Summerland Key, FL Homes

• 

  

  /2

  Est $743,200

  Not Listed For Sale

  29654 Constitution Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1963

  29654 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /2

  $54,000

  $6K PRICE DROP

  • Land

  0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043
• 

  

  

  /17

  $395,000

  Sold Sep 22, 2025

  10W Cooks Unit B, Cook Island Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 596 Sq Ft
  • Built 1948

  Last Sold Summary

  • 12% Below List Price
  • $663/SF
  • 13 Days On Market

  Current Estimated Value $417,667

  Last Listing Agent Greg Gordon Island Home Realty Inc.

  10W Cooks Unit B, Cook Island Key, FL 33043
• 

  

  /2

  Est $769,682

  Not Listed For Sale

  1313 State Rd Unit 4A, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1977

  1313 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  

  /4

  $400,000

  • Land
  • 1,400 Acres
  • $286 per Acre

  27378 Jamaica Ln, Summerland Key, FL 33042

  ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

  Patricia Borges Borges Realty Group LLC

  27378 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /54

  $915,000

  Sold Aug 19, 2025

  29737 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $866/SF
  • 33 Days On Market

  Current Estimated Value $924,167

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  29737 Newfound Blvd, Big Pine Key, FL 33043
• 

  

  /37

  Est $1,690,931

  Not Listed For Sale

  2256 Matthews Rd, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2024

  2256 Matthews Rd, Big Pine Key, FL 33043

  Last Sold Summary

  • 5 Days On Market
• 

  

  /6

  $32,000

  $17K PRICE DROP

  • Land
  • 4,791 Sq Ft
  • $290,909 per Acre

  10 5th Ave, Big Pine Key, FL 33043

  1 ACRE LOT IN Big Pine Key, LOCATED JUST SOUTH OF U.S. Route 1 – PEACEFUL, NATURAL SURROUNDINGS – RARE OPPORTUNITY.BEST PRICE ON THE MARKET! EXCELLENT LONG-TERM INVESTMENT! DON’T MISS THIS OPPORTUNITY!

  Mason Gascot Knowledge Base Real Estate

  10 5th Ave, Big Pine Key, FL 33043
• 

  

  /60

  $2,512,500

  Sold Oct 31, 2025

  1260 Sugarloaf Blvd, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Below List Price
  • $871/SF
  • 60 Days On Market

  Current Estimated Value $2,537,654

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /51

  $1,250,000

  • 1 Bed
  • 3 Baths
  • 1,234 Sq Ft

  27001 Overseas Hwy, Ramrod Key, FL 33042

  Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample

  Bobby Coe RE/MAX Keys Connection (KW)

  27001 Overseas Hwy, Ramrod Key, FL 33042
• 

  

  /29

  $495,000

  Sold Feb 13, 2026

  31525 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $387/SF
  • 229 Days On Market

  Current Estimated Value $537,057

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31525 Avenue A, Big Pine Key, FL 33043
• 

  

  /13

  Est $266,186

  Not Listed For Sale

  31014 Avenue E, Big Pine Key, FL 33043

  • 1 Bed
  • Built 1969

  31014 Avenue E, Big Pine Key, FL 33043

  Last Sold Summary

  • 103 Days On Market
• 

  

  /17

  $255,000

  $10K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,100,000 per Acre

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
• 

  

  /61

  $1,900,000

  Sold Jun 15, 2026

  556 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • Built 1974

  Last Sold Summary

  • 30% Below List Price
  • $877/SF
  • 155 Days On Market

  Current Estimated Value $2,192,662

  Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /4

  Est $265,658

  Not Listed For Sale

  31373 Avenue C, Big Pine Key, FL 33043

  • 2 Beds
  • Built 1971

  31373 Avenue C, Big Pine Key, FL 33043

  Last Sold Summary

  • 116 Days On Market
• 

  

  /21

  $550,800

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  96 John St Unit 2, Summerland Key, FL 33042

  Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living space in a small, well-kept community in Summerland Key. This home is in excellent condition, offers ample parking, and provides a wonderful opportunity for affordable homeownership in the Lower Keys. Subject to affordable housing deed restrictions.

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  96 John St Unit 2, Summerland Key, FL 33042
• 

  

  /25

  $1,249,000

  Sold Apr 28, 2026

  17170 Amberjack Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  Last Sold Summary

  • $1,183/SF
  • 0 Days On Market

  Current Estimated Value $1,242,727

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17170 Amberjack Ln, Summerland Key, FL 33042
• 

  

  /28

  Est $1,831,081

  Not Listed For Sale

  27385 St Lucie Ln, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft
  • Built 1987

  27385 St Lucie Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 0 Days On Market
• 

  

  /26

  $989,000

  • 3 Beds
  • 2 Baths
  • 1,329 Sq Ft

  673 Indies Rd, Summerland Key, FL 33042

  Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. Situated on a quiet street within Breezeswept Beach Estates, this well-maintained 3-bedroom, 2-bathroom stilt home perfectly balances premier boating access with a peaceful, scenic setting. The property's positioning is truly

  Gregory Sullivan BYOWNER.COM

  673 Indies Rd, Summerland Key, FL 33042
• 

  

  /51

  $975,000

  Sold Aug 01, 2025

  527 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2023

  Last Sold Summary

  • 17% Below List Price
  • $812/SF
  • 101 Days On Market

  Current Estimated Value $1,083,583

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  527 Heck Ave, Little Torch Key, FL 33042
• 

  /2

  Not Listed For Sale

  31119 Avenue I, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft
  • Built 1961

  31119 Avenue I, Big Pine Key, FL 33043
• 

  

  /58

  $269,000

  $26K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 316 Sq Ft

  701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

  $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
• 

  

  /34

  $740,000

  Sold Jul 10, 2026

  3672 Fox St, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 1,224 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $605/SF
  • 136 Days On Market

  Current Estimated Value $810,400

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  3672 Fox St, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  29527 Constitution Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1982

  29527 Constitution Ave, Big Pine Key, FL 33043
• 

  

  /45

  $7,000,000

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

  0 Melody Key Unit 616249, Summerland Key, FL 33042

  An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

  Scott Forman Royal Palms Realty (KW)

  0 Melody Key Unit 616249, Summerland Key, FL 33042
• 

  

  /44

  $1,550,000

  Sold Feb 27, 2026

  17094 Coral Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $776/SF
  • 265 Days On Market

  Current Estimated Value $1,573,261

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17094 Coral Dr, Summerland Key, FL 33042
• 

  

  /31

  Est $800,147

  Not Listed For Sale

  27373 Antigua Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2016

  27373 Antigua Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /46

  $2,200,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1330 Sugarloaf Blvd, Summerland Key, FL 33042

  A quiet escape with million-dollar views. Situated on an expansive lot of over a quarter-acre, this three-bedroom, two-bathroom home is nestled within the sought-after shores of Sugarloaf Key--tucked away from the highway and just steps from scenic walking and bike paths. The interiors offer a crisp, modern take on coastal comfort, sold fully furnished with a curated collection of new decor and

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1330 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /49

  $278,000

  Sold Apr 30, 2026

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft
  • Built 1986

  Last Sold Summary

  • 16% Below List Price
  • $377/SF
  • 149 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
• 

  

  /9

  Est $352,977

  Not Listed For Sale

  31456 Ave F, Big Pine Key, FL 33043

  • 2 Beds
  • Built 1972

  31456 Ave F, Big Pine Key, FL 33043

  Last Sold Summary

  • 20 Days On Market
• 

  

  /46

  $675,000

  $60K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  30920 Baileys Ln, Big Pine Key, FL 33043

  Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water--just minutes to both the Gulf and the Atlantic. Situated on a spacious double lot, the property includes a 30 ft. Step down boat slip cut in, ideal for docking your boat and enjoying effortless days on the water.Designed for seamless indoor-outdoor living, the home

  Deni Heintzelman KeyIsle Realty

  30920 Baileys Ln, Big Pine Key, FL 33043
• 

  

  /40

  $950,000

  Sold Sep 17, 2025

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $825/SF
  • 85 Days On Market

  Current Estimated Value $1,035,053

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
• 

  /2

  Est $870,902

  Not Listed For Sale

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2016

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
• 

  

  /14

  $395,000

  • Land
  • 6,098 Sq Ft
  • $2,821,429 per Acre

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
• 

  

  /53

  $2,725,000

  Sold Mar 11, 2026

  1147 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $1,324/SF
  • 103 Days On Market

  Current Estimated Value $2,671,280

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1147 Flagship Dr, Summerland Key, FL 33042
• 

  /2

  Est $805,708

  Not Listed For Sale

  27087 Angelfish Rd, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2020

  27087 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 145 Days On Market
• 

  

  /3

  $284,999

  $104K PRICE DROP

  • Land
  • 23,958 Sq Ft
  • $518,180 per Acre

  00200670-000100 Sunset Blvd, Summerland Key, FL 33042

  Beautiful .55 acre lot in Summerland Key, FL. Summerland Key is a unique fly-in community with a private airstrip and marina close by. SUMMERLAND ESTATES SUMMERLAND KEY PB2-167 PT LT 25 (LOT A 90 FT X 264.75 FT). Buyer is responsible for conducting due diligence on the property prior to purchase.

  Sean Seward Keller Williams Island Life RE

  00200670-000100 Sunset Blvd, Summerland Key, FL 33042
• 

  /2

  $185,000

  Sold Mar 20, 2026

  1223 Rogers Ln, Cudjoe Key, FL 33042

  • Land
  • 6,969 Sq Ft
  • $1,156,250 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $254,155

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  1223 Rogers Ln, Cudjoe Key, FL 33042
• 

  

  /69

  Not Listed For Sale

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Built 1988

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  Last Sold Summary

  • 461 Days On Market

Showing Results 281 - 320, Page 8 of 18