Summerland Key, FL Homes

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  /32

  $1,899,000

  $301K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,800 Sq Ft

  3256 Catherine St, Summerland Key, FL 33042

  Tucked away on Big Torch Key, this CBS-constructed waterfront home offers a quiet, private setting with beautiful open-water views and remarkable year-round sunsets. Surrounded by the natural beauty of the Lower Keys, Key deer are often seen nearby, while backcountry boating and flats fishing are just minutes away. Boaters will appreciate convenient access to both Gulf and Atlantic

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  3256 Catherine St, Summerland Key, FL 33042
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  /17

  $4,895 Per Month

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • House for Rent

  22860 Blackbeard Ln, Cudjoe Key, FL 33042

  Enjoy the Florida Keys lifestyle in this beautifully upgraded 3-bedroom, 2-bathroom canal front home, now available for long-term rental in the highly desirable community of Cudjoe Key. Situated on a quiet dead-end street, this home offers privacy and minimal traffic, making it an ideal retreat.Boaters will appreciate the 10,000-pound boat lift, commercial ice maker downstairs, and quick,

  Maria Sanchez LoKation Real Estate

  22860 Blackbeard Ln, Cudjoe Key, FL 33042
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  /125

  $5,000,000

  Sold Jun 18, 2026

  24200 Overseas Hwy, Summerland Key, FL 33042

  • 5 Beds
  • 5.5 Baths
  • 3,000 Sq Ft
  • Built 1977

  Last Sold Summary

  • 19% Below List Price
  • $1,667/SF
  • 106 Days On Market

  Current Estimated Value $4,618,358

  Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

  24200 Overseas Hwy, Summerland Key, FL 33042
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  /3

  Not Listed For Sale

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  Last Sold Summary

  • 206 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC
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  /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
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  /16

  $4,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • House for Rent

  53 Barry Ave, Summerland Key, FL 33042

  This is a 2 story furnished or unfurnished single family house with a private pool, fenced in yard, screened patio, 2 bedrooms, 2 bathrooms with showers, stainless steel appliances, hurricane windows, washer and dryer, tile and wood floors. You are also able to use the amenities at our property next door such as 24 hour community gym and sauna. marina with boat ramp, outdoor games, bbq, kayaks

  Joseph Danieli AKT Realty LLC

  53 Barry Ave, Summerland Key, FL 33042
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  /46

  $2,000,000

  Sold Jul 14, 2026

  1330 Sugarloaf Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $1,232/SF
  • 62 Days On Market

  Current Estimated Value $2,152,594

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

  1330 Sugarloaf Blvd, Summerland Key, FL 33042
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  /6

  Not Listed For Sale

  3 Rd Ave Unit 1, Big Pine Key, FL 33043

  3 Rd Ave Unit 1, Big Pine Key, FL 33043

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Benjamin Daniels Lokation Real Estate
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  /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
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  /30

  $4,400 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
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  /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
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  /11

  Not Listed For Sale

  LOT 38 W Indies Dr, Ramrod Key, FL 33042

  LOT 38 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 144 Days On Market

  Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)
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  /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
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  /12

  $3,700 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  21074 Hamilton Ave, Cudjoe Key, FL 33042

  Enjoy the Florida Keys lifestyle in this spacious 3 bedroom, 2 bath waterfront duplex located in the desirable Cudjoe Gardens community. Step outside and enjoy dock space with direct boating access, making it easy to spend your days on the water. The property is conveniently located just seconds from the local marina.Please note that this is a duplex, so there are some shared

  Halley Haack Coldwell Banker Schmitt RE Co.

  21074 Hamilton Ave, Cudjoe Key, FL 33042
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  /49

  $280,000

  Sold Jun 03, 2026

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft
  • Built 1976

  Last Sold Summary

  • $406/SF
  • 98 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
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  /20

  Not Listed For Sale

  31048 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft
  • Built 1967

  31048 Avenue J, Big Pine Key, FL 33043

  Last Sold Summary

  • 151 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
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  /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
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  /19

  $11,600 Per Month

  • 5 Beds
  • 3 Baths
  • 2,528 Sq Ft
  • House for Rent

  142 Sawyer Dr, Summerland Key, FL 33042

  Welcome to Paradise!Enjoy this beautiful 5-bedroom, 3-bathroom waterfront rental featuring 120 feet of private dockage--perfect for boating enthusiasts and families alike. Shore power would be an additional charge.This fully furnished home is move-in ready and offers everything you need for a comfortable and relaxing stay. Whether you're planning a vacation getaway or an extended

  Tracey Petrusha Venture Realty Group

  142 Sawyer Dr, Summerland Key, FL 33042
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  /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 $2,256,263

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  24266 Caribbean Dr W, Summerland Key, FL 33042
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  /32

  Not Listed For Sale

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  Last Sold Summary

  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate
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  /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
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  /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 $751,332

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  27138 Dolphin Rd, Summerland Key, FL 33042
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  /14

  Est $198,098

  Not Listed For Sale

  27391 W Indies Dr, Ramrod Key, FL 33042

  27391 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /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
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  /7

  $4,275,000

  Sold Mar 04, 2026

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $1,371/SF
  • 114 Days On Market

  Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
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  /38

  Est $1,341,001

  Not Listed For Sale

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1994

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /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
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  /41

  $775,000

  Sold May 01, 2026

  22939 Privateer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1988

  Last Sold Summary

  • $602/SF
  • 3 Days On Market

  Current Estimated Value $774,846

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  22939 Privateer Dr, Summerland Key, FL 33042
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  /8

  Est $233,432

  Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall
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  /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
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  /36

  $1,120,000

  Sold Mar 24, 2026

  2148 Bahia Shores Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $933/SF
  • 1 Day On Market

  Current Estimated Value $1,127,151

  Last Listing Agent Anne Press Lokation Real Estate

  2148 Bahia Shores Rd, Big Pine Key, FL 33043
• 

  

  /22

  Est $705,694

  Not Listed For Sale

  27384 Saint Lucie Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft
  • Built 1988

  27384 Saint Lucie Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Madeleine Young Island Welcome Real Estate LLC
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  /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
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  /67

  $3,150,000

  Sold Jun 09, 2026

  270 E Caribbean Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,375 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $1,326/SF
  • 22 Days On Market

  Current Estimated Value $3,070,667

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  270 E Caribbean Dr, Summerland Key, FL 33042
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  /36

  Est $1,222,070

  Not Listed For Sale

  17246 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  17246 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Stephen Hachey Flat Fee MLS Realty
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  /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
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  /72

  $2,100,000

  Sold Aug 24, 2026

  27356 Dominica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2007

  Last Sold Summary

  • 5% Below List Price
  • $1,389/SF
  • 4 Days On Market

  Current Estimated Value $1,908,615

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

  27356 Dominica Ln, Summerland Key, FL 33042
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  /63

  Est $4,572,811

  Not Listed For Sale

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  • 6 Beds
  • 6.5 Baths
  • 4,200 Sq Ft
  • Built 2023

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Jenna Stauffer Ocean Sotheby's International Realty
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  /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
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  /55

  $5,003,500

  Sold Jan 05, 2026

  1151 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft
  • Built 2007

  Last Sold Summary

  • 28% Below List Price
  • $1,266/SF
  • 47 Days On Market

  Current Estimated Value $5,200,087

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

  1151 Ocean Dr, Summerland Key, FL 33042

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