Sq Ft: 1,369
  • Community: Sugarloaf Shores Days on Market: 31
  • Waterfront: Yes - Waterview: Bay Front,Canal Front,Open Water
  • Side of Island: Ocean Dockage: Boat Ramp 122ft.

Dazzling sunrise to sunset open water views from this premier 20,100 sf south facing peninsula in Sugarloaf Shores. The remodeled 2BR 3BA home offers 1,369 sf w/soaring cedar ceilings & 270 degree open water views from all rooms. Wrap around decks are ideal for entertaining & waterfront dining. Walled & fenced for privacy. 383 of waterfront w/224 concrete dock & ramp w/122 on protected canal.

$1,490,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 565576
    Sq Ft: 2,230
  • Community: Sugarloaf Shores Days on Market: 130
  • Waterfront: Yes - Waterview: Bay Front,Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Davits 166ft. Concrete

Amazing Sunsets...Over 300 Feet of Open Water Frontage...Unique owner financing! This family friendly, move in ready home, is located in the safe, upscale neighborhood of Sugarloaf Shores. Sitting on nearly 3/4 of an acre this three bedroom, three bath house offers open water views from nearly every room. Protected boat dockage, room for RV parking and your own private boat launch make this house

$1,399,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 566275
    Sq Ft: 1,536
  • Community: Sugarloaf Shores Days on Market: 54
  • Waterfront: Yes - Waterview: Bay Front,Open Water
  • Side of Island: Ocean Dockage: Boat Lift

Gorgeous concrete open water pool home in prestigious South Point. This beautiful home features an open floor plan boasting picturesque open water views through sliding walls of glass from all living areas & Master suite. Resort-style 60 lagoon pool surrounded by majestic palms & lots of decking. Dock w/boat lift, elevator & lush designer landscaping. Excellent rental income too!

$1,299,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 5 Baths: 4
    Type: Single Family Home - MM: 17
  • MLS ID 566025
    Sq Ft: 2,772
  • Community: Sugarloaf Shores Days on Market: 83
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Davits 120ft. Concrete

Open Water Overlooking Lower Sugarloaf Sound- huge pristine 5 bedroom, 4 bath custom built stilt home with awesome sunrise views, 120 feet of concrete seawall on an extra large lot. Prestigious South Point area with quick Key West commute. Amenities include two master suites, ADT security system, hot tub, davits, new paint inside and out, two entrances, lovely landscaping, and tiles throughout.

$1,095,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 17
  • MLS ID 566100
    Sq Ft: 2,000
  • Community: Sugarloaf Shores Days on Market: 74
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage:

This stunning custom built home by owner/builder for himself offers 4 BRs, 4 BAs & boasts resort-style amenities incl: heated custom pool, sandy beach, tiki pavillion, dock & gorgeous open water views! Open kitchen w/bar & wine chiller, 2nd Story Master w/porch, 2 ensuite guest BRs & more!

$1,075,000 - Other (Sugarloaf Key) , FL

  • Beds: 6 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 120716
    Sq Ft: 3,000
  • Community: Misc Baypoint/sugarl Days on Market: 86
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: Davits Other

Looking for a big home with room for visitors and fun on the water?! Rock solid concrete block 6BR, 3Bth, 3000 sq ft home has tons of closets & storage, plus a commercial grade elevator. There is a wet bar and formal dining room. 12 pocket sliders open to enjoy the beautiful open water views & morning sun. Large kitchen has stainless appliances & plenty of cabinets. Beautiful bathroom renovations. Enjoy the 30 foot heated pool and spill out spa. Feed the fish in your backyard aquarium off your 100 foot seawall. Sugarloaf canals are the cleanest and largest in the Keys; 12 deep and 75 wide! Kayak to the Atlantic or Gulf, or launch your boat off the 10,000 lb davits. 3 carports, 932 sq ft storage enclosure on ground level, metal roof.

$990,000 - Other (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 20
  • MLS ID 117928
    Sq Ft: 111
  • Community: Orchid Park Subdivision Days on Market: 691
  • Waterfront: Yes - Waterview: Canal Front,Open Water
  • Side of Island: Ocean Dockage: None

Have you run out of land space? Looking for a large parcel to call home? Look no further. Unique property with appoximately eight acres total! Postcard-perfect open water views of Sugarloaf Sound from your 3 bedroom,2 bath stilt home.Canal frontage on two sides of the property. Turn-key condition,indoor laundry room and large storage area for all your treasures.

$899,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 564221
    Sq Ft: 1,855
  • Community: Sugarloaf Shores Days on Market: 299
  • Waterfront: Yes - Waterview: Canal Front,Salt Ponds
  • Side of Island: Ocean Dockage: Boat Lift 100ft. Concrete

Gorgeous views over the nature conservatory at this impeccable pre-firm home with 2/2 up & 1/1 down. Stunning home features granite kitchen w/Viking, Sub-Zero & Bosch appliances, Anderson impact doors & windows, 15K pound boat lift, whole house generator & 500 sq ft porch. Beautiful yard w/waterfront spa, 100 concrete step-down dock on a 70 wide canal, & lots of lush tropical landscaping.

$879,000 - Other (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 120572
    Sq Ft: 2,058
  • Community: Sugarloaf Shores Days on Market: 117
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: Other Dockage

Lovely quality CBS canal home with pool. A spacious 3BD/2.5BA home with a stunning foyer entrance in a cupola of sky lights. Stainless appliances, built in glazed cherry wood cabinets in kitchen, wet bar, Master Bedroom and baths. A great laundry room with cabinets, sink, storage. Enjoy the wonderful screened pool and patio area perfect for entertaining friends or fun with family and a very desirable 3 car garage. Youll love this home in prestigious Sugarloaf Shores! Dont miss it!

$849,000 - Other (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 0
  • MLS ID 119197
    Sq Ft: 2,300
  • Community: Sugarloaf Shores Days on Market: 408
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: Other

NO STAIRS! Beautifully appointed Keys home on double lot in exclusive Sugarloaf Shores. CBS ground level that has never flood in main home! Updated kitchen with SS appliances and granite counters, new windows, new baths, cedar walk in closets, and easy close shutters. Tax roll says 3 bedroom when there are 2 but room for at least 2 more. Beautiful working fireplace for some chilly nights. Huge landscaped yard for entertaining. Seawall. Quick access to the gulf or ocean. Salt water aquarium type pool in rear. A real keysy home. Can come furnished.

$799,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 565821
    Sq Ft: 1,622
  • Community: Sugarloaf Shores Days on Market: 105
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage:

Enjoy gorgeous sunrise views over Sugarloaf Sound from your custom built 3 BR 2 BA home in Sugarloaf Shores. Located on the east side of the island this home offers quick ocean access through Tarpon creek. The 2-story home offers over 1,600 SF & boasts picturesque open water views from all Living Areas, including the screened Porch, and the private 2nd Story Master Suite. Dock, storage, & more!

$799,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 5 Baths: 3
    Type: Single Family Home - MM: 20
  • MLS ID 566117
    Sq Ft: 2,512
  • Community: Maggie & Mary Days on Market: 72
  • Waterfront: No
  • Side of Island: Bay/Gulf Dockage: None

Spacious & Almost Brand New 5 Bedroom 2 Story Home Located on over 2 Acres of Privacy With Sunset Views. Beautiful wild life and quick commute to Key West. Features split floor plan, 2 private master suites, tile floors, custom kitchen, impact windows, metal roof. Room for a pool & or additions. Rogo Exempt Lot next acre over available for sale too. Located near elementary and middle school.

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The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 02-28-2015.