Summerland Key, FL Homes for Sale with Pool

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  /62

  $2,599,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  16843 E Point Dr, Summerland Key, FL 33042

  Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle. Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious bedrooms and

  Suzanne Moore Truman & Co. (KW)

  16843 E Point Dr, Summerland Key, FL 33042
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  /58

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  885 Hawksbill Ln, Summerland Key, FL 33042

  Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus

  Tommy Mack Coastal Collection Real Estate Inc.

  885 Hawksbill Ln, Summerland Key, FL 33042
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  /33

  $249,000

  $30K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area. The home is clean and well cared for, offering a functional layout appropriate for full-time

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
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  /71

  $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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  /12

  $495,000

  • Land
  • 2,078 Sq Ft
  • $10,376,420 per Acre

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

  Anay Ramos Miami New Realty

  701 Spanish Main Dr Unit 84, Cudjoe 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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  /50

  $289,000

  • 1 Bed
  • 1 Bath
  • 340 Sq Ft

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

  Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
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  /65

  $3,695,000

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  24348 Caribbean Dr W, Summerland Key, FL 33042

  A stunning location with all attributes geared to the view of the beautiful open bay of Summerland Cove. This OCEANFRONT 3 bedroom 3 bath home is on the market for the first time since construction in 1996 and features an extensive renovation nearly complete. The property includes a stunning covered & heated pool with screened enclosure, a 28 foot concrete dock with davits, deep water boating

  Caroline Bauer Key West Sales, LLC

  24348 Caribbean Dr W, Summerland Key, FL 33042
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  /47

  $5,390,000

  $1M 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

  $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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  /55

  $1,650,000

  $150K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1163 de Lussan Ln, Summerland Key, FL 33042

  Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift

  Jan Fritz Coldwell Banker Schmitt RE Co.

  1163 de Lussan Ln, Summerland 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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  /125

  $10,499,000

  New Construction $501K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 4,894 Sq Ft

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

  Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress— built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
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  /75

  $875,000

  $64K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

  This is the house for your boat! Priced to sell! ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront home. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
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  /38

  $1,349,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  335 Pirates Rd, Summerland Key, FL 33042

  *SWIMMING POOL TO BE BUILT IN SUMMER OF 2026*Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true for

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  335 Pirates Rd, Summerland Key, FL 33042
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  /46

  $399,900

  $19K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 833 Sq Ft

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

  This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
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  /2

  $1,700,000

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  2211 San Sebastian Dr, Big Pine Key, FL 33043

  Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled

  Greg MacLaren Internet Realty of the Florida Keys

  2211 San Sebastian Dr, Big Pine Key, FL 33043
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  /56

  $579,900

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

  Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
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  /72

  $1,350,000

  • 5 Beds
  • 5 Baths
  • 2,258 Sq Ft

  4049 Egret Ln, Summerland Key, FL 33042

  Waterfront living meets comfort and functionality in this move-in ready canal front home. Offering 120 feet of concrete dockage in a deep water canal. Quick boating access to Niles Channel. Designed for the ultimate Florida Keys lifestyle, this property combines spacious indoor living with exceptional outdoor entertaining areas. The main home features 2 bedrooms and 2 bathrooms with an

  Deni Heintzelman KeyIsle Realty

  4049 Egret Ln, Summerland Key, FL 33042
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  /30

  $430,000

  $67K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
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  /25

  $569,700

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

  Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
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  /35

  $1,299,000

  • 3 Beds
  • 3 Baths
  • 1,774 Sq Ft

  30525 Winifred St, Big Pine Key, FL 33043

  Nestled in the heart of Big Pine Key, this private canal-front retreat with screened in POOL offers the perfect blend of comfort, space, and island living. Situated on an oversized 21,438 fenced in corner lot with a private gated entrance, the property provides exceptional privacy and a peaceful setting surrounded by tropical beauty. Plenty of space for your RV, Boat Trailer and more. It's a

  Joyce Craul Expert Realty LLC (HQ)

  30525 Winifred St, Big Pine Key, FL 33043
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  /46

  $487,000

  $88K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

  Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key—a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
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  /73

  $1,599,000

  • 3 Beds
  • 3.5 Baths
  • 2,295 Sq Ft

  1136 W Shore Dr, Big Pine Key, FL 33043

  Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking

  Beata Sharpe Coldwell Banker Vanguard Realty

  1136 W Shore Dr, Big Pine Key, FL 33043
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  /21

  $575,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

  Affordable piece of paradise! Fully furnished, move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. All new furnishings included! It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
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  /27

  $375,000

  • 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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  /19

  $1,750,000

  New Construction $250K PRICE INCREASE

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

  29558 Ranger Ave, Big Pine Key, FL 33043

  Experience the Ultimate Keys Lifestyle - New Construction with 75' of Waterfront on a Wide Boating CanalComing Fall 2025 - Nestled on a spacious 7,500 sqft lot (75x100) along a deep, wide boating canal, this brand new 1,500 sqft home offers the perfect blend of modern coastal living and exceptional boating access. With quick entry to Pine Channel, you're just minutes from both the Atlantic Ocean

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  29558 Ranger Ave, Big Pine Key, FL 33043
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  /61

  $2,700,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  1553 Sunrise Dr, Big Pine Key, FL 33043

  Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large Porcelain floors and counter tops enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Four roomy suites

  Barbara Eads Barbara Eads Realty Inc.

  1553 Sunrise Dr, Big Pine Key, FL 33043
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  /61

  $3,750,000

  New Construction

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

  17387 E Dolphin St, Sugarloaf Key, FL 33042

  Welcome to Morning Glory - The Dolphin House There are homes you visit... and there are homes you feel the moment you arrive. Morning Glory - The Dolphin House is one of those rare oceanfront sanctuaries where time softens, stress fades, and every sunrise feels like it was created just for you. Perfectly positioned on an oversized direct oceanfront lot, this extraordinary 4-bedroom, 3.5-bathroom

  Lela Ashkarian Coldwell Banker Schmitt Real Estate Co.

  17387 E Dolphin St, Sugarloaf Key, FL 33042
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  $1,595,000

  $344K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  16640 Cypress Rd, Summerland Key, FL 33042

  RARE Solar-Powered Waterfront Tropical Gem with TESLA Solar Storage Banks on Prestigious Sugarloaf Key! A rare opportunity to own a fully solar-powered waterfront residence featuring 26 solar panels and two Tesla Solar Powerwall storage banks, offering exceptionally low energy costs, backup power, and the potential to earn credits by supplying excess energy back to the grid. This elevated 3 BD, 2

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  16640 Cypress Rd, Summerland Key, FL 33042
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  /43

  $4,500,000

  • 2 Beds
  • 2 Baths
  • 1,467 Sq Ft

  4670 Dorn Rd, Summerland Key, FL 33042

  Discover a rare offering in the Florida Keys--an exceptional 2.84-acre waterfront estate on Big Torch Key, where serenity, seclusion, and world-class boating converge. Gracefully positioned on a coveted point lot, this remarkable property delivers sweeping open-water views, a private beach with boat launch, and protected dockage, offering an unparalleled coastal lifestyle.From sunrise to sunset,

  Sharon Davison Keller Williams Key West Compass Realty

  4670 Dorn Rd, Summerland Key, FL 33042

Showing Results 41 - 71, Page 2 of 2