Summerland Key, FL Homes

• 

  

  

  /64

  Est $1,169,433

  Not Listed For Sale

  184 Cutthroat Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1963

  184 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 151 Days On Market

  Last Listing Agent Beata Sharpe Coldwell Banker Schmitt Real Estate Co.
• 

  

  

  /33

  $249,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room.The property is currently occupied by a long-term

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  

  

  /32

  $970,000

  Sold Jul 08, 2026

  17287 Cayman Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Below List Price
  • $652/SF
  • 42 Days On Market

  Current Estimated Value $1,042,746

  Last Listing Agent Jonathan Minerick Homecoin.com

  17287 Cayman Dr, Summerland Key, FL 33042
• 

  

  

  /58

  Est $1,652,364

  Not Listed For Sale

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  

  

  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
• 

  /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 $2,180,077

  Last Listing Agent Scott Brisson KeyIsle Realty

  743 E Shore Dr, Summerland Key, FL 33042
• 

  

  /4

  Est $871,864

  Not Listed For Sale

  27456 Martinique Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,108 Sq Ft
  • Built 1976

  27456 Martinique Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.
• 

  

  /9

  $514,900

  • Land
  • 2,613 Sq Ft
  • $8,581,667 per Acre

  701 Spanish Main Dr Unit LOT 266, Cudjoe Key, FL 33042

  Premier Waterfront RV Lot in Venture Out | 35' Seawall, Ocean Views & Proven Rental Income!Whether you are looking for your own personal Florida Keys getaway or a high-performing investment property, this lot offers the perfect blend of luxury, location, and lucrative returns. Boasting a consistent rental history, this turn-key property is a proven income producer with established guest

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit LOT 266, Cudjoe Key, FL 33042
• 

  

  /11

  $475,000

  Sold May 27, 2026

  19264 Acosta Trail, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 832 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $571/SF
  • 9 Days On Market

  Current Estimated Value $441,960

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  19264 Acosta Trail, Summerland Key, FL 33042
• 

  

  /45

  Est $1,978,522

  Not Listed For Sale

  19527 Indian Mound Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,752 Sq Ft
  • Built 1996

  19527 Indian Mound Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 96 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /41

  $849,000

  $120K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,277 Sq Ft

  29544 Independence Ave, Big Pine Key, FL 33043

  GREAT INVESTMENT OPPORTUNITY! $849,000 Best price property in Pine Channel Estates, Big Pine Key. Fully furnished. Remodeled 2 bdrm/2 full bath + BONUS room (3rd bdrm/office). 75' Canal frontage. Total sq.ft. 1934 w/heated sq.ft. 1277. All new SS appliances. Metal roof, impact windows and garage door, vinyl siding, tankless water heater, gutters, hurricane shutters, fence, covered patio, large

  Jennifer Sylvia Keller Williams Key West Compass Realty

  29544 Independence Ave, Big Pine Key, FL 33043
• 

  

  /4

  $700,000

  Sold Apr 23, 2026

  20963 7th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $450/SF

  Current Estimated Value $862,829

  Last Listing Agent Wyelda Bierman Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  20963 7th Ave W, Summerland Key, FL 33042
• 

  

  /61

  Est $1,723,363

  Not Listed For Sale

  227 La Fitte Rd, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,260 Sq Ft
  • Built 1982

  227 La Fitte Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Jennifer Chaney Chaney Homes
• 

  

  /71

  $2,069,000

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft

  1733 Sunrise Dr, Big Pine Key, FL 33043

  Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

  Norman De la Cruz Florida Realty of Miami Corp

  1733 Sunrise Dr, Big Pine Key, FL 33043
• 

  

  /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

  Current Estimated Value $1,037,095

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  29462 Geraldine St, Big Pine Key, FL 33043
• 

  

  /20

  Est $1,690,500

  Not Listed For Sale

  4244 Dorn Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1984

  4244 Dorn Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 368 Days On Market

  Last Listing Agent Thomas Gomez Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  /54

  $4,375,000

  New Construction $100K PRICE INCREASE Pending

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 4, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 4, Summerland Key, FL 33042
• 

  

  /42

  $925,000

  Sold May 29, 2026

  29664 Saratoga Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 2,129 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $434/SF
  • 46 Days On Market

  Current Estimated Value $973,521

  Last Listing Agent Halley Haack Coldwell Banker Schmitt RE Co.

  29664 Saratoga Ave, Big Pine Key, FL 33043
• 

  

  /56

  Est $2,323,340

  Not Listed For Sale

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 1975

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.
• 

  

  /47

  $1,200,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  637 Caribbean Dr E, Summerland Key, FL 33042

  Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromatic palette, the interiors feel fresh, cohesive, and effortlessly sophisticated--ready for you to start living the Keys lifestyle. Step outside to a relaxing porch overlooking a 60' wide, crystal-clear flow-through canal--perfect

  Donna Pezzi Keller Williams Key West Compass Realty

  637 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /39

  $1,300,000

  Sold Jun 05, 2026

  20838 5th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1987

  Last Sold Summary

  • 19% Below List Price
  • $669/SF
  • 187 Days On Market

  Current Estimated Value $1,363,565

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20838 5th Ave W, Cudjoe Key, FL 33042
• 

  

  /52

  Est $1,320,711

  Not Listed For Sale

  570 La Fitte Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 2020

  570 La Fitte Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 126 Days On Market

  Last Listing Agent John L. Markle Keller Williams Realty Premier Properties - Kendall
• 

  

  /15

  $895,000

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

  135 Tortuga Ln, Summerland Key, FL 33042

  If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and

  Kathleen Reed Bruno Realty Group, Inc

  135 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /32

  $670,000

  Sold Jun 15, 2026

  27999 Lobster Tail Trail, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $570/SF
  • 148 Days On Market

  Current Estimated Value $687,008

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  27999 Lobster Tail Trail, Little Torch Key, FL 33042
• 

  

  /47

  Est $2,867,747

  Not Listed For Sale

  27440 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,958 Sq Ft
  • Built 1982

  27440 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Thomas Mack SBX Real Estate, LLC (KW)
• 

  

  /19

  $799,000

  $51K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  3922 Gordon Rd, Big Pine Key, FL 33043

  Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordon Road is an elevated 2BR/2BA waterfront retreat in Big Pine Key offering the lifestyle buyers come here for--easy boating, inviting outdoor living, and a home that feels like an escape from the moment you arrive. Bright coastal interiors, an open living/dining/kitchen layout, and a screened porch create a

  Dominic Paolillo Jr. Truman & Co. (KW)

  3922 Gordon Rd, Big Pine Key, FL 33043
• 

  

  /18

  $415,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  • Land
  • 2,178 Sq Ft
  • $8,300,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 228 Days On Market

  Current Estimated Value $436,063

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
• 

  

  /46

  Est $2,672,010

  Not Listed For Sale

  961 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,006 Sq Ft
  • Built 1998

  961 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Sandra Tuttle American Caribbean Real Estate Lower Keys
• 

  

  /64

  $1,800,000

  $190K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  3127 Stewart Rd, Summerland Key, FL 33042

  Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

  Pamela Stangler Expert Realty LLC

  3127 Stewart Rd, Summerland Key, FL 33042
• 

  

  /62

  $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

  Current Estimated Value $1,184,534

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /40

  Est $1,095,528

  Not Listed For Sale

  791 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1982

  791 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 191 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /34

  $1,549,000

  New Construction

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  27374 Guadaloupe Ln, Summerland Key, FL 33042

  *Construction process underway. Expected completion November/December 2026Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27374 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /42

  $749,000

  Sold Sep 19, 2025

  28009 Gulf Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $743/SF
  • 88 Days On Market

  Current Estimated Value $742,875

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  28009 Gulf Blvd, Big Pine Key, FL 33043
• 

  

  /28

  Est $826,993

  Not Listed For Sale

  27378 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 925 Sq Ft
  • Built 1963

  27378 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)
• 

  

  /4

  $2,499,000

  $251K PRICE DROP

  • 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
• 

  /2

  $55,000

  Sold Dec 04, 2025

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $399,300 per Acre

  Last Sold Summary

  • 90% Above List Price
  • 73 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
• 

  

  /18

  Est $760,366

  Not Listed For Sale

  27438 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1987

  27438 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 146 Days On Market

  Last Listing Agent Caroline Bauer Key West Sales, LLC
• 

  

  /31

  $998,000

  $57K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  83 Sugarloaf Dr, Summerland Key, FL 33042

  Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  83 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /50

  $1,334,000

  Sold Aug 03, 2026

  29524 Flying Cloud Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $897/SF
  • 69 Days On Market

  Current Estimated Value $1,371,328

  Last Listing Agent Kenneth Herzbrun Formula Realty

  29524 Flying Cloud Ave, Big Pine Key, FL 33043
• 

  

  /23

  Est $649,460

  Not Listed For Sale

  27390 Barbados Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1982

  27390 Barbados Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 176 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

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