Summerland Key, FL Homes

• 

  

  

  /27

  $1,055,000

  • 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
• 

  

  

  /12

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • House for Rent

  31167 Ave G, Big Pine Key, FL 33043

  Property Id: 2043505If your between homes, or construction, or here for a shorter period, here is a fully furnished home. Available now, 6mos + few days rental. Nice spacious, furnished home on a double lot, with fenced back yard. Utilities not included. Above ground pool. Close to local amenities. 3bd/2bth 1528 sq. ft. home with laundry room. Central AC & Heat. Monthly yard care

  31167 Ave G, Big Pine Key, FL 33043
• 

  

  

  /16

  $1,400,000 Sold Mar 16, 2026

  570 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $933/SF
  • 14 Days On Market

  Current Estimated Value $1,427,000

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  570 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  

  /20

  Not Listed For Sale

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 80 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Tylon Fraley Southeast Realty Equities, Inc
• 

  

  

  /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, and

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (855) 640-6438

  30830 Palm Dr, Big Pine Key, FL 33043
• 

  

  /13

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • House for Rent

  1540 Lantana Ln, Big Pine Key, FL 33043

  Fishermans Dream House!Bring your boats to this beautiful canal front home in Big Pine Key. Secluded on a corner lot with 190 ft of seawall. Boat ramp is less than a mile away. Enjoy swimming in the pool, relaxing on the deck, cocktails at the outside bar, or meeting the adorable friendly Key Deer roaming the neighborhood.Sleeps 8Available February 1st for monthly rentalCall

  Andrea Lennon Vylla Home

  1540 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /45

  $780,000 Sold Jul 18, 2025

  29025 Geranium Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $855/SF
  • 44 Days On Market

  Current Estimated Value $796,821

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  29025 Geranium Dr, Big Pine Key, FL 33043
• 

  

  /50

  Est $862,290 Not Listed For Sale

  489 Pirates Rd, Little Torch Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,638 Sq Ft
  • Built 1984

  489 Pirates Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 1% Below List Price
  • $534/SF
  • 38 Days On Market

  Last Sold Price $875,000

  Last Listing Agent Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /43

  $888,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  25057 7th St, Summerland Key, FL 33042

  Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the added bonus of a natural windbreak and guaranteed

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (786) 869-2251

  25057 7th St, Summerland Key, FL 33042
• 

  

  /13

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,109 Sq Ft
  • House for Rent

  26945 Shannahan Rd, Summerland Key, FL 33042

  Property Id: 24239533 Bd/2 Bth Concrete block home. Central A/C with heat. Granite counter tops in kitchen. Fridge, Gas Stove, dishwasher and central ac. Stackable washer/dryer. Fenced back yard. Concrete patio in front or parking area. In Ramrod Key. Non waterfront. No house on either side. Must have good credit and references and income will be verified. Utilities NOT included. Rent

  26945 Shannahan Rd, Summerland Key, FL 33042
• 

  

  /49

  $650,000 Sold Aug 20, 2025

  27317 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,029 Sq Ft
  • Built 2012

  Last Sold Summary

  • 28% Below List Price
  • $632/SF
  • 262 Days On Market

  Current Estimated Value $682,846

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

  27317 Cayman Ln, Summerland Key, FL 33042
• 

  

  /35

  Est $237,051 Not Listed For Sale

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  Last Sold Summary

  • 9% Above List Price
  • 22 Days On Market

  Last Sold Price $217,000

  Last Listing Agent Kelly Gardner Bluescape Real Estate
• 

  

  /31

  $725,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  27448 Haiti Ln, Ramrod Key, FL 33042

  Claim your slice of paradise and build the waterfront setup you've always wanted. Welcome to 27438 Haiti Ln, a deep-water canal-front blank canvas on Ramrod Key designed for the serious angler. This isn't just a home; it's the ultimate staging ground for your offshore and backcountry adventures.The highlight? A pristine shoreline ready for you to design and permit your dream dock. Whether you

  

  Brenda Thomas

  Island Welcome Real Estate

  (645) 225-2680

  27448 Haiti Ln, Ramrod Key, FL 33042
• 

  

  /13

  $5,538 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28513 Channel View Dr, Little Torch Key, FL 33042

  This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished or furnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour

  Joseph Danieli AKT Realty LLC

  28513 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /59

  $860,300 Sold May 02, 2025

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $996/SF
  • 76 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
• 

  

  /51

  Not Listed For Sale

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2006

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  Last Sold Summary

  • $899/SF
  • 27 Days On Market

  Last Sold Price $777,000

  Last Listing Agent Kelly Gardner Bluescape Real Estate
• 

  

  /30

  $975,000

  • 3 Beds
  • 3 Baths
  • 1,492 Sq Ft

  31490 Avenue F, Big Pine Key, FL 33043

  This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and functionality. Featuring impact windows and doors and a durable metal roof, this home provides peace of mind and protection for years to come. The open-concept living area is perfect for both relaxation and entertaining, with a modern kitchen boasting quartz countertops and stainless steel appliances. The

  

  Austin Kimbler

  Expert Realty LLC (HQ)

  (833) 691-1620

  31490 Avenue F, Big Pine Key, FL 33043
• 

  

  /49

  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  3770 Park Ave, Big Pine Key, FL 33043

  Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

  Mary Jo Selden DomainRealty.com LLC

  3770 Park Ave, Big Pine Key, FL 33043
• 

  

  /5

  $725,000 Sold Jul 30, 2025

  19462 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $520/SF
  • 3 Days On Market

  Current Estimated Value $723,420

  Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

  19462 Canal Dr, Summerland Key, FL 33042
• 

  

  /9

  Not Listed For Sale

  Lots 23-24 Coral Way, Big Pine Key, FL 33043

  Lots 23-24 Coral Way, Big Pine Key, FL 33043

  Last Sold Summary

  • 24 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
• 

  

  /22

  $714,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  4039 Egret Ln, Summerland Key, FL 33042

  Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 238-9391

  4039 Egret Ln, Summerland Key, FL 33042
• 

  

  /14

  $3,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28534 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 4/30/26.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna, marina

  Joseph Danieli AKT Realty LLC

  28534 Channel View Dr, Little Torch Key, FL 33042
• 

  /2

  $55,000 Sold Oct 22, 2025

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /6

  Not Listed For Sale

  3 Rd Ave Unit 1, Big Pine Key, FL 33043

  3 Rd Ave Unit 1, Big Pine Key, FL 33043

  Last Sold Summary

  • 20 Days On Market

  Last Sold Price $162,000

  Last Listing Agent Benjamin Daniels Lokation Real Estate
• 

  

  /44

  $1,199,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  30329 Heron Ln, Big Pine Key, FL 33043

  Nature Lover's Waterfront Retreat on a Rare Double Canal Lot. Imagine living where the sky blazes with sunsets over a pristine bird sanctuary and gentle Key Deer roam freely through your yard. Welcome to 30329 Heron Lane, a beautifully maintained 3 bedroom, 2 bathroom elevated Conch Cottage perched on a 15,438 sq ft double corner canal lot with 268' of waterfront in Big Pine Key. From the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (866) 665-8962

  30329 Heron Ln, Big Pine Key, FL 33043
• 

  

  /9

  $12,500 per month

  • 4 Beds
  • 3 Baths
  • 2,855 Sq Ft
  • House for Rent

  28502 Channel View Dr, Little Torch Key, FL 33042

  This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

  Joseph Danieli AKT Realty LLC

  28502 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /46

  $1,390,000 Sold Aug 26, 2025

  229 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $1,207/SF
  • 30 Days On Market

  Current Estimated Value $1,387,796

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  229 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /20

  Not Listed For Sale

  31048 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft
  • Built 1967

  31048 Avenue J, Big Pine Key, FL 33043

  Last Sold Summary

  • $442/SF
  • 151 Days On Market

  Last Sold Price $260,000

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

  

  /39

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  51 Drost Dr, Summerland Key, FL 33042

  Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 551-4933

  51 Drost Dr, Summerland Key, FL 33042
• 

  

  /81

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • House for Rent

  441 La Fitte Rd, Summerland Key, FL 33042

  ** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in

  Carolina Gil Caralex Intl Realty Group Corp

  441 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /29

  $740,000 Sold Oct 31, 2025

  27138 Dolphin Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2022

  Last Sold Summary

  • 14% Below List Price
  • $561/SF
  • 181 Days On Market

  Current Estimated Value $732,336

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
• 

  

  /14

  Est $184,305 Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • 2 Days On Market

  Last Sold Price $190,000

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

  

  /43

  $1,799,000

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  51 Sawyer Dr, Summerland Key, FL 33042

  Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (844) 970-3222

  51 Sawyer Dr, Summerland Key, FL 33042
• 

  /2

  $1,450 per month

  • Property for Rent

  29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043

  🌴 Big Pine Key Lot for Rent - RV or Tiny Home Ready! 🌴Enjoy the Florida Keys lifestyle in this beautiful lot located in a desirable condominium community in Big Pine Key, just off U.S. 1 and close to everything!🏝️ Community Features:Heated pool for year-round enjoymentWasher/dryer available for tenantsSafe, friendly neighborhoodSteps from the bus stop, shops,

  Graciela Lozano KeysLifestyle Real Estate (KW)

  29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043
• 

  

  /47

  $1,100,000 Sold Jun 27, 2025

  21014 7th Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $808/SF
  • 102 Days On Market

  Current Estimated Value $1,104,572

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  21014 7th Ave, Summerland Key, FL 33042
• 

  

  /21

  Not Listed For Sale

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1978

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  Last Sold Summary

  • $565/SF
  • 0 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /42

  $815,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  29183 Cedar Dr, Big Pine Key, FL 33043

  This terrific canal-front home is situated on a fenced, low-maintenance 5,000 sq. ft. lot with 50 ft. concrete seawall and boat lift. The 50 ft. wide canal provides excellent access to the ocean and back-country with only one neighborhood bridge to go under (approx.. 10.5 ft. clearance.) Well-maintained and enjoyed by the owner for many years, it offers Hardi-board siding upstairs, a great

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 382-4166

  29183 Cedar Dr, Big Pine Key, FL 33043
• 

  

  /7

  $4,275,000 Sold Mar 04, 2026

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $1,371/SF
  • 114 Days On Market

  Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
• 

  

  /38

  Est $1,254,448 Not Listed For Sale

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1994

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  Last Sold Summary

  • 5% Above List Price
  • $750/SF
  • 15 Days On Market

  Last Sold Price $1,200,000

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

  

  /74

  $2,999,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  17041 Marlin Dr, Summerland Key, FL 33042

  Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (305) 809-8894

  17041 Marlin Dr, Summerland Key, FL 33042

Showing Results 41 - 80, Page 2 of 18