Summerland Key, FL Homes for Sale

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  /9

  $475,000

  • Land

  27460 W Indies Dr, Ramrod Key, FL 33042

  Anay Ramos Miami New Realty

  27460 W Indies Dr, Ramrod Key, FL 33042
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  /15

  $1,395,000

  • Land
  • 2.29 Acres
  • $609,173 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 Realty

  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

  $350,000

  • Land

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

  The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeySeller says bring offers..Escape 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

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
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  /2

  $275,000

  • Land

  0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

  Builders and Developers take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

  Pamela Stangler Expert Realty LLC

  0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
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  /34

  $469,000

  • 1 Bed
  • 1.5 Baths
  • 735 Sq Ft

  701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

  Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home offers

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
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  /32

  $1,125,000

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft

  27821 Leeward South Rd, Little Torch Key, FL 33042

  Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan living room with an abundance of space for

  Tracy Shields KeyIsle Realty

  27821 Leeward South Rd, Little Torch 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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  /76

  $859,999

  • 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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  /4

  $300,000

  • Land

  27426 Martinique Ln, Summerland Key, FL 33042

  Vacant 6,000 SF lot in desirable Ramrod Key, ideally positioned near the world-class Looe Key Reef and just a five-minute boat ride to Picnic Island. This property offers an exceptional opportunity to build in one of the Lower Keys' most sought-after lifestyle locations. Walking distance to local favorites including The Tiki Bar and Boondocks Grille & Draft House. Buyer to obtain building permit

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
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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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  /40

  $899,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large island

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28571 Buccaneer Rd, Summerland Key, FL 33042
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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,

  Thomas Carden Keys to the Coast Real Estate LLC

  29678 Enterprise Ave, Big Pine Key, FL 33043
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  /17

  $199,900

  • 2 Beds
  • 1 Bath
  • 300 Sq Ft

  29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043

  Live affordably or invest wisely in this 8 year old tiny home located on its own private lot in Big Pine Key, Lower Keys. This 24 ft Cornerstone model with two lofts is in perfect condition, thoughtfully maintained, and completely move in ready. The exterior has been newly repainted, and the interior is impeccably kept, showing pride of ownership throughout. The open living space includes a

  Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  29859 Overseas Hwy Unit LOT 15, Big Pine Key, FL 33043
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  /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
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  /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
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  /74

  $2,995,000

  • 4 Beds
  • 4 Baths
  • 1,804 Sq Ft

  17385 Keystone Rd, Summerland Key, FL 33042

  Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most

  Lisa Swanson The Agency Florida Keys

  17385 Keystone Rd, Summerland Key, FL 33042
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  /49

  $985,000

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
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  /14

  $258,000

  • Land

  701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

  Venture Out RV Lot - Prime Location Near the StoreOpportunity to own a spacious RV lot in the highly desirable Venture Out community in Cudjoe Key. This pie-shaped lot measures approximately 65' x 67' x 63', offering generous space for your RV, outdoor living area, and parking.Conveniently located just a short distance from the community store and amenities, this lot provides easy access to

  Lisa Carter Florida Keys Realty, Inc.

  701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
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  /110

  $2,800,000 New Construction

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

  1553 Sunrise Dr, Big Pine Key, FL 33043

  Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Three roomy suites for your family

  Barbara Eads Barbara Eads Realty

  1553 Sunrise Dr, Big Pine Key, FL 33043
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  /27

  $350,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

  Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
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  /7

  $799,990

  • Land
  • 0.18 Acre
  • $4,444,389 per Acre

  28525 Jolly Roger Dr, Little Torch Key, FL 33042

  RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

  Fazana Haniff FHG Realty, LLC.

  28525 Jolly Roger Dr, Little Torch Key, FL 33042
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  /47

  $445,000

  • Land

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

  ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
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  /22

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  1331 Hudgins Dr, Summerland Key, FL 33042

  Location, Location and Location Enter the Palm Tree Stained-glass Impact door to 24-inch Travertine floors and Nine-foot ceilings throughout. The Master Bedroom has double French doors With a Tropical Stained-glass Floral Design. 1060 sq-ft 2 Bedroom 2 Bath, nine-foot ceilings, All Travertine/Tile Bathrooms with Skylights, heaters and extra storage, finished closets and two waterside triple

  Camilo Perez Home Sold Realty, LLC

  1331 Hudgins Dr, Summerland Key, FL 33042
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  /29

  $639,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  31124 Avenue C, Big Pine Key, FL 33043

  Welcome to an inviting, well-priced island home in Big Pine Key, perfectly suited for families, military buyers, or anyone seeking relaxed Florida Keys living with modern upgrades already done. This beautifully renovated 2-bedroom, 2-bath home was thoughtfully updated in 2024 and blends comfort, privacy, and tropical charm.Inside, you'll find new luxury vinyl flooring throughout, a refreshed

  Dawn McComish Lokation Real Estate

  31124 Avenue C, Big Pine Key, FL 33043
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  /9

  $3,500,000

  • Land

  19657 Seminole St, Sugarloaf Key, FL 33042

  Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

  Derek Epperly Engel & Volkers Key West

  19657 Seminole St, Sugarloaf Key, FL 33042
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  /60

  $2,499,000

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft

  556 Caribbean Dr E, Summerland Key, FL 33042

  The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
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  /24

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  853 Indies Rd, Summerland Key, FL 33042

  Move right into this well-maintained 3-bedroom, 2-bath canal front home, built in 2006 and cared for with pride. The bright, open layout features a split floor plan that offers comfortable space for everyday living and entertaining.The primary bedroom includes an en-suite bath and a versatile bonus room -- ideal for a home office, nursery, or cozy retreat. Step outside to enjoy peaceful canal

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  853 Indies Rd, Summerland Key, FL 33042
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  /35

  $799,000

  • 3 Beds
  • 3 Baths
  • 1,224 Sq Ft

  3672 Fox St, Big Pine Key, FL 33043

  Discover a peaceful Keys escape on a quiet canal in Big Pine Key. This attractive 3-bedroom, 3-bath home blends relaxed, nature-forward living with modern comforts.Bright, open living area with high ceilingsUpdated kitchen with stainless steel appliances, granite counters, and ample cabinetry. Private master suite with en-suite bath and direct balcony access.Two additional bedrooms ideal for

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  3672 Fox St, Big Pine Key, FL 33043
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  /53

  $1,710,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
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  /25

  $695,000

  • Land

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

  Barbara Eads Barbara Eads Realty

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042
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  /49

  $329,000

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
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  /18

  $1,499,000 New Construction

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

  27374 Guadaloupe Ln, Summerland Key, FL 33042

  New Construction coming Fall 2026. Step into the laid-back charm of the Florida Keys with this spacious 1,500 sqft home, perfectly situated along a peaceful boating canal in the Lower Keys, a short boat ride out to Looe Key Reef. 12x22 Swimming Pool and luscious landscaping.Inside the home: An open, airy floor plan that allows you to spread out and personalize your living space. A seamless

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27374 Guadaloupe Ln, Summerland Key, FL 33042
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  /31

  $624,900

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  30023 Pine Channel Rd, Big Pine Key, FL 33043

  Discover tranquil Keys living at 30023 Pine Channel Rd, a charming 3-bedroom, 2-bathroom home offering peaceful seclusion with effortless access to the Overseas Highway. Set on a generous lot and surrounded by mature, beautifully established trees, this property delivers the perfect blend of privacy, nature, and convenience.Step inside to find 1,218 sq ft of comfortable living space. The

  Sam Williams Coldwell Banker Schmitt Real Estate Co.

  30023 Pine Channel Rd, Big Pine Key, FL 33043
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  /82

  $3,699,000

  • 4 Beds
  • 3.5 Baths
  • 1,744 Sq Ft

  17183 Coral Dr, Summerland Key, FL 33042

  Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

  Jan Fritz Coldwell Banker Schmitt RE Co.

  17183 Coral Dr, Summerland Key, FL 33042
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  /2

  $85,000

  • Land

  Vacant Central Ave, Big Pine Key, FL 33043

  Tier 2 parcel with potential eligibility for ROGO points toward future building permits in Monroe County. Buyer to verify ROGO point availability and requirements with Monroe County. Adjacent lot is for sale MLS#618997

  Deni Heintzelman KeyIsle Realty

  Vacant Central Ave, Big Pine Key, FL 33043
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  /43

  $880,000

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft

  3686 Gulfstream St, Big Pine Key, FL 33043

  Key Deer, Quick Access to Pine Channel, Canal Views & Updated Island Living: Your Florida Keys Dream Awaits!Imagine: breathtaking sunsets painting the sky, the gentle presence of Key Deer just outside your fence, and the tranquility of canal-front living in the heart of the National Key Deer Refuge. This charming 2-bedroom, 2-bathroom home offers a rare opportunity to live in harmony with nature

  Robert Smithwick Engel & Volkers Marathon

  3686 Gulfstream St, Big Pine Key, FL 33043
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  /52

  $3,899,000

  • 6 Beds
  • 6 Baths
  • 3,029 Sq Ft

  1557 Long Beach Dr, Big Pine Key, FL 33043

  Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meets income opportunity. This beautifully updated waterfront property allows you to live the Florida Keys lifestyle while hosting it or operate a turnkey hospitality investment in one of the most sought-after settings in the Lower Keys. The property has undergone an extensive renovation over

  Surelis Yanes Miami Portfolio Collection

  1557 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /66

  $2,795,000

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

  Greg MacLaren Internet Realty of the Florida Keys

  333 Indies Rd, Ramrod Key, FL 33042

Showing Results 121 - 160, Page 4 of 8