8,633

Summerland Key, FL Homes

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  • /72

    $3,899,000

    $100K PRICE DROP
    • 3 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
  • /24

    Starting at $2,500 Per Month

    • 2 Beds

    21585 Overseas Hwy, Cudjoe Key, FL 33042

    Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

    Coco Palms

    21585 Overseas Hwy, Cudjoe Key, FL 33042
  • /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 $1,091,333

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    325 Pirates Rd, Summerland Key, FL 33042
    • /63

      Est $1,964,276

      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

  • /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
  • /20

    Starting at $3,999 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
  • /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 $1,620,415

    Last Listing Agent Callie Harris Brenda Donnelly Real Estate LLC

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

  • /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
  • /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: 2514237Annual 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
  • /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 $951,227

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

    76 W Shore Dr, Summerland Key, FL 33042
    • /44

      Not Listed For Sale

      701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 828 Sq Ft
      • Built 2002
      701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

      Last Sold Summary

      • 8 Days On Market

  • /76

    $1,550,000

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    29424 Forrestal Ave, Big Pine Key, FL 33043

    If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    29424 Forrestal Ave, Big Pine Key, FL 33043
  • /7

    $3,000 Per Month

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

    4166 Dorn Rd, Summerland Key, FL 33042

    Property Id: 2728964This Very Nice Home is available on a 28 day minimum term. 2 bedroom, 2 bath home in a quiet neighborhood with 60 Ft dock. Deep water access to gulf or Atlantic. Fully furnished. Please email, call or text questions if interested. Tours are not available.All excellent appliances, gas stove with convection/electric oven, and bait freezer downstairs.

    4166 Dorn Rd, Summerland Key, FL 33042
  • /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 $910,802

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

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

      Est $512,677

      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

  • /62

    $1,299,999

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    28560 Doubloon Rd, Summerland Key, FL 33042

    Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    28560 Doubloon Rd, 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
  • /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 $1,552,288

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

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

      Est $1,825,423

      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

  • /21

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,304 Sq Ft

    75 Lobstertail Rd, Big Pine Key, FL 33043

    Enjoy easy island living in this beautifully updated 2BD/2BA elevated home set along a peaceful plugged canal--perfect for paddleboarding and enjoying the waterfront ambiance (no boating access).Inside, the open living space features vaulted ceilings, luxury plank vinyl flooring throughout, and great natural light, flowing out to a screened porch overlooking the canal. The standout chef's

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    75 Lobstertail Rd, Big Pine Key, FL 33043
  • /18

    $3,400 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
  • /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 $664,476

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    22970 Sharp 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

  • /40

    $1,899,000

    $100K PRICE DROP Under Contract
    • 3 Beds
    • 3 Baths
    • 1,998 Sq Ft

    28573 Le Grand Rd, Little Torch Key, FL 33042

    This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    28573 Le Grand Rd, Little Torch Key, FL 33042
  • /41

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 6,098 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 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 home offers the

    Lisa Guirguis Genesis Realty Team

    280 Airport Dr S, 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 $739,364

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    40 Munson Ave, 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

  • /48

    $698,800

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,039 Sq Ft

    29048 Iris Dr, Big Pine Key, FL 33043

    This 50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    29048 Iris Dr, Big Pine Key, FL 33043
  • /19

    $4,324

    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 $4,324/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 26, 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
  • /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 $268,614

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    • /36

      Est $905,406

      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

  • /58

    $979,000

    $30K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    27358 Jamaica Ln, Summerland Key, FL 33042

    Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with water on 2 sides this property offers 150' of waterfront including a deep water basin, excellent dockage and easy access for boating, fishing, kayaking, or paddle boarding right from your backyard. Offering a flexible floor plan

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    27358 Jamaica 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
  • /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 $938,861

    Last Listing Agent Mark Gable Engel & Volkers Marathon

    27405 Guadaloupe Ln, Summerland Key, FL 33042
    • /46

      Not Listed For Sale

      701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 754 Sq Ft
      • Built 1989
      701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

      Last Sold Summary

      • 72 Days On Market

  • /10

    $499,000

    • Land
    • 14,706 Sq Ft
    • $1,478,066 per Acre

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    63 Sugarloaf Dr, Sugarloaf 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
  • /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 $1,589,567

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

    1058 Buttonwood Dr E, Summerland 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

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,157,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$927,500
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$908
Number of Homes for Sale
55
Last 12 months Home Sales
117
Months of Supply
5.60
Median List Price
$1,277,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
1%
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