Summerland Key, FL Homes

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  /24

  $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
• 

  

  

  /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
• 

  

  

  /46

  $824,000

  $25K PRICE DROP

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

  30937 Baileys Ln, Big Pine Key, FL 33043

  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, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  30937 Baileys Ln, Big Pine Key, FL 33043
• 

  

  

  /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 $1,211,899

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
• 

  

  /68

  $3,199,000

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft

  1148 Big Pine Ave, Big Pine Key, FL 33043

  If you've been dreaming of the kind of place where the sunsets stop you in your tracks...this is it. Tucked away on a quiet road in Big Pine Key, this 2 Bedroom 2 Bath plus 1 Bedroom 1 Bath Guest Cottage one-of-a-kind point property delivers something incredibly rare in the Florida Keys, open water views and protected dockage, all wrapped into a private tropical setting on over an acre and a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  1148 Big Pine Ave, Big Pine Key, FL 33043
• 

  

  /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 $318,695

  Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

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

  

  /32

  Est $432,514

  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
• 

  

  /37

  $725,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  29160 Primrose Ln, Big Pine Key, FL 33043

  Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key. Featuring a garage and tons of storage inside and out, fenced yard & room for a pool! Inside you will find 3BR, 2 updated baths and a smart layout with an open concept living. Step outside to a beautiful covered porch the perfect spot to enjoy your morning coffee watching the

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  29160 Primrose Ln, Big Pine Key, FL 33043
• 

  

  /37

  $705,000

  Sold Aug 21, 2025

  27312 Anguila Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $614/SF
  • 127 Days On Market

  Current Estimated Value $758,928

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  27312 Anguila Ln, 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
• 

  

  /44

  $1,200,000

  • 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
• 

  

  /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 $758,748

  Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

  27235 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /33

  Est $896,935

  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
• 

  

  /54

  $1,049,000

  $50K 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
• 

  

  /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 $986,500

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  29039 Cedar Dr, Big Pine Key, FL 33043
• 

  /2

  Est $1,149,878

  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
• 

  

  /66

  $799,000

  $50K PRICE DROP Pending

  • 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

  701 Spanish Main Dr Unit 172, Cudjoe 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 $840,104

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $239,587

  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
• 

  

  /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 RE Co.

  29424 Forrestal Ave, 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
• 

  /2

  Est $1,026,624

  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
• 

  

  /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 RE Co.

  28560 Doubloon Rd, Summerland 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 Lowe Expert Realty LLC (HQ)

  27345 Barbuda Ln, Summerland 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
• 

  

  /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
• 

  /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

  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
• 

  

  /40

  $1,899,000

  $100K PRICE DROP Under Contract

  • 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

  28573 Le Grand Rd, Little Torch Key, FL 33042
• 

  

  /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 $806,664

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

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

  

  /5

  Est $1,481,798

  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
• 

  

  /48

  $698,800

  Under Contract

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

  29048 Iris Dr, Big Pine Key, FL 33043

  This 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

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  29048 Iris Dr, Big Pine Key, FL 33043
• 

  /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
• 

  

  /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
• 

  

  /58

  $979,000

  $30K PRICE INCREASE

  • 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
• 

  

  /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 $795,034

  Last Listing Agent Gidget Jackson RE/MAX Realty Group

  3686 Gulfstream St, Big Pine Key, FL 33043
• 

  

  /33

  Est $803,670

  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
• 

  

  /10

  $499,000

  • Land
  • 14,706 Sq Ft
  • $1,478,066 per Acre

  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

  63 Sugarloaf Dr, Sugarloaf Key, FL 33042
• 

  

  /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 $2,729,849

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

  20844 4th Ave W, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18