Summerland Key, FL Homes

• 

  

  

  /7

  $800,000

  • Land
  • 0.18 Acre
  • $4,444,444 per Acre

  28525 Jolly Roger Dr, Little Torch Key, FL 33042

  RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

  Fazana Haniff FHG Realty, LLC.

  28525 Jolly Roger Dr, Little Torch 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 $819,369

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  27384 Barbuda Ln, Summerland Key, FL 33042
• 

  

  

  /40

  Est $973,501 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  93 Venetian Way, Summerland Key, FL 33042

  93 Venetian Way, Summerland Key, FL 33042
• 

  

  

  /47

  $455,000

  • Land

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

  ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 496, Cudjoe 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 $1,233,307

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  365 Pirates Rd, Summerland Key, FL 33042
• 

  

  /48

  Est $657,382 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  27018 Angelfish Rd, Summerland Key, FL 33042

  27018 Angelfish Rd, Summerland Key, FL 33042
• 

  

  /22

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  1331 Hudgins Dr, Summerland Key, FL 33042

  Location, Location and Location Enter the Palm Tree Stained-glass Impact door to 24-inch Travertine floors and Nine-foot ceilings throughout. The Master Bedroom has double French doors With a Tropical Stained-glass Floral Design. 1060 sq-ft 2 Bedroom 2 Bath, nine-foot ceilings, All Travertine/Tile Bathrooms with Skylights, heaters and extra storage, finished closets and two waterside triple

  Camilo Perez Home Sold Realty, LLC

  1331 Hudgins Dr, 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 $973,805

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

  28550 Doubloon Rd, Summerland Key, FL 33042
• 

  

  /19

  Est $909,148 Not Listed For Sale

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

  221 Cutthroat Dr, Summerland Key, FL 33042

  221 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /42

  $649,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  3231 Pompano St, Big Pine Key, FL 33043

  Ultimate Privacy in Big Pine KeyStep into an extraordinary sanctuary of seclusion, where tropical elegance meets unmatched exclusivity. 1 of only 2 homes in the entire Seaview subdivision of Big Pine Key.3231 Pompano Drive is a beautifully renovated island retreat set on a 10,000 sq. ft. lot, surrounded by untouched nature and abundant wildlife. No additional homes can ever be built, ensuring

  Dawn McComish Lokation Real Estate

  3231 Pompano St, Big Pine Key, FL 33043
• 

  

  /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

  Last Listing Agent David Kaufmann Century 21 Circle

  31120 Avenue J, Big Pine Key, FL 33043
• 

  /2

  Est $1,026,694 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  27310 W Indies Dr, Summerland Key, FL 33042

  27310 W Indies Dr, Summerland Key, FL 33042
• 

  

  /9

  $3,500,000

  • Land

  19657 Seminole St, Sugarloaf Key, FL 33042

  Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

  Derek Epperly Engel & Volkers Key West

  19657 Seminole St, Sugarloaf Key, FL 33042
• 

  

  /30

  $540,000 Sold Mar 04, 2025

  31353 Avenue E, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 7% Below List Price
  • $662/SF
  • 256 Days On Market

  Current Estimated Value $552,830

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  31353 Avenue E, Big Pine Key, FL 33043
• 

  

  /36

  Est $1,150,930 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,518 Sq Ft

  27328 Jamaica Ln, Summerland Key, FL 33042

  27328 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /29

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft

  31525 Avenue A, Big Pine Key, FL 33043

  $525K Opportunity with so much potential. Privacy fence with 3 big double gates with access from both streets and no neighbor across the street. on Ave A. CBS 3bd/2bth ground level home. Central AC, Tile Floors, Double corner lot. 100 X 100. Lots of parking, or RV parking. Room for pool and entertaining. Patio deck area. Concrete pads for shed etc. Close to community park, public boat ramp nearby

  Rose Dell Keller Williams Key West Compass Realty

  31525 Avenue A, Big Pine Key, FL 33043
• 

  

  /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 $959,583

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

  3881 Joyce Rd, Big Pine Key, FL 33043
• 

  

  /61

  Est $2,000,269 Not Listed For Sale

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

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  17153 Buttonwood Dr W, Summerland Key, FL 33042
• 

  

  /60

  $2,499,000 Open Sun 10AM - 12PM

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft

  556 Caribbean Dr E, Summerland Key, FL 33042

  The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /31

  $690,000 Sold May 30, 2025

  29393 Cypress Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $781/SF
  • 150 Days On Market

  Current Estimated Value $710,402

  Last Listing Agent Jennifer Weeks Select Properties of NWFL

  29393 Cypress Dr, Big Pine Key, FL 33043
• 

  

  /39

  Est $1,708,070 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  17056 Wahoo Ln, Summerland Key, FL 33042

  17056 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /24

  $849,000

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

  853 Indies Rd, Summerland Key, FL 33042

  Move right into this well-maintained 3-bedroom, 2-bath canal front home, built in 2006 and cared for with pride. The bright, open layout features a split floor plan that offers comfortable space for everyday living and entertaining.The primary bedroom includes an en-suite bath and a versatile bonus room -- ideal for a home office, nursery, or cozy retreat. Step outside to enjoy peaceful canal

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  853 Indies Rd, Summerland Key, FL 33042
• 

  

  /38

  $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

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

  24830 Park Dr, Summerland Key, FL 33042
• 

  

  /81

  Est $1,526,474 Not Listed For Sale

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

  23041 Snapper Ln, Summerland Key, FL 33042

  23041 Snapper Ln, Summerland Key, FL 33042
• 

  

  /35

  $799,000

  • 3 Beds
  • 3 Baths
  • 1,224 Sq Ft

  3672 Fox St, Big Pine Key, FL 33043

  Discover a peaceful Keys escape on a quiet canal in Big Pine Key. This attractive 3-bedroom, 3-bath home blends relaxed, nature-forward living with modern comforts.Bright, open living area with high ceilingsUpdated kitchen with stainless steel appliances, granite counters, and ample cabinetry. Private master suite with en-suite bath and direct balcony access.Two additional bedrooms ideal for

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  3672 Fox St, Big Pine Key, FL 33043
• 

  

  /35

  $902,500 Sold Apr 11, 2025

  346 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $760/SF
  • 62 Days On Market

  Current Estimated Value $929,008

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  346 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /19

  Est $830,494 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22910 Privateer Dr, Summerland Key, FL 33042

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /53

  $1,710,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /72

  $3,436,000 Sold May 16, 2025

  5460 Dorn Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,134 Sq Ft
  • Built 1996

  Last Sold Summary

  • 7% Below List Price
  • $1,610/SF
  • 30 Days On Market

  Current Estimated Value $3,442,409

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  5460 Dorn Rd, Summerland Key, FL 33042
• 

  /2

  Est $1,539,007 Not Listed For Sale

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

  27362 Anguila Ln, Summerland Key, FL 33042

  27362 Anguila Ln, Summerland Key, FL 33042
• 

  

  /25

  $745,000

  • Land

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

  Barbara Eads Barbara Eads Realty

  28587 Peg Leg Rd Little Torch Aly, Little Torch 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 $1,293,119

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  32857 Tortuga Ln, Big Pine Key, FL 33043
• 

  

  /34

  Est $927,088 Not Listed For Sale

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

  320 Spanish Main Dr, Summerland Key, FL 33042

  320 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /49

  $329,000

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
• 

  

  /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 $584,507

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  19616 Aztec St, Summerland Key, FL 33042
• 

  

  /41

  Est $441,828 Not Listed For Sale

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

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

  

  /31

  $624,900

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  30023 Pine Channel Rd, Big Pine Key, FL 33043

  Discover tranquil Keys living at 30023 Pine Channel Rd, a charming 3-bedroom, 2-bathroom home offering peaceful seclusion with effortless access to the Overseas Highway. Set on a generous lot and surrounded by mature, beautifully established trees, this property delivers the perfect blend of privacy, nature, and convenience.Step inside to find 1,218 sq ft of comfortable living space. The

  Sam Williams Coldwell Banker Schmitt Real Estate Co.

  30023 Pine Channel Rd, Big Pine 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 $2,007,498

  Last Listing Agent Jonathan Minerick Homecoin.com

  441 Airport Dr N, Summerland Key, FL 33042
• 

  

  /37

  Est $899,714 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  139 Le Grand Ln, Summerland Key, FL 33042

  139 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /82

  $3,699,000

  • 3 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

Showing Results 561 - 600, Page 15 of 18