Monroe, FL Homes

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  /109

  $6,450,000

  • 3 Beds
  • 3 Baths
  • 4,687 Sq Ft

  3742 Seagrape St, Big Pine Key, FL 33043

  Breathe in serenity during your escape to the ''The Castle'', a luxurious gated Gulf-front estate gracefully spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a rare blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected

  Ally Kelley Ocean Sotheby's International

  3742 Seagrape St, Big Pine Key, FL 33043
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  /47

  $312,500 Sold Mar 17, 2025

  • 520 Sq Ft
  • $601/SF
  • 194 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2000

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

  OPEN WATER VIEWS with TRANSIENT RENTAL. This home is well cared for with newer construction (2000) offers a inviting opportunity to soak up Florida Keys sunshine with amenities readily available. Turnkey features allow you to move right in or get immediately into the rental market. Upgraded vinyl plank flooring, newly added stackable washer and dryer, all new drywall, accordion hurricane

  Anne Press Lokation Real Estate

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
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  /55

  Est $1,339,312 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,108 Sq Ft

  350 W Shore Dr, Summerland Key, FL 33042

  350 W Shore Dr, Summerland Key, FL 33042
• 

  

  

  /40

  $989,000

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

  437 Pirates Rd, Little Torch Key, FL 33042

  Now offered in the sought after Jolly Roger Estates, this beautifully maintained one owner, free-flowing canal front home is just 10 years old and move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence features three bedrooms and two bathrooms with refined details such as crown molding, tray ceilings, tile showers, and an open-concept living area. A new metal roof was

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
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  /43

  $1,300,000 Sold Mar 14, 2025

  • 1,171 Sq Ft
  • $1110/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  1050 Gulf Dr, Summerland Key, FL 33042

  Located on desirable Summerland Key, this property has it ALL. Located in Summerland Cove on a very private lot, 5 min to open water, on a 50 foot wide canal featuring a 10k boat lift, Davits and a step down for easy access for kayaks and paddle boards. As you enter through the spacious screened porch,enjoy the outdoor living and dining space overlooking your fruit tree filled yard and saltwater

  Michelle Howerton Brenda Donnelly Real Estate LLC

  1050 Gulf Dr, Summerland Key, FL 33042
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  /2

  Est $825,079 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,193 Sq Ft

  30362 Flamingo Ln, Big Pine Key, FL 33043

  30362 Flamingo Ln, Big Pine Key, FL 33043
• 

  

  /42

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  28009 Gulf Blvd, Big Pine Key, FL 33043

  Canal-Front Paradise in the Heart of the National Key Deer RefugeBig Pine Key, FloridaWelcome to your serene island escape! Nestled in the heart of the National Key Deer Refuge, this beautifully renovated two-bedroom, two-bath stilt home offers the perfect blend of modern comfort and natural beauty.Property Highlights:Canal-Front Property with ample space for a dock -- ideal for boating

  Ian Calderwood Bluescape Real Estate

  28009 Gulf Blvd, Big Pine Key, FL 33043
• 

  

  /25

  $310,000 Sold Mar 13, 2025

  • 1,064 Sq Ft
  • $291/SF
  • 49 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  28232 Dorothy Ave, Summerland Key, FL 33042

  Unique Opportunity in Prime Location within walking distance to public boat ramp!This two-bedroom, one-and-a-half-bath mobile home needs some TLC and is ready to be refurbished. The cozy layout features two bedrooms and one and a half bath. The 6000 sq ft lots offers plenty of storage and possibility.The real value here lies in the potential--this property could serve as a teardown, allowing you

  Lanny Gardner Bluescape Real Estate

  28232 Dorothy Ave, Summerland Key, FL 33042
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  /28

  Est $1,190,844 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  2237 San Remo Dr, Big Pine Key, FL 33043

  2237 San Remo Dr, Big Pine Key, FL 33043
• 

  

  /16

  $920,000

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

  1549 Pandorea Ln, Big Pine Key, FL 33043

  The perfect home for comfort and relaxation in the beautiful Florida Keys. This beautiful 2-bedroom, 1-bath home is located in the Eden Pines Neighborhood in Big Pine Key. Nestled along a serene canal, this property is an ideal haven for boaters. Enjoy direct access to the FL Keys waters right from your backyard. Its modern kitchen, stylish floors, and cozy bedrooms are perfect for your Keys

  Danelys Thondike Buy The Keys

  1549 Pandorea Ln, Big Pine Key, FL 33043
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  /41

  $1,375,000 Sold Mar 13, 2025

  • 1,499 Sq Ft
  • $917/SF
  • 77 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  20785 5th Ave W, Summerland Key, FL 33042

  Welcome to your waterfront paradise in Cudjoe Gardens! This exceptional 2-bedroom, 2-bathroom home boasts a stunning outdoor oasis and stylish interior, perfect for relaxation and entertaining. Step outside to a beautiful paver pool deck surrounding a sparkling pool, ideal for sunbathing and gatherings. Enjoy the convenience of a fillet station for your catch of the day, and take advantage of the

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20785 5th Ave W, Summerland Key, FL 33042
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  /2

  Est $407,353 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  30869 Bay Shore Dr, Big Pine Key, FL 33043

  30869 Bay Shore Dr, Big Pine Key, FL 33043
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  /44

  $549,900

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

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

  Transient 1 Day Rentals Allowed! Welcome to your tropical paradise! This charming 2 bedroom, 2 bathroom home in Cudjoe Key offers the perfect blend of comfort and island living. Enjoy the open-concept living and dining area, perfect for entertaining guests and take in all of the sunrise and sunset views from your porch! Take advantage of all the amenities that come with being located in the well

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /40

  $837,000 Sold Mar 12, 2025

  • 1,184 Sq Ft
  • $707/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  22994 Anne Bonny Ln, Summerland Key, FL 33042

  Canal home on a corner lot offers amazing water views and boating access to the Atlantic and Gulf. This Cudjoe Key home is just 21 miles from Key West. Elevated home on a cul-de-sac boasting tropical landscape and stunning views. This well-maintained home has been owner occupied and features three bedrooms, two baths including an updated en suite primary bathroom, spacious kitchen with gorgeous

  Bascom Grooms Bascom Grooms Real Estate (KW)

  22994 Anne Bonny Ln, Summerland Key, FL 33042
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  /31

  Est $729,438 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  174 Newfound Blvd, Big Pine Key, FL 33043

  174 Newfound Blvd, Big Pine Key, FL 33043
• 

  

  /35

  $625,000

  • 4 Beds
  • 2 Baths
  • 1,200 Sq Ft

  117 W Sandy Cir, Big Pine Key, FL 33043

  Looking for that Family Home in The Florida Keys that fits your budget, well you just found it! This home is within the limits of a FHA Loan in Monroe County, Florida.Discover paradise at this serene retreat located on a quiet street in the heart of Big Pine Key. 117 W. Sandy Drive is the perfect Keys getaway or full-time family residence for those who crave peace, privacy, and a great

  Bobby Coe RE/MAX Keys Connection (KW)

  117 W Sandy Cir, Big Pine Key, FL 33043
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  /40

  $785,000 Sold Mar 12, 2025

  • 1,155 Sq Ft
  • $680/SF
  • 184 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  17236 Keystone Rd, Summerland Key, FL 33042

  Nestled on a generous 20,000 square-foot lot with tranquil canal frontage, this charming two-bedroom, two-bathroom home invites your personal touch. The downstairs area includes a screened-in porch, providing additional living space; buyers should verify its permitted use.The upstairs features an open floor plan that harmoniously connects the kitchen, living, and dining areas, complemented by a

  Everett Watkins Keller Williams Key West Compass Realty

  17236 Keystone Rd, Summerland Key, FL 33042
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  /49

  Est $1,129,205 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  403 Indies Rd, Ramrod Key, FL 33042

  403 Indies Rd, Ramrod Key, FL 33042
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  /45

  $975,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  25057 7th St, Summerland Key, FL 33042

  Tropical Tranquility Meets Spacious Island Living.Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the

  Christopher Tanaka Coldwell Banker Schmitt RE Co. Lower Keys Office

  25057 7th St, Summerland Key, FL 33042
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  /44

  $907,500 Sold Mar 10, 2025

  • 1,365 Sq Ft
  • $665/SF
  • 47 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1990

  3633 Blue Lagoon St, Big Pine Key, FL 33043

  This meticulously maintained 3 bedroom, 3 bathroom home on Big Pine Key offers the the ultimate in privacy and tranquility, with no neighbors on either side, it sits in the middle of an acre of government non-buildable land. 1365 square feet of living area, the house has a spacious, open floor plan, strand woven bamboo floors with 2 large en-suites and a comfortable 3rd bedroom. The kitchen

  David Kaufmann Century 21 Circle

  3633 Blue Lagoon St, Big Pine Key, FL 33043
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  /37

  Est $1,146,987 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  716 Caribbean Dr E, Summerland Key, FL 33042

  716 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /25

  $479,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  27973 Snapper Ln, Little Torch Key, FL 33042

  Welcome to your dream retreat by the sea! This beautifully renovated 2/2 offers the perfect blend of classic coastal charm and modern upgrades. Recently renovated with a new roof (2021), new doors and windows (2000), new AC units and updated paint throughout. This home is located in a serene waterfront community with an unlimited free-access boat launch located only minutes from the house. Enjoy

  Bill Vaught (REO Vaught Realty LLC Vaught Realty

  27973 Snapper Ln, Little Torch Key, FL 33042
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  /14

  $225,000 Sold Mar 07, 2025

  • Land

  • 246 Days On Market

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  Transient RV/Buildable lot in the much sought after Venture Out at Cudjoe Key. This is your chance to own a piece of paradise at an affordable price! The Venture Out Community is located only 19 miles from Key West, but with all of the amenities here you may never want to leave! There is a heated pool, hot tub, fuel docks, boat ramps, fish cleaning stations, bocce ball and tennis courts, pickle

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
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  /42

  Est $635,343 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft

  227 Airport Dr N, Summerland Key, FL 33042

  227 Airport Dr N, Summerland Key, FL 33042
• 

  

  /21

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  27360 Saint Croix Ln, Summerland Key, FL 33042

  Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

  Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
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  /46

  $1,350,023 Sold Mar 05, 2025

  • 1,819 Sq Ft
  • $742/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1993

  817 Grenada Ln, Summerland Key, FL 33042

  Welcome to Your Dream Waterfront Escape! This stunning property offers exceptional boating accessibility, just a minute's ride from the Atlantic and Gulf. Featuring three spacious bedrooms, a bonus room and beautifully updated bathrooms, this home is designed for comfort and style. At the heart of the home lies an incredible chef's kitchen, perfect for culinary enthusiasts! It boasts high-end

  Melissa Graham Bluescape Real Estate

  817 Grenada Ln, Summerland Key, FL 33042
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  /40

  Est $2,190,274 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  20995 2nd Ave W, Summerland Key, FL 33042

  20995 2nd Ave W, Summerland Key, FL 33042
• 

  

  /10

  $675,000

  • Land
  • 0.39 Acre
  • $1,713,961 per Acre

  29557 Geraldine St, Big Pine Key, FL 33043

  Oversized Waterfront Commercial lot located in the Big Pine Shores neighborhood. This parcel measures approximately 17,000 square feet (0.39 acres) and is zoned CFSD-12 (Coastal Fishery and Shoreland District) per Monroe County records, offering a rare opportunity for Fishing related activities and or residential development. Geraldine Street runs roughly north-south on the island's eastern side,

  Greg Dully RE/MAX All Keys Real Estate

  29557 Geraldine St, Big Pine Key, FL 33043
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  /2

  $144,000 Sold Mar 04, 2025

  • Land

  • 2 Days On Market

  Lot 15 Aztec St, Sugarloaf Key, FL 33042

  Best priced lot in popular Indian Mount Estates, Sugarloaf Key! Priced for only $149,250, take advantage of this opportunity to develop this Tier III (infill lot located in a developed subdivision with adequate infrastructure), 50 x 100 platted lot convenient to the community boat ramp and near the Sugarloaf School for elementary through middle school grades and the associated recreation venues.

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

  Lot 15 Aztec St, Sugarloaf Key, FL 33042
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  /49

  Est $7,217,597 Not Listed For Sale

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  17279 Oleander Ln, Sugarloaf Key, FL 33042
• 

  

  /55

  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  Nightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rent license. The floor plan makes the open water views as its main focus. Cook the catch of the day over looking the waters that you just caught that prized fish in. Sit back and watch

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
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  /37

  $540,000 Sold Mar 04, 2025

  • 720 Sq Ft
  • $750/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1973

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  A LUSH HAVEN AWAITS YOU AND YOUR BOAT ... the property is a tropical delight with well-planned vegetation that creates amazing privacy and pleasant sitting areas. Enjoy the area's fantastic fishing, kayaking and dive spots from the 46 ft. long concrete seawall with step-down dock and fish cleaning station. There's no ignoring the welcoming sense of peace that one feels stepping onto the 372 sq.

  Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  27883 Coral Shores Rd, Little Torch Key, FL 33042
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  /38

  Est $2,534,850 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,181 Sq Ft

  2035 Long Beach Dr, Big Pine Key, FL 33043

  2035 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /10

  $1,400,000

  • Land

  655 E Shore Dr, Summerland Key, FL 33042

  Rare ROGO exempt opportunity to build your dream home on a cleared, massive canal front lot in highly sought-after Summerland Key! Enjoy direct ocean views, over 80 feet of ''L''-shaped concrete seawall, and deep water access ocean side with unobstructed boating off Niles Channel - offering the highest fixed bridge clearance in the Lower Keys for easy access between the Atlantic and backcountry

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  655 E Shore Dr, Summerland Key, FL 33042
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  /43

  $910,000 Sold Mar 04, 2025

  • 984 Sq Ft
  • $925/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  447 Pirates Rd, Summerland Key, FL 33042

  This wonderful canal front 3 bedroom and 2 bath home has been very well cared for and has excellent oceanside boating access. There are no bridges to the ocean and the canals are exceptionally clean. The kitchen is large with ample storage and the open living concept allows for great entertaining and family get togethers. The wrap around deck has large outdoor space and overlooks the canal and

  Jennifer Newman Truman & Co. (KW)

  447 Pirates Rd, Summerland Key, FL 33042
• 

  

  /14

  Est $1,743,290 Not Listed For Sale

  • 3 Beds

  1811 Long Beach Dr, Big Pine Key, FL 33043

  1811 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /30

  $540,000 Sold Mar 04, 2025

  • 816 Sq Ft
  • $662/SF
  • 256 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1985

  31353 Avenue E, Big Pine Key, FL 33043

  Florida Keys simple living can be yours in this Big Pine Key pool home. Nestled in the neighborhood, yet conveniently located to shopping and other amenities. An open concept with cathedral ceiling in Living, Dining and Kitchen areas. A laundry closet sits at one end of the kitchen and houses the washer and dryer. Off main living area there is a nice porch on the front side of this home, and is a

  Deni Heintzelman KeyIsle Realty

  31353 Avenue E, Big Pine Key, FL 33043
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  /2

  Est $865,568 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  22974 John Avery Ln, Summerland Key, FL 33042

  22974 John Avery Ln, Summerland Key, FL 33042
• 

  

  /47

  $979,000

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft

  29487 Ranger Ave, Big Pine Key, FL 33043

  Waterfront Living in Big Pine Key! Well-Built Canal Home in Prime Lower Keys Location: This 2-bedroom, 2-bath home features a bright open-concept living area that flows into a spacious covered and screened porch--perfect for relaxing or entertaining. Built with solid concrete block construction and topped with a 2018 metal roof, it offers lasting durability and peace of mind.Outside, the fully

  Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043

Showing Results 481 - 520, Page 13 of 18