Homes in ZIP Code 33042

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  /16

  $1,400,000

  Sold Mar 16, 2026

  570 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $933/SF
  • 14 Days On Market

  Current Estimated Value $1,433,000

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  570 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  

  /15

  Not Listed For Sale

  8 Calico Jack Circle Cir, Verifying, FL 33042

  8 Calico Jack Circle Cir, Verifying, FL 33042

  Last Sold Summary

  • 18 Days On Market
• 

  

  

  /19

  $215,000

  $35K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $4,300,000 per Acre

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  (645) 229-8475

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
• 

  

  

  /49

  $650,000

  Sold Aug 20, 2025

  27317 Cayman Ln, Summerland Key, FL 33042

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

  Last Sold Summary

  • 28% Below List Price
  • $632/SF
  • 262 Days On Market

  Current Estimated Value $697,241

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

  27317 Cayman Ln, Summerland Key, FL 33042
• 

  

  

  /59

  Not Listed For Sale

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

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

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

  Last Sold Summary

  • 76 Days On Market
• 

  

  /39

  $1,399,000

  $200K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  20838 5th Ave W, Cudjoe Key, FL 33042

  Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (877) 473-4184

  20838 5th Ave W, Cudjoe Key, FL 33042
• 

  

  /5

  $725,000

  Sold Jul 30, 2025

  19462 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $520/SF
  • 3 Days On Market

  Current Estimated Value $733,282

  Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

  19462 Canal Dr, Summerland Key, FL 33042
• 

  

  /40

  Not Listed For Sale

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1996

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /44

  $1,200,000

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

  17286 Jamaica Ln, Summerland Key, FL 33042

  Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 702-3934

  17286 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /27

  $300,000

  Sold Nov 26, 2025

  27983 Snapper Ln, Little Torch Key, FL 33042

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

  Last Sold Summary

  • 9% Below List Price
  • $446/SF
  • 60 Days On Market

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  27983 Snapper Ln, Little Torch Key, FL 33042
• 

  

  /37

  Not Listed For Sale

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 9 Days On Market
• 

  

  /51

  $1,099,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  22953 John Silver Ln, Summerland Key, FL 33042

  Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 241-8464

  22953 John Silver Ln, Summerland Key, FL 33042
• 

  /2

  $55,000

  Sold Oct 22, 2025

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  • Land
  • 5,000 Sq Ft
  • $479,160 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /20

  Not Listed For Sale

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 80 Days On Market
• 

  

  /66

  $799,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 842 Sq Ft

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

  Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  (645) 230-0325

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
• 

  

  /46

  $1,390,000

  Sold Aug 26, 2025

  229 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $1,207/SF
  • 30 Days On Market

  Current Estimated Value $1,392,633

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  229 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /50

  Est $825,130

  Not Listed For Sale

  489 Pirates Rd, Little Torch Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,638 Sq Ft
  • Built 1984

  489 Pirates Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 38 Days On Market
• 

  

  /60

  $1,299,999

  $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  28560 Doubloon Rd, Summerland Key, FL 33042

  Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (645) 218-9799

  28560 Doubloon Rd, Summerland Key, FL 33042
• 

  

  /68

  $2,250,000

  Sold Apr 03, 2026

  24266 Caribbean Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Below List Price
  • $1,095/SF
  • 14 Days On Market

  Current Estimated Value $2,273,007

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  24266 Caribbean Dr W, Summerland Key, FL 33042
• 

  

  /35

  Est $219,010

  Not Listed For Sale

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /41

  $1,899,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  28573 Le Grand Rd, Little Torch Key, FL 33042

  This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (855) 560-6494

  28573 Le Grand Rd, Little Torch Key, FL 33042
• 

  

  /29

  $740,000

  Sold Oct 31, 2025

  27138 Dolphin Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2022

  Last Sold Summary

  • 14% Below List Price
  • $561/SF
  • 181 Days On Market

  Current Estimated Value $739,756

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
• 

  

  /51

  Not Listed For Sale

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2006

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  Last Sold Summary

  • 27 Days On Market
• 

  

  /10

  $499,000

  • Land

  63 Sugarloaf Dr, Sugarloaf Key, FL 33042

  Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (855) 917-4422

  63 Sugarloaf Dr, Sugarloaf Key, FL 33042
• 

  

  /47

  $1,100,000

  Sold Jun 27, 2025

  21014 7th Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $808/SF
  • 102 Days On Market

  Current Estimated Value $1,106,731

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  21014 7th Ave, Summerland Key, FL 33042
• 

  

  /11

  Not Listed For Sale

  LOT 38 W Indies Dr, Ramrod Key, FL 33042

  LOT 38 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 144 Days On Market
• 

  

  /28

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft

  290 46th St, Summerland Key, FL 33042

  Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport! This property is a fixer-upper, or teardown, located on Summerland Key, at the base of the airport runway. 2/1 on one side, and an additional 12 x32 en suite with a separate entrance on the other side. The home sits on a rare double lot totaling 11,000 SF. If you like privacy, this is it,

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (645) 219-1684

  290 46th St, Summerland Key, FL 33042
• 

  

  /7

  $4,275,000

  Sold Mar 04, 2026

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $1,371/SF
  • 114 Days On Market

  Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
• 

  

  /14

  Est $177,468

  Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 2 Days On Market
• 

  

  /112

  $975,000

  $215K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  22748 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor living space is a dream with an in-ground concrete saltwater pool (2021) & waterfall feature, 12k lb boat lift (2021), 60' concrete seawall, & an expansive 10' deep back porch (nearly 700 sq ft of porches), all perfect for outdoor dining,

  

  Lindsay Ryan

  EXP Realty LLC

  (645) 251-6583

  22748 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /41

  $775,000

  Sold May 01, 2026

  22939 Privateer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1988

  Last Sold Summary

  • $602/SF
  • 3 Days On Market

  Current Estimated Value $845,047

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  22939 Privateer Dr, Summerland Key, FL 33042
• 

  

  /21

  Not Listed For Sale

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1978

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  Last Sold Summary

  • 0 Days On Market
• 

  

  /43

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 2,368 Sq Ft

  27395 Saint Lucie Ln, Summerland Key, FL 33042

  Professional photos coming soon! Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek

  

  Michelle Vanhoose

  Coldwell Banker Schmitt Real Estate Co.

  (786) 882-1637

  27395 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /55

  $5,003,500

  Sold Jan 05, 2026

  1151 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft
  • Built 2007

  Last Sold Summary

  • 28% Below List Price
  • $1,266/SF
  • 47 Days On Market

  Current Estimated Value $5,337,716

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1151 Ocean Dr, Summerland Key, FL 33042
• 

  

  /38

  Est $1,350,145

  Not Listed For Sale

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1994

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  Last Sold Summary

  • 15 Days On Market
• 

  

  /22

  $685,000

  $29K PRICE DROP

  • 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
• 

  

  /34

  $600,000

  Sold Sep 22, 2025

  19557 Mayan St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $607/SF
  • 186 Days On Market

  Current Estimated Value $618,032

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, Summerland Key, FL 33042
• 

  

  /8

  Est $189,678

  Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 7 Days On Market
• 

  

  /38

  $1,399,000

  $100K PRICE DROP

  • 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) 808-1276

  51 Drost Dr, Summerland Key, FL 33042
• 

  /2

  $48,000

  Sold Mar 13, 2026

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 26% Below List Price
  • 250 Days On Market

  Current Estimated Value $1,295,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

Showing Results 41 - 80, Page 2 of 18