11,009

Summerland Key, FL Homes

Section Image
    • /61

      Est $2,624,359 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,042 Sq Ft

      20886 4th Ave W, Summerland Key, FL 33042

      20886 4th Ave W, Summerland Key, FL 33042
  • /31

    $795,000

    • 2 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

    Mark MacLaughlin R.W.A. Realty Inc

    360 W Shore Dr, Summerland Key, FL 33042
  • /14

    $250,000 Sold Feb 24, 2025

    1639 Pine Channel Dr, Little Torch Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 6,725 Sq Ft
    • Built 1975

    Last Sold Summary

    • $37/SF
    • 7 Days On Market

    Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

    1639 Pine Channel Dr, Little Torch Key, FL 33042
    • /39

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft

      701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042
  • /43

    $1,799,999

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

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    Jolly Roger Drive on Cudjoe Key, where custom design meets open water views. This 4-bedroom, 2-bathroom residence showcases a designer kitchen with Viking appliances and high-end finishes, perfect for entertaining. The first floor offers two guest bedrooms, an office, and a full bath, while the second floor features a spacious guest room and the primary suite with a private balcony, ensuite bath,

    Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
  • /29

    $395,000 Sold May 19, 2025

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 5% Below List Price
    • 78 Days On Market

    Current Estimated Value $390,403

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    • /2

      Est $761,000 Not Listed For Sale

      • Studio

      164 Newfound Blvd, Big Pine Key, FL 33043

      164 Newfound Blvd, Big Pine Key, FL 33043
  • /26

    $550,000

    • 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. 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 utility co.

    Rose Dell Keller Williams Key West Compass Realty

    31171 Avenue H, Big Pine Key, FL 33043
  • /2

    $755,000 Sold Apr 24, 2025

    3786 Park Ave, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $642/SF
    • 9 Days On Market

    Current Estimated Value $776,004

    Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    3786 Park Ave, Big Pine Key, FL 33043
    • /2

      Est $380,667 Not Listed For Sale

      • Studio

      2112 San Marco Dr, Big Pine Key, FL 33043

      2112 San Marco Dr, Big Pine Key, FL 33043
  • /34

    $1,650,000

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft

    3167 Stewart Rd, Summerland Key, FL 33042

    This 3-bedroom, 2-bath home provides rare-to-find tranquility and privacy in a pristine natural setting. The two-story cottage embodies Old Florida-style with lovingly maintained stone accents and an expansive covered porch overlooking open water. Inside, modern amenities enhance the home's charm. The updated kitchen opens to the living room, with both rooms featuring a wall of windows to take in

    Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

    3167 Stewart Rd, 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

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

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

      Est $386,667 Not Listed For Sale

      • Studio

      2120 San Marco Dr, Big Pine Key, FL 33043

      2120 San Marco Dr, Big Pine Key, FL 33043
  • /72

    $2,075,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,639 Sq Ft

    30980 Witters Ln, Big Pine Key, FL 33043

    MODERN ISLAND RETREAT ON BOGIE CHANNEL - BIG PINE KEY, FLDiscover the epitome of Lower Keys living in this luxurious 4-bedroom, 3.5-bath CBS pool home, ideally positioned on Bogie Channel with direct boating access. Built in 2022 and offered furnished, this elevated residence combines modern design, coastal charm, and unmatched functionality.Step inside to soaring ceilings, expansive windows, and

    Donna Pezzi Keller Williams Key West Compass Realty

    30980 Witters Ln, Big Pine Key, FL 33043
  • /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

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

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

      Est $507,000 Not Listed For Sale

      • 6,000 Sq Ft

      2078 San Marco Dr, Big Pine Key, FL 33043

      2078 San Marco Dr, Big Pine Key, FL 33043
  • /96

    $2,200,000

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft

    1631 Sunrise Dr, Big Pine Key, FL 33043

    SELLER IS MOTIVATED! All furnishings convey with property if buyer would like. Discover the epitome of waterfront living at Tropical Bay Estates. This 2023 new construction home offers an unparalleled paradise for your family and friends. Begin your days with stunning sunrises, engage in world-class fishing, and soak in breathtaking water views from nearly every part of the house. Encounter the

    John Huebner Premium Properties R.E Service

    1631 Sunrise Dr, Big Pine Key, FL 33043
  • /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

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

    29153 Tulip Ln, Big Pine Key, FL 33043
    • /2

      Est $944,530 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 854 Sq Ft

      31441 Ave F, Big Pine Key, FL 33043

      31441 Ave F, Big Pine Key, FL 33043
  • /28

    $896,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,195 Sq Ft

    22922 Blackbeard Ln, Cudjoe Key, FL 33042

    This 3-bedroom, 2-bathroom stilted home offers 1,200 sq ft of thoughtfully designed space on a spacious canal-front lot.Enjoy the convenience of a 40 ft seawall, 10,000 lb boat lift, outdoor shower, and an enclosed garage with plenty of room for vehicles, boats, and water toys.Inside, the open-concept kitchen, living, and dining areas are equipped with brand-new appliances, ample cabinet space,

    Krystal Thomas eXp Realty LLC

    22922 Blackbeard Ln, Cudjoe Key, FL 33042
  • /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
    • /2

      Est $962,000 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      460 Les Rohde Dr, Ramrod Key, FL 33042

      460 Les Rohde Dr, Ramrod Key, FL 33042
  • /107

    $3,200,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,538 Sq Ft

    747 La Fitte Rd, Summerland Key, FL 33042

    Spectacular open water location, with fabulous views from this newly constructed well-built oceanfront concrete home. Direct ocean or gulf access from massive dock that includes three boat lifts (one 15,000 pound, one 12,000 pound and a 10,000 pound double Waverunner lift). Relax in a large heated/chilled inground pool with a big covered pool patio area which drinks in the Ocean view. Home is

    John L. Markle Keller Williams Realty Premier Properties - Kendall

    747 La Fitte Rd, Summerland Key, FL 33042
  • /25

    $560,000 Sold Nov 21, 2025

    30342 Hibiscus Ln, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft
    • Built 1969

    Last Sold Summary

    • 6% Below List Price
    • $371/SF
    • 230 Days On Market

    Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

    30342 Hibiscus Ln, Big Pine Key, FL 33043
    • /2

      Est $1,183,659 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,508 Sq Ft

      29663 Saratoga Ave, Big Pine Key, FL 33043

      29663 Saratoga Ave, Big Pine Key, FL 33043
  • /34

    $1,149,000

    • 3 Beds
    • 3 Baths
    • 2,143 Sq Ft

    1615 Fern Ave, Big Pine Key, FL 33043

    Don't settle for small spaces! Welcome to this spacious and beautifully updated 3-bedroom, 2.5-bath home nestled on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key. Fully renovated, this two-story home feels open, airy, and inviting throughout.Inside, you'll find a large living room filled with natural light, offering plenty of space for family gatherings. A versatile office/den

    Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    1615 Fern Ave, Big Pine Key, FL 33043
  • /4

    $50,000 Sold Dec 19, 2025

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 41% Below List Price
    • 25 Days On Market

    Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
    • /2

      Est $414,104 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,104 Sq Ft

      31380 Ave G, Big Pine Key, FL 33043

      31380 Ave G, Big Pine Key, FL 33043
  • /50

    $1,725,000

    • 3 Beds
    • 3 Baths
    • 2,172 Sq Ft

    29678 Constitution Ave, Big Pine Key, FL 33043

    2.99% Assumable Loan! Experience the true Keys lifestyle in this beautifully maintained waterfront home. Perfectly situated on a 60-foot wide canal, this fully furnished 3 bedroom/2.5 bath property blends privacy, comfort, and effortless access to both the Gulf and Atlantic. The primary suite boasts a huge walk-in closet and luxurious ensuite bath. The fully equipped kitchen features custom

    Callie Harris Brenda Donnelly Real Estate LLC

    29678 Constitution Ave, Big Pine Key, FL 33043
  • /2

    $50,000 Sold Nov 11, 2025

    Lot P No Name Key, No Name Key, FL 33043

    • Land
    • 0.5 Acre
    • $100,000 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 55 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot P No Name Key, No Name Key, FL 33043
    • /2

      Est $431,000 Not Listed For Sale

      • Studio

      L 39 Rose Dr, Big Pine Key, FL 33043

      L 39 Rose Dr, Big Pine Key, FL 33043
  • /45

    $1,950,000

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft

    489 Sawyer Dr, Summerland Key, FL 33042

    OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    489 Sawyer Dr, Summerland Key, FL 33042
  • /39

    $705,000 Sold Sep 08, 2025

    181 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,090 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $647/SF
    • 7 Days On Market

    Current Estimated Value $707,952

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    181 Doubloon Ln, Summerland Key, FL 33042
    • /2

      Est $240,213 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,087 Sq Ft

      31030 E Ave, Big Pine Key, FL 33043

      31030 E Ave, Big Pine Key, FL 33043
  • /33

    $949,000

    • 2 Beds
    • 3 Baths
    • 1,140 Sq Ft

    151 Cutthroat Dr, Summerland Key, FL 33042

    Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access

    Heather Bennett Keller Williams Key West Compass Realty

    151 Cutthroat Dr, Summerland Key, FL 33042
  • /31

    $735,000 Sold Jun 06, 2025

    27373 Antigua Ln, Ramrod Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Below List Price
    • $619/SF
    • 6 Days On Market

    Current Estimated Value $773,592

    Last Listing Agent Sandra Dolowy KeyIsle Realty

    27373 Antigua Ln, Ramrod Key, FL 33042
    • /2

      Est $387,333 Not Listed For Sale

      • Studio

      117550 Caribe St, Sugarloaf Key, FL 33042

      117550 Caribe St, Sugarloaf Key, FL 33042
  • /45

    $1,550,000

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

    28538 John Silver Rd, Summerland Key, FL 33042

    Experience the best of the Keys lifestyle in this beautifully appointed 3-bedroom, 2-bath home, ideally positioned on a premium corner lot with approximately 236 feet of waterfront along a wide canal. Offering direct and easy access to open water, this property is a dream for boaters and water lovers alike.Step inside to a bright, open layout where expansive windows frame stunning views of

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    28538 John Silver Rd, Summerland Key, FL 33042
  • /5

    $235,000 Sold Sep 09, 2025

    1388 Avenue B, Big Pine Key, FL 33043

    • Land

    Last Sold Summary

    • 33% Below List Price
    • 212 Days On Market

    Current Estimated Value $413,868

    Last Listing Agent Sarah Dolson Keller Williams Key West Compass Realty

    1388 Avenue B, Big Pine Key, FL 33043
    • /2

      Est $315,333 Not Listed For Sale

      • Studio

      27328 St Vincent Ln, Ramrod Key, FL 33042

      27328 St Vincent Ln, Ramrod Key, FL 33042

Showing Results 241 - 280, Page 7 of 18

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