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
  • /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
  • /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

  • /22

    $685,000

    $29K PRICE DROP Under Contract
    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    4039 Egret Ln, Summerland Key, FL 33042

    Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    4039 Egret Ln, 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
  • /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

  • /46

    $795,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    29034 Rose Dr, Big Pine Key, FL 33043

    Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is

    Agent Photo

    Ryan Gernaat

    Coldwell Banker Schmitt Lower Keys (KW)

    29034 Rose Dr, 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

    $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

  • /43

    $1,799,000

    • 3 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    51 Sawyer Dr, Cudjoe Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    51 Sawyer Dr, 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: 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
  • /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 $671,739

    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

  • /73

    $2,849,000

    $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft

    17041 Marlin Dr, Sugarloaf Key, FL 33042

    Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17041 Marlin Dr, Sugarloaf 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 $731,320

    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

  • /37

    $665,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,497 Sq Ft

    30416 Coconut Hwy, Big Pine Key, FL 33043

    Looking for land in the Keys and a well-maintained home? This rare 25,000 sq. ft. property spans more than 1⁄2 acre, with room for a pool and/or tiki hut, RV, boat trailers, and more. The four lots are bordered by Coconut Hwy., Avenue B, and Hibiscus Ln., with vehicle access to the large, fenced backyard. The 1,497 sq. ft. CBS home blends ''old Keys'' charm with thoughtful updates, including

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    30416 Coconut Hwy, 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

  • /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
  • /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 $950,964

    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

  • /9

    $899,000

    • Land
    • 12,000 Sq Ft
    • $3,263,370 per Acre

    24764 Overseas Hwy, Summerland Key, FL 33042

    Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet of premium frontage - both on the highly visible Overseas Highway and on deep-water accessible oceanside canal - this property delivers exceptional visibility and flexible commercial potential. 120' concrete dockage with direct

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    24764 Overseas Hwy, Summerland 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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