Summerland Key, FL Homes

• 

  

  

  /27

  Est $248,869

  Not Listed For Sale

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  • 1 Bed
  • Built 1974

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  Last Sold Summary

  • 161 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate
• 

  

  

  /71

  $2,795,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,913 Sq Ft

  20920 5th Ave W, Summerland Key, FL 33042

  Florida Keys luxury island living at its finest.Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

  

  Miriam Novotny

  Compass Florida, LLC

  20920 5th Ave W, Summerland Key, FL 33042
• 

  

  

  /34

  $600,000

  Sold Sep 22, 2025

  19557 Mayan St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $607/SF
  • 186 Days On Market

  Current Estimated Value $627,743

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, 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

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty
• 

  

  

  /70

  $2,800,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,286 Sq Ft

  21640 Overseas Hwy, Summerland Key, FL 33042

  SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  21640 Overseas Hwy, Summerland Key, FL 33042
• 

  /2

  $48,000

  Sold Mar 13, 2026

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 26% Below List Price
  • 250 Days On Market

  Current Estimated Value $50,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
• 

  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
• 

  

  /52

  $699,000

  $50K PRICE DROP Under Contract

  • 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
• 

  

  /64

  $815,422

  Sold Nov 06, 2025

  554 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • Built 1963

  Last Sold Summary

  • 9% Below List Price
  • $580/SF
  • 34 Days On Market

  Current Estimated Value $916,582

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  554 W Shore Dr, Summerland Key, FL 33042
• 

  

  /33

  Est $887,577

  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

  Last Listing Agent Natallie Liz Expert Realty LLC (HQ)
• 

  

  /40

  $869,500

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  31364 Avenue J, Big Pine Key, FL 33043

  Boating and open-water views await! This Big Pine Key property offers unobstructed water views along with 150 ft. of concrete seawall, protected dockage, and plenty of potential for the buyer who's ready to add some TLC. The spacious 1,291 sq. ft. living area features beautiful water views from the front porch, great room, and main bedroom. A screened porch and open deck overlook the canal that

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  31364 Avenue J, Big Pine Key, FL 33043
• 

  

  /66

  $1,715,000

  Sold Jul 31, 2026

  30985 Watson Blvd, Big Pine Key, FL 33043

  • 4 Beds
  • 3.5 Baths
  • 2,639 Sq Ft
  • Built 2022

  Last Sold Summary

  • $650/SF
  • 0 Days On Market

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  30985 Watson Blvd, Big Pine Key, FL 33043
• 

  /2

  Est $1,196,613

  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
• 

  

  /48

  $899,000

  $51K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  29114 Cedar Dr, Big Pine Key, FL 33043

  Extra adjoining lot adds additional seawall frontage and provides plenty of room for a pool, extra recreational space, and additional parking at this beautifully updated waterfront property in Big Pine Key. This well-maintained home features impact-resistant windows and doors, along with a tranquil canal-side screened porch that creates the perfect setting to relax and enjoy the Florida Keys

  

  Lynn Goodwin

  Coldwell Banker Schmitt Real Estate Co.

  29114 Cedar Dr, Big Pine Key, FL 33043
• 

  

  /71

  $3,150,000

  Sold Aug 28, 2025

  225 Colson Dr, Summerland Key, FL 33042

  • 6 Beds
  • 6.5 Baths
  • 4,976 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $633/SF
  • 118 Days On Market

  Current Estimated Value $3,342,758

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  225 Colson Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $230,434

  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

  Last Listing Agent Mary Conklin Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
• 

  

  /57

  $2,200,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  1631 Sunrise Dr, Big Pine Key, FL 33043

  Experience the pinnacle of Florida Keys waterfront living in this newly constructed (2023) open water home on Big Pine Key. Perfectly positioned to capture breathtaking sunrise views, this CBS-built residence offers a seamless blend of modern coastal design, durability, and effortless indoor-outdoor living. Spanning 1,834 square feet, the home features 3 Bedrooms and 2 Bathrooms, thoughtfully

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  1631 Sunrise Dr, Big Pine Key, FL 33043
• 

  

  /20

  $207,000

  Sold Apr 09, 2026

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  • Land
  • 1,742 Sq Ft
  • $5,175,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 375 Days On Market

  Current Estimated Value $208,609

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
• 

  /2

  Est $1,019,514

  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
• 

  

  /36

  $750,000

  • Land
  • 9.26 Acres
  • $80,995 per Acre

  0 Niles Rd, Summerland Key, FL 33042

  Prime residential lot opportunity in Key Colony Beach, Monroe County, located at 0 Niles Rd, Key Colony, FL 33042.This approximately 9.2-acre property is situated in the Florida Keys with convenient access to nearby points of interest including Murray's Market (0.45 miles), Big Pine Key Boat Rentals (0.6 miles), Merrill Homes Inc (0.6 miles), and WWUS-FM Big Pine Key (1.85 miles). The lot

  

  Javier Santana

  Sunland Real Estate, LLC.

  0 Niles Rd, Summerland Key, FL 33042
• 

  $50,000

  Sold May 07, 2026

  13 Yuca Ln, Torch Key, FL 33042

  • Land
  • 5,000 Sq Ft
  • $435,540 per Acre

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Regine Mercier The Keyes Company

  13 Yuca Ln, 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

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
• 

  

  /16

  $549,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042

  Canal-front Paradise Awaits! Incredible view from your back deck!Unit 424 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile homenestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042
• 

  

  /43

  $1,150,000

  Sold Sep 22, 2025

  1032 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1990

  Last Sold Summary

  • 18% Below List Price
  • $833/SF
  • 175 Days On Market

  Current Estimated Value $1,184,520

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland 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
• 

  

  /52

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  29534 Geraldine St, Big Pine Key, FL 33043

  Turnkey and move-in ready, this exceptional waterfront home is being offered fully furnished--including furniture, dishes, cookware, and linens--so you can start enjoying the Florida Keys lifestyle from day one. Situated on an oversized 18,000 sq. ft. double lot with 150' of canal frontage in a quiet, peaceful Big Pine Key boating community, this solid concrete 3BD/2BA home features a desirable

  

  Sandra Tuttle

  Island Welcome Real Estate

  29534 Geraldine St, Big Pine Key, FL 33043
• 

  

  /28

  $465,000

  Sold Aug 25, 2026

  29757 Henry Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $373/SF
  • 96 Days On Market

  Last Listing Agent Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  29757 Henry Ln, Big Pine Key, FL 33043
• 

  

  /5

  Est $1,491,760

  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

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  

  /51

  $2,200,000

  $299K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  27348 Dominica Ln, Ramrod Key, FL 33042

  Welcome to your waterfront retreat on Ramrod Key, where beautiful open water views, quick ocean access, and exceptional outdoor living create the ultimate Florida Keys lifestyle. Built by renowned Tom Ryan in 2007, this well-maintained 3-bedroom, 2-bath home is designed for both relaxation and adventure. Step inside to a bright, open-concept living area featuring a spacious kitchen with ample

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  27348 Dominica Ln, Ramrod Key, FL 33042
• 

  

  /24

  $310,000

  Sold Apr 16, 2026

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

  • Land
  • 2,178 Sq Ft
  • $6,200,000 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 118 Days On Market

  Current Estimated Value $318,560

  Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 181, Cudjoe 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

  Last Listing Agent Jenna Stauffer Ocean Sotheby's International Realty
• 

  

  /46

  $799,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  30937 Baileys Ln, Big Pine Key, FL 33043

  It's your lucky day! The last buyers had to cancel their contract for personal reasons prior to inspections. Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story,

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  30937 Baileys Ln, Big Pine Key, FL 33043
• 

  

  /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 $742,544

  Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

  27235 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /33

  Est $942,308

  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

  Last Listing Agent David Kaufmann Century 21 Circle
• 

  

  /44

  $1,200,000

  Open Sat 11AM - 1PM

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

  17286 Jamaica Ln, Summerland Key, FL 33042

  Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  17286 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /58

  $625,000

  Sold Aug 10, 2026

  31147 Avenue H, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1996

  Last Sold Summary

  • 11% Below List Price
  • $651/SF
  • 96 Days On Market

  Current Estimated Value $640,590

  Last Listing Agent Jamie Caudill Lokation Real Estate

  31147 Avenue H, Big Pine Key, FL 33043
• 

  

  /49

  Est $877,836

  Not Listed For Sale

  29765 Osprey Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 1,456 Sq Ft
  • Built 1988

  29765 Osprey Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 52 Days On Market

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

  

  /54

  $949,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  22953 John Silver Ln, Summerland Key, FL 33042

  Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  22953 John Silver Ln, 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 $818,350

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
• 

  /2

  Est $255,518

  Not Listed For Sale

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  • Studio
  • Built 1981

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

Showing Results 121 - 160, Page 4 of 18