Homes in ZIP Code 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 $601,827

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  19616 Aztec St, Summerland Key, FL 33042
• 

  

  

  /27

  Est $2,038,538

  Not Listed For Sale

  17022 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1994

  17022 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 85 Days On Market
• 

  

  

  /46

  $759,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  19543 Navajo St, Cudjoe Key, FL 33042

  3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

  Pamela Stangler Expert Realty LLC

  19543 Navajo St, Cudjoe Key, FL 33042
• 

  

  

  /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 $2,110,909

  Last Listing Agent Jonathan Minerick Homecoin.com

  441 Airport Dr N, Summerland Key, FL 33042
• 

  

  /2

  Est $1,317,263

  Not Listed For Sale

  23047 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft
  • Built 1991

  23047 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /6

  $1,775,000

  • 4 Beds
  • 4 Baths
  • 1,671 Sq Ft

  193 Galleon Ln, Cudjoe Key, FL 33042

  Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

  Joaquin Merlo-Garzon CRANELUXE

  193 Galleon Ln, Cudjoe Key, FL 33042
• 

  

  /36

  $840,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $976/SF
  • 159 Days On Market

  Last Listing Agent Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
• 

  

  /20

  Est $842,212

  Not Listed For Sale

  27370 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1992

  27370 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 118 Days On Market
• 

  

  /48

  $1,399,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  22939 Gasparilla Ln, Summerland Key, FL 33042

  Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete

  Donna Pezzi Keller Williams Key West Compass Realty

  22939 Gasparilla Ln, Summerland Key, FL 33042
• 

  

  /90

  $1,075,000

  Sold May 11, 2026

  21855 Spain Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $733/SF
  • 28 Days On Market

  Current Estimated Value $988,193

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  21855 Spain Blvd, Summerland Key, FL 33042
• 

  

  /49

  Est $1,765,161

  Not Listed For Sale

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft
  • Built 1989

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 80 Days On Market
• 

  

  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
• 

  

  /58

  $1,164,000

  Sold Dec 12, 2025

  164 Tortuga Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $831/SF
  • 27 Days On Market

  Current Estimated Value $1,201,382

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  164 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $1,705,158

  Not Listed For Sale

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 1963

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  Last Sold Summary

  • 275 Days On Market
• 

  

  /94

  $3,300,000

  $200K PRICE DROP Under Contract

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe.Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and

  Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
• 

  

  /48

  $352,000

  Sold Mar 16, 2026

  27945 Tarpon Terrace, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $405/SF
  • 91 Days On Market

  Last Listing Agent Anne Press Lokation Real Estate

  27945 Tarpon Terrace, Little Torch Key, FL 33042
• 

  /2

  Est $1,186,142

  Not Listed For Sale

  19563 Canal Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 1990

  19563 Canal Dr, Summerland Key, FL 33042
• 

  

  /52

  $749,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  629 Powell Ave, Summerland Key, FL 33042

  Welcome to 629 Powell Drive in Little Torch Key, the lowest-priced fully stilted CBS home currently available in the Lower Florida Keys. This elevated 2-bedroom, 1-bath canal-front home offers the ideal combination of affordability, boating access, and island living. Built for peace of mind, the home features a 2018 metal roof, accordion shutters on the doors, and panel shutters for the windows.

  Coby Taylor Expert Realty LLC (HQ)

  629 Powell Ave, Summerland Key, FL 33042
• 

  

  /32

  $970,000

  Sold Jul 08, 2026

  17287 Cayman Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Below List Price
  • $652/SF
  • 42 Days On Market

  Current Estimated Value $1,042,901

  Last Listing Agent Jonathan Minerick Homecoin.com

  17287 Cayman Dr, Summerland Key, FL 33042
• 

  

  /56

  Est $1,722,654

  Not Listed For Sale

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  17159 Amberjack Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 258 Days On Market
• 

  

  /7

  $4,375,000

  New Construction $100K PRICE INCREASE Pending

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

  231 E Shore Dr Unit 4, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 4, Summerland Key, FL 33042
• 

  /2

  $1,650,000

  Sold Sep 03, 2025

  743 E Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $944/SF
  • 1 Day On Market

  Current Estimated Value $2,138,608

  Last Listing Agent Scott Brisson KeyIsle Realty

  743 E Shore Dr, Summerland Key, FL 33042
• 

  

  /29

  Est $907,190

  Not Listed For Sale

  27359 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  27359 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 33 Days On Market
• 

  

  /47

  $1,200,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  637 Caribbean Dr E, Summerland Key, FL 33042

  Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromatic palette, the interiors feel fresh, cohesive, and effortlessly sophisticated--ready for you to start living the Keys lifestyle. Step outside to a relaxing porch overlooking a 60' wide, crystal-clear flow-through canal--perfect

  Donna Pezzi Keller Williams Key West Compass Realty

  637 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /11

  $475,000

  Sold May 27, 2026

  19264 Acosta Trail, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 832 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $571/SF
  • 9 Days On Market

  Current Estimated Value $483,690

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  19264 Acosta Trail, Summerland Key, FL 33042
• 

  

  /39

  Est $1,282,196

  Not Listed For Sale

  591 Blackbeard Rd, Summerland Key, FL 33042

  • 4 Beds
  • 4.5 Baths
  • 2,512 Sq Ft
  • Built 1989

  591 Blackbeard Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 25 Days On Market
• 

  

  /15

  $895,000

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

  135 Tortuga Ln, Summerland Key, FL 33042

  Waterfront living meets peace of mind in this exceptionally well-maintained canal-front home offering direct boating access to the Atlantic Ocean. Designed for the Florida Keys lifestyle, this property features a 60-foot dock with ample space for your boat and easy access to world-class fishing, diving, and cruising. Imagine being just a 30 minute drive from either the conveniences of Marathon or

  Kathleen Reed Bruno Realty Group, Inc

  135 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /4

  $700,000

  Sold Apr 23, 2026

  20963 7th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $450/SF

  Current Estimated Value $902,229

  Last Listing Agent Wyelda Bierman Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  20963 7th Ave W, Summerland Key, FL 33042
• 

  

  /31

  Est $746,588

  Not Listed For Sale

  4245 Egret Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2002

  4245 Egret Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 34 Days On Market
• 

  

  /64

  $1,800,000

  $190K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  3127 Stewart Rd, Summerland Key, FL 33042

  Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

  Pamela Stangler Expert Realty LLC

  3127 Stewart Rd, Summerland Key, FL 33042
• 

  

  /39

  $1,300,000

  Sold Jun 05, 2026

  20838 5th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1987

  Last Sold Summary

  • 19% Below List Price
  • $669/SF
  • 187 Days On Market

  Current Estimated Value $1,443,071

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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

  

  /82

  Est $1,849,994

  Not Listed For Sale

  17175 Allamanda Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 1999

  17175 Allamanda Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 19 Days On Market
• 

  

  /3

  $300,000

  • Land
  • 13.67 Acres
  • $21,946 per Acre

  0 Candice Ave, Little Torch Key, FL 33042

  Rare opportunity to acquire a 6-parcel assemblage totaling approx. 13.67 acres on Little Torch Key. Includes five 6,000 sq. ft. Mates Beach lots on Candice Avenue (two Tier 3 Infill) and a 12.97+/- acre tract with 2.61 acres upland and 10.36 acres environmentally sensitive land. Perfect for agricultural or beekeeping use, conservation project, or long-term investment. Located in a desirable Lower

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  0 Candice Ave, Little Torch Key, FL 33042
• 

  

  /32

  $670,000

  Sold Jun 15, 2026

  27999 Lobster Tail Trail, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $570/SF
  • 148 Days On Market

  Current Estimated Value $692,165

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  27999 Lobster Tail Trail, Little Torch Key, FL 33042
• 

  

  /29

  Est $873,387

  Not Listed For Sale

  22774 Cudjoe Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 1987

  22774 Cudjoe Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 44 Days On Market
• 

  

  /31

  $998,000

  $57K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  83 Sugarloaf Dr, Summerland Key, FL 33042

  Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  83 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /27

  $853,000

  Sold Jan 09, 2026

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • Built 2012

  Last Sold Summary

  • 14% Below List Price
  • $714/SF
  • 105 Days On Market

  Current Estimated Value $883,448

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22922 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /23

  Est $718,514

  Not Listed For Sale

  283 Pirates Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1964

  283 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 148 Days On Market
• 

  

  /4

  $100,000

  Pending

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042

  Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
• 

  

  /18

  $415,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  • Land
  • 2,178 Sq Ft
  • $8,300,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 228 Days On Market

  Current Estimated Value $442,778

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

Showing Results 441 - 480, Page 12 of 18