Monroe County, FL Homes

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  /68

  $2,985,000

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront retreat with sandy beach, protected dockage & direct access to the Ocean & Gulf.Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (786) 686-4688

  23941 Henry St, Summerland Key, FL 33042
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  /30

  $3,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,147 Sq Ft
  • Townhouse for Rent

  96000 Overseas Hwy Unit C1, Key Largo, FL 33037

  Waterfront retreat. This townhouse/condo unit is nestled within the luxurious and sought after community of Buttonwood Bay. With its gated entry, your life inside is that of laid back waterfront living. This community offers multiple pools, tennis court, pickleball courts, basketball court, gym, community room, marina, gym and the beach! Great location within the complex! this is an updated 2

  Alicia Gilbert BHHS EWM Realty

  96000 Overseas Hwy Unit C1, Key Largo, FL 33037
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  /51

  $535,000 Sold Feb 10, 2026

  300 3rd St, Key Colony Beach, FL 33051

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Built 1982

  Last Sold Summary

  • 4% Below List Price
  • $519/SF
  • 35 Days On Market

  Current Estimated Value $549,688

  Last Listing Agent Karen Raspe, PA Ocean Sotheby's International Realty

  300 3rd St, Key Colony Beach, FL 33051
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  /25

  Not Listed For Sale

  209 Camelot Dr, Tavernier, FL 33070

  • 3 Beds
  • 2 Baths
  • 1,185 Sq Ft
  • Built 1971

  209 Camelot Dr, Tavernier, FL 33070

  Last Sold Summary

  • $1,350/SF
  • 45 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
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  /63

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 2,486 Sq Ft

  30468 Oleander Blvd, Big Pine Key, FL 33043

  Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuring a two-bedroom, two-bath main house and a one-bedroom, one-bath guest cottage with views over Bogie Channel. Enjoy leisurely days entertaining under the large poolside tiki hut or on the covered platform at the end of the 463-foot pier--perfect for relaxing with family and friends while watching sunsets

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 796-4209

  30468 Oleander Blvd, Big Pine Key, FL 33043
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  /21

  $3,800 per month

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • House for Rent

  508 28th Street Ocean, Marathon, FL 33050

  Beautifully renovated single family home!Well maintained, move in ready, centrally located in Marathon, close to restaurants, grocery stores, shopping centers, schools, library, police station, local park, Baptist hospital, clinic, and other local attractions (7 mile bridge, turtle hospital, crane point hammock, sombrero beach, boot key harbor)Amenities include:-induction

  508 28th Street Ocean, Marathon, FL 33050
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  /45

  $1,400,000 Sold Oct 22, 2025

  851 Narragansett Ln, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $1,042/SF
  • 27 Days On Market

  Last Listing Agent Robert Valenzuela Century 21 Circle- Islamorada

  851 Narragansett Ln, Key Largo, FL 33037
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  /32

  Est $364,412 Not Listed For Sale

  325 Calusa St, Key Largo, FL 33037

  • 2 Beds
  • 2 Baths
  • 300 Sq Ft
  • Built 2018

  325 Calusa St, Key Largo, FL 33037

  Last Sold Summary

  • 7% Below List Price
  • $1,300/SF
  • 147 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Luis Nunez Puro Real Estate
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  /51

  $479,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  55 Boca Chica Rd Unit 447, Key West, FL 33040

  Welcome to Seaside Resort, a gated, waterfront community just 10 minutes from the heart of Key West! This bright, cheerful 2 bed, 2 bath home with 864 sq ft of updated living space is move-in ready and offered turn-key furnished. Step inside this impeccably kept home to discover an open-concept layout filled with natural light, coastal charm, and a spacious feel. The kitchen features crisp white

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 230-1331

  55 Boca Chica Rd Unit 447, Key West, FL 33040
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  /37

  $2,975 per month

  • 2 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • Condo for Rent

  40 High Point Rd Unit D102, Tavernier, FL 33070

  Enjoy easy Florida Keys living in this fully furnished 2-bedroom, 2-bath condo in the desirable Plantation Villas community. Offered for 6 months or longer, this move-in-ready home is perfect for anyone seeking a comfortable, low-maintenance coastal lifestyle. The unit offers approximately 1,147 square feet of well-designed living space with a functional layout and impact-resistant windows for

  Jessie Morales Lifestyle International Realty

  40 High Point Rd Unit D102, Tavernier, FL 33070
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  /75

  $3,100,000 Sold Feb 06, 2026

  160 1st St, Key Colony Beach, FL 33051

  • 3 Beds
  • 3.5 Baths
  • 3,616 Sq Ft
  • Built 2006

  Last Sold Summary

  • 20% Below List Price
  • $857/SF
  • 260 Days On Market

  Current Estimated Value $3,312,717

  Last Listing Agent Tracy Chacksfield Berkshire Hathaway HomeServices Keys Real Estate

  160 1st St, Key Colony Beach, FL 33051
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  /60

  Est $936,445 Not Listed For Sale

  40 Florida Dr, Key Largo, FL 33037

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 2010

  40 Florida Dr, Key Largo, FL 33037

  Last Sold Summary

  • $442/SF
  • 69 Days On Market

  Last Sold Price $935,000

  Last Listing Agent Lorie Leal American Caribbean Real Estate, Christie's International Real Estate
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  /66

  $539,000

  • 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 decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /7

  $1,250 per month

  • Studio
  • 1 Bath
  • 180 Sq Ft
  • House for Rent

  1012 Watson St, Key West, FL 33040

  Its a small efficacy good for one only a twin bed will really fitA one year leaseNo dogs

  1012 Watson St, Key West, FL 33040
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  /16

  $1,400,000 Sold Mar 16, 2026

  570 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $933/SF
  • 14 Days On Market

  Current Estimated Value $277,898

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  570 Blackbeard Rd, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  808 Oakwood Ave, Key Largo, FL 33037

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1994

  808 Oakwood Ave, Key Largo, FL 33037

  Last Sold Summary

  • $391/SF

  Last Sold Price $375,000

  Last Listing Agent Jim Signor LoKation Real Estate - Pompano Beach
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  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
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  /8

  $2,850 per month

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  38 Silver Springs Dr, Key Largo, FL 33037

  Welcome to your slice of paradise! This charming 3-bedroom, 1-bath home in beautiful Key Largo offers the perfect blend of comfort and coastal living. Whether you're looking for a fully furnished retreat or prefer to bring your own style, this flexible rental has you covered. Enjoy bright, open living spaces, spacious bedrooms, and a relaxed island vibe just minutes from world-class boating,

  Yalexis De La Torre Luxe Properties

  38 Silver Springs Dr, Key Largo, FL 33037
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  /23

  $600,000 Sold Jul 15, 2025

  651 William St Unit 1, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 599 Sq Ft
  • Built 1933

  Last Sold Summary

  • 28% Below List Price
  • $1,002/SF
  • 191 Days On Market

  Current Estimated Value $672,121

  Last Listing Agent Barbara Bowers Preferred Properties (KW)

  651 William St Unit 1, Key West, FL 33040
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  /47

  Not Listed For Sale

  500 Hazel St, Key Largo, FL 33037

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1970

  500 Hazel St, Key Largo, FL 33037

  Last Sold Summary

  • $1,136/SF
  • 106 Days On Market

  Last Sold Price $1,400,000

  Last Listing Agent Tracey Petrusha Venture Realty Group
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  /43

  $598,000

  • 2 Beds
  • 2 Baths
  • 826 Sq Ft

  500 Burton Dr Unit 1415, Tavernier, FL 33070

  Top Floor 2/2 Condo with an Ocean view !! Upgraded condo with nice furniture arraignment that gives a comfortable open space feel. Updated Kitchen and both bathrooms have nice tiled floors & walls matching tiled floors throughout, Impact windows and doors too. Protected Marina with direct Ocean access, Private Oceanfront Cafe & Lounge, Heated Jr. Olympic pool w/ 14 person Spa, Pool Bar too !!

  

  Tom Rodriguez

  American Caribbean Real Estate, Christie's International Real Estate

  (645) 205-1027

  500 Burton Dr Unit 1415, Tavernier, FL 33070
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  /22

  $2,200 per month

  • Studio
  • 1 Bath
  • 400 Sq Ft
  • Condo for Rent

  2908 Harris Ave Unit Furnished Apartment, Key West, FL 33040

  This apartment is perfect for a single professional who needs a quiet ,safe place to live. Also looking for them to have a day job. It is a second story apartment ,fully furnished in tropical decor, includes all utilities, and furnishings so you just show up with your clothes . Their are kitchen items , pots and pans , dishes ,etc. Everything you need to be comfortable is there. And everything

  2908 Harris Ave Unit Furnished Apartment, Key West, FL 33040
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  /2

  $260,000 Sold Nov 03, 2025

  94825 Overseas Hwy #265, Key Largo, FL 33037

  • Land
  • 0.04 Acre
  • $6,842,105 per Acre

  Last Sold Summary

  • 26% Below List Price
  • 188 Days On Market

  Current Estimated Value $286,722

  Last Listing Agent Orian Levy Cromwell & Forbes Inc

  94825 Overseas Hwy #265, Key Largo, FL 33037
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  /2

  Est $1,632,947 Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • Built 2019

  Unlisted Address

  Last Sold Summary

  • 1% Above List Price
  • $192/SF
  • 360 Days On Market

  Last Sold Price $1,650,000

  Last Listing Agent Wendy Ives RE/MAX
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  /51

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  30985 Hibiscus Dr, Big Pine Key, FL 33043

  Privacy abounds with 130 ft. of canal-frontage to dock multiple boats. Boat traffic is not an issue since the property is at the end of canal (with resident manatee) affording easy water access to the Ocean and Gulf through the 50 ft. wide canal system. Privacy is enhanced by 10 ft.-plus hedges surrounding the fenced, 19,762 sq. ft. property with electric entry gate.Beautiful tropical gardens

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 284-4668

  30985 Hibiscus Dr, Big Pine Key, FL 33043
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  /5

  $2,995 per month

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

  3930 S Roosevelt Blvd Unit N411, Key West, FL 33040

  Looking for a long-term rental in Key West? This move-in ready 2-bedroom, 2-bath condo offers easy, comfortable island living with granite countertops in the kitchen, tiled flooring throughout for low maintenance, and an in-unit washer and dryer. Thoughtfully designed and well-maintained, it's an ideal option for those seeking a peaceful full-time residence.Las Salinas Condominiums features a

  Miriam Novotny Compass Florida, LLC

  3930 S Roosevelt Blvd Unit N411, Key West, FL 33040
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  /48

  $525,000 Sold Feb 19, 2026

  357 23rd St, Marathon, FL 33050

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft
  • Built 1958

  Last Sold Summary

  • 16% Below List Price
  • $520/SF
  • 98 Days On Market

  Current Estimated Value $540,391

  Last Listing Agent Sam Williams Coldwell Banker Schmitt Real Estate Co.

  357 23rd St, Marathon, FL 33050
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  /37

  Est $2,356,306 Not Listed For Sale

  1701 Laird St, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,581 Sq Ft
  • Built 2018

  1701 Laird St, Key West, FL 33040

  Last Sold Summary

  • 13% Below List Price
  • $1,708/SF
  • 60 Days On Market

  Last Sold Price $2,700,000

  Last Listing Agent Bobby Coe RE/MAX
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  /11

  $2,950,000

  • Land
  • 0.5 Acre
  • $5,895,128 per Acre

  246 & 248 Pescayo Ave, Marathon, FL 33050

  Ready to Build Your Dream Florida Keys Estate? This rare opportunity includes two large adjacent, cleared parcels, totaling 21,798 sq ft, in the heart of Marathon, already vested with a City of Marathon Market Rate Transferable Building Right, (TBR) -- meaning no wait, no red tape - start building immediately! Positioned on a deepwater canal with 7.9' controlling depth, this location is ideal for

  

  Joshua Mothner

  Coldwell Banker Schmitt Real Estate Co.

  (786) 982-6772

  246 & 248 Pescayo Ave, Marathon, FL 33050
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  /15

  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • House for Rent

  909 17th Terrace, Key West, FL 33040

  909 17th Terrace, Key West, FL 33040
• 

  

  /35

  $1,180,000 Sold Sep 17, 2025

  12399 Overseas Hwy Unit 24, Marathon, FL 33050

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $819/SF
  • 289 Days On Market

  Last Listing Agent Jessica Borraccino Coldwell Banker Schmitt Real Estate Co.

  12399 Overseas Hwy Unit 24, Marathon, FL 33050
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  /9

  Est $2,358,604 Not Listed For Sale

  234 Pescayo Ave, Marathon, FL 33050

  • 3 Beds
  • Built 2023

  234 Pescayo Ave, Marathon, FL 33050

  Last Sold Summary

  • 3% Above List Price
  • $3/SF
  • 133 Days On Market

  Last Sold Price $2,425,000

  Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.
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  /55

  $1,250,000

  • 3 Beds
  • 3 Baths
  • 2,440 Sq Ft

  1515 Sombrero Blvd Unit 4A, Marathon, FL 33050

  Experience elevated coastal living in this stunning top-floor corner penthouse waterfront condo at 1515 Sombrero Blvd, Unit 4A. Offering 3 bedrooms, 2.5 baths, and 2,440 sq ft, this residence showcases sweeping harbor and open water views from nearly every room. Arrive via a glass elevator overlooking the water and step into a welcoming foyer that opens to a spacious great room featuring a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 981-6823

  1515 Sombrero Blvd Unit 4A, Marathon, FL 33050
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  /41

  $6,500 per month

  • 3 Beds
  • 2 Baths
  • 2,208 Sq Ft
  • House for Rent

  2 Snipe Rd, Key Largo, FL 33037

  ~ JUSTED REDUCED ~ Seasonal rental in Key Largo. Newly renovated 3-story home with a clean, modern design. This spacious property offers 3 bedrooms, 2 bathrooms, and waterfront canal access with dockage included in the rental price. As a corner lot, it provides parking. Each floor features large terraces ideal for enjoying the outdoors. The top level includes a second living/entertainment room,

  Ricky Kallabat Keller Williams Capital Realty - Coral Gables

  2 Snipe Rd, Key Largo, FL 33037
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  /44

  $650,000 Sold Apr 23, 2025

  341 3rd Rd, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $319/SF
  • 69 Days On Market

  Current Estimated Value $695,275

  Last Listing Agent Sally Stribling Coldwell Banker Schmitt Key Largo

  341 3rd Rd, Key Largo, FL 33037
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  /2

  Not Listed For Sale

  0 Coconut Dr, Key Largo, FL 33037

  • 8,460 Sq Ft

  0 Coconut Dr, Key Largo, FL 33037

  Last Sold Summary

  • $21/SF

  Last Sold Price $180,000

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
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  /50

  $1,975,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,738 Sq Ft

  1015 Eaton St, Key West, FL 33040

  1015 Eaton Street, the art of island elegance, where historic soul meets modern sophistication. Four bedrooms. Updated baths. A new kitchen. Natural light everywhere. And a big, resort-style pool; a true rarity in Old Town! Positioned in the coveted heart of Old Key West, just steps from the Historic Seaport, 1015 Eaton Street is more than a home, it's a statement. A refined yet relaxed retreat

  

  Damian Vantriglia

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  (305) 745-7597

  1015 Eaton St, Key West, FL 33040
• 

  

  /17

  $3,400 per month

  • 4 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • House for Rent

  308 2nd Terrace, Key Largo, FL 33037

  Lovely home ready for your family. Lage 3/2 with media room which can be used for 4th bedroom. Large back screen porch and deck area. Premier family neighborhood. Available March 1st.

  Maryann Warren Coldwell Banker - Ft. Lauderdale

  308 2nd Terrace, Key Largo, FL 33037
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  /30

  $1,800,000 Sold Jul 08, 2025

  214 Fleming St, Key West, FL 33040

  • 2 Beds
  • 3 Baths
  • 1,312 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $1,372/SF
  • 136 Days On Market

  Current Estimated Value $1,828,490

  Last Listing Agent Rodney Culiver Last Key Realty, Inc (KW)

  214 Fleming St, Key West, FL 33040
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  /55

  Est $2,203,168 Not Listed For Sale

  296 Buttonwood Shores Dr, Key Largo, FL 33037

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1959

  296 Buttonwood Shores Dr, Key Largo, FL 33037

  Last Sold Summary

  • 8% Below List Price
  • $1,180/SF
  • 55 Days On Market

  Last Sold Price $2,400,000

  Last Listing Agent Karen Prince Coldwell Banker Schmitt Real E

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