Summerland Key, FL Homes

• 

  

  

  /72

  $1,998,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,639 Sq Ft

  30980 Witters Ln, Big Pine Key, FL 33043

  MODERN ISLAND RETREAT ON BOGIE CHANNEL - BIG PINE KEY, FLDiscover the epitome of Lower Keys living in this luxurious 4-bedroom, 3.5-bath CBS pool home, ideally positioned on Bogie Channel with direct boating access. Built in 2022 and offered furnished, this elevated residence combines modern design, coastal charm, and unmatched functionality.Step inside to soaring ceilings, expansive windows, and

  Donna Pezzi Keller Williams Key West Compass Realty

  30980 Witters Ln, Big Pine Key, FL 33043
• 

  

  

  /3

  $49,000 Sold Jun 06, 2025

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 35% Below List Price
  • 206 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Vacant Land, Big Torch Key, FL 33042
• 

  

  /2

  Est $1,061,360 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  783 Pirates Rd, Summerland Key, FL 33042

  783 Pirates Rd, Summerland Key, FL 33042
• 

  

  

  /17

  $399,000 Pending

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  27977 Coral Shores Rd, Little Torch Key, FL 33042

  This 2 bedroom 1 bath with a screened in covered porch mobile home on just over 4100 sqft waterfront lot with great boating access.

  Dasha Ray Conch Realty LLC (KW)

  27977 Coral Shores Rd, Little Torch Key, FL 33042
• 

  

  

  /40

  $950,000 Sold Sep 17, 2025

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $825/SF
  • 85 Days On Market

  Current Estimated Value $999,533

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
• 

  /2

  Est $814,224 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,547 Sq Ft

  29654 Constitution Ave, Big Pine Key, FL 33043

  29654 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /26

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  31071 E Ave, Big Pine Key, FL 33043

  10AM-1PM OPEN HOUSE SAT 2/7/26 Stilt ''2005'' 3 Bedroom 2 Bath Modular home. Nice big columns. 50 X 100 lot. Metal roof, 8 X 24 covered porch with 2 sets of sliding doors off dining and living room. Porch faces south with no homes across the street. Storage 10 X 24 under house. Concrete slab. Close to community park, bike paths nearby. Public boat ramp at Spanish Harbor. Easy to show. No

  Rose Dell Keller Williams Key West Compass Realty

  31071 E Ave, Big Pine Key, FL 33043
• 

  

  /48

  $940,000 Sold Feb 28, 2025

  184 Cutthroat Dr, Summerland Key, FL 33042

  • 6 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 1963

  Last Sold Summary

  • 22% Below List Price
  • $405/SF
  • 184 Days On Market

  Current Estimated Value $1,009,244

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

  184 Cutthroat Dr, Summerland Key, FL 33042
• 

  /2

  Est $451,432 Not Listed For Sale

  • Studio

  24397 W Caribbean Dr, Summerland Key, FL 33042

  24397 W Caribbean Dr, Summerland Key, FL 33042
• 

  

  /107

  $2,999,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,538 Sq Ft

  747 La Fitte Rd, Summerland Key, FL 33042

  Spectacular open water location, with fabulous views from this newly constructed well-built oceanfront concrete home. Direct ocean or gulf access from massive dock that includes three boat lifts (one 15,000 pound, one 12,000 pound and a 10,000 pound double Waverunner lift). Relax in a large heated/chilled inground pool with a big covered pool patio area which drinks in the Ocean view. Home is

  John L. Markle Keller Williams Realty Premier Properties - Kendall

  747 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /44

  $853,000 Sold Aug 12, 2025

  873 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $789/SF
  • 123 Days On Market

  Current Estimated Value $875,238

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
• 

  /2

  Est $763,392 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  1313 State Rd Unit 4A, Little Torch Key, FL 33042

  1313 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /39

  $499,000

  • 2 Beds
  • 2 Baths
  • 618 Sq Ft

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

  Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

  Suzanne Moore Suzanne Moore Real Estate

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042
• 

  

  /29

  $510,000 Sold Apr 28, 2025

  1693 Bayview Dr, Little Torch Key, FL 33042

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

  Last Sold Summary

  • 13% Below List Price
  • $556/SF
  • 60 Days On Market

  Last Listing Agent Ana Tey-Guerra Trexy International Realty, Inc

  1693 Bayview Dr, Little Torch Key, FL 33042
• 

  

  /37

  Est $1,444,919 Not Listed For Sale

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

  2256 Matthews Rd, Big Pine Key, FL 33043

  2256 Matthews Rd, Big Pine Key, FL 33043
• 

  

  /38

  $830,000

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

  30471 Coconut Hwy, Big Pine Key, FL 33043

  Experience the charm of this beautifully renovated split-level home, designed with privacy and elegance in mind. The elevated master suite ensures a peaceful retreat, while additional spaces offer the versatile of an office or separate family room perfect for relaxation or entertaining. Step through the bedroom doors onto a spacious deck, where you can enjoy views of the meticulously landscaped

  Richard Haskins Buy The Keys

  30471 Coconut Hwy, Big Pine Key, FL 33043
• 

  

  /45

  $819,000 Sold May 19, 2025

  25093 Center St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Below List Price
  • $517/SF
  • 18 Days On Market

  Current Estimated Value $848,835

  Last Listing Agent Susan Hawkinson Bascom Grooms Real Estate (KW)

  25093 Center St, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /50

  $1,650,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  29678 Constitution Ave, Big Pine Key, FL 33043

  2.99% Assumable Loan (do not have to be VA)! Experience the true Keys lifestyle in this beautifully maintained waterfront home. Perfectly situated on a 60-foot wide canal, this fully furnished 3 bedroom/2.5 bath property blends privacy, comfort, and effortless access to both the Gulf and Atlantic. The primary suite boasts a huge walk-in closet and luxurious ensuite bath. The fully equipped

  Callie Harris Brenda Donnelly Real Estate LLC

  29678 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /31

  $925,000 Sold Jan 30, 2026

  29178 Guava Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $602/SF
  • 5 Days On Market

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

  29178 Guava Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 925 Sq Ft

  1669 Pine Channel Dr, Little Torch Key, FL 33042

  1669 Pine Channel Dr, Little Torch Key, FL 33042
• 

  

  /60

  $1,490,000 Open Mon 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and impact-rated windows & doors,

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
• 

  /2

  $500,000 Sold Jun 27, 2025

  538 Powell Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 912 Sq Ft
  • Built 1987

  Last Sold Summary

  • 17% Below List Price
  • $548/SF
  • 62 Days On Market

  Current Estimated Value $557,420

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  538 Powell Ave, Summerland Key, FL 33042
• 

  

  /4

  Est $242,547 Not Listed For Sale

  • 2 Beds

  31373 Avenue C, Big Pine Key, FL 33043

  31373 Avenue C, Big Pine Key, FL 33043
• 

  

  /52

  $1,199,000

  • 2 Beds
  • 2 Baths
  • 1,313 Sq Ft

  31135 Hollerich Dr, Big Pine Key, FL 33043

  A beautifully kept home with amazing views of the Gulf, and easy boating access to some of the best waters the Florida Keys have to offer. Just four houses in from the Gulf of Mexico/Spanish Harbor, and just a few minutes access to open water! This is outdoor living at its best! With 70 ft of concrete dock space you have plenty of room for any size boat. Relax and enjoy your outdoor entertainment

  Wyatt Tucker Action Keys Realty of the Lower FL Keys LLC

  31135 Hollerich Dr, Big Pine Key, FL 33043
• 

  

  /35

  $629,500 Sold Sep 30, 2025

  31463 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 24 Days On Market

  Current Estimated Value $639,704

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

  31463 Avenue A, Big Pine Key, FL 33043
• 

  

  /28

  Est $1,757,921 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft

  27385 St Lucie Ln, Ramrod Key, FL 33042

  27385 St Lucie Ln, Ramrod Key, FL 33042
• 

  

  /59

  $1,569,999 New Construction

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

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /34

  $580,000 Sold Sep 15, 2025

  30868 Malaga Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $537/SF
  • 137 Days On Market

  Current Estimated Value $609,802

  Last Listing Agent Loren Rea Truman & Co. (KW)

  30868 Malaga Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  31119 Avenue I, Big Pine Key, FL 33043

  31119 Avenue I, Big Pine Key, FL 33043
• 

  

  /55

  $2,300,000 Open Sun 11AM - 1PM

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

  30995 Watson Blvd, Big Pine Key, FL 33043

  FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  30995 Watson Blvd, Big Pine Key, FL 33043
• 

  

  /51

  $1,200,000 Sold Jun 16, 2025

  1060 W Shore Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2.5 Baths
  • 2,137 Sq Ft
  • Built 1977

  Last Sold Summary

  • 23% Below List Price
  • $562/SF
  • 26 Days On Market

  Current Estimated Value $1,285,190

  Last Listing Agent Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

  1060 W Shore Dr, Big Pine Key, FL 33043
• 

  /2

  Est $862,333 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,792 Sq Ft

  29664 & 29670 Constitution Ave, Big Pine Key, FL 33040

  29664 & 29670 Constitution Ave, Big Pine Key, FL 33040
• 

  

  /68

  $1,799,000

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

  1136 W Shore Dr, Big Pine Key, FL 33043

  Seller says SELL IT! - Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors

  Beata Sharpe Coldwell Banker Vanguard Realty

  1136 W Shore Dr, Big Pine Key, FL 33043
• 

  

  /40

  $640,000 Sold Sep 15, 2025

  3806 Dyer Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $702/SF
  • 54 Days On Market

  Current Estimated Value $656,819

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

  3806 Dyer Rd, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  29527 Constitution Ave, Big Pine Key, FL 33043

  29527 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /51

  $1,420,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  30890 Granada Ave, Big Pine Key, FL 33043

  Welcome to your tropical oasis--where the true spirit of the Florida Keys comes to life. This spacious 3-bedroom waterfront home blends casual island style with relaxed coastal living, offering 1,764 square feet designed for comfort and ease. High ceilings lined with tongue-and-groove wood immediately set the island tone as you enter the open living space. The kitchen flows seamlessly into the

  Sunnie San Lorenzo KeyIsle Realty

  30890 Granada Ave, Big Pine Key, FL 33043
• 

  

  /9

  $100,000 Sold Oct 29, 2025

  4W Cook Island, Big Pine Key, FL 33043

  • Land
  • 0.34 Acre
  • $294,126 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 194 Days On Market

  Current Estimated Value $99,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

  4W Cook Island, Big Pine Key, FL 33043
• 

  

  /14

  Est $478,047 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
• 

  

  /33

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  17226 Jamaica Ln, Summerland Key, FL 33042

  Completely remodeled, turn key 3 bed 2 bath canal front home that.backs up to the nature's preserve. Home features large pool with a bar area and 300 square feet enclosed storage ,mature landscaping and concrete wall with automatic gate . Easy boating access from new concrete dock to Atlantic ocean side and the Gulf. Actively profitable Airbnb home

  Stephen Hachey

  17226 Jamaica Ln, Summerland Key, FL 33042

Showing Results 321 - 360, Page 9 of 18