Summerland Key, FL Homes

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  /19

  Not Listed For Sale

  31008 Avenue B, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 684 Sq Ft
  • Built 1973

  31008 Avenue B, Big Pine Key, FL 33043

  Last Sold Summary

  • $490/SF
  • 264 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
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  /50

  $1,385,000

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  30830 Palm Dr, Big Pine Key, FL 33043

  Discover the perfect Florida Keys waterfront retreat in Big Pine Key. Situated on an oversized 16,779 sq ft lot on a quiet street away from the highway, this solidly built concrete block home with a concrete subfloor and stucco finish offers durability, privacy, and the laid-back island lifestyle buyers dream about.Boaters will appreciate 112 feet of concrete seawall, a 10,000 lb boat lift, and

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (855) 640-6438

  30830 Palm Dr, Big Pine Key, FL 33043
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  /43

  $1,025,000 Sold Feb 11, 2026

  29039 Cedar Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $971/SF
  • 42 Days On Market

  Current Estimated Value $999,994

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

  29039 Cedar Dr, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • $551/SF

  Last Sold Price $450,000
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  /43

  $888,000

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

  25057 7th St, Summerland Key, FL 33042

  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 added bonus of a natural windbreak and guaranteed

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (786) 869-2251

  25057 7th St, Summerland Key, FL 33042
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  /35

  $817,500 Sold Dec 01, 2025

  22878 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $862/SF
  • 133 Days On Market

  Current Estimated Value $811,981

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
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  /5

  Est $1,346,232 Not Listed For Sale

  354 Airport Dr S, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,881 Sq Ft
  • Built 2013

  354 Airport Dr S, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Below List Price
  • $744/SF
  • 2 Days On Market

  Last Sold Price $1,400,000

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
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  /31

  $725,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  27448 Haiti Ln, Ramrod Key, FL 33042

  Claim your slice of paradise and build the waterfront setup you've always wanted. Welcome to 27438 Haiti Ln, a deep-water canal-front blank canvas on Ramrod Key designed for the serious angler. This isn't just a home; it's the ultimate staging ground for your offshore and backcountry adventures.The highlight? A pristine shoreline ready for you to design and permit your dream dock. Whether you

  

  Brenda Thomas

  Island Welcome Real Estate

  (645) 225-2680

  27448 Haiti Ln, Ramrod Key, FL 33042
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  /83

  $3,300,000 Sold Jul 11, 2025

  16705 Tamarind Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 3,086 Sq Ft
  • Built 2015

  Last Sold Summary

  • 27% Below List Price
  • $1,069/SF
  • 299 Days On Market

  Current Estimated Value $3,406,516

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  16705 Tamarind Rd, 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

  Last Sold Summary

  • 53 Days On Market

  Last Sold Price $645,000

  Last Listing Agent Jenna Stauffer Ocean Sotheby's International Realty
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  /30

  $975,000

  • 3 Beds
  • 3 Baths
  • 1,492 Sq Ft

  31490 Avenue F, Big Pine Key, FL 33043

  This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and functionality. Featuring impact windows and doors and a durable metal roof, this home provides peace of mind and protection for years to come. The open-concept living area is perfect for both relaxation and entertaining, with a modern kitchen boasting quartz countertops and stainless steel appliances. The

  

  Austin Kimbler

  Expert Realty LLC (HQ)

  (833) 691-1620

  31490 Avenue F, Big Pine Key, FL 33043
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  /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 Coldwell Banker - Ft. Lauderdale

  0 Asturias Rd, Cudjoe Key, FL 33042
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  Est $649,961 Not Listed For Sale

  30361 Harding Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 888 Sq Ft
  • Built 1963

  30361 Harding Rd, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Above List Price
  • $709/SF
  • 295 Days On Market

  Last Sold Price $630,000

  Last Listing Agent David Kaufmann Century 21 Circle
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  /22

  $714,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  4039 Egret Ln, Summerland Key, FL 33042

  Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 238-9391

  4039 Egret Ln, Summerland Key, FL 33042
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  /2

  $600,000 Sold Jul 14, 2025

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1993

  Last Sold Summary

  • 14% Below List Price
  • $735/SF
  • 56 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
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  /49

  Est $780,116 Not Listed For Sale

  29765 Osprey Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 1,456 Sq Ft
  • Built 1988

  29765 Osprey Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 8% Above List Price
  • $498/SF
  • 52 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)
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  /44

  $1,199,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  30329 Heron Ln, Big Pine Key, FL 33043

  Nature Lover's Waterfront Retreat on a Rare Double Canal Lot. Imagine living where the sky blazes with sunsets over a pristine bird sanctuary and gentle Key Deer roam freely through your yard. Welcome to 30329 Heron Lane, a beautifully maintained 3 bedroom, 2 bathroom elevated Conch Cottage perched on a 15,438 sq ft double corner canal lot with 268' of waterfront in Big Pine Key. From the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (866) 665-8962

  30329 Heron Ln, Big Pine Key, FL 33043
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  /37

  $642,000 Sold Jul 11, 2025

  31067 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $423/SF
  • 9 Days On Market

  Current Estimated Value $669,005

  Last Listing Agent Jared Chiagouris Truman & Co. (KW)

  31067 Avenue C, Big Pine Key, FL 33043
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  /2

  Est $251,086 Not Listed For Sale

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

  • Studio
  • Built 1981

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

  Last Sold Summary

  • 5% Below List Price

  Last Sold Price $265,000
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  /39

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  51 Drost Dr, Summerland Key, FL 33042

  Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 551-4933

  51 Drost Dr, Summerland Key, FL 33042
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  /2

  $49,000 Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  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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  /2

  Est $690,340 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

  Last Sold Summary

  • 19% Below List Price
  • $471/SF

  Last Sold Price $580,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /43

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  51 Sawyer Dr, Summerland Key, FL 33042

  Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (844) 970-3222

  51 Sawyer Dr, Summerland Key, FL 33042
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  /3

  $420,000 Sold Jun 27, 2025

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 488 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Below List Price
  • $861/SF
  • 0 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
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  /3

  Not Listed For Sale

  27732 Astrangia Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1985

  27732 Astrangia Ave, Little Torch Key, FL 33042

  Last Sold Summary

  • $504/SF
  • 275 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Roger Cousineau Keller Williams Key West Compass Realty
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  /42

  $815,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  29183 Cedar Dr, Big Pine Key, FL 33043

  This terrific canal-front home is situated on a fenced, low-maintenance 5,000 sq. ft. lot with 50 ft. concrete seawall and boat lift. The 50 ft. wide canal provides excellent access to the ocean and back-country with only one neighborhood bridge to go under (approx.. 10.5 ft. clearance.) Well-maintained and enjoyed by the owner for many years, it offers Hardi-board siding upstairs, a great

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 382-4166

  29183 Cedar Dr, Big Pine Key, FL 33043
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  $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
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  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 Sold Price $135,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
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  /74

  $2,999,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  17041 Marlin Dr, Summerland Key, FL 33042

  Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (305) 809-8894

  17041 Marlin Dr, Summerland Key, FL 33042
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  /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 $848,119

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
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  /20

  Est $625,972 Not Listed For Sale

  31342 Avenue I, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft
  • Built 2021

  31342 Avenue I, Big Pine Key, FL 33043

  Last Sold Summary

  • 2% Below List Price
  • $1,159/SF
  • 40 Days On Market

  Last Sold Price $640,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /50

  $1,600,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  947 Gulf Dr, Summerland Key, FL 33042

  There's a certain feeling you get the moment you pull onto Summerland Cove Isle, quiet, breezy, and unmistakably upscale. The kind of street where every home has been cared for, every canal sparkles, and the water itself seems to move with purpose. This home sits on the most coveted stretch of the island, where the flow-through, crystal-clear, extra-deep canals are the heartbeat of the

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 983-9115

  947 Gulf Dr, Summerland Key, FL 33042
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  /68

  $950,000 Sold Apr 11, 2025

  31670 Avenue C, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 4% Below List Price
  • $774/SF
  • 28 Days On Market

  Current Estimated Value $957,025

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

  31670 Avenue C, 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 Sold Price $55,000

  Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.
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  $285,000

  • Land

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 876-6382

  Unlisted Address
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  /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 $2,060,214

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
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  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

  • $553/SF
  • 44 Days On Market

  Last Sold Price $560,000

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)
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  /50

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  21250 Conch Dr, Summerland Key, FL 33042

  Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 614-3802

  21250 Conch Dr, Summerland Key, FL 33042
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  $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 $1,091,395

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

  22946 Bluegill Ln, Summerland Key, FL 33042
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  Est $879,787 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

  Last Sold Summary

  • 1% Below List Price
  • $765/SF

  Last Sold Price $875,000

  Last Listing Agent Tracey Stevens Gardiner Realty ONE Group Destination

Showing Results 121 - 160, Page 4 of 18