Florida Keys Waterfront Homes on the Bay / Gulf Side For Sale

Most of the properties in the Florida Keys peninsula are either on the bay / gulf side or on the ocean side of the island. The following Waterfront Florida Keys homes for sale below are on the gulf side / bay side.

Total Listings 268
Order By:

144  Bayview Drive  For Sale, MLS 573791
$3,395,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 1104
-12.93% ($504,000) 18 Price Changes : Last Change 47 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin113ft.

Beyond compare, this Polynesian inspired exquisite keys waterway Harum Designed custom home is 99% complete, pool is in, landscaping is underway. This spectacular home is not to be missed if you are looking for a yachtsmans location w/over 110ft of deep water dockage w/unlimited beam on deep water Hurricane Creek. Cathedral ceilings grace this masterpiece and its 3 bedroom and 3.5 baths is complimented by custom LED lighting, drop down TV. Incredible storage, 2 garages, generous and spacious covered gathering areas. The residence boasts an extraordinary creekside covered balconies overlooking Hurricane Creek with views of the Florida Bay making this a Florida Keys Treasure. The finished work detail is to much to list. Contact agent for full details and showing appointment.

110  Bayview Isle Drive  For Sale, MLS 574354
$2,850,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,240 SqFt Days Listed: 1071
-22.97% ($850,000) 4 Price Changes : Last Change 96 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift140ft.

ANCHORS AWEIGH - 140 of deep-water, protected, concrete/paved dockage is enjoyed at this serenely secluded property with sunset views. It is rare to find 2 adjoining lots in Venetian Shores with beautiful bay views, and convenient, direct access to Snake Creek. Remodeled in 2005 & designed to take advantage of magnificent views from every level. Downstairs rec room also used as 5th bedroom.

97340-360  Overseas Highway  For Sale, MLS 574489
$6,500,000
Key Largo
Mandalay Key Amt Plat   - MM: 98.00
20 Bed, 20 Baths, 20,084 SqFt Days Listed: 1063
-26.97% ($2,400,000) 4 Price Changes : Last Change 37 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

This stunning property is an entertainers dream that speaks of grace and uniqueness from the moment you step foot on the property. Beyond the brick paver driveway and tennis court, are two homes which are separated by a garden walkway. EACH home features 10 bedrooms and 11.5 baths! Both core living areas include grand staircases rising to the upper level master suites. Soaring ceilings with

303  Ann Bonny Drive  For Sale, MLS 578413
$1,194,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,869 SqFt Days Listed: 732
-14.71% ($205,900) 3 Price Changes : Last Change 202 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits200ft.

What an incredible location with endless views of the bay and deep water dock! This is a corner lot with water on 2 sides, 200 Ft +/- of concrete protected dockage, a boat slip, T dock and jet ski davit . Solid concrete construction including the roof. Expansive glass on the waterside of the house maximizes the incredible views. Large open concept entertainment area and tiled floors throughout. Expansive master suite encompasses the second floor and includes a master sitting area, bedroom with bay views, exterior concrete roof deck, and en suite bath. There is a concrete storage building, outdoor shower, accordion shutters, private boat ramp and a beautiful electric privacy gate. This is a wonderful island retreat, only 1 hour to MIA and yet a tropical world away!

81  Cannon Royal Drive  For Sale, MLS 578510
$4,950,000
Shark Key
Shark Key   - MM: 11.00
7 Bed, 7 Baths, 6,800 SqFt Days Listed: 725
-23.26% ($1,500,000) 2 Price Changes : Last Change 255 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Sophisticated & understated Shark Key home spread over 3 open water lots, on 1.5 acres, is built in timeless style & beauty. Plantation style, one level design is elegantly minimal yet luxurious with a living area featuring vast frontages that make the most of the views of the water. An extensive restoration was just completed with a brand-new kitchen & all new bath rooms. Lime stone floors, mahogany doors through-out, reclaimed cypress and oiled bronze hardware are a few of the elegant materials used & all built 11 ft over grade. 6800 SF w/ beautifully scaled rooms, 12 ft ceilings, custom 8ft doors & an abundance of indoor & outdoor dining areas. This home makes the ideal setting for an unforgettable experience, offering a combination of privacy & relaxation. Walk the Key stone accented

82994  Overseas Highway 23 For Sale, MLS 579971
$2,499,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 636
-28.60% ($1,001,000) 5 Price Changes : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Dock P

A classic Islamorada retreat. This private home is located in the exclusive bayfront gated community of Pen Key Club in the heart of Islamorada. The lovely one-story home offers three bedrooms and three bathrooms with panoramic views of the open water from every angle. Enjoy magnificent sunsets while relaxing in the living room or charming sitting areas on the open bay. In addition, the Pen Key Club offers a pool and boat dockage in a protected boat basin. This offering is Florida Keys living at its finest!

81906  Overseas Highway  5 For Sale, MLS 580100
$1,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 629
+4.55% ($50,000) 1 Price Change : Last Change 237 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

189  Indian Mound Trail  For Sale, MLS 580281
$3,775,000
Plantation Key
Indian Waterways   - MM: 89.00
4 Bed, 4 Baths, 2,343 SqFt Days Listed: 616
-5.51% ($220,000) 1 Price Change : Last Change 328 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip

SANCTUARY BEACH HOUSE- This unique Islamorada residence is supremely located on the Florida Bay with year-round sunset views. Tranquil, natural beauty embraces the beautiful azure waters which create a breathtaking backdrop for this beach-style home. One and a half lots on the bay feature a lush tropical vegetation, great lawn, large pool and spa, sandy beach, protected deep-water boat basin with boat ramp, Jacuzzi deck and rock pond with bridge. Once you enter through one of the two electric gated entrances, you are immediately struck by the privacy and tranquility, hence the name Sanctuary. This residence affords stunning, vast panoramas of the Florida Bay. Open and enclosed patios and porches offer abundant opportunities to relax in the sun or the shade.

701  8Th Street  For Sale, MLS 580294
$3,520,000
Key Colony
Key Colony Beach 1st Addn Amd   - MM: 53.50
9 Bed, 9 Baths, 7,642 SqFt Days Listed: 615
-24.30% ($1,130,000) 18 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift230ft.Concr

Exquisite waterfront gated estate. Beautiful custom built homes. Main house has 5 beds, 4 baths, upper and lower living rooms, covered porches, heated pool/Spa , garage with workshop with direct access to dock area. Custom touches throughout.Attached Guest/Staff house has 2 bed, 1 bath with separate entrance . Main and guest house being offered fully furnished.Additional custom build(Ryder built) guest house has 2 beds, 3 baths, anglers room which could be converted into additional bedrooms, covered porches on canal side, garage with access to dock area. Partially furnished. There is 230 Ft of deep water dockage with fast access to either ocean or gulf. 2 boat lifts, electric service to docking area, 50 Amp/30 Amp, 220/110 and a dedicated Spotless water system for rinsing bo

22  Hilton Haven Road  For Sale, MLS 580606
$4,400,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 5,898 SqFt Days Listed: 592
-19.93% ($1,095,000) 2 Price Changes : Last Change 168 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift105ft.Concr

Wondrous waterfront estate only a few minutes from downtown Key West. Capturing the relaxed grandeur of a bygone era, this sprawling home features water views from almost every room in the house. Facing South with views from East to West, the main house was restored in 1995 with walls rebuilt in concrete to include Pella windows & Anderson glass pocket doors to complete the indoor/outdoor living dream. When entering the home through the huge hand made art pieces that comprise the front door you immediately see through to the fantastic central courtyard with pool and entertainment areas along with the open water beyond....

1  Evergreen Avenue  For Sale, MLS 580731
$1,229,900
Key Haven
Key Haven 10th Add   - MM: 5.00
4 Bed, 4 Baths, 3,110 SqFt Days Listed: 584
-9.50% ($129,100) 5 Price Changes : Last Change 3 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Spacious Key Haven canal home with 4 bedrooms, 3 Full baths. 1st floor open floor plan, kitchen w/ built in appliances, formal dining & living room areas, sliders open to covered porch overlooking canal with gulf or ocean access in minutes. New 1st floor furnishings incl. 2nd floor master suite has private porch w/ partial Gulf View, his & hers walkin closets, bath w/dual sinks, jacuzzi tub & walkin shower, 2nd floor laundry. Jack & Jill bedrooms have private hall w/bath. Floating jet dock for your boat incl. New concrete dock for 2nd boat tie up. 3-plus car parking in rear of home, mature Mango tree in side fenced yard, ample storage under home w/ solar screening. Solar water heating, window treatments inc. Virtual tour attached, Owner is licensed Florida Broker

161  Palo De Oro Drive  For Sale, MLS 581489
$3,150,000
Plantation Key
Venetian Shores   - MM: 86.00
8 Bed, 8 Baths, 6,308 SqFt Days Listed: 531
-30.00% ($1,350,000) 4 Price Changes : Last Change 12 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.Concrete

Enjoy astounding views upon entering this estate home with soaring ceilings and floor-to-ceiling windows. The home is set on nearly a half-acre lot and offers eight bedrooms and six-and-a-half bathrooms. Views of Snake Creek and the ocean beyond can be seen from screened-in balconies on all three levels. A beautiful screened-in pool and spa, 100 feet of protected dockage and mature tropical landscaping with lighting complement the outdoor oasis. The home is complete with a double four-car garage, separate guest quarters, an elevator, and a gated driveway.

35  Sea Lore Lane  For Sale, MLS 581980
$2,250,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 3,408 SqFt Days Listed: 494
-8.16% ($200,000) 1 Price Change : Last Change 75 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Nestled among the palms at the end of picturesque Sea Lore Lane, this grand elevated home rests on nearly half an acre of waterfront splendor. Luxurious and secluded with dramatic open water views on 3 sides, this beautifully renovated home has soaring vaulted ceilings and magnificent natural light. Interior features include 4 spacious bedrooms, all with en-suite bathrooms, large kitchen, separate laundry room, and bonus sleeping loft. Covered parking and plenty of storage under the house, huge backyard with lush grass, beautifully maintained landscaping, a tiki hut, and ipe hardwood dock. A private path leads to the communitys swimming lagoon and sandy beach, and its just a short stroll to the tennis courts and clubhouse. Experience luxury waterfront living at its finest...

57733  Morton Street  For Sale, MLS 582147
$2,550,000
Marathon
Grassy Key   - MM: 58.00
9 Bed, 9 Baths, 7,006 SqFt Days Listed: 481
-3.77% ($100,000) 5 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Davits

Gulf front estate located on exclusive Morton Street in Grassy Key, this 2.82 Acre property offers six individual living units plus a large storage garage. The main house has expansive open water Gulf views with three bedrooms, three bathrooms, soaring ceilings and granite kitchen. Private boat basin and salt water pond. Additional homes include a 2/1 separate living unit below main house, 2 bed/2 bath CBS cottage and separate 1/1CBS cottage with metal roofs. A 1600 sq ft apartment over the storage garage and a 1 bed, 1 bath efficiency

83  Lake Shore Drive  For Sale, MLS 582251
$1,599,000
Key Largo
Key Largo Park   - MM: 101.00
6 Bed, 6 Baths, 3,238 SqFt Days Listed: 473
-5.89% ($100,000) 3 Price Changes : Last Change 90 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Sunsets galore and from every floor. One of a kind bay-front estate with lots of privacy, sandy beach, great dockage and 2 of everything (2 master suites, 2 living areas and more). This open water home built in 2002 boasts 6 bedrooms and 2 separate living areas with room for 2 families and more. The property can be used in its entirety or be used as a vacation rental; the possibilities are endless. Its great location puts it close to Miami for an easy commute. Investors beware.

52  Cannon Royal Drive  For Sale, MLS 582320
$3,250,000
Shark Key
Shark Key   - MM: 11.00
4 Bed, 4 Baths, 3,339 SqFt Days Listed: 468
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Panoramic Sunsets! Open Water Island Style Home offers privacy & relaxed living all-on-one-floor, located in the exclusive gated community of Shark Key. Upon entering the front door you are met with gorgeous views of the turquoise waters of the Gulf of Mexico.
The open floor plan encompasses four bedrooms three and one-half bathrooms and office. The gourmet kitchen will inspire your inner chef with its granite counters, center island with seating, Sub Zero, Bosch, DCS Fisher & Paykel stainless steel appliances. The expansive living room with soaring vaulted tongue and groove ceiling and a wall of glass opens to create the ultimate indoor/outdoor experience. Enjoy stunning panoramic sunset views on your covered rear porch and entertainment area.

139  Gimpy Gulch Drive  For Sale, MLS 582483
$8,900,000
Plantation Key
Misc Plantation Key   - MM: 85.00
6 Bed, 6 Baths, 6,573 SqFt Days Listed: 457
-6.27% ($595,000) 1 Price Change : Last Change 85 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

Opulent, alluring and meticulously detailed, this Islamorada Estate is where perfection meets the Bay ~ welcome to The Fish Ranch. Located on Plantation Key, The Fish Ranch estate features two (2) single family residences plus a media house, and cabana with outdoor kitchen. World-class designs make this one of the more distinguished estates for the most discriminating buyer. Elevator shaft, 100 swimming pool with two beach entries, hot tub, 250 of sandy beach, putting green, dockage, architectural designed landscaping with fire pit and lighting throughout. Also included with this property is an additional 19,729sf lot.

31 N Bounty Lane  For Sale, MLS 582758
$3,699,999
Key Largo
Buccaneer Point   - MM: 98.00
4 Bed, 4 Baths, 5,038 SqFt Days Listed: 442
-10.84% ($450,001) 2 Price Changes : Last Change 191 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Upon walking through the artist-designed custom copper front door its obvious that the finishes and features of this property were done to a gold standard. The timeless and classic travertine marble floors throughout give the homes modern architecture a luxurious feel. The breathtaking views center on the coveted Florida Bay, and sweep 180 degrees to Key West. Setting a new benchmark for luxury in bayfront real estate, 31 North Bounty Lane showcases meticulous craftsmanship. The Neff-designed kitchen, while sophisticated and functional, is equipped with high-end Thermador appliances including an induction glass cooktop, double refrigerator, wine chiller, and double oven. Other features include a glass tile backsplash, exquisite green pebble granite, and a walk-in pantry.

30326  Flamingo Lane  For Sale, MLS 583388
$595,000
Big Pine Key
Tropical Bay   - MM: 30.50
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 400
-11.19% ($75,000) 3 Price Changes : Last Change 162 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 75ft.

Canal front 3 Bedroom 2 Bath Home on 7,500 sq ft lot + 7,938 corner canal lot, concrete block home, plenty of downstairs storage 524 sq ft. screened patio, plenty of room for a pool minutes to getting to open water

33  Key Haven Road  For Sale, MLS 583446
$1,824,000
Key Haven
Key Haven 10th Add   - MM: 5.00
4 Bed, 4 Baths, 2,400 SqFt Days Listed: 394
-6.41% ($125,000) 3 Price Changes : Last Change 14 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Basin,

NEW waterfront estate with boat slip within one mile of Key West. Impressive 4BR 3 Bath luxury home with privacy gates on enormous lot of over 27,000 Sq Ft includes a designated boat slip in the private Key Haven Estates Marina for deep water boating access. High ceilings throughout, extensive covered porches, heated pool and spa, pantry, laundry room, chefs kitchen with Bosch appliances, wine fridge and Cambria Quartz. Low to no maintenance Hardie siding and Azek outdoor deck/railings. Beautiful landscaping, stone decking, pavers & fencing. Propane runs 5 burner gas stove, tankless water heater and pool heater. Smart outdoor camera security in place. Cat 5 rated, new construction. Optional 2 car garage. Future backyard observation deck over the water in the permitting process.

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 01-26-2020.

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92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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