8,477

Summerland Key, FL Homes

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  • /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

    Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
  • /31

    $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
  • /60

    $930,000

    Sold Jan 23, 2026

    27405 Guadaloupe Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $722/SF
    • 51 Days On Market

    Current Estimated Value $930,560

    Last Listing Agent Mark Gable Engel & Völkers Marathon

    27405 Guadaloupe Ln, Summerland Key, FL 33042
    • /14

      Not Listed For Sale

      1639 Pine Channel Dr, Little Torch Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 6,725 Sq Ft
      • Built 1975
      1639 Pine Channel Dr, Little Torch Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  • /49

    $849,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    22832 John Silver Ln, Summerland Key, FL 33042

    CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES.Situated on over 6,000 Square Feet on a deep water canal - this recently updated property provides easy boating access to both the Gulf and the Atlantic, making it a perfect home base for world class fishing, diving, SANDBARS and enjoying the keys lifestyle.New Upgrades Include -Fully remodeled

    Agent Photo

    Mike Kane

    Internet Realty of the Florida Keys

    22832 John Silver Ln, Summerland Key, FL 33042
  • /81

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,443 Sq Ft
    • House for Rent

    441 La Fitte Rd, Summerland Key, FL 33042

    ** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in

    Carolina Gil Caralex Intl Realty Group Corp

    441 La Fitte Rd, Summerland Key, FL 33042
  • /6

    $1,937,500

    Sold Jun 05, 2026

    1058 Buttonwood Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft
    • Built 2001

    Last Sold Summary

    • $1,096/SF
    • 0 Days On Market

    Current Estimated Value $1,906,466

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

    1058 Buttonwood Dr E, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      1693 Bayview Dr, Little Torch Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 917 Sq Ft
      • Built 1976
      1693 Bayview Dr, Little Torch Key, FL 33042

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Daiane SardinasCarvalh Centennial Realty Group LLC

  • /43

    $1,850,000

    $151K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,980 Sq Ft

    1607 Sunrise Dr, Big Pine Key, FL 33043

    Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1607 Sunrise Dr, Big Pine Key, FL 33043
  • /14

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    31226 Hollerich Dr Unit 1, Big Pine Key, FL 33043

    Exceptional waterfront rental opportunity available yearly or seasonally (minimum 28-day rental). This beautifully maintained 3-bedroom, 2-bath villa is located in the heart of Big Pine Key and offers direct water access with a private dock, making it ideal for boating, fishing, kayaking, and enjoying the Florida Keys lifestyle.Relax on the waterfront and take in the spectacular sunset views

    Annie Mora Tellado The Opulence Group Brokerage

    31226 Hollerich Dr Unit 1, Big Pine Key, FL 33043
  • /2

    $510,000

    Sold Sep 08, 2025

    Unlisted Address

    • 3 Beds
    • 2 Baths
    • 972 Sq Ft
    • Built 1989

    Last Sold Summary

    • $525/SF

    Current Estimated Value $528,837

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    Unlisted Address
    • /15

      Not Listed For Sale

      8 Calico Jack Circle Cir, Verifying, FL 33042

      8 Calico Jack Circle Cir, Verifying, FL 33042

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY

  • /39

    $485,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home withFlorida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • /49

    $5,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    3770 Park Ave, Big Pine Key, FL 33043

    Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

    Mary Jo Selden DomainRealty.com LLC

    3770 Park Ave, Big Pine Key, FL 33043
  • /3

    $510,000

    Sold Jun 18, 2026

    57 Pelican Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $538/SF
    • 23 Days On Market

    Current Estimated Value $545,931

    Last Listing Agent Elsa Machado Elsa Realty, LLC

    57 Pelican Ln, Big Pine Key, FL 33043
    • /40

      Not Listed For Sale

      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1996
      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  • /145

    $16,900,000

    • 5 Beds
    • 4 Baths
    • 3,352 Sq Ft

    0 Howell Key Unit 620413, Summerland Key, FL 33042

    Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled opportunity to own an off-grid luxury island with two building rights, allowing for one additional residence, surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    0 Howell Key Unit 620413, Summerland Key, FL 33042
  • /14

    $3,200 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,080 Sq Ft
    • Townhouse for Rent

    28528 Channel View Dr, Little Torch Key, FL 33042

    This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna, marina with boat ramp, outdoor games, bbq, kayaks and paddle

    Joseph Danieli AKT Realty LLC

    28528 Channel View Dr, Little Torch Key, FL 33042
  • /65

    $4,000

    Sold Jul 06, 2026

    30361 Hardin Rd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 888 Sq Ft
    • Built 1963

    Last Sold Summary

    • 20% Below List Price
    • $5/SF
    • 79 Days On Market

    Current Estimated Value $942,308

    Last Listing Agent Maris Delgado LoKation Real Estate - Key Largo

    30361 Hardin Rd, Big Pine Key, FL 33043
    • /38

      Not Listed For Sale

      27883 Coral Shores Rd, Little Torch Key, FL 33042

      • 2 Beds
      • 1.5 Baths
      • 720 Sq Ft
      • Built 1973
      27883 Coral Shores Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Tracey Petrusha LoKation

  • /37

    $700,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    29160 Primrose Ln, Big Pine Key, FL 33043

    Welcome to Eden Pines--now offered at an exceptional new price of $700,000! This charming 3-bedroom, 2-bath home sits on a spacious and private 10,000 sq. ft. lot in the heart of Big Pine Key. With a garage, abundant storage, a fully fenced yard, and room to add a pool, this property offers endless potential.Inside, you'll find an inviting open-concept floor plan, two beautifully updated

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    29160 Primrose Ln, Big Pine Key, FL 33043
  • /13

    $2,450 Per Month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Property for Rent

    31439 A, Big Pine Key, FL 33043

    Charming, fully furnished 1-bedroom, 1-bath cottage in Big Pine Key, conveniently located just off US-1 for easy access to local shopping, restaurants, and everything the Lower Keys has to offer. This cozy home features a screened-in covered porch, grassy backyard with partial fencing, off-street parking, and an on-site washer and dryer. Non-waterfront property. Available for a 6-12 month lease

    Melissa Gibbins Expert Realty LLC (HQ)

    31439 A, Big Pine Key, FL 33043
  • /58

    $572,000

    Sold May 27, 2026

    175 E Cahill Ct, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $567/SF
    • 40 Days On Market

    Current Estimated Value $569,942

    Last Listing Agent Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    175 E Cahill Ct, Big Pine Key, FL 33043
    • /2

      Est $1,073,531

      Not Listed For Sale

      527 Heck Ave, Little Torch Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 2023
      527 Heck Ave, Little Torch Key, FL 33042

  • /33

    $599,000

    Pre-Foreclosure
    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    30354 Palm Dr, Big Pine Key, FL 33043

    Private Lower Keys opportunity! Nestled behind a lush hedge of mature Areca palms, this 2BR/2BA CBS home offers privacy, solid construction, and endless potential. Recent improvements include a 2018 post-Irma roof and storm shutters. The fully fenced 6,250 sq. ft. lot provides ample space for a pool, outdoor living, or tropical gardens, with a storage shed already in place. Enjoy a peaceful

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    30354 Palm Dr, Big Pine Key, FL 33043
  • /34

    $11,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,352 Sq Ft
    • House for Rent

    Unlisted Address

    **Exclusive Waterfront Luxury Home in Big Pine Key** (minimum 6 months, available Sept 1.)Experience the ultimate Florida Keys getaway in this newly built, four-level, all-concrete waterfront home in beautiful Big Pine Key. Designed with luxury and comfort in mind, this spacious and light-filled property features 4 bedrooms and 2.5 bathrooms, with custom, high-end finishes and top-of-the-line

    Unlisted Address
  • /38

    $790,000

    Sold May 22, 2026

    30471 Coconut Hwy, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Built 1959

    Last Sold Summary

    • 14% Below List Price
    • $522/SF
    • 319 Days On Market

    Current Estimated Value $778,981

    Last Listing Agent Richard Haskins Buy The Keys

    30471 Coconut Hwy, Big Pine Key, FL 33043
    • /64

      Not Listed For Sale

      15 W Cooks, Cook Island Key, FL 33043

      • 3 Beds
      • 3 Baths
      • 1,551 Sq Ft
      • Built 1977
      15 W Cooks, Cook Island Key, FL 33043

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /97

    $1,199,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    17151 Marlin Dr, Sugarloaf Key, FL 33042

    This beautifully remodeled waterfront bungalow is nestled in the heart of Sugarloaf Shores ,one of the Lower Florida Keys' most desirable boating communities. Set on an expansive 12,500 sq ft lot surrounded by lush tropical landscaping, this elevated two-story home offers the perfect blend of privacy, comfort, and island charm. With 3 Bedrooms plus a Loft and 2 Bathrooms, the layout is

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17151 Marlin Dr, Sugarloaf Key, FL 33042
  • /13

    $5,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,080 Sq Ft
    • Townhouse for Rent

    28513 Channel View Dr, Little Torch Key, FL 33042

    This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished or furnished townhome for rent. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour community gym and

    Joseph Danieli AKT Realty LLC

    28513 Channel View Dr, Little Torch Key, FL 33042
  • /16

    $1,400,000

    Sold Mar 16, 2026

    570 Blackbeard Rd, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • Built 2026

    Last Sold Summary

    • 3% Below List Price
    • $933/SF
    • 14 Days On Market

    Current Estimated Value $1,138,333

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    570 Blackbeard Rd, Summerland Key, FL 33042
    • /50

      Est $818,629

      Not Listed For Sale

      489 Pirates Rd, Little Torch Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 1,638 Sq Ft
      • Built 1984
      489 Pirates Rd, Little Torch Key, FL 33042

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Jessica Celli Engel & Voelkers Key West

  • /19

    $199,000

    $16K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $3,980,000 per Acre

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

    Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • /47

    $11,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • House for Rent

    28577 Peg Leg Rd, Summerland Key, FL 33042

    Make the most of winter in the Florida Keys from this fully furnished waterfront retreat on Little Torch Key. Whether you're planning a seasonal stay, considering a move to the Keys, or looking for a comfortable home base while searching for a property of your own, this 3-bedroom, 2-bath home offers an easy way to settle in and experience island living.Located on the Atlantic side in

    Micaela Eleicegui Ocean Sotheby's International Realty

    28577 Peg Leg Rd, Summerland Key, FL 33042
  • /48

    $2,250,000

    Sold Aug 25, 2026

    1233 Avenue A, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1995

    Last Sold Summary

    • 17% Below List Price
    • $1,545/SF
    • 146 Days On Market

    Current Estimated Value $2,074,936

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1233 Avenue A, Big Pine Key, FL 33043
    • /9

      Not Listed For Sale

      Lots 23-24 Coral Way, Big Pine Key, FL 33043

      Lots 23-24 Coral Way, Big Pine Key, FL 33043

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.

  • /71

    $525,000

    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile homenestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
  • /23

    $5,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,654 Sq Ft
    • House for Rent

    31490 Avenue F, Big Pine Key, FL 33043

    Brand-New Waterfront Home in the Florida KeysDiscover the ultimate Florida Keys lifestyle in this stunning brand-new construction, perfectly designed for those who love boating, waterfront living, and the beauty of the Gulf. This exceptional property features 3 spacious bedrooms, 2.5 bathrooms, and a private boat dock, providing direct access to the Gulf for unforgettable days on the water.The

    31490 Avenue F, Big Pine Key, FL 33043
  • /61

    $592,000

    Sold May 29, 2026

    29951 Pine Channel Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft
    • Built 1989

    Last Sold Summary

    • 9% Below List Price
    • $649/SF
    • 80 Days On Market

    Current Estimated Value $589,549

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    29951 Pine Channel Rd, Big Pine Key, FL 33043
    • /50

      Not Listed For Sale

      701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2021
      701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

      Last Sold Summary

      • 245 Days On Market

      Last Listing Agent Joe Sappington Waterfront Keys Realty Inc.

Showing Results 41 - 80, Page 2 of 18

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