8,478

Summerland Key, FL Homes

Section Image Section Image
  • /43

    $1,125,000

    $125K 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

    Agent Photo

    Michelle Vanhoose

    Coldwell Banker Schmitt Real Estate Co.

    27395 Saint Lucie Ln, Summerland Key, FL 33042
  • /20

    Starting at $3,299 Per Month

    • 2 - 4 Beds

    28501 Channel View Dr, Little Torch Key, FL 33042

    In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

    Little Torch Cottages

    28501 Channel View Dr, Little Torch Key, FL 33042
  • /62

    $1,500,000

    Sold Aug 10, 2026

    22410 Jolly Roger Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,587 Sq Ft
    • Built 1982

    Last Sold Summary

    • $945/SF
    • 10 Days On Market

    Current Estimated Value $1,674,544

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    22410 Jolly Roger Dr, Summerland Key, FL 33042
    • /63

      Est $2,038,785

      Not Listed For Sale

      17057 Bonita Ln W, Sugarloaf Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,366 Sq Ft
      • Built 2015
      17057 Bonita Ln W, Sugarloaf Key, FL 33042

      Last Sold Summary

      • 190 Days On Market

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

  • /70

    $1,695,000

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    30463 Hawk Ln, Big Pine Key, FL 33043

    Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living. Outdoors, the home transforms into a

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    30463 Hawk Ln, Big Pine Key, FL 33043
  • /19

    $4,188

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    29179 Rose Dr Unit SI ID1545784P, Big Pine Key, FL 33043

    The advertised rate of $4,188/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 27, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    29179 Rose Dr Unit SI ID1545784P, Big Pine Key, FL 33043
  • /41

    $1,065,000

    Sold Jun 26, 2026

    325 Pirates Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Built 2025

    Last Sold Summary

    • 9% Below List Price
    • $807/SF
    • 148 Days On Market

    Current Estimated Value $1,075,879

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    325 Pirates Rd, Summerland Key, FL 33042
    • /29

      Not Listed For Sale

      31487 F Ave, Big Pine Key, FL 33043

      • 3 Beds
      • 2 Baths
      • 1,150 Sq Ft
      • Built 2022
      31487 F Ave, Big Pine Key, FL 33043

      Last Sold Summary

      • 188 Days On Market

      Last Listing Agent Armando Dominguez SEI Brokers Corporation

  • /65

    $2,499,000

    • 4 Beds
    • 2 Baths
    • 2,739 Sq Ft

    21023 2nd Ave, Summerland Key, FL 33042

    Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21023 2nd Ave, Summerland Key, FL 33042
  • /20

    $7,200

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Condo for Rent

    886 Loggerhead Ln Unit SI ID1297829P, Summerland Key, FL 33042

    The advertised rate of $7,200/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    886 Loggerhead Ln Unit SI ID1297829P, Summerland Key, FL 33042
  • /50

    $1,632,000

    Sold Apr 30, 2026

    29678 Constitution Ave, Big Pine Key, FL 33043

    • 3 Beds
    • 2.5 Baths
    • 2,172 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $751/SF
    • 62 Days On Market

    Current Estimated Value $1,635,619

    Last Listing Agent Callie Harris Brenda Donnelly Real Estate LLC

    29678 Constitution Ave, Big Pine Key, FL 33043
    • /5

      Est $211,897

      Not Listed For Sale

      27313 Saint Martin Ln, Ramrod Key, FL 33042

      27313 Saint Martin Ln, Ramrod Key, FL 33042

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  • /62

    $5,200,000

    • 4 Beds
    • 3.5 Baths
    • 2,660 Sq Ft

    17013 Coral Dr, Sugarloaf Key, FL 33042

    Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17013 Coral Dr, Sugarloaf Key, FL 33042
  • /18

    $3,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • House for Rent

    1635 Pandorea Ln, Big Pine Key, FL 33043

    Welcome to your ideal rental in Big Pine Key, Florida! This charming property offers a perfect environment for those seeking a peaceful lifestyle close to nature and conveniences.Key Property Features include a spacious living area designed for comfort, ensuring you have plenty of room to relax and entertain. Enjoy the benefit of central heating and air conditioning, complemented by

    1635 Pandorea Ln, Big Pine Key, FL 33043
  • /60

    $950,000

    Sold Oct 17, 2025

    76 W Shore Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,028 Sq Ft
    • Built 2001

    Last Sold Summary

    • 13% Below List Price
    • $924/SF
    • 369 Days On Market

    Current Estimated Value $942,462

    Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

    76 W Shore Dr, Summerland Key, FL 33042
    • /3

      Not Listed For Sale

      701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 488 Sq Ft
      • Built 1999
      701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  • /69

    $3,300,000

    $200K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    1083 Labat Ln, Cudjoe Key, FL 33042
  • /14

    $3,500 Per Month

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

    3693 Landers St, Big Pine Key, FL 33043

    Property Id: 2514237 Annual Canal-Front Rental on Big Pine Key! Utilities not included. This charming 2-bedroom, 2-bath home sits on a desirable corner lot with water access, offering a relaxed island lifestyle. Enjoy peaceful views. House is on a corner cana. Nice screened-in back porch with sliding doors to living and dining areas.—perfect for morning coffee or evening unwinding. Open

    3693 Landers St, Big Pine Key, FL 33043
  • /33

    $910,000

    Sold Apr 13, 2026

    151 Cutthroat Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2.5 Baths
    • 1,140 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $798/SF
    • 46 Days On Market

    Current Estimated Value $920,617

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

    151 Cutthroat Dr, Summerland Key, FL 33042
    • /22

      Est $533,877

      Not Listed For Sale

      31232 Ave d, Big Pine Key, FL 33043

      • 3 Beds
      • 1 Bath
      • 988 Sq Ft
      • Built 1958
      31232 Ave d, Big Pine Key, FL 33043

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  • /61

    $1,399,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,372 Sq Ft

    21012 6th Ave, Summerland Key, FL 33042

    Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21012 6th Ave, Summerland Key, FL 33042
  • /8

    $5,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • House for Rent

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Property Id: 1197908 Canal front pool home with a double fenced in lot. Enough room for all your boats and toys. Large saltwater pool perfect for soaking up the sun and enjoying a peaceful afternoon. The split layout provides privacy with your own separate areas to unwind. Bring your 4 legged family members. Bonus room could be the 4th bedroom or office. Large AC storage area or workshop and

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • /45

    $1,550,000

    Sold Jan 30, 2026

    28538 John Silver Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $1,242/SF
    • 164 Days On Market

    Current Estimated Value $1,532,219

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    28538 John Silver Rd, Summerland Key, FL 33042
    • /45

      Est $1,788,950

      Not Listed For Sale

      23066 Tarpon Ln, Summerland Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 1,938 Sq Ft
      • Built 2025
      23066 Tarpon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • /72

    $3,899,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,096 Sq Ft

    17015 Wahoo Ln W, Sugarloaf Key, FL 33042

    Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17015 Wahoo Ln W, Sugarloaf Key, FL 33042
  • /19

    $4,188

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    29179 Rose Dr Unit SI ID1545784P, Big Pine Key, FL 33043

    The advertised rate of $4,188/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 27, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    29179 Rose Dr Unit SI ID1545784P, Big Pine Key, FL 33043
  • /32

    $950,000

    Sold Aug 13, 2026

    1129 Hawksbill Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $826/SF
    • 3 Days On Market

    Current Estimated Value $1,014,906

    Last Listing Agent Sean Farrer Coldwell Banker Schmitt RE Co

    1129 Hawksbill Ln, Summerland Key, FL 33042
    • /26

      Est $253,545

      Not Listed For Sale

      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

      • Built 1978
      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /30

    $749,500

    $46K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,562 Sq Ft

    360 W Shore Dr, Summerland Key, FL 33042

    Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers. The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

    Agent Photo

    Brenda Thomas

    Island Welcome Real Estate

    360 W Shore Dr, Summerland Key, FL 33042
  • /21

    $3,600

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft
    • Townhouse for Rent

    594 W Shore Dr, Summerland Key, FL 33042

    Enjoy the laid-back Florida Keys lifestyle in this spacious upstairs 2-bedroom, 1-bath waterfront duplex located on beautiful Summerland Key. With approximately 1,180 square feet of living space, this home offers a comfortable, open layout in a convenient location near Key West, Big Pine Key, and Marathon.Inside, you'll find a bright open-concept living and dining area with plenty of room to

    594 W Shore Dr, Summerland Key, FL 33042
  • /45

    $630,000

    Sold Dec 08, 2025

    22970 Sharp Ln, Summerland Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 576 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Below List Price
    • $1,094/SF
    • 4 Days On Market

    Current Estimated Value $656,089

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    22970 Sharp Ln, Summerland Key, FL 33042
    • /26

      Not Listed For Sale

      27873 Coral Shores Rd, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 686 Sq Ft
      • Built 1985
      27873 Coral Shores Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 70 Days On Market

      Last Listing Agent Tracy Shields KeyIsle Realty

  • /23

    $459,000

    • Land
    • 1,742 Sq Ft
    • $11,475,000 per Acre

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your seawall!RV Lot 609 in Venture Out.Experience the epitome of waterfront Florida Keys living on this Canal Front RV Lot with 40' Seawallnestled within an exclusive gated community.This beautiful canal front property boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 40 ft seawall.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
  • /23

    $3,900

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Townhouse for Rent

    596 W Shore Dr, Summerland Key, FL 33042

    Enjoy the laid-back Florida Keys lifestyle in this spacious downstairs 3-bedroom, 2-bath waterfront duplex located on beautiful Summerland Key. With approximately 1,392 square feet of living space, this home offers a comfortable, open layout in a convenient location near Key West, Big Pine Key, and Marathon.Inside, you'll find an open-concept living and dining area with plenty of room to

    596 W Shore Dr, Summerland Key, FL 33042
  • /88

    $732,000

    Sold Apr 21, 2026

    40 Munson Ave, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Below List Price
    • $693/SF
    • 128 Days On Market

    Current Estimated Value $724,124

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    40 Munson Ave, Summerland Key, FL 33042
    • /36

      Est $962,581

      Not Listed For Sale

      3666 S Seas St, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,519 Sq Ft
      • Built 1988
      3666 S Seas St, Big Pine Key, FL 33043

      Last Sold Summary

      • 89 Days On Market

      Last Listing Agent Scott Brisson KeyIsle Realty

  • /52

    $599,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    31118 Avenue I, Big Pine Key, FL 33043

    Welcome to laid-back island living in this beautifully updated 3-bedroom, 2-bathroom home on Big Pine Key. Recent upgrades include a brand-new kitchen with stainless steel appliances, along with impact-resistant windows and doors throughout.The home also features a large downstairs enclosure offering abundant space for storage, tools, bicycles, kayaks, and other island essentials.

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    31118 Avenue I, Big Pine Key, FL 33043
  • /41

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • House for Rent

    280 Airport Dr S, Summerland Key, FL 33042

    *** Private Airstrip *** Welcome to your slice of paradise in the Florida Keys for your vacation rental! For aviation enthusiasts, the allure of this property is further enhanced by its location within a private airpark community (FD51 Summerland Key Airport). Nestled on a serene, clear wide canal with direct access to the Atlantic Ocean with no bridges, within a private airpark community, this

    Lisa Guirguis Genesis Realty Team

    280 Airport Dr S, Summerland Key, FL 33042
  • /37

    $268,000

    Sold Apr 27, 2026

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $5,360,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 52 Days On Market

    Current Estimated Value $269,729

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    • /22

      Not Listed For Sale

      133 Freedom Ln, Big Pine Key, FL 33043

      • 2 Beds
      • 1.5 Baths
      • 720 Sq Ft
      • Built 1972
      133 Freedom Ln, Big Pine Key, FL 33043

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,170,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$1,000,000
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$917
Number of Homes for Sale
52
Last 12 months Home Sales
116
Months of Supply
5.40
Median List Price
$1,269,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home