Summerland Key, FL Homes

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  /31

  $725,000

  Sold Jan 05, 2026

  27235 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $532/SF
  • 127 Days On Market

  Current Estimated Value $742,717

  Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

  27235 Mariposa Rd, Summerland Key, FL 33042
• 

  

  

  /16

  Not Listed For Sale

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  Last Sold Summary

  • 212 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
• 

  

  

  /43

  $1,025,000

  Sold Feb 11, 2026

  29039 Cedar Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $971/SF
  • 42 Days On Market

  Current Estimated Value $1,006,478

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  29039 Cedar Dr, Big Pine Key, FL 33043
• 

  

  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  Last Sold Summary
• 

  

  /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
• 

  

  /35

  $817,500

  Sold Dec 01, 2025

  22878 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $862/SF
  • 133 Days On Market

  Current Estimated Value $811,128

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
• 

  

  /32

  Est $470,798

  Not Listed For Sale

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  • 1 Bed
  • Built 1988

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  Last Sold Summary

  • 256 Days On Market
• 

  

  /71

  $607,000

  $13K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1258 Division St, Big Pine Key, FL 33043

  Welcome to Your Own Slice of Island Paradise in Big Pine Key! Tucked away in the heart of Big Pine, this picture-perfect 3-bedroom, 1-bath home invites you to slow down, breathe deep, & truly enjoy island living. Set on an oversized double lot totaling 12,500 sq ft, this property is truly a private tropical sanctuary: lush, peaceful, and full of life.From the moment you step inside, soaring beam

  

  Lindsay Ryan

  EXP Realty LLC

  (833) 721-7372

  1258 Division St, Big Pine Key, FL 33043
• 

  

  /83

  $3,300,000

  Sold Jul 11, 2025

  16705 Tamarind Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 3,086 Sq Ft
  • Built 2015

  Last Sold Summary

  • 27% Below List Price
  • $1,069/SF
  • 299 Days On Market

  Current Estimated Value $3,356,499

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

  16705 Tamarind Rd, Summerland Key, FL 33042
• 

  

  /30

  Not Listed For Sale

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

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

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

  Last Sold Summary

  • 176 Days On Market
• 

  

  /23

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft

  75 Lobstertail Rd, Big Pine Key, FL 33043

  Enjoy easy island living in this beautifully updated 2BD/2BA elevated home set along a peaceful plugged canal--perfect for paddleboarding and enjoying the waterfront ambiance (no boating access).Inside, the open living space features vaulted ceilings, luxury plank vinyl flooring throughout, and great natural light, flowing out to a screened porch overlooking the canal. The standout chef's kitchen

  

  Sandra Tuttle

  Island Welcome Real Estate

  (877) 375-6513

  75 Lobstertail Rd, Big Pine Key, FL 33043
• 

  

  /3

  $75,000

  Sold Oct 10, 2025

  0 Asturias Rd, Cudjoe Key, FL 33042

  • Land
  • 1.01 Acres
  • $74,124 per Acre

  Last Sold Summary

  • 62% Below List Price
  • 41 Days On Market

  Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

  0 Asturias Rd, Cudjoe Key, FL 33042
• 

  

  /33

  Est $909,233

  Not Listed For Sale

  28120 County Rd, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2024

  28120 County Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 74 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
• 

  /2

  $600,000

  Sold Jul 14, 2025

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1993

  Last Sold Summary

  • 14% Below List Price
  • $735/SF
  • 56 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
• 

  /2

  Est $1,195,103

  Not Listed For Sale

  17277 Dolphin St E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1995

  17277 Dolphin St E, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /47

  $698,800

  • 3 Beds
  • 2 Baths
  • 1,039 Sq Ft

  29048 Iris Dr, Big Pine Key, FL 33043

  50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water heater,

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (833) 968-8150

  29048 Iris Dr, Big Pine Key, FL 33043
• 

  

  /32

  $3,500

  Sold May 20, 2026

  29850 Journeys End Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1988

  Last Sold Summary

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

  Current Estimated Value $778,786

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  29850 Journeys End Rd, Big Pine Key, FL 33043
• 

  

  /14

  Est $221,657

  Not Listed For Sale

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 2000

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  Last Sold Summary

  • 246 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
• 

  

  /37

  $642,000

  Sold Jul 11, 2025

  31067 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $423/SF
  • 9 Days On Market

  Current Estimated Value $666,183

  Last Listing Agent Jared Chiagouris Truman & Co. (KW)

  31067 Avenue C, Big Pine Key, FL 33043
• 

  /2

  Est $1,030,687

  Not Listed For Sale

  421 W Indies, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  421 W Indies, Ramrod Key, FL 33042

  Last Sold Summary
• 

  

  /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
• 

  /2

  $49,000

  Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land
  • 5,499 Sq Ft
  • $388,080 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /19

  Not Listed For Sale

  31008 Avenue B, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 684 Sq Ft
  • Built 1973

  31008 Avenue B, Big Pine Key, FL 33043

  Last Sold Summary

  • 264 Days On Market
• 

  

  /36

  $665,000

  $53K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,497 Sq Ft

  30416 Coconut Hwy, Big Pine Key, FL 33043

  Looking for a lot of land in the Keys, and a well-maintained home? This rare 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV, boat trailers, so much more! Over 1⁄2 acre, the 4 lots are bordered by Coconut Hwy. to the north, Avenue B to the west, and Hibiscus Ln. to the south from which vehicles can access the large, fenced portion of the back yard. Step inside

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (888) 817-7679

  30416 Coconut Hwy, Big Pine Key, FL 33043
• 

  

  /3

  $420,000

  Sold Jun 27, 2025

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 488 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Below List Price
  • $861/SF
  • 0 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

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

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  Last Sold Summary
• 

  

  /41

  $550,000

  • 3 Beds
  • 1 Bath
  • 988 Sq Ft

  30372 Palm Dr, Big Pine Key, FL 33043

  Well-priced Keys living starts here! This 12,500 sq. ft. double lot offers ample parking and room to add a pool, garage, tiki hut, or more. In 2022, the current owner added a metal roof, impact-resistant windows and doors, and Mitsubishi mini-split A/C units. Inside, the home features a spacious great room, three bedrooms, one updated bath, and tile floors throughout. Outside, you'll find a solar

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (888) 376-2422

  30372 Palm Dr, Big Pine Key, FL 33043
• 

  

  /38

  $840,000

  Sold Sep 30, 2025

  3611 S Seas St, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $787/SF
  • 183 Days On Market

  Last Listing Agent Scott Brisson KeyIsle Realty

  3611 S Seas St, Big Pine Key, FL 33043
• 

  

  /5

  Est $1,495,930

  Not Listed For Sale

  354 Airport Dr S, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,881 Sq Ft
  • Built 2013

  354 Airport Dr S, Summerland Key, FL 33042

  Last Sold Summary

  • 2 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
• 

  

  /43

  $1,100,000

  Sold May 14, 2026

  1011 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $962/SF
  • 0 Days On Market

  Current Estimated Value $1,158,914

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1011 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /11

  Not Listed For Sale

  0 4th St Unit A&B 608914, Summerland Key, FL 33042

  0 4th St Unit A&B 608914, Summerland Key, FL 33042

  Last Sold Summary

  • 53 Days On Market
• 

  

  /27

  $1,055,000

  $110K PRICE DROP

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

  29051 Magnolia Ln, Big Pine Key, FL 33043

  Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers an exceptional opportunity to enjoy the relaxed Lower Florida Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with

  

  Yvette Toledo-Baste

  COMPASS FLORIDA LLC

  (855) 408-6871

  29051 Magnolia Ln, Big Pine Key, FL 33043
• 

  

  /70

  $1,290,000

  Sold May 19, 2026

  403 Indies Rd, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1991

  Last Sold Summary

  • 4% Below List Price
  • $960/SF
  • 63 Days On Market

  Current Estimated Value $1,302,214

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /33

  Est $683,548

  Not Listed For Sale

  30361 Harding Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 888 Sq Ft
  • Built 1963

  30361 Harding Rd, Big Pine Key, FL 33043

  Last Sold Summary

  • 295 Days On Market
• 

  

  /50

  $1,385,000

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  30830 Palm Dr, Big Pine Key, FL 33043

  Discover the perfect Florida Keys waterfront retreat in Big Pine Key. Situated on an oversized 16,779 sq ft lot on a quiet street away from the highway, this solidly built concrete block home with a concrete subfloor and stucco finish offers durability, privacy, and the laid-back island lifestyle buyers dream about.Boaters will appreciate 112 feet of concrete seawall, a 10,000 lb boat lift,

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (855) 640-6438

  30830 Palm Dr, Big Pine Key, FL 33043
• 

  

  /75

  $830,000

  Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $852,578

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18