Summerland Key, FL Homes

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  /18

  $250,000

  Sold Feb 24, 2026

  138 Sands Rd, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 442 Sq Ft
  • Built 1969

  Last Sold Summary

  • 9% Below List Price
  • $566/SF
  • 16 Days On Market

  Last Listing Agent Kate Zhang Kylin Realty LLC

  138 Sands Rd, Big Pine Key, FL 33043
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  /61

  Est $1,771,498

  Not Listed For Sale

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1998

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Rhonda Williams 2150
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  /42

  $805,000

  $44K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  27416 Martinique Ln, Summerland Key, FL 33042

  Discover the relaxed vibe of the Lower Keys and uncover your sense of 'Place'. This tropical home on Ramrod Key is not just 4 walls, it is a canvas to create your most prized and cherished, Florida Keys memories. Located in the sought after Breezeswept Beach Estates neighborhood. This waterfront home offers concrete dock and 60 feet on the water and a super Kayak /SUP swim-out launch. Wide open

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  27416 Martinique Ln, Summerland Key, FL 33042
• 

  $545,000

  Sold Feb 04, 2026

  114 Newfound Harbor Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $649/SF
  • 65 Days On Market

  Current Estimated Value $544,650

  Last Listing Agent Jennifer Hamill Coldwell Banker Schmitt RE Co

  114 Newfound Harbor Rd, Big Pine Key, FL 33043
• 

  

  

  /49

  Est $735,538

  Not Listed For Sale

  27317 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,029 Sq Ft
  • Built 2012

  27317 Cayman Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 262 Days On Market

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo
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  /84

  $3,199,000

  $500K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,744 Sq Ft

  17183 Coral Dr, Summerland Key, FL 33042

  Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

  Jan Fritz Coldwell Banker Schmitt RE Co.

  17183 Coral Dr, Summerland Key, FL 33042
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  /37

  $725,000

  Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Current Estimated Value $757,428

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /81

  Est $1,281,987

  Not Listed For Sale

  23041 Snapper Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1992

  23041 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.
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  /2

  $85,000

  • Land
  • 6,667 Sq Ft
  • $555,279 per Acre

  Vacant Central Ave, Big Pine Key, FL 33043

  Tier 2 parcel with potential eligibility for ROGO points toward future building permits in Monroe County. Buyer to verify ROGO point availability and requirements with Monroe County. Adjacent lot is for sale MLS#618997

  Deni Heintzelman KeyIsle Realty

  Vacant Central Ave, Big Pine Key, FL 33043
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  /4

  $837,000

  Sold Jul 10, 2026

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 7% Below List Price
  • $943/SF
  • 37 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  /2

  Est $873,811

  Not Listed For Sale

  22910 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1988

  22910 Privateer Dr, Summerland Key, FL 33042
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  /66

  $2,795,000

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

  Greg MacLaren Internet Realty of the Florida Keys

  333 Indies Rd, Ramrod Key, FL 33042
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  /47

  $945,000

  Sold Oct 03, 2025

  29487 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $751/SF
  • 99 Days On Market

  Current Estimated Value $1,027,533

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043
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  /2

  Est $1,510,132

  Not Listed For Sale

  27362 Anguila Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1975

  27362 Anguila Ln, Summerland Key, FL 33042
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  /32

  $2,100,000

  New Construction

  • 5 Beds
  • 4 Baths
  • 2,886 Sq Ft

  662 Blackbeard Rd, Little Torch Key, FL 33042

  Pre-Construction Luxury Home | Jolly Roger EstatesIntroducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This CBS-built, fortress-like home is designed for durability, efficiency, and modern coastal living. The two-story floor plan offers 5 bedrooms, 4 bathrooms, and 2,886 square feet of living space, along with a spacious downstairs storage

  Lanny Gardner Bluescape Real Estate

  662 Blackbeard Rd, Little Torch Key, FL 33042
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  /62

  $720,000

  Sold May 18, 2026

  28151 Helen Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $511/SF
  • 51 Days On Market

  Current Estimated Value $734,528

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  28151 Helen Ave, Summerland Key, FL 33042
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  /12

  Est $659,552

  Not Listed For Sale

  27007 Angelfish Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1,201 Sq Ft
  • Built 1967

  27007 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 281 Days On Market

  Last Listing Agent Sabrina Liguori Key West Vacation Properties & Realty, LLC (KW)
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  /15

  $644,500

  • Land
  • 15,200 Sq Ft
  • $1,847,001 per Acre

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042
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  /29

  $720,000

  Sold Apr 17, 2026

  630 Barry Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Built 2005

  Last Sold Summary

  • 28% Below List Price
  • $678/SF
  • 86 Days On Market

  Current Estimated Value $866,350

  Last Listing Agent Brenda Thomas Island Welcome Real Estate

  630 Barry Ave, Little Torch Key, FL 33042
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  /34

  Est $955,384

  Not Listed For Sale

  320 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  320 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)
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  /100

  $8,995,000

  $955K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach — a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  16750 Old State Road 4a, Summerland Key, FL 33042
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  /45

  $710,000

  Sold Feb 05, 2026

  27163 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2018

  Last Sold Summary

  • 10% Below List Price
  • $477/SF
  • 238 Days On Market

  Current Estimated Value $741,416

  Last Listing Agent Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /37

  Est $931,525

  Not Listed For Sale

  139 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1994

  139 Le Grand Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.
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  /49

  $3,495,000

  • 4 Beds
  • 3.5 Baths
  • 2,766 Sq Ft

  414 Caribbean Dr E, Summerland Key, FL 33042

  OCEANFRONT, POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful newly

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  414 Caribbean Dr E, Summerland Key, FL 33042
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  /14

  $225,000

  Sold Apr 01, 2026

  27398 Jamaica Ln, Ramrod Key, FL 33042

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  Last Sold Summary

  • 25% Below List Price
  • 173 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /27

  Est $1,658,697

  Not Listed For Sale

  22836 Port Royal Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 1987

  22836 Port Royal Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Sandra Tuttle American Caribbean Real Estate Lower Keys
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  /99

  $4,650,000

  $345K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 4,687 Sq Ft

  3742 Seagrape St, Big Pine Key, FL 33043

  Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb

  Ally Kelley Ocean Sotheby's International

  3742 Seagrape St, Big Pine Key, FL 33043
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  /36

  $1,200,000

  Sold Jun 05, 2026

  831 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1980

  Last Sold Summary

  • 19% Below List Price
  • $1,038/SF
  • 87 Days On Market

  Current Estimated Value $1,251,738

  Last Listing Agent Miranda Dender Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  831 W Indies Dr, Summerland Key, FL 33042
• 

  

  /37

  Est $887,053

  Not Listed For Sale

  81 Coral Ave, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,535 Sq Ft
  • Built 1988

  81 Coral Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Jenny Perry Preferred Properties (KW)
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  /19

  $425,000

  $50K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $8,500,000 per Acre

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
• 

  

  /30

  $1,185,000

  Sold Nov 17, 2025

  478 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $1,062/SF
  • 0 Days On Market

  Current Estimated Value $1,178,993

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /34

  Est $795,115

  Not Listed For Sale

  28551 Buccaneer Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 841 Sq Ft
  • Built 1976

  28551 Buccaneer Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Monika Rydzak eXp Realty LLC KW Branch
• 

  

  /13

  $450,000

  $92K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $2,812,500 per Acre

  1147 Basque Ln, Cudjoe Key, FL 33042

  BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water

  Brad Baker Key to the Keys Real Estate, Inc

  1147 Basque Ln, Cudjoe Key, FL 33042
• 

  

  /29

  $825,000

  Sold Feb 27, 2026

  17245 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $661/SF
  • 104 Days On Market

  Current Estimated Value $873,424

  Last Listing Agent Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /45

  Est $2,072,010

  Not Listed For Sale

  20942 6th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • Built 1994

  20942 6th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /4

  $350,000

  • Land
  • 8,276 Sq Ft
  • $1,842,105 per Acre

  22776 Overseas, Cudjoe Key, FL 33042

  Prime Cudjoe Key Commercial Opportunity! Cleared Suburban Commercial parcel offering outstanding highway frontage and excellent visibility on the Overseas Highway. Zoning SC allows for a variety of uses flood zone AE 9 tier 3 lot. For investment or owner-use. Owner financing may be available to qualified buyers. Bring your vision and capitalize on one of the Lower Keys' high-exposure commercial

  Rose Dell Keller Williams Key West Compass Realty

  22776 Overseas, Cudjoe Key, FL 33042
• 

  $1,070,000

  Sold Jun 11, 2026

  1547 Gardenia Ln, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 2025

  Last Sold Summary

  • 18% Below List Price
  • $563/SF
  • 93 Days On Market

  Current Estimated Value $1,070,147

  Last Listing Agent Dorothy Santiago Keller Williams Realty Profess

  1547 Gardenia Ln, Big Pine Key, FL 33043
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  /43

  Est $1,108,897

  Not Listed For Sale

  17055 Kingfish Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1988

  17055 Kingfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Team Kaufelt Truman & Co. (KW)
• 

  

  /18

  $799,000

  • 3 Beds
  • 1 Bath
  • 1,043 Sq Ft

  550 Pine Ln, Big Pine Key, FL 33043

  This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof,

  Justyn Ewald Expert Realty LLC

  550 Pine Ln, Big Pine Key, FL 33043
• 

  

  /40

  $1,300,000

  Sold Feb 26, 2026

  537 Heck Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • Built 1997

  Last Sold Summary

  • $914/SF
  • 29 Days On Market

  Current Estimated Value $1,286,510

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  537 Heck Ave, Summerland Key, FL 33042

Showing Results 441 - 480, Page 12 of 18