Summerland Key, FL Homes for Sale with Garage

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  /36

  $1,185,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  706 Caribbean Dr E, Summerland Key, FL 33042

  OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop,

  Donna Pezzi Keller Williams Key West Compass Realty

  706 Caribbean Dr E, Summerland Key, FL 33042
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  /6

  $1,775,000

  • 4 Beds
  • 4 Baths
  • 1,671 Sq Ft

  193 Galleon Ln, Cudjoe Key, FL 33042

  Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

  Joaquin Merlo-Garzon CRANELUXE

  193 Galleon Ln, Cudjoe Key, FL 33042
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  /31

  $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
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  /41

  $849,000

  $120K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,277 Sq Ft

  29544 Independence Ave, Big Pine Key, FL 33043

  GREAT INVESTMENT OPPORTUNITY! $849,000 Best price property in Pine Channel Estates, Big Pine Key. Fully furnished. Remodeled 2 bdrm/2 full bath + BONUS room (3rd bdrm/office). 75' Canal frontage. Total sq.ft. 1934 w/heated sq.ft. 1277. All new SS appliances. Metal roof, impact windows and garage door, vinyl siding, tankless water heater, gutters, hurricane shutters, fence, covered patio, large

  Jennifer Sylvia Keller Williams Key West Compass Realty

  29544 Independence Ave, Big Pine Key, FL 33043
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  /47

  $1,200,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  637 Caribbean Dr E, Summerland Key, FL 33042

  Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromatic palette, the interiors feel fresh, cohesive, and effortlessly sophisticated--ready for you to start living the Keys lifestyle. Step outside to a relaxing porch overlooking a 60' wide, crystal-clear flow-through canal--perfect

  Donna Pezzi Keller Williams Key West Compass Realty

  637 Caribbean Dr E, Summerland Key, FL 33042
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  /64

  $1,800,000

  $190K PRICE DROP

  • 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
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  /31

  $998,000

  $57K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  83 Sugarloaf Dr, Summerland Key, FL 33042

  Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

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

  83 Sugarloaf Dr, Summerland Key, FL 33042
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  /68

  $1,299,000

  Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  612 Blackbeard Rd, Summerland Key, FL 33042

  Stunning 3 Bedroom 2 Bath waterfront retreat in sought-after Jolly Rogers subdivision featuring a deep flow-through canal with quick boating access, a Trex dock, 15,000 lb boat lift, permitted cargo lift. Built for durability and peace of mind with impact windows and doors, Hardie board siding, aluminum railings, and low-maintenance Trex decking throughout, standing seam metal roof.Inside,

  Diane Corliss Coldwell Banker Schmitt RE Co.

  612 Blackbeard Rd, Summerland Key, FL 33042
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  /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 most

  27385 Saint Lucie Ln, Summerland Key, FL 33042
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  /143

  $19,750,000

  • 6 Beds
  • 6.5 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  15760 Old State Road 4a, Summerland Key, FL 33042
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  /59

  $3,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,409 Sq Ft

  17387 E Dolphin St, Sugarloaf Key, FL 33042

  Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or

  Jesus Parra Coldwell Banker Schmitt RE Co

  17387 E Dolphin St, Sugarloaf Key, FL 33042
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  /63

  $3,295,000

  $400K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  24348 Caribbean Dr W, Summerland Key, FL 33042

  A stunning location with all attributes geared to the view of the beautiful open bay of Summerland Cove. This OCEANFRONT 3 bedroom 3 bath home is on the market for the first time since construction in 1996 and features an extensive renovation nearly complete. The property includes a stunning covered & heated pool with screened enclosure, a 28 foot concrete dock with davits, deep water boating

  Caroline Bauer Key West Sales, LLC

  24348 Caribbean Dr W, Summerland Key, FL 33042
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  /45

  $1,150,000

  $100K PRICE DROP

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

  20868 5th Ave W, Summerland Key, FL 33042

  Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

  Karen Haack Coldwell Banker Schmitt RE Co.

  20868 5th Ave W, Summerland Key, FL 33042
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  /47

  $5,390,000

  $1M PRICE DROP

  • 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
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  /125

  $10,499,000

  New Construction $501K PRICE DROP

  • 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

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
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  /42

  $1,299,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft

  21025 3rd Ave, Summerland Key, FL 33042

  Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21025 3rd Ave, Summerland Key, FL 33042
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  /16

  $895,900

  $94K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Reduced over 100k for a quick sale. Boater's Paradise in Cudjoe Key under 1 million!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

  Rayden Vega Casa Miami Real Estate

  22961 John Avery Ln, Summerland Key, FL 33042
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  /77

  $2,900,000

  • 3 Beds
  • 4 Baths
  • 1,700 Sq Ft

  29581 Richard Rd, Big Pine Key, FL 33043

  Spectacular Open-Water Retreat with Unmatched Sunset ViewThis exceptional open-water property offers breathtaking western-facing sunset views and premier ocean access with no bridges--perfect for boating enthusiasts. Enjoy privacy and natural beauty bordering the Florida Key Deer Preserve.The property features over 200 feet of concrete seawall, a 35' x 15' boat basin making it ideal for

  Diane Corliss Coldwell Banker Schmitt RE Co.

  29581 Richard Rd, Big Pine Key, FL 33043
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  /72

  $1,250,000

  $100K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 2,258 Sq Ft

  4049 Egret Ln, Summerland Key, FL 33042

  Waterfront living meets comfort and functionality in this move-in ready canal front home. Offering 120 feet of concrete dockage in a deep water canal. Quick boating access to Niles Channel. Designed for the ultimate Florida Keys lifestyle, this property combines spacious indoor living with exceptional outdoor entertaining areas. The main home features 2 bedrooms and 2 bathrooms with an

  Deni Heintzelman KeyIsle Realty

  4049 Egret Ln, Summerland Key, FL 33042
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  /36

  $779,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  1719 Narcissus Ave, Big Pine Key, FL 33043

  Located in the peaceful National Key Deer Refuge, this charming 2BD/2BA canal front home in Eden Pines offers the perfect blend of tranquility and classic Florida Keys living. Enjoy frequent visits from the beloved Key Deer while relaxing on one of the screened porches. The property features a fenced yard, outdoor shower, garage, storage area, and rainwater collection system for easy landscape

  Karen Haack Coldwell Banker Schmitt RE Co.

  1719 Narcissus Ave, Big Pine Key, FL 33043
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  /54

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,095 Sq Ft

  667 Caribbean Dr E, Summerland Key, FL 33042

  PILOTS and BOATERS will love this! Tucked away in the heart of Summerland Key, this charming 2-bedroom, 2-bath home captures the essence of true Florida Keys living. Surrounded by swaying palms and coastal breezes, the property features inviting wraparound balconies--perfect for morning coffee or unwinding after a day on the water. Designed with boaters in mind, you'll appreciate the deep,

  Donna Pezzi Keller Williams Key West Compass Realty

  667 Caribbean Dr E, Summerland Key, FL 33042
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  /43

  $999,000

  $300K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft

  19267 Hansen Trail, Summerland Key, FL 33042

  Set on over an acre of land, 19267 Hansen Trail is a truly one-of-a-kind property where modern luxury meets refined homestead living. Offering nearly 2,000 square feet of beautifully remodeled living space, this 3-bedroom, 2-bathroom residence has been thoughtfully upgraded with high-end finishes, all new impact windows and doors, and smart-home conveniences throughout. The open-concept design

  Justyn Ewald Expert Realty LLC (HQ)

  19267 Hansen Trail, Summerland Key, FL 33042
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  /42

  $849,999

  $75K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  324 Airport Dr S, Summerland Key, FL 33042

  Rare opportunity to own a canal-front home directly on the private Summerland Cove Airport--where you can fly in, dock up, and be on open water in minutes. This solid CBS home offers 960 sq ft of elevated living space, currently configured as a spacious 1-bedroom, 1-bath upstairs (originally a 2-bedroom--easily converted back). Downstairs features a fully enclosed, permitted bonus area with an

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  324 Airport Dr S, Summerland Key, FL 33042
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  /19

  $685,000

  • 3 Beds
  • 2 Baths
  • 986 Sq Ft

  29175 Violet Dr, Big Pine Key, FL 33043

  Eden Pines Gem: Fully updated, low assumable flood Modern Island Living: Updated Stilted Retreat in Golf-Cart Friendly Eden Pines!Welcome to 29175 Violet Drive, a fully updated 3-bedroom, 2-bathroom stilted sanctuary in the heart of Big Pine Key. This home is tucked into the vibrant, family-oriented community of Eden Pines Colony-a neighborhood where neighbors are friends and the island lifestyle

  Ralph Harvey LISTWITHFREEDOM.COM

  29175 Violet Dr, Big Pine Key, FL 33043
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  /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
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  /85

  $1,695,000

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

  30363 Flamingo Ln, Big Pine Key, FL 33043

  Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete waterfront home offers quick access to both the Atlantic and Gulf, putting you in the heart of world-class fishing and diving. Located just a few miles from Bahia Honda State Park, you're ideally positioned for elite tarpon fishing, backcountry action, reef trips, and offshore runs. The dock is built for

  Coby Taylor Expert Realty LLC (HQ)

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

  $890,000

  $20K PRICE DROP

  • 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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