358

Summerland Key, FL Homes for Sale

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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
  • /43

    $1,125,000

    • 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
  • /41

    $749,000

    • 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
  • /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
  • /7

    $195,000

    • Land
    • 1.02 Acres
    • $191,177 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 Coldwell Banker Schmitt RE Co.

    0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
  • /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
  • /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
  • /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
  • /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
  • /32

    $1,150,000

    • 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
  • /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
  • /79

    $869,999

    • 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
  • /10

    $335,000

    • Land

    0 Indies Rd, Ramrod Key, FL 33042

    Waterfront vacant lot located on Ramrod Key in an established canal community on the oceanside of the Lower Keys. This property offers boating access to the Atlantic with connectivity to Florida Bay. No building permit is currently in place; buyers may pursue development through ROGO or obtain a separate building right. Conveniently situated between Marathon and Key West, offering easy access to

    Jenifer Hirsch Bluescape Real Estate

    0 Indies Rd, Ramrod Key, FL 33042
  • /34

    $699,000

    • 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
  • /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
  • /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
  • /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
  • /50

    $2,500,000 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
  • /40

    $925,000

    • 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
  • /26

    $625,000

    • 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

    $324,999

    • 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. The value of this property is in the ROGO EXEMPT status. All the utilities are there and I can give you clear title for this property upon closing.Adjacent to this property is lots #35 & 36. They are also available making a total parcel of 18,000 square feet.

    Joseph Ordini Keller Williams Key West Compass Realty

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
  • /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
  • /61

    $1,795,000

    • 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
  • /2

    $115,000

    • Land
    • 1.27 Acres
    • $90,552 per Acre

    Lot 5 Mira Rd, Sugarloaf Key, FL 33042

    This lot is worth 4 points to be used towards obtaining a building permit in the ROGO system. Please contact Monroe County to verify information. Seller has several point lots for sale.

    Pamela Stangler Expert Realty LLC

    Lot 5 Mira Rd, Sugarloaf Key, FL 33042
  • /16

    $525,000

    • 1 Bed
    • 1 Bath
    • 557 Sq Ft

    31478 Avenue E, Big Pine Key, FL 33043

    Discover the quintessential Florida Keys lifestyle in this charming 1-bedroom, 1-bathroom island bungalow. Nestled in the heart of Big Pine Key, this home offers the perfect blend of cozy comfort and tropical serenity, making it an ideal full-time residence, weekend retreat, or savvy investment property.Home Highlights:Classic Bungalow Charm: An inviting open layout that maximizes space and

    Sabre Mendoza Coldwell Banker Schmitt RE Co.

    31478 Avenue E, Big Pine Key, FL 33043
  • /9

    $157,000

    • Land

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

    ROGO EXEMPT - Buildable lot! NO wait time, build now! Incredible opportunity to buy a piece of paradise in Florida keys! This property is 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.

    Steven Koleno Beycome of Florida, LLC

    29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
  • /34

    $980,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    131 Doubloon Ln, Summerland Key, FL 33042

    3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024).The downstairs area includes two large storage rooms, one of which features a fully functioning

    Jenifer Hirsch Bluescape Real Estate

    131 Doubloon Ln, Summerland 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
  • /74

    $3,250,000

    • 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 point lot on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. These point lots are extremely limited and among the most sought-after properties on Sugarloaf, prized for their expansive water frontage and commanding views of

    Lisa Swanson The Agency Florida Keys

    17385 Keystone Rd, Summerland Key, FL 33042
  • /21

    $875,000

    • 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
  • /46

    $2,800,000 New Construction

    • 4 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. Four roomy suites for your family

    Barbara Eads Barbara Eads Realty

    1553 Sunrise Dr, Big Pine Key, FL 33043
  • /51

    $837,500 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    29115 Rose Dr, Big Pine Key, FL 33043

    Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this home ensures both

    Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

    29115 Rose Dr, Big Pine Key, FL 33043
  • /57

    $1,595,000

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft

    25368 2nd St, Summerland Key, FL 33042

    Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

    Ally Kelley Ocean Sotheby's International

    25368 2nd St, Summerland Key, FL 33042
  • /27

    $350,000

    • 1 Bed
    • 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

    Jenifer Hirsch Bluescape Real Estate

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

    $800,000

    • Land
    • 0.18 Acre
    • $4,444,444 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
  • /22

    $1,150,000 Open Sat 11AM - 2PM

    • 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
  • /33

    $1,195,000

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

    17226 Jamaica Ln, Summerland Key, FL 33042

    Completely remodeled, turn key 3 bed 2 bath canal front home that.backs up to the nature's preserve. Home features large pool with a bar area and 300 square feet enclosed storage ,mature landscaping and concrete wall with automatic gate . Easy boating access from new concrete dock to Atlantic ocean side and the Gulf. Actively profitable Airbnb home

    Stephen Hachey

    17226 Jamaica Ln, Summerland Key, FL 33042
  • /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
  • /29

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft

    31525 Avenue A, Big Pine Key, FL 33043

    $525K Opportunity with so much potential. Privacy fence with 3 big double gates with access from both streets and no neighbor across the street. on Ave A. CBS 3bd/2bth ground level home. Central AC, Tile Floors, Double corner lot. 100 X 100. Lots of parking, or RV parking. Room for pool and entertaining. Patio deck area. Concrete pads for shed etc. Close to community park, public boat ramp nearby

    Rose Dell Keller Williams Key West Compass Realty

    31525 Avenue A, Big Pine Key, FL 33043

Showing Results 121 - 160, Page 4 of 9

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