Summerland Key, FL Homes

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  /49

  $849,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  22832 John Silver Ln, Summerland Key, FL 33042

  CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES.Situated on over 6,000 Square Feet on a deep water canal - this recently updated property provides easy boating access to both the Gulf and the Atlantic, making it a perfect home base for world class fishing, diving, SANDBARS and enjoying the keys lifestyle.New Upgrades Include -Fully remodeled

  

  Mike Kane

  Internet Realty of the Florida Keys

  22832 John Silver Ln, Summerland Key, FL 33042
• 

  

  

  /3

  $75,000

  Sold Oct 10, 2025

  0 Asturias Rd, Cudjoe Key, FL 33042

  • Land
  • 1.01 Acres
  • $74,124 per Acre

  Last Sold Summary

  • 62% Below List Price
  • 41 Days On Market

  Last Listing Agent Maryann Warren Prudential Keyswide Properties

  0 Asturias Rd, Cudjoe Key, FL 33042
• 

  

  /2

  Est $701,159

  Not Listed For Sale

  27188 Dolphin Rd, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1991

  27188 Dolphin Rd, Ramrod Key, FL 33042
• 

  

  

  /43

  $1,850,000

  $151K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,980 Sq Ft

  1607 Sunrise Dr, Big Pine Key, FL 33043

  Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  1607 Sunrise Dr, Big Pine Key, FL 33043
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  /42

  $1,065,000

  Sold Jun 22, 2026

  27345 Barbuda Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $807/SF
  • 18 Days On Market

  Last Listing Agent Madeleine Young Island Welcome Real Estate LLC

  27345 Barbuda Ln, Summerland Key, FL 33042
• 

  

  /68

  Est $963,331

  Not Listed For Sale

  31670 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 1.5 Baths
  • 1,227 Sq Ft
  • Built 1956

  31670 Avenue C, Big Pine Key, FL 33043

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.
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  /39

  $485,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home withFlorida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.*

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
• 

  

  /32

  $3,500

  Sold May 20, 2026

  29850 Journeys End Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1988

  Last Sold Summary

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

  Current Estimated Value $1,289,717

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  29850 Journeys End Rd, Big Pine Key, FL 33043
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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

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
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  /145

  $16,900,000

  • 5 Beds
  • 4 Baths
  • 3,352 Sq Ft

  0 Howell Key Unit 620413, Summerland Key, FL 33042

  Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled opportunity to own an off-grid luxury island with two building rights, allowing for one additional residence, surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  0 Howell Key Unit 620413, Summerland Key, FL 33042
• 

  /2

  $49,000

  Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land
  • 5,499 Sq Ft
  • $388,080 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
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  /8

  Not Listed For Sale

  0000 Dorn Rd, Big Torch Key, FL 33042

  0000 Dorn Rd, Big Torch Key, FL 33042

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Lindsay Ryan EXP Realty LLC
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  /37

  $700,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  29160 Primrose Ln, Big Pine Key, FL 33043

  Welcome to Eden Pines--now offered at an exceptional new price of $700,000! This charming 3-bedroom, 2-bath home sits on a spacious and private 10,000 sq. ft. lot in the heart of Big Pine Key. With a garage, abundant storage, a fully fenced yard, and room to add a pool, this property offers endless potential.Inside, you'll find an inviting open-concept floor plan, two beautifully updated

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  29160 Primrose Ln, Big Pine Key, FL 33043
• 

  

  /40

  $790,000

  Sold Jul 02, 2026

  3686 Gulfstream St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $611/SF
  • 56 Days On Market

  Current Estimated Value $793,138

  Last Listing Agent Gidget Jackson RE/MAX Realty Group

  3686 Gulfstream St, 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

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.
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  /33

  $599,000

  Pre-Foreclosure

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  30354 Palm Dr, Big Pine Key, FL 33043

  Private Lower Keys opportunity! Nestled behind a lush hedge of mature Areca palms, this 2BR/2BA CBS home offers privacy, solid construction, and endless potential. Recent improvements include a 2018 post-Irma roof and storm shutters. The fully fenced 6,250 sq. ft. lot provides ample space for a pool, outdoor living, or tropical gardens, with a storage shed already in place. Enjoy a peaceful

  

  Coby Taylor

  Expert Realty LLC (HQ)

  30354 Palm Dr, Big Pine Key, FL 33043
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  /61

  $2,675,000

  Sold Jun 01, 2026

  20844 4th Ave W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Below List Price
  • $906/SF
  • 10 Days On Market

  Current Estimated Value $2,666,734

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, Summerland Key, FL 33042
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  /34

  Not Listed For Sale

  27772 Astrangia Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1978

  27772 Astrangia Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)
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  /97

  $1,199,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,522 Sq Ft

  17151 Marlin Dr, Sugarloaf Key, FL 33042

  This beautifully remodeled waterfront bungalow is nestled in the heart of Sugarloaf Shores ,one of the Lower Florida Keys' most desirable boating communities. Set on an expansive 12,500 sq ft lot surrounded by lush tropical landscaping, this elevated two-story home offers the perfect blend of privacy, comfort, and island charm. With 3 Bedrooms plus a Loft and 2 Bathrooms, the layout is

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  17151 Marlin Dr, Sugarloaf Key, FL 33042
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  /38

  $840,000

  Sold Sep 30, 2025

  3611 S Seas St, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $787/SF
  • 183 Days On Market

  Last Listing Agent Scott Brisson KeyIsle Realty

  3611 S Seas St, Big Pine Key, FL 33043
• 

  /2

  Est $1,227,400

  Not Listed For Sale

  1581 State Rd Unit 4A, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2007

  1581 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /19

  $199,000

  $16K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $3,980,000 per Acre

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
• 

  

  /43

  $1,100,000

  Sold May 14, 2026

  1011 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $962/SF
  • 0 Days On Market

  Current Estimated Value $1,102,076

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1011 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040
• 

  

  /71

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

  Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile homenestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
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  /70

  $1,290,000

  Sold May 19, 2026

  403 Indies Rd, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1991

  Last Sold Summary

  • 4% Below List Price
  • $960/SF
  • 63 Days On Market

  Current Estimated Value $1,288,115

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /14

  Est $377,737

  Not Listed For Sale

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  • 3 Beds
  • Built 1943

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Shannon Butler Key Colony Beach Realty
• 

  

  /32

  $1,899,000

  $301K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,800 Sq Ft

  3256 Catherine St, Summerland Key, FL 33042

  Tucked away on Big Torch Key, this CBS-constructed waterfront home offers a quiet, private setting with beautiful open-water views and remarkable year-round sunsets. Surrounded by the natural beauty of the Lower Keys, Key deer are often seen nearby, while backcountry boating and flats fishing are just minutes away. Boaters will appreciate convenient access to both Gulf and Atlantic

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  3256 Catherine St, Summerland Key, FL 33042
• 

  

  /75

  $830,000

  Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $864,164

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  /2

  Est $511,642

  Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042
• 

  

  /54

  $675,000

  • 4 Beds
  • 2 Baths
  • 1,566 Sq Ft

  31011 Avenue C, Big Pine Key, FL 33043

  This 4-bedroom, 2-bath, 1566 sq. ft. home has so much to offer for the price! A spacious living area separates the primary bedroom and ensuite bath from the remaining bedrooms and bath. Features include tile floors throughout, a separate laundry room, a big sundeck and a ground-level storage enclosure. Covered parking is conveniently accessed from either Avenue C or Sands Rd. The 5,000 sq. ft.

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  31011 Avenue C, Big Pine Key, FL 33043
• 

  

  /50

  $1,900,000

  Sold Mar 27, 2026

  711 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $950/SF
  • 62 Days On Market

  Current Estimated Value $1,762,568

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
• 

  

  /48

  $775,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft

  4016 Dorn Rd, Summerland Key, FL 33042

  Escape to the Lower Keys with this peaceful Big Torch Key retreat overlooking protected lands. Enjoy convenient boating access to both the Gulf and Atlantic via Niles Channel, then return to your 60 ft. concrete dock after a day of fishing or diving. This well-maintained, fully furnished 3-bedroom, 2-bath home is move-in ready, with sewer and FKAA 'city' water service, plus a cistern beneath the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  4016 Dorn Rd, Summerland Key, FL 33042
• 

  

  /26

  $610,000

  Sold Apr 03, 2026

  29030 Iris Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft
  • Built 1974

  Last Sold Summary

  • 15% Below List Price
  • $451/SF
  • 449 Days On Market

  Current Estimated Value $624,180

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  29030 Iris Dr, Big Pine Key, FL 33043
• 

  /2

  Est $779,974

  Not Listed For Sale

  53 Treasure Chest Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1991

  53 Treasure Chest Dr, Cudjoe Key, FL 33042
• 

  

  /43

  $725,000

  $24K PRICE DROP Under Contract

  • 2 Beds
  • 3 Baths
  • 1,152 Sq Ft

  28316 County Rd, Summerland Key, FL 33042

  *Back-up offers welcome.* Are you looking for a canal-front home that could use your TLC? Situated on a 9,375 sq. ft. fenced lot, this 2-bedroom, 3-bath CBS opportunity is about mid-way between the convenient 4A Boat Ramp to the west and Pine Channel to the east. Bright and airy, the extra-large kitchen was updated with new cabinets, stainless steel appliances and quartz counters in recent years.

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  28316 County Rd, Summerland Key, FL 33042
• 

  

  /41

  $1,105,000

  Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,125,577

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  /2

  Est $199,913

  Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042
• 

  

  /55

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  29038 Violet Dr, Big Pine Key, FL 33043

  This home has a little bit of everything! Tucked away toward the end of the street in Eden Pines, this 3/2, low maintenance property has a lot to offer. Upstairs is easy living with tile floors, a beautiful wood ceiling, and a large screened porch off the living area. The home is situated on a larger lot, with it's own boat slip, concrete seawall, and different 'pocket' areas to relax in. There

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  29038 Violet Dr, Big Pine Key, FL 33043

Showing Results 161 - 200, Page 5 of 18