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$763,000
4 Beds 2 Baths 621188 MLS
This spacious Big Pine Key home is situated on a lushly landscaped 12,500 sq. ft. double lot and offers 2,136 sq. ft. of living area with 4 bedrooms, 2 baths, fresh interior colors and decor, solid bamboo and tile flooring. The expansive layout has plenty of room for family and guests, including a breakfast room, a walk-through dressing room off the primary bedroom, and laundry/utility room. The tasteful furnishings convey with only a few exceptions. Central A/C cools and heats most of the home, with supplemental mini-split units serving the remaining areas. Enjoy outdoor living in the fenced backyard with tiki hut, perfect for relaxing or entertaining. County- and state-owned protected land borders two sides of the property, providing an added sense of privacy. The detached garage is a wonderful bonus!

30374 Oleander Blvd, Big Pine

$950,000
3 Beds 3 Baths 621180 MLS
Brand-New Waterfront Home in the Florida Keys Discover the ultimate Florida Keys lifestyle in this stunning brand-new construction, perfectly designed for those who love boating, waterfront living, and the beauty of the Gulf. This exceptional property features 3 spacious bedrooms, 2.5 bathrooms, and a private boat dock, providing direct access to the Gulf for unforgettable days on the water. The home offers generous parking space and is being sold fully furnished, allowing you to move in and immediately enjoy everything the Keys have to offer. From the modern finishes and comfortable living spaces to the incredible waterfront setting, every detail was designed for relaxation and enjoyment. Step outside and enjoy your own private waterfront paradise, with your boat just steps from your door and direct access to the Gulf. Whether you're looking for a luxurious primary residence, a vacation retreat, or an exceptional investment opportunity, this property offers the perfect combination of new construction, boating access, comfort, and the laid-back Florida Keys lifestyle. Your dream home on the water is ready to welcome you home.

31490 Ave F Unit Avenue F, Big Pine

$1,199,000
3 Beds 2 Baths 620836 MLS
Experience the keys waterfront lifestyle! This charming 3 bedroom, 2 bath home has peekaboo views of Big Pine Bight and is minutes away from Bogie Channel with NO limiting bridges to slow you down. Only 2 minutes to the Atlantic, and direct access to the Gulf. Equipped with a 10,000 LB boat lift, the boat is also available as a separate purchase. The buyer will get first right of refusal on the boat. There is a separate nicely sized storage room that could also be a workshop. The garage is currently set up as bonus space, it would make a great 'man cave', or play room! This Key West style home is being offered fully furnished as well as an extensive list of required amenities, such as a fully stocked kitchen, bedding and bath towels, to name a few. Bring your toothbrush and fishing rods, drop a line off of the seawall and catch your dinner, or walk to the famous No Name Pub for pizza and adult beverages. Or, enjoy a quiet evening under the stars, in your private heated pool, grilling your catch of the day. The outdoor patio is expansive, private and fenced in, with a puppy area for ease of relaxing for everyone! Newer roof, A/C, and hot water heater.

1657 Watson Blvd, 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

$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

$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

$1,695,000
3 Beds 2 Baths 620330 MLS
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 offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living. Outdoors, the home transforms into a resort-style retreat. Enjoy a heated saltwater pool, expansive decking, and a wonderful poolside tiki hut perfect for entertaining or unwinding in the shade. Mature palms and lush tropical landscaping create a peaceful, secluded atmosphere. The fully fenced yard is secure for pets and even has a large parking spot perfect for a boat on trailer or an rv. Boating enthusiasts will appreciate the private concrete dock, and easy access to the pristine waters of the Lower Keys. Some of the absolute best kayaking and paddleboarding spots are just minutes away. With generous 1900 sq ft garage and storage space there is room for all your island toys! This turnkey waterfront escape delivers the perfect blend of comfort, beauty, and adventure. Learn more about Tropical Bay Community: www.TropicalBayEstates.org Owner has obtained ACOE and DEP permits to expand the dockage across the second lot if a buyer wants to add more than the existing 75'.

30463 Hawk Ln, 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

$1,199,000
4 Beds 3 Baths 620193 MLS
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 approximately 130 feet of waterfront, this unique location at the end of the canal offers minimal boat traffic, easy boating access to both the Atlantic Ocean and Gulf waters. Set behind lush tropical landscaping and a gated entrance, the fenced 19,762-square-foot lot creates a private retreat surrounded by mature palms, fruit trees, orchids, and vibrant native plantings. The heated swimming pool serves as the centerpiece of the outdoor living area, complemented by a large screened patio perfect for relaxing, entertaining, or enjoying the peaceful garden setting. Designed with boaters and outdoor enthusiasts in mind, the property offers ample room for multiple vessels, RV parking, and trailer storage, with convenient access through a separate gate. The ground-level residence spans approximately 2,166 square feet and features four bedrooms, two and one-half updated bathrooms, an upgraded kitchen, laundry room, impact-resistant windows and doors, a newer mini-split air conditioning system, and a ceramic tile roof installed in 2017. Additional highlights include abundant storage space, a dedicated workshop area, and extra refrigeration and freezer capacity for fishing gear and supplies. Offered furnished, this home is ready to be enjoyed from day one. Located just a short distance from Big Pine Community Park, residents can enjoy pickleball, tennis, basketball, walking paths, playgrounds, waterfront picnic areas, and community events. Whether you're seeking a full-time residence, vacation home, or private waterfront escape, this property offers the space, seclusion, and Keys lifestyle that are becoming increasingly difficult to find.

30985 Hibiscus 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

$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

$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

$2,200,000
3 Beds 2 Baths 619483 MLS
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 sunrise views, this CBS-built residence offers a seamless blend of modern coastal design, durability, and effortless indoor-outdoor living. Spanning 1,834 square feet, the home features 3 Bedrooms and 2 Bathrooms, thoughtfully designed with soaring 10-foot ceilings, 8-foot doors, and expansive impact-rated windows and doors that invite in natural light while framing panoramic water views throughout the living spaces and Primary Suite. The heart of the home is the stunning chef's Kitchen, appointed with white quartz countertops, stainless steel appliances, custom cabinetry, and an oversized dining bar--ideal for entertaining guests or enjoying casual waterfront dining. The Primary Suite serves as a tranquil retreat, complete with sweeping water views, a spacious custom walk-in closet, and a beautifully finished modern Bathroom. Outdoors, the property transforms into a private resort. A large waterfront Pool overlooks the open water, while the 75-foot Concrete Dock with a protected cut-in Boat Slip provides exceptional boating convenience with deep water access to both the Gulf and Atlantic via Bogie Channel, renowned for its excellent fishing. Offered fully Turn-Key and rental ready, this property is perfectly suited for a luxury second home or income-producing investment. As a newer construction, it also benefits from lower insurance costs, an increasingly valuable advantage in the Keys. Located in Big Pine Key, home to serene nature preserves, the famous Key Deer, and convenient shopping and dining, you are also just minutes from the pristine beaches of Bahia Honda State Park.

1631 Sunrise Dr, 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

$1,195,000
3 Beds 2 Baths 619184 MLS
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 the Florida Keys lifestyle from day one. Situated on an oversized 18,000 sq. ft. double lot with 150' of canal frontage in a quiet, peaceful Big Pine Key boating community, this solid concrete 3BD/2BA home features a desirable split floorplan, tile floors, granite countertops, ample storage, attached garage, impact windows and doors, accordion shutters, and a metal roof. Boaters will love the easy access, including a 75' concrete dock with a 17,000 lb boat lift. The sellers have plans to extend the concrete seawall across the second lot, creating the potential for an additional 75' of dockage. Enjoy outstanding access via Bogie Channel with quick routes to both the Atlantic Ocean and Gulf waters, putting world-class fishing, diving, sandbars, and minutes to Bahia Honda State Park and beach. Outdoor amenities include screened and open porches, a tiki hut, outdoor shower, fenced yard, 50-amp RV service, and abundant parking for boats, trailers, and recreational equipment. The spacious double lot and tranquil setting create the perfect backdrop for relaxing island living while still being close to all the Lower Keys has to offer. A rare opportunity to own a fully furnished, move-in ready waterfront home with exceptional boating access and future dockage potential in the Lower Florida Keys. The unique community zoning allows for marine business and income potential from marine-related services.

29534 Geraldine St, Big Pine

$800,000
3 Beds 2 Baths 618879 MLS
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. Currently in a successful vacation rental program. Fenced in for privacy and that sense of peace and tranquility. The backyard features a 14 x 30 custom concrete POOL with heater, chiller and colored lights. 7 x 7 spa tub and waterfall. Downstairs enclosure storage 20 x 34. Plenty of room for parking with RV parking and connections. 3 bedrooms and 2 bathrooms with 1360 sq ft of living space. Double French doors and impact resistance windows allow natural light throughout the home. Spacious open floor plan. Kitchen updated with white corian counter tops, backsplash and bar. Hall bathroom updated with fully tiled walk in shower and glass door. Upstairs covered balcony patio with plenty of space for dining outdoors and entertaining guests. Located on a plugged canal for convenience of kayaking, paddle boarding or swimming from your 15 x 40 foot wooden dock. This is not a boating canal. Local boat ramps are within 5 - 7 minutes. This island gem is being offered turn key, ready for you to start living your paradise lifestyle. It's truly a must see! Call for your private showing today.

216 Newfound Blvd, Big Pine

$475,000
1 Beds 1 Baths 618225 MLS
**PRICE ENHANCEMENT FOR THIS RESORT -STYLE SETTING** Adorable charm and the essential Florida Keys lifestyle can be found in this 1-bedroom, 1-bathroom island bungalow. Nestled in the heart of Big Pine Key, this home offers the perfect blend of cozy comfort and tropical serenity, making it an ideal full-time residence, weekend retreat, or savvy investment property. Home Highlights: Classic Bungalow Charm: An inviting open layout that maximizes space and natural light. Peaceful Setting: Situated in a quiet neighborhood known for its natural beauty and frequent visits from the endangered Key Deer. Outdoor Living: Plenty of room on the lot for boat storage, gardening, or creating your own tiki hut oasis. Low Maintenance: A manageable footprint that allows you to spend less time on chores and more time on the water. Location, Location, Location: Life on Big Pine Key is all about the Great Outdoors. You are just minutes away from: Nature trails, parks and boat ramps! Bahia Honda State Park: Home to some of the best beaches in the Florida Keys. World-Class Boating & Fishing: Quick access to both the Atlantic Ocean and the Gulf of Mexico. Local Favorites: Enjoy nearby tropical dining, local marinas, and the unique shopping of the Lower Keys. Whether you're looking for a peaceful 'Keys Cottage' to call your own or a basecamp for your aquatic adventures, 31478 Avenue E is a rare find at an accessible price point. Schedule your showing today and start living the island dream!

31478 Ave E, Big Pine

$2,150,000
3 Beds 3 Baths 617619 MLS
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 with views over Bogie Channel. Enjoy leisurely days entertaining under the large poolside tiki hut or on the covered platform at the end of the 463-foot pier—perfect for relaxing with family and friends while watching sunsets after a fun day on the water. The platform is equipped with a boat lift, floating jet ski dock, and an outdoor kitchen. The completely renovated, two-story CBS main home offers a spacious 1,950 sq. ft. living area with enough space to possibly add a third bedroom if needed. Large impact-resistant windows allow for views of peaceful sunrises and moonrises over the property and open water. The updated 536 sq. ft. frame-stucco guest cottage gives visitors their own comfortable retreat. Thoughtfully planned lighting enhances the 35,330 sq. ft. fenced property. Monroe County's small Palm Villa Park borders the southern edge, and the County owns the land directly across the street to the north, intended to remain undeveloped. Move-in ready and tastefully furnished, this tranquil slice of paradise is just minutes from local shops and restaurants, and only 30 miles from lively Key West. (Note: Living Area Sq. Ft. Source is the Property Record Card.)

30468 Oleander Blvd, Big Pine

$849,000
2 Beds 2 Baths 618629 MLS
Seller's Motivated!! Bring Offers!! Well established, highly sought out waterfront community Pine Channel Estates, Big Pine Key. 2 bdrm/2 full bath + BONUS room (3rd bdrm/office/sunroom). 75' Canal frontage. All new SS appliances. Metal roof, impact windows and garage door, vinyl siding, tankless water heater, gutters, hurricane shutters, fence, covered patio, large garage and RV/Generator hookups. Generous and impressive one level living space is perfect for entertaining and family gatherings. Deep canal, quick open water access to the ocean and back country for stellar world class fishing, lobstering, diving and snorkeling. Loads of parking. Bike to the nature park, shops, restaurants, water sports, groceries and pharmacy. Take a short boat ride to KiKi's for a delicious meal and live music. 30 minutes to Key West! This property is elevated and ideal as a primary, second or investment. Use your creativity when enhancing your island style to the vast outdoor canvas with a pool/tiki hut. Own your slice of paradise in the Florida Keys today!

29544 Independence Ave, Big Pine

$2,499,000
3 Beds 4 Baths 618739 MLS
Spectacular Open-Water Retreat with Unmatched Sunset View This exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve. The property features over 200 feet of concrete seawall, a 35' x 15' boat basin making it ideal for waterfront living. Step inside this impressive concrete-built home, where water views surround the main living area. The spacious living room showcases vaulted wood ceilings and abundant natural light. The home offers three en-suite bedrooms, plus an additional full bath conveniently located off the kitchen. Designed for true Florida Keys living, the resort-style in-ground pool and tiki hut are perfectly positioned to take in the spectacular western sunset views, creating an unforgettable setting for relaxing evenings and waterfront entertaining. Additional highlights include: Impact windows and slidersLarge attached garage Separate utility/storage building Exceptional privacy Direct ocean access This is a rare opportunity to own a private, west-facing luxury estate that seamlessly blends modern construction, boating convenience, and breathtaking sunset views.

29581 Richard Rd, Big Pine

$1,800,000
3 Beds 2 Baths 618850 MLS
Waterfront, furnished, and ready to enjoy! This beautifully maintained 3-bedroom, 2-bath concrete block home combines comfort, durability, and the relaxed Florida Keys lifestyle. Impact windows and sliding glass doors provide added peace of mind, while the spacious living area flows easily into the dining space. Triple sliding glass doors open to a screened waterfront patio--an inviting setting for dining, entertaining, or enjoying coastal breezes and peaceful salt pond views. The well-appointed kitchen features granite countertops and stainless steel appliances. Offered fully furnished, including kayaks, the home is ready for immediate enjoyment. Boating enthusiasts will appreciate the 12,000 lb. boat lift and quick access to Pine Channel and open water--ideal for fishing, diving, kayaking, and exploring the surrounding islands. With tranquil canal frontage, scenic views, privacy, and boating access from your own backyard, this property is perfectly suited as a full-time residence, seasonal retreat, or Florida Keys getaway.

29549 Forrestal Ave, Big Pine