Summerland Key, FL Homes

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  /46

  $2,999,999

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  653 Sawyer Dr, Summerland Key, FL 33042

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 238-6782

  653 Sawyer Dr, Summerland Key, FL 33042
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  /70

  $12,500 per month

  • 4 Beds
  • 4 Baths
  • 2,952 Sq Ft
  • Property for Rent

  21640 Overseas Hwy, Summerland Key, FL 33042

  Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 442-3255

  21640 Overseas Hwy, Summerland Key, FL 33042
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  /42

  $749,000 Sold Sep 19, 2025

  • 1,008 Sq Ft
  • $743/SF
  • 88 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  28009 Gulf Blvd, Big Pine Key, FL 33043

  Canal-Front Paradise in the Heart of the National Key Deer RefugeBig Pine Key, FloridaWelcome to your serene island escape! Nestled in the heart of the National Key Deer Refuge, this beautifully renovated two-bedroom, two-bath stilt home offers the perfect blend of modern comfort and natural beauty.Property Highlights:Canal-Front Property with ample space for a dock -- ideal for boating

  Ian Calderwood Bluescape Real Estate

  28009 Gulf Blvd, Big Pine Key, FL 33043
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  /62

  Est $4,796,311 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,421 Sq Ft

  1141 Ocean Dr, Summerland Key, FL 33042

  1141 Ocean Dr, Summerland Key, FL 33042
• 

  

  

  /41

  $1,172,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  22946 Bluegill Ln, Summerland Key, FL 33042

  If you are looking for the ''Island Life'' with the best boating access in the Keys, this is the property for you. This beautifully updated tropical Keys home on a lushly landscaped spacious 10,200 square foot lot, is located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable for its premier boating access to world class fishing and diving in both

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 787-3949

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /20

  $3,960 - $4,500 per month

  Little Torch Cottages

  2 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

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

  

  /43

  $675,000 Sold Sep 19, 2025

  • 1,162 Sq Ft
  • $581/SF
  • 118 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1978

  10 W Cook, Cook Island Key, FL 33043

  Welcome to Cook Island, a semi-private pristine barrier island offering one of the most beautiful beaches in the Florida Keys. Cook Island is home to just 11 residences and 10W is one of the few offering dockage accessible at low tide . This self-sustaining beach-front property sprawls over 3/4 of an acre and features a 2 Bedroom main house plus a detached beach-front studio with sleeping loft

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  10 W Cook, Cook Island Key, FL 33043
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  /76

  Est $1,526,402 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,834 Sq Ft

  1063 Avenue A, Big Pine Key, FL 33043

  1063 Avenue A, Big Pine Key, FL 33043
• 

  

  /24

  $899,000 Pending

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

  29153 Cedar Dr, Big Pine Key, FL 33043

  This beautiful home sits on TWO LOTS FULLY FENCED and has 100' of canal frontage with a concrete seawall and a #15,000 boat lift. Can easily be converted into a 3/2 with very little expense. Great boating access to both the Atlantic and Gulf. It is move in ready, just bring your boat. Impeccably maintained, this home includes impact windows and doors and a metal roof for EXTREMELY LOW INSURANCE

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 770-5969

  29153 Cedar Dr, Big Pine Key, FL 33043
• 

  

  /14

  $6,500 per month

  • 7 Beds
  • 6 Baths
  • 3,249 Sq Ft
  • House for Rent

  21660 Overseas Hwy, Summerland Key, FL 33042

  Private Oceanfront Beach House - Annual Rental AvailableYour private slice of the Florida Keys, just 20 minutes from Key West. This direct oceanfront home offers sweeping Atlantic views and the ultimate coastal escape.Inside, you'll find an airy layout with plenty of natural light, stainless steel appliances, French doors, impact-rated sliders, doors, and windows, plus updated AC units for

  Kelly Gardner Bluescape Real Estate

  21660 Overseas Hwy, Summerland Key, FL 33042
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  /43

  $595,000 Sold Sep 18, 2025

  • 912 Sq Ft
  • $652/SF
  • 114 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  29156 Tulip Ln, Big Pine Key, FL 33043

  This home offers privacy with an over-sized grass yard, surrounded by nature with a natural garden and room for all your needs. This double lot property is 10,000SF with room for a pool, tiki and/or an accessory structure. French doors take you to an additional 500+SF screened patio that extends your living space and provides tranquil views over the garden and lush yard. Spend your mornings

  Donna Halstead Coldwell Banker Schmitt RE Co.

  29156 Tulip Ln, Big Pine Key, FL 33043
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  /63

  Est $1,924,399 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,366 Sq Ft

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  17057 Bonita Ln W, Sugarloaf Key, FL 33042
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  /36

  $1,100,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  29185 Bougainvillea Ln, Big Pine Key, FL 33043

  This home has a lot to offer! Great home, great neighborhood, great lot! This home is situated on a 8,400 SF corner lot, with canal on two sides. Plenty of concrete seawall equipped with both a boat lift, and davits. There are no bridges to worry about getting under, and a short ride to the open water. The home has been recently updated, and there is plenty of room for people and fishing

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (833) 707-1770

  29185 Bougainvillea Ln, Big Pine Key, FL 33043
• 

  

  /20

  $8,100 per month

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

  886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042

  Loggerhead Lagoon is a stunning, tropically themed 3-bedroom 2-bathroom home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico. This rare find boasts a lush outdoor area full of beautiful palms, sun loungers, and tons of Florida sunshine. Located in Sugarloaf Key, just 19 miles from Key West and the world-famous Duval Street, this

  886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042
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  /40

  $950,000 Sold Sep 17, 2025

  • 1,152 Sq Ft
  • $825/SF
  • 85 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  Welcome to your slice of paradise in one of the Lower Keys' most desirable communities--Sugarloaf Key! Here you'll enjoy island living with the convenience of being just 25 minutes from Key West, and close to popular restaurants, a weekly farmers market, and miles of scenic bike and walking paths.This waterfront home sits on a wide, aqua-colored canal with 100 feet of concrete dock--perfect for

  Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
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  /9

  Not Listed For Sale

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Lot 8 Overseas Hwy, Summerland Key, FL 33042
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  /41

  $1,199,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  237 La Fitte Rd, Summerland Key, FL 33042

  Located in Little Torch Key, this 2-Bedroom, 1144 sq ft waterfront home boasts breathtaking open water views offering a front-row seat to mesmerizing sunrises and tranquil ocean breezes. Enter into the bright and airy Great Room where a wall of impact glass windows look out to picture perfect water views. The open Kitchen features top-grade appliances, sleek wood and granite countertops, ample

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 937-0738

  237 La Fitte Rd, Summerland Key, FL 33042
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  /20

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Property for Rent

  1129 Gordon Dr, Big Pine Key, FL 33043

  Tropical Island Living in Big Pine Key! Welcome to your slice of paradise! This beautifully renovated property offers: a long term residential lease for 1 yearTwo bedroom and two bathrooms for $4,200 +$300 for one monthly cleaning. plus $175 additional for the yard care and utility expenses energy, water, propane for generator. Tank will be full at commencement of lease.Upstairs: A fully

  Jennifer Howe Coastal Collection Real Estate Inc.

  1129 Gordon Dr, Big Pine Key, FL 33043
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  /40

  $640,000 Sold Sep 15, 2025

  • 912 Sq Ft
  • $702/SF
  • 54 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  3806 Dyer Rd, Big Pine Key, FL 33043

  Enjoy canal-front living in peaceful Port Pine Heights, where you're sure to see the diminutive key deer roaming daily. This 2BD/2BA home on a 7,963 sq. ft. corner lot is just two canals away from open water leading to calm, backcountry waters and the Content Keys, as well as the Atlantic for offshore activities. The interior is light and bright with a slight cathedral ceiling; the kitchen and

  Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  3806 Dyer Rd, Big Pine Key, FL 33043
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  /63

  Est $4,830,667 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 4,200 Sq Ft

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042
• 

  

  /35

  $650,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  31463 Avenue A, Big Pine Key, FL 33043

  Welcome to Hibiscus House, your private island retreat in the heart of the Key Deer Sanctuary. This updated 3-bedroom, 2-bathroom home offers 1,300 sq ft of comfortable living space on a fully fenced 5,000 sq ft lot. Upon entering the home, you are welcomed by abundant natural light, showing off a generous living space, with lofty ceilings and luxury vinyl flooring throughout. The recently

  

  Ryan Gernaat

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 578-1681

  31463 Avenue A, Big Pine Key, FL 33043
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  /9

  $2,125 per month

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft
  • House for Rent

  31020 Avenue B, Big Pine Key, FL 33043

  Property Id: 2043481 $2125. for one person. Cozy 1 Bedroom, 1 Bath Mobile Home This well-maintained mobile home features laminate flooring, a screened-in back porch, and a small fenced side and backyard. Parking for 2 vehicles max. It includes washer/dryer hookups and an on-demand water heater. The home is unfurnished, and utilities are not included. Lease Terms: Maximum 2 people .

  31020 Avenue B, Big Pine Key, FL 33043
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  /75

  $830,000 Sold Sep 15, 2025

  • 1,200 Sq Ft
  • $692/SF
  • 84 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  22738 Blackbeard Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Cudjoe Key, this thoughtfully designed waterfront residence offers the ideal blend of comfort, durability, and island style. A large paver driveway leads to a spacious under-home parking area with room for two vehicles, while a concrete drive wraps around to a second covered patio--offering ample space for guests, toys, or trailers.Composite decking leads to a

  Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
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  /57

  $2,999,000 Under Contract

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft

  22967 Redfish Ln, Cudjoe Key, FL 33042

  Custom Luxury Meets Waterfront Living on Cudjoe Key. Welcome to 22967 Redfish Lane -- a one-of-a-kind luxury home crafted by one of the Keys' most respected builders as his personal residence. This 3,747 sq ft coastal estate offers 3 bedrooms, 3.5 baths, and high-end custom finishes throughout.Step inside to find black walnut hardwood flooring, soaring tongue-and-groove ceilings, and a true

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 900-8075

  22967 Redfish Ln, Cudjoe Key, FL 33042
• 

  

  /24

  $3,700 per month

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

  30867 Delgado Ln, Big Pine Key, FL 33043

  A great waterfront family home with brand new granite, new cabinets, SS appliances, driftwood decor flooring, updated baths, brand new impact patio slider doors, brand new accent drapes, freshly painted interior/exterior, remote ceiling fans, large bedrooms, brand new blinds, washer/dryer in laundry room walk-out deck facing north, giant yard/double lot for parking/toys, heavy davits along 100'

  Paul Rogers Coldwell Banker Schmitt RE Co.

  30867 Delgado Ln, Big Pine Key, FL 33043
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  /34

  $580,000 Sold Sep 15, 2025

  • 1,080 Sq Ft
  • $537/SF
  • 137 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1972

  30868 Malaga Ln, Big Pine Key, FL 33043

  Updated adorable 3 bedroom, 1 bath canal-front home situated in the desirable Doctor's Arm neighborhood of Big Pine Key. Enjoy direct, bridge-free access to open water. The property includes approval for a boat lift by the Dept of the Army Corp of Engineers, which can be transferred to the new owner.This home has been tastefully updated, featuring stainless steel appliances, newer electric

  Loren Rea Truman & Co. (KW)

  30868 Malaga Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  0000 Watson Blvd, Big Pine Key, FL 33043

  0000 Watson Blvd, Big Pine Key, FL 33043
• 

  

  /45

  $565,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,055 Sq Ft

  2421 Pensacola Rd, Big Pine Key, FL 33043

  LOWEST PRICED 3-BEDROOM STILT HOME IN THE KEYS! At 15-ft elevation, this home stands out for affordability and resilience, especially given the recent upgrades. *NEW Mitsubishi mini splits (2025) efficiently cool and heat the 1,055 sq. ft. living area *NEW Cali Bamboo Flooring (2025) *NEW tile floors in the Entry, Kitchen and Bath (2025) *NEW Bath Remodel (2025) *NEW energy-efficient GE

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 455-5467

  2421 Pensacola Rd, Big Pine Key, FL 33043
• 

  

  /12

  $4,800 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  467 W Shore Dr, Summerland Key, FL 33042

  Property Id: 1850307Welcome to your dream home in the heart of Summerland Key! Located at MM25 in the coveted Summerland Key Cove neighborhood conveniently located near restaurants, shopping, and boat ramps. This spacious property features modern amenities such as a stainless steel appliances, central AC, and in ground swimming pool. Extra large driveway with plenty of off street parking

  467 W Shore Dr, Summerland Key, FL 33042
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  /52

  $2,300,000 Sold Sep 12, 2025

  • 2,586 Sq Ft
  • $889/SF
  • 147 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  23086 Snapper Ln, Summerland Key, FL 33042

  Oceanfront CBS Fortress with Breathtaking Atlantic Ocean Views and Deep Draft Protected Dockage. Experience unparalleled coastal living with stunning, unobstructed views of the Atlantic Ocean and Kemp Channel from this oversized 12,000 sq. ft. corner lot. This one-of-a-kind CBS home is built for strength and style, offering the ultimate in durability and design. Featuring 4 bedrooms, 3 baths, and

  Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
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  /2

  Est $235,975 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
• 

  

  /27

  $699,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  25081 Overseas Hwy, Summerland Key, FL 33042

  So many opportunities at this 3 Bedroom 2 Bath canal front home located in the Special Fishing District on Summerland Key where home businesses including commercial fishing and boat mechanics are allowed. Boasting 60' of road frontage with excellent highway visibility and 60' of concrete canal dockage with quick and easy access to the gulf and ocean. The newly remodeled coastal style home

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 828-1613

  25081 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /13

  $5,500 per month

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

  28515 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 10/31/25.This is a waterfront 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, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated

  Joseph Danieli AKT Realty LLC

  28515 Channel View Dr, Little Torch Key, FL 33042
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  /38

  $775,000 Sold Sep 11, 2025

  • 1,008 Sq Ft
  • $769/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  22957 Drake Ln, Cudjoe Key, FL 33042

  Excellent boating and pretty open water views down the canal at this gorgeous Cudjoe Key retreat! Enjoy quick no-bridge access to Cudjoe Bay for frequent boating and fishing adventures with ease. Inside this well-maintained home, the main living area boasts high ceilings and an open concept. The well-equipped kitchen features stainless steel appliances, abundant storage, and a large center island

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22957 Drake Ln, Cudjoe Key, FL 33042
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  /33

  Est $807,029 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  28120 County Rd, Little Torch Key, FL 33042

  28120 County Rd, Little Torch Key, FL 33042
• 

  

  /69

  $1,425,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  1667 Bogie Dr, Big Pine Key, FL 33043

  'Smuggler's Cove' is rich in history and a bit of mystery, as its name would suggest. Fast forward to the present and you'll discover that this 1948 home has kept much of its character with lots of hidden alcoves, while offering modern updates including a top-of-the-line appliances, USB electric outlets throughout, a 7.2 Yamaha surround-sound theatre system and so much more.Once inside the gated

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (844) 791-2437

  1667 Bogie Dr, Big Pine Key, FL 33043
• 

  

  /9

  $4,800 per month

  • 2 Beds
  • 1 Bath
  • Apartment for Rent

  29420 Enterprise Ave Unit B, Big Pine Key, FL 33043

  Enjoy the best of Keys living in this beautifully renovated 2 bedroom, 1 bath upstairs unit in Big Pine Key. This spacious home offers stunning open water views and direct canal access perfect for boating enthusiasts, with room to dock your boat right outside.Inside, you'll find a modern feel with top-of-the-line appliances, a washer and dryer, and high-end finishes throughout. The open floor

  Halley Haack Coldwell Banker Schmitt RE Co.

  29420 Enterprise Ave Unit B, Big Pine Key, FL 33043
• 

  

  /34

  $650,000 Sold Sep 10, 2025

  • 1,392 Sq Ft
  • $467/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1994

  558 E Shore Dr, Summerland Key, FL 33042

  Single-family property on a dry lot in Summerland Key. This property features 3 bedrooms and 2 bathrooms, along with a downstairs enclosure. It sits on a spacious lot of over 9,000 square feet. Residents have exclusive access to an association that provides a boat ramp and dockage. This property features a beautifully remodeled kitchen, perfect for entertaining and family gatherings. Welcoming

  Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  558 E Shore Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,059,856 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  17277 Dolphin St E, Summerland Key, FL 33042

  17277 Dolphin St E, Summerland Key, FL 33042

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