The Lower Keys stretch from Big Pine Key down through Sugarloaf, covering some of the most unspoiled waterfront in the Florida Keys. Canalfront homes with easy Atlantic and Gulf access, open water estates with panoramic sunset views, and more affordable options than you'll find in the Upper Keys — the Lower Keys attract buyers who want the full Keys lifestyle without the crowds.
Big Pine Key is the commercial hub of the area and home to the National Key Deer Refuge. Little Torch, Ramrod, Summerland, Cudjoe, and Sugarloaf each have their own character — from tight-knit boating communities to larger lots with room to breathe. Browse by island below or use the search above to filter by price, beds, and property type.
Featured Listing
417 Pirates Road, Little Torch Key (Jolly Roger Estates) — courtesy of Maggie Beall, LoKation Real Estate
Full photos, details, and current price are at the link below.
View 417 Pirates Road listing details
Curious what's selling in a specific neighborhood? Create a free custom market report to see active listings, pending sales, and recent closings in any Lower Keys community. The data pulls directly from the Florida Keys MLS and updates every 5 minutes.
Contact Jim Signor to get help narrowing your search or to talk through what's moving in a specific island or price range.
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Beautifully renovated and designed for the Florida Keys lifestyle, this waterfront home is located in the highly desirable Ramrod Shores neighborhood. The home has been e...
This updated concrete cottage with all the necessities you will need to enjoy waterfront living in the Keys. This home has a metal roof, mini split A/c, updated kitchen a...
Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3-bathroom oceanfront estate offering breathtaking open water views, deep-water d...
OWNER FINANCING. 27452 ANGUILA LANE RAMROD KEY FOR RENT. REPAINTED INSIDE AND OUT. ALL NEW FLOORING. 1400 SQFT 180 MPH RATED 3/2 HOME. 300SQFT ENCLOSURE FOR ALL YOUR FISH...
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 an exceptional waterfront property on Summerland Key, where three contiguous canal-front lots create an expansive Florida Keys retreat. Situated on a combined ...
Waterfront Duplex with Income Potential in Big Pine Key! Live the Florida Keys lifestyle while your investment works for you. Welcome to 31032 & 31034 Hollerich Drive, a ...
Experience the PINNACLE of luxury waterfront living at this exceptional oceanfront residence on prestigious Flagship Drive. Completely reimagined with uncompromising atte...
Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb...
Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. S...
Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Key...
Only 40 homes on Exclusive No Name Key, ( Not Big Pine*) Newer143' concrete seawall with newer 30'Neptune boat lift with walk around, you have your own private boat ramp....
Escape to the Lower Keys with this peaceful Big Torch Key retreat overlooking protected lands. Enjoy convenient boating access to both the Gulf and Atlantic via Niles Cha...
Discover the ideal blend of comfort, space, and waterfront living in this beautifully maintained canal-front home on Ramrod Key. Offering 2,392 sq. ft. of living space wi...
Imagine having the freedom to create your own secluded retreat in the heart of the Lower Florida Keys. This remarkable offering includes two adjacent 2.5-acre parcels, co...
Move-in ready and beautifully updated! This charming 2-bedroom, 2-bath home offers approximately 960 square feet of comfortable living space in the desirable Summerland K...
Located at the end of a quiet street in Sugarloaf Key, this 2 bedroom, 2 bath canal-front home is only two lots in from open water and offers open water views from the li...
If you've been searching for an affordable stilted home in the Lower Keys that doesn't feel dated or compromised, this is one of the best values on the market. Built in 2...
Where open water sunrise views and world-class boating meet, you'll find this elevated waterfront retreat at 31485 Avenue G in Big Pine Key. Offering 3 bedrooms, 2 bathro...
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...
Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect ble...
Welcome to your own slice of the Florida Keys paradise. This beautifully remodeled and fully furnished 2-bedroom, 2-bath waterfront home is the definition of move-in read...
Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern desig...
LOOKING FOR A KEYS HOME WITH SOLID CONSTRUCTION? Check out this updated 3BD/2BA CBS home in desirable Pine Channel Estates, Big Pine Key -- just 30 miles from Key West an...
This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75...
*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...
Remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for...
A Classic Keys Boating Cottage! Exceptional value for a 3 bedroom 2 bath waterfront home in the Lower Keys! With 60' of seawall, enjoy easy boating access to nearby hot s...
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...
The Angler's Retreat -- Big Pine Key Resort-style canal front living beneath a majestic Banyan. Some places don't just change your pace -- they change your life. Tu...
Are you looking for a canal-front home that could use your TLC? Situated on a 9,375 sq. ft. fenced lot, this 2-bedroom, 3-bath CBS opportunity is about mid-way between th...
Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living space in a small, well-kept community in Summerland Key. This home is in excellent...
Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled op...
Welcome to your piece of paradise in beautiful Big Pine Key! This elevated, stilted home features 3 bedrooms and 2 bathrooms and is centrally located, making a perfect op...
3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island over...
Oceanside canal-front home in the desirable Breezeswept Beach Estates neighborhood of Ramrod Key. This 3-bedroom, 2-bath residence features a private pool and is ideally ...
Waterfront coastal retreat in a quiet neighborhood, just 3 houses from open water! This beautifully renovated 3-bedroom, 2-bath stilt home offers coastal comfort with mod...
Welcome to 629 Powell Drive in Little Torch Key, the lowest-priced fully stilted CBS home currently available in the Lower Florida Keys. This elevated 2-bedroom, 1-bath c...
Welcome to this beautifully updated 3-bedroom, 2.5-bath waterfront home situated on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Thoughtfully renovated ...
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...
Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is of...
TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven inc...
DOUBLE the Lot. DOUBLE the Waterfront. Endless Possibilities. Positioned on a rare spacious double lot near the Summerland Key airport, this waterfront property is tai...
If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989...
OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With can...
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...
Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with ...
Built in 2019 on a 7,412 sq ft Lot! This modern home features three (3) bedrooms and two (2) bathrooms, offering everything you need. It's low maintenance yet packed with...
Welcome to this bright and modern 2-bedroom, 2-bath home located in the desirable Breezeswept Beach Estates on Ramrod Key. Completed in 2024 by the builder with high-qual...
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 ...
Well-maintained elevated home offering the perfect combination of comfort, functionality, and peace of mind. Built above flood elevation, this move-in-ready property feat...
Discover a rare combination of privacy, waterfront living, and spacious outdoor enjoyment on this nearly half-acre canal-front property in Big Pine Key. Boasting approxim...
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...
Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about...
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...
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 ...
Located on a clean boating canal in Coral Shores Subdivision. This property is waiting for someone to tear it down and put up their brand-new home. With a full 46 foot se...
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 your waterfront retreat on Ramrod Key, where beautiful open water views, quick ocean access, and exceptional outdoor living create the ultimate Florida Keys li...
Island living comes easy here, with a free community boat ramp, nearby waterfront basin, and natural Lower Keys scenery all close to home. Set on a large 7,814 sq. ft. co...
MOTIVATED SELLER! Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in r...
Great investment opportunity in Little Torch Key! This well-maintained home sits on a clean, clear swimming canal with direct access for paddle boarding, kayaking, and fi...
Escape to your own private tropical oasis in the heart of Big Pine Key. Hidden behind lush mature landscaping and swaying palms, this charming 2-bedroom, 1-bath home offe...
Waterfront duplex located on a wide, deep boating canal with excellent boating access and 60 ft. of dockage, split between both units, offering approximately 30 ft. per s...
********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 laid-back Florida Keys lifestyle in this beautifully maintained, double lot sized at 12,000 sq ft, concrete 2-bedroom, 2-bath stilt home located on a desir...
Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing ...
Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming ...
Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport, and enjoy access to the Blanche Bergin Marina Park, complete...
OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, jus...
Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an...
It's your lucky day! The last buyers had to cancel their contract for personal reasons prior to inspections. Whether you enjoy fishing and diving or prefer kayaking and p...
Homes offering this level of detail, space & modern construction are a rare find in the Lower Keys. Built in 2023 in desirable Pine Channel Estates, this exceptional wate...
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...
Enjoy the laid back Big Pine Key lifestyle. Situated on an expansive 11,500 square foot lot, this beautifully updated 2 bedroom, 2 bath home offers space, comfort, and th...
Welcome to your perfect Florida Keys retreat! Situated on a spacious 5,250 s/f lot, this versatile waterfront property offers two separate living units, making it ideal f...
Big Pine charm with this newer construction 2021 Affinity home that is turn-key and sits on a stunning double lot with plenty of extra outdoor space. It has 3 bedrooms, 2...
Well-priced Keys living starts here! This 12,500 sq. ft. double lot offers ample parking and room to add a pool, garage, tiki hut, or more. In 2022, the current owner add...
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 ...
Welcome to your private paradise in the Lower Keys! This beautifully updated 2-bedroom, 2-bathroom two-story home offers the ultimate island escape with unmatched privacy...
Waterfront living meets comfort and functionality in this move-in ready canal front home. Offering 120 feet of concrete dockage in a deep water canal. Quick boating acces...
Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, f...
This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramr...
On a quiet dead-end street in the highly sought-after Sugarloaf Shores community, sits this fully renovated tropical retreat thats reminiscent of something straight out o...
Location, location, location. This home has stunning sunrise and ocean views from this one- of-a kind Open Water property. Picture perfect views from theFrench Doors of...
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, ...
Morning Glory - The Dolphin House is one of those rare oceanfront sanctuaries where time softens, stress fades, and every sunrise feels like it was created just for you. ...
Seller Welcomes Offers! Tucked away on a quiet dead-end street in Big Pine Key, this beautifully updated 2-bedroom, 2-bath canal-front home offers the perfect blend of mo...
Affordable Living in the Florida Keys Has Arrived! Welcome to this charming 2-bedroom, 2-bathroom home offering comfortable living space, an open-concept layout, and i...
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...
Extra adjoining lot adds additional seawall frontage and provides plenty of room for a pool, extra recreational space, and additional parking at this beautifully updated ...
Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal living come together beautifully along with the convenience of an interior elevator...
Situated just offshore in the Lower Florida Keys, Cook's Key Lime Cottage offers a sublime blend of modern comfort and tropical allure. Perfect for avid fishermen and out...
NEW CONSTRUCTION! This charming 1,500 sqft home is a true retreat, perfectly positioned in the Lower Keys, just a moments walk from the popular Looe Key Tiki Bar and B...
This recently built canal front home is situated in a highly desirable area of Big Pine just minutes to the open water. The home has a bright open kitchen with plenty of ...
Built in 2019 on a Double Lot! This modern home features three (3) bedrooms and two (2) bathrooms, offering everything you need. It's low maintenance yet packed with amen...
Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Cha...

Jim Signor: 305-394-4449