Homes for Sale in 33042

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  /28

  $1,950,000

  • 3 Beds
  • 3 Baths
  • 1,797 Sq Ft

  860 Lagoon Dr, Summerland Key, FL 33042

  This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThis home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

  Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  860 Lagoon Dr, Summerland Key, FL 33042
• 

  

  

  /65

  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  165 Cutlass Ln, Summerland Key, FL 33042

  Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

  Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
• 

  

  

  /50

  $2,500,000 New Construction

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

  711 W Indies Dr, Summerland Key, FL 33042

  Stunning Brand New Open Water CBS Construction Home on beautiful Ramrod Key, FL. Minutes to the Atlantic Ocean and World Famous Looe Key the #1 Dive destination in the Continental US.Discover coastal living at its finest with this brand-new 4-bedroom, 3-bathroom home nestled on the sparkling open waters of Ramrod Key. Boasting 2,000 square feet of thoughtfully designed living space, this home

  Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
• 

  

  

  /40

  $925,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large island

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28571 Buccaneer Rd, Summerland Key, FL 33042
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  /2

  $324,999

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement. The value of this property is in the ROGO EXEMPT status. All the utilities are there and I can give you clear title for this property upon closing. I have also determined that financing for this project is very difficult to obtain. A cash deal is the easiest way to make this deal work.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
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  /61

  $1,795,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  876 Gulf Dr, Summerland Key, FL 33042

  Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal

  Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
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  /2

  $115,000

  • Land
  • 1.27 Acres
  • $90,552 per Acre

  Lot 5 Mira Rd, Sugarloaf Key, FL 33042

  This lot is worth 4 points to be used towards obtaining a building permit in the ROGO system. Please contact Monroe County to verify information. Seller has several point lots for sale.

  Pamela Stangler Expert Realty LLC

  Lot 5 Mira Rd, Sugarloaf Key, FL 33042
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  /34

  $980,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  131 Doubloon Ln, Summerland Key, FL 33042

  3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024).The downstairs area includes two large storage rooms, one of which features a fully functioning

  Jenifer Hirsch Bluescape Real Estate

  131 Doubloon Ln, Summerland Key, FL 33042
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  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
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  /21

  $875,000

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

  27360 Saint Croix Ln, Summerland Key, FL 33042

  Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

  Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
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  /57

  $1,595,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  25368 2nd St, Summerland Key, FL 33042

  Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

  Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, FL 33042
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  /33

  $1,195,000

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

  17226 Jamaica Ln, Summerland Key, FL 33042

  Completely remodeled, turn key 3 bed 2 bath canal front home that.backs up to the nature's preserve. Home features large pool with a bar area and 300 square feet enclosed storage ,mature landscaping and concrete wall with automatic gate . Easy boating access from new concrete dock to Atlantic ocean side and the Gulf. Actively profitable Airbnb home

  Stephen Hachey

  17226 Jamaica Ln, Summerland Key, FL 33042
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  /9

  $3,500,000

  • Land

  19657 Seminole St, Sugarloaf Key, FL 33042

  Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

  Derek Epperly Engel & Volkers Key West

  19657 Seminole St, Sugarloaf Key, FL 33042
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  /60

  $2,499,000

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft

  556 Caribbean Dr E, Summerland Key, FL 33042

  The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
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  /24

  $875,000

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

  853 Indies Rd, Summerland Key, FL 33042

  Move right into this well-maintained 3-bedroom, 2-bath canal front home, built in 2006 and cared for with pride. The bright, open layout features a split floor plan that offers comfortable space for everyday living and entertaining.The primary bedroom includes an en-suite bath and a versatile bonus room -- ideal for a home office, nursery, or cozy retreat. Step outside to enjoy peaceful canal

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  853 Indies Rd, Summerland Key, FL 33042
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  /53

  $1,710,000

  • 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 exploring

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
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  /25

  $745,000

  • Land

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

  Barbara Eads Barbara Eads Realty

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042
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  /49

  $329,000

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
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  /15

  $644,500

  • Land

  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
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  /18

  $600,000

  • Land

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
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  /100

  $9,950,000

  • 6 Beds
  • 5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

  Lisa Swanson The Agency Florida Keys

  16750 Old State Road 4a, Summerland Key, FL 33042
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  /16

  $775,000

  • Land

  28597 Peg Leg Rd, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3809 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom four-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house. Open Water View. House Permit SF-DUP-2025-0111, 41.5

  Barbara Eads Barbara Eads Realty

  28597 Peg Leg Rd, Little Torch Key, FL 33042
• 

  

  /19

  $465,000

  • Land

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
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  /21

  $475,000

  • 1 Bed
  • 1 Bath
  • 668 Sq Ft

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

  Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
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  /9

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

  Robin Nilsson Keller Williams Key West Compass Realty

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /96

  $1,698,000

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft

  17176 Bonita Ln W, Summerland Key, FL 33042

  Experience island living in this 2,353 sq ft, 4-bed, 3-bath Sugarloaf Shores home on a 12,500 sq ft lot. The split-level design includes two ensuite bedrooms with balcony access, plus two guest rooms on the ground floor. Skylights brighten the open living areas, flowing seamlessly to a 44' screened balcony.Out back, enjoy a 22' x 10' pool, gazebo, private boat ramp, swim ladder, and dual lifts

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
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  /64

  $3,199,000

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

  Stacy Shahan Island Real Estate Company Florida Keys

  23941 Henry St, Summerland Key, FL 33042
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  /30

  $485,000

  • 2 Beds
  • 1.5 Baths
  • 604 Sq Ft

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
• 

  

  /9

  $185,000

  • Land

  Vacant Picard Ln, Cudjoe Key, FL 33042

  Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open

  Sunnie San Lorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  

  /11

  $650,000

  • Land

  775 Pirates Rd, Summerland Key, FL 33042

  Rare opportunity in Jolly Roger Estates on Little Torch Key. This 6,000 sq. ft. cleared and build-ready lot comes with two ROGO exemptions, allowing for immediate construction. The property features 60 feet of east-facing waterfront with a concrete dock, step-down, and davits already in place. Central sewer is connected. Located on a clean, deep canal (approx. 3 ft. control depth) with quick open

  Melissa Gibbins Expert Realty LLC (HQ)

  775 Pirates Rd, Summerland Key, FL 33042
• 

  

  /71

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft

  19881 Date Palm Dr, Summerland Key, FL 33042

  Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home is tucked away in a quiet, secluded location and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal!Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek

  Jimmy Lane Island Life Realty Experts

  19881 Date Palm Dr, Summerland Key, FL 33042
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  /39

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  21073 7th Ave, Summerland Key, FL 33042

  Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  21073 7th Ave, Summerland Key, FL 33042
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  /41

  $2,450,000

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft

  1176 Thatch Ln, Summerland Key, FL 33042

  Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

  Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  

  /42

  $2,200,000

  • 5 Beds
  • 3 Baths
  • 1,978 Sq Ft

  94 Sacarma Dr, Cudjoe Key, FL 33042

  Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

  Michelle Blades Realty Executives Florida Keys Old Town

  94 Sacarma Dr, Cudjoe Key, FL 33042
• 

  

  /24

  $995,000

  • Land
  • 5 Acres
  • $199,000 per Acre

  2231 Middle Torch Rd, Summerland Key, FL 33042

  Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential. The property currently features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each

  Stephany Duvall Engel & Volkers Marathon

  2231 Middle Torch Rd, Summerland Key, FL 33042
• 

  

  /16

  $250,000

  • Land

  LOT 12 Saint Lucie Ln, Ramrod Key, FL 33042

  Canalfront lot on Ramrod Key located in a desirable waterfront community oceanside between Key West and Marathon, offering quick access to the Atlantic Ocean then onto Florida Bay. No building permit is currently in place; buyers may apply through ROGO or purchase a separate building right.

  Karan Moeller Ocean Sotheby's International Realty

  LOT 12 Saint Lucie Ln, Ramrod Key, FL 33042
• 

  

  /7

  $4,325,000 New Construction

  • 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 Muzzillo Serhant Florida LLC - Delray Beach Office

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

  

  /18

  $3,999,999

  • 5 Beds
  • 5 Baths
  • 3,700 Sq Ft

  17229 Oleander Ln, Summerland Key, FL 33042

  Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home

  Justyn Ewald Expert Realty LLC (HQ)

  17229 Oleander Ln, Summerland Key, FL 33042
• 

  

  /55

  $2,299,999

  • 3 Beds
  • 3 Baths
  • 2,288 Sq Ft

  17210 Angelfish Ln, Summerland Key, FL 33042

  Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence offers 2,288 square feet of modern coastal comfort. Situated on an expansive 16,445-square-foot lot, the property features a private seawall for direct boating access and a sparkling pool perfect for relaxing after a day on the

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln, Summerland Key, FL 33042

Showing Results 81 - 120, Page 3 of 6