8,633

Summerland Key, FL Homes

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  • /52

    $1,195,000

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

    29534 Geraldine St, Big Pine Key, FL 33043

    Turnkey and move-in ready, this exceptional waterfront home is being offered fully furnished--including furniture, dishes, cookware, and linens--so you can start enjoying the Florida Keys lifestyle from day one. Situated on an oversized 18,000 sq. ft. double lot with 150' of canal frontage in a quiet, peaceful Big Pine Key boating community, this solid concrete 3BD/2BA home features a desirable

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    29534 Geraldine St, Big Pine Key, FL 33043
  • /19

    $4,500 Per Month

    • 2 Beds
    • 1 Bath
    • 884 Sq Ft
    • House for Rent

    27346 Martinique Ln, Summerland Key, FL 33042

    Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

    Alicia Rufino Island Living Realty, LLC

    27346 Martinique Ln, Summerland Key, FL 33042
  • /2

    $510,000

    Sold Sep 08, 2025

    Unlisted Address

    • 3 Beds
    • 2 Baths
    • 972 Sq Ft
    • Built 1989

    Last Sold Summary

    • $525/SF

    Current Estimated Value $534,084

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    Unlisted Address
    • /14

      Not Listed For Sale

      1639 Pine Channel Dr, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 6,725 Sq Ft
      • Built 1975
      1639 Pine Channel Dr, Little Torch Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

  • /51

    $2,499,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    27348 Dominica Ln, Ramrod Key, FL 33042

    Welcome to your waterfront retreat on Ramrod Key, where beautiful open water views, quick ocean access, and exceptional outdoor living create the ultimate Florida Keys lifestyle. Built by renowned Tom Ryan in 2007, this well-maintained 3-bedroom, 2-bath home is designed for both relaxation and adventure. Step inside to a bright, open-concept living area featuring a spacious kitchen with ample

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    27348 Dominica Ln, Ramrod Key, FL 33042
  • /3

    $510,000

    Sold Jun 18, 2026

    57 Pelican Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $538/SF
    • 23 Days On Market

    Current Estimated Value $545,931

    Last Listing Agent Elsa Machado Elsa Realty, LLC

    57 Pelican Ln, Big Pine Key, FL 33043
    • /29

      Not Listed For Sale

      1693 Bayview Dr, Little Torch Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 917 Sq Ft
      • Built 1976
      1693 Bayview Dr, Little Torch Key, FL 33042

      Last Sold Summary

      • 60 Days On Market

  • /46

    $824,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,980 Sq Ft

    30937 Baileys Ln, Big Pine Key, FL 33043

    Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    30937 Baileys Ln, Big Pine Key, FL 33043
  • /65

    $4,000

    Sold Jul 06, 2026

    30361 Hardin Rd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 888 Sq Ft
    • Built 1963

    Last Sold Summary

    • 20% Below List Price
    • $5/SF
    • 79 Days On Market

    Current Estimated Value $803,670

    Last Listing Agent Maris Delgado LoKation Real Estate - Key Largo

    30361 Hardin Rd, Big Pine Key, FL 33043
    • /29

      Not Listed For Sale

      701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 828 Sq Ft
      • Built 2001
      701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

      Last Sold Summary

      • 14 Days On Market

  • /68

    $3,199,000

    • 3 Beds
    • 3 Baths
    • 1,586 Sq Ft

    1148 Big Pine Ave, Big Pine Key, FL 33043

    If you've been dreaming of the kind of place where the sunsets stop you in your tracks...this is it. Tucked away on a quiet road in Big Pine Key, this 2 Bedroom 2 Bath plus 1 Bedroom 1 Bath Guest Cottage one-of-a-kind point property delivers something incredibly rare in the Florida Keys, open water views and protected dockage, all wrapped into a private tropical setting on over an acre and a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1148 Big Pine Ave, Big Pine Key, FL 33043
  • /58

    $572,000

    Sold May 27, 2026

    175 E Cahill Ct, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $567/SF
    • 40 Days On Market

    Current Estimated Value $587,875

    Last Listing Agent Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    175 E Cahill Ct, Big Pine Key, FL 33043
    • /15

      Not Listed For Sale

      8 Calico Jack Circle Cir, Verifying, FL 33042

      8 Calico Jack Circle Cir, Verifying, FL 33042

      Last Sold Summary

      • 18 Days On Market

  • /37

    $725,000

    $25K PRICE DROP
    • 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

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    29160 Primrose Ln, Big Pine Key, FL 33043
  • /38

    $790,000

    Sold May 22, 2026

    30471 Coconut Hwy, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Built 1959

    Last Sold Summary

    • 14% Below List Price
    • $522/SF
    • 319 Days On Market

    Current Estimated Value $785,638

    Last Listing Agent Richard Haskins Buy The Keys

    30471 Coconut Hwy, Big Pine Key, FL 33043
    • /59

      Not Listed For Sale

      701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

      Last Sold Summary

      • 76 Days On Market

  • /44

    $1,200,000

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

    17286 Jamaica Ln, Summerland Key, FL 33042

    Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17286 Jamaica Ln, Summerland Key, FL 33042
  • /16

    $1,400,000

    Sold Mar 16, 2026

    570 Blackbeard Rd, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Below List Price
    • $933/SF
    • 14 Days On Market

    Current Estimated Value $1,400,500

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    570 Blackbeard Rd, Summerland Key, FL 33042
    • /40

      Not Listed For Sale

      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1996
      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

  • /54

    $1,049,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    22953 John Silver Ln, Summerland Key, FL 33042

    Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    22953 John Silver Ln, Summerland Key, FL 33042
  • /61

    $592,000

    Sold May 29, 2026

    29951 Pine Channel Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft
    • Built 1989

    Last Sold Summary

    • 9% Below List Price
    • $649/SF
    • 80 Days On Market

    Current Estimated Value $588,281

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    29951 Pine Channel Rd, Big Pine Key, FL 33043
    • /37

      Not Listed For Sale

      27883 Coral Shores Rd, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1973
      27883 Coral Shores Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 9 Days On Market

  • /66

    $799,000

    $50K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 842 Sq Ft

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

    Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
  • /125

    $5,000,000

    Sold Jun 18, 2026

    24200 Overseas Hwy, Summerland Key, FL 33042

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 19% Below List Price
    • $1,667/SF
    • 106 Days On Market

    Current Estimated Value $4,618,358

    Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

    24200 Overseas Hwy, Summerland Key, FL 33042
    • /64

      Not Listed For Sale

      15 W Cooks, Cook Island Key, FL 33043

      • 3 Beds
      • 3 Baths
      • 1,551 Sq Ft
      • Built 1977
      15 W Cooks, Cook Island Key, FL 33043

      Last Sold Summary

      • 16 Days On Market

  • /76

    $1,550,000

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    29424 Forrestal Ave, Big Pine Key, FL 33043

    If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    29424 Forrestal Ave, Big Pine Key, FL 33043
  • /45

    $780,000

    Sold Jul 18, 2025

    29025 Geranium Dr, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft
    • Built 1981

    Last Sold Summary

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

    Current Estimated Value $789,511

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    29025 Geranium Dr, Big Pine Key, FL 33043
    • /50

      Est $833,230

      Not Listed For Sale

      489 Pirates Rd, Little Torch Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 1,638 Sq Ft
      • Built 1984
      489 Pirates Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 38 Days On Market

  • /62

    $1,299,999

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    28560 Doubloon Rd, Summerland Key, FL 33042

    Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    28560 Doubloon Rd, Summerland Key, FL 33042
  • /49

    $650,000

    Sold Aug 20, 2025

    27317 Cayman Ln, Summerland Key, FL 33042

    • 2 Beds
    • 1.5 Baths
    • 1,029 Sq Ft
    • Built 2012

    Last Sold Summary

    • 28% Below List Price
    • $632/SF
    • 262 Days On Market

    Current Estimated Value $709,465

    Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

    27317 Cayman Ln, Summerland Key, FL 33042
    • /54

      Not Listed For Sale

      701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1999
      701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

      Last Sold Summary

      • 194 Days On Market

  • /21

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,304 Sq Ft

    75 Lobstertail Rd, Big Pine Key, FL 33043

    Enjoy easy island living in this beautifully updated 2BD/2BA elevated home set along a peaceful plugged canal--perfect for paddleboarding and enjoying the waterfront ambiance (no boating access).Inside, the open living space features vaulted ceilings, luxury plank vinyl flooring throughout, and great natural light, flowing out to a screened porch overlooking the canal. The standout chef's

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    75 Lobstertail Rd, Big Pine Key, FL 33043
  • /5

    $725,000

    Sold Jul 30, 2025

    19462 Canal Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,394 Sq Ft
    • Built 1990

    Last Sold Summary

    • 6% Below List Price
    • $520/SF
    • 3 Days On Market

    Current Estimated Value $748,620

    Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

    19462 Canal Dr, Summerland Key, FL 33042
    • /35

      Est $235,021

      Not Listed For Sale

      701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

  • /40

    $1,899,000

    $100K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 1,998 Sq Ft

    28573 Le Grand Rd, Little Torch Key, FL 33042

    This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    28573 Le Grand Rd, Little Torch Key, FL 33042
  • /2

    $55,000

    Sold Oct 22, 2025

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,000 Sq Ft
    • $479,160 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 2 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042
    • /51

      Not Listed For Sale

      701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2006
      701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

      Last Sold Summary

      • 27 Days On Market

  • /48

    $698,800

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,039 Sq Ft

    29048 Iris Dr, Big Pine Key, FL 33043

    This 50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    29048 Iris Dr, Big Pine Key, FL 33043
  • /49

    $280,000

    Sold Jun 03, 2026

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Built 1976

    Last Sold Summary

    • $406/SF
    • 98 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    • /9

      Not Listed For Sale

      Lots 23-24 Coral Way, Big Pine Key, FL 33043

      Lots 23-24 Coral Way, Big Pine Key, FL 33043

      Last Sold Summary

      • 24 Days On Market

Showing Results 41 - 80, Page 2 of 18

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