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

Total Listings 38
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16750  Old State Road 4A   For Sale, MLS 589844
$4,499,000
Sugarloaf Key
Sugarloaf Beach   - MM: 17.00
6 Bed, 6 Baths, 5,208 SqFt Days Listed: 43
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift,Boat

Arriving to your stunning 5,200 sq. ft. Oceanfront Estate you will be greeted by majestic gates opening to a professionally landscaped 2.5 acre property boasting an 8 Slip Boat Basin with 16,000 lb Lift and a designer Lagoon-Style Pool. Once here you will enjoy world-class fishing and diving within eyesight from your back yard. After a day on the water sip cocktails at the poolside Tiki or watch beautiful wildlife from the sand Beach. The colossal Great Room looks out to the ocean and features wood floors and an open Kitchen with stainless appliances plus a Dining Room that also boasts fantastic ocean views. More picture perfect views of the ocean, pool and gardens are seen from the grand Porch. Guest are accommodated in the private 3 BR Guest Suite

17024 W Green Turtle Lane  For Sale, MLS 590241
$4,250,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 3,014 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift,Boat

One of a Kind Open water & canal front estate located on a quiet street, just 12 miles east of Key West. Relax on the porches or pool patio, enjoy breath taking views & perfect sunsets over-looking uninhabited islands. Recent renovation compliments the original exposed timber & beam 12-20 ceilings. The elegant main house sits on open water & canal featuring two ensuite bedrooms, a half bath & loft area. Wet bars in the living room and loft for entertaining. The gourmet kitchen features quartz counter tops, custom cabinets, and Viking appliances for the finickiest chef. This property includes a detached guest house/office with incredible bay views, additional guest quarters, detached air conditioned two car garage with storage loft, stone walkways, AC workshop/game room..

1180  Sugarloaf Boulevard  For Sale, MLS 589870
$3,950,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 3,954 SqFt Days Listed: 41
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Boat Slip,

The Masterpiece Estate | Giving the entire residence a feeling of dynamic movement, this exquisitely designed custom masterpiece was built for privacy and with water views framed throughout the entire estate. Situated on coveted Sugarloaf Shores, enter the estate through a private gated entrance to find an architect designed 3,954SF residence perfectly sited on a lushly landscaped 1.35 acre lot with panoramic water views, a 40ft. heated lap pool, and your own private beach. Featuring a boat house for a watercraft up to 30ft, 750sf of concrete seawall, a private boat ramp, and World Class fishing and boating at your finger tips, this is truly a boaters dream.

15410  Old State Road 4A   For Sale, MLS 589992
$3,549,000
Sugarloaf Key
Sugarloaf Beach   - MM: 17.00
4 Bed, 4 Baths, 2,205 SqFt Days Listed: 34
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Excellent investment opportunity to own an oceanfront estate in the FL Keys with a transient license to rent nightly,allowing you the best opportunity to maximize income when you are not staying there!This is extremely rare in Monroe County,as most rentals are restricted to min 28 days. Nikhila Sunrise Beach is a stunning private oceanfront estate that sits on her very own secluded 310FT natural beach scattered with lots of swaying palm trees! Enjoy ultimate privacy in this newly remodeled elevated 4BR 3BA home boasting 2 master-suites,1 on the main floor & 2nd on the top floor,each with their own screened private balconies & walk in closets.The 3rd BR on the main floor is split from the master-suite allowing utmost privacy, w/access to a bathroom that also serves as guest powder room....

731  Sugarloaf Boulevard  For Sale, MLS 589472
$2,995,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 4,021 SqFt Days Listed: 62
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Stunning Architectural Masterpiece! This home of over 4000 square feet boasts a two story foyer that leads you up to the Great Room with Travertine marble tile floors from Italy. The custom chefs kitchen is detailed with Italian Cherry-wood cabinetry topped off with Giallo Reale marble counter-tops and European Stainless Steel appliances. While entertaining (and this is an entertainers/chefs home) you can close off the kitchen with the retractable wall. You & your guests will enjoy the views of beautiful Sugarloaf Sound. The Master Bedroom offers a veranda with Italian Travertine. To complete the Master Suite, the bath has Verona marble counters and Botticino marble flooring, a glass shower and a Bidet. All three guest rooms have their own private verandas. To top off this incredible

17387 E Allamanda Drive  For Sale, MLS 586584
$2,949,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
5 Bed, 5 Baths, 3,488 SqFt Days Listed: 255
-4.84% ($150,000) 2 Price Changes : Last Change 58 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads,Davits

Secluded on a 15,000 sq ft tropically gated lot in Sugarloaf Shores is an estate of understated elegance and Caribbean inspiration. The 3,500 sq ft residence takes full advantage of its waterfront location, blurring the lines between indoors and out and allowing for the most pleasurable resort-like lifestyle. The style lends itself to the Islands with its breezy outdoor spaces while the light-filled, view-focused interior has been adapted for relaxed, refined modern living. This newly renovated 5 bedroom 4 bathroom estate is graced by soaring tray ceilings, oversized porcelain tile throughout and the wall-to-wall impact windows are a haven for gazing at the beautiful exclusive waters of Sugarloaf Sound. The grand entryway with a sweeping staircase draws you into a voluminous layout

17138 W Dolphin Street  For Sale, MLS 590065
$2,750,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 4,055 SqFt Days Listed: 29
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp1

This completely custom open water home in Sugarloaf Shores boasts over 400 of waterfront where you can enjoy Keys famous sunsets over Sugarloaf Sound. Once here you will you will have so many choices including world-class fishing and diving just minutes away or relaxing kayaking and paddle boarding through winding creeks leading out to the ocean. Play by your resort-style pool complete with fountains and covered lanai. Friends and family can gather on the colossal porch overlooking the pool and water or in the spacious Great Room featuring marble floors and a gorgeous Kitchen offering a granite center cooking island and Wolf & Sub-Zero stainless appliances. Guest will be accommodated on their separate floor with 2 Bedrooms, Bathroom and large Family Room while

16623  Banyan Lane  For Sale, MLS 584722
$2,499,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
5 Bed, 5 Baths, 4,078 SqFt Days Listed: 385
-12.32% ($351,000) 1 Price Change : Last Change 359 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Davits

This 4,000 sq. ft. custom built concrete 5 BR 3.5 BA Pool home sprawls over 1/2 acre point lot & is highlighted by gorgeous sunset views over Sugarloaf Sound. As you enter through the Foyer to the large Great Room beautiful Brazilian hardwood floors & soaring ceilings greet you along w/lots of glass looking out to the open water. The Chefs Kitchen offers granite counters, lots of cabinetry & breakfast nook w/wide water views. The Master Suite is complete with large bath, his/her walk-in closets & picturesque views of the bay. The 2nd story Family Room is ideal for entertaining friends & family. Guests are accommodated in the Guest Wing w/2 large Suites. The tropically landscaped grounds boasts a sparkling waterfront pool & concrete dock w/davits. 5- car Garage & metal roof & storage.

15420  Old State Road 4A   For Sale, MLS 588452
$2,399,000
Sugarloaf Key
Sugarloaf Beach   - MM: 17.00
4 Bed, 4 Baths, 4,309 SqFt Days Listed: 121
-7.73% ($201,000) 2 Price Changes : Last Change 26 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Magnificent Oceanfront home offers serenity & privacy 120 ft of private beach,ZONED SR-L ZONED FOR VACATION RENTALS UNDER 28 DAYS enter foyer to the winding staircase to this 4300 sq ft 4 bedroom 3 1/2 bath home, enjoy open water views from everywhere you look, unwind at your custom built infinity pool over looking your beach plus pool side bar, 2 car garage + 1226 storage, all sliders are impact, 2 car garage

18957  Hansen Trail  For Sale, MLS 589684
$2,250,000
Sugarloaf Key
Sugarloaf Acres   - MM: 19.50
2 Bed, 2 Baths, 3,668 SqFt Days Listed: 50
Single Family - Active - Waterfront Yes
Side of Island: Median - Dockage: None

The Lanai Estate is an exquisite private & gated retreat in Upper Sugarloaf Key and also is a great investment opportunity as new homeowners may apply for Vacation Rental Use. Set upon a sprawling 3+ acre waterfront lot, this paradise escape is the perfect blend of serenity and nature. Private walking trails, wild Key Deer, exotic bird watching, unobstructed water and sunset views, World class kayaking and paddle boarding are all at your fingertips. Gorgeous grounds lead to the crown jewel, a Hawaiian style residence boasting elite amenities, including pristine tropical grounds, a private fruit and vegetable garden, Impact windows and doors throughout, entertainment & dining spaces, 2 artists studios both with 17 vaulted ceilings, over 3,000 square feet of covered porches...

16705  Tamarind Road  For Sale, MLS 588005
$1,890,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 3,086 SqFt Days Listed: 151
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Designed and built by owner in 2015 this stunning 3 Bedroom 2 Bath home sprawls over almost a half acre on sparkling open waters in the prestigious South Point neighborhood of Sugarloaf Shores. Boasting over 3,000 SF the modern home features soaring ceilings, marble and solid oak flooring, and lots of glass looking out to picture perfect water views. Entertain friends in the true Chefs Kitchen complete with Miele appliances, double wall ovens, Italian designer cabinetry and bar. Guests are accommodated on the main floor Suites while you retire in the 2nd floor Master Suite offering marble Bath with separate shower, large walk-in closet and private veranda with access to the roof top deck to enjoy the wide water views. The spacious Laundry Room could easily be converted to a 3rd Bath

17033 W Coral Drive  For Sale, MLS 588777
$1,799,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,580 SqFt Days Listed: 102
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Rip Rap

Welcome to this spectacular, exclusive and one of a kind custom Keys home. Located on the desirable Sugarloaf Key, this lovely unique home was designed by the current owner and has many architectural details. Open, light and airy with grand 10 ft high ceilings throughout including vaulted ceilings in living room and master bedroom. A custom keystone coral fireplace and wood beamed ceiling add to the ambiance of this lovely living space. Gaze out at amazing water views from 3 sides of this home, including spectacular views from private balcony off the 2nd floor master bedroom suite. With vaulted ceilings this massive ensuite bedroom is a paradise in itself. The marble master bath offers a jetted tub or custom shower with pebble flooring and German glass block. A large walk-in closet

17048  Flying Fish Lane  For Sale, MLS 586116
$1,499,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,504 SqFt Days Listed: 291
-11.77% ($200,000) 2 Price Changes : Last Change 70 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Gorgeous sunset views over Sugarloaf Sound from this Polynesian-inspired home. Drive through the gates an immerse yourself in this tropically landscaped 17,500 Sq Ft point lot paradise. This 3 bedroom 3 bathroom plus loft home offers expansive water views from all angles and is accented by an open floor plan, soaring wood beam ceilings, and spacious bedrooms. Walls of glass and a large wrap around screened porch surround the Great Room, making indoor/outdoor living a breeze! After a day on the water, dock your boat at the concrete dock, complete with boat cut-in, relax on the sandy waterfront beach or sip cocktails in the colossal covered screened lanai.

16845  Tamarind Road  For Sale, MLS 585303
$1,379,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 3,042 SqFt Days Listed: 345
-1.43% ($20,000) 1 Price Change : Last Change 35 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Exceptional 4 BR/3.5 BA open water pool home in Sugarloaf Shores, an upscale coastal community of waterfront homes just minutes to Key West. The custom home boasts gorgeous open water views and lots of upgraded finishes including beautiful Mahogany wood floors and a granite Chefs Kitchen offering stainless appliances and a center cooking island. The open floor looks out to water on all sides and leads to an expansive deck where you can enjoy dining under the stars. After a day out on the water lift your boat onto the davits at your concrete dock and relax by the waterfront pool & spa. The 2-story home is ideal for guests or large families with a Master Suite and entertaining area on the 1st floor an a 2nd Master & Guest Bedrooms on the 2nd main living level.

17346  Keystone Road  For Sale, MLS 586680
$1,350,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,116 SqFt Days Listed: 247
-18.18% ($300,000) 4 Price Changes : Last Change 40 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 40ft.

Brand New Showcase Home recently completed and ready for its lucky new owners! This one of a kind property is located 17 miles from Keys West on Sugarloaf Key - rated one of the top 20 Islands to live on in the world by Islands Magazine! The 3-bedroom 2 bath home has a relaxed, spacious feel with a tasteful combination of elegance and function throughout. Lots of space to entertain with expansive decks and incredible open water views. The outside living room with wine bar and fireplace will be your favorite place to enjoy waterfront living. Featuring a private dock and half acre lot. View the supplement for full details on this property.

17134 W Buttonwood Drive  For Sale, MLS 588996
$1,349,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,968 SqFt Days Listed: 85
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davits125f

Fabulous location just one in from the open water at this beautifully remodeled Pool home in Sugarloaf Shores. The tastefully decorated home boasts a large Great Room w/travertine floors, plantation shutters, built-in speakers & an open Kitchen featuring granite counters, center cooking island w/ gas stove & stainless appliances. The Master Suite offers a stylish travertine Bath & Porch access for enjoying Keys sunsets over the open water down the canal. The heated pool is adorned w/tropical palms & lots of decking including a covered lanai to relax on. Plenty of room for your center console & flats boat at the concrete dock complete w/20,000 lb lift, davits, fillet table, underwater lighting, power & water. Storm ready w/impact doors & windows and metal roof. Security system & more.

17179  Amberjack Lane  For Sale, MLS 587934
$1,298,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
5 Bed, 5 Baths, 3,081 SqFt Days Listed: 155
-10.48% ($152,000) 2 Price Changes : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

One of the best built canal-front homes in South Florida, this 5 Bedroom 4.5 Bath home is wonderfully unique. All bedrooms have en suite baths. A stunning great room features 17-foot ceilings, fireplace and French doors opening to a screened porch. Handcrafted wood cabinets, and the cypress wood theme create a comfortable and relaxing atmosphere. Outdoors, everyone loves swimming in a saltwater pool. Dock your boat in the back yard canal and fish off the dock. A spacious wraparound porch provides relaxing views of the canal, open water and pool. Other features include impact doors & windows throughout, hardiplank siding and storage galore. Fifth bedroom lockout with separate entrance is also possible. This Sugarloaf canal allows for convenient access to both the backcountry and ocean.

1561  Coral Court  For Sale, MLS 589767
$1,279,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 2,288 SqFt Days Listed: 47
-1.54% ($20,000) 1 Price Change : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Brand New Construction in desirable Sugarloaf Shores! This one-of-a-kind residence is nestled on a 15,847 SF tropically landscaped lot situated on a crystal clear, lagoon-style canal. A stunning dual composite and stainless staircase leads you up to the well appointed 2,288 SF home. Designed for comfort, style and entertainment, the open concept floor plan is an entertainers dream! The Chefs Kitchen offers gorgeous granite countertops, custom cabinetry, stainless steel appliances and large center island with waterfall edge. Guest will be accommodated in one of the 3 spacious guest bedrooms while you retire in the Master Suite featuring luxurious over-sized tile shower and large soaking tub. After a day on the water, dock your boat at the compost dock and relax at your coastal retreat.

1163  Hawksbill Lane  For Sale, MLS 588668
$1,239,000
Sugarloaf Key
Vacation Harbor   - MM: 19.50
3 Bed, 3 Baths, 1,656 SqFt Days Listed: 109
-0.80% ($10,000) 1 Price Change : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Sportsmans Paradise! Located on the open water at the entrance to the GREAT WHITE HERON NATIONAL WILDLIFE REFUGE. Fish, Scuba Snorkel, and Kayak all from your backyard. The 3 BR home sprawls over a double point lot offering protected canal dockage w/10K lb boat lift, kayak ramp & immediate Gulf & easy Ocean access. The Old Florida-style home offers 1,656 sq. ft. plus a large Porch boasting picture perfect open water views. Entertaining is a must in the true Chefs Kitchen w/ granite counters, SS appliances, gas stove & breakfast nook looking out to the water. The Master Suite is complete w/walk-in closet, spa Bath & endless water views. This home is storm ready w/ hurricane impact doors & windows, metal roof & whole house generator w/auto-switch & alarm system. ONE OF A KIND LOCATION!

16843 E Point Drive  For Sale, MLS 589757
$1,199,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,224 SqFt Days Listed: 47
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

This beautiful custom waterfront pool home is located on a 60 wide crystal clear canal in the South Point neighborhood of Sugarloaf Shores, an upscale community of impressive waterfront homes just minutes from Key West. Boasting over 2,200 sq. ft. the 3 BR home has been impeccably maintained and features an open floor plan with soaring ceilings, solid wood floors and an updated chefs Kitchen offering custom cabinetry and stainless appliances including gas stove. Quick ocean access through Sammys Creek from the dock with 10,000 lb lift. After a day on the water relax by the waterfront Pool surrounded by lush tropical landscaping. The large 2-car carport is enhanced with new garage doors for privacy. New metal roof and fenced.

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 03-30-2020.

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92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

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