Monroe County, FL Homes

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  /40

  $699,000

  • 2 Beds
  • 2 Baths
  • 841 Sq Ft

  500 Burton Dr Unit 3308, Tavernier, FL 33070

  This Condo grossed $57,987.66 in 2025, with the owners using it all month in February ++ TWO oceanfront balconies with this updated 2/2 D model. Beautiful Ocean Views from the Living room & the Owners Suite. Impact windows and doors , nice tiled floors and tiled walk in showers. Private Cafe & Lounge on the Beach. Pool Bar by the Jr.Olympic Heated pool with 14 person Spa. Marina with direct ocean

  

  Tom Rodriguez

  American Caribbean Real Estate, Christie's International Real Estate

  (786) 713-8056

  500 Burton Dr Unit 3308, Tavernier, FL 33070
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  /16

  $5,357 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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  /20

  $1,200,000 Sold Apr 23, 2025

  411 + 415 1st St, Big Coppitt, FL 33040

  • 5 Beds
  • 5 Baths
  • 2,377 Sq Ft
  • Built 1996

  Last Sold Summary

  • 7% Below List Price
  • $505/SF
  • 111 Days On Market

  Last Listing Agent Christopher Scott,PA Expert Realty LLC (HQ)

  411 + 415 1st St, Big Coppitt, FL 33040
• 

  

  

  /39

  Est $2,048,204 Not Listed For Sale

  623 Simonton St Unit 9, Key West, FL 33040

  • 3 Beds
  • 4 Baths
  • 2,160 Sq Ft
  • Built 1997

  623 Simonton St Unit 9, Key West, FL 33040

  Last Sold Summary

  • 14% Above List Price
  • $833/SF
  • 48 Days On Market

  Last Sold Price $1,800,000

  Last Listing Agent Terri Spottswood Truman & Co. (KW)
• 

  

  

  /49

  $1,499,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,298 Sq Ft

  132 N Indies Dr, Marathon, FL 33050

  Experience the best of the Florida Keys in this beautifully designed 4-bedroom, 4-bath home in the sought-after Duck Key community. This waterfront property boasts an open floor plan, seamlessly blending indoor and outdoor living. The spacious kitchen features ample counter space, perfect for entertaining.Enjoy breathtaking canal views from the covered balcony, or step outside to your private

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 981-5471

  132 N Indies Dr, Marathon, FL 33050
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  /26

  $3,800 per month

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • House for Rent

  116 Long Ben Dr, Key Largo, FL 33037

  Canal front Updated 2-bedroom, 1-bathroom rental located in the desirable bayside community of Pirates Cove in Key Largo. This home features a bright, open-concept layout with a beautifully updated eat-in kitchen, stainless steel appliances, and a spacious living area filled with natural light. Impact windows and doors throughout, plus custom built-ins in the closets for added storage.Enjoy bay

  Katie Raskob Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  116 Long Ben Dr, Key Largo, FL 33037
• 

  

  /27

  $300,000 Sold Nov 26, 2025

  27983 Snapper Ln, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Below List Price
  • $446/SF
  • 60 Days On Market

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  27983 Snapper Ln, Little Torch Key, FL 33042
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  /46

  Est $705,299 Not Listed For Sale

  9828 Mariners Ave Unit 9828, Key Largo, FL 33037

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft
  • Built 1988

  9828 Mariners Ave Unit 9828, Key Largo, FL 33037

  Last Sold Summary

  • 13% Below List Price
  • $787/SF
  • 74 Days On Market

  Last Sold Price $810,000

  Last Listing Agent Carlos Lorenzo American Caribbean Real Estate
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  /66

  $4,695,000

  • 8 Beds
  • 4 Baths
  • 4,681 Sq Ft

  136 San Remo Dr, Islamorada, FL 33036

  Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique

  

  Shane Wilson

  Cypress Realty, Inc.

  (645) 215-8760

  136 San Remo Dr, Islamorada, FL 33036
• 

  

  /75

  $7,500 per month

  • 4 Beds
  • 5 Baths
  • 2,432 Sq Ft
  • House for Rent

  1516 Aqueduct Ln Unit 1, Key Largo, FL 33037

  Discover coastal living at its finest! This exceptional 4-bed, 3.2-bath canal-front home right next to Adams cut offers over 2,400 sq ft of beautifully designed living space with stunning bay views from wrap-around balconies and a rooftop terrace. Thoughtfully appointed with an elevator, indoor and outdoor kitchens, laundry room, and spacious layouts, this residence is ideal for entertaining and

  Kristal Rivera Diaz LPT Realty, LLC

  1516 Aqueduct Ln Unit 1, Key Largo, FL 33037
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  /61

  $2,550,000 Sold Jan 30, 2026

  3620 Sunrise Dr, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Below List Price
  • $1,385/SF
  • 17 Days On Market

  Current Estimated Value $2,621,474

  Last Listing Agent Zainya Zimmerer Berkshire Hathaway HomeServices Knight & Gardner Realty

  3620 Sunrise Dr, Key West, FL 33040
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  /50

  Est $852,415 Not Listed For Sale

  9849 Leeward Ave Unit 82, Key Largo, FL 33037

  • 2 Beds
  • 2 Baths
  • 1,179 Sq Ft
  • Built 1981

  9849 Leeward Ave Unit 82, Key Largo, FL 33037

  Last Sold Summary

  • 1% Above List Price
  • $712/SF
  • 41 Days On Market

  Last Sold Price $840,000

  Last Listing Agent Robin Guerasio Oceans Realty, LLC.
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  /27

  $987,500

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  3962 No Name Rd, Big Pine Key, FL 33043

  Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (888) 275-1086

  3962 No Name Rd, Big Pine Key, FL 33043
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  /33

  $2,950 per month

  • 4 Beds
  • 2 Baths
  • 1,998 Sq Ft
  • House for Rent

  235 Anne Bonny Dr, Key Largo, FL 33037

  Prime Pirates Cove waterfront living! Two private 2BR/1BA homes under one roof, each with full kitchen, washer/dryer, and screened patio. Three properties from open bay with stunning water views. Features include a 50-foot concrete dock, boat launch nearby, and a spectacular 1,000 sq. ft. rooftop deck perfect for entertaining or relaxing with panoramic vistas. Divided outdoor spaces give each

  Milena Wood Barrios and Associates Realty

  235 Anne Bonny Dr, Key Largo, FL 33037
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  /23

  $650,000 Sold Dec 30, 2025

  129 S Rd, Upper Matecumbe Key Islamorada, FL 33036

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft
  • Built 1958

  Last Sold Summary

  • 27% Below List Price
  • $737/SF
  • 118 Days On Market

  Current Estimated Value $638,616

  Last Listing Agent Wiebke Westedt LoKation Real Estate - Pompano Beach

  129 S Rd, Upper Matecumbe Key Islamorada, FL 33036
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  /26

  Est $1,533,739 Not Listed For Sale

  410 Porter Ln Unit 10, Key West, FL 33040

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

  410 Porter Ln Unit 10, Key West, FL 33040

  Last Sold Summary

  • 2% Above List Price
  • $1,364/SF
  • 87 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Richard Haskins Brightwild Real Estate
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  /40

  $62,000

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

  617 Front St Unit A-52 Week 52, Key West, FL 33040

  Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events.

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  (844) 967-2396

  617 Front St Unit A-52 Week 52, Key West, FL 33040
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  /21

  $2,950 per month

  • 2 Beds
  • 2 Baths
  • 700 Sq Ft
  • Property for Rent

  3312 Northside Dr Unit 316, Key West, FL 33040

  Freshly painted and clean as a whistle, this two bedroom and two bathroom condo is ready for occupancy. Tile floors throughout, central AC with ceiling fans, balcony, and granite countertops. Building has recently gone thru extensive renovations and there is a pool, tennis courts, and parking. Secured building. Sorry, pets aren't allowed. Washer and dryer located across the hall and an external

  Jimmy Lane Island Life Realty Experts

  3312 Northside Dr Unit 316, Key West, FL 33040
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  /104

  $12,000,000 Sold Feb 13, 2026

  19 Avacado St, Islamorada, FL 33036

  • 5 Beds
  • 7 Baths
  • 5,489 Sq Ft
  • Built 2017

  Last Sold Summary

  • 7% Below List Price
  • $2,186/SF
  • 26 Days On Market

  Current Estimated Value $6,839,305

  Last Listing Agent Leslie Leopold Ocean Sotheby's International Realty

  19 Avacado St, Islamorada, FL 33036
• 

  

  /31

  Est $1,813,429 Not Listed For Sale

  603 Angela St Unit 2, Key West, FL 33040

  • 2 Beds
  • 3 Baths
  • 1,440 Sq Ft
  • Built 1997

  603 Angela St Unit 2, Key West, FL 33040

  Last Sold Summary

  • 8% Above List Price
  • $1,163/SF
  • 70 Days On Market

  Last Sold Price $1,675,000

  Last Listing Agent Team Kaufelt Truman & Co. (KW)
• 

  

  /39

  $1,199,000

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft

  319 Woods Ave, Tavernier, FL 33070

  Charming 2-bedroom, 2-bath ground-level canal-front home located in a highly desirable Florida Keys neighborhood.The home features a split floor plan with a one-bedroom, one-bath layout on one side and a separate efficiency with its own bathroom and private entrance on the other--ideal for guests, extended family, or rental income.This property offers great potential to update and transform into

  

  Pierre Bellion

  Ocean Sotheby's International Realty

  (645) 225-2335

  319 Woods Ave, Tavernier, FL 33070
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  /8

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • Apartment for Rent

  8 Bowen Dr, Key Largo, FL 33037

  Bright and updated 1 bedroom / 1 bath apartment now available! This ground-floor unit offers a clean interior, private entry, and an in-unit washer and dryer. The upstairs level is tenant-occupied. Small pets considered. Available for annual rental.

  Courtney Jeffers Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  8 Bowen Dr, Key Largo, FL 33037
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  /2

  $55,000 Sold Oct 22, 2025

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  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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  /37

  Not Listed For Sale

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • $750/SF
  • 9 Days On Market

  Last Sold Price $540,000

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

  

  /50

  $689,000

  • 3 Beds
  • 2 Baths
  • 1,593 Sq Ft

  88181 Old Hwy Unit G21, Islamorada, FL 33036

  Enjoy resort-style living in this spacious, fully furnished 3-bedroom, 2-bath condominium located in the exclusive Coral Harbour Club. This residence features an open and airy floor plan where the kitchen, dining, and living areas blend seamlessly, creating an inviting space ideal for both relaxing and entertaining.The primary suite offers privacy and comfort with a modern en-suite bathroom

  

  Pierre Bellion

  Ocean Sotheby's International Realty

  (866) 764-5429

  88181 Old Hwy Unit G21, Islamorada, FL 33036
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  /58

  $4,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Townhouse for Rent

  94220 Overseas Hwy Unit 1D, Key Largo, FL 33037

  BAYFRONT UNIT - 2 BEDROOM + BOAT SLIP | available for 6 MONTHS or an ANNUAL LEASE! Sunset Hammock is a bayfront Gated community located on Buttonwood Sound, offering a peaceful Florida Keys lifestyle. Building A opens directly onto the bay with no obstructed views and faces due west, delivering some of the most spectacular nightly sunsets you'll find.This well-appointed 2-bedroom 2.5 bath

  Yvette Doherty Coldwell Banker Schmitt Key Largo

  94220 Overseas Hwy Unit 1D, Key Largo, FL 33037
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  /86

  $1,827,500 Sold Mar 26, 2026

  1501 Ocean Bay Dr Unit A2 & 50' deeded slip, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 2,127 Sq Ft
  • Built 1997

  Last Sold Summary

  • 9% Below List Price
  • $859/SF
  • 186 Days On Market

  Last Listing Agent April Struhs Coldwell Banker Schmitt Key Largo

  1501 Ocean Bay Dr Unit A2 & 50' deeded slip, Key Largo, FL 33037
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  /16

  Est $1,054,261 Not Listed For Sale

  483 Bahia Ave, Key Largo, FL 33037

  483 Bahia Ave, Key Largo, FL 33037

  Last Sold Summary

  • 14% Above List Price
  • 22 Days On Market

  Last Sold Price $925,000

  Last Listing Agent Jeannie Montes de Oca BHHS EWM Realty
• 

  

  /29

  $695,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft

  3729 Paula Ave, Key West, FL 33040

  Unlock the potential of this prime property located in the highly sought-after New Town Key West. Situated on a spacious 5,500 sq ft lot, this single-level home offers over 1,300 sq ft of air-conditioned living space, including three bedrooms and a versatile sunroom that can serve as a fourth bedroom. With ample room for an in-ground pool, a full bath, and a half guest bath, this property is

  

  Matthew Carlson

  Realty ONE Group Destination

  (786) 957-8965

  3729 Paula Ave, Key West, FL 33040
• 

  

  /22

  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 736 Sq Ft
  • Property for Rent

  151 Arbor Ln, Tavernier, FL 33070

  Tavernier Trailer for rent - 2 bed / 2 bath 6-month to 1 year rental $2,300 includes yard service! 1 smaller dog okay with landlords' permission & $25 monthly pet fee. Washer & dryer on site. Gated yard. F/L/S required and $40 background check fee. Close to Harry Harris Park for easy Boating access

  Kelly Randin RE/MAX All Keys Real Estate

  151 Arbor Ln, Tavernier, FL 33070
• 

  

  /19

  $315,000 Sold Dec 05, 2025

  201 Coppitt Rd Unit 106, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 536 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $588/SF
  • 14 Days On Market

  Current Estimated Value $308,067

  Last Listing Agent Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  201 Coppitt Rd Unit 106, Key West, FL 33040
• 

  

  /23

  Not Listed For Sale

  40 Ed Swift Rd, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 714 Sq Ft
  • Built 1977

  40 Ed Swift Rd, Key West, FL 33040

  Last Sold Summary

  • $511/SF
  • 20 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Letisia Powell Robert Slack LLC
• 

  

  /30

  $769,000

  • 3 Beds
  • 3 Baths
  • 1,596 Sq Ft

  148 Sunrise Dr, Tavernier, FL 33070

  Ideally located in the heart of Tavernier, this solid CBS home offers peace of mind with a concrete roof and impact windows. The permitted lower-level enclosure provides additional flexibility, while the main living area features a large, open-concept living, dining, and kitchen space, ideal for everyday living and entertaining. Step outside to a spacious, cleared backyard offering privacy with

  

  Lorie LaLonde

  American Caribbean Real Estate, Christie's International Real Estate

  (833) 976-3186

  148 Sunrise Dr, Tavernier, FL 33070
• 

  

  /68

  $7,500 per month

  • 4 Beds
  • 5 Baths
  • 2,432 Sq Ft
  • House for Rent

  1516 Aqueduct Ln, Key Largo, FL 33037

  Discover coastal living at its finest! This exceptional 4-bed, 3.2-bath canal-front home right next to Adams cut offers over 2,400 sq ft of beautifully designed living space with stunning bay views from wrap-around balconies and a rooftop terrace. Thoughtfully appointed with an elevator, indoor and outdoor kitchens, laundry room, and spacious layouts, this residence is ideal for entertaining and

  Kristal Rivera Diaz LPT Realty, LLC

  1516 Aqueduct Ln, Key Largo, FL 33037
• 

  

  /23

  $850,000 Sold Oct 31, 2025

  308 Peacon Ln, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,296 Sq Ft
  • Built 1923

  Last Sold Summary

  • 43% Below List Price
  • $656/SF
  • 299 Days On Market

  Current Estimated Value $864,482

  Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  308 Peacon Ln, Key West, FL 33040
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  /8

  Not Listed For Sale

  1550 Ocean Bay Dr Unit 42, Key Largo, FL 33037

  • 1 Bed
  • 45 Sq Ft
  • Built 1990

  1550 Ocean Bay Dr Unit 42, Key Largo, FL 33037

  Last Sold Summary

  • 2% Above List Price
  • $7,778/SF
  • 8 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Terry Canto American Caribbean Real Estate, Christie's International Real Estate
• 

  

  /39

  $849,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 1,320 Sq Ft

  11 Kestral Way, Key West, FL 33040

  This updated 4-bedroom, 3-bathroom townhome in the gated Key West Golf Club community is a prime investment opportunity and active vacation rental. Offering privacy, comfort, and resort-style living, it's just minutes from downtown Key West, beaches, and world-class dining.Inside, an open, light-filled floor plan features crown molding, neutral tile flooring, and refined finishes. The

  

  Austin Kimbler

  Expert Realty LLC (HQ)

  (833) 669-1452

  11 Kestral Way, Key West, FL 33040
• 

  

  /13

  $1,650 per month

  • 1 Bath
  • 450 Sq Ft
  • Apartment for Rent

  103365 Overseas Hwy Unit C, Key Largo, FL 33037

  End Unit C Newly Remodeled Studio Apartment featuring all Brand New Black Appliances. Conveniently located close to shopping, schools, restaurants, and more. Move -In Ready.

  Tracey Petrusha Venture Realty Group

  103365 Overseas Hwy Unit C, Key Largo, FL 33037
• 

  

  /28

  $720,000 Sold May 30, 2025

  211 5th St, Key Colony Beach, FL 33051

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft
  • Built 1968

  Last Sold Summary

  • 15% Below List Price
  • $646/SF
  • 258 Days On Market

  Current Estimated Value $756,178

  Last Listing Agent Natalie Ardis Coldwell Banker Schmitt Real Estate Co.

  211 5th St, Key Colony Beach, FL 33051
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  /64

  Not Listed For Sale

  15 W Cooks, Cook Island Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,551 Sq Ft
  • Built 1977

  15 W Cooks, Cook Island Key, FL 33043

  Last Sold Summary

  • $1,070/SF
  • 16 Days On Market

  Last Sold Price $1,660,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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