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Cudjoe Key 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 Cudjoe Key homes for sale below are on the gulf side / bay side.

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Total Listings 5
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$450,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
2 Bed, 2 Baths, 980 SqFt Days Listed: 56
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This sale is for three 5000 square foot lots. Two are undeveloped (bilders points TBD) One lot has an abandoned house so it is ROGO exempt.

$699,000
Cudjoe Key
Cudjoe Acres   - MM: 21.50
2 Bed, 2 Baths, 855 SqFt Days Listed: 25
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Island life awaits! Beautiful, elevated home boasts 2 spacious bedrooms and 2 recently renovated baths. Fenced yard with ample parking. Just off famous US1 this property is sited on a spacious lot with plenty of versatility! Zoning is Suburban Commercial (SC) which may allow for a Special Vacation Rental Permit. Perfect property for an owner occupier or investor. Wraparound porch offers sunrise and sunset views with a deck off kitchen/primary suite and another deck off living room along with two sets of stairs with access to yard and parking. Bonus non-confirming space is ideal for a home office or commercial use. Property offers ample off-street parking for your RV, autos, and boat. The large lot is fenced and private with room for a pool or perfect as is with the tropical landscape and low maintenance ground covering. Owner occupied and well maintained, this property is move in ready. Hurricane shutters, metal roof, secluded private lot, & custom outdoor shower make this a perfect Keys oasis. Building up or adding a rooftop deck would give you amazing water views. Property has a tankless water heater and sheds for extra storage. Great location in the Florida Keys with nearby community boat ramp, dining and beaches. Bahia Honda State Park just 17 miles and Key West 19 miles.

$1,175,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
3 Bed, 3 Baths, 1,260 SqFt Days Listed: 83
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 820ft.

Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with your very own private beach and 298 sq. ft. of enclosed storage space. Schedule your private showing today! One of the Sellers is a Licensed FL Real Estate Sales Associate.

$1,196,000
Cudjoe Key
Cudjoe Ocean Shores   - MM: 23.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 143
-6.93% ($89,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits85ft.Concrete

If you are looking for the Island Life with the best boating access in the Keys, this is the property for you. This beautifully updated tropical Keys home on a lushly landscaped spacious 10,200 square foot lot, is located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable for its premier boating access to world class fishing and diving in both the Atlantic and the Gulf via Kemp Channel. Kemp is one of the deeper easier channels to navigate to the Gulf, and has a much higher bridge clearance to get under US 1 for quick and easy access to the Atlantic. This combined with having 85 of canal frontage on an extra wide canal with lots of room to maneuver, makes this property perfect for bigger boats. With two ensuite bedrooms and a split floor plan, this home offers extra privacy for family and guests. The large covered screened back deck spans the length of the house overlooking the canal and is the perfect setting for dining al fresco. There is a garage and large enclosure below, and plenty of room in the fenced yard to store your toys. Start and end your day on the rooftop deck, sipping coffee soaking in morning sunrises over Kemp Channel and savoring appetizers and cocktails as you enjoy the unique and spectacular Keys sunsets. This property has impact windows and a metal roof for your added protection and reduced insurance premiums. A 22 KW whole house propane powered generator keeps you comfy whenever we have a power outage. Located only a short 20 minute drive to Key West.

$1,785,000
Cudjoe Key
Cudjoe Ocean Shores Sec 2, 2b   - MM: 23.00
3 Bed, 3 Baths, 1,667 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp8

The Island Life awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to the generous spacing between homes, as well as having the best boating access to BOTH the Atlantic and Gulf via Kemp Channel. Kemp is one of the deeper easier channels to navigate to the Gulf and has a much higher bridge clearance to get under US 1 for quick access to the Atlantic. This combined with having 85 of canal frontage on an extra wide canal with lots of room to maneuver, makes this property perfect for bigger boats. The luxurious tongue and groove western red cedar lined ceilings carry through to the exterior porch and soffit area. High end red Burch cabinets, granite counters, and Italian travertine flooring compliment the cathedral ceilings perfectly. The pocket style sliders allow you to open the entire living area up to the covered porch to create an even grander feel. The gourmet kitchen offers a Sub Zero 156 bottle wine cooler with 2 temperature zones in addition to top of the line appliances such as Bosch, and kitchen Aid. The split floor plan is ideal for added privacy. All bedrooms have 9 ceilings and cedar lined closets w/custom shelving while the baths feature granite counters on solid maple vanities with Alinea True Color Cosmetic light fixtures. Throughout this home youll find gorgeous custom tile and marble work top shelf hardware and fixtures. The landscaping is maintained by a cistern drip irrigation system fed from the gutters, all plumbed underground. This home also has a 36 KW whole house generator, a 1,200 lb. cargo elevator lift, a 17,000 lb. boat lift, and a circular paver driveway. No expense was spared!! Across from GVT owned conservation land. Custom cedar soffit install almost complete.

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 05-29-2025.
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