Summerland Key, FL Homes

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  /66

  $539,000

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /61

  $1,750,000 Sold Mar 09, 2026

  876 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $1,493/SF
  • 122 Days On Market

  Current Estimated Value $1,614,886

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  Last Sold Summary

  Last Sold Price $70,000

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)
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  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
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  /57

  $1,375,000 Sold Apr 17, 2025

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  Last Sold Summary

  • 19% Below List Price
  • $765/SF
  • 215 Days On Market

  Current Estimated Value $1,387,846

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
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  /14

  Est $514,755 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

  • 129% Above List Price
  • $248/SF
  • 119 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Shannon Butler Key Colony Beach Realty
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  /62

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  28151 Helen Ave, Summerland Key, FL 33042

  Like new extra spacious open floor plan with efficient layout, ultra low insurances, and free public boat ramp nearby! This home features three large bedrooms and two full bathrooms with tiled showers, a huge eat-in stainless steel kitchen with room for an island or kitchen table, vinyl plank flooring throughout, all impact rated windows, metal roof, indoor laundry room, and spacious covered

  

  Lindsay Ryan

  EXP Realty LLC

  (786) 952-7185

  28151 Helen Ave, Summerland Key, FL 33042
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  /115

  $12,250,000 Sold May 07, 2025

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $2,506/SF
  • 44 Days On Market

  Current Estimated Value $6,513,006

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  785 Sawyer Dr, Cudjoe Key, FL 33042
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  /2

  Est $468,984 Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 6% Below List Price

  Last Sold Price $500,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty
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  /30

  $750,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft

  630 Barry Ave, Little Torch Key, FL 33042

  Rarely does a property offer this much space and such rapid water access. Located near the end of a quiet, private street, this home sits on nearly three-quarters of an acre with 204.5 feet of canal frontage. The existing 3BD/2BA residence features a roof-covered deck built for sunset views, and while it needs some TLC, the value is in the land and the location. Build the outdoor oasis you've

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 886-1075

  630 Barry Ave, Little Torch Key, FL 33042
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  /26

  $390,000 Sold Jul 10, 2025

  27873 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 686 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $569/SF
  • 70 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch 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

  Last Sold Summary

  • $736/SF

  Last Sold Price $660,000

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)
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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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  /64

  $809,000 Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

  Current Estimated Value $809,683

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

  3714 Pine St, Big Pine Key, FL 33043
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  /2

  Est $183,993 Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 7% Below List Price

  Last Sold Price $172,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
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  /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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  /33

  $799,000 Sold Apr 28, 2025

  24833 Park Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $685/SF
  • 115 Days On Market

  Current Estimated Value $773,012

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  24833 Park Dr, Summerland Key, FL 33042
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  Est $3,059,776 Not Listed For Sale

  999 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft
  • Built 2024

  999 Flagship Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $850/SF

  Last Sold Price $3,000,000

  Last Listing Agent Lee Sanders KeyIsle Realty
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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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  /8

  $340,000 Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
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  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • $828/SF
  • 66 Days On Market

  Last Sold Price $715,000
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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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  /52

  $1,530,000 Sold Jan 16, 2026

  1370 Long Beach Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,181 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $1,296/SF
  • 33 Days On Market

  Current Estimated Value $1,545,429

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

  1370 Long Beach Dr, Big Pine Key, FL 33043
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  /2

  Est $1,208,477 Not Listed For Sale

  29565 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2019

  29565 Ranger Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Below List Price
  • $930/SF

  Last Sold Price $1,250,000

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
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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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  /21

  $775,000 Sold Mar 23, 2026

  27360 Saint Croix Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $673/SF
  • 272 Days On Market

  Current Estimated Value $848,279

  Last Listing Agent Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
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  /14

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043

  Last Sold Summary

  • 64 Days On Market

  Last Sold Price $90,000

  Last Listing Agent Yisel Montes The Keyes Company
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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
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  /58

  $760,000 Sold Aug 19, 2025

  640 Carolyn Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $896/SF
  • 66 Days On Market

  Current Estimated Value $759,784

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
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  /2

  Est $1,024,636 Not Listed For Sale

  18954 Acosta Trail, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2013

  18954 Acosta Trail, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $991/SF

  Last Sold Price $999,000

  Last Listing Agent Lisa Swanson The Agency Florida Keys
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  /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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  /43

  $1,700,000 Sold Jan 30, 2026

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $820/SF
  • 140 Days On Market

  Current Estimated Value $1,690,104

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
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  /2

  Est $456,014 Not Listed For Sale

  520 Blackbeard Rd, Little Torch Key, FL 33042

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 6% Below List Price

  Last Sold Price $485,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
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  $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
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  /26

  $239,000 Sold Jun 30, 2025

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 74 Days On Market

  Current Estimated Value $244,972

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
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  Not Listed For Sale

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

  Last Sold Summary

  Last Sold Price $30,000

  Last Listing Agent Allan Leder Preferred Properties (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
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  /44

  $700,000 Sold Jan 09, 2026

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $810/SF
  • 23 Days On Market

  Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
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  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  Last Sold Summary

  • 198 Days On Market

  Last Sold Price $242,000

  Last Listing Agent Carmen David Xcellence Realty
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  /49

  $980,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  29559 Ranger Ave, Big Pine Key, FL 33043

  This well desired location and immaculately maintained home is 5 minutes from world class boating, fishing, diving and snorkeling. Located in Pine Channel Estates for the fastest and easiest direct access to the ocean or the endless options of bay-side boating adventures. Boasting a 75' concrete seawall with a 14K boat lift, davits, and drop-down on/off boat access, there is even a dive board for

  

  Donna Halstead

  Coldwell Banker Schmitt RE Co.

  (833) 637-5679

  29559 Ranger Ave, Big Pine Key, FL 33043

Showing Results 161 - 200, Page 5 of 18