8,628

Summerland Key, FL Homes

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    • /2

      Not Listed For Sale

      3 Big Pine Ave, Big Pine Key, FL 33043

      3 Big Pine Ave, Big Pine Key, FL 33043

      Last Sold Summary

      Last Sold Price $39,666

      Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

  • /22

    $679,000

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

    19591 Navajo St, Summerland Key, FL 33042

    INDIAN MOUNDS SPECIAL!!!! Two balconies with ocean views and a hot tub to enjoy them with!!! Just one block from the private community boat ramp, this elevated 2 bed, 2 bath home sits on a large oversized corner lot. There is plenty of room for parking your toys and a downstairs enclosure for additional storage. Hardibacker siding and a metal roof provide peace of mind.Upon entering, you'll find

    Agent Photo

    Mike Kane

    Internet Realty of the Florida Keys

    (645) 230-1301

    19591 Navajo St, Summerland Key, FL 33042
  • /33

    $1,075,000 Sold Feb 20, 2026

    17226 Jamaica Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1998

    Last Sold Summary

    • 10% Below List Price
    • $861/SF
    • 32 Days On Market

    Current Estimated Value $1,173,673

    Last Listing Agent Stephen Hachey

    17226 Jamaica Ln, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      2 Big Pine Ave, Big Pine Key, FL 33043

      2 Big Pine Ave, Big Pine Key, FL 33043

      Last Sold Summary

      Last Sold Price $39,666

      Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

  • /36

    $750,000

    • Land
    • 9.26 Acres
    • $80,995 per Acre

    0 Niles Rd, 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,

    Agent Photo

    Javier Santana

    Sunland Real Estate, LLC.

    (786) 504-0768

    0 Niles Rd, Summerland Key, FL 33042
  • /42

    $635,000 Sold Feb 19, 2026

    3231 Pompano St, Big Pine Key, FL 33043

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

    Last Sold Summary

    • 2% Below List Price
    • $735/SF
    • 6 Days On Market

    Current Estimated Value $641,572

    Last Listing Agent Dawn McComish Lokation Real Estate

    3231 Pompano St, Big Pine Key, FL 33043
    • /2

      Not Listed For Sale

      1 Big Pine Ave, Big Pine Key, FL 33043

      1 Big Pine Ave, Big Pine Key, FL 33043

      Last Sold Summary

      Last Sold Price $39,666

      Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

  • /53

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    29534 Geraldine St, Big Pine Key, FL 33043

    Discover the perfect blend of island lifestyle and income potential in this well-appointed waterfront home located in a desirable Big Pine Key boating community with Commercial Fishing District zoning--a rare advantage allowing marine-based business use, boat storage, and added flexibility.Situated on a 18,000 sq ft double lot with 150' of canal frontage, this solid concrete, single-level home

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (844) 697-1109

    29534 Geraldine St, Big Pine Key, FL 33043
  • /17

    $395,000 Sold Sep 22, 2025

    10W Cooks Unit B, Cook Island Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 596 Sq Ft
    • Built 1948

    Last Sold Summary

    • 12% Below List Price
    • $663/SF
    • 13 Days On Market

    Current Estimated Value $425,000

    Last Listing Agent Greg Gordon Island Home Realty Inc.

    10W Cooks Unit B, Cook Island Key, FL 33043
    • /9

      Not Listed For Sale

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      Last Sold Summary

      • 543 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

  • /51

    $1,999,999 Under Contract

    • 3 Beds
    • 4 Baths
    • 2,100 Sq Ft

    23087 Sailfish Ln, Summerland Key, FL 33042

    Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 807-9315

    23087 Sailfish Ln, Summerland Key, FL 33042
  • /54

    $915,000 Sold Aug 19, 2025

    29737 Newfound Blvd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $866/SF
    • 33 Days On Market

    Current Estimated Value $944,566

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

    29737 Newfound Blvd, Big Pine Key, FL 33043
    • /2

      Not Listed For Sale

      30919 Edward Rd Unit A & B, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,170 Sq Ft
      • Built 1943
      30919 Edward Rd Unit A & B, Big Pine Key, FL 33043

      Last Sold Summary

      • $316/SF

      Last Sold Price $370,000

      Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  • /67

    $1,449,900

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    17215 Bonita Ln E, Summerland Key, FL 33042

    Completely reimagined and absolutely stunning, this beautifully remodeled home in Sugarloaf Shores showcases a full renovation, including a brand new dock. The beautiful 3 Bedroom 2 Bathroom home features commercial grade luxury vinyl floors, beautiful new finishes, custom cabinetry, new appliances, and fresh paint inside and out. Every detail was thoughtfully selected, creating a clean, modern

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 798-4569

    17215 Bonita Ln E, Summerland Key, FL 33042
  • /27

    $1,900,000 Sold Jun 18, 2025

    17022 Starfish Ln W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,990 Sq Ft
    • Built 1994

    Last Sold Summary

    • 14% Below List Price
    • $955/SF
    • 85 Days On Market

    Current Estimated Value $1,977,344

    Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

    17022 Starfish Ln W, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      430 Les Rohde Dr, Ramrod Key, FL 33042

      430 Les Rohde Dr, Ramrod Key, FL 33042

      Last Sold Summary

      Last Sold Price $180,000

      Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  • /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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (844) 795-0878

    30463 Hawk Ln, Big Pine Key, FL 33043
  • /60

    $2,512,500 Sold Oct 31, 2025

    1260 Sugarloaf Blvd, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,886 Sq Ft
    • Built 1991

    Last Sold Summary

    • 3% Below List Price
    • $871/SF
    • 60 Days On Market

    Current Estimated Value $2,458,790

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1260 Sugarloaf Blvd, Summerland Key, FL 33042
    • /2

      Est $426,128 Not Listed For Sale

      20874 4th Ave, Cudjoe Key, FL 33042

      • Studio
      20874 4th Ave, Cudjoe Key, FL 33042

      Last Sold Summary

      • 5% Below List Price

      Last Sold Price $450,000

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

  • /16

    $1,200,000

    • 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,

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (844) 920-0831

    715 Caribbean Dr E, Summerland Key, FL 33042
  • /58

    $2,025,000 Sold May 13, 2025

    22440 Jolly Roger Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 1988

    Last Sold Summary

    • 12% Below List Price
    • $1,567/SF
    • 85 Days On Market

    Current Estimated Value $2,062,598

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    22440 Jolly Roger Dr, Summerland Key, FL 33042
    • /2

      Est $1,158,249 Not Listed For Sale

      21034 Overseas Hwy, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,361 Sq Ft
      • Built 2022
      21034 Overseas Hwy, Cudjoe Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $808/SF

      Last Sold Price $1,100,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /91

    $1,200,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    21855 Spain Blvd, Summerland Key, FL 33042

    Imagine owning a pool home and 3.3 private acres in the Florida Keys - this rare opportunity is in Cudjoe Acres, an equestrian area just 20 miles from Key West, with two equestrian facilities just around the corner. The home sits on one secluded acre surrounded by a botanical garden of impressive plantings including rare palm trees, buttonwoods, orchids, dragon fruit cactus, fragrant Joe wood, a

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 225-2307

    21855 Spain Blvd, Summerland Key, FL 33042
  • /29

    $495,000 Sold Feb 13, 2026

    31525 Avenue A, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft
    • Built 1958

    Last Sold Summary

    • 10% Below List Price
    • $387/SF
    • 229 Days On Market

    Current Estimated Value $528,667

    Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

    31525 Avenue A, Big Pine Key, FL 33043
    • /2

      Not Listed For Sale

      1138 Basque Ln, Summerland Key, FL 33042

      • 7,000 Sq Ft
      1138 Basque Ln, Summerland Key, FL 33042

      Last Sold Summary

      • $10/SF

      Last Sold Price $70,000

      Last Listing Agent Jimmy Lane Island Life Realty Experts

  • /84

    $1,290,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,596 Sq Ft

    29653 Saratoga Ave, Big Pine Key, FL 33043

    Looking for your piece of paradise in the Keys? You've found it! This property feels like a lush private resort. The exceptional features include pavers on deck and dock, heated/chilled pool, tiki hut and tiki bar, chef's outdoor kitchen, 10k boat lift, landscape irrigation with separate water meter, and landscape lighting. The entire yard is fenced and gated. The 1596 sq. ft. concrete block home

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (844) 638-3161

    29653 Saratoga Ave, Big Pine Key, FL 33043
  • /32

    $635,000 Sold Apr 25, 2025

    2682 Koehns Ave, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1963

    Last Sold Summary

    • 2% Below List Price
    • $509/SF
    • 12 Days On Market

    Current Estimated Value $650,937

    Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

    2682 Koehns Ave, Big Pine Key, FL 33043
    • /61

      Est $2,784,138 Not Listed For Sale

      20886 4th Ave W, Summerland Key, FL 33042

      • 4 Beds
      • 3 Baths
      • 3,042 Sq Ft
      • Built 2008
      20886 4th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Below List Price
      • $953/SF
      • 66 Days On Market

      Last Sold Price $2,900,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /19

    $215,000

    • Land

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

    Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 761-5180

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • /51

    $975,000 Sold Aug 01, 2025

    527 Heck Ave, Little Torch Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2023

    Last Sold Summary

    • 17% Below List Price
    • $812/SF
    • 101 Days On Market

    Current Estimated Value $1,074,725

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    527 Heck Ave, Little Torch Key, FL 33042
    • /2

      Est $821,000 Not Listed For Sale

      164 Newfound Blvd, Big Pine Key, FL 33043

      • Studio
      164 Newfound Blvd, Big Pine Key, FL 33043

      Last Sold Summary

      • 721% Below List Price

      Last Sold Price $100,000

      Last Listing Agent Jimmy Lane Island Life Realty Experts

  • /39

    $1,499,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    20838 5th Ave W, Summerland Key, FL 33042

    Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 952-7261

    20838 5th Ave W, Summerland Key, FL 33042
  • /41

    $689,000 Sold Jun 27, 2025

    29873 Journeys End Rd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,184 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $582/SF
    • 104 Days On Market

    Current Estimated Value $752,294

    Last Listing Agent Heather Bennett Keller Williams Key West Compass Realty

    29873 Journeys End Rd, Big Pine Key, FL 33043
    • /2

      Est $479,667 Not Listed For Sale

      2112 San Marco Dr, Big Pine Key, FL 33043

      • Studio
      2112 San Marco Dr, Big Pine Key, FL 33043

      Last Sold Summary

      • 734% Below List Price

      Last Sold Price $57,500

      Last Listing Agent Gladys Cornell RE/MAX

  • /37

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    29160 Primrose Ln, Big Pine Key, FL 33043

    Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key.Featuring a garage and tons of storage inside and out, fenced yard & room for a pool!Inside you will find 3BR, 2 updated baths and a smart layout with an open concept living.Step outside to a beautiful covered porch the perfect spot to enjoy your morning coffee watching the key

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    (877) 521-8118

    29160 Primrose Ln, Big Pine Key, FL 33043
  • /44

    $1,550,000 Sold Feb 27, 2026

    17094 Coral Dr, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,998 Sq Ft
    • Built 1982

    Last Sold Summary

    • 14% Below List Price
    • $776/SF
    • 265 Days On Market

    Current Estimated Value $1,691,320

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17094 Coral Dr, Summerland Key, FL 33042
    • /2

      Est $485,000 Not Listed For Sale

      2120 San Marco Dr, Big Pine Key, FL 33043

      • Studio
      2120 San Marco Dr, Big Pine Key, FL 33043

      Last Sold Summary

      • 743% Below List Price

      Last Sold Price $57,500

      Last Listing Agent Gladys Cornell RE/MAX

  • /60

    $487,500

    • 2 Beds
    • 1 Bath
    • 667 Sq Ft

    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 981-9841

    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
  • /3

    $49,000 Sold Jun 06, 2025

    Lot 24 Vacant Land, Big Torch Key, FL 33042

    • Land

    Last Sold Summary

    • 35% Below List Price
    • 206 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 24 Vacant Land, Big Torch Key, FL 33042
    • /2

      Est $944,955 Not Listed For Sale

      31441 Ave F, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 854 Sq Ft
      • Built 1980
      31441 Ave F, Big Pine Key, FL 33043

      Last Sold Summary

      • 195% Below List Price
      • $375/SF

      Last Sold Price $320,000

      Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

Showing Results 241 - 280, Page 7 of 18

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