Summerland Key, FL Homes

• 

  

  

  /49

  Est $827,037

  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
• 

  

  

  /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
• 

  

  

  /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 $258,124

  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
• 

  

  

  /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
• 

  

  /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 $1,078,082

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1011 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  Est $719,767

  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
• 

  

  /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
• 

  

  /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 $1,292,272

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /68

  Est $904,877

  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
• 

  

  /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
• 

  

  /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 $884,122

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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
• 

  

  /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 $1,839,083

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland 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
• 

  

  /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
• 

  

  /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 $619,546

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  29030 Iris Dr, 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
• 

  

  /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
• 

  

  /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 $1,148,119

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

  22946 Bluegill Ln, 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
• 

  

  /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
• 

  

  /47

  $1,075,000

  Sold May 13, 2026

  110 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 9 Days On Market

  Current Estimated Value $1,079,826

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  110 Doubloon Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,057,833

  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
• 

  

  /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
• 

  

  /11

  $560,000

  Sold Jun 18, 2026

  22963 Anne Bonny Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 834 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $671/SF
  • 43 Days On Market

  Current Estimated Value $584,856

  Last Listing Agent Judith Exposito Luxe Properties

  22963 Anne Bonny Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040
• 

  

  /28

  $415,000

  $10K PRICE DROP Under Contract

  • 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, and enjoy access to the Blanche Bergin Marina Park, complete with boat ramp and available dockage for a fee. This property is a fixer-upper (ROGO letter in hand), 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

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  290 46th St, Summerland Key, FL 33042
• 

  

  /61

  $1,750,000

  Sold Mar 09, 2026

  876 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $1,493/SF
  • 122 Days On Market

  Current Estimated Value $1,708,408

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

  876 Gulf Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $348,466

  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
• 

  

  /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
• 

  

  /17

  $190,000

  Sold Apr 29, 2026

  29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 300 Sq Ft
  • Built 2018

  Last Sold Summary

  • 14% Below List Price
  • $633/SF
  • 66 Days On Market

  Current Estimated Value $166,769

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

  29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
• 

  /2

  Est $480,342

  Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042
• 

  

  /48

  $1,299,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  24347 Caribbean Dr W, Summerland Key, FL 33042

  Welcome to Summerland Key Cove! This beautifully home is perfectly situated on a deep-water canal with excellent boating access. Boaters will appreciate the new 17,000-lb boat lift and a quick ride to Looe Key, American Shoal, and the Adolf Bush wreck.The 1232 sq ft home sits on a 6,000 sq ft lot and features hurricane-impact windows, offering peace of mind and energy efficiency. The home has

  

  Shirley Carey

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  24347 Caribbean Dr W, Summerland Key, FL 33042
• 

  

  /34

  $840,207

  Sold Jul 03, 2026

  131 Doubloon Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $577/SF
  • 61 Days On Market

  Current Estimated Value $981,778

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  131 Doubloon Ln, 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
• 

  

  /42

  $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.

  30372 Palm Dr, Big Pine Key, FL 33043
• 

  

  /5

  $75,000

  Sold Jun 22, 2026

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  • Land
  • 14,810 Sq Ft
  • $220,588 per Acre

  Last Sold Summary

  • 46% Below List Price
  • 177 Days On Market

  Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
• 

  /2

  Est $209,258

  Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

Showing Results 161 - 200, Page 5 of 18