Summerland Key, FL Homes

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  /49

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to the generous spacing between homes, as well as having

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 900-5290

  22865 Redfish Ln, Summerland Key, FL 33042
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• 

  

  

  /15

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • Apartment for Rent

  29420 Enterprise Ave Unit A, Big Pine Key, FL 33043

  Enjoy the best of Keys living in this beautifully renovated 2 bedroom, 2 bath upstairs unit in Big Pine Key. This spacious home offers stunning open water views and direct canal access perfect for boating enthusiasts, with room to dock your boat right outside.Inside, you'll find a modern feel with top-of-the-line appliances, a washer and dryer, and high-end finishes throughout. The open floor

  Halley Haack Coldwell Banker Schmitt RE Co.

  29420 Enterprise Ave Unit A, Big Pine Key, FL 33043
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  /40

  $1,115,000 Sold Sep 10, 2025

  • 988 Sq Ft
  • $1,129/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  28552 Maracaibo Rd, Little Torch Key, FL 33042

  This Waterfront 2-bedroom, 2-bathroom Keys Dream Home is designed with an open-concept layout to maximize space and views. The living area flows seamlessly into the dining and kitchen spaces, creating a perfect environment for entertaining guests. Large doors open onto an enclosed balcony allowing for stunning views of the canal. Large Garage! Enjoy the Florida sunshine by specially designed

  Teri Hiller Coldwell Banker Schmitt Real Estate Co.

  28552 Maracaibo Rd, Little Torch Key, FL 33042
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  /2

  Est $1,166,429 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft

  421 W Indies, Ramrod Key, FL 33042

  421 W Indies, Ramrod Key, FL 33042
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  /45

  $949,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  25057 7th St, Summerland Key, FL 33042

  Tropical Tranquility Meets Spacious Island Living.Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (786) 627-6100

  25057 7th St, Summerland Key, FL 33042
• 

  

  /12

  $5,900 per month

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • House for Rent

  27346 Martinique Ln, Summerland Key, FL 33042

  Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 4-bedroom, 2-bathroom waterfront home is a true island escape — where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

  Alicia Rufino Island Living Realty, LLC

  27346 Martinique Ln, Summerland Key, FL 33042
• 

  

  /46

  $998,000 Sold Sep 09, 2025

  • 1,318 Sq Ft
  • $757/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2013

  1117 Basque Ln, Cudjoe Key, FL 33042

  Tropical Oasis And Butterfly Haven With Absolutely Adorable Home on a canal with easy access to both the Ocean and Back Country. Large additional garden enhanced lot that would be a great location for a pool, and designed for the resident's privacy. The 3 bedroom 2 bath home has been updated with beautifully finished Custom Florida Cypress cabinets and Cambria Quartz center island in the

  Lynn Goodwin Coldwell Banker Schmitt Real Estate Co.

  1117 Basque Ln, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042
• 

  

  /48

  $1,319,000

  • 3 Beds
  • 3 Baths
  • 1,608 Sq Ft

  29457 Constitution Ave, Big Pine Key, FL 33043

  Solid, Spacious & Ready for Your Island Lifestyle! This 3 BD/3 BA concrete block home is just 3 houses in from Pine Channel, offering quick open water access and a short ride to Looe Key Reef, a world-famous spot for diving, snorkeling, and fishing. The 12,000 lb. boat lift is already installed and hard-wired for safety and convenience.Built Pre-FIRM, the home allows for renovation flexibility

  

  Nira Tocco

  Coldwell Banker Schmitt RE Co.

  (877) 806-2123

  29457 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /17

  $3,600 per month

  • 2 Beds
  • 1 Bath
  • 774 Sq Ft
  • Property for Rent

  29654 Constitution Ave, Big Pine Key, FL 33043

  Wonderful renovated waterfront 1/2 Duplex for rent! This one is the left side of duplex and has spacious 2 bedrooms and 1 full bath with open floor plan for living. Completely renovated and gorgeous inside! Beautiful Quartz countertops and stainless appliances in kitchen, all new fixtures and flooring thru-out. Stylish barn doors in both bedrooms with ample closet space. Screened in back porch

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  29654 Constitution Ave, Big Pine Key, FL 33043
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  /5

  $235,000 Sold Sep 09, 2025

  • Land

  • 212 Days On Market

  1388 Avenue B, Big Pine Key, FL 33043

  Welcome to the future home site at 1388 Avenue B in the sought-after Palm Villa neighborhood of Big Pine Key! This ROGO-exempt vacant lot offers a rare opportunity to build your dream home in paradise. Also listed with the current planned home for sale, MLS #612498. Either way, this property is your gateway to the tranquil lifestyle of the Florida Keys. Don't miss this versatile opportunity! Call

  Sarah Dolson Keller Williams Key West Compass Realty

  1388 Avenue B, Big Pine Key, FL 33043
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  /5

  Est $1,320,253 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,881 Sq Ft

  354 Airport Dr S, Summerland Key, FL 33042

  354 Airport Dr S, Summerland Key, FL 33042
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  /61

  $1,125,000

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  421 Ixora Dr, Big Pine Key, FL 33043

  Looking for great boating and a pool home that's already updated so you can spend time on the water? Look no further! This 2BD/3BA, CBS home is situated on a 50 ft. wide canal system that offers excellent access to the back country and Atlantic via Bogie Channel and Spanish Harbor. The 1120 sq. ft. living area has been completely renovated including the kitchen, bathrooms, impact-resistant

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 684-6607

  421 Ixora Dr, Big Pine Key, FL 33043
• 

  

  /19

  $3,900 per month

  • 3 Beds
  • 2 Baths
  • 1,048 Sq Ft
  • Property for Rent

  29267 Cypress Dr, Big Pine Key, FL 33043

  Located in the Eden Pines community, this unfurnished single-family home offers 2 bedrooms plus a bonus room previously used as a third bedroom. Enjoy canal-front living with a boat lift and plenty of storage, including an enclosed downstairs area and separate shed. Washer and dryer included. Pet-friendly with deposit. 6-8 month lease preferred. Utilities not included. Background and credit check

  Melissa Gibbins Expert Realty LLC (HQ)

  29267 Cypress Dr, Big Pine Key, FL 33043
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  /39

  $705,000 Sold Sep 08, 2025

  • 1,090 Sq Ft
  • $647/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  181 Doubloon Ln, Summerland Key, FL 33042

  This super cute 2 Bedroom 2 Bath home in Cutthroat Harbor Estates on Cudjoe Key offers easy ocean access with no bridges from the 60' long concrete dock. The open concept floorpan features a remodeled kitchen with center island, new cabinetry, stainless appliances and granite countertops. The enclosed Florida Room and adjacent outdoor Porch both overlook the water and are the perfect places to

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  181 Doubloon Ln, Summerland Key, FL 33042
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  /11

  Not Listed For Sale

  0 4th St Unit A&B 608914, Summerland Key, FL 33042

  0 4th St Unit A&B 608914, Summerland Key, FL 33042
• 

  

  /84

  $5,999,000

  • 4 Beds
  • 4 Baths
  • 4,315 Sq Ft

  4500 Filer Cove Rd, Summerland Key, FL 33042

  Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound located on Big Torch Key, a coastal community of large private estates located just 30 minutes outside of Key West. Driving down the gated 300' scenic driveway balmy breezes and tropical landscape lead you to the 4,315 sq. ft. open water residence. Once here you will enjoy world-class fishing and diving just

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-2623

  4500 Filer Cove Rd, Summerland Key, FL 33042
• 

  

  /25

  $3,650 per month

  • 3 Beds
  • 2 Baths
  • 1,285 Sq Ft
  • House for Rent

  3717 Palmetto St, Big Pine Key, FL 33043

  Nice remote 3/2 in the heart of big pine key with a canal in the back where you would be able to dock your boat; beautiful location, a relaxing getaway, close to the open water, less than an hour away from Key West, minutes away from shopping, schools, and park. Call Now. Background and Credit Report (we will provide you with a link, and your customer will pay for the fee), Proof of employment,

  George Assal ASLO Real Estate

  3717 Palmetto St, Big Pine Key, FL 33043
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  /37

  $510,000 Sold Sep 08, 2025

  • 972 Sq Ft
  • $525/SF
  • 97 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  30957 Mercedes Rd, Big Pine Key, FL 33043

  *** REDUCED - WHAT A BARGAIN! *** PEACEFUL and FENCED - Located in a quiet neighborhood on Big Pine Key, this well-maintained 3 bedroom, 2-bath home offers comfortable living both inside and out. Elevated - short stilts with current flood policy at $775/year.Enjoy the new stainless appliances and a metal roof was installed in 2018. Accordion shutters make it a breeze to button up. Just think,

  Donna Pezzi Keller Williams Key West Compass Realty

  30957 Mercedes Rd, Big Pine Key, FL 33043
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  /49

  Est $780,920 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  29765 Osprey Ln, Big Pine Key, FL 33043

  29765 Osprey Ln, Big Pine Key, FL 33043
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  /44

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  17094 Coral Dr, Summerland Key, FL 33042

  This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-7125

  17094 Coral Dr, Summerland Key, FL 33042
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  /65

  $6,995 per month

  • 4 Beds
  • 3 Baths
  • 3,116 Sq Ft
  • House for Rent

  30825 Ortega Ln, Big Pine Key, FL 33043

  Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quiet street,just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. This charminghome comes fully furnished and features an open-concept layout, modern updates, and coastal finishes throughout. relax on the coveredporch, entertain on the

  Walter Vargas Cervera Real Estate Inc.

  30825 Ortega Ln, Big Pine Key, FL 33043
• 

  

  /30

  $628,000 Sold Sep 05, 2025

  • 1,144 Sq Ft
  • $549/SF
  • 106 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  31256 Avenue H, Big Pine Key, FL 33043

  Welcome to your slice of paradise in Big Pine Key! This beautifully updated 3-bedroom, 2-bath home offers the perfect blend of modern comfort and laid-back Keys living. Partially furnished and move-in ready, this island retreat boasts impact windows and doors throughout for safety and peace of mind.Step inside to a bright and open living space with sleek finishes, coastal-inspired details, and a

  Karen Haack Coldwell Banker Schmitt RE Co.

  31256 Avenue H, Big Pine Key, FL 33043
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  /2

  Est $286,787 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042
• 

  

  /51

  $1,079,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  22841 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this angler's paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-8373

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /49

  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  3770 Park Ave, Big Pine Key, FL 33043

  Welcome to Caribbean Cove in Big Pine Key! This waterfront getaway is located in the National Key Deer Refuge, just 30 minutes away from Key West. This three-bedroom/two-bath home features an open floor plan, a fully furnished living area, and a modern, fully equipped kitchen. The kitchen is a culinary dream, featuring stainless steel appliances and an oversized quartz island, surrounded by eight

  Mary Jo Selden DomainRealty.com LLC

  3770 Park Ave, Big Pine Key, FL 33043
• 

  

  /47

  $1,150,000 Sold Sep 04, 2025

  • 864 Sq Ft
  • $1,331/SF
  • 135 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  1021 Caribbean Dr E, Summerland Key, FL 33042

  COASTAL RETREAT in desirable SUMMERLAND KEY COVE situated on a prime canal! Calling all BOATERS that seek deep draft flow-through water - you'll be to the Atlantic or Gulf in minutes. Slip away to your Keys retreat - move-in ready! You'll love the remodeled kitchen and baths so you can spend your time splashing in the pool or sipping a cool drink under the tiki. Completely furnished with

  Donna Pezzi Keller Williams Key West Compass Realty

  1021 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  Est $566,342 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  27188 Dolphin Rd, Ramrod Key, FL 33042

  27188 Dolphin Rd, Ramrod Key, FL 33042
• 

  

  /44

  $718,000

  • 2 Beds
  • 1 Bath
  • 1,497 Sq Ft

  30416 Coconut Hwy, Big Pine Key, FL 33043

  OVER ONE-HALF ACRE, lovingly cared for ... welcome to your sanctuary in the Keys! The large, fenced area of this 25,000 sq. ft. property provides wonderful privacy with a mature mango tree, starfruit tree, multiple banana plants, frangipanis, and ample space for planting a garden. Step inside the 1497 sq. ft. CBS home and you'll feel the old Keys charm mixed with the new. Your eyes are drawn to

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 646-1176

  30416 Coconut Hwy, Big Pine Key, FL 33043
• 

  

  /23

  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • House for Rent

  74 Pelican Ln Unit 1, Big Pine Key, FL 33043

  Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all nearby

  Yunior Molina My Realty Group, LLC.

  74 Pelican Ln Unit 1, Big Pine Key, FL 33043
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  /47

  $520,000 Sold Sep 04, 2025

  • 960 Sq Ft
  • $542/SF
  • 117 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  27853 Coral Shores Rd, Little Torch Key, FL 33042

  This move-in ready, canal-front home is the perfect Keys retreat! Offered fully furnished, it features 2 bedrooms, 2 bathrooms, and plenty of updates, including a new metal roof (2022), laminate flooring, 2023 kitchen appliances, and 2024 washer & dryer. The spacious back porch has fresh decking and screens, perfect for enjoying the ocean breeze. The 49' concrete seawall has room for multiple

  Leah Scarborough Island Welcome Real Estate

  27853 Coral Shores Rd, Little Torch Key, FL 33042
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  /14

  Not Listed For Sale

  12, 13, 14 Cook Island, Cook Island Key, FL 33043

  12, 13, 14 Cook Island, Cook Island Key, FL 33043
• 

  

  /13

  $475,000

  • 4 Beds
  • 3 Baths
  • 1,620 Sq Ft

  31052 Avenue H, Big Pine Key, FL 33043

  Investment opportunity on 10,000 sq. ft. double lot near the Big Pine Community Park; the location offers easy access to US1, local shopping and more; Marathon and Key West are within easy reach. **DO NOT WALK THE PROPERTY WITHOUT APPOINTMENT** 2 units, 2 tenants; pets on premises. 1,060 sq. ft. mobile home has 3BD/2BA, exterior wood siding; interior has been updated. CBS garage has 560 sq. ft.

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 542-1790

  31052 Avenue H, Big Pine Key, FL 33043
• 

  

  /14

  $4,550 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28543 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 9/30/25.Water view from balcony.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community

  Joseph Danieli AKT Realty LLC

  28543 Channel View Dr, Little Torch Key, FL 33042
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  /114

  $1,477,000 Sold Sep 02, 2025

  • 1,560 Sq Ft
  • $947/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  153 Galleon Ln, Summerland Key, FL 33042

  Welcome home to this beautifully maintained waterfront retreat in the heart of the Florida Keys! Located on the highly sought-after Cudjoe Key, this spacious & elegant home blends casual island living with refined comfort, all custom-designed & cared for with exceptional pride & attention to detail.From the moment you arrive, you'll notice the peaceful, private setting of this stunning tropical

  Lindsay Ryan EXP Realty LLC

  153 Galleon Ln, Summerland Key, FL 33042
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  /20

  Est $643,659 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft

  31342 Avenue I, Big Pine Key, FL 33043

  31342 Avenue I, Big Pine Key, FL 33043
• 

  

  /41

  $1,899,000

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  28573 Le Grand Rd, Little Torch Key, FL 33042

  This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 527-2862

  28573 Le Grand Rd, Little Torch Key, FL 33042
• 

  

  /9

  $13,500 per month

  • 4 Beds
  • 3 Baths
  • 2,855 Sq Ft
  • House for Rent

  28502 Channel View Dr, Little Torch Key, FL 33042

  This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

  Joseph Danieli AKT Realty LLC

  28502 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /49

  $689,000 Sold Aug 29, 2025

  • 1,410 Sq Ft
  • $489/SF
  • 48 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  156 Pelican Ln, Big Pine Key, FL 33043

  Discover your own tropical paradise at this beautifully updated 3-bedroom, 2-bath retreat nestled in the heart of Big Pine Key. Surrounded by lush landscaping and island breezes, this home is made for relaxing and reconnecting with nature.Soaring vaulted ceilings and impact-rated windows and doors create a bright, airy interior, while the metal roof adds peace of mind for coastal living. The

  Solaris Gregory Expert Realty LLC (HQ)

  156 Pelican Ln, Big Pine Key, FL 33043
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  /3

  Not Listed For Sale

  Vacant Lot Diane Rd, Big Pine Key, FL 33043

  Vacant Lot Diane Rd, Big Pine Key, FL 33043

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