Summerland Key, FL Homes

• 

  

  

  /27

  $320,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

  Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
• 

  

  

  /14

  $225,000

  Sold Apr 01, 2026

  27398 Jamaica Ln, Ramrod Key, FL 33042

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  Last Sold Summary

  • 25% Below List Price
  • 173 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  

  /39

  Est $671,979

  Not Listed For Sale

  25161 Center St, Summerland Key, FL 33042

  • 1 Bed
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1958

  25161 Center St, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  

  /7

  $799,990

  • Land
  • 7,840 Sq Ft
  • $4,444,389 per Acre

  28525 Jolly Roger Dr, Little Torch Key, FL 33042

  RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

  Fazana Haniff FL Home Group LLC

  28525 Jolly Roger Dr, Little Torch Key, FL 33042
• 

  

  

  /36

  $1,200,000

  Sold Jun 05, 2026

  831 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1980

  Last Sold Summary

  • 19% Below List Price
  • $1,038/SF
  • 87 Days On Market

  Current Estimated Value $1,439,667

  Last Listing Agent Miranda Dender Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  831 W Indies Dr, Summerland Key, FL 33042
• 

  

  /40

  Est $2,227,481

  Not Listed For Sale

  20995 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft
  • Built 2007

  20995 2nd Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /47

  $445,000

  $10K PRICE DROP

  • Land
  • 2,078 Sq Ft
  • $9,328,296 per Acre

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

  ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
• 

  

  /30

  $1,185,000

  Sold Nov 17, 2025

  478 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $1,062/SF
  • 0 Days On Market

  Current Estimated Value $1,221,646

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /49

  Est $6,992,903

  Not Listed For Sale

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft
  • Built 1992

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 7 Days On Market
• 

  

  /23

  $1,050,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  1331 Hudgins Dr, Summerland Key, FL 33042

  Construction Location Orientation. A Beautifully Appointed Canal Front Fortress All Concrete: Floors Walls Stairs Walk Around Ramp Driveway Deck & Seawall. All Solar Glazed and Insulated Impact windows Enter the Unique Palm Tree Stained-glass Impact door to 24-inch Travertine floors and Nine-foot ceilings throughout. Master Bedroom has French doors with a Tropical Stained-Glass Floral Cascade

  Camilo Perez Home Sold Realty, LLC

  1331 Hudgins Dr, Summerland Key, FL 33042
• 

  

  /29

  $825,000

  Sold Feb 27, 2026

  17245 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $661/SF
  • 104 Days On Market

  Current Estimated Value $864,869

  Last Listing Agent Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /30

  Est $919,135

  Not Listed For Sale

  31625 Warner St, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Built 1937

  31625 Warner St, Big Pine Key, FL 33043

  Last Sold Summary

  • 3 Days On Market
• 

  

  /28

  $639,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  31124 Avenue C, Big Pine Key, FL 33043

  Welcome to an inviting, well-priced island home in Big Pine Key, perfectly suited for families, military buyers, or anyone seeking relaxed Florida Keys living with modern upgrades already done. This beautifully renovated 2-bedroom, 2-bath home was thoughtfully updated in 2024 and blends comfort, privacy, and tropical charm. Inside, you'll find new luxury vinyl flooring throughout, a refreshed

  Dawn McComish Lokation Real Estate

  31124 Avenue C, Big Pine Key, FL 33043
• 

  

  /48

  $1,070,000

  Sold Jun 11, 2026

  1547 Gardenia Ln, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 2025

  Last Sold Summary

  • 18% Below List Price
  • $563/SF
  • 93 Days On Market

  Current Estimated Value $1,139,542

  Last Listing Agent Dorothy Santiago Keller Williams Realty Profess

  1547 Gardenia Ln, Big Pine Key, FL 33043
• 

  

  /57

  Est $1,504,648

  Not Listed For Sale

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  468 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 215 Days On Market
• 

  

  /3

  $195,000

  • Land
  • 0 Sq Ft

  29859 Overseas Hwy Unit LOT 19, Big Pine Key, FL 33043

  Rare opportunity to own a 920 sq. ft. transient commercial RV lot in Big Pine Key, one of the few properties in the Florida Keys that allows daily rentals. Currently rented with immediate cash flow. With transient vacation rentals permitted, the property offers the potential to significantly increase returns and potentially triple the income through short-term rentals. Ideal for investors seeking

  Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit LOT 19, Big Pine Key, FL 33043
• 

  

  /40

  $1,300,000

  Sold Feb 26, 2026

  537 Heck Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • Built 1997

  Last Sold Summary

  • $914/SF
  • 29 Days On Market

  Current Estimated Value $1,282,502

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  537 Heck Ave, Summerland Key, FL 33042
• 

  

  /40

  Est $920,561

  Not Listed For Sale

  93 Venetian Way, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1983

  93 Venetian Way, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market
• 

  

  /53

  $1,710,000

  $89K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /45

  $799,000

  Sold Aug 29, 2025

  17338 Dolphin St E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1963

  Last Sold Summary

  • 30% Below List Price
  • $426/SF
  • 171 Days On Market

  Current Estimated Value $932,339

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
• 

  

  /48

  Est $686,791

  Not Listed For Sale

  27018 Angelfish Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1992

  27018 Angelfish Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 15 Days On Market
• 

  

  /14

  $3,900

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  28528 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 6/30/26.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.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,

  Joseph Danieli AKT Realty LLC

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

  

  /47

  $1,075,000

  Sold Jul 30, 2025

  128 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1999

  Last Sold Summary

  • 16% Below List Price
  • $960/SF
  • 189 Days On Market

  Current Estimated Value $1,097,784

  Last Listing Agent Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

  128 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /19

  Est $917,946

  Not Listed For Sale

  221 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1985

  221 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 498 Days On Market
• 

  

  /86

  $3,199,000

  $500K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,744 Sq Ft

  17183 Coral Dr, Summerland Key, FL 33042

  Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

  Jan Fritz Coldwell Banker Schmitt RE Co.

  17183 Coral Dr, Summerland Key, FL 33042
• 

  

  /42

  $920,000

  Sold Jun 18, 2026

  22954 Buccaneer Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $657/SF
  • 30 Days On Market

  Current Estimated Value $935,625

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22954 Buccaneer Ln, Cudjoe Key, FL 33042
• 

  /2

  Est $1,143,816

  Not Listed For Sale

  27310 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft
  • Built 1984

  27310 W Indies Dr, Summerland Key, FL 33042
• 

  /2

  $85,000

  • Land
  • 6,667 Sq Ft
  • $555,279 per Acre

  Vacant Central Ave, Big Pine Key, FL 33043

  Tier 2 parcel with potential eligibility for ROGO points toward future building permits in Monroe County. Buyer to verify ROGO point availability and requirements with Monroe County. Adjacent lot is for sale MLS#618997

  Deni Heintzelman KeyIsle Realty

  Vacant Central Ave, Big Pine Key, FL 33043
• 

  

  /37

  $830,000

  Sold Jun 10, 2026

  153 Peg Leg Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $690/SF
  • 91 Days On Market

  Current Estimated Value $903,644

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  153 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /36

  Est $952,743

  Not Listed For Sale

  27328 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,518 Sq Ft
  • Built 1979

  27328 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 22 Days On Market
• 

  

  /52

  $3,899,000

  • 6 Beds
  • 6 Baths
  • 3,029 Sq Ft

  1557 Long Beach Dr, Big Pine Key, FL 33043

  Welcome to The Barnacle Bed and Breakfast, a rare oceanfront offering in Big Pine Key where island living meets income opportunity. This beautifully updated waterfront property allows you to live the Florida Keys lifestyle while hosting it or operate a turnkey hospitality investment in one of the most sought-after settings in the Lower Keys. The property has undergone an extensive renovation over

  Surelis Yanes Miami Portfolio Collection

  1557 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /34

  $762,000

  Sold Jan 22, 2026

  726 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1986

  Last Sold Summary

  • 15% Below List Price
  • $486/SF
  • 325 Days On Market

  Current Estimated Value $797,856

  Last Listing Agent Natallie Liz Expert Realty LLC (HQ)

  726 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /61

  Est $2,137,336

  Not Listed For Sale

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1998

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  Last Sold Summary

  • 30 Days On Market
• 

  

  /66

  $2,795,000

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

  Greg MacLaren Internet Realty of the Florida Keys

  333 Indies Rd, Ramrod Key, FL 33042
• 

  

  /47

  $1,375,000

  Sold May 20, 2026

  16823 E Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $790/SF
  • 46 Days On Market

  Current Estimated Value $1,386,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  16823 E Point Dr, Summerland Key, FL 33042
• 

  

  /81

  Est $1,282,354

  Not Listed For Sale

  23041 Snapper Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1992

  23041 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market
• 

  

  /32

  $2,100,000

  New Construction

  • 5 Beds
  • 4 Baths
  • 2,886 Sq Ft

  662 Blackbeard Rd, Little Torch Key, FL 33042

  Pre-Construction Luxury Home | Jolly Roger EstatesIntroducing a rare pre-construction opportunity in the desirable waterfront community of Jolly Roger Estates. This CBS-built, fortress-like home is designed for durability, efficiency, and modern coastal living. The two-story floor plan offers 5 bedrooms, 4 bathrooms, and 2,886 square feet of living space, along with a spacious downstairs storage

  Lanny Gardner Bluescape Real Estate

  662 Blackbeard Rd, Little Torch Key, FL 33042
• 

  

  /40

  $1,115,000

  Sold Sep 10, 2025

  28552 Maracaibo Rd, Little Torch Key, FL 33042

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

  Last Sold Summary

  • 3% Below List Price
  • $1,129/SF
  • 8 Days On Market

  Current Estimated Value $1,148,414

  Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

  28552 Maracaibo Rd, Little Torch Key, FL 33042
• 

  /2

  Est $885,782

  Not Listed For Sale

  22910 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1988

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /15

  $644,500

  • Land
  • 15,200 Sq Ft
  • $1,847,001 per Acre

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042

Showing Results 441 - 480, Page 12 of 18