Homes in ZIP Code 33042

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  /16

  Est $1,880,803 Not Listed For Sale

  23076 Tarpon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1975

  23076 Tarpon Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 10% Above List Price
  • $1,872/SF
  • 82 Days On Market

  Last Sold Price $2,100,000

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys
• 

  

  

  /41

  $790,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Unlock Instant Equity on this Waterfront Gem waiting for restoration! Rare opportunity to own a waterfront escape at an unbeatable price point. This diamond in the rough is priced strictly for its condition, allowing you to build custom equity from day one. With a solid foundation and a backyard leading straight to the water's edge, this is the ultimate project for a savvy investor or visionary

  Jeff Shapiro Global Luxury Realty LLC

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  

  /30

  $710,000 Sold Dec 01, 2025

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2002

  Last Sold Summary

  • 25% Below List Price
  • $822/SF
  • 328 Days On Market

  Last Listing Agent Katrina Vanek Bluescape Real Estate

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
• 

  

  

  /27

  Est $1,586,581 Not Listed For Sale

  23092 Snapper Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Built 1985

  23092 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $957/SF
  • 7 Days On Market

  Last Sold Price $1,575,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  

  /33

  $255,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  

  /34

  $735,000 Sold May 16, 2025

  27373 Anguila Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $682/SF
  • 117 Days On Market

  Current Estimated Value $753,713

  Last Listing Agent Tracy Shields KeyIsle Realty

  27373 Anguila Ln, Summerland Key, FL 33042
• 

  

  /42

  Est $1,269,952 Not Listed For Sale

  1172 Coates Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft
  • Built 2002

  1172 Coates Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 5% Below List Price
  • $747/SF
  • 138 Days On Market

  Last Sold Price $1,340,000

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

  

  /45

  $519,000

  • 2 Beds
  • 2 Baths
  • 758 Sq Ft

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

  MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
• 

  

  /38

  $1,170,000 Sold Mar 02, 2026

  218 Spanish Main Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $580/SF
  • 11 Days On Market

  Current Estimated Value $1,184,579

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  218 Spanish Main Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,198,774 Not Listed For Sale

  22943 Dirk Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • Built 1998

  22943 Dirk Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Below List Price
  • $798/SF

  Last Sold Price $1,275,000

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)
• 

  

  /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
• 

  

  /92

  $1,050,000 Sold May 14, 2025

  27436 Tobago Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 2020

  Last Sold Summary

  • 19% Below List Price
  • $852/SF
  • 129 Days On Market

  Current Estimated Value $1,043,515

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  27436 Tobago Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,019,359 Not Listed For Sale

  22973 Anne Bonny Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft
  • Built 1988

  22973 Anne Bonny Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 36% Below List Price
  • $756/SF

  Last Sold Price $750,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /94

  $3,500,000

  • 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
• 

  

  /70

  $721,000 Sold Jun 03, 2025

  22933 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1995

  Last Sold Summary

  • 18% Below List Price
  • $663/SF
  • 74 Days On Market

  Current Estimated Value $766,007

  Last Listing Agent Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
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  /44

  Est $741,535 Not Listed For Sale

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1972

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Above List Price
  • $595/SF
  • 108 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Monique Thiel Sunshine State Realty Services
• 

  

  /7

  $4,375,000 New Construction

  • 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
• 

  

  /47

  $350,000 Sold Aug 14, 2025

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 675 Sq Ft
  • Built 1984

  Last Sold Summary

  • 22% Below List Price
  • $519/SF
  • 228 Days On Market

  Last Listing Agent Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042
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  /2

  Est $792,620 Not Listed For Sale

  201 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1983

  201 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Below List Price
  • $724/SF

  Last Sold Price $765,000

  Last Listing Agent Mark Peterson
• 

  

  /4

  $179,000

  • Land

  0 Park Dr Unit Bk 3 Lt 7, Summerland Key, FL 33042

  Exceptional corner lot opportunity in a sought-after Florida Keys neighborhood with a private airstrip. This Tier III parcel offers added flexibility in design and access, making it an ideal site for a custom home or strategic investment.PositPrime opportunity to build in one of the Florida Keys' most unique and desirable neighborhoods featuring a private airstrip. This Tier III vacant lot offers

  Natallie Liz Expert Realty LLC (HQ)

  0 Park Dr Unit Bk 3 Lt 7, Summerland Key, FL 33042
• 

  

  /44

  $870,000 Sold Feb 05, 2026

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 779 Sq Ft
  • Built 2005

  Last Sold Summary

  • 13% Below List Price
  • $1,117/SF
  • 224 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
• 

  

  /45

  Est $1,215,642 Not Listed For Sale

  22820 Blackbeard Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1989

  22820 Blackbeard Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $863/SF
  • 3 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Jamie Caudill Lokation Real Estate
• 

  

  /19

  $615,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  27147 Dolphin Rd, Summerland Key, FL 33042

  Priced to sell and being sold ASIS Walk to Boondocks Grille & Draft House! Located on Ramrod Key's Gulf side, this well-maintained 3-bedroom, 2-bath stilted home sits on an oversized 8,400 sq ft fenced lot at the end of a quiet cul-de-sac--no through traffic, just privacy and peace.The interior features a functional, comfortable layout with sliding glass doors opening to an inviting deck, ideal

  Robin Nilsson Keller Williams Key West Compass Realty

  27147 Dolphin Rd, Summerland Key, FL 33042
• 

  

  /37

  $765,000 Sold Jul 28, 2025

  27255 Mariposa Rd, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $531/SF
  • 113 Days On Market

  Current Estimated Value $786,824

  Last Listing Agent Melissa Graham Bluescape Real Estate

  27255 Mariposa Rd, Ramrod Key, FL 33042
• 

  

  /47

  Est $2,259,209 Not Listed For Sale

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1977

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Below List Price
  • $1,347/SF
  • 17 Days On Market

  Last Sold Price $2,450,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /64

  $1,900,000

  • 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
• 

  

  /15

  $245,000 Sold Feb 17, 2026

  27345 Guadaloupe Ln, Ramrod Key, FL 33042

  • Land

  Last Sold Summary

  • 19% Below List Price
  • 56 Days On Market

  Current Estimated Value $282,004

  Last Listing Agent Scott Brisson KeyIsle Realty

  27345 Guadaloupe Ln, Ramrod Key, FL 33042
• 

  

  /60

  Est $936,788 Not Listed For Sale

  52 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1988

  52 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $636/SF
  • 58 Days On Market

  Last Sold Price $885,000

  Last Listing Agent Pamela Stangler Expert Realty LLC
• 

  

  /3

  $300,000

  • Land

  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
• 

  

  /38

  $785,000 Sold Nov 04, 2025

  22464 La Fitte Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $913/SF
  • 41 Days On Market

  Current Estimated Value $773,228

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  22464 La Fitte Dr, Summerland Key, FL 33042
• 

  

  /34

  Est $775,837 Not Listed For Sale

  191 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1963

  191 Doubloon Ln, Summerland Key, FL 33042

  Last Sold Summary

  • $578/SF
  • 10 Days On Market

  Last Sold Price $775,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /94

  $3,875,000

  • 4 Beds
  • 4 Baths
  • 2,766 Sq Ft

  414 Caribbean Dr E, Summerland Key, FL 33042

  Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft.

  Lisa Swanson The Agency Florida Keys

  414 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  $49,000 Sold Jun 06, 2025

  Lot 7 Block 14, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 29% Below List Price
  • 163 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 7 Block 14, Cudjoe Key, FL 33042
• 

  

  /77

  Est $5,872,168 Not Listed For Sale

  200 Erie Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 4,514 Sq Ft
  • Built 2002

  200 Erie Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 11% Below List Price
  • $1,468/SF
  • 295 Days On Market

  Last Sold Price $6,625,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /31

  $1,055,000

  • 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
• 

  

  /17

  $577,500 Sold Feb 10, 2026

  56 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 2000

  Last Sold Summary

  • 26% Below List Price
  • $418/SF
  • 53 Days On Market

  Current Estimated Value $627,554

  Last Listing Agent Veronica Crego-Flores

  56 W Shore Dr, Summerland Key, FL 33042
• 

  

  /41

  Est $1,395,564 Not Listed For Sale

  20785 5th Ave W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1990

  20785 5th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $917/SF
  • 77 Days On Market

  Last Sold Price $1,375,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /4

  $100,000

  • 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
• 

  

  /8

  $750,000 Sold Feb 06, 2026

  24931 Overseas Hwy, Summerland Key, FL 33042

  • 1 Bed
  • 4 Baths
  • 1,965 Sq Ft
  • Built 1975

  Last Sold Summary

  • 42% Below List Price
  • $382/SF
  • 309 Days On Market

  Current Estimated Value $1,118,973

  Last Listing Agent Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  24931 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /45

  Est $1,356,582 Not Listed For Sale

  622 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3.5 Baths
  • 2,156 Sq Ft
  • Built 1986

  622 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 46% Below List Price
  • $1,169/SF
  • 156 Days On Market

  Last Sold Price $2,520,000

  Last Listing Agent Laura Derrickson Keller Williams Coastal Partners

Showing Results 521 - 560, Page 14 of 18