Summerland Key, FL Homes

• 

  

  

  /61

  Est $2,136,939

  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
• 

  

  

  /15

  $644,500

  • Land

  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
• 

  

  

  /16

  $785,000

  Sold Jul 25, 2025

  27384 Barbuda Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1993

  Last Sold Summary

  • 17% Below List Price
  • $668/SF
  • 125 Days On Market

  Current Estimated Value $824,850

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  27384 Barbuda Ln, Summerland Key, FL 33042
• 

  

  

  /81

  Est $1,303,761

  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
• 

  

  

  /100

  $8,995,000

  $955K PRICE DROP

  • 6 Beds
  • 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
• 

  

  /14

  $1,250,000

  Sold Aug 11, 2025

  365 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $893/SF
  • 47 Days On Market

  Current Estimated Value $1,243,497

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  365 Pirates Rd, Summerland Key, FL 33042
• 

  /2

  Est $841,334

  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

  Last Sold Summary
• 

  

  /50

  $3,495,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 4 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

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  414 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /59

  $900,000

  Sold Oct 31, 2025

  28550 Doubloon Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1996

  Last Sold Summary

  • 18% Below List Price
  • $380/SF
  • 181 Days On Market

  Current Estimated Value $992,381

  Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

  28550 Doubloon Rd, Summerland Key, FL 33042
• 

  /2

  Est $1,598,754

  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

  Last Sold Summary
• 

  

  /9

  $225,000

  • Land
  • 7,405 Sq Ft
  • $1,323,529 per Acre

  26837 Overseas Hwy, Summerland Key, FL 33042

  Rare opportunity to acquire a commercially zoned, vacant land parcel, fronting on U.S. Highway 1 in Ramrod Key, Florida. The subject property is 7,340 square foot vacant parcel with 50 feet of direct Overseas Highway frontage. Zoned Suburban Commercial (SC) under the Monroe County Land Development Code.

  Casey Prindle Nicklaus Vance

  26837 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /24

  $710,000

  Sold Dec 18, 2025

  31120 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 864 Sq Ft
  • Built 2022

  Last Sold Summary

  • 9% Below List Price
  • $822/SF
  • 83 Days On Market

  Current Estimated Value $713,388

  Last Listing Agent David Kaufmann Century 21 Circle

  31120 Avenue J, Big Pine Key, FL 33043
• 

  

  /12

  Est $639,592

  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
• 

  /2

  $50,000

  $125K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $312,500 per Acre

  0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042

  **PROPERTY DESCRIPTION** Oceanfront vacant lot in Cudjoe Key, FL (Block 14, Lot 1). Buildable residential parcel located in a platted subdivision, offering open water views and excellent investment potential. No ROGO permit currently in place; buyer must obtain allocation prior to building. Conveniently located near Key West with access to boating, fishing, and diving. Great opportunity to own

  Jaysen Larrieux LoKation

  0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042
• 

  

  /5

  $328,000

  Sold Mar 27, 2026

  28292 Dorothy Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 830 Sq Ft
  • Built 1975

  Last Sold Summary

  • $395/SF
  • 4 Days On Market

  Last Listing Agent Lauren Dunn Coldwell Banker Schmitt Islamorada

  28292 Dorothy Ave, Summerland Key, FL 33042
• 

  

  /34

  Est $949,564

  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
• 

  

  /55

  $3,025,000

  New Construction

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

  17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042

  A rare double-parcel waterfront opportunity in Lower Sugarloaf Key - offering a newly constructed home plus an adjacent buildable lot, creating the ultimate private boating compound.The newly built 3BD/2.5BA residence with an office/den & laundry/utility room spans 2,288sf on a 16,445sf lot and is thoughtfully designed with an open-concept layout, abundant natural light, and sweeping water

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042
• 

  

  /43

  $950,000

  Sold Jun 25, 2025

  3881 Joyce Rd, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,428 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $665/SF
  • 69 Days On Market

  Current Estimated Value $975,849

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

  3881 Joyce Rd, Big Pine Key, FL 33043
• 

  

  /41

  Est $430,326

  Not Listed For Sale

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  Last Sold Summary

  • 95 Days On Market
• 

  

  /99

  $4,995,000

  • 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
• 

  

  /26

  $335,000

  Sold May 12, 2026

  31042 Avenue J, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 16% Below List Price
  • $372/SF
  • 8 Days On Market

  Current Estimated Value $487,214

  Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall

  31042 Avenue J, Big Pine Key, FL 33043
• 

  

  /37

  Est $929,542

  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
• 

  

  /19

  $430,000

  $45K PRICE DROP

  • Land
  • 2,078 Sq Ft
  • $9,013,859 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

  Lanny Gardner Bluescape Real Estate

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

  

  /36

  $700,000

  Sold Jan 29, 2026

  24830 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $589/SF
  • 7 Days On Market

  Current Estimated Value $717,310

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  24830 Park Dr, Summerland Key, FL 33042
• 

  

  /27

  Est $1,735,090

  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
• 

  

  /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
• 

  

  /32

  $1,282,100

  Sold Nov 04, 2025

  32857 Tortuga Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1994

  Last Sold Summary

  • 8% Below List Price
  • $916/SF
  • 23 Days On Market

  Current Estimated Value $1,285,332

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  32857 Tortuga Ln, Big Pine Key, FL 33043
• 

  

  /37

  Est $890,800

  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
• 

  

  /13

  $5,538

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

  28514 Channel View Dr, Little Torch Key, FL 33042

  This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished or furnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour

  Joseph Danieli AKT Realty LLC

  28514 Channel View Dr, Little Torch Key, FL 33042
• 

  /2

  $357,000

  Sold Nov 07, 2025

  31145 Hibiscus Dr, Big Pine Key, FL 33043

  • Land
  • 5,399 Sq Ft
  • $2,879,800 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 222 Days On Market

  Current Estimated Value $359,085

  Last Listing Agent Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  31145 Hibiscus Dr, Big Pine Key, FL 33043
• 

  

  /34

  Est $797,950

  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
• 

  

  /48

  $950,000

  Under Contract

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

  29175 Aster Ln, Big Pine Key, FL 33043

  Discover exceptional Florida Keys living in this impeccably kept 3-bedroom, 2-bath waterfront residence on Big Pine Key featuring direct, bridge-free access to Pine Channel--an authentic boater's paradise. Built for performance, longevity, and security, this property includes a metal roof, impact-resistant windows and doors, Hardie Board siding plus solar panels delivering reduced energy costs,

  Scott Brisson EXP Realty LLC Branch Office

  29175 Aster Ln, Big Pine Key, FL 33043
• 

  

  /35

  $560,000

  Sold Aug 29, 2025

  19616 Aztec St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,129 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $496/SF
  • 196 Days On Market

  Current Estimated Value $591,916

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  19616 Aztec St, Summerland Key, FL 33042
• 

  

  /45

  Est $2,031,834

  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
• 

  

  /21

  $897,000

  • 2 Beds
  • 1 Bath
  • 574 Sq Ft

  9W Cooks, Cook Island Key, FL 33043

  Situated just offshore in the Lower Florida Keys, Cook's Key Lime Cottage offers a sublime blend of modern comfort and tropical allure. Perfect for avid fishermen and outdoor enthusiasts, real estate investors with a desire for an entirely unique Florida Keys experiential property to add to their portfolio, or those seeking a piece of the Florida Keys to where they can escape. Beautiful inside

  Greg Gordon The Island Collective Realty

  9W Cooks, Cook Island Key, FL 33043
• 

  

  /10

  $2,000,000

  Sold Jul 14, 2025

  441 Airport Dr N, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $887/SF
  • 166 Days On Market

  Current Estimated Value $2,049,978

  Last Listing Agent Jonathan Minerick Homecoin.com

  441 Airport Dr N, Summerland Key, FL 33042
• 

  

  /43

  Est $1,128,691

  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
• 

  

  /21

  $459,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 668 Sq Ft

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

  Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
• 

  

  /50

  $1,599,000

  Sold Jun 10, 2025

  29655 Forrestal Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $828/SF
  • 42 Days On Market

  Current Estimated Value $1,589,077

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  29655 Forrestal Ave, Big Pine Key, FL 33043
• 

  

  /50

  Est $953,188

  Not Listed For Sale

  17396 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1992

  17396 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market

Showing Results 521 - 560, Page 14 of 18