Summerland Key, FL Homes

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  $699,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  31134 Hollerich Dr, Big Pine Key, FL 33043

  Motivated Seller, turn key, including boat!Don't Miss This Waterfront Opportunity in Big Pine Key! Enjoy the ultimate Florida Keys lifestyle in this spacious 3-bedroom, 2-bath home featuring terrazzo floors, impact-rated doors and windows, and a screened porch overlooking the canal. Boaters and anglers will love the 90-foot concrete, step down seawall, davits and easy access to Bogie Channel --

  

  Jennifer Weeks

  Select Properties of NWFL

  (866) 378-6961

  31134 Hollerich Dr, Big Pine Key, FL 33043
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  /17

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • House for Rent

  30612 23rd Ln, Big Pine Key, FL 33043

  Property Id: 2240886Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy,

  30612 23rd Ln, Big Pine Key, FL 33043
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  $699,000 Sold Mar 27, 2025

  29162 Camellia Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft
  • Built 1990

  Last Sold Summary

  • $574/SF
  • 11 Days On Market

  Current Estimated Value $699,357

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

  29162 Camellia Ln, Big Pine Key, FL 33043
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  /21

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
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  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 Spain Blvd, Summerland Key, FL 33042

  Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 882-7957

  21855 Spain Blvd, Summerland Key, FL 33042
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  $4,500 per month

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • House for Rent

  27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042

  House in the Lower Keys Seasonal Rental. Available Sept 15, 2025 – Villa Marquesa, Lower Keys waterfront retreat! Spacious furnished home ideal for families, multi-gen living, or work-from-paradise. Corner lot on 2 wide canals with deep water access & 2 private docks (45’ & 15’). Upstairs: 3BR/1BA, 1,200 SQF, open kitchen, dining, living & TV rooms, water views. You can also rent downstairs unit,

  Hamlet Garcia Proxy Realty Group LLC

  27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042
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  /43

  $1,300,000 Sold Mar 14, 2025

  1050 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,171 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $1,110/SF
  • 24 Days On Market

  Current Estimated Value $1,319,141

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  1050 Gulf Dr, Summerland Key, FL 33042
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  Est $1,178,412 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042

  17165 Wahoo Ln W, Upper Sugarloaf Key, FL 33042
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  /52

  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,181 Sq Ft

  1370 Long Beach Dr, Big Pine Key, FL 33043

  Introducing an exceptionally rare offering on iconic Long Beach Drive! 1370 & 1390 Long Beach Dr. include two parcels totaling over 30,000 sq ft with 200 feet of deep, gin-clear water access and 100 feet of concrete dockage. This is one of the few locations in the Florida Keys with true Atlantic access and no bridges, providing effortless boating to Picnic Island, Little Palm Island, Looe Key

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (877) 359-6988

  1370 Long Beach Dr, Big Pine Key, FL 33043
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  /15

  $3,550 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  31430 Avenue E, Big Pine Key, FL 33043

  Property Id: 2249521Annual long-term rental, spacious 3 bedroom, 2 bath stilt home, open floor plan. Covered porch with sliding French doors from the dining area. No neighbor on one side or across the street. Interior features include tile floors, a large kitchen, plenty of cabinets and a breakfast bar, laundry closet, hall bathroom has tub, and a master bathroom has shower. Central A/C

  31430 Avenue E, Big Pine Key, FL 33043
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  /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 $508,899

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

  Unlisted Address
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  /8

  Est $242,544 Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042
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  $1,499,000

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

  823 Indies Rd, Ramrod Key, FL 33042

  Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 614-6847

  823 Indies Rd, Ramrod Key, FL 33042
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  /13

  $5,143 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28515 Channel View Dr, Little Torch Key, FL 33042

  This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour community gym and

  Joseph Danieli AKT Realty LLC

  28515 Channel View Dr, Little Torch Key, FL 33042
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  /73

  $2,925,000 Sold Jun 10, 2025

  17018 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1991

  Last Sold Summary

  • 25% Below List Price
  • $1,987/SF
  • 122 Days On Market

  Current Estimated Value $2,865,725

  Last Listing Agent Coby Taylor Taylor & Assoc. RE, Inc.

  17018 Wahoo Ln, Summerland Key, FL 33042
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  /63

  Est $4,302,823 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 4,200 Sq Ft

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042
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  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 Sawyer Dr, Summerland Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
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  /19

  $4,700 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  486 Airport Dr S, Summerland Key, FL 33042

  Property Id: 2182502Enjoy Florida Keys living in a nice neighborhood on a wide 60 ft., flow-through boating canal with a concrete seawall and davits — perfect for your boat or water toys. relax on the 400 sq. ft. screened porch, or take advantage of the massive 1,300 sqft garage/airport hangar downstairs — plenty of room to park all your toys and gear. Upstairs offers 3 bedrooms, 2 baths,

  486 Airport Dr S, Summerland Key, FL 33042
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  /15

  $165,000 Sold Feb 24, 2025

  8 Calico Jack Circle Cir, Verifying, FL 33042

  • Land

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY

  8 Calico Jack Circle Cir, Verifying, FL 33042
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  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
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  /83

  $3,900,000

  • 4 Beds
  • 3.5 Baths
  • 2,050 Sq Ft

  680 Elma Ave, Big Pine Key, FL 33043

  RARE * PRIVATE ESTATE LOT- WEST FACING-DREAMY SUNSETS -New features include ownership of surrounding Bay bottom! 600 sq ft detached garage! Tiki with outdoor kitchen!* Welcome to Tarpon Cove, an exclusive, resort-like retreat nestled on a sprawling estate lot in the heart of Big Pine Key in the Lower Florida Keys. This recently redesigned home offers a perfect blend of modern elegance and natural

  

  Sandra Tuttle

  Island Welcome Real Estate

  (877) 359-5426

  680 Elma Ave, Big Pine Key, FL 33043
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  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  3770 Park Ave, Big Pine Key, FL 33043

  Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

  Mary Jo Selden DomainRealty.com LLC

  3770 Park Ave, Big Pine Key, FL 33043
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  /8

  $906,300 Sold Apr 30, 2025

  0000 Dorn Rd, Big Torch Key, FL 33042

  • Land
  • 35.5 Acres
  • $25,530 per Acre

  Last Sold Summary

  • 43% Below List Price
  • 103 Days On Market

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  0000 Dorn Rd, Big Torch Key, FL 33042
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  Not Listed For Sale

  0000 Watson Blvd, Big Pine Key, FL 33043

  0000 Watson Blvd, Big Pine Key, FL 33043
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  /48

  $319,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

  Income-Producing Gem in Venture Out! Affordable 2BR/1BA Getaway with Resort Amenities.Discover an incredible opportunity to own a piece of the highly sought-after, gated community of Venture Out. This charming 2-bedroom, 1-bathroom home is one of the community's most affordable properties, offering a perfect blend of cozy comfort and exceptional investment potential.Ready for you to move in

  

  Ian Calderwood

  Bluescape Real Estate

  (305) 570-4554

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
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  /20

  $7,082 per month

  • 1 Bed
  • 1 Bath
  • 893 Sq Ft
  • Condo for Rent

  18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042

  Escape to paradise and feel at home in this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key, accommodating up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails.This charming home features a spacious open-concept floor plan designed for relaxation and connection. Natural light pours into the airy interior,

  18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042
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  /50

  $875,000 Sold Feb 13, 2025

  489 Pirates Rd, Little Torch Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,638 Sq Ft
  • Built 1984

  Last Sold Summary

  • 20% Below List Price
  • $534/SF
  • 38 Days On Market

  Current Estimated Value $814,339

  Last Listing Agent Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

  489 Pirates Rd, Little Torch Key, FL 33042
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  /2

  Est $268,122 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
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  /45

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  30366 Falcon Ln, Big Pine Key, FL 33043

  Fantastic CBS canal front Pool home on a double lot in Tropical Bay Estates. Entering into the large Great Room you will find soaring wood ceilings and an open floor plan boasting a true chef's Kitchen with stainless steel Viking appliances, gas range, and large granite bar to gather around. The spacious screened in Porch overlooks the water and is the perfect place to enjoy outdoor dining.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 231-9107

  30366 Falcon Ln, Big Pine Key, FL 33043
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  /23

  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • House for Rent

  74 Pelican Ln Unit 1, Big Pine Key, FL 33043

  Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all nearby

  Yunior Molina My Realty Group, LLC.

  74 Pelican Ln Unit 1, Big Pine Key, FL 33043
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  $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 $780,731

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

  29025 Geranium Dr, Big Pine Key, FL 33043
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  Est $933,344 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  28120 County Rd, Little Torch Key, FL 33042

  28120 County Rd, Little Torch Key, FL 33042
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  $1,699,000

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  17094 Coral Dr, Summerland Key, FL 33042

  This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-7125

  17094 Coral Dr, Summerland Key, FL 33042
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  /14

  $3,950 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28532 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 1/31/26.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna, marina

  Joseph Danieli AKT Realty LLC

  28532 Channel View Dr, Little Torch Key, FL 33042
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  $775,000 Sold Feb 07, 2025

  29154 Cedar Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $950/SF
  • 25 Days On Market

  Current Estimated Value $762,273

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

  29154 Cedar Dr, Big Pine Key, FL 33043
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  /2

  Est $1,094,432 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  17277 Dolphin St E, Summerland Key, FL 33042

  17277 Dolphin St E, Summerland Key, FL 33042
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  /55

  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  937 Gulf Dr, Summerland Key, FL 33042

  Step into island elegance with this beautifully remodeled 3-bedroom, 2. bath waterfront home in one of the Florida Keys' most coveted boating communities -- Summerland Key Cove. Originally built in 2008 and completely redesigned in 2024, this residence blends contemporary coastal design with the solid construction and storm-safe features that matter most.Modern Coastal Interiors:The interior

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 751-4617

  937 Gulf Dr, Summerland Key, FL 33042
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  /9

  $12,857 per month

  • 4 Beds
  • 3 Baths
  • 2,855 Sq Ft
  • House for Rent

  28502 Channel View Dr, Little Torch Key, FL 33042

  This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

  Joseph Danieli AKT Realty LLC

  28502 Channel View Dr, Little Torch Key, FL 33042
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  $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 $689,049

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo

  27317 Cayman Ln, Summerland Key, FL 33042
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  /2

  Est $1,163,772 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft

  421 W Indies, Ramrod Key, FL 33042

  421 W Indies, Ramrod Key, FL 33042

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