Sugarloaf Key Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Waterfront homes in Sugarloaf Key are some of the best in the market.  These highly sought after Florida Keys properties are quite popular, making up the majority of the Sugarloaf Key real estate market.  This area in the Lower Florida Keys is known for its organic beauty, with a stunning, peaceful atmosphere.  Oceanfront homes for sale in Sugarloaf Key and gulf or bayfront houses in Sugarloaf Key are numerous and are designed for real estate buyers looking to experience the best of the Florida Keys lifestyle.  Browse Florida Keys MLS listings below to see all waterfront properties in Sugarloaf Key.

Total Listings 28
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156  Sugarloaf Drive  For Sale, MLS 587672
$549,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 67
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Cut/Natural

Bay views 3 bedroom 2 bath canal front home in Beautiful Sugarloaf Shores, quiet location, great neighborhood, affordable insurances, newer well built modular home in good condition. All furniture and housewares are negotiable. Porch has south east exposure to enjoy the evenings and ocean breezes on porch. Luxurious step in full whirlpool bath in master suite. Metal roof and impact windows and doors. Room to expand home or build a deck with bay views, on the extra columns. Priced to sell quickly. Affordable Insurances flood is $399 2019.

1107  Hawksbill Lane  For Sale, MLS 587646
$739,000
Sugarloaf Key
Vacation Harbor   - MM: 19.50
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits68ft.Concrete

Meticulously maintained, elevated 3 bedroom 2 bath concrete block home. Open water views on a deep boating canal. Just 5 minutes by boat to the Atlantic or 7 minutes to the backcountry sand bars. This canal boasts a deep draft and 68 feet of dockage. Each bedroom faces open water views on the screened in porch. Numerous updates and upgrades inside and out of this pristine home. Kitchen has GE profile and Bosch appliances with gas stove and range. Countertops are solid quartz. Floors are carbonized bamboo throughout. Propane fueled on-demand hot water heater for independence from the power grid for cooking and bathing.The outdoor spaces are perfect to enjoy the open water views in your screened in porch or tiki hut lounge area while basking in the refreshing breeze.

17213 E Starfish Lane  For Sale, MLS 588268
$739,900
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 27
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Great location only a short drive to Key West this CBS home built in 2000 sits on a 15,978 sq ft lot surrounded by a concrete privacy wall with gated drive. This bank owned 3/2 is waiting for you to make it your own estate. Lower level boasts a 1408 sq ft garage with 3 large doors. upstairs has a large master suite, granite tops and a nice view of the bay from your living area and master suite.

16823 E Point Drive  For Sale, MLS 586387
$759,900
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,740 SqFt Days Listed: 165
-10.49% ($89,100) 4 Price Changes : Last Change 21 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

This waterfront home is located in the prestigious South Point neighborhood of Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 minutes outside of Key West. Sprawling over a 12,500 sq. ft. lot the 3 BR home boasts 1,740 sq. ft. & is highlighted by the bright & airy Great Room offering soaring ceilings & lots of glass looking out to the water. Plenty of room for entertaining on the colossal waterfront Porch or in the large Kitchen and Dining area. The Master Suite offers bamboo flooring & walk-in closet. Quick open water access from the dock w/lift and excellent kayaking & paddle boarding through the winding creeks that lead to the ocean. Never lose power with the whole house generator with auto switch. Metal roof, new pea-rock yard & tropical landscaping.

17337 East Dolphin Street  For Sale, MLS 586785
$775,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 2,018 SqFt Days Listed: 132
Single Family - Active - Waterfront Yes
Side of Island: Median - Dockage: n/a

OPEN HOUSE December 15, 1-3p. This mid-century modern house was the first Florida Keys home for the great Composer Jerry Herman. Inspired by Frank Lloyd Wright architecture, its structurally open-floor plan has entry to garden from every room. Master suite especially calls nature indoors thru walls of glass. Nature is magnificent here, akin to Old Floridas Suwanee River--100 of canal-front just 50 yards from Sugarloaf Sound. The 2bed/2bath house is as lyrical as it is elegant: Bright, airy great room boasts Cuban-tile floors, Redwood-beam ceilings, central AC/heat, Bosch appliances, ground-level living. Theres a bonus room + laundry room off the kitchen. Architecturally fits into natural environment, but in its 57 years, the cinder-block house has never had structural hurricane damag

126  Shore Lane  For Sale, MLS 585985
$779,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,733 SqFt Days Listed: 193
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Davit Pads

This Mid-Century Modern Franklin Lloyd Wright inspired home boasts over 2,500 sq. ft. of indoor/outdoor living space. Wrapping around an 800 sq. ft. covered & screened lanai the 3/3 home offers picture perfect views down two canals & tropical gardens with water features from every room. The very open floor plan features tongue-in-groove ceilings, cuban tiled floors, & a retractable wall of glass allowing the outdoors in. The 11,250 sq. ft. lot enjoys approx 250 of waterfront on 2 canals with concrete dock, ramp & step-down for easy kayak & paddle board access. After a day out on the water unwind at the waterfront bar or enjoy a book in the gardens on your hammock. A garage/large work-shop offers storage for all your toys, tools and garden equipment. Walled for privacy.

17170  Amberjack Lane  For Sale, MLS 588636
$789,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 16ft.Rip Rap

Just like New! This beautifully renovated Contemporary Modern 2 bedroom 2 bathroom stilt home, sits on a 12,500 sq. Ft canal lot boasting 100 ft of waterfront, with desirable SW exposure, in a prime location on the only flow through crystal clear canal in highly sought after Sugarloaf Shores with excellent access to the Ocean and Back-country, is new down to its studs, including a new metal roof. As you enter you are greeted by gorgeous views of the water, new hurricane impact doors and windows, wood-style porcelain flooring and a spacious open plan chefs kitchen with a bar for entertaining friends and family, porcelain counter tops, new custom cabinetry and s/s appliances. The large bright great room and dining area lead out onto a spacious screened in porch.

17151  Marlin Drive  For Sale, MLS 588152
$825,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,522 SqFt Days Listed: 36
-2.83% ($24,000) 1 Price Change : Last Change 12 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

OPEN HOUSE 11/17 1-3PM.Welcome to the SUGAR SHACK, located in one of the coolest boating neighborhoods near Key West. Here, your pristine free flowing canal serves as yourmaintenance free swimming pool. This elevated two story custom home sits on a lush, spacious lot affording many options: a boat ramp, RV, plus all your toys. 3 bed/2 bath property features an open concept plan with vaulted ceilings and french doors opening to breezy decks on both levels, plus an expansive wooden dock. Enjoy stunning water views and spectacular sunsets over Sugarloaf Sound. New roof, new bamboo flooring, new electric panel. Ample storage in the garage plus multiple vehicle parking in the driveway. Comes fully furnished for immediate occupancy or rental. High definition LED TV , stereo

16680 E Point Drive  For Sale, MLS 587791
$829,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 1,801 SqFt Days Listed: 58
-1.19% ($10,000) 1 Price Change : Last Change 19 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: DavitsConcrete

Pristine and immaculate canal-front home in the desirable South Point neighborhood of Sugarloaf Shores. Two bedrooms and three baths with an open kitchen, dining, living-room concept. A wall of glass doors lead to the covered entertaining gazebo overlooking the canal and with views of the open water. Under the gazebo is more lounging and entertaining space along with a spa. Endless possibilities with this beautiful home situated on a 16,500 sq ft lot with a concrete seawall with davits. Room for a pool, tropical gardens or leave as is with easy landscaping maintenance. Come take a look at this gorgeous home in the coveted South Point area! Both of the Owners are Fl Licensed Real Estate Agents, but not the listing agent.

17049 W Bonefish Lane  For Sale, MLS 588129
$839,900
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,300 SqFt Days Listed: 37
-1.07% ($9,100) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits40ft.

Waterfront stunner is ready for its new owner today! This 3 bed, 2 bath home is turnkey and can be used as a rental property. The house has 1300 sq ft with impeccable ocean views from nearly every room in the house. The large living and dining floor plan opens up to the screened in back porch for entertaining. The great sized lot offers plenty of room for storage or your water toys. There is ample amount of room for parking and an extra space for an RV.Being sold fully furnished, all you have to do is move in your personal items and enjoy Florida Keys living at its finest!

17194  Coral Drive  For Sale, MLS 586488
$874,500
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,548 SqFt Days Listed: 153
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Spectacular canal-front, corner lot oasis! Come take a look at this wonderful canal-front, three bedroom, two bath home nestled in among a thoughtfully designed tropical sanctuary. Open, updated kitchen, living, dining plan with a gorgeous master suite and outdoor sitting area along with two more bedrooms and a bath. Theres also an additional space, now used as an office, but could easily be a formal dining area or sitting area with a large covered porch. Huge, 15,125 sq. ft lot with lots of room for additional living/entertaining space and room for a pool. Not to worry about storage, as this property even has a two car garage and additional workshop area. Easy access to the open water. Dont miss this one!

17218 E Dolphin Street  For Sale, MLS 587172
$1,099,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,844 SqFt Days Listed: 106
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Pretty long water views down the canal from this custom built 3 BR/3BA home on over a 1/3 of an acre in Sugarloaf Shores. As you enter into the 1,844 sq. ft. home the Sun Room/Foyer greets you leading to the Great Room which boasts hardwood floors & Dining Area that overlooks the water. The adjacent Kitchen features a large center island, tons of custom cabinetry & black stainless appliances. The 3 large Bedrooms are all ensuite including the colossal Master Bedroom with updated bath and access to the Porch w/walk-around deck. Really quick ocean access w/no bridges via Tarpon creek from your composite dock. Room for all of your toys in the oversized 4-car garage. Gardeners will love the fully fenced yard with a large orchid house and lots of lush tropical landscaping.

1261  Crane Boulevard  For Sale, MLS 587589
$1,100,000
Sugarloaf Key
Sugarloaf Acres   - MM: 19.50
4 Bed, 4 Baths, 2,440 SqFt Days Listed: 72
-15.38% ($200,000) 1 Price Change : Last Change 59 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

City slickers need not inquire: This is a nature-lovers hideaway edged by the Great White Heron National Wildlife Refuge. Tucked between a natural hardwood hammock (1.39 acres) and mangrove wetlands (.50 acres) that stretch to the Gulf of Mexico, the elevated 2-story house has 2 bedrooms/1.5 baths on the first level and 2 beds/2 baths on the second. All rooms have water views; most have access to balconies--in fact, more than 1500sf of porches, balconies and catwalks. Two-car garage enclosed with 1200sf of ground-level storage space & workshop w/AC. A grassy lawn amidst the 3 acres of private forest offers room for a pool!!! Property is hard to find. Call Realtor to meet you at the end of Crane Blvd. because, well, this is where you go to get away from it all

1023  Loggerhead Lane  For Sale, MLS 588457
$1,100,000
Sugarloaf Key
Vacation Harbor   - MM: 19.50
3 Bed, 3 Baths, 1,645 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 300ft.

Must see to experience all this one of a kind property has to offer! Secluded oasis on the Gulf of Mexico with 2+ acres, boat dock and breathtaking views. An entertainers backyard with a sunny pool and covered bar only add to the magic of this 3 bedroom, 2.5 bathroom home with loft and widows walk. Double lot with electric hook-up allows for RV on property. Pool and deck renovated in 2018. Exterior of house completely painted in 2018 as well. A short 20 minute drive to Key West, but a world away from the hustle and bustle... come overwhelm your senses in this Florida Keys dream house!

1163  Hawksbill Lane  For Sale, MLS 588668
$1,249,000
Sugarloaf Key
Vacation Harbor   - MM: 19.50
3 Bed, 3 Baths, 1,656 SqFt Days Listed: 2
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Fantastic views of the Gulf & Backcountry from every angle at this open water home on Upper Sugarloaf Key. 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, stainless 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. Lots of downstairs storage & plenty of room for pool and RV. Offered Turn-Key!

17260  Oleander Lane  For Sale, MLS 587256
$1,340,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,866 SqFt Days Listed: 97
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Mermaids Lair, a gorgeous 1/2 acre + waterfront property located in the exclusive neighborhood of Sugarloaf Shores. Arrive through electronic gates to the large CBS home which boasts a winding salt water lagoon that wraps around the property. The 3 BR 2 BA home has been superbly renovated with luxurious appointments & superb craftsmanship which will tantalize your senses. Enter in to the colossal Great Room which features soaring wood ceilings, porcelain wood plank flooring and an adjoining wrap-around screened Porch which extends the main Living Area by over 670 sq. ft. allowing picture-perfect sunrise to sunset water views. The designer Kitchen offers custom glass cabinetry, custom designed imported mosaics, stainless appliances, and gorgeous granite counters with center island

16845  Tamarind Road  For Sale, MLS 585303
$1,399,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 3,042 SqFt Days Listed: 238
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.

17179  Amberjack Lane  For Sale, MLS 587934
$1,450,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
5 Bed, 5 Baths, 3,081 SqFt Days Listed: 48
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

One of the best built canal-front homes in South Florida, this 4 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.

17346  Keystone Road  For Sale, MLS 586680
$1,499,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,116 SqFt Days Listed: 140
-9.15% ($151,000) 2 Price Changes : Last Change 38 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.

340 S Point Drive  For Sale, MLS 587080
$1,599,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,935 SqFt Days Listed: 113
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift100ft

Famous Keys sunsets over Sugarloaf Sound from this tastefully remodeled & impeccably maintained 3 BR 4 BA Pool home in the prestigious South Point neighborhood of Sugarloaf Shores. Enjoy picture perfect water views from all rooms including the Great Room highlighted by a retracting wall of glass allowing the outdoors in. The Chefs Kitchen features stainless appliances & large granite bar for entertaining. The Master Suite is complete w/a luxurious spa-style bath &. large private Porch. Relax by your waterfront pool offering lots of decking & a covered lanai. Perfect accommodations for your water toys w/ 100 of seawall w/boat lift & quick ocean access via Sammys Creek & a large basin to launch your kayaks & paddle boards to paddle the winding mangrove creeks just minutes away.

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 12-14-2019.

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