Summerland Key, FL Homes

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  /31

  $749,500

  • 3 Beds
  • 1 Bath
  • 1,562 Sq Ft

  360 W Shore Dr, Summerland Key, FL 33042

  Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 949-3594

  360 W Shore Dr, Summerland Key, FL 33042
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  /13

  $4,350 per month

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Property for Rent

  2635 Koehns Ave, Big Pine Key, FL 33043

  Discover this charming 3-bedroom, 2-bathroom furnished home. ALL UTILITIES ARE INCLUDED. The spacious, open floor plan features a gourmet kitchen with white quartz countertops and sleek, stainless-steel Bertazzoni appliances imported from Italy.Relax in the dining area, overlooking a screened-in patio with stunning views of the heated saltwater pool. The lush backyard is a tropical paradise,

  

  Karen Liskey

  Key Colony Beach Realty

  (866) 729-5076

  2635 Koehns Ave, Big Pine Key, FL 33043
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  /27

  $837,000 Sold Jul 11, 2025

  27417 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $771/SF
  • 274 Days On Market

  Current Estimated Value $849,106

  Last Listing Agent Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  27417 Cayman Ln, Summerland Key, FL 33042
• 

  

  

  /18

  Est $746,279 Not Listed For Sale

  27438 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1987

  27438 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $904/SF
  • 146 Days On Market

  Last Sold Price $738,000

  Last Listing Agent Caroline Bauer Key West Sales, LLC
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  /49

  $799,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  1672 Pandorea Ln, Big Pine Key, FL 33043

  Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, an exceptional upgraded

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 410-2419

  1672 Pandorea Ln, Big Pine Key, FL 33043
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  /70

  $12,500 per month

  • 4 Beds
  • 4 Baths
  • 2,952 Sq Ft
  • Property for Rent

  21640 Overseas Hwy, Summerland Key, FL 33042

  Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 442-3255

  21640 Overseas Hwy, Summerland Key, FL 33042
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  /60

  $950,000 Sold Oct 17, 2025

  76 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,028 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $924/SF
  • 369 Days On Market

  Current Estimated Value $941,667

  Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

  76 W Shore Dr, Summerland Key, FL 33042
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  /21

  Est $449,669 Not Listed For Sale

  28194 Gulf Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1983

  28194 Gulf Blvd, Big Pine Key, FL 33043

  Last Sold Summary

  • 25% Above List Price
  • $321/SF
  • 11 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Cliff Glansen FlatFee.com
• 

  

  /43

  $763,000

  • 4 Beds
  • 2 Baths
  • 2,136 Sq Ft

  30374 Oleander Blvd, Big Pine Key, FL 33043

  If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 827-7154

  30374 Oleander Blvd, Big Pine Key, FL 33043
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  /12

  $2,500 per month

  Coco Palms

  2 Beds

  21585 Overseas Hwy, Cudjoe Key, FL 33042

  Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

  21585 Overseas Hwy, Cudjoe Key, FL 33042
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  /56

  $1,725,000 Sold Jul 11, 2025

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $1,039/SF
  • 258 Days On Market

  Current Estimated Value $1,676,709

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17159 Amberjack Ln, Summerland Key, FL 33042
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  /63

  Est $1,923,826 Not Listed For Sale

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,366 Sq Ft
  • Built 2015

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $835/SF
  • 190 Days On Market

  Last Sold Price $1,975,000

  Last Listing Agent Lisa Swanson The Agency Florida Keys
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  /35

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  27940 Lobster Tail Trail, Summerland Key, FL 33042

  Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $625,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 218-8749

  27940 Lobster Tail Trail, Summerland Key, FL 33042
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  /41

  $7,500 per month

  • 3 Beds
  • 2 Baths
  • 6,098 Sq Ft
  • House for Rent

  280 Airport Dr S, Summerland Key, FL 33042

  *** Private Airstrip *** Welcome to your slice of paradise in the Florida Keys! For aviation enthusiasts, the allure of this property is further enhanced by its location within a private airpark community (FD51 Summerland Key Airport). Nestled on a serene, clear wide canal with direct access to the Atlantic Ocean with no bridges, within a private airpark community, this home offers the

  Lisa Guirguis Genesis Realty Team

  280 Airport Dr S, Summerland Key, FL 33042
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  /45

  $1,550,000 Sold Jan 30, 2026

  28538 John Silver Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $1,242/SF
  • 164 Days On Market

  Current Estimated Value $1,511,933

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28538 John Silver Rd, Summerland Key, FL 33042
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  /9

  Not Listed For Sale

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Last Sold Summary

  • $24/SF

  Last Sold Price $300,000

  Last Listing Agent Jana Alarid Coldwell Banker Realty
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  /44

  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  937 Gulf Dr, Summerland Key, FL 33042

  High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout,

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 230-1994

  937 Gulf Dr, Summerland Key, FL 33042
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  /20

  $5,357 - $15,000 per month

  Little Torch Cottages

  2 - 4 Beds

  28501 Channel View Dr, Little Torch Key, FL 33042

  In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

  28501 Channel View Dr, Little Torch Key, FL 33042
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  /45

  $630,000 Sold Dec 08, 2025

  22970 Sharp Ln, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $1,094/SF
  • 4 Days On Market

  Current Estimated Value $662,671

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  22970 Sharp Ln, Summerland Key, FL 33042
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  /14

  Not Listed For Sale

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 6,725 Sq Ft
  • Built 1975

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  Last Sold Summary

  • $37/SF
  • 7 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
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  /34

  $1,575,000

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

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! 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

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 241-6029

  22865 Redfish Ln, Summerland Key, FL 33042
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  /30

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft
  • House for Rent

  30259 Palm Dr, Big Pine Key, FL 33043

  A light and bright stilted home in a wooded subdivision on Big Pine. Large, screened walk-around patio, chair lift, impact windows, updated granite kitchen, SS appliances, upgraded baths, washer/dryer, outdoor shower, carport parking w/motion lights, large, landscaped yard, paver drive, ceiling fans, central AC/heat, water/lawn care included. Tenant pays electric and cable/internet. Application

  Paul Rogers Coldwell Banker Schmitt RE Co.

  30259 Palm Dr, Big Pine Key, FL 33043
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  /35

  $1,499,900 Sold May 27, 2025

  1082 Bay Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 1980

  Last Sold Summary

  • 25% Below List Price
  • $1,042/SF
  • 602 Days On Market

  Current Estimated Value $1,747,013

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1082 Bay Dr, Summerland Key, FL 33042
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  /29

  Not Listed For Sale

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2001

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  Last Sold Summary

  • $966/SF
  • 14 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Susan Rich Select Properties of NWFL
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  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Summerland Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 853-7147

  153 Peg Leg Ln, Summerland Key, FL 33042
• 

  

  /20

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • House for Rent

  29822 Frostproof Rd, Big Pine Key, FL 33043

  Property Id: 2218567Enjoy comfort and privacy in this elevated 3-bedroom, 2-bath home, open floor plan and vaulted ceilings lots of windows and french doors. Furnished except for the smallest room. Make it your office or hobby room or guest room. The living room and master bedroom each open through French doors onto a balcony, Relax or entertain outdoors on the balcony/patio, and enjoy

  29822 Frostproof Rd, Big Pine Key, FL 33043
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  /60

  $930,000 Sold Jan 23, 2026

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Below List Price
  • $722/SF
  • 51 Days On Market

  Current Estimated Value $926,331

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
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  /15

  Not Listed For Sale

  8 Calico Jack Circle Cir, Verifying, FL 33042

  8 Calico Jack Circle Cir, Verifying, FL 33042

  Last Sold Summary

  • 18 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY
• 

  

  /43

  $924,000

  • 3 Beds
  • 2 Baths
  • 1,036 Sq Ft

  420 W Indies Dr, Summerland Key, FL 33042

  Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 666-1028

  420 W Indies Dr, Summerland Key, FL 33042
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  /19

  $4,900 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 2-bedroom, 1-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
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  /2

  $510,000 Sold Sep 08, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 972 Sq Ft
  • Built 1989

  Last Sold Summary

  • $525/SF

  Current Estimated Value $511,674

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  Unlisted Address
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  /40

  Not Listed For Sale

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1996

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  Last Sold Summary

  • $674/SF
  • 22 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Ian Calderwood Bluescape Real Estate
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  /72

  $2,995,000

  • 4 Beds
  • 3 Baths
  • 2,913 Sq Ft

  20920 5th Ave W, Summerland Key, FL 33042

  Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens--a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

  

  Miriam Novotny

  Compass Florida, LLC

  (786) 667-5744

  20920 5th Ave W, Summerland Key, FL 33042
• 

  

  /16

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • House for Rent

  30612 23rd Ln, Big Pine Key, FL 33043

  Property Id: 2240886Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy,

  30612 23rd Ln, Big Pine Key, FL 33043
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  /73

  $2,925,000 Sold Jun 10, 2025

  17018 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1991

  Last Sold Summary

  • 25% Below List Price
  • $1,987/SF
  • 122 Days On Market

  Current Estimated Value $2,936,647

  Last Listing Agent Coby Taylor Taylor & Assoc. RE, Inc.

  17018 Wahoo Ln, Summerland Key, FL 33042
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  /37

  Not Listed For Sale

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • $750/SF
  • 9 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)
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  /45

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  195 W Shore Dr, Summerland Key, FL 33042

  Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 998-8438

  195 W Shore Dr, Summerland Key, FL 33042
• 

  

  /16

  $5,357 per month

  • 2 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • House for Rent

  53 Barry Ave, Summerland Key, FL 33042

  This is a 2 story furnished or unfurnished single family house with a private pool, fenced in yard, screened patio, 2 bedrooms, 2 bathrooms with showers, stainless steel appliances, hurricane windows, washer and dryer, tile and wood floors. You are also able to use the amenities at our property next door such as 24 hour community gym and sauna. marina with boat ramp, outdoor games, bbq, kayaks

  Joseph Danieli AKT Realty LLC

  53 Barry Ave, Summerland Key, FL 33042
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  /8

  $906,300 Sold Apr 30, 2025

  0000 Dorn Rd, Big Torch Key, FL 33042

  • Land
  • 35.5 Acres
  • $25,530 per Acre

  Last Sold Summary

  • 43% Below List Price
  • 103 Days On Market

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  0000 Dorn Rd, Big Torch Key, FL 33042
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  /64

  Not Listed For Sale

  15 W Cooks, Cook Island Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,551 Sq Ft
  • Built 1977

  15 W Cooks, Cook Island Key, FL 33043

  Last Sold Summary

  • $1,070/SF
  • 16 Days On Market

  Last Sold Price $1,660,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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