Summerland Key, FL Homes

• 

  

  

  /47

  Est $2,670,306

  Not Listed For Sale

  27440 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,958 Sq Ft
  • Built 1982

  27440 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2 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
• 

  

  

  /57

  $1,550,000

  Sold Mar 02, 2026

  270 Airport Dr S, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,275 Sq Ft
  • Built 1980

  Last Sold Summary

  • 30% Below List Price
  • $1,216/SF
  • 63 Days On Market

  Current Estimated Value $1,525,661

  Last Listing Agent Solaris Gregory Expert Realty LLC (HQ)

  270 Airport Dr S, Summerland Key, FL 33042
• 

  

  

  /46

  Est $2,652,839

  Not Listed For Sale

  961 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,006 Sq Ft
  • Built 1998

  961 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 37 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
• 

  

  /60

  $930,000

  Sold May 01, 2026

  29182 Orchid Ln, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $452/SF
  • 41 Days On Market

  Current Estimated Value $929,142

  Last Listing Agent Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  29182 Orchid Ln, Big Pine Key, FL 33043
• 

  

  /40

  Est $1,118,338

  Not Listed For Sale

  791 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1982

  791 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 191 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
• 

  

  /29

  $235,000

  Sold Oct 31, 2025

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

  • Land
  • 2,078 Sq Ft
  • $4,926,179 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 76 Days On Market

  Current Estimated Value $252,576

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
• 

  

  /28

  Est $831,321

  Not Listed For Sale

  27378 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 925 Sq Ft
  • Built 1963

  27378 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 34 Days On Market
• 

  

  /19

  $799,000

  $51K PRICE DROP

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

  3922 Gordon Rd, Big Pine Key, FL 33043

  Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordon Road is an elevated 2BR/2BA waterfront retreat in Big Pine Key offering the lifestyle buyers come here for--easy boating, inviting outdoor living, and a home that feels like an escape from the moment you arrive. Bright coastal interiors, an open living/dining/kitchen layout, and a screened porch create a

  Dominic Paolillo Jr. Truman & Co. (KW)

  3922 Gordon Rd, Big Pine Key, FL 33043
• 

  

  /45

  $1,300,000

  Sold Mar 03, 2026

  1185 Hakluyt Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $1,128/SF
  • 10 Days On Market

  Current Estimated Value $1,304,754

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  1185 Hakluyt Ln, Summerland Key, FL 33042
• 

  

  /41

  Est $863,565

  Not Listed For Sale

  27468 Haiti Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1979

  27468 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6 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
• 

  

  /42

  $880,000

  Sold Jun 25, 2026

  27415 Barbuda Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 2008

  Last Sold Summary

  • 30% Below List Price
  • $625/SF
  • 375 Days On Market

  Current Estimated Value $1,023,284

  Last Listing Agent Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  27415 Barbuda Ln, Ramrod Key, FL 33042
• 

  

  /18

  Est $768,272

  Not Listed For Sale

  27438 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1987

  27438 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 146 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
• 

  /2

  $75,000

  Sold Jun 29, 2026

  Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

  • Land
  • 14,810 Sq Ft
  • $220,588 per Acre

  Last Sold Summary

  • 83% Below List Price
  • 346 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
• 

  

  /45

  Est $1,182,193

  Not Listed For Sale

  23058 Sailfish Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,280 Sq Ft
  • Built 1980

  23058 Sailfish Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 145 Days On Market
• 

  

  /4

  $2,499,000

  $251K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  32029 Marginella Dr, Big Pine Key, FL 33043

  Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stone's throw away from Big Pine Key, this nearly 2-acre property presents

  Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

  32029 Marginella Dr, Big Pine Key, FL 33043
• 

  

  /61

  $3,900,000

  Sold Feb 27, 2026

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $1,986/SF
  • 25 Days On Market

  Current Estimated Value $3,875,652

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042
• 

  

  /16

  Est $1,978,460

  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

  • 82 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
• 

  

  /36

  $685,000

  Sold Oct 15, 2025

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 2010

  Last Sold Summary

  • 16% Below List Price
  • $793/SF
  • 164 Days On Market

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

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
• 

  

  /27

  Est $1,668,474

  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

  • 7 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
• 

  

  /39

  $900,000

  Sold Jul 02, 2026

  21073 7th Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft
  • Built 1975

  Last Sold Summary

  • $409/SF
  • 0 Days On Market

  Current Estimated Value $1,311,857

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  21073 7th Ave, Summerland Key, FL 33042
• 

  

  /42

  Est $1,344,288

  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

  • 138 Days On Market
• 

  

  /38

  $1,390,000

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

  174 Tortuga Ln, Cudjoe Key, FL 33042

  Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Seller is in the process of permitting and

  Sarah Bixby eXp Realty LLC

  174 Tortuga Ln, Cudjoe Key, FL 33042
• 

  

  /51

  $990,000

  Sold Oct 28, 2025

  22841 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $516/SF
  • 139 Days On Market

  Current Estimated Value $1,099,290

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,290,902

  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
• 

  

  /28

  $520,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 812 Sq Ft

  29284 Coconut Palm Dr, Big Pine Key, FL 33043

  Escape to your own private tropical oasis in the heart of Big Pine Key. Hidden behind lush mature landscaping and swaying palms, this charming 2-bedroom, 1-bath home offers the privacy, tranquility, and island lifestyle that make the Lower Keys so desirable. The flood policy is $977 and assumable!! Situated on a 6,000-square-foot lot in the sought-after Eden Pines neighborhood, this concrete home

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  29284 Coconut Palm Dr, Big Pine Key, FL 33043
• 

  

  /7

  $1,600,000

  Sold Nov 21, 2025

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.37 Acres
  • $1,164,531 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 141 Days On Market

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /44

  Est $746,397

  Not Listed For Sale

  22903 Jolly Roger Dr, Summerland Key, FL 33042

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

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 108 Days On Market
• 

  

  /3

  $799,000

  $50K PRICE DROP Pending

  • Land
  • 10 Acres
  • $79,900 per Acre

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
• 

  

  /29

  $1,245,000

  Sold Jul 28, 2025

  17081 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $807/SF
  • 199 Days On Market

  Current Estimated Value $1,328,909

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  17081 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /70

  Est $777,646

  Not Listed For Sale

  22933 Buccaneer Ln, Summerland Key, FL 33042

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

  22933 Buccaneer Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 74 Days On Market
• 

  

  /49

  $1,295,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,861 Sq Ft

  1709 Sunrise Dr, Big Pine Key, FL 33043

  Wake up to endless ocean views, spectacular sunrises, and the unmatched waterfront lifestyle of the Florida Keys. Nestled on a rare 17,000-square-foot open-water lot in the highly sought-after Tropical Bay Estates, this beautifully renovated 3-bedroom, 2-bath residence offers the perfect blend of coastal charm, privacy, and effortless boating access. Designed to maximize its breathtaking

  Paige Bethel Island Home Realty Inc.

  1709 Sunrise Dr, Big Pine Key, FL 33043
• 

  

  /47

  $895,000

  Sold Dec 10, 2025

  22880 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $713/SF
  • 34 Days On Market

  Current Estimated Value $922,927

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
• 

  /2

  Est $833,095

  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

Showing Results 641 - 680, Page 17 of 18