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Summerland Key, FL Homes for Sale with Garage

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  • /68

    $2,985,000

    • 3 Beds
    • 2 Baths
    • 2,232 Sq Ft

    23941 Henry St, Summerland Key, FL 33042

    Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

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    Stacy Shahan

    Island Real Estate Company Florida Keys

    (786) 686-4688

    23941 Henry St, Summerland Key, FL 33042
  • /47

    $1,099,000

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

    29051 Magnolia Ln, Big Pine Key, FL 33043

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

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    Yvette Toledo-Baste

    Compass Florida, LLC

    (866) 971-5749

    29051 Magnolia Ln, Big Pine Key, FL 33043
  • /75

    $4,500,000

    • 3 Beds
    • 4 Baths
    • 4,200 Sq Ft

    421 La Fitte Rd, Little Torch Key, FL 33042

    An extraordinary waterfront offering in Little Torch Key, representing the highest level of design, construction, and lifestyle in the Lower Florida Keys. Designed and built by premier builder D'Asign Source, this poured-concrete residence is set on a rare double waterfront lot with expansive Pine Channel views and direct access to world-class boating, fishing, and diving. Approximately 4,200 sq

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    Sandra Tuttle

    Island Welcome Real Estate

    (645) 300-4633

    421 La Fitte Rd, Little Torch Key, FL 33042
  • /64

    $1,790,000

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    30463 Hawk Ln, Big Pine Key, FL 33043

    Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living.Outdoors, the home transforms into a

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    Sandra Tuttle

    Island Welcome Real Estate

    (844) 795-0878

    30463 Hawk Ln, Big Pine Key, FL 33043
  • /90

    $3,695,000

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    680 Elma Ave, Big Pine Key, FL 33043

    RARE west-facing private estate offering sunset views, owned bay bottom, and exceptional boating access. Welcome to Tarpon Cove, an exclusive retreat located in Big Pine Key, surrounded by the Florida Key Deer Preserve for unmatched privacy and natural beauty.The concrete residence has been meticulously reconstructed through a down-to-the-studs renovation, resulting in a 2023 effective age and is

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    Sandra Tuttle

    Island Welcome Real Estate

    (877) 359-5426

    680 Elma Ave, Big Pine Key, FL 33043
  • /34

    $1,399,000

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    1657 Watson Blvd, Big Pine Key, FL 33043

    Experience the keys waterfront lifestyle! This charming 3 bedroom, 2 bath home has peekaboo views of Big Pine Bight and is minutes away from Bogie Channel with NO limiting bridges to slow you down. Only 2 minutes to the Atlantic, and direct access to the Gulf. Equipped with a 10,000 LB boat lift, the boat is also available as a separate purchase. The buyer will get first right of refusal on the

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (833) 532-1578

    1657 Watson Blvd, Big Pine Key, FL 33043
  • /60

    $1,490,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    27433 Antigua Rd, Summerland Key, FL 33042

    NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and impact-rated windows & doors,

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • /41

    $749,000

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

    251 Pelican Ln, Big Pine Key, FL 33043

    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 dining areas--ideal for

    Sunnie San Lorenzo KeyIsle Realty

    251 Pelican Ln, Big Pine Key, FL 33043
  • /59

    $979,999

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

    30368 Killdeer Ln, Big Pine Key, FL 33043

    Welcome to island living in Big Pine Key. Situated on a desirable corner lot, this beautifully remodeled 3-bedroom, 2-bathroom home offers 70 feet of dockage with davits, providing excellent boating access and true waterfront Keys living. The home has been fully updated, featuring a newer roof, updated windows, modern flooring, renovated kitchen and bathrooms, and upgraded lighting throughout.

    Alexander Pinero Pine River Realty, LLC

    30368 Killdeer Ln, Big Pine Key, FL 33043
  • /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
  • /39

    $975,000

    • 2 Beds
    • 3 Baths
    • 1,120 Sq Ft

    421 Ixora Dr, Big Pine Key, FL 33043

    Beautifully maintained elevated Florida Keys home offering 2 bedrooms and 2 bathrooms upstairs plus a legal bathroom downstairs. This thoughtfully designed residence sits on a spacious 10,568 sq. ft. lot with ample parking for an RV and/or boat trailer and features quality construction throughout. Home was completely remodeled post Irma down to the studs. The interior showcases porcelain

    Melissa Graham Bluescape Real Estate

    421 Ixora Dr, Big Pine Key, FL 33043
  • /35

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    29662 Independence Ave, Big Pine Key, FL 33043

    Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

    Halley Haack Coldwell Banker Schmitt RE Co.

    29662 Independence Ave, Big Pine Key, FL 33043
  • /23

    $730,000

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

    74 Pelican Ln, Big Pine Key, FL 33043

    Completely remodeled property with a new roof installed in 2024, new flooring, termite treatment completed in 2025, fully furnished, and ideally located just 30 minutes from Key West. It's close to restaurants, schools, beaches, recreational facilities, and everything you need for a peaceful and enjoyable life. It also features an additional, fully finished game room with a separate entrance. The

    Yunior Molina My Realty Group, LLC.

    74 Pelican Ln, Big Pine Key, FL 33043
  • /49

    $980,000

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

    29559 Ranger Ave, Big Pine Key, FL 33043

    This well desired location and immaculately maintained home is 5 minutes from world class boating, fishing, diving and snorkeling. Located in Pine Channel Estates for the fastest and easiest direct access to the ocean or the endless options of bay-side boating adventures. Boasting a 75' concrete seawall with a 14K boat lift, davits, and drop-down on/off boat access, there is even a dive board for

    Donna Halstead Coldwell Banker Schmitt RE Co.

    29559 Ranger Ave, Big Pine Key, FL 33043
  • /29

    $925,000

    • 2 Beds
    • 2 Baths
    • 1,291 Sq Ft

    31364 Avenue J, Big Pine Key, FL 33043

    Open Waterfront Double Lot with Protected Boating and Endless PossibilitiesDiscover the best of Florida Keys waterfront living on this spacious double lot located on a quiet street on the open water with 150 feet of protective canal frontage with seawall, this property offers direct boating access to both the backcountry and the Atlantic Ocean and is only one lot in from the mouth of the canal

    Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

    31364 Avenue J, Big Pine Key, FL 33043
  • /64

    $1,900,000

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft

    3127 Stewart Rd, Summerland Key, FL 33042

    Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

    Pamela Stangler Expert Realty LLC

    3127 Stewart Rd, Summerland Key, FL 33042
  • /47

    $1,200,000

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

    43 Venetian Way, Summerland Key, FL 33042

    Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

    Lori Cameron Buy The Keys

    43 Venetian Way, Summerland Key, FL 33042
  • /47

    $5,900,000

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

    3742 Seagrape St, Big Pine Key, FL 33043

    Escape to “The Castle”, a luxurious gated Gulf-front estate spanning 1.14 acres on Big Pine Key. Built in 2014 with poured concrete, impact windows/doors, elevator, and generator, this 4,600+ sq. ft. masterpiece offers 3 bedrooms, 3 baths, and breathtaking Gulf views. Boaters enjoy 235’ of dockage: 140’ protected canal dock with lift, ramp, and slip, plus 95’ open-water pier dock with lift and

    Jo Ann Cook Ocean Sotheby's International

    3742 Seagrape St, Big Pine Key, FL 33043
  • /17

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft

    715 Caribbean Dr E, Summerland Key, FL 33042

    Experience the ultimate Florida Keys lifestyle at 715 Caribbean Drive East in Summerland Key. Located in a desirable boating and aviation community, this property offers rare access to a private neighborhood airstrip, ideal for pilots and aviation enthusiasts. Designed for boaters, the home features a 60-foot dock and a 15,000-lb boat lift, providing easy access to open water, nearby sandbars,

    Yohane Carcases Coldwell Banker Schmitt Real E

    715 Caribbean Dr E, Summerland Key, FL 33042
  • /36

    $750,000

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

    31107 Avenue I, Big Pine Key, FL 33043

    Discover the ultimate Florida Keys lifestyle in this meticulously maintained 3-bedroom, 2-bathroom home with 2-car garage and a fresh, bright interior with new paint, this residence is move-in ready and full of potential. Located just moments from the water, you'll enjoy a sense of space and privacy that is hard to find. Whether you’re looking for a peaceful primary residence or a high-potential

    Maria Downing LoKation

    31107 Avenue I, Big Pine Key, FL 33043
  • /22

    $610,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    29119 Violet Dr, Big Pine Key, FL 33043

    Discover the charm and potential of this tropical nature lover's retreat in the heart of Big Pine Key. This two-bedroom, two-bath home is nestled within a lush, natural setting where Key deer, native birds, and island wildlife are part of everyday life--offering a rare connection to the authentic Florida Keys.Set on a nicely sized fenced yard, the property provides space to garden, relax, or

    Dawn McComish Lokation Real Estate

    29119 Violet Dr, Big Pine Key, FL 33043
  • /41

    $840,000

    • 2 Beds
    • 2 Baths
    • 1,048 Sq Ft

    3635 Trade Winds St, Big Pine Key, FL 33043

    Beautifully Renovated Single-Family Home in the Florida Keys This stunning 2-bedroom, 2-bathroom home with extra guess room downstairs, fully renovated in 2024, is perfect for fishing enthusiasts and those seeking a serene island lifestyle. The property boasts a dock with no bridges to the ocean, ideal for quick access to the water. Located in a quiet neighborhood, this home features a 2018 roof,

    Michel Luna Lifestyle International Realty

    3635 Trade Winds St, Big Pine Key, FL 33043
  • /60

    $175,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    27433 Antigua Rd, Summerland Key, FL 33042

    NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • /16

    $989,999

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

    Rayden Vega Casa Miami Real Estate

    22961 John Avery Ln, Summerland Key, FL 33042
  • /44

    $1,199,000

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

    27426 Martinique Ln, Summerland Key, FL 33042

    Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

    Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27426 Martinique Ln, Summerland Key, FL 33042
  • /43

    $1,750,000

    • 3 Beds
    • 3 Baths
    • 1,837 Sq Ft

    30363 Flamingo Ln, Big Pine Key, FL 33043

    Tranquility meets coastal living, discover this stunning concrete constructed home built in 1993. Located in the desirable subdivision of Tropical Bay Estates this elevated waterfront residence offers unparalleled access to both the ocean and bay, just 15 minutes by boat. The iconic No Name Pub is just a 2-minute drive or a 15-minute walk away for some of the best pizza in the Keys. A few

    Jo Ann Cook Ocean Sotheby's International Realty

    30363 Flamingo Ln, Big Pine Key, FL 33043
  • /51

    $910,000

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

    813 Hawksbill Ln, Summerland Key, FL 33042

    Charming 2BR/2BA Keys home on Upper Sugarloaf. FULL HOUSE GENERATOR WITH TRANSFER SWITCH,Built on sturdy concrete pilings with Hardie board siding and a metal roof, Large workshop, storage space on first level with Laundry room, this three-story retreat of island living. Inside, you’ll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys

    Guadalupe Perez Douglas Elliman

    813 Hawksbill Ln, Summerland Key, FL 33042
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