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2211 San Sebastian Dr, Big Pine
$1,450,000
4 Beds ⋅ 3 Baths ⋅ 620791 MLS
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 home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled pool. The home comes complete with a custom 60 ft boat dock for all your water toys. The custom concrete pool, pool decking and landscaping will be completed within the month and this brand new home also comes with a 1 Year Builders Warranty. The home is perfectly situated for the water enthusiast with world class fishing, diving, snorkeling, paddle boarding and kayaking! Don't wait on this one!!!

2211 San Sebastian Dr, Big Pine
31368 Ave E, Big Pine
$385,000
3 Beds ⋅ 2 Baths ⋅ 620783 MLS
Nestled in a quiet neighborhood on Big Pine Key, this property presents a rare opportunity to create your own Lower Keys retreat. Situated on a spacious 10,000 sq ft lot, the 3 bedroom, 2 bathroom home features an expansive floor plan with all-new sub-flooring already in place, providing a solid foundation for your vision. Whether you're looking to thoughtfully renovate the existing home or take advantage of its ROGO exemption status to build new, the possibilities are yours to explore. Experience the laid-back charm of Big Pine Key, where community parks, local restaurants and bars, shopping, and nearby boat ramps are all just minutes away. This property offers the perfect opportunity to create the island home you've always imagined in a peaceful setting in the Lower Keys.

31368 Ave E, Big Pine
31118 Ave I, Big Pine
$599,000
3 Beds ⋅ 2 Baths ⋅ 620767 MLS
Welcome to laid-back island living in this beautifully updated 3-bedroom, 2-bathroom home on Big Pine Key. Recent upgrades include a brand-new kitchen with stainless steel appliances, along with impact-resistant windows and doors throughout. The home also features a large downstairs enclosure offering abundant space for storage, tools, bicycles, kayaks, and other island essentials. Outside, the lush tropical setting and low-maintenance gravel yard create an inviting outdoor environment without the burden of extensive upkeep. Tucked away in a quiet community, the property is conveniently located near Big Pine Key Community Park, grocery stores, local restaurants, shopping, and everyday conveniences. An assumable VA loan with a sub 3% interest rate may be available to qualified buyers, subject to lender and VA approval. Assumable Flood Insurance 1010 per year, current windstorm 3500!

31118 Ave I, Big Pine
31536 Ave F, Big Pine
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 620761 MLS
If you're looking for a property that can wear many hats, this one deserves a closer look! The Big Pine Key Bungalow sits on a spacious waterfront lot where open-water views and glowing sunrise skies set the tone for every day. Whether you're searching for a full-time residence, a vacation retreat, or a turn-key investment with a well-established vacation rental history, this home offers exceptional flexibility. Full of personality and intentional functionality, this turnkey, fully furnished 3-bedroom, 2-bath home was built in 2019 with hurricane-rated steel construction and upgraded smart home features throughout. The east-facing location captures breathtaking sunrises while offering direct boating access to both the Gulf and Atlantic. Inside, you'll find a bright, modern, and spacious home designed to take full advantage of its incredible surroundings. Large impact-rated windows and doors frame sweeping water views from nearly every room, filling the open-concept living, dining, and kitchen areas with natural light. One of the home's standout features is its versatility. Murphy beds allow guest rooms to effortlessly transform into home offices, hobby spaces, or fitness rooms, making it easy to adapt the home to your lifestyle. Thoughtful storage throughout adds even more everyday functionality. Outside, the adventure continues! Set on a large, fenced double lot with ~100ft of canal frontage, the property offers direct boating access to both the Gulf and Atlantic, putting some of the Keys' best fishing, diving, and exploring right at your fingertips. The property also features low-maintenance artificial turf, a heated saltwater pool, plenty of room for boat storage/RV parking, an outdoor shower, many tropical plants and fruit trees, fishing cleaning station, and all the gear that comes with the Florida Keys lifestyle. Whether your perfect day is spent on the water or simply relaxing poolside, you'll feel right at home here!

31536 Ave F, Big Pine
30881 Witters Ln, Big Pine
$699,000
2 Beds ⋅ 1 Baths ⋅ 620744 MLS
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 and bath and is situated on 3 lots giving you plenty of space. It is only a very short boat ride to Boggie Channel, the only market channel to both the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key, surrounding waters and nature trails. Large 280 square foot utility building with workshop. A short walk to the No Name Pub, a Keys historic watering hole. Don't miss your opportunity for this15000 square foot, 3 lot parcel with a lovely concrete home. Proof of funds or pre-qualification necessary to schedule a showing.

30881 Witters Ln, Big Pine
31032 Hollerich Dr, Big Pine
$899,000
4 Beds ⋅ 2 Baths ⋅ 620607 MLS
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 beautifully maintained waterfront duplex offering the perfect combination of island living and exceptional income potential. Located on a peaceful canal just steps from the Big Pine Community Park, this unique property features two spacious 2-bedroom, 1-bath residences, each with its own private entrance, private outdoor shower, and thoughtfully updated interior. Both units showcase bright, open floor plans with updated kitchens featuring stainless steel appliances, and ample cabinetry, along with renovated bathrooms, comfortable living areas, and spacious bedrooms. Whether you're searching for a primary residence, vacation home, or investment property, this duplex offers endless possibilities. Step outside and enjoy the laid-back Keys lifestyle with tropical landscaping, expansive gravel parking with room for boats and trailers, a detached storage building, and a relaxing canal-front setting perfect for enjoying the ocean breeze. Spend your mornings with a cup of coffee by the water, launch your next boating adventure, or simply unwind in your own tropical oasis. This versatile property is ideal for: -Living in one unit while renting the other -Generating income by leasing both units -Creating a family compound or multigenerational retreat -Seasonal or long-term rental opportunities Conveniently located near the Big Pine Community Park, shopping, dining, world-class boating, fishing, and all the natural beauty the Lower Florida Keys have to offer, this property truly has it all. Whether you're looking to invest, retire, or embrace the island lifestyle full-time, this rare waterfront duplex offers flexibility, charm, and endless possibilities. Own your piece of paradise while letting your investment help pay for it!

31032 Hollerich Dr, Big Pine
550 Pine Ln, Big Pine
$799,000
3 Beds ⋅ 1 Baths ⋅ 620504 MLS
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 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof, and stylish modern finishes throughout. Outside, there's plenty of room to expand, entertain, or simply relax and soak in the serene Keys lifestyle. Located just minutes from shopping, dining, and Big Pine Community Park, this home combines privacy and convenience in one of the Lower Keys' most desirable neighborhoods.

550 Pine Ln, Big Pine
29172 Rose Dr, Big Pine
$695,000
2 Beds ⋅ 2 Baths ⋅ 620469 MLS
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 multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek quartz countertops and newly installed cabinets and backsplash. Both bathrooms have been upgraded. Gorgeous high end tiling in shower and floor, accompanied by new vanities. Throughout the house is luxury plank vinyl flooring and crown molding to make this home shine even more. Off main living area is an expansive back deck for relaxation. Local grocery store, dog park, and food/beverage only minutes away! Like what you see? Call today!

29172 Rose Dr, Big Pine
31179 Ave H, Big Pine
$539,000
3 Beds ⋅ 2 Baths ⋅ 620410 MLS
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 opportunity to stop renting and start owning. Step inside to an open-concept living space and kitchen that overlook the inviting screened-in front porch, creating a bright and open space for everyday living and entertaining. The hallway leads to all three bedrooms, including two comfortable guest rooms and a spacious primary suite with its own bathroom. A second full bathroom is conveniently located near the guest bedrooms. The washer and dryer are located just outside on the front porch for added convenience. This property offers plenty of parking for boats/trailers along with generous storage space on the ground level. The neighboring lots are county-owned, providing extra privacy and preserving the open, spacious feel with no future development immediately next door. Enjoy a short walk to the waterfront or to nearby Big Pine Key Park. Location, Location, Location. Come to Avenue H to see what we are all taking about. Call today!

31179 Ave H, Big Pine
29162 Bougainvillea Ln, Big Pine
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 620361 MLS
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 modern updates and relaxed waterfront living. Enjoy breathtaking sunsets from the screened-in balcony, or head down to the 70 ft dock with a 12,000 lb boat lift, perfect for boating enthusiasts. The fenced-in yard features lush fruit trees and outdoor space to unwind, plus room for an RV with 30 amp service. A spacious downstairs provides plenty of storage, making this home as functional as it is inviting. A rare opportunity to own a move-in-ready waterfront home in a peaceful setting!

29162 Bougainvillea Ln, Big Pine
1615 Fern Ave, Big Pine
$989,000
3 Beds ⋅ 3 Baths ⋅ 620351 MLS
Welcome to an incredible opportunity to enjoy an exceptional amount of home and land in the Lower Keys. This beautifully updated 3-bedroom, 2.5-bath waterfront home sits on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key, offering generous space both inside and out without sacrificing the relaxed Keys lifestyle. Thoughtfully renovated throughout, the home features a bright, spacious living room, versatile office/den, and an updated kitchen and dining area ideal for everyday living and entertaining. Boaters will appreciate canal access to Pine Channel, with quick access to both Atlantic and Gulf waters. The screened porch overlooking the canal is the perfect spot to relax, dine outdoors, or take in the peaceful waterfront setting. Outside, the expansive double lot offers ample room for parking, pets, and outdoor activities, with plenty of space to add a pool and create your own backyard retreat. The open area beneath the home provides incredible flexibility for storage, a workshop, recreational space, or outdoor living. With its generous home size, rare double-lot setting, waterfront access, and versatile lower-level space, this property offers exceptional value in the Lower Keys. Located in a desirable, family-friendly neighborhood, this home captures the best of Big Pine Key living--peaceful surroundings, abundant space, and easy access to the water.

1615 Fern Ave, Big Pine
29424 Forrestal Ave, Big Pine
$1,550,000
3 Beds ⋅ 2 Baths ⋅ 620317 MLS
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 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in plenty of natural light and give the home an open, comfortable feel. Outside, enjoy 75 ft. of canal frontage with a step-down dock, two boat lifts, one of which is rated for 14,000 lbs., and very quick boat access to Pine Channel, the ocean, and the backcountry. The split-bedroom floor plan offers 3 bedrooms and 2 baths; overlooking the canal, the south-facing screened porch provides additional outdoor living. Accordion shutters and a metal roof add peace of mind. Permitted in 2007, the elevator is no longer functional and is being sold as-is. This is a solid, comfortable Keys home where boating, sunshine, and life in paradise are right outside your door.

29424 Forrestal Ave, Big Pine
29034 Rose Dr, Big Pine
$785,000
2 Beds ⋅ 1 Baths ⋅ 620040 MLS
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 Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is filled with natural light and designed for comfortable island living, boasting high exposed-beam ceilings, adding character and depth to the space. The spacious kitchen features solid wood cabinetry, while recent updates to the bathroom, bedrooms, and bedroom flooring give the home a fresh coastal feel. A large pocket sliding glass door disappears into the wall, creating seamless indoor-outdoor living and opening to an expansive covered back porch measuring approximately 36' x 12', perfect for entertaining, dining, or relaxing canal-side. New composite decking and front porch railings were completed in 2024, adding durability and style, and additional updates include a new HVAC system, new tankless water heater, new siding, and new impact windows throughout. The primary suite offers walk-in closets and direct porch access, while the laundry area is conveniently located on the back balcony. Offered with new furnishings both inside and out, this move-in-ready Keys getaway is ideal as a full-time residence, vacation home, or investment opportunity. Don't miss the opportunity to check out this Big Pine Key gem!

29034 Rose Dr, Big Pine
30525 Winifred St, Big Pine
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 620017 MLS
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 oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a boaters dream. Access the Atlantic or Gulf in minutes. 15,000 lb. Boat lift added in 2024. Inside, the home features 1,774 square feet of thoughtfully designed living space with 3 bedrooms and 3 bathrooms. The third bedroom has a private entrance and could be used as guest quarters or an in-law suite. The updated kitchen showcases modern finishes and functionality, while the beautifully renovated bathrooms reflect today's contemporary style and comfort. Spacious living areas and an inviting layout create an ideal environment for both relaxing and entertaining. Impact Windows and Doors. New AC year 2026. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this canal-front property offers the privacy, upgrades, and Florida Keys lifestyle buyers are searching for. Call to schedule your private tour. Sellers are motivated.

30525 Winifred St, Big Pine
30937 Baileys Ln, Big Pine
$799,000
3 Beds ⋅ 2 Baths ⋅ 620011 MLS
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 paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along with its own boat ramp on the side. The frame with stucco upstairs offers 1,380 square feet of living space with 2 bedrooms, 1 bath, and a spacious great room with impressive water views. The original structure has high cathedral ceilings with wood beams and beautiful hardwood floors. Generously-sized, the updated kitchen includes abundant cabinet space, granite countertops, and a large island. The CBS ground level has a grandfathered-in, 600 sq. ft. living area that provides the 3rd bedroom and 2nd bathroom creating an ideal in-law suite; plus 300 sq. ft. devoted to storage as well as the washer and dryer. Impact-resistant windows were installed upstairs in 2021, and new ductless AC/heat systems were added both upstairs and downstairs in 2022. Panel shutters protect the downstairs jalousie windows. Please note that the upstairs and downstairs living areas are not connected by an interior staircase. This long-established neighborhood is also home to local favorites and landmarks including the No Name Pub, No Name Bridge, and the Old Wooden Bridge Resort and Marina with boat ramp.

30937 Baileys Ln, Big Pine
29663 Saratoga Ave, Big Pine
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 620002 MLS
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 waterfront home offers 75' of dockage on a deep, wide canal with quick access to Pine Channel. Tucked in far enough to avoid traffic noise, yet moments from open water, the location delivers the best of the Lower Keys lifestyle. Bonus-Low insurance costs! Designed with both luxury & functionality in mind, this split floorplan home showcases extensive upgrades & designer finishes throughout including crown custom built-ins, crown moulding, recessed LED lighting, upgraded designer fixtures, impact windows & doors, & durable Hardie board siding. The stunning kitchen serves as the centerpiece of the home with quartzite countertops, custom cabinetry, premium finishes & abundant space to gather and entertain, while quartzite carries through the bathrooms for a cohesive upscale feel. The expansive upstairs screened lanai creates an ideal indoor/outdoor living space with designer details throughout and plenty of room to relax, dine & entertain year-round. Downstairs offers expansive covered entertaining areas, outdoor shower, hot tub & 300 sq ft enclosure perfect for storage, tackle room, gym, workshop or additional flex space. True laundry/utility room adds practicality rarely found in Keys homes. Custom closet built-ins throughout. Additional features include a cistern (not currently in use), exceptional indoor & outdoor living space, & a beautifully designed waterfront setting built for boating, entertaining & enjoying the Keys lifestyle. The clear canal water here is a standout rarely found elsewhere. Double framed dock for boat lift. Homeowners/Windstorm=$2,645. Flood=$2,164

29663 Saratoga Ave, Big Pine
3610 S Seas St, Big Pine
$850,000
5 Beds ⋅ 3 Baths ⋅ 619979 MLS
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 for multi-generational living, vacation use, or income-producing potential. The upper level features 3 bedrooms and 2 bathrooms with bright, comfortable living spaces designed for relaxed island living. The lower unit offers 2 bedrooms and 1 bathroom and is currently rented month-to-month for $4,000, with the tenant also utilizing the upstairs portion of the home. This property is loaded with upgrades and features for convenience, security, and outdoor enjoyment, including a shingle roof approximately 8 years old, impact windows throughout, and two elevated A/C units that are less than 4 years old. Boating and recreational enthusiasts will appreciate the 50-foot dock, along with existing preparation for water and electricity service for boats on the canal. Additional highlights include a 16-camera security system, RV preparation, and readiness for an electric vehicle charging station. Perfectly located just a 5-minute walk from the coast, this exceptional property combines waterfront lifestyle, flexibility, and modern upgrades in one incredible Florida Keys opportunity.

3610 S Seas St, Big Pine
31128 Ave G, Big Pine
$799,000
3 Beds ⋅ 2 Baths ⋅ 619969 MLS
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 bathrooms, porcelain tile floors throughout, a beautiful open kitchen for entertaining and a large patio in the front of the house with a sliding door that let in a wonderful breeze in the evenings. The extra space that the double lot provides gives this property incredible potential for endless possibilities such as a pool, or tiki and whatever else your heart desires to create your very own tropical oasis. Fencing is in place on the sides and rear and partially fenced in at the front. Located just a few blocks from Big Pine Key Park that offers a playground, bike path, skate park, shuffleboard, basketball courts and pickleball courts. There is plenty of parking underneath the house on a concrete slab with a newly constructed enclosure with an 8 foot wide powered garage door with battery back-up. This enclosed space provides plenty of storage space for all your outdoor, fishing and boating equipment. The boat ramps are conveniently located minutes away and are free. The state road 4A ramp on Little Torch is also a great option and is only a 7-minute drive. Property is for sale unfurnished however the washer, dryer, and upstairs appliances are being sold with the home. Just a short drive to Marathon and Key West.

31128 Ave G, Big Pine
3746 Park Ave, Big Pine
$1,149,900
2 Beds ⋅ 2 Baths ⋅ 619915 MLS
SELLER WILL GIVE A $20,000.00 BUYER CLOSING CREDIT! 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 -- no direct neighbors on any side, just peaceful surroundings, tropical landscaping, and the charm of the native Key Deer. Designed for true Florida Keys living, the outdoor space is a showstopper. Enjoy a brand-new heated concrete pool, concrete dock with both a boat lift and jet ski lift, and an elevated sundeck perfect for sunbathing or taking in serene canal views. The professionally landscaped backyard creates a lush tropical retreat complete with paver decking and a tiki hut ideal for entertaining or relaxing poolside. Inside, the home features numerous upgrades and renovations throughout. The fully enclosed and renovated ground level provides excellent guest accommodations, entertaining space, and additional storage, along with a separate laundry room for added convenience. Both levels are equipped with impact windows and doors, as well as electronic roll-down screens for shade and storm protection. Whether you're boating, entertaining, relaxing by the pool, or enjoying the surrounding wildlife, this exceptional property captures the very best of Lower Keys waterfront living.

3746 Park Ave, Big Pine
3674 S Seas St, Big Pine
$864,000
2 Beds ⋅ 2 Baths ⋅ 619841 MLS
Set in the peaceful, natural surroundings of Port Pine Heights, this thoughtfully updated home offers the relaxed, unhurried lifestyle that makes this Lower Keys community so desirable. Over $100,000 has been invested in updates and improvements, allowing the next owner to enjoy a beautifully refreshed home without the time, expense, and uncertainty that often come with renovating. Recent updates include a reimagined kitchen layout with new cabinetry and quartz countertops, beautifully renovated bathrooms with tiled showers and new vanities, new composite decking with sleek aluminum railings. The screened porch has been upgraded with micro-mesh screening, while fresh interior and exterior paint, updated fixtures, and thoughtful finishing touches complete the improvements throughout. Boaters will appreciate the quick, convenient access to Pine Channel and Contents Key, making days on the water easy to enjoy. This home also offers an impressive 702 sq. ft. of fully air-conditioned storage space below, providing exceptional flexibility for storage, hobbies, gear, or additional workspace. Move-in ready, thoughtfully updated, and wonderfully connected to the laid-back beauty of island living.

3674 S Seas St, Big Pine
31342 Ave I, Big Pine
$899,000
1 Beds ⋅ 1 Baths ⋅ 619787 MLS
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 cabinets, stainless appliances, attractive tile backsplash and built in table with seating overlooking the living area.......From the bedroom with adjoined bathroom there are partial ocean views. There is also a utility room with walk-in closet and washer/dryer next to the bedroom......for convenience and easy maintenance there are impact windows and doors and ''Hardie board'' siding.......There is a wrap-around screened porch from which to enjoy views of the canal and partial open water view.......The very spacious 5250 sf lot with 70 ft of seawall benefits from having a large storage enclosure plus carport and plenty of room for an RV, trailer storage or to build a pool.

31342 Ave I, Big Pine
29562 Saratoga Ave, Big Pine
$1,435,000
4 Beds ⋅ 2 Baths ⋅ 619761 MLS
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 Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and furnishings are negotiable in the sale. This elevated, solid concrete home offers quick access to both the Ocean and Gulf, just minutes from world-class adventures! Designed with the serious boater in mind, the property features a 75' concrete seawall, a 17k lb. boat lift, fish-cleaning station, and step-down dock for easy loading. This expansive 4-bed, 2-bath home is ideal for entertaining, with oversized common areas that flow seamlessly for memorable gatherings. The third-floor loft, currently used as a bonus bedroom, offers 360-degree views and a private retreat, while main-floor bedrooms are generously sized with walk-in closets for ample storage. The kitchen is well appointed with a double oven, sprawling counter space, walk-in pantry, and room to host with ease. Unique details throughout include a custom etched mirror in the primary bath that adds coastal charm. Step outside and embrace the Keys lifestyle! A spacious porch, accessible from both the living area and primary suite, is perfect for open-air dining and relaxing water views. Downstairs, the ultimate entertaining area includes a full bar with TV, a large swim spa, plus a 500 lb. ice machine and bait freezer for added convenience. The thoughtfully landscaped yard offers privacy and function, boasting a fenced backyard and ample space for RV or trailer storage. Covered parking provides unique, direct interior access out of the elements. Located in a quiet neighborhood close to dining and shopping, this home blends tranquility with convenience. It is more than a home; it is a waterfront escape ready to be enjoyed!

29562 Saratoga Ave, Big Pine
30363 Flamingo Ln, Big Pine
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 619740 MLS
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 the heart of world-class fishing and diving. Located just a few miles from Bahia Honda State Park, you're ideally positioned for elite tarpon fishing, backcountry action, reef trips, and offshore runs. The dock is built for serious fishermen, featuring a 50' concrete seawall, 15,000 lb boat lift, fish cleaning station, underwater fish lights, and a shaded dockside area with crank out awning, everything you need for seamless days on the water. Built in 1993 with solid concrete construction, the home is designed for durability and comfort, with impact windows and doors, a new metal roof, updated A/C system, and thoughtful upgrades throughout. Inside, you'll find a spacious primary suite with California closet system, whirlpool tub, walk-in shower, and dual sinks, along with two oversized screened lanais to enjoy the coastal breeze. The ground level offers over 1,100 sq ft of enclosed garage space, perfect for storing gear, tackle, and water toys, along with a 250 lb ice maker, multiple freezers. Additional features include a cargo lift, whole-house water filtration and softener system, and tankless hot water. After a long day on the water, unwind just a few minutes walk away at No Name Pub, a local favorite known for its laid back Keys vibe. This is more than a home, it's a Keys Fisherman's paradise Built like a fortress!

30363 Flamingo Ln, Big Pine
3742 Seagrape St, Big Pine
$4,650,000
3 Beds ⋅ 3 Baths ⋅ 619696 MLS
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 grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, plus a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip, set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, this is ultimate Keys living without compromise!

3742 Seagrape St, Big Pine
30461 Poinciana Rd, Big Pine
$465,000
3 Beds ⋅ 2 Baths ⋅ 619695 MLS
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 condition units, abundance of natural lighting, French doors leading to a large screened in porch, great entertaining area. A large primary bedroom has another screened in porch off the back that is shared with separate1/1 guest suite. Separate entrance The bonus room was being used as a child's bedroom. A detached storage shed in the back yard as well. The double lot provides privacy and the potential for more storage and a pool.

30461 Poinciana Rd, Big Pine
29131 Watson Blvd, Big Pine
$975,000
2 Beds ⋅ 2 Baths ⋅ 619692 MLS
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 expansive deck overlooking the canal. Both bedrooms also have doors leading to the wrap around deck! The cathedral ceilings and wood trims give this home beach cottage character! The lower level has an amazing amount of storage with built in shelving. The canal side of the property boasts both a new 40 ft dock with a 10,000 lb. boat lift and a seawall. Easy access to open water! You won't believe the size of this property, plenty of space to park your boat trailers or put in a huge inground pool. Eden Pines is truly a sought after neighborhood, with lots of wildlife everywhere including your daily key deer visitors!

29131 Watson Blvd, Big Pine
30375 Oleander Blvd, Big Pine
$539,900
2 Beds ⋅ 1 Baths ⋅ 619516 MLS
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. ft. gem features a new roof, updated electrical, stainless steel appliances, and fresh paint inside and out. Enjoy a screened-in porch and a private backyard oasis with a putting green, gazebo, and lush landscaping. Plenty of room for a large RV and boat, plus a storage shed for all your gear. Surrounded by the Key Deer Refuge for exceptional privacy and located near the iconic No Name Pub. Your slice of paradise awaits!

30375 Oleander Blvd, Big Pine
29175 Violet Dr, Big Pine
$685,000
3 Beds ⋅ 2 Baths ⋅ 619422 MLS
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 fully updated 3-bedroom, 2-bathroom stilted sanctuary in the heart of Big Pine Key. This home is tucked into the vibrant, family-oriented community of Eden Pines Colony-a neighborhood where neighbors are friends and the island lifestyle is at its best. Boating: The boat ramp is just around the corner and there is plenty of room to park your toys including a one car garage! EXPANSIVE STORAGE BELOW, fully enclosed. Designer Bathrooms: Both the primary and main bathrooms feature beautifully updated showers. Flooring runs through the entire interior and flows seamlessly onto the porch for a high-end, unified look. Updated with newer stainless-steel appliances and an open-concept layout flooded with natural light. Total Comfort: (2019) central AC system replaced. Curated Outdoor Living & Durability: Fresh & Low Maintenance: The home shines with a freshly painted exterior and vinyl hand and porch rails -no rust, no rot, just island beauty. Private Side Yard Oasis: Discover a stunning side yard retreat featuring authentic Key West bricks set against a lush, towering wall of tropical plants. Clean Curb Appeal: An expansive concrete driveway provides plenty of room for multiple vehicles, boat trailers, or RV parking. Upgraded Porch: Expand your living area to the porch! The perfect vantage point for watching the local Key Deer wander and enjoying unbeatable sunrises. Unbeatable Protection & Savings: Current owners receive all mitigation discounts on wind insurance. Fully protected with impact shutters and a durable metal roof (completed in 2019), offering maximum safety and substantial insurance discounts.

29175 Violet Dr, Big Pine
1540 Lantana Ln, Big Pine
$899,000
3 Beds ⋅ 2 Baths ⋅ 619410 MLS
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, dining, and kitchen areas. Lovely, updated kitchen and baths. New beautiful floors, along with impact windows, doors and metal roof. Enjoy swimming in the above ground pool, relaxing on the deck, cocktails at the outside bar, or meeting the adorable friendly key deer roaming the neighborhood. Beautiful yard with room for boats, trailers, and more. The three vacant lots next door to the home are purchased by the County for preservation. This home is completely furnished along with lots of extras included. This house is magical! Successfully rents for $9500.00 during season.

1540 Lantana Ln, Big Pine
29635 Saratoga Ave, Big Pine
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 619377 MLS
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, comfort, and laid-back Keys living. Constructed with poured concrete floors and designed for peace of mind, the home features a tiled interior, a tiled roof, and convenient accordion shutters throughout. Step outside and embrace the tropical lifestyle, lush surroundings, charming paver walkways, and multiple spaces designed for relaxation and entertaining. Unwind in the screened porch as ocean breezes roll through, or soak your cares away in the hot tub beneath the stars. A cozy gazebo creates the perfect shaded retreat for afternoon cocktails or morning coffee. For boating enthusiasts, this property is a dream come true. Enjoy quick access to open water with your private seawall and boat lift, making every day a perfect day to be on the water. Additional storage provides room for all your gear, from fishing rods to paddleboards. Whether you're seeking a full-time residence, weekend escape, or investment opportunity, this home captures the essence of tropical living where every day feels like a vacation.

29635 Saratoga Ave, Big Pine