8,608

Summerland Key, FL Homes

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  • /10

    $499,000

    • Land

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 917-4422

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • /14

    $205,000

    Sold May 20, 2026

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

    • Land
    • 1,742 Sq Ft
    • $5,125,000 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 56 Days On Market

    Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
    • /2

      Est $3,310,289

      Not Listed For Sale

      999 Flagship Dr, Summerland Key, FL 33042

      • 3 Beds
      • 4 Baths
      • 3,531 Sq Ft
      • Built 2024
      999 Flagship Dr, Summerland Key, FL 33042

      Last Sold Summary

  • /28

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,184 Sq Ft

    290 46th St, Summerland Key, FL 33042

    Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport! This property is a fixer-upper, or teardown, located on Summerland Key, at the base of the airport runway. 2/1 on one side, and an additional 12 x32 en suite with a separate entrance on the other side. The home sits on a rare double lot totaling 11,000 SF. If you like privacy, this is it,

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (645) 219-1684

    290 46th St, Summerland Key, FL 33042
  • /43

    $1,700,000

    Sold Jan 30, 2026

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $820/SF
    • 140 Days On Market

    Current Estimated Value $1,689,319

    Last Listing Agent Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
    • /34

      Not Listed For Sale

      701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1998
      701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

      Last Sold Summary

      • 66 Days On Market

  • /36

    $665,000

    $53K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,497 Sq Ft

    30416 Coconut Hwy, Big Pine Key, FL 33043

    Looking for a lot of land in the Keys, and a well-maintained home? This rare 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV, boat trailers, so much more! Over 1⁄2 acre, the 4 lots are bordered by Coconut Hwy. to the north, Avenue B to the west, and Hibiscus Ln. to the south from which vehicles can access the large, fenced portion of the back yard. Step inside

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (888) 817-7679

    30416 Coconut Hwy, Big Pine Key, FL 33043
  • /26

    $239,000

    Sold Jun 30, 2025

    701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 2% Below List Price
    • 74 Days On Market

    Current Estimated Value $244,972

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
    • /2

      Est $1,314,972

      Not Listed For Sale

      29565 Ranger Ave, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2019
      29565 Ranger Ave, Big Pine Key, FL 33043

      Last Sold Summary

  • /41

    $550,000

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft

    30372 Palm Dr, Big Pine Key, FL 33043

    Well-priced Keys living starts here! This 12,500 sq. ft. double lot offers ample parking and room to add a pool, garage, tiki hut, or more. In 2022, the current owner added a metal roof, impact-resistant windows and doors, and Mitsubishi mini-split A/C units. Inside, the home features a spacious great room, three bedrooms, one updated bath, and tile floors throughout. Outside, you'll find a solar

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (888) 376-2422

    30372 Palm Dr, Big Pine Key, FL 33043
  • /44

    $700,000

    Sold Jan 09, 2026

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $810/SF
    • 23 Days On Market

    Last Listing Agent Holly Burger Berkshire Hathaway HomeServices Knight & Gardner Realty

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
    • /14

      Not Listed For Sale

      0 Lan Horvath Rd, Big Pine, FL 33043

      0 Lan Horvath Rd, Big Pine, FL 33043

      Last Sold Summary

      • 64 Days On Market

  • /47

    $599,000

    New Construction $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 225-2318

    701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
  • /43

    $990,000

    Sold Dec 10, 2025

    29839 Newfound Blvd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Below List Price
    • $566/SF
    • 4 Days On Market

    Current Estimated Value $1,000,115

    Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

    29839 Newfound Blvd, Big Pine Key, FL 33043
    • /2

      Est $1,023,501

      Not Listed For Sale

      18954 Acosta Trail, Summerland Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 1,008 Sq Ft
      • Built 2013
      18954 Acosta Trail, Summerland Key, FL 33042

      Last Sold Summary

  • /67

    $3,200,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft

    270 E Caribbean Dr, Summerland Key, FL 33042

    Set against a spectacular open water backdrop with unforgettable sunset views modern, waterfront home was designed for both luxury living and serious boating. Built in 2022 with an exceptional design, the residence features solid concrete construction, polished concrete floors, impact-rated windows and doors, and a strong elevated build that delivers peace of mind in the Florida Keys

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-1469

    270 E Caribbean Dr, Summerland Key, FL 33042
  • /88

    $3,475,000

    Sold May 19, 2026

    680 Elma Ave, Big Pine Key, FL 33043

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft
    • Built 1971

    Last Sold Summary

    • 11% Below List Price
    • $1,695/SF
    • 140 Days On Market

    Current Estimated Value $3,638,904

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    680 Elma Ave, Big Pine Key, FL 33043
    • /2

      Est $504,491

      Not Listed For Sale

      520 Blackbeard Rd, Little Torch Key, FL 33042

      • Studio
      520 Blackbeard Rd, Little Torch Key, FL 33042

      Last Sold Summary

  • /59

    $599,000

    New Construction $45K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 220-2833

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
  • /48

    $291,000

    Sold Mar 03, 2026

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $404/SF
    • 133 Days On Market

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    • /4

      Not Listed For Sale

      0 Knockemdown Unit A11382026, Lower Keys, FL 33042

      0 Knockemdown Unit A11382026, Lower Keys, FL 33042

      Last Sold Summary

      • 198 Days On Market

  • /29

    $775,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,162 Sq Ft

    28452 Yucatan Ln, Summerland Key, FL 33042

    Must be sold after Jan 1, 2027. Canal front home with quick exit out of the canal to Pine Channel for Atlantic or Gulf access. 7200 sq.ft. lot. Back yard big enough for a pool. Pack your toothbrush and your ready for your salt life to begin. Being sold mostly furnished 2bd/2bth 1162 sq.ft. Home, plus, southerly facing screen porch, which has accordian shutters,porch faces back yard and canal.

    Rose Dell Keller Williams Key West Compass Realty

    28452 Yucatan Ln, Summerland Key, FL 33042
  • /47

    $1,282,000

    Sold Nov 12, 2025

    29436 Independence Ave, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $855/SF
    • 82 Days On Market

    Current Estimated Value $1,268,264

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    29436 Independence Ave, Big Pine Key, FL 33043
    • /2

      Est $936,715

      Not Listed For Sale

      27434 Saint Lucie Ln, Ramrod Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 2022
      27434 Saint Lucie Ln, Ramrod Key, FL 33042

      Last Sold Summary

  • /39

    $499,000

    • 2 Beds
    • 2 Baths
    • 618 Sq Ft

    701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

    Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

    Suzanne Moore Suzanne Moore Real Estate

    701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042
  • /43

    $1,410,000

    Sold Apr 30, 2026

    17152 Marlin Dr, Sugarloaf Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1989

    Last Sold Summary

    • 12% Below List Price
    • $1,175/SF
    • 70 Days On Market

    Current Estimated Value $1,525,640

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17152 Marlin Dr, Sugarloaf Key, FL 33042
    • /2

      Est $2,406,901

      Not Listed For Sale

      305 S Point Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 2,360 Sq Ft
      • Built 1986
      305 S Point Dr, Summerland Key, FL 33042

      Last Sold Summary

  • /21

    $465,000

    • 1 Bed
    • 1 Bath
    • 799 Sq Ft

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

    A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

    Rose Dell Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
  • /2

    $255,000

    Sold Oct 20, 2025

    150 Coral Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Built 1993

    Last Sold Summary

    • $232/SF
    • 0 Days On Market

    Current Estimated Value $632,297

    Last Listing Agent User Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

    150 Coral Ave, Summerland Key, FL 33042
    • /2

      Est $1,513,264

      Not Listed For Sale

      22863 Bluegill Ln, Cudjoe Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,986 Sq Ft
      • Built 2019
      22863 Bluegill Ln, Cudjoe Key, FL 33042

      Last Sold Summary

  • /31

    $749,500

    Open Fri 1PM - 3PM $46K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,562 Sq Ft

    360 W Shore Dr, Summerland Key, FL 33042

    Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

    Brenda Thomas Weichert Realtors Hallmark Properties

    360 W Shore Dr, Summerland Key, FL 33042
  • /3

    $325,000

    Sold Oct 09, 2025

    29153 Tulip Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1984

    Last Sold Summary

    • $356/SF
    • 0 Days On Market

    Current Estimated Value $364,412

    Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

    29153 Tulip Ln, Big Pine Key, FL 33043
    • /3

      Est $892,000

      Not Listed For Sale

      0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

      0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

      Last Sold Summary

      • 4 Days On Market

  • /26

    $550,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    31171 Avenue H, Big Pine Key, FL 33043

    Big Pine Key Here's your opportunity to get into a 3 Bedroom. 2 Bath stilt home in the Keys. Metal Roof. Brand New Central A/C & Heat. Sliding door from house to Covered Porch. Garage and Storage, downstairs, Concrete Patio. Back yard has concrete slab for a storage shed. Sewer has been connected and paid for in full. Fenced. Easement behind fence line between this home and back neighbor. For

    Rose Dell Keller Williams Key West Compass Realty

    31171 Avenue H, Big Pine Key, FL 33043
  • /51

    $420,000

    Sold Nov 21, 2025

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1979

    Last Sold Summary

    • 8% Below List Price
    • $515/SF
    • 185 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
    • /23

      Not Listed For Sale

      17295 Keystone Rd, Sugarloaf Shores, FL 33042

      17295 Keystone Rd, Sugarloaf Shores, FL 33042

      Last Sold Summary

      • 8 Days On Market

  • /32

    $975,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,503 Sq Ft

    30451 Hibiscus Ln, Big Pine Key, FL 33043

    ONE-OF-A-KIND! Custom-built home '2010'on a large 125 X 250 property, 31,250 sq. ft. more than 1/2 acre. 4bd/3bth plus a bonus room for a total 2493 sqft. Perfect for 2 working professionals from home or a big family. Good size bedrooms. 2 are ensuite. Separate Kitchen Dining & Living Room and an extra room for office or hobbies, gym or guest. Concrete slab under house same size of house so lots

    Rose Dell Keller Williams Key West Compass Realty

    30451 Hibiscus Ln, Big Pine Key, FL 33043
  • /84

    $1,600,000

    Sold Apr 09, 2026

    17125 Wahoo Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • Built 1982

    Last Sold Summary

    • $971/SF
    • 8 Days On Market

    Current Estimated Value $1,573,859

    Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    17125 Wahoo Ln, Summerland Key, FL 33042
    • /2

      Est $340,000

      Not Listed For Sale

      0 E Ave Unit 604969, Big Pine Key, FL 33043

      • Studio
      0 E Ave Unit 604969, Big Pine Key, FL 33043

      Last Sold Summary

  • /36

    $750,000

    • Land
    • 9.25 Acres
    • $81,081 per Acre

    0 Niles Rd Unit MLS A11925960, Summerland Key, FL 33042

    Discover the perfect opportunity to build your dream home in the Lower Keys on this desirable parcel located on Summerland Key, FL. Set within a peaceful residential neighborhood, this property offers an inviting blend of tranquility and convenience—just minutes from US-1, local marinas, boat ramps, dining, beaches, and world-class fishing. Enjoy the relaxed island lifestyle, tropical breezes,

    Javier Santana Sunland Real Estate, LLC.

    0 Niles Rd Unit MLS A11925960, Summerland Key, FL 33042

Showing Results 201 - 240, Page 6 of 18

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