Summerland Key, FL Homes

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  /4

  $2,499,000

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  32029 Marginella Dr, Big Pine Key, FL 33043

  Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stone's throw away from Big Pine Key, this nearly 2-acre property presents

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

  32029 Marginella Dr, Big Pine Key, FL 33043
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  /2

  $570,000 Sold Jul 17, 2025

  3767 Hibiscus St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $594/SF
  • 6 Days On Market

  Current Estimated Value $592,045

  Last Listing Agent Ryan Call REALTY ZOOM

  3767 Hibiscus St, Big Pine Key, FL 33043
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  /2

  Est $766,978 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  22775 Privateer Dr, Summerland Key, FL 33042

  22775 Privateer Dr, Summerland Key, FL 33042
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  /61

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

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

  Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom 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 cozy and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
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  /44

  $876,000 Sold Apr 29, 2025

  30751 Palm Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $508/SF
  • 156 Days On Market

  Current Estimated Value $921,442

  Last Listing Agent Melissa Graham Bluescape Real Estate

  30751 Palm Dr, Big Pine Key, FL 33043
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  /39

  Est $957,759 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  22716 Privateer Dr, Summerland Key, FL 33042

  22716 Privateer Dr, Summerland Key, FL 33042
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  /94

  $3,875,000

  • 4 Beds
  • 4 Baths
  • 2,766 Sq Ft

  414 Caribbean Dr E, Summerland Key, FL 33042

  Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft.

  Lisa Swanson The Agency Florida Keys

  414 Caribbean Dr E, Summerland Key, FL 33042
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  /41

  $1,375,000 Sold Mar 13, 2025

  20785 5th Ave W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $917/SF
  • 77 Days On Market

  Current Estimated Value $1,358,706

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

  20785 5th Ave W, Summerland Key, FL 33042
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  /29

  Est $906,204 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  27359 Jamaica Ln, Summerland Key, FL 33042

  27359 Jamaica Ln, Summerland Key, FL 33042
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  /47

  $1,150,000

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

  43 Venetian Way, Summerland Key, FL 33042

  Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

  Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
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  /40

  $680,000 Sold Mar 20, 2025

  27337 Tobago Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1958

  Last Sold Summary

  • 1% Above List Price
  • $630/SF
  • 7 Days On Market

  Current Estimated Value $712,085

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

  27337 Tobago Ln, Summerland Key, FL 33042
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  /2

  Est $1,031,115 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  479 Blackbeard Rd, Summerland Key, FL 33042

  479 Blackbeard Rd, Summerland Key, FL 33042
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  /59

  $2,950,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft

  20844 4th Ave W, Summerland Key, FL 33042

  SOLD TURNKEY! PRICE INCLUDES FURNISHINGS, 2006 PONTOON BOAT & 2021 JET SKI! A remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up one of the two brick paver driveways on this over sized lot you will find two entrances, beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning concrete residence

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, Summerland Key, FL 33042
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  /107

  $5,300,000 Sold Jun 13, 2025

  220 E Caribbean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 7 Baths
  • 4,981 Sq Ft
  • Built 2025

  Last Sold Summary

  • 18% Below List Price
  • $1,064/SF
  • 165 Days On Market

  Current Estimated Value $5,003,432

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  220 E Caribbean Dr, Summerland Key, FL 33042
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  /29

  Est $792,210 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft

  22774 Cudjoe Dr, Summerland Key, FL 33042

  22774 Cudjoe Dr, Summerland Key, FL 33042
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  /18

  $839,000

  • 4 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  1433 Sunset Rd, Big Pine Key, FL 33043

  Great income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogie Channel. Large lot with full seawall. Interior is cute and tidy and would be easy to rent or live in one side and generate extra income. Fully furnished.

  Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  1433 Sunset Rd, Big Pine Key, FL 33043
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  /2

  $1,650,000 Sold Sep 03, 2025

  743 E Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $944/SF
  • 1 Day On Market

  Current Estimated Value $1,668,752

  Last Listing Agent Scott Brisson KeyIsle Realty

  743 E Shore Dr, Summerland Key, FL 33042
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  /23

  Est $769,585 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  283 Pirates Rd, Summerland Key, FL 33042

  283 Pirates Rd, Summerland Key, FL 33042
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  /2

  $399,000 Pending

  • Land

  31145 Hibiscus Dr, Big Pine Key, FL 33043

  Ready..Set.. Build!! No waiting for permit allocation. Beautiful brand-new modular home. All up to current Florida Building Code. No revisions needed. Permit in hand for 3 bed/2 bath home with ample sized rooms and several upgrades in place. 2 porches and 1320 S.F. living space. Concrete slab and lower enclosure. Great boating access just a minute to Bogie Channell. Plans and survey in documents.

  Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  31145 Hibiscus Dr, Big Pine Key, FL 33043
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  /49

  $995,000 Sold Dec 23, 2025

  29462 Geraldine St, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 1991

  Last Sold Summary

  • 9% Below List Price
  • $444/SF
  • 65 Days On Market

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  29462 Geraldine St, Big Pine Key, FL 33043
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  /33

  Est $1,072,046 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  131 W Indies Dr, Summerland Key, FL 33042

  131 W Indies Dr, Summerland Key, FL 33042
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  /25

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  180 Sugarloaf Dr, Summerland Key, FL 33042

  **Motivated Sellers, all reasonable offers considered**This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000sqft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a quaint patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen, bonus screened porch and outdoor seating

  Jenny Perry Preferred Properties (KW)

  180 Sugarloaf Dr, Summerland Key, FL 33042
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  /2

  $49,000 Sold Jun 06, 2025

  7 Lot, Lower Keys, FL 33042

  • Land
  • 0.19 Acre
  • $257,895 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 168 Days On Market

  Last Listing Agent Pamela Stangler MMLS Assoc.-Inactive Member

  7 Lot, Lower Keys, FL 33042
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  /2

  Est $690,479 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft

  19720 Date Palm Dr, Summerland Key, FL 33042

  19720 Date Palm Dr, Summerland Key, FL 33042
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  /37

  $979,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  PROTECTED DOCKAGE! LOOK AT THIS VIEW! You have open water views from this impeccably maintained, fully stilted 2BR/2 BATH unit! A 43' SEAWALL with heavy duty dock posts, cleats, fish cleaning table and swim ladder add to the allure of this home perfect for the avid boater! North winds are NO PROBLEM with this protected dockage! The oversized patio off the main living area upstairs is the perfect

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  /30

  $400,000 Sold Apr 15, 2025

  115 E Cahill Ct, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1976

  Last Sold Summary

  • 11% Below List Price
  • $412/SF
  • 25 Days On Market

  Current Estimated Value $453,655

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  115 E Cahill Ct, Big Pine Key, FL 33043
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  /4

  Est $833,682 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,108 Sq Ft

  27456 Martinique Ln, Summerland Key, FL 33042

  27456 Martinique Ln, Summerland Key, FL 33042
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  /21

  $1,300,000

  • Land
  • 0.17 Acre
  • $7,647,059 per Acre

  31441 Avenue I, Big Pine Key, FL 33043

  Waterfront property located in Big Pine Key, FL ready for you to build your dream house on. Property has a private boat ramp, boat lift, and seawall. ROGO exempt. 2 minutes to Atlantic by boat, 2 minutes to Gulf by boat. Only 30 miles from Key West.

  Nate Hinman HAREONE REALTY GROUP

  31441 Avenue I, Big Pine Key, FL 33043
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  /28

  $510,500 Sold Aug 14, 2025

  31124 Avenue E, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $560/SF
  • 17 Days On Market

  Current Estimated Value $510,882

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  31124 Avenue E, Big Pine Key, FL 33043
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  /45

  Est $1,801,467 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,752 Sq Ft

  19527 Indian Mound Dr, Summerland Key, FL 33042

  19527 Indian Mound Dr, Summerland Key, FL 33042
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  /47

  $370,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  27945 Tarpon Terrace, Little Torch Key, FL 33042

  Lots of new upgrades : Remodeled* New 40 gallon Hot Water Heater, several new mini splits, New Tiled floors throughout, New kitchen, New bathroom , new cabinet in the Laundry room area lots of new shelving added throughout, New electric box on the exterior, most of the appliances kitchen and laundry are newly added upgrades completely newly painted interior. Lots of money put into this remodeled

  Anne Press Lokation Real Estate

  27945 Tarpon Terrace, Little Torch Key, FL 33042
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  $1,185,000 Sold Oct 06, 2025

  22915 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $882/SF
  • 37 Days On Market

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
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  /2

  Est $1,123,786 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft

  1981 Sugarloaf Blvd, Summerland Key, FL 33042

  1981 Sugarloaf Blvd, Summerland Key, FL 33042
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  /43

  $559,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

  Welcome to your tropical retreat! This 2-bed, 1.5-bath canal-front mobile home in Cudjoe Key offers open ocean access and the perfect blend of comfort and affordability. Located in the desirable Venture Out community, this property is also a proven income-producing vacation rental, making it a fantastic investment opportunity.Venture Out is a residential condominium community with 24-hour gated

  Justyn Ewald Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
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  /34

  $1,300,000 Sold Aug 18, 2025

  22822 John Silver Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 2002

  Last Sold Summary

  • 19% Below List Price
  • $619/SF
  • 214 Days On Market

  Current Estimated Value $1,318,826

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  22822 John Silver Ln, Summerland Key, FL 33042
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  /20

  Est $716,498 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  4244 Dorn Rd, Summerland Key, FL 33042

  4244 Dorn Rd, Summerland Key, FL 33042
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  /13

  $395,000

  • Land

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key while the building permit is in-process for a 4 bedroom / 2 bath stilted single family residence (home is additional). The plans shown are for a 1920 sq ft' / 2 story Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment,

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
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  /22

  $490,000 Sold Feb 07, 2025

  1133 Division St, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,594 Sq Ft
  • Built 1974

  Last Sold Summary

  • 18% Below List Price
  • $307/SF
  • 222 Days On Market

  Current Estimated Value $540,629

  Last Listing Agent Kaylee Moore Expert Realty LLC (HQ)

  1133 Division St, Big Pine Key, FL 33043
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  /34

  Est $739,866 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  4040 Dorn Rd, Summerland Key, FL 33042

  4040 Dorn Rd, Summerland Key, FL 33042
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  /7

  $190,000

  • Land
  • 6,000 Acres
  • $32 per Acre

  1145 Hakluyt Ln, Cudjoe Key, FL 33042

  Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

  Daniel Pacheco United Realty Group Inc

  1145 Hakluyt Ln, Cudjoe Key, FL 33042

Showing Results 641 - 680, Page 17 of 18