197

Homes for Sale in 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
  • /59

    $549,000

    • 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
  • /29

    $899,000

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

    463 Lesrohde Dr, Ramrod Key, FL 33042

    Don't miss the chance to own this exceptional piece of paradise--schedule a private showing today!Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful

    Sarah Dolson Keller Williams Key West Compass Realty

    463 Lesrohde Dr, Ramrod 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
  • /39

    $995,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042

    Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath oceanfront home combines sleek design with comfort and quality craftsmanship. Step inside to discover 9ft ceilings, leather-finish granite countertops, and high-end finishes throughout. The home comes

    The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
  • /45

    $899,999

    • 3 Beds
    • 2 Baths
    • 950 Sq Ft

    23012 Snapper Ln, Summerland Key, FL 33042

    Welcome to 23012 Snapper Lane in Beautiful Cudjoe Key, FL.This Three (3) bedroom and Two (2) bathroom elevated, waterfront on a corner lot is the one you have been looking for, with a great price too!This home is built to last and has been meticulously cared for. Come bring your boat and sit back and enjoy your favorite beverage on this oversized backyard. Tons of storage for all your toys, and

    Bobby Coe RE/MAX Keys Connection (KW)

    23012 Snapper Ln, Summerland Key, FL 33042
  • /79

    $875,000

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    19512 Aztec St, Summerland Key, FL 33042

    Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    19512 Aztec St, Summerland Key, FL 33042
  • /17

    $998,000

    • 3 Beds
    • 3 Baths
    • 1,400 Sq Ft

    17171 Seagrape Ln, Summerland Key, FL 33042

    RARE OPPORTUNITY HERE! This home is perfect for a DIY or Builder. Bring your imagination as it's located in very desirable location of Sugarloaf Shores where homes are over 2++ million dollars. It just needs a makeover but has great bones and many things you won't get now. Full 2 car garage with impact doors and shop. Legal downstairs bath. Large lot on 70' wide flow through canal. Bay views.

    Marie Howe Century 21 Circle - Key West

    17171 Seagrape Ln, Summerland Key, FL 33042
  • /4

    $195,000

    • Land

    Lot 2 Overseas Hwy, Summerland Key, FL 33042

    Partially cleared, commercial lot with 100' of frontage on Overseas Highway. Highly visible, high traffic location on Cudjoe Key. Accessible from La Fitte Dr. The partially cleared lot is zoned Suburban Commercial with many possible uses (see attached document for full list of potential land use). Buyer to verify use with county.

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

    Lot 2 Overseas Hwy, Summerland Key, FL 33042
  • /60

    $949,900

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    27405 Guadaloupe Ln, Summerland Key, FL 33042

    Soak up the Keys lifestyle from this bright, modern 3-bed/2-bath home in the coveted oceanside community of Breezeswept Beach Estates on Ramrod Key. Built in 2008 with high-end finishes--sleek cabinetry, quality flooring, and fresh, airy decor--this turnkey residence is neat, clean, and move-in ready.Outdoor living shines here: two open decks (front and back) capture breezes and sunset glow,

    Mark Gable Engel & Volkers Marathon

    27405 Guadaloupe Ln, Summerland Key, FL 33042
  • /19

    $475,000

    • 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
  • /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
  • /29

    $925,000

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

    17245 Jamaica Ln, Summerland Key, FL 33042

    Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life--paddleboarding, kayaking, the iconic jumping bridge, and world-class cycling right out your door. Set on a generous lot, this elevated 3-bedroom, 2-bath home blends laid-back island charm with modern

    Team Kaufelt Truman & Co. (KW)

    17245 Jamaica Ln, Summerland Key, FL 33042
  • /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
  • /18

    $470,000

    • Land

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

    Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
  • /2

    $56,000

    • Land
    • 0.26 Acre
    • $217,064 per Acre

    0 State Rd Unit 4A, Little Torch Key, FL 33042

    ROGO land dedication lot worth 2 points with paperwork completed and Monroe County letter of eligibility on file. No hidden expenses with this lot. Cost-effective way to get your permit faster! This lot is not buildable and is sold for land dedication purposes only.

    Nate Meyer Meyer and Boumerhi Realty LLC

    0 State Rd Unit 4A, Little Torch Key, FL 33042
  • /26

    $1,180,000

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

    27350 Barbados Ln, Ramrod Key, FL 33042

    Welcome to your slice of paradise in the Lower Florida Keys! This beautifully maintained 3-bedroom, 2-bath canal-front home offers everything you need for island living -- whether you're looking for a full-time residence, vacation getaway, or investment property. Nestled on a spacious 6,000 sq ft lot, this home boasts: - Direct Canal Access - Ideal for boaters! Navigate easily to open water.

    Jonathan Minerick Homecoin.com

    27350 Barbados Ln, Ramrod Key, FL 33042
  • /56

    $6,995,000

    • 5 Beds
    • 6 Baths
    • 3,952 Sq Ft

    1151 Ocean Dr, Summerland Key, FL 33042

    This luxe, oceanfront estate will be sold at Luxury AUCTION Without Reserve on December 4, 2025! List price for REFERENCE ONLY. Offered in co-op. with Platinum Luxury Auctions. Inquire for details.Trophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by multi million dollar estates favored by celebrities and business leaders. Fly in and boat out! Located in one of

    Lisa Swanson The Agency Florida Keys

    1151 Ocean Dr, Summerland Key, FL 33042
  • /88

    $750,000

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

    40 Munson Ave, Summerland Key, FL 33042

    Welcome home to your peaceful island retreat! This stunning 3-bed, 2-bath home is move-in ready & full of charm. Enjoy soaring vaulted ceilings, an open layout, & a bright kitchen with Quartz countertops, stainless steel appliances, & large island with ample seating. Recent updates include new luxury vinyl plank flooring, new upgraded refrigerator, & new outdoor bar & sitting area perfect for

    Lindsay Ryan EXP Realty LLC

    40 Munson Ave, Summerland Key, FL 33042
  • /3

    $64,750

    • Land

    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

    ROGO Lot. Letter on hand from Monroe County granting 2 points

    Jenna Stauffer Ocean Sotheby's International Realty

    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
  • /12

    $599,000

    • Land
    • 0.27 Acre
    • $2,183,468 per Acre

    16841 Driftwood Ln, Sugarloaf Shores, FL 33042

    **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

    Daiane Sardinas Carvalho Centennial Realty Group, LLC

    16841 Driftwood Ln, Sugarloaf Shores, FL 33042
  • /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
  • /2

    $379,000

    • Land

    27463 Antigua Rd, Ramrod Key, FL 33042

    Exceptional Opportunity to develop this 6200-sf canal front Ramrod Key Lot with Plans in the super relaxed Breezeswept Beach Estates community! Ideal Tier 3 Canal. Currently has 38 Rogo points and plans for an exceptional home, dock, and lift. Building Permit application is finalized and approved. 3/2 elevated home that is a certified green build. Just need Rogo award. Great Open water ocean

    Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

    27463 Antigua Rd, Ramrod Key, FL 33042
  • /55

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft

    20844 4th Ave W, Summerland Key, FL 33042

    Welcome to 20844 4th Ave W, a remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up one of the two brick paver driveways on this over sized lot you will find two entrances, beautiful landscaping and tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning concrete residence blends timeless elegance with coastal

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • /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
  • /17

    $265,000

    • Land

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

    Spacious RV lot measuring approximately 35 x 69 in the highly desirable Venture Out Resort on Cudjoe Key. This ROGO exempt lot is ready for your RV with both 30- and 50-amp service, water, and sewer hookups, plus the flexibility to build in the future. The community offers resort-style amenities including a heated pool, hot tub, private marina with boat ramp, fuel dock and community store,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
  • /14

    $265,000

    • Land

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out--golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /10

    $725,000

    • Land

    17220 Angelfish Ln, Sugarloaf Shores, FL 33042

    Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the

    The Spottswood Team Truman & Co. (KW)

    17220 Angelfish Ln, Sugarloaf Shores, FL 33042
  • /12

    $725,000

    • Land

    17230 Angelfish Ln, Sugarloaf Shores, FL 33042

    Build Your Dream Home in Sugarloaf Shores! Don't miss this rare opportunity to own a waterfront lot in the desirable Sugarloaf Shores! This high and dry, cleared 8,165 sq. ft. parcel offers a fresh canvas for your vision of paradise in the Florida Keys. The property features a brand-new concrete seawall, perfect for the boating enthusiast, with direct access to both the Atlantic Ocean and the

    The Spottswood Team Truman & Co. (KW)

    17230 Angelfish Ln, Sugarloaf Shores, 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
  • /98

    $2,800,000

    • 3 Beds
    • 3 Baths
    • 3,013 Sq Ft

    680 Cruikshank Island, Summerland Key, FL 33042

    Welcome to 680 Cruikshank Isle, an extraordinary waterfront estate in the heart of Summerland Key that captures the essence of Florida Keys luxury living. Offering over 3,000 sq. ft. of interior space, this three-bedroom, three-bath residence is thoughtfully designed for both elegance and comfort, blending open living areas with timeless architectural details.Inside, soaring ceilings and

    Barbara Crespo Keller Williams Key West Compass Realty

    680 Cruikshank Island, Summerland Key, FL 33042
  • /61

    $949,900

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    27332 St Martin Ln, Ramrod Key, FL 33042

    Welcome to Breezeswept Beach Estates-- In the heart of the Florida Keys! Here, boating, diving, and fishing are a way of life. This waterfront concrete block (CBS) 3-bed, 2-bath home sits on a deep, ocean-side canal just minutes to open water; Looe Key's clear blue reef is about a 15-minute boat ride away, and Key West is roughly 30 minutes by car. Thoughtfully updated for low-maintenance Keys

    Mark Gable Engel & Volkers Marathon

    27332 St Martin Ln, Ramrod Key, FL 33042
  • /14

    $299,000

    • Land

    27398 Jamaica Ln, Ramrod Key, FL 33042

    Great Location vacant lot with seawall and boat ramp. Minutes to Open Water. Just waiting for a perfect home. This is a great option to purchase 231 W. Indies Open Water Home and have great boating with this lot.Please look at MLS616482

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    27398 Jamaica Ln, Ramrod Key, FL 33042
  • /62

    $1,049,000

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft

    231 W Indies Dr, Summerland Key, FL 33042

    Welcome to your open-water paradise! This 3-bedroom, 2-bath home is all about embracing the Florida lifestyle. Wake up to breathtaking open-water sunrises while you sip coffee on your private balcony, then spend your afternoons lounging by the sparkling pool. The main level offers two comfortable bedrooms and a full bath -- perfect for family or guests -- while the entire second floor is your

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    231 W Indies Dr, Summerland Key, FL 33042
  • /49

    $910,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    813 Hawksbill Ln, Summerland Key, FL 33042

    Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board siding and a metal roof, this three-story retreat of island living. with GENERAC Generator. Inside, you'll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly

    Miguel Solis Douglas Elliman Florida, LLC - Sunset Drive

    813 Hawksbill Ln, Summerland Key, FL 33042
  • /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
  • /50

    $1,299,000

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft

    19749 Date Palm Dr, Summerland Key, FL 33042

    An incredible opportunity, especially for those looking for a spacious, 2464 sq ft well-equipped 12-foot stilted custom-built, waterfront home. 4 bedrooms, 3 baths plus a den with recent improvements and updates. Enormous Master bedroom and master bath with a gigantic tub. A huge breathtaking kitchen with stainless steel appliances. The combination of a large living area, open floor plan, modern

    Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

    19749 Date Palm Dr, Summerland Key, FL 33042
  • /39

    $650,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

    Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Main Dr in Cudjoe Key, FL. This beautiful property offers 2 bedrooms and 2 bathrooms within its 816 sq.ft. of finished living space. The home sits on a 2,568 sq.ft. lot, providing ample outdoor space for relaxing and entertaining. The property features a bright and airy interior with an open floor plan,

    Randal Longo Keys Realty Redefined LLC

    701 Spanish Main Dr Unit 495, Cudjoe 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
  • /45

    $7,000,000

    • 3 Beds
    • 4 Baths
    • 2,851 Sq Ft

    0 Melody Key Unit 616249, Summerland Key, FL 33042

    An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

    Scott Forman Royal Palms Realty (KW)

    0 Melody Key Unit 616249, Summerland Key, FL 33042

Showing Results 81 - 120, Page 3 of 5

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