Summerland Key, FL Homes

• 

  

  

  /46

  $1,599,000

  Sold Jul 28, 2026

  2237 San Remo Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 3 Baths
  • 1,244 Sq Ft
  • Built 1994

  Last Sold Summary

  • $1,285/SF
  • 27 Days On Market

  Current Estimated Value $1,289,929

  Last Listing Agent Suzanne Moore Suzanne Moore Real Estate

  2237 San Remo Dr, Big Pine Key, FL 33043
• 

  

  /2

  Est $3,234,640

  Not Listed For Sale

  999 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft
  • Built 2024

  999 Flagship Dr, Summerland Key, FL 33042
• 

  

  

  /54

  $675,000

  • 4 Beds
  • 2 Baths
  • 1,566 Sq Ft

  31011 Avenue C, Big Pine Key, FL 33043

  This 4-bedroom, 2-bath, 1566 sq. ft. home has so much to offer for the price! A spacious living area separates the primary bedroom and ensuite bath from the remaining bedrooms and bath. Features include tile floors throughout, a separate laundry room, a big sundeck and a ground-level storage enclosure. Covered parking is conveniently accessed from either Avenue C or Sands Rd. The 5,000 sq. ft.

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  31011 Avenue C, Big Pine Key, FL 33043
• 

  

  

  /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 $1,060,317

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  110 Doubloon Ln, Summerland Key, FL 33042
• 

  

  

  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • 66 Days On Market
• 

  

  /48

  $775,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft

  4016 Dorn Rd, Summerland Key, FL 33042

  Escape to the Lower Keys with this peaceful Big Torch Key retreat overlooking protected lands. Enjoy convenient boating access to both the Gulf and Atlantic via Niles Channel, then return to your 60 ft. concrete dock after a day of fishing or diving. This well-maintained, fully furnished 3-bedroom, 2-bath home is move-in ready, with sewer and FKAA 'city' water service, plus a cistern beneath the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  4016 Dorn Rd, Summerland Key, FL 33042
• 

  $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 $580,735

  Last Listing Agent Judith Exposito Luxe Properties

  22963 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /36

  Est $1,300,629

  Not Listed For Sale

  29565 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2019

  29565 Ranger Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  

  /43

  $725,000

  $24K PRICE DROP Under Contract

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

  28316 County Rd, Summerland Key, FL 33042

  *Back-up offers welcome.* Are you looking for a canal-front home that could use your TLC? Situated on a 9,375 sq. ft. fenced lot, this 2-bedroom, 3-bath CBS opportunity is about mid-way between the convenient 4A Boat Ramp to the west and Pine Channel to the east. Bright and airy, the extra-large kitchen was updated with new cabinets, stainless steel appliances and quartz counters in recent years.

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  28316 County Rd, 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 $1,735,562

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

  876 Gulf Dr, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043
• 

  

  /55

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  29038 Violet Dr, Big Pine Key, FL 33043

  This home has a little bit of everything! Tucked away toward the end of the street in Eden Pines, this 3/2, low maintenance property has a lot to offer. Upstairs is easy living with tile floors, a beautiful wood ceiling, and a large screened porch off the living area. The home is situated on a larger lot, with it's own boat slip, concrete seawall, and different 'pocket' areas to relax in. There

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  29038 Violet Dr, Big Pine Key, FL 33043
• 

  

  /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 $193,705

  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

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
• 

  

  /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

  701 Spanish Main Dr Unit 154, Cudjoe 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 $972,572

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  131 Doubloon Ln, Summerland Key, FL 33042
• 

  /2

  Est $2,296,535

  Not Listed For Sale

  305 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft
  • Built 1986

  305 S Point Dr, Summerland Key, FL 33042
• 

  

  /42

  $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 Lower Keys (KW)

  30374 Oleander Blvd, 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
• 

  

  /23

  Not Listed For Sale

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 8 Days On Market

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

  

  /3

  $375,000

  • Land
  • 6,000 Sq Ft
  • $2,722,500 per Acre

  27378 Jamaica Ln, Summerland Key, FL 33042

  Vacant lot with active building permit. Permit and plans include a fully designed green home with full concrete construction and concrete roof for 3 bedroom 2.5 bathrooms, large porch, storage and guest space, downstairs storm rated impact windows and doors, solar panel, gray water reclaim system plus rainwater system for irrigation and boat washing fish at Dawn cook your cat by dusk near Loki

  

  Natallie Liz

  Expert Realty LLC

  27378 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /64

  $809,000

  Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

  Current Estimated Value $823,907

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  3714 Pine St, Big Pine Key, FL 33043
• 

  /2

  Est $452,211

  Not Listed For Sale

  390 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1958

  390 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /56

  $2,220,000

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  937 Gulf Dr, Summerland Key, FL 33042

  High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout,

  

  Sandra Tuttle

  Island Welcome Real Estate

  937 Gulf Dr, Summerland Key, FL 33042
• 

  

  /91

  $3,675,000

  Sold May 11, 2026

  493 Coral Ave, Ramrod Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $2,127/SF
  • 10 Days On Market

  Current Estimated Value $3,563,635

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  493 Coral Ave, Ramrod Key, FL 33042
• 

  

  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 543 Days On Market

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

  

  /55

  $1,435,000

  Open Tue 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)

  29562 Saratoga Ave, Big Pine Key, FL 33043
• 

  

  /8

  $340,000

  Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 12,500 Sq Ft
  • $1,184,832 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

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

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Built 1943

  30919 Edward Rd Unit A & B, Big Pine Key, FL 33043
• 

  

  /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.

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /52

  $1,530,000

  Sold Jan 16, 2026

  1370 Long Beach Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,181 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $1,296/SF
  • 33 Days On Market

  Current Estimated Value $1,532,956

  Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

  1370 Long Beach Dr, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  430 Les Rohde Dr, Ramrod Key, FL 33042

  430 Les Rohde Dr, Ramrod Key, FL 33042
• 

  

  /38

  $1,349,000

  • 3 Beds
  • 2 Baths
  • 1,270 Sq Ft

  23057 Bluegill Ln, Summerland Key, FL 33042

  Look no further--this exceptional property truly has it all. This beautifully maintained CBS home boasts open-water views and is situated on an oversized lot on an extra-wide, deep canal, great for bigger boats, and just three houses in from the end. You'll be up on plane in seconds, with unparalleled boating access to both the Atlantic and Gulf. Ideally located closest to the premier backcountry

  

  Anneliese Dietrick

  Coldwell Banker Schmitt RE Co.

  23057 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /74

  $2,450,000

  Sold Aug 17, 2026

  17385 Keystone Rd, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,804 Sq Ft
  • Built 1985

  Last Sold Summary

  • 25% Below List Price
  • $1,358/SF
  • 168 Days On Market

  Current Estimated Value $2,837,733

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

  17385 Keystone Rd, Summerland Key, FL 33042
• 

  

  /73

  Est $864,700

  Not Listed For Sale

  547 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1991

  547 Heck Ave, Little Torch Key, FL 33042

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Andrew Whalen Lokation
• 

  

  /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

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

  

  /32

  $575,000

  Sold Jul 07, 2026

  29961 Pine Channel Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $676/SF
  • 100 Days On Market

  Current Estimated Value $586,242

  Last Listing Agent Terrance Sullivan Saltwater Real Estate Florida Keys, Inc

  29961 Pine Channel Rd, Big Pine Key, FL 33043
• 

  /2

  Est $466,078

  Not Listed For Sale

  20874 4th Ave, Cudjoe Key, FL 33042

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042
• 

  

  /70

  $2,800,000

  Pending

  • 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)

  21640 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /21

  $775,000

  Sold Mar 23, 2026

  27360 Saint Croix Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $673/SF
  • 272 Days On Market

  Current Estimated Value $791,841

  Last Listing Agent Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042

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