327

Summerland Key, FL Homes for Sale

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  • 701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
    /55

    $925,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

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

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

    Bobby Coe RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
  • 31131 Avenue D, Big Pine Key, FL 33043
    31131 Avenue D, Big Pine Key, FL 33043
    31131 Avenue D, Big Pine Key, FL 33043
    /26

    $459,000

    • 2 Beds
    • 1 Bath
    • 754 Sq Ft

    31131 Avenue D, Big Pine Key, FL 33043

    Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Bedroom 1 bathroom with a bonus office/guest room opening to a large screened patio and spacious back yard. This Home is a true Conch home Constructed with Miami Dade Pine originally built in Key West then moved to Big Pine to join the first few homes built on. the Island. Impact doors, new shutters, new roof,

    Heather Mason Coastal Collection Real Estate Inc.

    31131 Avenue D, Big Pine Key, FL 33043
  • 27453 Antigua Rd, Ramrod Key, FL 33042
    27453 Antigua Rd, Ramrod Key, FL 33042
    27453 Antigua Rd, Ramrod Key, FL 33042
    /20

    $345,000

    • Land

    27453 Antigua Rd, Ramrod Key, FL 33042

    Building permit in-process for a 3 bedroom / 2 bath stilted single family residence. 1320 square feet. The plans are for an Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment, great for your insurance rates.There are plans in review for an 8'x40' dock with the Army Corp.

    Donna Pezzi Keller Williams Key West Compass Realty

    27453 Antigua Rd, Ramrod Key, FL 33042
  • 701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    /59

    $549,000

    • 2 Beds
    • 2 Baths
    • 860 Sq Ft

    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
  • 31042 Hibiscus Dr, Big Pine Key, FL 33043
    31042 Hibiscus Dr, Big Pine Key, FL 33043
    31042 Hibiscus Dr, Big Pine Key, FL 33043
    /42

    $689,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    31042 Hibiscus Dr, Big Pine Key, FL 33043

    Assumable interest rate at 4.8% for qualified buyers! This exceptional property boasts an array of features that provides the perfect blend of comfort and tranquility. The surrounding county-owned land ensures a sense of seclusion and no future building. As you step inside, you'll be greeted by the soaring cathedral ceilings, which create a sense of airiness and freedom, perfectly complemented by

    Deni Heintzelman KeyIsle Realty

    31042 Hibiscus Dr, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    /18

    $470,000

    • Land

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

    Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
  • 248 Yardarm Rd, Cudjoe Key, FL 33042
    248 Yardarm Rd, Cudjoe Key, FL 33042
    /2

    $80,000

    • Land

    248 Yardarm Rd, Cudjoe Key, FL 33042

    This is a listing for two transferable lots. lots # 35 & 36 each lot is 6000 sq. ft.

    Joseph Ordini Keller Williams Key West Compass Realty

    248 Yardarm Rd, Cudjoe Key, FL 33042
  • 30351 Flamingo Ln, Big Pine Key, FL 33043
    30351 Flamingo Ln, Big Pine Key, FL 33043
    30351 Flamingo Ln, Big Pine Key, FL 33043
    /10

    $279,999

    • Land

    30351 Flamingo Ln, Big Pine Key, FL 33043

    RemarksRemarks:Excellent neighborhood! Cleared land surrounding $800,000 homes plus range. In Rogo, Tier II . All homes are required to be CBS and no modular homes allowed. Plans for a 3 bedroom 2 bath home have been approved (county permits alterations to the house plans before you build, enabling you to design to your own specific needs). PERMIT Number is 16103833. Annual low association of

    Ana Tavel Paz Coldwell Banker - Pinecrest

    30351 Flamingo Ln, Big Pine Key, FL 33043
  • 270 Airport Dr S, Summerland Key, FL 33042
    270 Airport Dr S, Summerland Key, FL 33042
    270 Airport Dr S, Summerland Key, FL 33042
    /56

    $2,200,000

    • 3 Beds
    • 3 Baths
    • 1,275 Sq Ft

    270 Airport Dr S, Summerland Key, FL 33042

    A rare aviation-and-waterfront opportunity in the private Summerland Key Airport community, this canal-front home includes a private hangar--an exceptionally scarce feature, with only four hangar homes (excluding this one) coming to market in the past decade. Optional access to the private airstrip is available for just $100 per month, making this property ideal for pilots, boaters, fishermen,

    Solaris Gregory Expert Realty LLC (HQ)

    270 Airport Dr S, Summerland Key, FL 33042
  • 1185 Hakluyt Ln, Summerland Key, FL 33042
    1185 Hakluyt Ln, Summerland Key, FL 33042
    1185 Hakluyt Ln, Summerland Key, FL 33042
    /45

    $1,399,000

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

    1185 Hakluyt Ln, Summerland Key, FL 33042

    Location, location, location!Situated on the desirable southern tip of Cudjoe Key, this exceptional oceanside property offers everything you could dream of in a true Florida Keys retreat. Enjoy breathtaking open-water views from every room and an inviting open floor plan featuring a newer kitchen, updated appliances, modern bathrooms, refreshed flooring, and upgraded impact windows and

    Greg MacLaren Internet Realty of the Florida Keys

    1185 Hakluyt Ln, Summerland Key, FL 33042
  • 27415 Barbuda Ln, Ramrod Key, FL 33042
    27415 Barbuda Ln, Ramrod Key, FL 33042
    27415 Barbuda Ln, Ramrod Key, FL 33042
    /43

    $1,099,000

    • 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
  • LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
    LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
    LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
    /13

    $85,000

    • Land
    • 4 Acres
    • $21,250 per Acre

    LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

    Offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish, tarpon, permit and redfish nearby. Located on Southwest end of Little Knockemdown Key. Accessible by kayak, paddle board and shallow draft vessels. Privacy and nature abound here on Little Knockemdown Key - No roads or

    Banks Prevatt Coldwell Banker Schmitt RE Co.

    LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
  • Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
    /3

    $449,000

    • Land
    • 0.34 Acre
    • $1,303,896 per Acre

    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

    Oversized lot in gorgeous Sugarloaf Key with 15,000 Square feet ready for you to enter into the ROGO system. This sale comes with a ROGO Point Letter from Monroe County for 0 Disturbed Pine worth 24 points, giving you 44 points to enter into the ROGO system to build your dream home. Seller has done the Letter of Current Site Conditions with the County as well as engineering for a house, just

    Pamela Stangler Expert Realty LLC

    Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
  • 701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    /55

    $374,000

    • 2 Beds
    • 1.5 Baths
    • 748 Sq Ft

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

    Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
  • 27973 Snapper Ln, Little Torch Key, FL 33042
    27973 Snapper Ln, Little Torch Key, FL 33042
    27973 Snapper Ln, Little Torch Key, FL 33042
    /25

    $474,000

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

    27973 Snapper Ln, Little Torch Key, FL 33042

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

    Bill Vaught (REO Vaught Realty LLC Vaught Realty

    27973 Snapper Ln, Little Torch Key, FL 33042
  • 29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
    /8

    $234,900

    • 2 Beds
    • 1.5 Baths
    • 780 Sq Ft

    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043

    Own a Piece of Paradise - A Renovator's Dream!Embrace the possibilities with this project home opportunity. Whether you're looking to renovate the existing structure or replace it with a modern stilt home, the choice is entirely yours.Property Highlights: Spacious Lot: Enjoy one of the larger lots in the area, offering plenty of room for creative outdoor designs.Home Features: A 2-bedroom,

    Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

    29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
  • 31240 Avenue H, Big Pine Key, FL 33043
    31240 Avenue H, Big Pine Key, FL 33043
    31240 Avenue H, Big Pine Key, FL 33043
    /52

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,076 Sq Ft

    31240 Avenue H, Big Pine Key, FL 33043

    Welcome to your slice of paradise in Big Pine Key! This beautifully updated 3-bedroom, 2-bath home offers move-in-ready comfort with thoughtful upgrades throughout. Step inside to a beautifully renovated kitchen complete with quartz countertops, soft-close cabinetry, and premium finishes. The home offers new luxury vinyl plank (LVP) flooring throughout, blending durability with coastal style. The

    Charity Coffman Brightwild Real Estate

    31240 Avenue H, Big Pine Key, FL 33043
  • 74 Pelican Ln, Big Pine Key, FL 33043
    74 Pelican Ln, Big Pine Key, FL 33043
    74 Pelican Ln, Big Pine Key, FL 33043
    /39

    $730,000

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

    74 Pelican Ln, Big Pine Key, FL 33043

    Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all close.And it also has a completely habitable game room with independent entrance.If the buyer uses the seller's lender and qualifies,

    Yunior Molina My Realty Group, LLC.

    74 Pelican Ln, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    /54

    $899,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

    Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
  • 0 U S Route 1, Big Pine Key, FL 33043
    0 U S Route 1, Big Pine Key, FL 33043
    /2

    $1,125,000

    • Land
    • 0.86 Acre
    • $1,301,248 per Acre

    0 U S Route 1, Big Pine Key, FL 33043

    Seller will finance with one half down payment for ten years, Commercial zoning, Tier 1 lot.

    Barbara Eads Barbara Eads Realty Inc.

    0 U S Route 1, Big Pine Key, FL 33043
  • 0 Adams Rd, Sugarloaf, FL 33042
    0 Adams Rd, Sugarloaf, FL 33042
    0 Adams Rd, Sugarloaf, FL 33042
    /4

    $31,000

    • Land
    • 0.14 Acre
    • $227,941 per Acre

    0 Adams Rd, Sugarloaf, FL 33042

    No RV's, no camping, no clearing, and most likely unbuildable. No utilities to property. Not surveyed. ROGO LETTER IN HAND FOR 1 ROGO POINT. This lot is for dedication to receive 1 Rogo Point, Buyer Verify with County. Being sold as-is. Include extra time in offers to verify marketable title and conduct due diligence. Owner/Agent.

    Carmen David Xcellence Realty

    0 Adams Rd, Sugarloaf, FL 33042
  • 1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
    1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
    1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
    /117

    $11,000,000

    • 6 Beds
    • 8 Baths
    • 4,894 Sq Ft

    1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

    Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress-- built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set on

    Lisa Swanson The Agency Florida Keys

    1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
  • 29176 Violet Dr, Big Pine Key, FL 33043
    29176 Violet Dr, Big Pine Key, FL 33043
    29176 Violet Dr, Big Pine Key, FL 33043
    /24

    $2,340,000

    • 5 Beds
    • 3.5 Baths
    • 2,447 Sq Ft

    29176 Violet Dr, Big Pine Key, FL 33043

    Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen patio. Elegant accents. Lush landscaping, private pool, hot tub. 2 levels, full bar, gourmet kitchen, walk-out patio. Master w/ walk-in closet. Stargaze from wrap-around porch. Must see this private oasis!

    Cliff Glansen FlatFee.com

    29176 Violet Dr, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    /53

    $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
  • 27977 Coral Shores Rd, Little Torch Key, FL 33042
    27977 Coral Shores Rd, Little Torch Key, FL 33042
    27977 Coral Shores Rd, Little Torch Key, FL 33042
    /15

    $399,000

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    27977 Coral Shores Rd, Little Torch Key, FL 33042

    This 2 bedroom 1 bath with a screened in covered porch mobile home on just over 4100 sqft waterfront lot with great boating access.

    Dasha Ray Conch Realty LLC (KW)

    27977 Coral Shores Rd, Little Torch Key, FL 33042
  • 27332 St Martin Ln, Ramrod Key, FL 33042
    27332 St Martin Ln, Ramrod Key, FL 33042
    27332 St Martin Ln, Ramrod Key, FL 33042
    /61

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    27332 St Martin Ln, Ramrod Key, FL 33042

    Welcome to Breezeswept Beach Estates-- In the heart of the Florida Keys! Here, boating, diving, and fishing are a way of life. This waterfront concrete block (CBS) 3-bed, 2-bath home sits on a deep, ocean-side canal just minutes to open water; Looe Key's clear blue reef is about a 15-minute boat ride away, and Key West is roughly 30 minutes by car. Thoughtfully updated for low-maintenance Keys

    Mark Gable Engel & Volkers Marathon

    27332 St Martin Ln, Ramrod Key, FL 33042
  • 17171 Seagrape Ln, Summerland Key, FL 33042
    17171 Seagrape Ln, Summerland Key, FL 33042
    17171 Seagrape Ln, Summerland Key, FL 33042
    /17

    $998,000

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

    17171 Seagrape Ln, Summerland Key, FL 33042

    RARE OPPORTUNITY HERE! This home is perfect for a DIY or Builder. Bring your imagination as it's located in very desirable location of Sugarloaf Shores where homes are over 2++ million dollars. It just needs a makeover but has great bones and many things you won't get now. Full 2 car garage with impact doors and shop. Legal downstairs bath. Large lot on 70' wide flow through canal. Bay views.

    Marie Howe Century 21 Circle - Key West

    17171 Seagrape Ln, Summerland Key, FL 33042
  • 22948 Drake Ln, Summerland Key, FL 33042
    22948 Drake Ln, Summerland Key, FL 33042
    22948 Drake Ln, Summerland Key, FL 33042
    /42

    $650,000

    • Land

    22948 Drake Ln, Summerland Key, FL 33042

    Canal front-vacant lot corners Drake Lane's dead end and is second from Cudjoe Bay's open water: Views and more views. 70-foot concrete seawall with boat slip/basin and 10,000 pound boat lift make this the perfect location for boater/angler's new home. Previous house removed and lot is ready for your new vision. Electric was in place, buyer to verify FKAA sewer/septic tank system. Arborist

    Barbara Bowers Preferred Properties (KW)

    22948 Drake Ln, Summerland Key, FL 33042
  • 27385 Saint Lucie Ln, Summerland Key, FL 33042
    27385 Saint Lucie Ln, Summerland Key, FL 33042
    27385 Saint Lucie Ln, Summerland Key, FL 33042
    /68

    $1,900,000

    • 4 Beds
    • 2.5 Baths
    • 1,994 Sq Ft

    27385 Saint Lucie Ln, Summerland Key, FL 33042

    Tropical Keys Oasis -- Waterfront Luxury Living -- Come experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the

    Amedeo Belmonte William Raveis Real Estate

    27385 Saint Lucie Ln, Summerland Key, FL 33042
  • 29850 Journeys End Rd, Big Pine Key, FL 33043
    29850 Journeys End Rd, Big Pine Key, FL 33043
    29850 Journeys End Rd, Big Pine Key, FL 33043
    /35

    $785,000

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

    29850 Journeys End Rd, Big Pine Key, FL 33043

    Nestled among lush tropical foliage, this inviting 3-bedroom, 2-bath home offers privacy, comfort, and that classic Big Pine Key island vibe. Situated on a dry, double lot, the property provides extra space to relax, garden, or park your boat -- all within a fully fenced yard surrounded by nature and the occasional friendly Key deer 🦌.Step inside to an open, airy living space that flows

    Karen Haack Coldwell Banker Schmitt RE Co.

    29850 Journeys End Rd, Big Pine Key, FL 33043
  • 231 E Shore Dr Unit 2, Summerland Key, FL 33042
    231 E Shore Dr Unit 2, Summerland Key, FL 33042
    231 E Shore Dr Unit 2, Summerland Key, FL 33042
    /7

    $4,150,000 New Construction

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

    231 E Shore Dr Unit 2, 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 2, Summerland Key, FL 33042
  • 643 Indies Rd, Summerland Key, FL 33042
    643 Indies Rd, Summerland Key, FL 33042
    643 Indies Rd, Summerland Key, FL 33042
    /50

    $1,675,000

    • 3 Beds
    • 2 Baths
    • 1,995 Sq Ft

    643 Indies Rd, Summerland Key, FL 33042

    Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

    Greg MacLaren Internet Realty of the Florida Keys

    643 Indies Rd, Summerland Key, FL 33042
  • 1768 Sunrise Dr, Big Pine Key, FL 33043
    1768 Sunrise Dr, Big Pine Key, FL 33043
    1768 Sunrise Dr, Big Pine Key, FL 33043
    /17

    $368,000

    • Land

    1768 Sunrise Dr, Big Pine Key, FL 33043

    Catch a SUNRISE on Sunrise Drive! Vacant canal front lot with long views of Spanish Harbor. A building permit has been applied for and is currently #6 on the list. Direct access to the water, perfect for boaters, fishing enthusiasts, or those seeking a waterfront lifestyle. This 9560 sq foot lot provides some elbow room and is located on a canal PLUS has views of Spanish Harbor. Permit in-process

    Donna Pezzi Keller Williams Key West Compass Realty

    1768 Sunrise Dr, Big Pine Key, FL 33043
  • 3742 Seagrape St, Big Pine Key, FL 33043
    3742 Seagrape St, Big Pine Key, FL 33043
    3742 Seagrape St, Big Pine Key, FL 33043
    /111

    $5,900,000

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

    3742 Seagrape St, Big Pine Key, FL 33043

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

    Ally Kelley Ocean Sotheby's International

    3742 Seagrape St, Big Pine Key, FL 33043
  • 31349 Avenue C, Big Pine Key, FL 33043
    31349 Avenue C, Big Pine Key, FL 33043
    31349 Avenue C, Big Pine Key, FL 33043
    /48

    $749,000

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

    31349 Avenue C, Big Pine Key, FL 33043

    Stunning Brand-New Construction in Big Pine Key!Welcome to your dream home in the Lower Keys! This beautifully elevated Affinity-built 3 bedroom, 2 bathroom home offers the perfect blend of modern comfort, durability, and eco-conscious features. Built in 2025, this home is equipped with all impact-rated windows and doors, offering peace of mind and energy efficiency.Enjoy the spacious

    Sarah Dolson Keller Williams Key West Compass Realty

    31349 Avenue C, Big Pine Key, FL 33043
  • 27345 Guadaloupe Ln, Ramrod Key, FL 33042
    27345 Guadaloupe Ln, Ramrod Key, FL 33042
    27345 Guadaloupe Ln, Ramrod Key, FL 33042
    /15

    $295,000

    • Land

    27345 Guadaloupe Ln, Ramrod Key, FL 33042

    Discover an exceptional canal-front lot that boasts direct bridge-free boating access, making it a fisherman's paradise and an ideal spot for your dream home. Nestled conveniently close to US 1 between Key West and Marathon, this location offers easy access to an array of restaurants, shopping, and mini golf--everything you need for the perfect Keys lifestyle. This Tier III lot is currently in

    Scott Brisson KeyIsle Realty

    27345 Guadaloupe Ln, Ramrod Key, FL 33042
  • 56 W Shore Dr, Summerland Key, FL 33042
    56 W Shore Dr, Summerland Key, FL 33042
    56 W Shore Dr, Summerland Key, FL 33042
    /17

    $785,000

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

    56 W Shore Dr, Summerland Key, FL 33042

    Rare waterfront opportunity in Summerland Key Cove! This 3-bedroom, 2-bath home offers 1,380 sq ft of living area on an oversized 7,000+ sq ft lot with direct access to world-class boating and fishing. Located on a deep, wide ocean-side canal, the property provides a quick ride out to open water -- perfect for enjoying the Lower Keys lifestyle.Summerland Key Cove is a highly desirable,

    Veronica Crego-Flores

    56 W Shore Dr, Summerland Key, FL 33042
  • 24931 Overseas Hwy, Summerland Key, FL 33042
    24931 Overseas Hwy, Summerland Key, FL 33042
    24931 Overseas Hwy, Summerland Key, FL 33042
    /8

    $895,000

    • 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
  • 29523 Enterprise Ave, Big Pine Key, FL 33043
    29523 Enterprise Ave, Big Pine Key, FL 33043
    29523 Enterprise Ave, Big Pine Key, FL 33043
    /46

    $1,080,000

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    29523 Enterprise Ave, Big Pine Key, FL 33043

    Welcome to effortless waterfront living in the heart of Big Pine Key. This updated canal-front retreat 3 bedrooms 2 baths delivers the true Florida Keys lifestyle with comfort, convenience, and outstanding boating access.Sitting on a fully fenced property--ideal for outdoor enjoyment--this home quick, direct access to both the Atlantic Ocean and Gulf of Mexico.Start your mornings with peaceful

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    29523 Enterprise Ave, Big Pine Key, FL 33043
  • 1557 Long Beach Dr, Big Pine Key, FL 33043
    1557 Long Beach Dr, Big Pine Key, FL 33043
    1557 Long Beach Dr, Big Pine Key, FL 33043
    /44

    $4,449,000

    • 7 Beds
    • 7 Baths
    • 4,100 Sq Ft

    1557 Long Beach Dr, Big Pine Key, FL 33043

    1557 Long Beach Dr in Big Pine Key is more than a home, it's an opportunity to own one of the most unique properties in the Lower Keys. Set on a prime lot in the coveted Long Beach Estates, this CBS home has been upgraded with impact windows, a new metal roof, and a completely renovated kitchen. The property delivers what everyone wants but few can find: direct oceanfront with your own sandy

    Guillermo Fernandez Pini Real Estate

    1557 Long Beach Dr, Big Pine Key, FL 33043

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Real Estate & Homes for Sale in Summerland Key, FL

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