Summerland Key, FL Homes

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  /9

  $100,000 Sold Oct 29, 2025

  4W Cook Island, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 20% Below List Price
  • 194 Days On Market

  Current Estimated Value $103,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

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

  Est $257,865 Not Listed For Sale

  31373 Avenue C, Big Pine Key, FL 33043

  • 2 Beds
  • Built 1971

  31373 Avenue C, Big Pine Key, FL 33043

  Last Sold Summary

  • 10% Above List Price
  • $280/SF
  • 116 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Karen Liskey Key Colony Beach Realty
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  /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
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  /37

  $800,000 Sold Dec 19, 2025

  923 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $741/SF
  • 60 Days On Market

  Current Estimated Value $810,482

  Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

  923 Indies Rd, Summerland Key, FL 33042
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  /28

  Est $1,854,845 Not Listed For Sale

  27385 St Lucie Ln, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft
  • Built 1987

  27385 St Lucie Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 106% Above List Price
  • $452/SF
  • 0 Days On Market

  Last Sold Price $899,000

  Last Listing Agent Kathleen Gomez Coldwell Banker Schmitt RE Co.
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  /59

  $1,529,999 Open House 4/12

  • 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
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  /25

  $500,000 Sold Aug 19, 2025

  1620 Buttonwood Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft
  • Built 1974

  Last Sold Summary

  • 28% Below List Price
  • $490/SF
  • 265 Days On Market

  Current Estimated Value $554,076

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1620 Buttonwood Dr, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  31119 Avenue I, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft
  • Built 1961

  31119 Avenue I, Big Pine Key, FL 33043

  Last Sold Summary

  • $321/SF

  Last Sold Price $235,000

  Last Listing Agent Kaylee Moore Expert Realty LLC (HQ)
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  /51

  $1,250,000

  • 1 Bed
  • 3 Baths
  • 1,234 Sq Ft

  27001 Overseas Hwy, Ramrod Key, FL 33042

  Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample

  Bobby Coe RE/MAX Keys Connection (KW)

  27001 Overseas Hwy, Ramrod Key, FL 33042
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  /42

  $1,750,000 Sold Feb 26, 2026

  20771 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft
  • Built 2010

  Last Sold Summary

  • 17% Below List Price
  • $855/SF
  • 161 Days On Market

  Current Estimated Value $1,819,743

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  20771 2nd Ave W, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  29527 Constitution Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1982

  29527 Constitution Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • $646/SF

  Last Sold Price $1,085,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /68

  $2,299,000 Pending

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

  24266 Caribbean Dr W, Summerland Key, FL 33042

  A Private OCEANFRONT Retreat in Summerland Key. Nestled in the serene beauty of Summerland Key, this extraordinary 4-bedroom oceanfront residence offers a rare blend of architectural character, craftsmanship, and unobstructed open-water views. Designed for those who appreciate privacy and artistry, this is not a typical ''drive-by'' home - it's a destination.Thoughtfully configured in two

  Donna Pezzi Keller Williams Key West Compass Realty

  24266 Caribbean Dr W, Summerland Key, FL 33042
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  /30

  $557,235 Sold Apr 11, 2025

  30053 Pine Channel Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,006 Sq Ft
  • Built 1977

  Last Sold Summary

  • 7% Below List Price
  • $554/SF
  • 196 Days On Market

  Current Estimated Value $572,478

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  30053 Pine Channel Rd, Big Pine Key, FL 33043
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  /2

  Est $792,625 Not Listed For Sale

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2016

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  Last Sold Summary

  • 14% Below List Price
  • $495/SF

  Last Sold Price $695,000

  Last Listing Agent Mary Bryant Keller Williams Key West Compass Realty
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  /50

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 1,995 Sq Ft

  643 Indies Rd, Summerland Key, FL 33042

  Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

  Greg MacLaren Internet Realty of the Florida Keys

  643 Indies Rd, Summerland Key, FL 33042
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  /43

  $975,000 Sold May 30, 2025

  17425 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2018

  Last Sold Summary

  • 19% Below List Price
  • $677/SF
  • 65 Days On Market

  Current Estimated Value $985,534

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17425 Jamaica Ln, Summerland Key, FL 33042
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  /23

  Est $844,752 Not Listed For Sale

  27225 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  27225 Mariposa Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 10% Above List Price
  • $560/SF
  • 382 Days On Market

  Last Sold Price $764,500

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys
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  /53

  $2,300,000 New Construction

  • 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
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  /43

  $815,000 Sold Jan 23, 2026

  681 W Indies Dr, Summerland Key, FL 33042

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

  Last Sold Summary

  • 18% Below List Price
  • $894/SF
  • 211 Days On Market

  Current Estimated Value $810,387

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  681 W Indies Dr, Summerland Key, FL 33042
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  /2

  Est $771,465 Not Listed For Sale

  27087 Angelfish Rd, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2020

  27087 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $588/SF
  • 145 Days On Market

  Last Sold Price $765,000

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)
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  /43

  $1,200,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  1011 Caribbean Dr E, Summerland Key, FL 33042

  LIFE on the WATER! Set on a deep, flow-through canal with quick access to open water, this 3/2 home is designed for life on the water. Upstairs, enjoy breezy days and quiet evenings from the covered porch, while downstairs offers a rare 4-car garage--plenty of room for all your cars, gear, and Keys essentials. Easy, comfortable, and made for the lifestyle you've been dreaming about.Just 20

  Donna Pezzi Keller Williams Key West Compass Realty

  1011 Caribbean Dr E, Summerland Key, FL 33042
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  /58

  $3,335,000 Sold Jun 13, 2025

  23971 Henry St, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,950 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $1,131/SF
  • 37 Days On Market

  Current Estimated Value $3,249,971

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  23971 Henry St, Summerland Key, FL 33042
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  /69

  Not Listed For Sale

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Built 1988

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  Last Sold Summary

  • $631/SF
  • 461 Days On Market

  Last Sold Price $265,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  /13

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  22777 Jolly Roger Dr, Summerland Key, FL 33042

  Stop dreaming and start packing. This rare canal-front gem features a 2.75 assumable mortgage for qualified buyers—a game-changer in today’s market! Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even

  Olivia Poto GARRISON REALTY GROUP LLC

  22777 Jolly Roger Dr, Summerland Key, FL 33042
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  /45

  $900,000 Sold Apr 03, 2025

  2250 San Remo Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1989

  Last Sold Summary

  • 9% Below List Price
  • $573/SF
  • 243 Days On Market

  Current Estimated Value $944,322

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

  2250 San Remo Dr, Big Pine Key, FL 33043
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  /14

  Est $454,000 Not Listed For Sale

  29167 Cactus Ln, Big Pine Key, FL 33043

  29167 Cactus Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 505% Above List Price
  • 121 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty
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  /58

  $1,199,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 1,901 Sq Ft

  1547 Gardenia Ln, Big Pine Key, FL 33043

  Brand New Canal-Front Coastal Retreat in the Florida Keys....Welcome to this stunning new construction canal-front home, thoughtfully designed for comfort, durability, and modern island living. Situated on a 12,000 sq ft double lot, this elevated 4-bedroom, 3-bathroom residence offers 1,901 sq ft of living space and 9'6'' clearance under the home, providing peace of mind and ample storage

  Francesca Santiago Keller Williams Realty Professionals (KW)

  1547 Gardenia Ln, Big Pine Key, FL 33043
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  /39

  $1,725,000 Sold Apr 25, 2025

  474 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1973

  Last Sold Summary

  • 21% Below List Price
  • $1,037/SF
  • 127 Days On Market

  Current Estimated Value $1,710,172

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  474 Caribbean Dr E, Summerland Key, FL 33042
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  /2

  Est $321,000 Not Listed For Sale

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  • Studio

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 241% Below List Price

  Last Sold Price $94,000

  Last Listing Agent Yvette Toledo-Baste Compass Florida, LLC
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  /51

  $1,380,000

  • 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
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  /96

  $1,575,000 Sold Mar 23, 2026

  17176 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $669/SF
  • 63 Days On Market

  Current Estimated Value $1,697,750

  Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
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  Not Listed For Sale

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 1978

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Last Sold Summary

  • $408/SF
  • 78 Days On Market

  Last Sold Price $284,500

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  /22

  $1,150,000 Open Sat 11AM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  1331 Hudgins Dr, Summerland Key, FL 33042

  Construction Location & Orientation A Beautifully Appointed Canal Front Fortress All Concrete: Floors Walls Stairs Walk-Around Ramp Driveway Deck & Seawall. All Solar Glazed and Insulated Impact windows Enter the Unique Palm Tree Stained-glass Impact door to 24-inch Travertine floors and Nine-foot ceilings throughout. The Master Bedroom has French doors with a Tropical Stained-Glass Floral

  Camilo Perez Home Sold Realty, LLC

  1331 Hudgins Dr, Summerland Key, FL 33042
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  /22

  $750,000 Sold Apr 10, 2025

  29548 Enterprise Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 4 Baths
  • 2,232 Sq Ft
  • Built 1974

  Last Sold Summary

  • 38% Below List Price
  • $336/SF
  • 523 Days On Market

  Current Estimated Value $780,199

  Last Listing Agent Jennifer Weeks Select Properties of NWFL

  29548 Enterprise Ave, Big Pine Key, FL 33043
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  Not Listed For Sale

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

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

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  Last Sold Summary

  • $938/SF

  Last Sold Price $810,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  $1,175,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,518 Sq Ft

  22874 Bluegill Ln, Summerland Key, FL 33042

  Prestigious ''Cudjoe Ocean Shores'' home with quick, deep boating access to both the Atlantic and the Gulf. 85 feet of concrete dock with heavy duty davits and a large step-down water entrance for your backyard swimming and boating pleasure. This immaculate 3 bedroom, 3 bath home comes with a 10,200 Square Foot Lot, New Kitchen with Stainless Appliances, New Full Bath, Impact Windows and Doors,

  Greg MacLaren Internet Realty of the Florida Keys

  22874 Bluegill Ln, Summerland Key, FL 33042
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  /40

  $1,050,000 Sold Jan 12, 2026

  32734 Bimini Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • Built 1995

  Last Sold Summary

  • 14% Below List Price
  • $635/SF
  • 235 Days On Market

  Current Estimated Value $1,067,521

  Last Listing Agent Ally Kelley Ocean Sotheby's International Realty

  32734 Bimini Ln, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  Last Sold Summary

  • $712/SF

  Last Sold Price $370,000

  Last Listing Agent Lindsay Ryan EXP Realty LLC
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  /35

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  29662 Independence Ave, Big Pine Key, FL 33043

  Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

  Halley Haack Coldwell Banker Schmitt RE Co.

  29662 Independence Ave, Big Pine Key, FL 33043
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  /38

  $935,000 Sold Jun 30, 2025

  29374 Saratoga Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1986

  Last Sold Summary

  • 18% Below List Price
  • $835/SF
  • 150 Days On Market

  Current Estimated Value $971,671

  Last Listing Agent Dawn McComish Lokation Real Estate

  29374 Saratoga Ave, Big Pine Key, FL 33043

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