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:

30353  Heron Lane  For Sale, MLS 584017
$560,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,156 SqFt Days Listed: 362
-34.12% ($290,000) 8 Price Changes : Last Change 90 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 75ft.

Storm damaged CBS canal home on three lots totaling 23,000 square feet-room for all your toys. Many upgrades including impact resistant windows and doors, granite counter-tops and stainless steel appliances. Located at the end of the canal, home has a concrete dock with davits, swim ladder and fish cleaning station. Large walk-in closet in the master bedroom. Large open deck has peekaboo views of the open water.

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 11 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.

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 16 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!

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 36 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

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 10 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

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 254 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

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 95 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.

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 167 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....

72100  Overseas Highway  For Sale, MLS 583865
$12,500,000
Craig Key
Craig Cay Island   - MM: 72.00
6 Bed, 6 Baths, 9,737 SqFt Days Listed: 369
+19.05% ($2,000,000) 1 Price Change : Last Change 306 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin106ft.

Craig Cay Island Estate - Construction has commenced! A unique opportunity for a buyer to participate in this exciting project, affording a buyer an option to choose their interior finishes, based on their personal preferences, within a specified budget. When completed, this magnificent, ground-level & sprawling, 9,737 sq. ft. home will be an exceptional masterpiece, with 6 bedrooms, 6 full baths, 2 half baths, exercise room, full entertainment room (above the dining room), glass solarium, tackle room, 3 car garage, captains quarters (above the garage) overlooking the 300 of deep-water, protected boat basin with 106 of concrete dock and a custom, a summer kitchen with the appearance of being set inside the 222 long pool which will wrap around both sides of the house, facing the bay.

1740  Overseas Highway 4 For Sale, MLS 584692
$12,750,000
Marathon
Palm Island   - MM: 48.00
7 Bed, 7 Baths, 6,432 SqFt Days Listed: 324
-17.74% ($2,750,000) 1 Price Change : Last Change 75 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip

Private bayfront island situated in the heart of the Florida Keys. Nestled behind gates and lush tropical landscaping are a magnificent main house and two private guest houses, a swimming pool, and deep water protected dockage for multiple boats. The island-style two-story main home offers two inviting bedrooms, a spacious living and dining area, a showcase kitchen, and French doors that open to lovely first and second floor porches overlooking the bay. The impressive guest quarters provide comfort and privacy with four bedrooms, four bathrooms, and a private patio with bay views. An additional one-bedroom guest cottage offers open bay views and a sandy beach area. The swimming pool with sundeck is surrounded by swaying palm trees and tropical gardens

34  Key Haven Road  For Sale, MLS 586843
$659,000
Key Haven
Key Haven 1st Add   - MM: 5.00
4 Bed, 4 Baths, 1,758 SqFt Days Listed: 174
-17.52% ($140,000) 3 Price Changes : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

This canal home on a large 6000 square foot lot offers plenty of room for entertaining indoors, on lanai, or by the sunny canal. Spacious and light filled home offers open living and dining areas. The kitchen has stainless appliances, granite countertops, and overlooks canal. Split bedroom floor plan with spacious guest room off kitchen with private entrance. Master bedroom offers sliding glass doors to lanai, en suite bath, and walk-in closet and there are two additional bedrooms, & an updated hall bath. Central AC, terrazzo floors, tile floors, accordion shutters, seawall & more!

112  Bruce Court  For Sale, MLS 585558
$949,000
Marathon
Sea Air Estates   - MM: 52.00
5 Bed, 5 Baths, 2,719 SqFt Days Listed: 264
-17.41% ($200,000) 7 Price Changes : Last Change 19 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift75ft.Cut/Na

Pool, Boat lift, Seawall, Garage, Stilted, Concrete construction, what other boxes can this check? Located Bayside in Marathon, 75 feet of seawall, quick out to Bay, Upstairs is 3bed 2bath, downstairs is 2 bed, 1bath and is above flood, Elevation cert available, has sink and fridge and access to back yard, each level has their own screened in porch overlooking the pool, property is already a licensed vacation rental, do not walk property or disturb tenants, Call for appointment

3236  Catherine Road  For Sale, MLS 584841
$1,649,000
Big Torch Key
Dorns Subdivision   - MM: 28.00
3 Bed, 3 Baths, 2,700 SqFt Days Listed: 313
-15.39% ($300,000) 3 Price Changes : Last Change 128 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip240ft.

Here it is! Natures Best Private Estate in the Lower Florida Keys. Offering the greatest world class fishing, diving and snorkeling, Unobstructed big and small boating for both power and sail access. This solid CBS home has a 2 slip dock with control depth of 4.5 of crystal clear water. Annually brings in legal, transient short term (zoned SR-L) rental income between $100K to $125K. With a protected sandy beach steps away, its strong rental history and many repeat guests, this 1800 sq ft, 3 bedrooms, 3 full baths is a one of a kind property that will never be replicated again in the Keys and is a must see! Niles Channel with its 40 bridge clearance is one of the best water ways and deep channels in the Keys for big boat accessibility and gin clear turquoise water. Owners request a 48 h

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: 115
-15.38% ($200,000) 1 Price Change : Last Change 101 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

181 N Airport Road  For Sale, MLS 584370
$995,000
Plantation Key
Tavernaero   - MM: 91.00
3 Bed, 3 Baths, 2,816 SqFt Days Listed: 342
-15.32% ($180,000) 1 Price Change : Last Change 97 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip,

This classic treasure offers a special retreat which encompasses two oversized lots bordering private airstrip along Tavernier Creek, & offering a home with covered hangar, private in-ground pool, storage shed & boat dockage. This all concrete home includes 3 bdrms & 3 baths with one guest suite located above flood on ground floor, & large master suite & guest suite upstairs, updated kitchen with open concept dining & living room connected to large glassed in porch, office/laundry, central AC, all accessible via an interior staircase. Large screened in pool and oversized backyard allows for many possibilities to create your own paradise. This residence is in impeccable condition & ready for your personal touches. ADJACENT 3RD LOT AVAILABLE FOR SALE WITH HOME ($1,295,000)

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 201 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!

118  Madeira Court  For Sale, MLS 588155
$1,999,000
Lower Matecumbe
Port Antigua   - MM: 74.50
5 Bed, 5 Baths, 4,201 SqFt Days Listed: 79
-13.09% ($301,000) 6 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

MOTIVATED SELLER WANTS OFFERS! Enjoy the ultimate in modern luxury at this architecturally striking brand new home in Port Antigua. This custom built home was designed with meticulous attention to every detail. Enter the home and look through the expansive sliding glass doors out to the salt system pool and 60 ft. concrete dock. Other custom features include a 3 stop elevator, Italian porcelain tile throughout, quartz countertops and gourmet kitchen with Thermador refrigerator, freezer and wine columns with auto door opening and a large center island with waterfall edge and storage on both sides. After a fun day on the water relax in the pool or spa or cook up the days catch in your well appointed kitchen.

435  121ST St Gulf   For Sale, MLS 584382
$1,000,000
Marathon
Hawaiian Village   - MM: 53.50
3 Bed, 3 Baths, 1,731 SqFt Days Listed: 341
+12.99% ($115,000) 2 Price Changes : Last Change 74 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Rip Rap

Located directly on Vaca Cut, across from Aquarium Encounters, Instant access to both Ocean and Gulf, Centrally located, weekly rentals allowed, If your looking for a fixer upper on the open water this is it, Put your own touches on this massive house. Over 1700 sf of living space upstairs, and an additional 625 of downstairs space buyer to verify, but currently hosts 1 bed, and 1bath with tons of storage space, Elevator goes all the way up to roof where you could add railing and additional space for open water views of both ocean and gulf, Rip Rap shoreline featuring 110 feet of frontage, room for pool and tiki, Make this your dream home on the open water at an affordable price, House is stilted and above flood.

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 46 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.

26  Osprey Road  For Sale, MLS 588556
$575,000
Key Largo
Sexton Cove   - MM: 106.00
3 Bed, 3 Baths, 1,100 SqFt Days Listed: 52
-11.40% ($74,000) 1 Price Change : Last Change 50 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

TOO MUCH TO SAY ABOUT THIS BRAND NEW WATERFRONT HOME! EVERYTHING IN THIS HOME SAYS QUALITY! FROM ITS METAL ROOF TO THE TOTALLY WATERPROOF PLASTIC DISTRESSED WOOD FLOORING AND IMPACT WINDOWS AND SLIDERS THROUGHOUT. THERE IS NOTHING LEFT TO CHANCE IN THIS BEAUTIFUL KEY LARGO HOME. IN ADDITION THIS HOME FEATURES AND OPEN FLOOR PLAN WITH A TOP OF THE LINE KITCHEN. ENJOY YOUR KEY LARGO WATER VIEW FROM THE SECOND STORY BALCONY THAT RUNS THE ENTIRE LENGTH OF THE FRONT OF THE HOME. ISLAND LIVING AT ITS BEST!!

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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