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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17346  Jamaica Lane  For Sale, MLS 586529
$513,000
Sugarloaf Key
Orchid Park Subdivision   - MM: 17.00
3 Bed, 3 Baths, 1,092 SqFt Days Listed: 32
-5.00% ($27,000) 1 Price Change : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Waterfront Sugarloaf Shores 3 bedroom 2 bath home on stilts with porch overlooking the canal and storage downstairs. Inside you have an open floor plan with plenty of room.

17179 W Bonefish Lane  For Sale, MLS 585128
$599,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
2 Bed, 2 Baths, 1,248 SqFt Days Listed: 132
-10.46% ($70,000) 2 Price Changes : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

This 2 Bedroom 3 Bath PLUS BONUS ROOM Sugarloaf Shores home is located on a crystal clear 80 wide canal offering a concrete dock with davits and quick open water access to the ocean and back country. A tropically landscaped driveway leads you to your spacious home boasting wood plank vinyl flooring throughout and a newly renovated chefs Kitchen complete with center island, quartz counters, new cabinetry and stainless appliances. Retire in one of the 2 Master Suites on opposite sides of the main level or in the very private loft-style Bonus Room on the 2nd level. The colossal screened porch overlooks the water and is the perfect place for entertaining. There is plenty of room for all of your toys in the 1,232 sq. ft. storage area complete with garage and convenience bath.

16961  Driftwood   For Sale, MLS 585998
$619,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,650 SqFt Days Listed: 73
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: 74
-5.24% ($35,900) 2 Price Changes : Last Change 15 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

     For Sale, MLS 583354
$675,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,636 SqFt Days Listed: 240
-2.88% ($20,000) 2 Price Changes : Last Change 107 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Davits

REDUCED! DONT MISS SHOWING YOUR BUYERS THIS HOME. NEW METAL ROOF, Home has split A/C system & master side of home has a new central system just installed, new washer. Spacious, over 1600 sq. feet, split floor plan 3 bedroom, 2 bath elevated cedar home. 100 feet on a beautiful crystal clear canal, boat ramp, dock, davits with access to Ocean & Bay. Open living, cathedral ceilings & enclosed Florida room/porch. Tropical landscaping. Downstairs has a large storage garage. Located in prestigious Sugarloaf Shores, walking/bike paths lined with beautiful palm trees close to Key West. Nice Quiet Street! No road noise!

105 S Point Drive  For Sale, MLS 586576
$699,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,424 SqFt Days Listed: 30
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

Located in prestigious South Point in Sugarloaf Shores sits this custom build 3 bedroom 2 bathroom 1424 square foot house. Large bedrooms, open spacious living room, upgraded kitchen with granite counter tops, open water views of the sunset, high ceilings with a bathroom that can be accessed by the exterior are a few of the interior features. The downstairs consists of a 2 car garage, covered entertainment area and a bar that seats 10. Full concrete seawall, boat davits, large fenced yard with storage shed, a fully screened back porch, and a new metal roof are some of the many features. This home is wonderful for entertaining and has great ocean side boating with a wide canal that makes it easy for turning and navigating a boat.

17213  Starfish Lane  For Sale, MLS 584776
$767,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 156
-9.66% ($82,000) 5 Price Changes : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

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 being sold as is.

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: 13
Single Family - Active - Waterfront Yes
Side of Island: Median - Dockage: n/a

OPEN HOUSE Sunday, August 18, 1-3p. But of course the great Composer Jerry Hermans first Florida Keys home would be Mid-century Modern inspired by Frank Lloyd Wright: low-lying structure has open-floor plan w/entry to garden from every room. Master suite especially beckons nature indoors thru walls of glass. And nature is magnificent here, reminiscent of old Suwanee River--100 of canal-front just 50 yards from Sugarloaf Sound. The 2bed/2bath house is as lyrical as is elegant: Bright, airy great room boasts grey Cuban-tile floors, Redwood-beam ceilings, central AC/heat, Bosch appliances, single story. 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: 74
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.

17131  Marlin Drive  For Sale, MLS 585808
$849,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,236 SqFt Days Listed: 87
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Fabulous sunset and water views abound from this airy home. Tucked away in Sugarloaf Shores, enjoy views from inside and out. A large and private landscaped lot opens onto canal with dock with lift. Plenty of storage in legal downstairs.Great water access and minutes from Key West.

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: 19
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.

16823 E Point Drive  For Sale, MLS 586387
$849,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,740 SqFt Days Listed: 46
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.

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: 34
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!

16763 E Point Drive  For Sale, MLS 585923
$1,175,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
4 Bed, 4 Baths, 1,800 SqFt Days Listed: 78
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

This unique canal-front home offers remarkable charm and character, with upgrades and great features thanks to David L. Smith Interiors. This 1800- square-foot home offers 4 bedrooms 2 baths with a split floor plan. Well equipped kitchen with top of the line appliance plus a Perlick wine cooler a wonderful gathering place. Amazing large screened porch to relax after a long day on the water. This CBS homes also offers a concrete walk around deck. New 24g standing seam metal roof. Large garage area with automatic garage door opener, along with an extra storage area. Over sized lot 100 x 125, tropical vegetation, sandy beach area and a 100 foot concrete dock. This home is offered furnished!!!

17218 E Dolphin Street  For Sale, MLS 583748
$1,195,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,844 SqFt Days Listed: 214
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Rare opportunity to acquire a quarter of an acre private stellar custom home located in the quiet pristine Sugarloaf Shores neighborhood. Gated and secure for privacy, this 2 story CBS property features a sunny Florida room entry with hardwood floors, upgraded kitchen with stainless steel appliances, incredible 3 bedrooms with en suite bathrooms, accommodates up to 4 cars, room for a game area, formal dining room overlooking premium water views, detached enclosed Orchid house, large entertainers yard with mature landscaping, with canal front. A boaters dream! The possibilities and potentials are endless. This one-of-a-kind property, in a world-class location.

17203  Snapper Lane  For Sale, MLS 586937
$1,249,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 1,784 SqFt Days Listed: 9
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Perfection. As you enter into this perfectly remodeled 3 Bedroom plus Den/3 Bath home in Sugarloaf Shores you will notice the beautiful craftsmanship found throughout the home including shiplap walls, hurricane impact doors and windows, wood-style flooring and a gorgeous chefs Kitchen boasting quartz counters, custom cabinetry and stainless appliances. Enjoy al fresco dining on the covered pool-side lanai or on the spacious screened porch that overlooks the water. The Master Suite is the perfect place to end the day complete with quartz double sink vanity, soaking tub and separate frameless shower. Plenty or room for family and guests with 2 Guest Bedrooms and Baths plus a sleeping loft that is used as a Den. After a day on the water tuck your boat in to the protected lagoon & cool

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: 119
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
$1,650,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,116 SqFt Days Listed: 21
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.

17048  Flying Fish Lane  For Sale, MLS 586116
$1,699,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 2,504 SqFt Days Listed: 65
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.

16705  Tamarind Road  For Sale, MLS 582342
$1,874,000
Sugarloaf Key
Sugarloaf Shores   - MM: 17.00
3 Bed, 3 Baths, 3,086 SqFt Days Listed: 305
-14.82% ($326,000) 3 Price Changes : Last Change 93 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat L

Just reduced for quick sale! A must see. This home is immaculate and beautifully designed, offering unlimited water views in all directions for spectacular sunrises and sets. Better than new with over 3,000 square feet of living area w/elevator and can be purchased furnished. Why build or renovate when you can begin living the dream today? 3/3 with third bath converted to laundry area. Fully enclosed 2,000 Sqft Garage w/parking for up to 5 cars. Dock with 10,000 Lbs lift. Impact glass windows and doors and Barrel Tile metal roof. Interior features include soaring ceilings, 36x36 marble flooring, solid oak floors, Italian designer cabinetry, granite countertops and much much more. A must see!

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 08-17-2019.

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

1(800) 692-3605
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