Summerland Key, FL Homes

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  /61

  Est $2,624,359 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft

  20886 4th Ave W, Summerland Key, FL 33042

  20886 4th Ave W, Summerland Key, FL 33042
• 

  

  

  /31

  $795,000

  • 2 Beds
  • 1 Bath
  • 1,562 Sq Ft

  360 W Shore Dr, Summerland Key, FL 33042

  Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

  Mark MacLaughlin R.W.A. Realty Inc

  360 W Shore Dr, Summerland Key, FL 33042
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  /14

  $250,000 Sold Feb 24, 2025

  1639 Pine Channel Dr, Little Torch Key, FL 33042

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

  Last Sold Summary

  • $37/SF
  • 7 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  1639 Pine Channel Dr, Little Torch Key, FL 33042
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  /39

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042
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  /43

  $1,799,999

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  Jolly Roger Drive on Cudjoe Key, where custom design meets open water views. This 4-bedroom, 2-bathroom residence showcases a designer kitchen with Viking appliances and high-end finishes, perfect for entertaining. The first floor offers two guest bedrooms, an office, and a full bath, while the second floor features a spacious guest room and the primary suite with a private balcony, ensuite bath,

  Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
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  /29

  $395,000 Sold May 19, 2025

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 5% Below List Price
  • 78 Days On Market

  Current Estimated Value $390,403

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
• 

  /2

  Est $761,000 Not Listed For Sale

  • Studio

  164 Newfound Blvd, Big Pine Key, FL 33043

  164 Newfound Blvd, Big Pine Key, FL 33043
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  /26

  $550,000

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  31171 Avenue H, Big Pine Key, FL 33043

  Big Pine Key Here's your opportunity to get into a 3 Bedroom. 2 Bath stilt home in the Keys. Metal Roof. Central A/C & Heat. Sliding door from house to Covered Porch. Garage and Storage, downstairs, Concrete Patio. Back yard has concrete slab for a storage shed. Sewer has been connected and paid for in full. Fenced. Easement behind fence line between this home and back neighbor. For utility co.

  Rose Dell Keller Williams Key West Compass Realty

  31171 Avenue H, Big Pine Key, FL 33043
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  /2

  $755,000 Sold Apr 24, 2025

  3786 Park Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $642/SF
  • 9 Days On Market

  Current Estimated Value $776,004

  Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  3786 Park Ave, Big Pine Key, FL 33043
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  /2

  Est $380,667 Not Listed For Sale

  • Studio

  2112 San Marco Dr, Big Pine Key, FL 33043

  2112 San Marco Dr, Big Pine Key, FL 33043
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  /34

  $1,650,000

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  3167 Stewart Rd, Summerland Key, FL 33042

  This 3-bedroom, 2-bath home provides rare-to-find tranquility and privacy in a pristine natural setting. The two-story cottage embodies Old Florida-style with lovingly maintained stone accents and an expansive covered porch overlooking open water. Inside, modern amenities enhance the home's charm. The updated kitchen opens to the living room, with both rooms featuring a wall of windows to take in

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  3167 Stewart Rd, Summerland Key, FL 33042
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  /47

  $1,282,000 Sold Nov 12, 2025

  29436 Independence Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $855/SF
  • 82 Days On Market

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  29436 Independence Ave, Big Pine Key, FL 33043
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  /2

  Est $386,667 Not Listed For Sale

  • Studio

  2120 San Marco Dr, Big Pine Key, FL 33043

  2120 San Marco Dr, Big Pine Key, FL 33043
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  /72

  $2,075,000 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
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  /2

  $255,000 Sold Oct 20, 2025

  150 Coral Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1993

  Last Sold Summary

  • $232/SF
  • 0 Days On Market

  Last Listing Agent Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  150 Coral Ave, Summerland Key, FL 33042
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  /2

  Est $507,000 Not Listed For Sale

  • 6,000 Sq Ft

  2078 San Marco Dr, Big Pine Key, FL 33043

  2078 San Marco Dr, Big Pine Key, FL 33043
• 

  

  /96

  $2,200,000

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  1631 Sunrise Dr, Big Pine Key, FL 33043

  SELLER IS MOTIVATED! All furnishings convey with property if buyer would like. Discover the epitome of waterfront living at Tropical Bay Estates. This 2023 new construction home offers an unparalleled paradise for your family and friends. Begin your days with stunning sunrises, engage in world-class fishing, and soak in breathtaking water views from nearly every part of the house. Encounter the

  John Huebner Premium Properties R.E Service

  1631 Sunrise Dr, Big Pine Key, FL 33043
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  /3

  $325,000 Sold Oct 09, 2025

  29153 Tulip Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1984

  Last Sold Summary

  • $356/SF
  • 0 Days On Market

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

  29153 Tulip Ln, Big Pine Key, FL 33043
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  /2

  Est $944,530 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 854 Sq Ft

  31441 Ave F, Big Pine Key, FL 33043

  31441 Ave F, Big Pine Key, FL 33043
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  /28

  $896,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

  This 3-bedroom, 2-bathroom stilted home offers 1,200 sq ft of thoughtfully designed space on a spacious canal-front lot.Enjoy the convenience of a 40 ft seawall, 10,000 lb boat lift, outdoor shower, and an enclosed garage with plenty of room for vehicles, boats, and water toys.Inside, the open-concept kitchen, living, and dining areas are equipped with brand-new appliances, ample cabinet space,

  Krystal Thomas eXp Realty LLC

  22922 Blackbeard Ln, Cudjoe Key, FL 33042
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  /51

  $420,000 Sold Nov 21, 2025

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 185 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
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  /2

  Est $962,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  460 Les Rohde Dr, Ramrod Key, FL 33042

  460 Les Rohde Dr, Ramrod Key, FL 33042
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  /107

  $3,200,000 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
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  /25

  $560,000 Sold Nov 21, 2025

  30342 Hibiscus Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 1969

  Last Sold Summary

  • 6% Below List Price
  • $371/SF
  • 230 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  30342 Hibiscus Ln, Big Pine Key, FL 33043
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  /2

  Est $1,183,659 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  29663 Saratoga Ave, Big Pine Key, FL 33043

  29663 Saratoga Ave, Big Pine Key, FL 33043
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  /34

  $1,149,000

  • 3 Beds
  • 3 Baths
  • 2,143 Sq Ft

  1615 Fern Ave, Big Pine Key, FL 33043

  Don't settle for small spaces! Welcome to this spacious and beautifully updated 3-bedroom, 2.5-bath home nestled on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Fully renovated, this two-story home feels open, airy, and inviting throughout.Inside, you'll find a large living room filled with natural light, offering plenty of space for family gatherings. A versatile office/den

  Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  1615 Fern Ave, Big Pine Key, FL 33043
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  /4

  $50,000 Sold Dec 19, 2025

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 41% Below List Price
  • 25 Days On Market

  Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
• 

  /2

  Est $414,104 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  31380 Ave G, Big Pine Key, FL 33043

  31380 Ave G, Big Pine Key, FL 33043
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  /50

  $1,725,000

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

  29678 Constitution Ave, Big Pine Key, FL 33043

  2.99% Assumable Loan! 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 kitchen features custom

  Callie Harris Brenda Donnelly Real Estate LLC

  29678 Constitution Ave, Big Pine Key, FL 33043
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  /2

  $50,000 Sold Nov 11, 2025

  Lot P No Name Key, No Name Key, FL 33043

  • Land
  • 0.5 Acre
  • $100,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 55 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot P No Name Key, No Name Key, FL 33043
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  /2

  Est $431,000 Not Listed For Sale

  • Studio

  L 39 Rose Dr, Big Pine Key, FL 33043

  L 39 Rose Dr, Big Pine Key, FL 33043
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  /45

  $1,950,000

  • 2 Beds
  • 2 Baths
  • 1,281 Sq Ft

  489 Sawyer Dr, Summerland Key, FL 33042

  OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  489 Sawyer Dr, Summerland Key, FL 33042
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  /39

  $705,000 Sold Sep 08, 2025

  181 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $647/SF
  • 7 Days On Market

  Current Estimated Value $707,952

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  181 Doubloon Ln, Summerland Key, FL 33042
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  /2

  Est $240,213 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,087 Sq Ft

  31030 E Ave, Big Pine Key, FL 33043

  31030 E Ave, Big Pine Key, FL 33043
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  /33

  $949,000

  • 2 Beds
  • 3 Baths
  • 1,140 Sq Ft

  151 Cutthroat Dr, Summerland Key, FL 33042

  Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access

  Heather Bennett Keller Williams Key West Compass Realty

  151 Cutthroat Dr, Summerland Key, FL 33042
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  /31

  $735,000 Sold Jun 06, 2025

  27373 Antigua Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2016

  Last Sold Summary

  • 2% Below List Price
  • $619/SF
  • 6 Days On Market

  Current Estimated Value $773,592

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  27373 Antigua Ln, Ramrod Key, FL 33042
• 

  /2

  Est $387,333 Not Listed For Sale

  • Studio

  117550 Caribe St, Sugarloaf Key, FL 33042

  117550 Caribe St, Sugarloaf Key, FL 33042
• 

  

  /45

  $1,550,000

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

  28538 John Silver Rd, Summerland Key, FL 33042

  Experience the best of the Keys lifestyle in this beautifully appointed 3-bedroom, 2-bath home, ideally positioned on a premium corner lot with approximately 236 feet of waterfront along a wide canal. Offering direct and easy access to open water, this property is a dream for boaters and water lovers alike.Step inside to a bright, open layout where expansive windows frame stunning views of

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28538 John Silver Rd, Summerland Key, FL 33042
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  /5

  $235,000 Sold Sep 09, 2025

  1388 Avenue B, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 33% Below List Price
  • 212 Days On Market

  Current Estimated Value $413,868

  Last Listing Agent Sarah Dolson Keller Williams Key West Compass Realty

  1388 Avenue B, Big Pine Key, FL 33043
• 

  /2

  Est $315,333 Not Listed For Sale

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042

  27328 St Vincent Ln, Ramrod Key, FL 33042

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