Summerland Key, FL Homes

• 

  

  

  /66

  $525,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private deck—an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  (645) 666-0297

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
• 

  

  

  /19

  $4,500 Per Month

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • House for Rent

  27346 Martinique Ln, Summerland Key, FL 33042

  Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

  Alicia Rufino Island Living Realty, LLC

  27346 Martinique Ln, Summerland Key, FL 33042
• 

  

  /2

  $510,000

  Sold Sep 08, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 972 Sq Ft
  • Built 1989

  Last Sold Summary

  • $525/SF

  Current Estimated Value $513,495

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  Unlisted Address
• 

  

  

  /22

  Not Listed For Sale

  133 Freedom Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 720 Sq Ft
  • Built 1972

  133 Freedom Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 49 Days On Market
• 

  

  

  /73

  $2,775,000

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

  23941 Henry St, Summerland Key, FL 33042

  Beach House Oceanfront retreat with protected dockage & direct access to both the Ocean & Gulf. Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (305) 395-0696

  23941 Henry St, Summerland Key, FL 33042
• 

  

  /73

  $2,925,000

  Sold Jun 10, 2025

  17018 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1991

  Last Sold Summary

  • 25% Below List Price
  • $1,987/SF
  • 122 Days On Market

  Current Estimated Value $2,946,581

  Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

  17018 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /14

  Not Listed For Sale

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 6,725 Sq Ft
  • Built 1975

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  Last Sold Summary

  • 7 Days On Market
• 

  

  /48

  $799,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  1672 Pandorea Ln, Big Pine Key, FL 33043

  Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, granite counters in the

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (855) 508-0388

  1672 Pandorea Ln, Big Pine Key, FL 33043
• 

  

  /58

  $572,000

  Sold May 27, 2026

  175 E Cahill Ct, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $567/SF
  • 40 Days On Market

  Current Estimated Value $596,391

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

  175 E Cahill Ct, Big Pine Key, FL 33043
• 

  

  /29

  Not Listed For Sale

  1693 Bayview Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 917 Sq Ft
  • Built 1976

  1693 Bayview Dr, Little Torch Key, FL 33042

  Last Sold Summary

  • 60 Days On Market
• 

  

  /43

  $763,000

  • 4 Beds
  • 2 Baths
  • 2,136 Sq Ft

  30374 Oleander Blvd, Big Pine Key, FL 33043

  If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with

  

  Patti Nickless

  Coldwell Banker Schmitt RE Co.

  (877) 357-0409

  30374 Oleander Blvd, Big Pine Key, FL 33043
• 

  

  /38

  $790,000

  Sold May 22, 2026

  30471 Coconut Hwy, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Built 1959

  Last Sold Summary

  • 14% Below List Price
  • $522/SF
  • 319 Days On Market

  Current Estimated Value $804,027

  Last Listing Agent Richard Haskins Buy The Keys

  30471 Coconut Hwy, Big Pine Key, FL 33043
• 

  

  /29

  Not Listed For Sale

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2001

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  Last Sold Summary

  • 14 Days On Market
• 

  

  /67

  $1,435,000

  Open Sat 11AM - 1PM $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft

  29562 Saratoga Ave, Big Pine Key, FL 33043

  Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and

  

  Ryan Gernaat

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 404-4618

  29562 Saratoga Ave, 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 $1,433,000

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  570 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /15

  Not Listed For Sale

  8 Calico Jack Circle Cir, Verifying, FL 33042

  8 Calico Jack Circle Cir, Verifying, FL 33042

  Last Sold Summary

  • 18 Days On Market
• 

  

  /34

  $1,575,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

  

  Anneliese Dietrick

  Coldwell Banker Schmitt RE Co.

  (645) 230-1445

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /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 $790,366

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  29025 Geranium Dr, Big Pine Key, FL 33043
• 

  

  /59

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • 76 Days On Market
• 

  

  /42

  $924,900

  $74K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  22954 Buccaneer Ln, Cudjoe Key, FL 33042

  Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water—ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (877) 542-8054

  22954 Buccaneer Ln, Cudjoe 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 $709,465

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

  27317 Cayman Ln, Summerland Key, FL 33042
• 

  

  /40

  Not Listed For Sale

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1996

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /37

  $899,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Cudjoe Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (877) 317-2645

  153 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /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 $733,282

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

  19462 Canal Dr, Summerland Key, FL 33042
• 

  

  /37

  Not Listed For Sale

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 9 Days On Market
• 

  

  /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

  (877) 939-4083

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

  /2

  $55,000

  Sold Oct 22, 2025

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  • Land
  • 5,000 Sq Ft
  • $479,160 per Acre

  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
• 

  

  /64

  Not Listed For Sale

  15 W Cooks, Cook Island Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,551 Sq Ft
  • Built 1977

  15 W Cooks, Cook Island Key, FL 33043

  Last Sold Summary

  • 16 Days On Market
• 

  

  /45

  $849,000

  $76K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  195 W Shore Dr, Summerland Key, FL 33042

  Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (844) 619-6402

  195 W Shore Dr, Summerland 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 $1,392,633

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

  229 Caribbean Dr E, 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
• 

  

  /70

  $2,800,000

  • 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)

  (855) 799-5158

  21640 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /68

  $2,250,000

  Sold Apr 03, 2026

  24266 Caribbean Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Below List Price
  • $1,095/SF
  • 14 Days On Market

  Current Estimated Value $2,273,007

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  24266 Caribbean Dr W, Summerland Key, FL 33042
• 

  

  /50

  Est $825,130

  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

  • 38 Days On Market
• 

  

  /69

  $3,500,000

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  1083 Labat Ln, Cudjoe Key, FL 33042

  Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 233-0155

  1083 Labat Ln, Cudjoe 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 $739,756

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
• 

  

  /35

  Est $219,010

  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

  • 22 Days On Market
• 

  

  /27

  $987,500

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  3962 No Name Rd, Big Pine Key, FL 33043

  Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (888) 275-1086

  3962 No Name Rd, 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 $1,106,731

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  21014 7th Ave, Summerland 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

  • 27 Days On Market

Showing Results 41 - 80, Page 2 of 18