Summerland Key, FL Homes

• 

  

  

  /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
• 

  

  

  /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 Prudential Keyswide Properties

  0 Asturias Rd, Cudjoe Key, FL 33042
• 

  

  /2

  Est $701,159

  Not Listed For Sale

  27188 Dolphin Rd, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1991

  27188 Dolphin Rd, Ramrod Key, FL 33042
• 

  

  

  /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
• 

  

  

  /42

  $1,065,000

  Sold Jun 22, 2026

  27345 Barbuda Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $807/SF
  • 18 Days On Market

  Last Listing Agent Madeleine Young Island Welcome Real Estate LLC

  27345 Barbuda Ln, Summerland Key, FL 33042
• 

  

  /68

  Est $963,331

  Not Listed For Sale

  31670 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 1.5 Baths
  • 1,227 Sq Ft
  • Built 1956

  31670 Avenue C, Big Pine Key, FL 33043

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.
• 

  

  /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
• 

  

  /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 $1,289,717

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  29850 Journeys End Rd, Big Pine Key, FL 33043
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  /14

  Not Listed For Sale

  12, 13, 14 Cook Island, Cook Island Key, FL 33043

  12, 13, 14 Cook Island, Cook Island Key, FL 33043

  Last Sold Summary

  • 24 Days On Market

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

  

  /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
• 

  /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
• 

  

  /8

  Not Listed For Sale

  0000 Dorn Rd, Big Torch Key, FL 33042

  0000 Dorn Rd, Big Torch Key, FL 33042

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Lindsay Ryan EXP Realty LLC
• 

  

  /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
• 

  

  /40

  $790,000

  Sold Jul 02, 2026

  3686 Gulfstream St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $611/SF
  • 56 Days On Market

  Current Estimated Value $793,138

  Last Listing Agent Gidget Jackson RE/MAX Realty Group

  3686 Gulfstream St, Big Pine Key, FL 33043
• 

  

  /3

  Not Listed For Sale

  Vacant Lot Diane Rd, Big Pine Key, FL 33043

  Vacant Lot Diane Rd, Big Pine Key, FL 33043

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.
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  /76

  $1,550,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  29424 Forrestal Ave, Big Pine Key, FL 33043

  If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  29424 Forrestal Ave, Big Pine Key, FL 33043
• 

  

  /61

  $2,675,000

  Sold Jun 01, 2026

  20844 4th Ave W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Below List Price
  • $906/SF
  • 10 Days On Market

  Current Estimated Value $2,666,734

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

  20844 4th Ave W, Summerland Key, FL 33042
• 

  

  /34

  Not Listed For Sale

  27772 Astrangia Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1978

  27772 Astrangia Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)
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  /62

  $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 Lower Keys (KW)

  28560 Doubloon Rd, Summerland Key, FL 33042
• 

  

  /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
• 

  /2

  Est $1,227,400

  Not Listed For Sale

  1581 State Rd Unit 4A, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2007

  1581 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /21

  $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

  

  Sandra Tuttle

  Island Welcome Real Estate

  75 Lobstertail Rd, Big Pine Key, FL 33043
• 

  

  /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 $1,102,076

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1011 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040
• 

  

  /45

  $1,155,000

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  17183 Green Turtle Ln W, Summerland Key, FL 33042

  Live on the water on one of the largest lots in Sugarloaf Shores, fronting a 70 ft wide crystal clear swimming canal with easy ocean access. Recent upgrades make this home truly turnkey, including a new seawall, a new boat lift 15,000 lbs), and a newer roof. The big ticket items are already done for you.The grounds are the professionally landscaped with mature trees, fruit trees, a custom

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  17183 Green Turtle Ln W, Summerland Key, FL 33042
• 

  

  /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 $1,288,115

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /14

  Est $377,737

  Not Listed For Sale

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  • 3 Beds
  • Built 1943

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Shannon Butler Key Colony Beach Realty
• 

  

  /58

  $949,000

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  27358 Jamaica Ln, Summerland Key, FL 33042

  Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with water on 2 sides this property offers 150' of waterfront including a deep water basin, excellent dockage and easy access for boating, fishing, kayaking, or paddle boarding right from your backyard. Offering a flexible floor plan

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  27358 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /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 $864,164

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  /2

  Est $511,642

  Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042
• 

  

  /10

  $474,000

  $25K PRICE DROP

  • Land
  • 14,810 Sq Ft
  • $1,394,118 per Acre

  63 Sugarloaf Dr, Sugarloaf Key, FL 33042

  Welcome to the lowest priced waterfront lot with an active building permit and DEP and Army Corp mitigation fees paid 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

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  63 Sugarloaf Dr, Sugarloaf Key, FL 33042
• 

  

  /50

  $1,900,000

  Sold Mar 27, 2026

  711 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $950/SF
  • 62 Days On Market

  Current Estimated Value $1,762,568

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
• 

  

  /41

  $799,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,082 Sq Ft

  22822 Buccaneer Ln, Summerland Key, FL 33042

  SELLER ACCEPTING BACK-UP OFFERS: Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal. Access to both the Atlantic and Gulf is easy and achievable in minutes, making it an ideal base for fishing, boating, and enjoying the Keys lifestyle. One of the home's standout features is its exceptional privacy. With no

  

  Cardenas & Krug Team

  Coastal Collection Real Estate Inc.

  22822 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /26

  $610,000

  Sold Apr 03, 2026

  29030 Iris Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft
  • Built 1974

  Last Sold Summary

  • 15% Below List Price
  • $451/SF
  • 449 Days On Market

  Current Estimated Value $624,180

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  29030 Iris Dr, Big Pine Key, FL 33043
• 

  /2

  Est $779,974

  Not Listed For Sale

  53 Treasure Chest Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1991

  53 Treasure Chest Dr, Cudjoe Key, FL 33042
• 

  

  /34

  $889,900

  • 3 Beds
  • 1 Bath
  • 1,638 Sq Ft

  27 Lake Dr N, Summerland Key, FL 33042

  Welcome to the Mango Cottage on Summerland Key! Tucked away on a quiet dead-end street, this 3 bedroom, 1 bath canal front CBS home combines the laid back Florida Keys lifestyle with excellent boating access and a few features you simply don't find everywhere. Surrounded by multiple mature fruit trees, including several mango trees! This property has a distinctly tropical feel from the moment you

  

  Coby Taylor

  Expert Realty LLC (HQ)

  27 Lake Dr N, Summerland Key, FL 33042
• 

  

  /41

  $1,105,000

  Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,125,577

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  /2

  Est $199,913

  Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042
• 

  

  /63

  $3,100,000

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

  361 Avenue D, Summerland Key, FL 33042

  Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect blend of luxury, privacy, and island living. A charming thatched-covered lanai and custom bamboo-etched glass doors welcome you into an open-concept floor plan where floor to ceiling windows frame breathtaking Atlantic Ocean views.

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  361 Avenue D, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18