8,608

Summerland Key, FL Homes

Section Image
  • /4

    $50,000

    Sold Dec 19, 2025

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

    • Land
    • 7,450 Sq Ft
    • $292,349 per Acre

    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 $518,106

      Not Listed For Sale

      27418 Jamaica Ln, Ramrod Key, FL 33042

      • Studio
      • 1 Bath
      • Built 1970
      27418 Jamaica Ln, Ramrod Key, FL 33042

      Last Sold Summary

  • /64

    $1,480,000

    New Construction $10K PRICE DROP
    • 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 &

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • /2

    $50,000

    Sold Nov 11, 2025

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

    • Land
    • 21,780 Sq Ft
    • $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

      Not Listed For Sale

      13 Red Legs Ln, Cudjoe Key, FL 33042

      13 Red Legs Ln, Cudjoe Key, FL 33042

      Last Sold Summary

  • /51

    $1,250,000

    • 1 Bed
    • 3 Baths
    • 1,234 Sq Ft

    27001 Overseas Hwy, Ramrod Key, FL 33042

    Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample

    Bobby Coe RE/MAX Keys Connection (KW)

    27001 Overseas Hwy, Ramrod 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 $718,116

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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

      Not Listed For Sale

      12 Red Legs Ln, Cudjoe Key, FL 33042

      12 Red Legs Ln, Cudjoe Key, FL 33042

      Last Sold Summary

  • /46

    $2,200,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    1330 Sugarloaf Blvd, Summerland Key, FL 33042

    A quiet escape with million-dollar views. Situated on an expansive lot of over a quarter-acre, this three-bedroom, two-bathroom home is nestled within the sought-after shores of Sugarloaf Key--tucked away from the highway and just steps from scenic walking and bike paths. The interiors offer a crisp, modern take on coastal comfort, sold fully furnished with a curated collection of new decor and

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    1330 Sugarloaf Blvd, 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 $783,102

    Last Listing Agent Sandra Dolowy KeyIsle Realty

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

      Not Listed For Sale

      0 Crane Blvd, Sugarloaf Key, FL 33042

      0 Crane Blvd, Sugarloaf Key, FL 33042

      Last Sold Summary

  • /50

    $1,595,000

    $70K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,995 Sq Ft

    643 Indies Rd, Summerland Key, FL 33042

    Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

    Greg MacLaren Internet Realty of the Florida Keys

    643 Indies 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 $245,779

    Last Listing Agent Sarah Dolson Keller Williams Key West Compass Realty

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

      Est $1,107,580

      Not Listed For Sale

      17162 Starfish Ln W, Sugarloaf Shores, FL 33042

      • Studio
      17162 Starfish Ln W, Sugarloaf Shores, FL 33042

      Last Sold Summary

  • /68

    $1,399,900

    • 2 Beds
    • 2 Baths
    • 1,312 Sq Ft

    3746 Park Ave, Big Pine Key, FL 33043

    Welcome to your private paradise in the Lower Keys! This beautifully updated 2-bedroom, 2-bathroom two-story home offers the ultimate island escape with unmatched privacy -- no direct neighbors on any side, just peaceful surroundings, tropical landscaping, and the charm of the native Key Deer. Designed for true Florida Keys living, the outdoor space is a showstopper. Enjoy a brand-new heated

    Cabot Brown Compass Florida - Miami Beach

    3746 Park Ave, Big Pine Key, FL 33043
  • /42

    $550,000

    Sold Dec 01, 2025

    27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1984

    Last Sold Summary

    • 19% Below List Price
    • $637/SF
    • 125 Days On Market

    Current Estimated Value $581,777

    Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
    • /2

      Est $454,637

      Not Listed For Sale

      390 W Indies Dr, Ramrod Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,426 Sq Ft
      • Built 1958
      390 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

  • /52

    $2,300,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    30995 Watson Blvd, Big Pine Key, FL 33043

    FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy. The property has a beautiful view over the water and a

    Banks Prevatt Coldwell Banker Schmitt RE Co.

    30995 Watson Blvd, Big Pine Key, FL 33043
  • /28

    $500,000

    Sold Jun 20, 2025

    30952 Baileys Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 575 Sq Ft
    • Built 1958

    Last Sold Summary

    • 13% Below List Price
    • $870/SF
    • 18 Days On Market

    Current Estimated Value $505,438

    Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

    30952 Baileys Ln, Big Pine Key, FL 33043
    • /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

  • /32

    $1,125,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft

    27821 Leeward South Rd, Little Torch Key, FL 33042

    ***OPEN HOUSE*** Sunday May 17th from 11am-1pm. Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan

    Kate Zhang Kylin Realty LLC

    27821 Leeward South Rd, Little Torch 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 $1,090,932

    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

  • /51

    $1,675,000

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    559 Powell Ave, Little Torch Key, FL 33042

    Built in 2019 on a Double Lot! This modern home features three (3) bedrooms and two (2) bathrooms, offering everything you need. It's low maintenance yet packed with amenities. Enjoy a pool, a double lot, an extra-long dock, affordable insurance, a quiet, peaceful neighborhood, and excellent fishing opportunities. Step inside to an open-concept design that boasts a bright & fantastic living room

    Bobby Coe RE/MAX Keys Connection (KW)

    559 Powell Ave, Little Torch 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 $634,831

    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

  • /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
  • /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 $424,000

    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

  • /42

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft

    750 W Indies Dr, Summerland Key, FL 33042

    This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramrod Key. Upstairs there are two bedrooms and one bath, and a large kitchen and living room. Downstairs is a one bedroom, one bathroom bungalow with a complete kitchen! The exterior of the property has several updates, including

    Mary Conklin Action Keys Realty of the Lower FL Keys LLC

    750 W Indies Dr, 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 $971,468

    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

  • /51

    $1,380,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft

    30890 Granada Ave, Big Pine Key, FL 33043

    Welcome to your tropical oasis—where the true spirit of the Florida Keys comes to life. This spacious 3-bedroom waterfront home blends casual island style with relaxed coastal living, offering 1,764 square feet designed for comfort and ease. High ceilings lined with tongue-and-groove wood immediately set the island tone as you enter the open living space. The kitchen flows seamlessly into the

    Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

    30890 Granada Ave, Big Pine Key, FL 33043
  • /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 $1,997,714

    Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

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

      Est $494,568

      Not Listed For Sale

      53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

      • Studio
      53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

      Last Sold Summary

  • /57

    $1,395,000

    $255K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft

    25368 2nd St, Summerland Key, FL 33042

    Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

    Ally Kelley Ocean Sotheby's International

    25368 2nd St, Summerland Key, FL 33042
  • /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 $2,430,460

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1260 Sugarloaf Blvd, 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

  • /46

    $1,269,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    116 Spanish Main Dr, Summerland Key, FL 33042

    Discover your personal sanctuary in the heart of Cudjoe Key, where authentic Florida Keys charm meets modern coastal luxury. This stunning 2-bedroom, 2-bathroom home has been thoughtfully updated to offer the ultimate waterfront lifestyle, just 21 miles from Key West's world-class dining and entertainment. The interior glows with natural light, highlighted by impact-resistant windows and elegant

    Lissete Cadwell, P.A. Hawks Cay Resort Sales LLC

    116 Spanish Main Dr, 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 $528,831

    Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

    31525 Avenue A, Big Pine Key, FL 33043

Showing Results 241 - 280, Page 7 of 18

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