Summerland Key, FL Homes

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  /43

  $1,175,000

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,368 Sq Ft

  27395 Saint Lucie Ln, Summerland Key, FL 33042

  Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek Silestone countertops, and warm

  

  Michelle Vanhoose

  Coldwell Banker Schmitt Real Estate Co.

  27395 Saint Lucie Ln, Summerland Key, FL 33042
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  /64

  $809,000

  Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

  Current Estimated Value $828,832

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  3714 Pine St, Big Pine Key, FL 33043
• 

  

  /2

  Est $3,147,413

  Not Listed For Sale

  999 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft
  • Built 2024

  999 Flagship Dr, Summerland Key, FL 33042
• 

  

  

  /27

  $1,055,000

  $110K PRICE DROP

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

  29051 Magnolia Ln, Big Pine Key, FL 33043

  Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers an exceptional opportunity to enjoy the relaxed Lower Florida Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with

  

  Yvette Toledo-Baste

  COMPASS FLORIDA LLC

  29051 Magnolia Ln, Big Pine Key, FL 33043
• 

  

  

  /91

  $3,675,000

  Sold May 11, 2026

  493 Coral Ave, Ramrod Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $2,127/SF
  • 10 Days On Market

  Current Estimated Value $3,640,391

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  493 Coral Ave, Ramrod Key, FL 33042
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  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • 66 Days On Market
• 

  

  /50

  $1,385,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  30830 Palm Dr, Big Pine Key, FL 33043

  Discover the perfect Florida Keys waterfront retreat in Big Pine Key. Situated on an oversized 16,779 sq ft lot on a quiet street away from the highway, this solidly built concrete block home with a concrete subfloor and stucco finish offers durability, privacy, and the laid-back island lifestyle buyers dream about.Boaters will appreciate 112 feet of concrete seawall, a 10,000 lb boat lift,

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  30830 Palm Dr, Big Pine Key, FL 33043
• 

  

  /8

  $340,000

  Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 12,500 Sq Ft
  • $1,184,832 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
• 

  /2

  Est $1,251,467

  Not Listed For Sale

  29565 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2019

  29565 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /22

  $685,000

  $29K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  4039 Egret Ln, Summerland Key, FL 33042

  Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

  

  Sandra Tuttle

  Island Welcome Real Estate

  4039 Egret Ln, Summerland Key, FL 33042
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  /52

  $1,530,000

  Sold Jan 16, 2026

  1370 Long Beach Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,181 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $1,296/SF
  • 33 Days On Market

  Current Estimated Value $1,547,113

  Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

  1370 Long Beach Dr, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043
• 

  

  /46

  $795,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  29034 Rose Dr, Big Pine Key, FL 33043

  Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is

  

  Ryan Gernaat

  Coldwell Banker Schmitt Lower Keys (KW)

  29034 Rose Dr, Big Pine Key, FL 33043
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  /32

  $575,000

  Sold Jul 07, 2026

  29961 Pine Channel Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $676/SF
  • 100 Days On Market

  Current Estimated Value $588,068

  Last Listing Agent Terrance Sullivan Ocean Sotheby's International Realty

  29961 Pine Channel Rd, Big Pine Key, FL 33043
• 

  /2

  Est $860,870

  Not Listed For Sale

  18954 Acosta Trail, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2013

  18954 Acosta Trail, Summerland Key, FL 33042
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  /43

  $1,799,000

  • 3 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  51 Sawyer Dr, Cudjoe Key, FL 33042

  Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  51 Sawyer Dr, Cudjoe Key, FL 33042
• 

  

  /21

  $775,000

  Sold Mar 23, 2026

  27360 Saint Croix Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $673/SF
  • 272 Days On Market

  Current Estimated Value $795,894

  Last Listing Agent Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
• 

  /2

  Est $557,076

  Not Listed For Sale

  520 Blackbeard Rd, Little Torch Key, FL 33042

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042
• 

  

  /73

  $2,849,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  17041 Marlin Dr, Sugarloaf Key, FL 33042

  Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  17041 Marlin Dr, Sugarloaf Key, FL 33042
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  /58

  $760,000

  Sold Aug 19, 2025

  640 Carolyn Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $896/SF
  • 66 Days On Market

  Current Estimated Value $772,279

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
• 

  

  /47

  $649,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

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

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
• 

  

  /14

  $205,000

  Sold May 20, 2026

  701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

  • Land
  • 1,742 Sq Ft
  • $5,125,000 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 56 Days On Market

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
• 

  /2

  Est $924,912

  Not Listed For Sale

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2022

  27434 Saint Lucie Ln, Ramrod Key, FL 33042
• 

  

  /22

  $899,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft

  23940 Overseas Hwy, Summerland Key, FL 33042

  Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating,

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  23940 Overseas Hwy, Summerland Key, FL 33042
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  /43

  $1,700,000

  Sold Jan 30, 2026

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $820/SF
  • 140 Days On Market

  Current Estimated Value $1,712,484

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
• 

  /2

  Est $2,306,292

  Not Listed For Sale

  305 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft
  • Built 1986

  305 S Point Dr, Summerland Key, FL 33042
• 

  

  /36

  $949,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft

  273 Indies Rd, Summerland Key, FL 33042

  Welcome to this bright and modern 2-bedroom, 2-bath home located in the desirable Breezeswept Beach Estates on Ramrod Key. Completed in 2024 by the builder with high-quality features including a metal roof, impact windows, new A/C, and durable Hardi board siding. This home was later purchased and further upgraded by the current owner, who is also the first to live in the home. Since purchasing,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  273 Indies Rd, Summerland Key, FL 33042
• 

  

  /44

  $700,000

  Sold Jan 09, 2026

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $810/SF
  • 23 Days On Market

  Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
• 

  

  /23

  Not Listed For Sale

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 8 Days On Market
• 

  

  /50

  $2,300,000

  New Construction

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

  30995 Watson Blvd, Big Pine Key, FL 33043

  Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, metal roof, stainless steel appliances, quartz countertops, open-concept living, screened porch, private pool, and covered parking below. Built for coastal living, the CBS structure, impact openings, elevated design,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real E

  30995 Watson Blvd, Big Pine Key, FL 33043
• 

  

  /57

  $1,250,000

  Sold Jun 30, 2026

  25368 2nd St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1958

  Last Sold Summary

  • 24% Below List Price
  • $898/SF
  • 241 Days On Market

  Current Estimated Value $1,513,000

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, FL 33042
• 

  /2

  Est $495,000

  Not Listed For Sale

  0 E Ave Unit 604969, Big Pine Key, FL 33043

  • Studio

  0 E Ave Unit 604969, Big Pine Key, FL 33043
• 

  

  /59

  $649,000

  New Construction $5K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate- Venture

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

  

  /43

  $990,000

  Sold Dec 10, 2025

  29839 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Below List Price
  • $566/SF
  • 4 Days On Market

  Current Estimated Value $1,044,713

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  29839 Newfound Blvd, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  0 Crane Blvd, Sugarloaf Key, FL 33042

  0 Crane Blvd, Sugarloaf Key, FL 33042
• 

  

  /29

  $775,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft

  28452 Yucatan Ln, Summerland Key, FL 33042

  Must be sold after Jan 1, 2027. Canal front home with quick exit out of the canal to Pine Channel for Atlantic or Gulf access. 7200 sq.ft. lot. Back yard big enough for a pool. Pack your toothbrush and your ready for your salt life to begin. Being sold mostly furnished 2bd/2bth 1162 sq.ft. Home, plus, southerly facing screen porch, which has accordian shutters,porch faces back yard and canal.

  Rose Dell Keller Williams Key West Compass Realty

  28452 Yucatan Ln, Summerland Key, FL 33042
• 

  

  /88

  $3,475,000

  Sold May 19, 2026

  680 Elma Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 3.5 Baths
  • 2,050 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Below List Price
  • $1,695/SF
  • 140 Days On Market

  Current Estimated Value $3,124,982

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  680 Elma Ave, Big Pine Key, FL 33043
• 

  /2

  Est $477,031

  Not Listed For Sale

  390 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1958

  390 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /21

  $430,000

  $35K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 799 Sq Ft

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

  A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

  Rose Dell Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

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