8,476

Summerland Key, FL Homes

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    • /2

      Not Listed For Sale

      1138 Basque Ln, Summerland Key, FL 33042

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

  • /64

    $549,000

    • 3 Beds
    • 1 Bath
    • 1,389 Sq Ft

    2828 Central Ave, Big Pine Key, FL 33043

    Peaceful Big Pine Key retreat nestled within the beautiful National Key Deer Wildlife Refuge. This ground-level 3-bedroom, 1-bath concrete home offers the laid-back Keys lifestyle surrounded by lush, mature tropical landscaping and abundant natural beauty.The fully fenced yard provides privacy and space to enjoy the peaceful setting, while the durable metal roof and hurricane shutters add

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    2828 Central Ave, Big Pine Key, FL 33043
  • /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
    • /61

      Est $2,845,053

      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

      • 66 Days On Market

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  • /50

    $2,300,000

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

    30995 Watson Blvd, Big Pine Key, FL 33043

    Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, metal roof, stainless steel appliances, quartz countertops, open-concept living, screened porch, private pool, and covered parking below. Built for coastal living, the CBS structure, impact openings, elevated design,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real E

    30995 Watson Blvd, Big Pine Key, FL 33043
  • /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 $1,683,143

    Last Listing Agent Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
    • /2

      Est $238,779

      Not Listed For Sale

      31380 Ave G, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,104 Sq Ft
      • Built 1971
      31380 Ave G, Big Pine Key, FL 33043

  • /59

    $649,000

    New Construction $5K PRICE INCREASE
    • 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

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
  • /156

    $1,400,000

    Sold Jul 23, 2026

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft
    • Built 2024

    Last Sold Summary

    • 12% Below List Price
    • $655/SF
    • 324 Days On Market

    Current Estimated Value $1,509,137

    Last Listing Agent NON-MLS MEMBER MAR NON MLS MEMBER

    142 Peg Leg Ln, Cudjoe Key, FL 33042
    • /6

      Not Listed For Sale

      31450 Avenue C, Big Pine Key, FL 33043

      • 2 Beds
      • 1 Bath
      • 480 Sq Ft
      • Built 1963
      31450 Avenue C, Big Pine Key, FL 33043

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Kirksten Irick Preferred Properties (KW)

  • /47

    $649,000

    New Construction
    • 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

    701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
  • /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 RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
    • /107

      Est $5,194,037

      Not Listed For Sale

      220 E Caribbean Dr, Summerland Key, FL 33042

      • 5 Beds
      • 7 Baths
      • 4,981 Sq Ft
      • Built 2025
      220 E Caribbean Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 165 Days On Market

      Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  • /22

    $899,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft

    23940 Overseas Hwy, Summerland Key, FL 33042

    Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating,

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    23940 Overseas Hwy, Summerland Key, FL 33042
  • /57

    $1,250,000

    Sold Jun 30, 2026

    25368 2nd St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1958

    Last Sold Summary

    • 24% Below List Price
    • $898/SF
    • 241 Days On Market

    Current Estimated Value $1,536,000

    Last Listing Agent Ally Kelley Ocean Sotheby's International

    25368 2nd St, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      28131 Helen Ave, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 856 Sq Ft
      • Built 1972
      28131 Helen Ave, Little Torch Key, FL 33042

  • /36

    $949,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,052 Sq Ft

    273 Indies Rd, Summerland Key, FL 33042

    Welcome to this bright and modern 2-bedroom, 2-bath home located in the desirable Breezeswept Beach Estates on Ramrod Key. Completed in 2024 by the builder with high-quality features including a metal roof, impact windows, new A/C, and durable Hardi board siding. This home was later purchased and further upgraded by the current owner, who is also the first to live in the home. Since purchasing,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    273 Indies Rd, Summerland 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 $1,044,958

    Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

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

      Est $223,400

      Not Listed For Sale

      27328 St Vincent Ln, Ramrod Key, FL 33042

      • Studio
      27328 St Vincent Ln, Ramrod Key, FL 33042

  • /9

    $1,300,000

    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft

    486 Airport Dr S, Summerland Key, FL 33042

    Summerland Key Cove -- Come by Sea or by PlaneA unique opportunity in Summerland Key Cove offering both canal-front living and access to the community's private airport. Whether your Florida Keys lifestyle revolves around boating, flying, fishing, diving, or simply enjoying the water, this property offers a combination that is increasingly hard to find.Built in 1982, this 1,240

    Rose Dell Keller Williams Key West Compass Realty

    486 Airport Dr S, 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 $3,091,861

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

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

      Est $837,162

      Not Listed For Sale

      29654 Constitution Ave, Big Pine Key, FL 33043

      • 4 Beds
      • 2 Baths
      • 1,547 Sq Ft
      • Built 1963
      29654 Constitution Ave, Big Pine Key, FL 33043

  • /32

    $1,174,000

    $125K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,774 Sq Ft

    30525 Winifred St, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a

    Joyce Craul Expert Realty LLC (HQ)

    30525 Winifred St, Big Pine Key, FL 33043
  • /9

    $360,000

    Sold Aug 25, 2026

    27917 Coral Shores Rd, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1972

    Last Sold Summary

    • 10% Below List Price
    • $268/SF
    • 52 Days On Market

    Last Listing Agent Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

    27917 Coral Shores Rd, Summerland Key, FL 33042
    • /2

      Est $757,368

      Not Listed For Sale

      1313 State Rd Unit 4A, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 990 Sq Ft
      • Built 1977
      1313 State Rd Unit 4A, Little Torch Key, FL 33042

  • /29

    $750,000

    $50K 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
  • /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
    • /37

      Est $1,629,372

      Not Listed For Sale

      2256 Matthews Rd, Big Pine Key, FL 33043

      • 4 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 2024
      2256 Matthews Rd, Big Pine Key, FL 33043

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • /26

    $525,000

    $50K 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 dining area to Covered Porch. Laundry closet. Garage and Storage. Concrete covered patio or parking. 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

    Rose Dell Keller Williams Key West Compass Realty

    31171 Avenue H, Big Pine Key, FL 33043
  • /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 $1,399,166

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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

      Not Listed For Sale

      23008 Overseas Hwy, Cudjoe Key, FL 33042

      23008 Overseas Hwy, Cudjoe Key, FL 33042

  • /62

    $2,499,000

    $100K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 2,224 Sq Ft

    16843 E Point Dr, Summerland Key, FL 33042

    Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle.Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious

    Suzanne Moore Suzanne Moore Real Estate

    16843 E Point Dr, 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 $1,276,363

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    29436 Independence Ave, Big Pine Key, FL 33043
    • /13

      Est $278,845

      Not Listed For Sale

      31014 Avenue E, Big Pine Key, FL 33043

      • 1 Bed
      • Built 1969
      31014 Avenue E, Big Pine Key, FL 33043

      Last Sold Summary

      • 103 Days On Market

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

  • /36

    $750,000

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

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

    Prime residential lot opportunity in Key Colony Beach, Monroe County, located at 0 Niles Rd, Key Colony, FL 33042. This approximately 9.2-acre property is situated in the Florida Keys with convenient access to nearby points of interest including Murray's Market (0.45 miles), Big Pine Key Boat Rentals (0.6 miles), Merrill Homes Inc (0.6 miles), and WWUS-FM Big Pine Key (1.85 miles). The

    Javier Santana Sunland Real Estate, LLC.

    0 Niles Rd Unit MLS A11925960, Summerland 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 $625,269

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

    150 Coral Ave, Summerland Key, FL 33042
    • /4

      Est $265,658

      Not Listed For Sale

      31373 Avenue C, Big Pine Key, FL 33043

      • 2 Beds
      • Built 1971
      31373 Avenue C, Big Pine Key, FL 33043

      Last Sold Summary

      • 116 Days On Market

      Last Listing Agent Karen Liskey Key Colony Beach Realty

  • /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

    17387 E Dolphin St, Sugarloaf 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 $372,542

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

    29153 Tulip Ln, Big Pine Key, FL 33043
    • /28

      Est $1,843,133

      Not Listed For Sale

      27385 St Lucie Ln, Ramrod Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,988 Sq Ft
      • Built 1987
      27385 St Lucie Ln, Ramrod Key, FL 33042

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Kathleen Gomez Coldwell Banker Schmitt RE Co.

Showing Results 241 - 280, Page 7 of 18

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