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

Total Listings 25
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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: 1326
  • 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!

$5,995,000 - Other (Sugarloaf Key) , FL

  • Beds: 7 Baths: 6
    Type: Single Family Home - MM: 17
  • MLS ID 118496
    Sq Ft: 3,340
  • Community: Sugarloaf Beach Days on Market: 426
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Lift

Looking for absolute privacy and pristine waterfront? This beautiful gated compound sits on 3.7 acres with 350 feet of natural white sandy beach on the Atlantic Ocean. Driving through a beautifully landscaped garden with palm trees, black bamboo and fruit trees youll arrive at the main house with 3 bedrooms/ 2 baths, high ceilings, porch and a private Tiki hut. From the living room you look out to the beach and a magnificent 500 ft Dock with a boat lift, ready for your fishing trip. Bring your guests and family along to use the 3 cottages with their own porches and Tiki huts. Cool down in a one of a kind rock pool with waterfall, hot tub, separate pond and a huge pool bar. This would also be a great investment allowing vacation rentals.

$5,995,000 - Other (Sugarloaf Key) , FL

  • Beds: 7 Baths: 6
    Type: Multi-units - MM: 17
  • MLS ID 118515
    Sq Ft: 3,340
  • Community: Sugarloaf Beach Days on Market: 423
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Boat Lift

Looking for absolute privacy and pristine waterfront? This beautiful gated compound sits on 3.7 acres with 350 feet of natural white sandy beach on the Atlantic Ocean. Driving through a beautifully landscaped garden with palm trees, black bamboo and fruit trees youll arrive at the main house with 3 bedrooms/ 2 baths, high ceilings, porch and a private Tiki hut. From the living room you look out to the beach and a magnificent 500 ft Dock with a boat lift, ready for your fishing trip. Bring your guests and family along to use the 3 cottages with their own porches and Tiki huts. Cool down in a one of a kind rock pool with waterfall, hot tub, separate pond and a huge pool bar. This would also be a great investment allowing vacation rentals.

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

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 20
  • MLS ID 116980
    Sq Ft: 4,948
  • Community: Sugarloaf Townsite Days on Market: 759
  • Waterfront: Yes - Waterview: Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Basin

Pirates Cove - An exquisite 9 acre open water Sugarloaf Estate with huge detached 2,803 SF pool house/fitness center with sauna & bath, a large 7 car garage, clay tennis courts, a Co2 pool & an enormous boat basin. Magnificent 4 bedroom, 4.2 bath main house boasts a dramatic carved Mahogany staircase, 15 ceilings & marble & cherry floors. Enjoy a gourmet kitchen, formal dining room, library, study, conservatory & graceful covered wrap-around porches. Deep water boat access from your private boat basin with 200 of dock. Own Your Own Private Resort!

$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: 178
  • 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: 229
  • 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.

$1,800,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 563429
    Sq Ft: 3,188
  • Community: Sugarloaf Shores Days on Market: 258
  • Waterfront: Yes - Waterview: Bay Front,Open Water
  • Side of Island: Ocean Dockage:

This custom designed 3,200 Sq. Ft. 3 Bedroom 3 Bath plus Den home boasts superior finishes and is highlighted by floor to ceiling windows overlooking a sparkling infinity pool spilling over into Sugarloaf Sound. Amenities include a colossal chefs kitchen with quartz counters, stainless appliances, and cherry cabinetry. The tasteful Master Suite is complete with his/her dressing areas and spa

$1,800,000 - 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: 72
  • 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

$1,675,000 - 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: 369
  • 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.

$1,350,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 565576
    Sq Ft: 1,934
  • Community: Sugarloaf Shores Days on Market: 4
  • 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

$1,199,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 4 Baths: 5
    Type: Single Family Home - MM: 19
  • MLS ID 563335
    Sq Ft: 2,222
  • Community: White Heron Estates Days on Market: 265
  • Waterfront: No
  • 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 With Decks and Walk Ways, CBS Ground Level Cottage, Guest House with storage & Laundry Room, Pool & Bath House, Horse Stables and Land With Natural Keys Landscape. 2 Canal Lots on Open Water w. Vested Rights Permits Also Available For Sale At An Additional Price. See Supplement For More Details.

$995,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 4 Baths: 4
    Type: Single Family Home - MM: 17
  • MLS ID 564447
    Sq Ft: 3,081
  • Community: Sugarloaf Shores Days on Market: 143
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: Other Dockage

Beautifully hand crafted & custom built, this large canal front home has room for everyone & their friends! 4BD/4 full BA & 2 half BA surround a central great room w/hand planed Cypress floors & walls that completely open up to views of the water. Cathedral ceilings, 2 fireplaces, & custom Cypress doors complete the homey feel of this unique property.

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

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 20
  • MLS ID 117928
    Sq Ft: 1,306
  • Community: Orchid Park Subdivision Days on Market: 565
  • Waterfront: Yes - Waterview: Canal Front,Open Water
  • Side of Island: Ocean Dockage: None

Land, Land and More Land..Eight Acres Total! Front Row Seats to Mother Naturess spectacular show! Postcard-perfect open water views of Sugarloaf Sound from your over-size balcony. Privacy lot boasts over 348,000 square feet with over 2.000 s.f of canal frontage on two sides. Three bedroom home with open living concept, light and breezy in turn-key condition,indoor laundry room and large storage area for all your treasures.

$925,000 - 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: 173
  • 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 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 2 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 563786
    Sq Ft: 1,428
  • Community: Sugarloaf Shores Days on Market: 224
  • Waterfront: Yes - Waterview: Bay Front,Gulf Front,Oceanfront,Open Water
  • Side of Island: Ocean Dockage: Davits

Direct Ocean-front home with Watercolor sunsets and panoramic views of Lower Sugarloaf Sound. Rock solid home with perfect layout to take advantage of the views and ocean breezes. Huge, lushly landscaped lot, complete with concrete boat dock and davits. A must see if youre in search of your own private piece of paradise

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

  • Beds: 4 Baths: 3
    Type: Single Family Home - MM: 17
  • MLS ID 119241
    Sq Ft: 3,024
  • Community: Sugarloaf Shores Days on Market: 274
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: Davits Other

Waterfront Pool Home 4 bedroom over in Sugarloaf Shores! Waterfront with full concrete dock, davits, private boat ramp, & quick open water access. 3,024 SF home with a pool, great for entertaining. Large lot room for your toys. Lots of storage & large yard for pets & children.

$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: 282
  • 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.

$799,900 - Other (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 118867
    Sq Ft: 2,116
  • Community: Sugarloaf Shores Days on Market: 339
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: Davit Pads,Davits

Your perfect private getaway or permanent home is located on a beautiful wide open swimming canal just minutes from ocean and back country. With a extra large lot, docks, and davits, it is has everything for the boater, fisherman or diver. On top of everything is a Chickee Hut next to a beautiful pool which is just outside-no walking down stairs. Home has 3 bedrooms, granite counter tops and stainless appliances. The quiet desirable neighborhood in Sugarloaf Shores is just minutes from the Key West.

$750,000 - Other (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 119770
    Sq Ft: 1,670
  • Community: Sugarloaf Shores Days on Market: 172
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Median Dockage: Boat Lift

Motivated Seller! Bring all offers! Rock solid 3/2 located on a clean & deep swimming/boating canal.Low maintenance is the charm of this home with features including a metal roof, tile floors, PGT Hurricane rated storm windows and a 16,000 lb capacity boat elevator all designed to make your life easier. Inside the home is a lovely chef friendly kitchen and a living/dining space with doors opening onto the deck which has a staircase leading down to the canal and large storage closet. 2 bedrooms and 1 bath are on the first floor,the second story is all master-suite with its own private porch and very large closet. The 12,500sf lot is fenced and gated with low maintenance landscaping. This property has much to offer. Put it on your list.

$725,000 - Sugarloaf (Sugarloaf Key) , FL

  • Beds: 3 Baths: 2
    Type: Single Family Home - MM: 17
  • MLS ID 565446
    Sq Ft: 1,588
  • Community: Sugarloaf Shores Days on Market: 19
  • Waterfront: Yes - Waterview: Canal Front
  • Side of Island: Ocean Dockage: 411ft.

Beautiful canal front home in Sugarloaf Shores, lot 19,650sq ft,concrete circular driveway, downstairs patio, split floor plan 3 bedrooms 2 baths, tile flooring, upstairs patio, pristine condition.

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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 10-25-2014.