Summerland Key, FL Homes for Sale with Pool

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  $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, 5½ 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

  Greg MacLaren Internet Realty of the Florida Keys

  333 Indies Rd, Ramrod Key, FL 33042
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  /38

  $674,999

  • 2 Beds
  • 2 Baths
  • 770 Sq Ft

  701 Spanish Main Dr Unit 123, Cudjoe Key, FL 33042

  YOUR FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully furnished 2-bedroom, 2-bath home combines water views, exceptional boating access, comfortable island living, and resort-style amenities just seconds from open water.Situated on a wide 60' canal, boaters will love the 35' concrete

  Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

  701 Spanish Main Dr Unit 123, Cudjoe Key, FL 33042
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  /22

  $5,200,000

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

  1557 Long Beach Dr, Big Pine Key, FL 33043

  Coastal living awaits at this spacious property in Long Beach Estates on Big Pine Key! Offering exceptional privacy and direct access to island life, this lot features ample space for your island sanctuary. Located just minutes from pristine beaches, local dining, open water boating, and the Bahia Honda State Park. Perfectly situated in the heart of the Lower Keys, offering quiet, relaxed island

  Greisy Montes De Oca The Brokerage A Real Estate Company

  1557 Long Beach Dr, Big Pine Key, FL 33043
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  $1,269,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  116 Spanish Main Dr, Summerland Key, FL 33042

  Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

  Margaret Crowley Florida Keys Realty Group

  116 Spanish Main Dr, Summerland Key, FL 33042
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  $189,000

  • Land
  • 0 Sq Ft

  29859 Overseas Hwy #20, Big Pine, FL 33043

  Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across

  Liza Dieppa Coldwell Banker Realty

  29859 Overseas Hwy #20, Big Pine, FL 33043
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  $779,000

  $41K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1817 Watson Blvd, Big Pine Key, FL 33043

  Nestled in the heart of Big Pine Key, this 2-bedroom, 2-bath canal-front ranch style home offers a rare opportunity to enjoy the Florida Keys lifestyle while investing for exceptional future potential. Situated on an oversized 1 1/2 lot with direct boating access out to open water in 3 mins, this property is a true waterfront gem. The existing home provides comfortable island living with abundant

  Paul Rogers Coldwell Banker Schmitt RE Co.

  1817 Watson Blvd, Big Pine Key, FL 33043
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  /4

  $189,000

  • Land
  • 0 Sq Ft

  29859 Overseas Hwy, Big Pine Key, FL 33043

  Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across the

  Liza Dieppa Coldwell Banker Realty

  29859 Overseas Hwy, Big Pine Key, FL 33043
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  /40

  $4,400,000

  New Construction $75K PRICE INCREASE

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 6, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 6, Summerland Key, FL 33042
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  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
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  $1,435,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft

  29562 Saratoga Ave, Big Pine Key, FL 33043

  Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and

  Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

  29562 Saratoga Ave, Big Pine Key, FL 33043
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  $1,125,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 960 Sq Ft

  29565 Flying Cloud Ave, Big Pine Key, FL 33043

  Waterfront retreat with excellent boating access in the heart of Big Pine Key! Home has 15k boat lift, fish cleaning table and clear deep canal. This elevated home features a private dock, canal frontage, and plenty of room for boats, trailers outdoor entertaining and out door showers. Open-concept living areas, abundant natural light, and spacious porches create the perfect Keys getaway or

  Frank Kowalski Metro Dade Realty, Inc.

  29565 Flying Cloud Ave, Big Pine Key, FL 33043
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  /49

  $749,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  19543 Navajo St, Cudjoe Key, FL 33042

  3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

  Pamela Stangler Expert Realty LLC

  19543 Navajo St, Cudjoe Key, FL 33042
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  /6

  $1,775,000

  • 4 Beds
  • 4 Baths
  • 1,671 Sq Ft

  193 Galleon Ln, Cudjoe Key, FL 33042

  Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

  Joaquin Merlo-Garzon CRANELUXE

  193 Galleon Ln, Cudjoe Key, FL 33042
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  $2,069,000

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft

  1733 Sunrise Dr, Big Pine Key, FL 33043

  Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

  Norman De la Cruz Florida Realty of Miami Corp

  1733 Sunrise Dr, Big Pine Key, FL 33043
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  $1,469,000

  New Construction $80K PRICE DROP

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

  27374 Guadaloupe Ln, Summerland Key, FL 33042

  *Construction process underway. Expected completion November/December 2026Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27374 Guadaloupe Ln, Summerland Key, FL 33042
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  /31

  $998,000

  Open Sat 1PM - 3PM $57K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  83 Sugarloaf Dr, Summerland Key, FL 33042

  Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  83 Sugarloaf Dr, Summerland Key, FL 33042
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  /59

  $535,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
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  /59

  $3,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,409 Sq Ft

  17387 E Dolphin St, Sugarloaf Key, FL 33042

  Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or

  Jesus Parra Coldwell Banker Schmitt Real E

  17387 E Dolphin St, Sugarloaf Key, FL 33042
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  /4

  $189,000

  • Land
  • 0 Sq Ft

  29859 Overseas Hwy #21, Big Pine, FL 33043

  Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across

  Liza Dieppa Coldwell Banker Realty

  29859 Overseas Hwy #21, Big Pine, FL 33043
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  /55

  $329,000

  $98K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
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  /32

  $339,000

  $210K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

  Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
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  /54

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  31536 Avenue F, Big Pine Key, FL 33043

  If you're looking for a property that can wear many hats, this one deserves a closer look! The Big Pine Key Bungalow sits on a spacious waterfront lot where open-water views and glowing sunrise skies set the tone for every day. Whether you're searching for a full-time residence, a vacation retreat, or a turn-key investment with a well-established vacation rental history, this home offers

  Madeleine Young Island Welcome Real Estate LLC

  31536 Avenue F, Big Pine Key, FL 33043
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  /56

  $799,000

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  701 Spanish Main Dr Unit 171, Cudjoe Key, FL 33042

  YOUR OCEAN FRONT FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully maintained 2-bedroom, 2-bath elevated home combines incredible ocean views, exceptional boating access, and resort-style living in one of the Lower Keys' most desirable waterfront communities.Step inside to soaring

  Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

  701 Spanish Main Dr Unit 171, Cudjoe Key, FL 33042
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  $3,500,000

  • 3 Beds
  • 3 Baths
  • 2,535 Sq Ft

  25361 1st St, Summerland Key, FL 33042

  Experience the pinnacle of Florida Keys waterfront living in this exceptional 3-bedroom, 3-bathroom oceanfront estate offering breathtaking open water views, deep-water dockage, and sophisticated modern design throughout. Thoughtfully designed for luxury, comfort, and entertaining, this stunning residence seamlessly blends elegant architecture with the beauty of its coastal surroundings. The

  Tommy Mack Coastal Collection Real Estate Inc.

  25361 1st St, Summerland Key, FL 33042
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  /21

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  19421 Canal Dr, Summerland Key, FL 33042

  Great opportunity to have your home in a charming neighborhood on Sugarloaf key, MM 19.5. Enjoy your 3-bedroom 2-bath single family home on a large 15000 sq ft lot with screened front porch and open patio in the backyard. This large yard has plenty of room for a pool, Boats, RV, Trailers and your toys! Home is located down the street from Sugarloaf School, 20 miles to Key West and 27 miles to

  Rosa Cappiello Century 21 Circle- Islamorada

  19421 Canal Dr, Summerland Key, FL 33042
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  /47

  $4,650,000

  $2M PRICE DROP

  • 3 Beds
  • 3 Baths
  • 4,687 Sq Ft

  3742 Seagrape St, Big Pine Key, FL 33043

  Escape to “The Castle”, a luxurious gated Gulf-front estate spanning 1.14 acres on Big Pine Key. Built in 2014 with poured concrete, impact windows/doors, elevator, and generator, this 4,600+ sq. ft. masterpiece offers 3 bedrooms, 3 baths, and breathtaking Gulf views. Boaters enjoy 235’ of dockage: 140’ protected canal dock with lift, ramp, and slip, plus 95’ open-water pier dock with lift and

  Jo Ann Cook Ocean Sotheby's International

  3742 Seagrape St, Big Pine Key, FL 33043
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  /55

  $1,799,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  22970 Gasparilla Ln, Cudjoe Key, FL 33042

  OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELEVATED 3 bedroom, 2 bathroom CBS home is a must see! Solid steel and concrete, standing seam white metal roof with impact windows and doors rated to 185 MPH. 2,050 total sq ft of living space includes a front porch, utility room on the lower level and a lanai off the back. A total of 1500 sq ft of living

  Joyce Craul Expert Realty LLC (HQ)

  22970 Gasparilla Ln, Cudjoe Key, FL 33042
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  /27

  $350,000

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 726 Sq Ft

  701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

  Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

  Monika Rydzak EXP Realty LLC

  701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

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