Homes in ZIP Code 33042

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  /45

  $1,599,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  17227 Allamanda Dr, Summerland Key, FL 33042

  Welcome to your own slice of paradise in the desirable Sugarloaf Shores neighborhood of the Lower Keys! This beautifully designed 3 bedroom, 2 bath home offers 1,788 sq. ft. of inviting living space that perfectly blends comfort, quality, and the laid-back island lifestyle. Located on the no-bridge side of Sugarloaf Shores, this property provides quick water access to world-class fishing, diving,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 803-0852

  17227 Allamanda Dr, Summerland Key, FL 33042
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  /8

  $340,000 Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 0.29 Acre
  • $1,184,832 per Acre

  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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  /3

  Est $498,667 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042
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  /125

  $1,150,000

  • 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 a new concrete pool & waterfall feature, 12k lb boat lift, 60' concrete seawall, & an expansive 10 foot deep back porch (total of nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, &

  

  Lindsay Ryan

  EXP Realty LLC

  (786) 807-7897

  22748 Blackbeard Ln, Cudjoe Key, FL 33042
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  /21

  $380,000 Sold Jun 24, 2025

  27848 Lobster Tail Trail, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft
  • Built 1971

  Last Sold Summary

  • 24% Below List Price
  • $688/SF
  • 248 Days On Market

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  27848 Lobster Tail Trail, Little Torch Key, FL 33042
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  /2

  Est $502,153 Not Listed For Sale

  • Studio
  • 1 Bath

  27418 Jamaica Ln, Ramrod Key, FL 33042

  27418 Jamaica Ln, Ramrod Key, FL 33042
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  /24

  $799,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  219 Caribbean Dr E, Summerland Key, FL 33042

  Waterfront Home in Summerland Key. Quick access to both Ocean & Gulf. Partial open water view. 60' concrete seawall with deep water dockage up to + - 50' Boats. Room for an RV. Great location with a private airstrip on the island. Close to the walking, biking Heritage Trail. Minutes to Key West. Home could use a little TLC. No HOA, No Lock Box. Easy to show. Call today to preview. Please don't

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (786) 822-7016

  219 Caribbean Dr E, 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 $765,572

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
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  /33

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  27417 Tobago Ln, Ramrod Key, FL 33042

  This custom-built 3-bedroom, 2-bathroom residence on Ramrod Key offers a spacious, split floorplan, 1500 sq ft and is just 27 miles from Key West. The high quality 2010 construction features a hip metal roof, hardi plank siding, impact windows, and doors, ensuring durability and peace of mind. The heart of this home is its large kitchen, designed for both function and style. With an abundance of

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 822-7622

  27417 Tobago Ln, Ramrod 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

  Last Listing Agent Krystal Thomas eXp Realty LLC

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

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
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  /43

  $949,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  25057 7th St, Summerland Key, FL 33042

  Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the added bonus of a natural windbreak and guaranteed

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (786) 869-2251

  25057 7th St, 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 $245,086

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

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  0 Crane Blvd, Sugarloaf Key, FL 33042

  0 Crane Blvd, Sugarloaf Key, FL 33042
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  /31

  $750,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  27448 Haiti Ln, Summerland Key, FL 33042

  Welcome to 27438 Haiti Ln, Ramrod Key, a canal-front retreat offering the ultimate Florida Keys lifestyle. Situated on a peaceful canal with convenient boating access, this property is ideal for water lovers and those seeking a relaxing island escape. A cargo lift makes transporting supplies effortless, and additional storage ensures plenty of room for all your gear.Start your mornings on the

  

  Brenda Thomas

  Island Welcome Real Estate

  (888) 488-3424

  27448 Haiti Ln, Summerland Key, FL 33042
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  /57

  $2,800,000 Sold Oct 30, 2025

  22967 Redfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $747/SF
  • 37 Days On Market

  Current Estimated Value $2,811,102

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

  22967 Redfish Ln, Cudjoe Key, FL 33042
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  /2

  Est $650,181 Not Listed For Sale

  • Studio

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042
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  /38

  $1,499,000

  • 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 Lower Keys (KW)

  (786) 551-4933

  51 Drost Dr, Summerland Key, FL 33042
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  /25

  $310,000 Sold Mar 13, 2025

  28232 Dorothy Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $291/SF
  • 49 Days On Market

  Last Listing Agent Lanny Gardner Bluescape Real Estate

  28232 Dorothy Ave, Summerland Key, FL 33042
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  /2

  Est $512,243 Not Listed For Sale

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

  390 W Indies Dr, Ramrod Key, FL 33042

  390 W Indies Dr, Ramrod Key, FL 33042
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  /43

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  51 Sawyer Dr, Summerland Key, FL 33042

  Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 970-3222

  51 Sawyer 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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  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042
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  /55

  $2,300,000

  • 3 Beds
  • 3 Baths
  • 2,010 Sq Ft

  948 Gulf Dr, Summerland Key, FL 33042

  Luxury coastal living meets unmatched boating convenience at this fully renovated canal-front stunner in prestigious Summerland Cove Islands. Situated on a 7,575 sq ft lot with 75 ft of concrete dockage, a 20K lb boat lift, and quick ocean access via wide, flow-through canals -- this 3 Bedroom, 3 Bathroom home is a dream for boating enthusiasts. Inside, this 2,010 sq ft two-story retreat

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 833-9579

  948 Gulf Dr, Summerland Key, FL 33042
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  /2

  $55,000 Sold Jun 02, 2025

  0 Canal Dr, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 11% Below List Price
  • 32 Days On Market

  Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC

  0 Canal Dr, Sugarloaf Key, FL 33042
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  /2

  Est $219,242 Not Listed For Sale

  • Studio

  951 Hawksbill Ln, Sugarloaf Key, FL 33042

  951 Hawksbill Ln, Sugarloaf Key, FL 33042
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  /50

  $1,600,000

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

  947 Gulf Dr, Summerland Key, FL 33042

  There's a certain feeling you get the moment you pull onto Summerland Cove Isle, quiet, breezy, and unmistakably upscale. The kind of street where every home has been cared for, every canal sparkles, and the water itself seems to move with purpose. This home sits on the most coveted stretch of the island, where the flow-through, crystal-clear, extra-deep canals are the heartbeat of the

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 983-9115

  947 Gulf Dr, Summerland Key, FL 33042
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  /14

  $250,000 Sold Feb 24, 2025

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 6,725 Sq Ft
  • Built 1975

  Last Sold Summary

  • $37/SF
  • 7 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  1639 Pine Channel Dr, Little Torch Key, FL 33042
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  /8

  Est $433,069 Not Listed For Sale

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042
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  /4

  $285,000

  • Land

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 876-6382

  Unlisted Address
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  /29

  $395,000 Sold May 19, 2025

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 5% Below List Price
  • 78 Days On Market

  Current Estimated Value $392,764

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  430 Les Rohde Dr, Ramrod Key, FL 33042

  430 Les Rohde Dr, Ramrod Key, FL 33042
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  /77

  $12,999,999

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  /2

  $255,000 Sold Oct 20, 2025

  150 Coral Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1993

  Last Sold Summary

  • $232/SF
  • 0 Days On Market

  Current Estimated Value $457,000

  Last Listing Agent Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  150 Coral Ave, Summerland Key, FL 33042
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  /2

  Est $544,100 Not Listed For Sale

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  20874 4th Ave, Cudjoe Key, FL 33042
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  /49

  $1,145,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  22737 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

  

  Terry Garcia

  Keller Williams Key West Compass Realty

  (786) 321-8407

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
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  /51

  $420,000 Sold Nov 21, 2025

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 185 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042
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  /52

  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  21250 Conch Dr, Summerland Key, FL 33042

  Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 614-3802

  21250 Conch Dr, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18