Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living spac...

Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-w...

Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key. NIGHTLY RENTALS ALLOWED Enjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom...

Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and la...

*SWIMMING POOL BEING BUILT NOW! Construction process underway. * Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating...

Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lo...

Welcome to your oceanfront retreat on Cudjoe Key, where panoramic wide open ocean views, exceptional outdoor living, and easy boating access come together to create the q...

Wake up to breathtaking Florida Keys sunrises from this exceptional oceanside waterfront home in Cudjoe Key. Offering 1,596 square feet of living space on an 8,920-square...

Canal-front Paradise Awaits! Incredible view from your back deck! Unit 424 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two...

Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature...

TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven inc...

Take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the...

Welcome to one of Cudjoe Gardens' most desirable waterfront addresses Built in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3...

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water ...

Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and...

SELLER ACCEPTING BACK-UP OFFERS: Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal...

This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO poi...

Opportunity Knocks! Exceptional Value with Endless Potential - If you've been waiting for the right home at the right price, you have found it just in time for lobster ...

Seller is Motivated! Coastal Charm Meets Modern Comfort Welcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath s...

Welcome to island living at its best in the gated waterfront community of Venture Out on Cudjoe Key. Lot 399 is a desirable 35' x 69' corner RV lot offering ocean peeks, ...

********Nightly Licensed Transient Rental!!!******** This amazing, two bedroom / one bathroom, open water front views , nightly transient rental is ready for you to en...

Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing ...

Build your Florida Keys dream in Cudjoe Key just 3 lots from open water. Dock has already been approved and house plans are ready to submit to the county to begin the RO...

Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining fr...

Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect F...

Discover your personal sanctuary in the heart of Cudjoe Key, where authentic Florida Keys charm meets modern coastal luxury. This stunning 2-bedroom, 2-bathroom home has ...

Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, ...

Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance co...

Reduced over 100k for a quick sale. Boater's Paradise in Cudjoe Key under 1 million! Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal r...

Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This comple...

Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. Ne...

SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panorami...

Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with...

Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat...

Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible po...

Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter...

Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter...

Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter...

Price Reduced! Motivated Seller... Stop dreaming and start packing. Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playgrou...

Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable isla...

Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortabl...

Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pi...

Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home s...

Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a tr...

$21,000+ Gross Rental Revenue so far in 2026! Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gat...

MAJOR PRICE IMPROVEMENT -- AN EXCEPTIONAL VALUE FOR A BEAUTIFULLY UPDATED CUDJOE KEY CANAL-FRONT HOME! This updated 3-bedroom, 2-bath canal-front home on Cudjoe Key o...

BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage bel...

Owner says ''Bring All Offers'' Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed. Welcome to your perfect getaway or ...

Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or...

Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surroun...

Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental locat...

ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23 Bring your RV or build your Florida Keys dream home without the hassle of going throug...

Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of ...

Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for i...

Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled ...

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water ...

Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevat...

Prime Lower Keys Commercial Real Estate for sale. Excellent visibility and easy access from Overseas Hwy. Corner location at MM 21 and Blimp Rd. Total of 3 Parcels of...

Oceanfront Paradise Awaits! Unit 182 in Venture Out Experience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room ...

The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid ...

Canal-front Paradise Awaits! Incredible view from your back deck! Unit 453 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two...

This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the b...

Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom...

Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal ...

Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean. Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-ba...

Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath con...

Attention Investors and business owners! Unique opportunity to purchase commercial building in Cudjoe Key with two established business incomes as well as a residential ...

Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestl...

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 ...

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions) over 300 feet of water frontage, boat basin, 3 c...

RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities...

Commercial or Mixed Use Development, 8 contiguous parcels with a total of 1.56 Acres with 240 feet of US1 frontage. One parcel includes a 745sf retail/service structure. ...

Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an overs...

Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of mod...

Transient Rental Vacation Home. Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sou...