Summerland Key, FL Homes for Sale

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  /88

  $750,000

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

  40 Munson Ave, Summerland Key, FL 33042

  Welcome home to your peaceful island retreat! This stunning 3-bed, 2-bath home is move-in ready & full of charm. Enjoy soaring vaulted ceilings, an open layout, & a bright kitchen with Quartz countertops, stainless steel appliances, & large island with ample seating. Recent updates include new luxury vinyl plank flooring, new upgraded refrigerator, & new outdoor bar & sitting area perfect for

  Lindsay Ryan EXP Realty LLC

  40 Munson Ave, Summerland Key, FL 33042
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  /60

  $949,900

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

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  Soak up the Keys lifestyle from this bright, modern 3-bed/2-bath home in the coveted oceanside community of Breezeswept Beach Estates on Ramrod Key. Built in 2008 with high-end finishes--sleek cabinetry, quality flooring, and fresh, airy decor--this turnkey residence is neat, clean, and move-in ready.Outdoor living shines here: two open decks (front and back) capture breezes and sunset glow,

  Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
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  /39

  $699,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  30881 Witters Ln, Big Pine Key, FL 33043

  Updated cottage with all the necessities you need with minimal maintenance. This CBS home has a newer metal roof, mini split A/c, updated kitchen on 3 lots only a very short ride to Boggie Channel, the only market channel to the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key and surrounding waters

  John Nazzaro Keller Williams Realty Premier Properties - Kendall

  30881 Witters Ln, Big Pine Key, FL 33043
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  /54

  $1,925,000

  • 4 Beds
  • 3 Baths
  • 1,440 Sq Ft

  1082 Bay Dr, Summerland Key, FL 33042

  Rare Yacht-Ready Waterfront? It doesn't get better than this in the Lower Florida Keys! Embraced by the emerald waters of the American Caribbean, pristine, wide and flow-through canals, and nearly 200 feet of concrete seawall sits this extraordinary opportunity to own prime waterfront. A prized combination coveted by the most discerning boating enthusiasts. Sitting on an oversized 7,900 sq. ft.

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  1082 Bay Dr, Summerland Key, FL 33042
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  /59

  $1,569,999 New Construction

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
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  /45

  $7,000,000

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

  0 Melody Key Unit 616249, Summerland Key, FL 33042

  An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

  Scott Forman Royal Palms Realty (KW)

  0 Melody Key Unit 616249, Summerland Key, FL 33042
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  /46

  $735,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  30920 Baileys Ln, Big Pine Key, FL 33043

  Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water--just minutes to both the Gulf and the Atlantic. Situated on a spacious double lot, the property includes a 30 ft. Step down boat slip cut in, ideal for docking your boat and enjoying effortless days on the water.Designed for seamless indoor-outdoor living, the home

  Deni Heintzelman KeyIsle Realty

  30920 Baileys Ln, Big Pine Key, FL 33043
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  /30

  $362,000

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  27960 Porgie Path, Little Torch Key, FL 33042

  Canal Front Coral Shores Estates! This 3 Bedroom home with Open Water views of South Pine Channel has a wonderful Swimming Canal ,perfect for kayaking, SUP, and can be easily accessed from the beautiful large new deck- with ladder access to the water. The front of the yard has new fencing, and room to park several cars off street. The inside has 3 bedrooms and a bath, and 2 living room areas.

  Elaine Coyle Keller Williams Key West Compass Realty

  27960 Porgie Path, Little Torch Key, FL 33042
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  /7

  $4,325,000 New Construction

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

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

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
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  /43

  $1,135,000

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

  22837 Calico Jack Cir, Summerland Key, FL 33042

  Seller says Bring Offers ! Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland Key, FL 33042
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  /41

  $795,000

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

  251 Pelican Ln, Big Pine Key, FL 33043

  Tropical Retreat on Two Lots. Discover your slice of paradise with this lovely updated concrete block home, perfectly positioned on an oversized property with serene canal frontage. Move-in ready, meticulously maintained, this home offers both comfort and functionality. Inside, you'll love the cheerful white kitchen with granite counters and backsplash, flowing seamlessly into the open living and

  Sunnie San Lorenzo KeyIsle Realty

  251 Pelican Ln, Big Pine Key, FL 33043
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  /2

  $52,000

  • Land

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
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  /7

  $225,000

  • Land
  • 1.02 Acres
  • $220,589 per Acre

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042

  Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. It is a special lot that features mature trees. Near Sugarloaf School. 25 minutes to Key West.

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
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  /15

  $1,450,000

  • Land
  • 2.29 Acres
  • $633,190 per Acre

  1261 Avenue A, Big Pine Key, FL 33043

  An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west

  Ally Kelley Ocean Sotheby's International

  1261 Avenue A, Big Pine Key, FL 33043
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  /11

  $249,000 New Construction

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

  231 Pelican Ln, Big Pine Key, FL 33043

  The price is for the lot AND permit. Pre-construction showing a picture of the modular that is permitted. Make your changes now before price increases with work conducted OR purchase the property with the permit and finish it on your own. *Approved ROGO Allocation and Active Building Permit as of February 25, 2025. Building permit is ready to be picked up. Permit number: SFDUP-2023-0113 is

  Donna Pezzi Keller Williams Key West Compass Realty

  231 Pelican Ln, Big Pine Key, FL 33043
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  /24

  $265,000

  • Land

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
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  /24

  $385,000

  • Land

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

  The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeyEscape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig and start relaxing

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
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  /55

  $2,300,000 New Construction

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

  30995 Watson Blvd, Big Pine Key, FL 33043

  FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  30995 Watson Blvd, Big Pine Key, FL 33043
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  /68

  $1,895,000

  • 3 Beds
  • 3.5 Baths
  • 2,295 Sq Ft

  1136 W Shore Dr, Big Pine Key, FL 33043

  Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking

  Beata Sharpe Coldwell Banker Vanguard Realty

  1136 W Shore Dr, Big Pine Key, FL 33043
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  /40

  $2,450,000

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

  1330 Sugarloaf Blvd, Summerland Key, FL 33042

  Luxury Waterfront Living on Sugarloaf KeyExperience the epitome of island elegance in this beautifully completely renovated waterfront retreat on desirable Sugarloaf Key. This three-bedroom, two-bath home evething is brand NEW home showcases high-end finishes throughout, blending modern luxury with laid-back coastal charm. The open-concept living area flows seamlessly onto an expansive outdoor

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1330 Sugarloaf Blvd, Summerland Key, FL 33042
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  /24

  $580,175

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

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

  Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

  Sarah Dolson Keller Williams Key West Compass Realty

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

  $875,000

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  19512 Aztec St, Summerland Key, FL 33042

  Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  19512 Aztec St, Summerland Key, FL 33042
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  /35

  $710,000

  • 3 Beds
  • 1.5 Baths
  • 1,247 Sq Ft

  29283 Coconut Palm Dr, Big Pine Key, FL 33043

  Welcome to Coconut Palm Drive -- a hidden gem in one of Big Pine Key's peaceful residential neighborhoods. This 3-bedroom, 1.5-bath island home offers vaulted ceilings, crown molding, and an open-concept layout that brings in natural light and a spacious feel. The tropical backyard is fully fenced for privacy and features mature banana trees. A generous downstairs storage area offers endless

  Stephany Duvall Engel & Volkers Marathon

  29283 Coconut Palm Dr, Big Pine Key, FL 33043
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  /2

  $379,000

  • Land

  27463 Antigua Rd, Ramrod Key, FL 33042

  Exceptional Opportunity to develop this 6200-sf canal front Ramrod Key Lot with Plans in the super relaxed Breezeswept Beach Estates community! Ideal Tier 3 Canal. Currently has 38 Rogo points and plans for an exceptional home, dock, and lift. Building Permit application is finalized and approved. 3/2 elevated home that is a certified green build. Just need Rogo award. Great Open water ocean

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  27463 Antigua Rd, Ramrod Key, FL 33042
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  /43

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft

  30461 Poinciana Rd, Big Pine Key, FL 33043

  Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 bath home, with an office, features a vaulted ceiling, brand new mini split air condition units and plenty of windows and French doors that allow light to fill the home. The large primary bedroom has a screened in porch off the back perfect for relaxing. Also, in the rear of the home is an attached, private

  Francesca Santiago Keller Williams Realty Professionals (KW)

  30461 Poinciana Rd, Big Pine Key, FL 33043
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  /12

  $599,000

  • Land
  • 0.27 Acre
  • $2,183,468 per Acre

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042

  **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

  Daiane Sardinas Carvalho Centennial Realty Group, LLC

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042
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  /28

  $1,950,000

  • 3 Beds
  • 3 Baths
  • 1,797 Sq Ft

  860 Lagoon Dr, Summerland Key, FL 33042

  This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThis home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

  Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  860 Lagoon Dr, Summerland Key, FL 33042
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  /65

  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  165 Cutlass Ln, Summerland Key, FL 33042

  Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

  Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
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  /16

  $645,000

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft

  29188 Tulip Ln, Big Pine Key, FL 33043

  Nestled at the quiet end of a peaceful street, this beautifully maintained home offers the blend of island charm, privacy, and modern comfort. Surrounded by graceful Areca palms and bordered by county land on two sides, the property feels like a serene tropical oasis. Step inside to find soaring cathedral ceilings that create a bright, airy atmosphere throughout the open living area. The updated

  Steven Koleno Beycome of Florida, LLC

  29188 Tulip Ln, Big Pine Key, FL 33043
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  /36

  $1,189,000

  • 4 Beds
  • 3 Baths
  • 1,896 Sq Ft

  31569 Avenue D, Big Pine Key, FL 33043

  Welcome to your Florida Keys fortress! This newly constructed 4-bedroom, 3-bath concrete home offers unmatched durability, modern finishes, and gorgeous open water views from porches on both levels. Just a few hundred feet from deep water boating, this property provides the closest boat access to the world-famous Bahia Honda Bridge of any neighborhood in the Lower Keys, navigating to the ocean or

  Austin Kimbler Expert Realty LLC (HQ)

  31569 Avenue D, Big Pine Key, FL 33043
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  /50

  $1,997,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  711 W Indies Dr, Summerland Key, FL 33042

  Stunning Brand New Open Water CBS Construction Home on beautiful Ramrod Key, FL. Minutes to the Atlantic Ocean and World Famous Looe Key the #1 Dive destination in the Continental US.Discover coastal living at its finest with this brand-new 4-bedroom, 3-bathroom home nestled on the sparkling open waters of Ramrod Key. Boasting 2,000 square feet of thoughtfully designed living space, this home

  Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
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  /26

  $669,000

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft

  29030 Iris Dr, Big Pine Key, FL 33043

  This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and

  Justyn Ewald Expert Realty LLC (HQ)

  29030 Iris Dr, Big Pine Key, FL 33043
• 

  /2

  $350,000

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
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  /28

  $980,000

  • 4 Beds
  • 3 Baths
  • 1,457 Sq Ft

  31441 Avenue F, Big Pine Key, FL 33043

  This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the perfect blend of comfort and style for a growing family. Step into the open-concept living area with vaulted ceilings, creating an airy, welcoming atmosphere. The chef-inspired kitchen features beautiful quartz countertops and stainless steel appliances, perfect for cooking and entertaining. Tile floors

  Austin Kimbler Expert Realty LLC (HQ)

  31441 Avenue F, Big Pine Key, FL 33043
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  /20

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  29678 Enterprise Ave, Big Pine Key, FL 33043

  Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

  Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  29678 Enterprise Ave, Big Pine Key, FL 33043
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  /61

  $1,970,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  876 Gulf Dr, Summerland Key, FL 33042

  Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal

  Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
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  /6

  $163,000

  • Land

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

  ROGO EXEMPT - Buildable lot! Incredible opportunity to buy a piece of paradise in Florida keys! This residence offers a unique blend of coastal living and modern amenities. Appropriate for those seeking a tranquil retreat while still being conveniently close to local attractions and the beautiful waters of the Florida Keys. Discover the lifestyle you've been dreaming of here. Low HOA fee, just

  Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
• 

  

  /39

  $969,000

  • 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
• 

  

  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

Showing Results 81 - 120, Page 3 of 9