Sugarloaf Key, FL Homes

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  $3,999,999

  • 5 Beds
  • 5 Baths
  • 3,700 Sq Ft

  17229 Oleander Ln, Summerland Key, FL 33042

  Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home

  Justyn Ewald Expert Realty LLC (HQ)

  17229 Oleander Ln, Summerland Key, FL 33042
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  /52

  $1,650,000 Sold Jan 28, 2026

  17213 Starfish Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1993

  Last Sold Summary

  • 15% Below List Price
  • $943/SF
  • 111 Days On Market

  Last Listing Agent The Spottswood Team Truman & Co. (KW)

  17213 Starfish Ln E, Summerland Key, FL 33042
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  /2

  Est $996,766 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  152 Sugarloaf Dr, Summerland Key, FL 33042

  152 Sugarloaf Dr, Summerland Key, FL 33042
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  /36

  $799,000

  • Land

  2950 Overseas Hwy Unit 36, Key West, FL 33040

  Welcome to the epitome of luxury RV living at the Bluewater Luxury RV Resort, where the Tropical Luxury RV lot 36 offers a prime deeded piece of real estate designed to offer discerning travelers a luxurious and comfortable stay amidst a tropical oasis.This spacious and well-appointed lot provides an ideal setting for an RV or motorhome, with premium amenities and services to cater to the needs

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 36, Key West, FL 33040
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  /4

  $175,000 Sold Dec 23, 2025

  Lot 2 Overseas Hwy, Summerland Key, FL 33042

  • Land

  Last Sold Summary

  • 15% Below List Price
  • 25 Days On Market

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 2 Overseas Hwy, Summerland Key, FL 33042
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  /30

  Est $657,405 Not Listed For Sale

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

  19506 Seminole St, Summerland Key, FL 33042

  19506 Seminole St, Summerland Key, FL 33042
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  /10

  $725,000

  • Land

  17220 Angelfish Ln, Sugarloaf Shores, FL 33042

  Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the

  The Spottswood Team Truman & Co. (KW)

  17220 Angelfish Ln, Sugarloaf Shores, FL 33042
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  /67

  $1,900,000 Sold Nov 06, 2025

  17077 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $792/SF
  • 87 Days On Market

  Current Estimated Value $1,881,081

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

  17077 Bonita Ln W, Summerland Key, FL 33042
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  /15

  Est $787,368 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,134 Sq Ft

  16991 Shore Dr, Summerland Key, FL 33042

  16991 Shore Dr, Summerland Key, FL 33042
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  /51

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  56 Bay Dr, Saddlebunch, FL

  Island Life, unequalled waterfront sunsets, ocean breezes and crystal clear waters. And you can drive to your Caribbean Island Escape! This location is exceptional on all fronts, more than 2X the avg lot size, a craftsman remodeled 3/2 converted to a 2/2 with a spacious convertible home office, gorgeous high quality materials throughout, including Walnut Engineered Flooring, Brazilian Quartzite

  Stephanie Wise Keller Williams Key West Compass Realty

  56 Bay Dr, Saddlebunch, FL
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  /59

  $2,175,000 Sold Jun 20, 2025

  17346 Keystone Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft
  • Built 2019

  Last Sold Summary

  • 13% Below List Price
  • $992/SF
  • 41 Days On Market

  Current Estimated Value $2,201,762

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  17346 Keystone Rd, Summerland Key, FL 33042
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  /21

  Est $756,186 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  19570 Mayan St, Summerland Key, FL 33042

  19570 Mayan St, Summerland Key, FL 33042
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  /49

  $910,000

  • 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 Douglas Elliman Florida, LLC - Sunset Drive

  813 Hawksbill Ln, Summerland Key, FL 33042
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  /82

  $1,800,000 Sold Jun 20, 2025

  17175 Allamanda Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $851/SF
  • 19 Days On Market

  Current Estimated Value $1,843,462

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17175 Allamanda Dr W, Summerland Key, FL 33042
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  /73

  Est $1,042,046 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  103 Shore Dr, Summerland Key, FL 33042

  103 Shore Dr, Summerland Key, FL 33042
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  /29

  $825,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  17245 Jamaica Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life--paddleboarding, kayaking, the iconic jumping bridge, and world-class cycling right out your door. Set on a generous lot, this elevated 3-bedroom, 2-bath home blends laid-back island charm with modern

  Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
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  /45

  $1,249,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  17144 Coral Dr, Summerland Key, FL 33042

  Located in prestigious Sugarloaf Shores, a coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3-bedroom, 2-bath home, a massive Great Room with a cathedral ceiling will greet you, highlighted by remodeled cabinetry, kitchen, and stainless steel appliances, including a gas range, where friends and family can gather. Enjoy the full-length porch

  Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  17144 Coral Dr, Summerland Key, FL 33042
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  /29

  Est $1,772,849 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  17234 Green Turtle Ln E, Summerland Key, FL 33042
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  /94

  $3,500,000

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe.Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and

  Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
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  /67

  $3,550,000 Sold Jun 12, 2025

  9 Bay Dr, Key West, FL 33040

  • 5 Beds
  • 5 Baths
  • 3,272 Sq Ft
  • Built 2014

  Last Sold Summary

  • 16% Below List Price
  • $1,085/SF
  • 68 Days On Market

  Current Estimated Value $3,498,269

  Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

  9 Bay Dr, Key West, FL 33040
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  /2

  Est $1,255,761 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  19563 Canal Dr, Summerland Key, FL 33042

  19563 Canal Dr, Summerland Key, FL 33042
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  /69

  $1,299,000 Under Contract

  • Land

  2950 Overseas Hwy Unit 38, Key West, FL 33040

  Discover the ultimate in luxury RV living at **Lot 38 in BWK Luxury RV Resort**--a rare double lot that redefines tropical elegance.Welcome to your private island-inspired haven, where comfort and sophistication blend seamlessly in one of the Florida Keys' most exclusive gated communities. Every inch of this high-end retreat has been thoughtfully designed with impeccable craftsmanship and

  Oleksandr Khiznichenko Keller Williams Key West Compass Realty

  2950 Overseas Hwy Unit 38, Key West, FL 33040
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  /55

  $935,000 Sold Jan 20, 2026

  146 Sugarloaf Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,859 Sq Ft
  • Built 1995

  Last Sold Summary

  • $503/SF
  • 0 Days On Market

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

  146 Sugarloaf Dr, Summerland Key, FL 33042
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  /2

  Est $739,479 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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  /4

  $100,000

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042

  Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
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  /64

  $1,302,500 Sold Aug 13, 2025

  46 Blue Water Dr, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $754/SF
  • 178 Days On Market

  Current Estimated Value $1,332,070

  Last Listing Agent Emily Lombard Ocean Sotheby's International Realty

  46 Blue Water Dr, Key West, FL 33040
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  /45

  Est $1,822,827 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

  $1,200,000

  • 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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  /48

  $1,400,000 Sold Jan 14, 2026

  17166 Wahoo Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $810/SF
  • 172 Days On Market

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

  17166 Wahoo Ln W, Summerland Key, FL 33042
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  /2

  Est $1,091,283 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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  /3

  $849,000

  • Land
  • 10 Acres
  • $84,900 per Acre

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
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  /8

  Est $710,942 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  19514 Canal Dr, Summerland Key, FL 33042

  19514 Canal Dr, Summerland Key, FL 33042
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  /54

  $915,000

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft

  17326 Jamaica Ln, Summerland Key, FL 33042

  Welcome to your slice of Lower Keys paradise--just 17 miles from Key West yet worlds away from the hustle. This elevated 2-bedroom, 2-bath home sits on a generous lot in a fantastic neighborhood, offering the perfect blend of comfort, style, and island living.Inside, vaulted ceilings and impact windows fill the home with natural light and breezy tropical charm. An elevator makes access

  Stephanie Wise Keller Williams Key West Compass Realty

  17326 Jamaica Ln, Summerland Key, FL 33042
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  /26

  Est $464,932 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  19910 Flamingo Rd, Summerland Key, FL 33042

  19910 Flamingo Rd, Summerland Key, FL 33042
• 

  

  /25

  $730,000

  • 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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  /26

  Est $1,277,719 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  105 S Point Dr, Summerland Key, FL 33042

  105 S Point Dr, Summerland Key, FL 33042
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  /116

  $19,750,000

  • 6 Beds
  • 7 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

  Lisa Swanson The Agency Florida Keys

  15760 Old State Road 4a, Summerland Key, FL 33042
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  /32

  Est $1,898,939 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft

  127 Cedar Ln, Summerland Key, FL 33042

  127 Cedar Ln, Summerland Key, FL 33042
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  /19

  $675,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  14 Coral Dr, Key West, FL 33040

  Includes an oceanview from the primary suite, this 2 Bedroom 2 Bathroom offers 2 elevated levels, vaulted ceilings, impact doors/windows, metal roof, and a downstairs enclosure for all your toys, tools, or equipment. Perfect for entertaining or a peaceful retreat, the lush tropical landscaping adds privacy to your outdoor space. Whether you're looking for a full-time residence, a vacation rental,

  Christopher Scott,PA Expert Realty LLC (HQ)

  14 Coral Dr, Key West, FL 33040
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  /2

  Est $1,588,130 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,810 Sq Ft

  17150 La Brisa Ct, Summerland Key, FL 33042

  17150 La Brisa Ct, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18