Summerland Key, FL Homes

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  /26

  $779,000

  • 3 Beds
  • 3 Baths
  • 1,360 Sq Ft

  23930 Overseas Hwy, Summerland Key, FL 33042

  2 units for the price of one! What an amazing opportunity to buy in the Florida Keys market without breaking the bank. Live in one unit & rent the other.WATERFRONT duplex on Summerland Key just 25 minunets to Key West. Upper unit has 2B and 1Bath spacious living and dining space that opens onto a large deck overlooking the canal. Luxury vinyl floors, new lighting, new paint, new ceiling fans.

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (888) 431-6038

  23930 Overseas Hwy, Summerland Key, FL 33042
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  /61

  $1,636,000 Sold Aug 19, 2025

  • 1,260 Sq Ft
  • $1,298/SF
  • 6 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1982

  227 La Fitte Rd, Summerland Key, FL 33042

  The ONE you've been waiting for.. Blink & you'll miss this beauty! OPEN Waterfront w/ DEEP DRAFT- 60' dock, 15K lb boat lift, NEW POOL, CBS construction, Fully updated home located in coveted Jolly Rogers Estates on Little Torch Key. Unbeatable fishing, lobstering & diving from BOTH Ocean & Gulf at this PRIME location! ThurFlow covered dock on open water! This gorgeous home boasts 2 BR, 2 BA on

  Jennifer Chaney Chaney Homes

  227 La Fitte Rd, Summerland Key, FL 33042
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  /4

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
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  /48

  $3,499,000

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  653 Sawyer Dr, Summerland Key, FL 33042

  Spectacular Oceanfront Retreat with canal front dockage! Experience the ultimate in Keys living at this beautifully renovated 3 bedroom, 2 bath oceanfront oasis with an additional canal-front lot featuring boat dockage just across the street. This smart, solar-powered home with 6 Tesla Powerwalls, 2 EV chargers, plus an annual check for excess energy production offers eco-conscious luxury with

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 400-8268

  653 Sawyer Dr, Summerland Key, FL 33042
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  /22

  $650,000 Sold Aug 19, 2025

  • 888 Sq Ft
  • $732/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  27384 Saint Lucie Ln, Summerland Key, FL 33042

  Tucked away in Breezeswept Beach Estates, this charming 2-bedroom, 2-bath waterfront retreat offers easy access to both the Gulf and Atlantic--ideal for boaters and water lovers alike. Step inside to a bright, open-concept living space with soaring ceilings and lush tropical views from nearly every window and door. The spacious living and dining areas flow seamlessly into the kitchen and out

  Madeleine Lowe Expert Realty LLC (HQ)

  27384 Saint Lucie Ln, Summerland Key, FL 33042
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  /2

  Est $920,870 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  27434 Saint Lucie Ln, Ramrod Key, FL 33042
• 

  

  /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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  /58

  $760,000 Sold Aug 19, 2025

  • 848 Sq Ft
  • $896/SF
  • 66 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2021

  640 Carolyn Ave, Summerland Key, FL 33042

  640 Carolyn Avenue is a modern coastal retreat designed for comfort, privacy, and effortless outdoor living. Built-in 2021, this 4-year-old Affinity modular home blends high-quality construction with thoughtful design for the carefree lifestyle that defines island living.Set on an oversized canal-front lot with a 320 sq ft composite dock and fish cleaning station, this 2BD/2BA home invites you to

  Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
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  /2

  Est $2,230,173 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft

  305 S Point Dr, Summerland Key, FL 33042

  305 S Point Dr, Summerland 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
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  /25

  $500,000 Sold Aug 19, 2025

  • 1,020 Sq Ft
  • $490/SF
  • 265 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1974

  1620 Buttonwood Dr, Big Pine Key, FL 33043

  Nestled within the peaceful surroundings of the Key Deer Refuge, this charming 2 bedroom, 1 bathroom canal-front home offers a unique blend of nature, privacy, and easy access to water adventures. The home's inviting, light-filled interior embraces the essence of a classic Keys residence, with spacious, well-designed rooms. The open living area, filled with natural light from large windows,

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  1620 Buttonwood Dr, Big Pine Key, FL 33043
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  /2

  Est $1,308,212 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  22863 Bluegill Ln, Cudjoe Key, FL 33042
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  /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
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  /41

  $1,350,000 Sold Aug 18, 2025

  • 1,582 Sq Ft
  • $853/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  20735 5th Ave W, Summerland Key, FL 33042

  This beautifully renovated 3 Bedroom 2 Bathroom home is located in Cudjoe Gardens, a premiere boating community offering wide crystal clear deep draft canals, quick ocean access, neighborhood restaurant and a full service marina with fuel, bait, ice, refreshments and boat ramp. As you enter into this lovely and impeccably kept home a bright and sunny Great Room greets you highlighted with a

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20735 5th Ave W, Summerland Key, FL 33042
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  /3

  Est $266,500 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe 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
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  /34

  $1,300,000 Sold Aug 18, 2025

  • 2,100 Sq Ft
  • $619/SF
  • 214 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  22822 John Silver Ln, Summerland Key, FL 33042

  Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key

  Karen Haack Coldwell Banker Schmitt RE Co.

  22822 John Silver Ln, Summerland Key, FL 33042
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  /2

  Est $581,000 Not Listed For Sale

  • Studio

  0 E Ave Unit 604969, Big Pine Key, FL 33043

  0 E Ave Unit 604969, Big Pine Key, FL 33043
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  /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
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  /28

  $510,500 Sold Aug 14, 2025

  • 912 Sq Ft
  • $560/SF
  • 17 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1963

  31124 Avenue E, Big Pine Key, FL 33043

  Discover your slice of paradise in Big Pine Key! This charming 2-bedroom, 1-bathroom home offers an incredibly rare find: 20,000 square feet of lush, private property spanning two streets. Imagine unwinding in your expansive, fenced backyard on Avenue E, or enjoying the extra breathing room on the generous side yard on Avenue D. The property is a true tropical oasis, adorned with mature fruit

  Derrick Johnson Coco Plum Real Estate

  31124 Avenue E, Big Pine Key, FL 33043
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  /2

  Est $551,405 Not Listed For Sale

  • Studio
  • 1 Bath

  27418 Jamaica Ln, Ramrod Key, FL 33042

  27418 Jamaica Ln, Ramrod Key, FL 33042
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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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  /33

  $665,000 Sold Aug 14, 2025

  • 855 Sq Ft
  • $778/SF
  • 74 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  21161 Old State Road 4a, Summerland Key, FL 33042

  Island life awaits! Beautiful, elevated home boasts 2 spacious bedrooms and 2 recently renovated baths. Fenced yard with ample parking. Just off famous US1 this property is sited on a spacious lot with plenty of versatility! Zoning is Suburban Commercial (SC) which may allow for a Special Vacation Rental Permit. Perfect property for an owner occupier or investor. Wraparound porch offers sunrise

  Bascom Grooms Bascom Grooms Real Estate (KW)

  21161 Old State Road 4a, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, 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
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  /47

  $350,000 Sold Aug 14, 2025

  • 675 Sq Ft
  • $519/SF
  • 228 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1984

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

  Currently the LOWEST priced waterfront property in Venture Out! Seller says bring an offer! Welcome to a slice of paradise tucked away in the gated community of Venture Out on Cudjoe Key, where your dream of coastal living becomes a reality. This charming 2-bedroom, 1.5-bathroom home invites you to embrace the tropical lifestyle, offering the perfect blend of comfort and tranquility. The interior

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe 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
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  /44

  $853,000 Sold Aug 12, 2025

  • 1,081 Sq Ft
  • $789/SF
  • 123 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  873 Indies Rd, Summerland Key, FL 33042

  Spectacular double views from the rear screened patio offering canal views at a ''T'' junction and sunrise coming over the horizon. While sunset views from the front offer a full view over the estuary. Don't miss some beautiful glimpses of nature as migrating birds and fish nurseries fill the estuary. The well-appointed home offers 3 bedrooms and 2 bathrooms with double sliding glass doors onto

  Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  0 Crane Blvd, Sugarloaf Key, FL 33042

  0 Crane Blvd, Sugarloaf Key, FL 33042
• 

  

  /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
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  /14

  $1,250,000 Sold Aug 11, 2025

  • 1,400 Sq Ft
  • $893/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  365 Pirates Rd, Summerland Key, FL 33042

  Beautifully maintained 3BR/2BA concrete home with new addition featuring vaulted ceilings and modern finishes. Solid concrete construction, metal roof, and impact-rated windows and doors provide outstanding storm protection and peace of mind. All new appliances throughout.Custom-built pool with silver travertine deck, surrounded by lush landscaping and a variety of unique palms, creating a

  Christopher Tanaka Coldwell Banker Schmitt RE Co.

  365 Pirates Rd, Summerland Key, FL 33042
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  /2

  Est $861,822 Not Listed For Sale

  • Studio

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042
• 

  

  /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
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  /34

  $695,000 Sold Aug 05, 2025

  • 1,233 Sq Ft
  • $564/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1959

  1555 Watson Blvd, Big Pine Key, FL 33043

  Welcome to your slice of paradise in Big Pine Key! This solid concrete 2-bedroom, 2-bathroom home is perfectly positioned on a wide canal with direct access and a short boat ride to open water, making it a boater's dream.Step inside to an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas -- ideal for entertaining or simply enjoying the Keys lifestyle. Natural

  Terrance Sullivan Ocean Sotheby's International Realty

  1555 Watson Blvd, Big Pine Key, FL 33043
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  /2

  Est $507,080 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  390 W Indies Dr, Ramrod Key, FL 33042

  390 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /18

  $750,000

  • Land

  27941 Porgie Path, Summerland Key, FL 33042

  Located on Little Torch Key, this ROGO EXEMPT 6,221 sq. ft. lot boasts spectacular stunning sunset views over the gulf. Fantastic Gulf access from the back yard boat ramp allowing easy access to get out on the water, whether you're heading out for a day of fishing or a sunset kayak and paddle board tour. This Little Torch Key property offers stunning Gulf side sunset views and a prime location

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 745-7897

  27941 Porgie Path, Summerland Key, FL 33042
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  /42

  $615,000 Sold Aug 05, 2025

  • 864 Sq Ft
  • $712/SF
  • 132 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1985

  3231 Pompano St, Big Pine Key, FL 33043

  Ultimate Privacy in Big Pine KeyStep into an extraordinary sanctuary of seclusion, where tropical elegance meets unmatched exclusivity. 1 of only 2 homes in the entire Seaview subdivision of Big Pine Key.3231 Pompano Drive is a beautifully renovated island retreat set on a 10,000 sq. ft. lot, surrounded by untouched nature and abundant wildlife. No additional homes can ever be built, ensuring

  Dawn McComish Lokation Real Estate

  3231 Pompano St, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 936 Sq Ft

  31255 Avenue G, Big Pine Key, FL 33043

  31255 Avenue G, Big Pine Key, FL 33043
• 

  

  /47

  $1,165,000

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  29051 Magnolia Ln, Big Pine Key, FL 33043

  Welcome to 29051 Magnolia Ln, Big Pine Key, FL! This home offers a 2-bedroom, 2-bath main area and a pre-FIRM permitted 480 sq. ft. studio/MIL suite with a full bath. Nestled on a 5,100 sq. ft. lot, this concrete home is ideal for island living. The chef's kitchen features stainless steel appliances, premium counters, and breakfast bar. Enjoy a screened porch overlooking the canal, complete with

  

  Yvette Toledo-Baste

  Compass Florida, LLC

  (866) 971-5749

  29051 Magnolia Ln, Big Pine Key, FL 33043

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