Homes on Big Pine Key are waterfront and non-waterfront, which explains the wide range of asking prices. As the first substantial residential island south of the 7-mile bridge, Big Pine Key offers shopping, restaurants, banking, and more while also having the "old Keys" ambiance that many homeowners desire. Big Pine Key is particularly famous for the Key Deer that roam the island.
Active listings of homes for sale on Big Pine Key are shown within this list of Big Pine Key neighborhoods.
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...
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 ...
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...
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...
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...
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...
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...
Great opportunity to build in desirable Cahill Pines and Palms subdivision in Big Pine Key on swimming canal. Plugged canal nestled in a community of homes close to shopp...
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 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 ...
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...
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...
Opportunity to Own a Thriving Bicycle Business in the Beautiful Florida Keys! The Big Pine Bicycle Center, serving the Lower Keys for nearly 30 years, is a profitable,...
Excellent opportunity to own a clean, well-maintained RV lot in a desirable Big Pine Key RV community. This commercially zoned, transient lot allows for daily, weekly, or...
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...
Commercial waterfront lot at 29517 Big Pine St, Big Pine Key. Deep-water canal with quick access to both the Gulf of Mexico and the Atlantic Ocean, icommercial fishing, m...
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...
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 laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming ...
Vacant waterfront lot in the desirable Doctor's Arm neighborhood of Big Pine Key. This cleared lot has 55 feet of canal frontage, plenty of room for a seawall and your bo...
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 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...
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...
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...
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...
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 ...
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...
Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete waterfront home offers quick access to both the Atlantic and Gulf, putting you in...
Escape to your slice of paradise with this stunning 3-bedroom, 2-bath home! Nestled on a spacious 7,500 sq ft lot, this beautiful property offers ample room for your RV o...
Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer'...
Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural ...
Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 bath home, with an office, features a vaulted ceiling, new mini split air conditi...
Peaceful serenity found on this 22,077 square foot property with a cozy two bedroom one and one-half bath. Open concept large kitchen and living room leading out to the e...
Welcome to your slice of paradise in the highly sought-after neighborhood of Eden Pines on Big Pine Key! This solid concrete construction home offers 2 bedrooms, 2 bathro...
Island Living in Big Pine Key! Charming and updated 2-bedroom, 1-bath concrete block home on an oversized, fully fenced lot just one block from the water. This 816 sq...
Experience the pinnacle of Florida Keys waterfront living in this newly constructed (2023) open water home on Big Pine Key. Perfectly positioned to capture breathtaking s...
Rare opportunity to acquire six contiguous commercially zoned lots totaling approximately 31,500 square feet in Big Pine Key. Offered as one combined property, this 150' ...
Eden Pines Gem: Fully updated, low assumable flood Modern Island Living: Updated Stilted Retreat in Golf-Cart Friendly Eden Pines! Welcome to 29175 Violet Drive, a...
Bring your boats to this beautifully furnished canal front home. TURN KEY READY! Secluded on a corner large lot with 190 ft. of concrete dockage. Large and open living, ...
Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This beautifully built 3bedroom, 2bath CBS home offers the perfect blend of durability, ...
Enjoy easy island living in this beautifully updated 2BD/2BA elevated home set along a peaceful plugged canal--perfect for paddleboarding and enjoying the waterfront ambi...
Big Pine Key Pool Home - Nature Lover's Paradise! 3BR/2BA single-family home with pool, outdoor kitchen, and gazebo -- perfect for entertaining and enjoying the Florida...
This 4-bedroom, 2-bath, 1566 sq. ft. home has so much to offer for the price! A spacious living area separates the primary bedroom and ensuite bath from the remaining bed...
Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordon Road is an elevated 2BR/2BA waterfront retreat in Big Pine Key offering the li...
Turnkey and move-in ready, this exceptional waterfront home is being offered fully furnished--including furniture, dishes, cookware, and linens--so you can start enjoying...
Discover the potential in this 2 bedroom, 1.5 bathroom mobile home located in the heart of Big Pine Key! Perfect for first-time buyers or savvy investors, this property o...
Located in the peaceful National Key Deer Refuge, this charming 2BD/2BA canal front home in Eden Pines offers the perfect blend of tranquility and classic Florida Keys li...
Tier 2 parcel with potential eligibility for ROGO points toward future building permits in Monroe County. Buyer to verify ROGO point availability and requirements with Mo...
Tier 2 parcel with potential eligibility for ROGO points toward future building permits in Monroe County. Buyer to verify ROGO point availability and requirements with Mo...
Enjoy Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers the perfect opportu...
Triton Sea Center represents one of the most compelling marina acquisition opportunities in the Florida Keys. Strategically located at 29740 Overseas Highway in Big Pine ...
A true tropical oasis nestled on a 6,600 sq ft lot with lush landscaping and a mature mango tree. Make this well maintained property your new home or INVESTMENT property....
Build Immediately with Active Building & Pool Permits Included. This Bay Front/Gulf Front open-water lot offers 14,746 sq. ft. of waterfront opportunity with beautiful wi...
48k Price Improvement from original Listing, Priced to SELL, Motivated Seller, Bring all Offers. Sportsman Paradise. 2 Bedroom House with Permitted Concrete BOAT RAMP, co...
An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcase...
DOUBLE LOT waterfront opportunity in Big Pine Key! This charming 2 bedroom, 2 bathroom home is ideally situated on a fenced double lot along a canal with excellent boatin...
Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3...
Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? ...
This meticulously maintained 3-bedroom, 3-bath home in Big Pine Key offers exceptional privacy with state owned non-buildable land on both sides of this tranquil proper...
Welcome to island living in Big Pine Key. Situated on a desirable corner lot, this beautifully remodeled 3-bedroom, 2-bathroom home offers 70 feet of dockage with davits,...
Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both ...
Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft h...
Transferable ROGO Exempt Building Right + 2,250 Sq Ft Lot - Build Immediately! Rare opportunity to own a ROGO-exempt parcel in the Florida Keys, allowing you to build ...
Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boatin...
Open Waterfront Double Lot with Protected Boating and Endless Possibilities Discover the best of Florida Keys waterfront living on this spacious double lot located on ...
**PRICED RIGHT RESORT SETTING** Adorable charm and the essential Florida Keys lifestyle can be found in this 1-bedroom, 1-bathroom island bungalow. Nestled in the heart ...
Beautifully Renovated Single-Family Home in the Florida Keys This stunning 2-bedroom, 2-bathroom home with extra guess room downstairs, fully renovated in 2024, is perfec...
Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key. Featuring a garage and tons of storage inside...
Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water—just minutes to both the Gulf and the Atlant...
Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meets income opportunity. This beautifully updated waterfront pr...
Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meets income opportunity. This beautifully updated waterfront pr...
Nestled at the quiet end of a peaceful street, this beautifully maintained home offers the blend of island charm, privacy, and modern comfort. Surrounded by graceful Arec...
Dolphinus del Sol is a Waterfront Estate Masterpiece! Enjoy this custom, ultra-modern smart home! This new construction, solid precast concrete home, offers unparalleled ...
Custom-built 2-bedroom, 2-bathroom home (1987) situated on a boating canal in the sought-after Eden Pines neighborhood of Big Pine Key where the Key Deer roam. Short ...
Big Pine Key Here's your opportunity to get into a 3 Bedroom. 2 Bath stilt home in the Keys. Metal Roof. Brand New Central A/C & Heat. Sliding door from dining area to Co...
Welcome to this Key West-style home located on Big Pine Key! Situated on a generous 7500 square-foot fully fenced lot, this property offers ample space for parking and st...
Welcome to this elevated 3-bedroom, 2-bath home located in a quiet neighborhood in Big Pine Key. This well-maintained property features an open concept living and kitchen...
**Price Improvement** Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebu...
Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot...
If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provid...
Welcome to your island retreat in the sought-after community of Port Pine Heights on Big Pine Key. This charming stilted waterfront home offers quick boating access to Pi...
Wake up to endless water views and wind down with breathtaking Keys sunsets at this peaceful island retreat. Set on a quiet corner lot, this 3-bedroom, 3-bath home offers...
Prime commercial property just 30 minutes from Key West, located in the heart of Big Pine Key. This rare offering includes 35,475 sq. ft. of commercial land with 215 feet...
Commercial Zoning Tier 1 Wooded lot
Back on the market! Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. ...
Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuring a two-bedroom, two-bath main house and a one-bedroom, one-bath guest cottage ...
Prime Commercial Fishing Property in the Florida Keys! Discover a rare opportunity to own and operate a commercial fishing business in the coveted Commercial Fishing S...
Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors enhancing the large...
Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows a...
GREAT INVESTMENT OPPORTUNITY! $849,000 Best price property in Pine Channel Estates, Big Pine Key. Fully furnished. Remodeled 2 bdrm/2 full bath + BONUS room (3rd bdrm/of...
Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access...
This is a large Modular HOME on Big Pine Key that is permanently affixed to concrete pilings and is elevated above the 8' flood plain-which helps keep flood insurance rea...

Jim Signor: 305-394-4449