Monroe, FL Homes

• 

  

  

  /45

  $819,000 Sold May 19, 2025

  • 1,584 Sq Ft
  • $517/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  25093 Center St, Summerland Key, FL 33042

  NEW WATERFRONT LISTING! MOTIVATED SELLER! Beautifully updated waterfront home with breathtaking views and 40' seawall. All major improvements are complete including roof, HVAC,impact windows, door, new kitchen and appliances with gas range, electrical panel,tankless water heater,and lower level kitchenette. DIRECT boating access to Niles Channel. The downstairs is a LEGAL nonconforming

  Susan Hawkinson Bascom Grooms Real Estate (KW)

  25093 Center St, Summerland Key, FL 33042
• 

  

  /2

  Est $925,532 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,792 Sq Ft

  29664 & 29670 Constitution Ave, Big Pine Key, FL 33040

  29664 & 29670 Constitution Ave, Big Pine Key, FL 33040
• 

  

  

  /52

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,313 Sq Ft

  31135 Hollerich Dr, Big Pine Key, FL 33043

  A beautifully kept home with amazing views of the Gulf, and easy boating access to some of the best waters the Florida Keys have to offer. Just four houses in from the Gulf of Mexico/Spanish Harbor, and just a few minutes access to open water! This is outdoor living at its best! With 70 ft of concrete dock space you have plenty of room for any size boat. Relax and enjoy your outdoor entertainment

  Wyatt Tucker Action Keys Realty of the Lower FL Keys LLC

  31135 Hollerich Dr, Big Pine Key, FL 33043
• 

  

  

  /46

  $540,000 Sold May 19, 2025

  • 960 Sq Ft
  • $562/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  31130 Avenue I, Big Pine Key, FL 33043

  Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is move-in ready with modern updates and coastal charm. A new metal roof, A/C, and hot water heater (2017) ensure peace of mind, while a fresh coat of interior paint adds a bright, inviting feel.Inside, you'll find custom cabinetry, stunning granite countertops, and a matching backsplash, creating a stylish

  Michael Sielicki Jr Real Broker, LLC

  31130 Avenue I, Big Pine Key, FL 33043
• 

  

  /2

  Not Listed For Sale

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

  29527 Constitution Ave, Big Pine Key, FL 33043

  29527 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /52

  $1,850,000

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft

  3746 Park Ave, Big Pine Key, FL 33043

  Welcome to your private paradise in the Lower Keys! This beautifully updated 2 bed, 2 bath two-story home offers complete privacy with no direct neighbors on all sides, making it a peaceful escape surrounded by nature and the charm of the Key Deer.Step outside to your tropical oasis featuring a brand-new concrete heated pool, concrete dock with a boat lift and jet ski lift, plus an elevated

  Kelsey Caputo Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  3746 Park Ave, Big Pine Key, FL 33043
• 

  

  /29

  $395,000 Sold May 19, 2025

  • Land

  • 78 Days On Market

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a 35' concrete seawall, dock posts, swim ladder, full hookups including water, sewer, and 30, 50 and 110 amp electric service. Enjoy the convenience of a

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 679 Sq Ft

  27962 Snapper Ln, Summerland Key, FL 33042

  27962 Snapper Ln, Summerland Key, FL 33042
• 

  

  /41

  $1,599,900

  • 4 Beds
  • 3 Baths
  • 1,704 Sq Ft

  951 Lagoon Dr, Summerland Key, FL 33042

  Need space for family and friends? Come see this 4 bedroom/ 3 Full Baths Summerland Cove Isles beautiful & spacious home today. Features open floor plan, large storage area below with a tackle room, metal roof, impact windows and shutters. French doors lead outdoors to a large screen porch overlooking the beautiful deep canal. Great kitchen area with a gas stove, family room, dining room, laundry

  Beata Sharpe Coldwell Banker Vanguard Realty

  951 Lagoon Dr, Summerland Key, FL 33042
• 

  

  /72

  $3,436,000 Sold May 16, 2025

  • 2,134 Sq Ft
  • $1610/SF
  • 30 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1996

  5460 Dorn Rd, Summerland Key, FL 33042

  Tucked away on Big Torch Key, one of the Florida Keys' best-kept secrets, this rare 3 acre luxurious custom estate offers the ultimate in privacy, tranquility and breathtaking waterfront views.With 357 feet of pristine shoreline on the Niles Channel and 180 views, this west-facing retreat is perfectly positioned for year-round sunset vistas. The design seamlessly connects over 4000 ft. of indoor

  Sandra Tuttle Island Welcome Real Estate

  5460 Dorn Rd, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 46th St, Summerland Key, FL 33042

  0 46th St, Summerland Key, FL 33042
• 

  

  /43

  $1,149,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  27415 Barbuda Ln, Ramrod Key, FL 33042

  Welcome to your waterfront retreat! This custom built solid concrete wall house was engineered to withstand a 175mph Cat 5 hurricane and proved it's hurricane resilience during hurricane Irma. This one owner canalfront home is nestled in one of Ramrod Key's most sought-after subdivisions. Designed with a spacious open floor plan and attention to detail, the home features 3 bedrooms and 2

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  27415 Barbuda Ln, Ramrod Key, FL 33042
• 

  

  /34

  $735,000 Sold May 16, 2025

  • 1,077 Sq Ft
  • $682/SF
  • 117 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  27373 Anguila Ln, Summerland Key, FL 33042

  Discover your dream home nestled in the coveted Breezeswept Beach Estates on beautiful Ramrod Key! This charming canal front sanctuary is perfect for boating lovers offering seamless access to the pristine waters of the Atlantic Ocean and the vibrant Looe Key Reef. This 3 bedroom home is move in ready. The kitchen has sleek granite countertops and updated appliances. The thoughtfully well

  Tracy Shields KeyIsle Realty

  27373 Anguila Ln, Summerland Key, FL 33042
• 

  

  /14

  Est $441,761 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
• 

  

  /40

  $1,225,000

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

  32734 Bimini Ln, Big Pine Key, FL 33043

  Escape to quintessential No Name Key to find this waterfront sanctuary. No Name Key is a secluded paradise; free of commercial development with fewer than 50 homes nestled in a one-of-a-kind conservation setting. This location offers unmatched stargazing and serene surroundings--yet it's just over 10 minutes from the amenities of Big Pine Key, 45 minutes from Marathon and 1 hour from Key West.

  Ally Kelley Ocean Sotheby's International

  32734 Bimini Ln, Big Pine Key, FL 33043
• 

  

  /40

  $1,350,000 Sold May 15, 2025

  • 1,315 Sq Ft
  • $1027/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  31254 Hollerich Dr, Big Pine Key, FL 33043

  Open views abound in this new 'Topsider' home, surrounded by water on three sides with 110 ft. of east-facing frontage overlooking Bogie Channel providing easy access to the back country and ocean. The property has 134 ft. of frontage along the 40 ft. wide canal on south side. One step inside the 1592 sq. ft. living area and there's no denying the views! With cathedral ceilings and abundant

  Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  31254 Hollerich Dr, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
• 

  

  /47

  $1,255,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  1021 Caribbean Dr E, Summerland Key, FL 33042

  COASTAL RETREAT in desirable SUMMERLAND KEY COVE situated on a prime canal! Calling all BOATERS that seek deep draft flow-through water - you'll be to the Atlantic or Gulf in minutes. Slip away to your Keys retreat - move-in ready! You'll love the remodeled kitchen and baths so you can spend your time splashing in the pool or sipping a cool drink under the tiki. Completely furnished with

  Donna Pezzi Keller Williams Key West Compass Realty

  1021 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /35

  $945,000 Sold May 15, 2025

  • 1,265 Sq Ft
  • $747/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1991

  17182 Starfish Ln W, Summerland Key, FL 33042

  Nestled in the heart of the stunning Florida Keys and perfect for anyone looking to escape the hustle and bustle of everyday life, this two-bedroom, two-bath home is a sanctuary of serenity and keys living. This property boasts an extra-large lot, providing ample space for outdoor activities, relaxation, and entertainment and there is lots of room for a pool and Tiki hut. The tropical landscaping

  Daniel Urban Century 21 Circle - Key West

  17182 Starfish Ln W, Summerland Key, FL 33042
• 

  /2

  Est $750,477 Not Listed For Sale

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

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
• 

  

  /8

  $1,100,000

  • 1 Bed
  • 4 Baths
  • 1,965 Sq Ft

  24931 Overseas Hwy, Summerland Key, FL 33042

  Seize this rare opportunity to own a prime working waterfront property with exceptional Highway visibility. This unique offering includes two waterfront buildings located at 24931 & 24933 Overseas Highway in Summerland Key, each with separate water, electric, and sewer connections for added flexibility. Situated on a 10,673 SF lot, the property features a 813 SF building, a 1,152 SF building, and

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  24931 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /32

  $700,000 Sold May 14, 2025

  • 960 Sq Ft
  • $729/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  226 Newfound Blvd, Big Pine Key, FL 33043

  Nestled on a quiet dead-end street, this 2-bed, 2-bath stilted home offers privacy, low-maintenance living, and a relaxed Keys lifestyle. With county and state-owned land across both the canal and the front of the home, you'll enjoy lush, unobstructed views with no future development in sight. Step inside to a fully-furnished (excluding artwork), open-concept living space featuring beautiful wood

  Madeleine Lowe Expert Realty LLC (HQ)

  226 Newfound Blvd, Big Pine Key, FL 33043
• 

  

  /23

  Est $804,513 Not Listed For Sale

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

  27225 Mariposa Rd, Summerland Key, FL 33042

  27225 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /58

  $1,075,000

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft

  28550 Doubloon Rd, Summerland Key, FL 33042

  Look no further for your Florida Keys dream home. This home is located in the highly desirable Jolly Roger Estates on Little Torch Key where fishing and diving are in your backyard.Don't miss out on this rare opportunity! After more than two decades, this spacious waterfront residence is finally available! Featuring a 50-foot boat dock, this large nearly 2400 square foot Canal front home awaits

  Kelly Randin RE/MAX All Keys Real Estate

  28550 Doubloon Rd, Summerland Key, FL 33042
• 

  

  /92

  $1,050,000 Sold May 14, 2025

  • 1,232 Sq Ft
  • $852/SF
  • 129 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  27436 Tobago Ln, Summerland Key, FL 33042

  Welcome to your dream waterfront oasis! This immaculate three-bedroom, two-bathroom home, built in 2020, offers a perfect blend of elegance and luxury. Meticulously maintained, this modern residence boasts ample privacy and quick boating access, making it an ideal retreat for water enthusiasts. As you step inside, you'll be greeted by a spacious open floor plan that seamlessly connects the

  Justyn Ewald Expert Realty LLC (HQ)

  27436 Tobago Ln, Summerland Key, FL 33042
• 

  /2

  Est $826,150 Not Listed For Sale

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

  27087 Angelfish Rd, Summerland Key, FL 33042

  27087 Angelfish Rd, Summerland Key, FL 33042
• 

  

  /47

  $1,165,000

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

  29051 Magnolia Ln, Big Pine Key, FL 33043

  Welcome to 29051 Magnolia Ln, Big Pine Key, FL! This home offers a 2-bedroom, 2-bath main area and a pre-FIRM permitted 480 sq. ft. studio/MIL suite with a full bath. Nestled on a 5,100 sq. ft. lot, this concrete home is ideal for island living. The chef's kitchen features stainless steel appliances, premium counters, and breakfast bar. Enjoy a screened porch overlooking the canal, complete with

  Yvette Toledo-Baste Compass Florida, LLC.

  29051 Magnolia Ln, Big Pine Key, FL 33043
• 

  

  /58

  $2,025,000 Sold May 13, 2025

  • 1,292 Sq Ft
  • $1567/SF
  • 85 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated

  Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /69

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

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

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

  

  /39

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  164 Tortuga Ln, Summerland Key, FL 33042

  Welcome to 164 Tortuga Lane, a solid concrete stilted home perfectly positioned on a wide canal with quick access to open water. This move-in-ready property features 3 bedrooms, 2 bathrooms, 1,400 sq ft of living space, and a 6,000 sq ft lot.Highlights include: Private in-ground pool Metal roof (2018) with peel & stick underlayment Full hurricane protection with accordion shutters 10,000 lb boat

  Kathryn Baldwin Berkshire Hathaway HomeServices Knight & Gardner Realty

  164 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /37

  $500,000 Sold May 09, 2025

  • 936 Sq Ft
  • $534/SF
  • 143 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1975

  29162 Iris Dr, Big Pine Key, FL 33043

  CBS home on two lots with a county owned lot to the west which means there is a vacant lot on each side of the home. Located on a 50-foot-wide canal with a cut in boat slip. Only a short ride out to open water. Quiet street with lots of privacy, new roof in 2023, fenced yard. Close to shopping, Bahia Honda state park and beach and a short ride to Key West. Neighborhood boat ramp, lots of wildlife

  John Nazzaro Keller Williams Realty Premier Properties

  29162 Iris Dr, Big Pine Key, FL 33043
• 

  

  /14

  Est $385,000 Not Listed For Sale

  29167 Cactus Ln, Big Pine Key, FL 33043

  29167 Cactus Ln, Big Pine Key, FL 33043
• 

  

  /42

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  22737 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with your very own

  Terry Garcia Keller Williams Key West Compass Realty

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /46

  $699,000 Sold May 08, 2025

  • 1,200 Sq Ft
  • $582/SF
  • 35 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2015

  25022 Palm Ln, Summerland Key, FL 33042

  Coastal Charm in Summerland Key - Elevated Island LivingWelcome to 25022 Palm Lane, a beautifully elevated 3-bedroom, 2-bathroom home in the heart of Summerland Key, offering the perfect blend of modern comfort and island charm. Situated on a spacious lot with tropical landscaping and low-maintenance gravel yard, this home is ideal for those seeking a serene Keys retreat.Step inside to find a

  Stephany Duvall Engel & Volkers Marathon

  25022 Palm Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  BK 3 Lot 4 Antigua Ln, Ramrod Key, FL 33042

  BK 3 Lot 4 Antigua Ln, Ramrod Key, FL 33042
• 

  

  /43

  $1,275,000

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  1032 Caribbean Dr E, Summerland Key, FL 33042

  The ''COPPER TOP'' - Solid construction with a metal roof located on a beautiful flow-through canal in Summerland Key Cove. This 3 bedroom, 2 bath home checks all the boxes. You'll love the modern remodeled kitchen with vaulted ceilings in the living area, tiled floors throughout and a screened in balcony that allows you to open up the house and enjoy the breezes. Furnished for your

  Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /115

  $12,250,000 Sold May 07, 2025

  • 4,888 Sq Ft
  • $2506/SF
  • 44 Days On Market

  • 7 Beds
  • 6 Baths
  • Built 2019

  785 Sawyer Dr, Cudjoe Key, FL 33042

  Welcome to Cypress Point, an exceptional and highly private, 7-Bed, 6-Bath, 4,888 Sq Ft oceanfront estate spanning almost a full acre on Cudjoe Key, where luxury and coastal beauty uniquely blend. This custom D'Asign Source built home is privately nestled behind an electric gate and boasts the finest finishes and amenities which include an oceanfront pool, outdoor theater, 6-hole golf green,

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  785 Sawyer Dr, Cudjoe Key, FL 33042
• 

  /2

  Est $131,000 Not Listed For Sale

  • Studio

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  Lot 2 Egret Ln, Big Pine Key, FL 33043
• 

  

  /49

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  27426 Martinique Ln, Summerland Key, FL 33042

  Motivated seller offers new price reduction on this elevated 3 bedroom 2 bath home with 60 ft concrete dock and 120 ft waterfront! Boater's dream with canal access to open water and NO bridges. Updates include roof, impact windows and doors, complete kitchen remodel, and bath in 2018. Central A/C replaced in 2024. Exterior painted 2022. Screened porch offers perfect place to start your

  Susan Hawkinson Bascom Grooms Real Estate (KW)

  27426 Martinique Ln, Summerland Key, FL 33042
• 

  

  /22

  $400,000 Sold May 07, 2025

  • 1,187 Sq Ft
  • $337/SF
  • 72 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  357 Ships Way, Big Pine Key, FL 33043

  Nestled in the highly sought-after Pine Channel Estates neighborhood, this 2-bedroom, 2-bath home offers incredible potential for those looking to put their personal touch on a Florida Keys retreat. Though it's a fixer-upper, the property boasts a spacious layout and plenty of room for improvement, making it the perfect opportunity to create your dream home in paradise.The large lot offers ample

  Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

  357 Ships Way, Big Pine Key, FL 33043

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