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 24
Order By:

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: 10
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Cut/Natural

Newer 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.

16961  Driftwood   For Sale, MLS 585998
$619,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,650 SqFt Days Listed: 135
PreConstructi - Active - Waterfront Yes
Side of Island: Median - Dockage: None

Pre Construction home with building permits currently submitted. Plans call for a 3 bedroom 2 bathroom modular home. Buyer can still choose finishes at this point in the building process. Current owner is continuing with development and the price is determined to change. House is scheduled to be installed Oct/ Nov 2019.

73  Venetian Way  For Sale, MLS 585979
$649,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,429 SqFt Days Listed: 136
-5.24% ($35,900) 2 Price Changes : Last Change 77 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads,DavitsCon

Enjoy Keys Living in this Sugarloaf Shores property. Perfect for boating and outside enjoyment! Swim in the clean clear canal and relax by the water! Plenty of room for all of your toys and trailers. Three outside sheds and a tiki at the waters edge. Covered entertainment area under the house. House features open floor plan with a combination of bamboo and tile flooring. Nice sized master suite with full bath, walk-in closet, and nice deck! Second bedroom has a full bath and deck too! Third bedroom is a loft overlooking the great room! Open kitchen, dining area, and living room with lots of windows and doors to let the light in. New metal roof in 2017. Extensive use of pavers for driveway and yard make for low maintenance. See this property and you will not be disappointed

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: 11
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  Starfish Lane  For Sale, MLS 584776
$750,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 218
-11.66% ($99,000) 6 Price Changes : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Price Reduced 17K and seller now offering a 20K credit to buyer at closing for closing costs. This property qualifies for a Jumbo Conventional Reno loan. Ask agent for details! Great Sugarloaf Shores location...this 3/2 CBS home with concrete privacy wall can easily be transformed into your own estate. Granite tops and tile floors, Large 3 door garage with room for 8 or more vehicles. Great bones on this bank owned property.

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: 75
Single Family - Active - Waterfront Yes
Side of Island: Median - Dockage: n/a

But of course the great Composer Jerry Hermans first Florida Keys home would be Mid-century Modern inspired by Frank Lloyd Wright: Structurally open-floor plan has entry to garden from every room. Master suite especially beckons nature indoors thru walls of glass. Nature is magnificent here, reminiscent of 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 grey 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 damage.

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: 136
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.

16823 E Point Drive  For Sale, MLS 586387
$799,900
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,740 SqFt Days Listed: 108
-5.78% ($49,100) 3 Price Changes : Last Change 13 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.

16680 E Point Drive  For Sale, MLS 587791
$839,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 1,801 SqFt Days Listed: 1
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 home in the coveted South Point area! Both of the Owners are Fl Licensed Real Estate Agents, but not the listing agent.

480 S Point Drive  For Sale, MLS 586712
$849,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,116 SqFt Days Listed: 81
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Pretty sunset views down the canal from this spacious 3 Bedroom Pool home in the South Point section of Sugarloaf Shores. Enjoy sunbathing by the heated pool or sip cocktails under the pool-side Tiki. Fabulous fishing & diving just minutes away from your composite dock w/davits. The open floor plan boasts 2,116 sq. ft. & is highlighted by walls of glass looking out to the pool & water. The chefs Kitchen is complete w/upgraded stainless appliances & granite counters w/breakfast bar. Lots of privacy for guests with 2 Master Suites on opposite sides of the home plus a 3rd Loft-style Bedroom with picturesque views down the canal. The easy to maintain property features hurricane impact doors & windows, metal roof, and a 15,125 sq. ft. peacock yard with tropical landscaping.

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: 96
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: 49
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: 15
-15.38% ($200,000) 1 Price Change : Last Change 1 Day 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 Florida Keys 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 level. All rooms have water views; most rooms have access to balconies for bird watching--in fact, more than 1500sf of porches, balconies and catwalks. Two-car garage enclosed with 1200sf of ground-level storage space. 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.

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: 40
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: 181
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
$1,549,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,116 SqFt Days Listed: 83
-6.12% ($101,000) 1 Price Change : Last Change 32 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: 56
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.

17048  Flying Fish Lane  For Sale, MLS 586116
$1,599,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,504 SqFt Days Listed: 127
-5.89% ($100,000) 1 Price Change : Last Change 61 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 2 bedroom 2 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.

17387  Dolphin Street  For Sale, MLS 585399
$2,200,000
Sugarloaf Key
Sugarloaf Shores   - MM: 25.00
3 Bed, 3 Baths, 2,419 SqFt Days Listed: 175
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

This property includes a spacious floor plan and 10 foot wide covered porches on both levels! Luxurious kitchen-granite counters, wood cabinets, stainless steel appliances with plenty of counter space. This property also includes an outdoor kitchen, swimming pool and beautiful landscaping. Master suite on the top level with the private entry to a covered porch that provides incredible views of the ocean.Buyer can also purchase MLS 581812.Listing agent is part owner.

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: 221
-12.32% ($351,000) 1 Price Change : Last Change 195 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.

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 10-18-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
Contact Us