8,476

Summerland Key, FL Homes

Section Image
  • /49

    $820,000

    • 2 Beds
    • 2 Baths
    • 1,076 Sq Ft

    1817 Watson Blvd, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this 2-bedroom, 2-bath canal-front ranch style home offers a rare opportunity to enjoy the Florida Keys lifestyle while investing for exceptional future potential. Situated on an oversized 1 1/2 lot with direct boating access out to open water in 3 mins, this property is a true waterfront gem. The existing home provides comfortable island living with abundant

    Paul Rogers Coldwell Banker Schmitt RE Co.

    1817 Watson Blvd, Big Pine Key, FL 33043
  • /55

    $1,035,000

    Sold Apr 01, 2026

    231 W Indies Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $752/SF
    • 173 Days On Market

    Current Estimated Value $1,079,815

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    231 W Indies Dr, Summerland Key, FL 33042
    • /21

      Est $818,731

      Not Listed For Sale

      19570 Mayan St, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,424 Sq Ft
      • Built 1958
      19570 Mayan St, Summerland Key, FL 33042

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Thomas Mack SBX Real Estate, LLC (KW)

  • /20

    $4,200

    Pending
    • 2 Beds
    • 2 Baths
    • 1,332 Sq Ft

    1129 Gordon Dr, Big Pine Key, FL 33043

    Tropical Island Living in Big Pine Key! Welcome to your slice of paradise! This beautifully renovated property offers: a long term residential lease for 1 yearTwo bedroom and two bathrooms for $4,200 +$300 for one monthly cleaning. plus $175 additional for the yard care and utility expenses energy, water, propane for generator. Tank will be full at commencement of lease. Upstairs: A fully

    Jennifer Howe Coastal Collection Real Estate Inc.

    1129 Gordon Dr, Big Pine Key, FL 33043
  • /19

    $595,000

    Sold Jun 02, 2026

    27147 Dolphin Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1991

    Last Sold Summary

    • 8% Below List Price
    • $539/SF
    • 50 Days On Market

    Current Estimated Value $599,838

    Last Listing Agent Robin Nilsson Keller Williams Key West Compass Realty

    27147 Dolphin Rd, Summerland Key, FL 33042
    • /73

      Est $1,119,110

      Not Listed For Sale

      103 Shore Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,128 Sq Ft
      • Built 1989
      103 Shore Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Stephany Duvall Engel & Völkers Marathon

  • /9

    $800,000

    • Land
    • 7,840 Sq Ft
    • $4,444,444 per Acre

    28525 Jolly Roger Dr, Little Torch Key, FL 33042

    Rare actively permitted waterfront homesite with existing concrete seawall/dock on Little Torch Key with exceptional boating access, approved engineered house plans, and protected salt-pond and nature-preserve views across the street. The property is offered with an active Monroe County building permit and approved plans for an elevated concrete 3-bedroom, 2-bath residence with approximately

    Nate Meyer Meyer and Boumerhi Realty LLC

    28525 Jolly Roger Dr, Little Torch Key, FL 33042
  • /2

    $553,000

    Sold Mar 06, 2026

    3 W Cook, Cook Island Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 750 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $737/SF
    • 312 Days On Market

    Current Estimated Value $460,667

    Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

    3 W Cook, Cook Island Key, FL 33043
    • /46

      Est $1,372,118

      Not Listed For Sale

      817 Grenada Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 1,819 Sq Ft
      • Built 1993
      817 Grenada Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Melissa Graham Bluescape Real Estate

  • /7

    $170,000

    • Land
    • 5,662 Sq Ft
    • $1,307,692 per Acre

    Lot 27 Dorn Rd, Torch Key, FL 33042

    If you love fishing, love the water, and hate the big crowds, this is the place for you! Upon arrival, the first thing you will notice is the peace and quiet. Easy access to the Gulf of America and Atlantic Ocean. This property is adjacent to my other listing which is owned by the same person. This would be an excellent opportunity to own a double lot on Big Torch Key! Adjacent property (blue

    Dylan Calhoun Luxe Properties

    Lot 27 Dorn Rd, Torch Key, FL 33042
  • /35

    $669,000

    Sold Oct 24, 2025

    28212 Gato Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,077 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $621/SF
    • 80 Days On Market

    Current Estimated Value $695,187

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    28212 Gato Rd, Summerland Key, FL 33042
    • /2

      Est $749,551

      Not Listed For Sale

      27312 Anguila Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,148 Sq Ft
      • Built 1989
      27312 Anguila Ln, Summerland Key, FL 33042

  • /42

    $727,000

    $58K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,224 Sq Ft

    31033 Hibiscus Dr, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Or you may just want to demo the house and build your Keys Dream Home on two

    Karen Haack Coldwell Banker Schmitt RE Co.

    31033 Hibiscus Dr, Big Pine Key, FL 33043
  • /45

    $1,910,000

    Sold Feb 26, 2026

    1659 Long Beach Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $1,146/SF
    • 7 Days On Market

    Current Estimated Value $1,931,493

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1659 Long Beach Dr, Big Pine Key, FL 33043
    • /41

      Est $1,079,769

      Not Listed For Sale

      366 Sawyer Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,390 Sq Ft
      • Built 1988
      366 Sawyer Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  • /6

    $240,000

    Pending
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    28177 Julia Ave, Little Torch Key, FL 33042

    Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5

    Maria Acosta Keller Williams Capital Realty

    28177 Julia Ave, Little Torch Key, FL 33042
  • /12

    $650,000

    Sold Jul 08, 2026

    0 Dominica Ln Unit 615842, Ramrod Key, FL 33042

    • Land
    • 12,632 Sq Ft
    • $2,241,379 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 308 Days On Market

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
    • /44

      Est $801,491

      Not Listed For Sale

      268 Spanish Main Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1979
      268 Spanish Main Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Ally Kelley Ocean Sotheby's International

  • /49

    $1,450,000

    $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft

    29635 Saratoga Ave, Big Pine Key, FL 33043

    Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This beautifully built 3bedroom, 2bath CBS home offers the perfect blend of durability, comfort, and laid-back Keys living. Constructed with poured concrete floors and designed for peace of mind, the home features a tiled interior, a tiled roof, and convenient accordion shutters throughout. Step outside and embrace

    Karen Haack Coldwell Banker Schmitt RE Co.

    29635 Saratoga Ave, Big Pine Key, FL 33043
  • /52

    $2,300,000

    Sold Sep 12, 2025

    23086 Snapper Ln, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,586 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $889/SF
    • 147 Days On Market

    Current Estimated Value $2,244,810

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    23086 Snapper Ln, Summerland Key, FL 33042
    • /29

      Est $1,364,178

      Not Listed For Sale

      17081 Starfish Ln W, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,542 Sq Ft
      • Built 1980
      17081 Starfish Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 175 Days On Market

      Last Listing Agent Sean Farrer Coldwell Banker Schmitt RE Co

  • /40

    $4,400,000

    New Construction $75K PRICE INCREASE
    • 5 Beds
    • 5.5 Baths
    • 3,119 Sq Ft

    231 E Shore Dr Unit 6, Summerland Key, FL 33042

    Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

    Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 6, Summerland Key, FL 33042
  • /32

    $455,000

    Sold Feb 25, 2026

    31129 Avenue G, Big Pine Key, FL 33043

    • 3 Beds
    • 2.5 Baths
    • 844 Sq Ft
    • Built 1994

    Last Sold Summary

    • $539/SF
    • 52 Days On Market

    Last Listing Agent Ted Stewart Truman & Co. (KW)

    31129 Avenue G, Big Pine Key, FL 33043
    • /36

      Est $988,789

      Not Listed For Sale

      21066 3rd Ave, Summerland Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 1,245 Sq Ft
      • Built 1974
      21066 3rd Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 326 Days On Market

      Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  • /7

    $1,600,000

    • Land
    • 1.01 Acres
    • $1,584,158 per Acre

    0 Racoon Run, Big Pine Key, FL 33043

    Rare opportunity to own 1 acre in beautiful Big Pine Key, Florida! Build your dream island retreat in one of the most desirable areas of the Lower Keys. Enjoy the natural beauty, tropical surroundings, boating, fishing, snorkeling, and the laid-back Florida Keys lifestyle. Big Pine Key is known for its peaceful atmosphere, abundant wildlife, and proximity to the National Key Deer Refuge.

    Sara Baldomero Ribot HOME PRIME REALTY LLC

    0 Racoon Run, Big Pine Key, FL 33043
  • /22

    $649,000

    Sold May 20, 2026

    19591 Navajo St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft
    • Built 1994

    Last Sold Summary

    • 4% Below List Price
    • $624/SF
    • 25 Days On Market

    Current Estimated Value $657,807

    Last Listing Agent Mike Kane Internet Realty of the Florida Keys

    19591 Navajo St, Summerland Key, FL 33042
    • /27

      Est $864,199

      Not Listed For Sale

      27417 Cayman Ln, Summerland Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 1,085 Sq Ft
      • Built 1975
      27417 Cayman Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 274 Days On Market

      Last Listing Agent Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  • /72

    $595,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

    Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
  • /29

    $1,400,000

    Sold Apr 24, 2026

    20841 8th Ave W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $748/SF
    • 82 Days On Market

    Current Estimated Value $1,459,775

    Last Listing Agent Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

    20841 8th Ave W, Summerland Key, FL 33042
    • /43

      Est $942,527

      Not Listed For Sale

      447 Pirates Rd, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 984 Sq Ft
      • Built 1991
      447 Pirates Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Jennifer Newman Truman & Co. (KW)

  • /3

    $215,000

    • Land
    • 7,840 Sq Ft
    • $1,194,444 per Acre

    27334 Saint Lucie Ln, Big Pine, FL 33042

    Rare opportunity to own a piece of paradise in the heart of the Florida Keys. Located in the desirable Breezeswept Beach Estates community on Ramrod Key, this canal-front homesite offers the perfect blend of tranquility, natural beauty, and island living. The property benefits from a recorded Lot Line Adjustment that established the current buildable lot configuration, creating an excellent

    Gilberto Imery Gilvan Realty Corp

    27334 Saint Lucie Ln, Big Pine, FL 33042
  • /59

    $900,000

    Sold Oct 31, 2025

    28550 Doubloon Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,371 Sq Ft
    • Built 1996

    Last Sold Summary

    • 18% Below List Price
    • $380/SF
    • 181 Days On Market

    Current Estimated Value $926,696

    Last Listing Agent Kelly Randin Sharon J. Kelly Realty, Inc.

    28550 Doubloon Rd, Summerland Key, FL 33042
    • /27

      Est $2,122,867

      Not Listed For Sale

      17022 Starfish Ln W, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,990 Sq Ft
      • Built 1994
      17022 Starfish Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

  • /50

    $1,349,000

    $100K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 1,820 Sq Ft

    845 Pirates Rd, Summerland Key, FL 33042

    Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to open water, making it ideal for fishing and island adventures.Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas overlooking the canal. Boaters will

    Sandra Dolowy KeyIsle Realty

    845 Pirates Rd, Summerland Key, FL 33042
  • /47

    $1,100,000

    Sold Jun 12, 2026

    43 Venetian Way, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Built 1982

    Last Sold Summary

    • 17% Below List Price
    • $880/SF
    • 497 Days On Market

    Current Estimated Value $1,104,521

    Last Listing Agent Lori Cameron Buy The Keys

    43 Venetian Way, Summerland Key, FL 33042
    • /2

      Est $1,334,360

      Not Listed For Sale

      23047 Bluegill Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,440 Sq Ft
      • Built 1991
      23047 Bluegill Ln, Summerland Key, FL 33042

  • /49

    $890,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    813 Hawksbill Ln, Summerland Key, FL 33042

    Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board siding and a metal roof, this three-story retreat of island living. with GENERAC Generator. Inside, you'll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly

    Miguel Solis Berkshire Hathaway HomeServices EWM Realty - Coral Gables

    813 Hawksbill Ln, Summerland Key, FL 33042
  • /49

    $1,275,000

    Sold Jul 22, 2026

    1709 Sunrise Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $685/SF
    • 12 Days On Market

    Current Estimated Value $1,279,664

    Last Listing Agent Paige Bethel Island Home Realty Inc.

    1709 Sunrise Dr, Big Pine Key, FL 33043
    • /20

      Est $837,444

      Not Listed For Sale

      27370 W Indies Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1992
      27370 W Indies Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  • /51

    $749,900

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft

    1821 Bittersweet Ave, Big Pine Key, FL 33043

    A Boating/Fishing Dream Home....This Canal Front Stilt home sits on an oversized corner lot, in ''Key Deer Refuge'', beautiful wild-life and Key Deer abound, 2/bedroom, 2/bath, a 3rd bonus room, you may use as a bedroom or office, a spacious Living/Dining/Kitchen with lots of light, stainless appliances, impact windows, Bamboo/tile floors. Enjoy the Florida Keys Lifestyle on your Boat docked

    Brenda Alexander Lokation Real Estate

    1821 Bittersweet Ave, Big Pine Key, FL 33043

Showing Results 521 - 560, Page 14 of 18

How to Buy a Home How to Finance a Home How to Sell a Home