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Summerland Key, FL Homes for Sale

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  • /31

    $749,500

    • 3 Beds
    • 1 Bath
    • 1,562 Sq Ft

    360 W Shore Dr, Summerland Key, FL 33042

    Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

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    Brenda Thomas

    Island Welcome Real Estate

    (786) 949-3594

    360 W Shore Dr, Summerland Key, FL 33042
  • /79

    $607,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    1258 Division St, Big Pine Key, FL 33043

    Welcome to Your Own Slice of Island Paradise in Big Pine Key! Tucked away in the heart of Big Pine, this picture-perfect 3-bedroom, 1-bath home invites you to slow down, breathe deep, & truly enjoy island living. Set on an oversized double lot totaling 12,500 sq ft, this property is truly a private tropical sanctuary: lush, peaceful, and full of life.From the moment you step inside, soaring beam

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    Lindsay Ryan

    EXP Realty LLC

    (833) 721-7372

    1258 Division St, Big Pine Key, FL 33043
  • /30

    $750,000

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

    26868 Mariposa Rd, Ramrod Key, FL 33042

    Presenting a newly built 2023 home on a spacious 12,250 sq. ft. lot in Ramrod Shores, designed with both efficiency and style in mind. This four-bedroom, two-bathroom property features durable construction elements like a metal roof and impact-resistant windows, optimizing insurance costs, with all 3 insurances combined under $5,000 total. The interior boasts an open-concept floor plan with high

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    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (786) 783-4956

    26868 Mariposa Rd, Ramrod Key, FL 33042
  • /41

    $1,899,000

    • 3 Beds
    • 3 Baths
    • 1,998 Sq Ft

    28573 Le Grand Rd, Little Torch Key, FL 33042

    This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 527-2862

    28573 Le Grand Rd, Little Torch Key, FL 33042
  • /49

    $698,800

    • 3 Beds
    • 2 Baths
    • 1,039 Sq Ft

    29048 Iris Dr, Big Pine Key, FL 33043

    50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water heater,

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 974-5892

    29048 Iris Dr, Big Pine Key, FL 33043
  • /10

    $499,000

    • Land

    63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (305) 834-4054

    63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
  • /38

    $698,000

    • 2 Beds
    • 2 Baths
    • 1,497 Sq Ft

    30416 Coconut Hwy, Big Pine Key, FL 33043

    Looking for a lot of land in the Keys, and a well-maintained home? This rare 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV, boat trailers, so much more! Over 1/2 acre, the 4 lots are bordered by Coconut Hwy. to the north, Avenue B to the west, and Hibiscus Ln. to the south from which vehicles can access the large, fenced portion of the back yard. Step inside

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 608-1417

    30416 Coconut Hwy, Big Pine Key, FL 33043
  • /80

    $985,000

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

    21855 Spain Blvd, Summerland Key, FL 33042

    Situated on a secluded acre just 20 minutes from Key West, this 3-bedroom, 2-bath pool home is surrounded by a botanical garden of impressive plantings including rare palm trees, buttonwoods, orchids, dragon fruit cactus, fragrant Joe wood, a Valencia Pride Mango tree. The custom-built, 1467 sq. ft., 3-bedroom, 2-bath CBS/frame home offers island charm with pineapple railings and multiple

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 225-2722

    21855 Spain Blvd, Summerland Key, FL 33042
  • /27

    $1,055,000

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

    29051 Magnolia Ln, Big Pine Key, FL 33043

    Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers an exceptional opportunity to enjoy the relaxed Lower Florida Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with

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    Yvette Toledo-Baste

    COMPASS FLORIDA LLC

    (855) 408-6871

    29051 Magnolia Ln, Big Pine Key, FL 33043
  • /50

    $1,385,000

    • 3 Beds
    • 2 Baths
    • 2,556 Sq Ft

    30830 Palm Dr, Big Pine Key, FL 33043

    Discover the perfect Florida Keys waterfront retreat in Big Pine Key. Situated on an oversized 16,779 sq ft lot on a quiet street away from the highway, this solidly built concrete block home with a concrete subfloor and stucco finish offers durability, privacy, and the laid-back island lifestyle buyers dream about.Boaters will appreciate 112 feet of concrete seawall, a 10,000 lb boat lift, and

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    Christopher Tanaka

    Coldwell Banker Schmitt RE Co.

    (855) 640-6438

    30830 Palm Dr, Big Pine Key, FL 33043
  • /43

    $949,000

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

    25057 7th St, Summerland Key, FL 33042

    Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the added bonus of a natural windbreak and guaranteed

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    Christopher Tanaka

    Coldwell Banker Schmitt RE Co.

    (786) 869-2251

    25057 7th St, Summerland Key, FL 33042
  • /31

    $725,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    27448 Haiti Ln, Ramrod Key, FL 33042

    Claim your slice of paradise and build the waterfront setup you've always wanted. Welcome to 27438 Haiti Ln, a deep-water canal-front blank canvas on Ramrod Key designed for the serious angler. This isn't just a home; it's the ultimate staging ground for your offshore and backcountry adventures.The highlight? A pristine shoreline ready for you to design and permit your dream dock. Whether you

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    Brenda Thomas

    Island Welcome Real Estate

    (645) 225-2680

    27448 Haiti Ln, Ramrod Key, FL 33042
  • /30

    $975,000

    • 3 Beds
    • 3 Baths
    • 1,492 Sq Ft

    31490 Avenue F, Big Pine Key, FL 33043

    This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and functionality. Featuring impact windows and doors and a durable metal roof, this home provides peace of mind and protection for years to come. The open-concept living area is perfect for both relaxation and entertaining, with a modern kitchen boasting quartz countertops and stainless steel appliances. The

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    Austin Kimbler

    Expert Realty LLC (HQ)

    (833) 691-1620

    31490 Avenue F, Big Pine Key, FL 33043
  • /44

    $1,199,000

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

    30329 Heron Ln, Big Pine Key, FL 33043

    Nature Lover's Waterfront Retreat on a Rare Double Canal Lot. Imagine living where the sky blazes with sunsets over a pristine bird sanctuary and gentle Key Deer roam freely through your yard. Welcome to 30329 Heron Lane, a beautifully maintained 3 bedroom, 2 bathroom elevated Conch Cottage perched on a 15,438 sq ft double corner canal lot with 268' of waterfront in Big Pine Key. From the moment

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 665-8962

    30329 Heron Ln, Big Pine Key, FL 33043
  • /39

    $1,399,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    51 Drost Dr, Summerland Key, FL 33042

    Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 551-4933

    51 Drost Dr, Summerland Key, FL 33042
  • /43

    $1,799,000

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

    51 Sawyer Dr, Summerland Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 970-3222

    51 Sawyer Dr, Summerland Key, FL 33042
  • /42

    $815,000 Open House 3/28

    • 2 Beds
    • 2 Baths
    • 936 Sq Ft

    29183 Cedar Dr, Big Pine Key, FL 33043

    This terrific canal-front home is situated on a fenced, low-maintenance 5,000 sq. ft. lot with 50 ft. concrete seawall and boat lift. The 50 ft. wide canal provides excellent access to the ocean and back-country with only one neighborhood bridge to go under (approx.. 10.5 ft. clearance.) Well-maintained and enjoyed by the owner for many years, it offers Hardi-board siding upstairs, a great

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (866) 382-4166

    29183 Cedar Dr, Big Pine Key, FL 33043
  • /74

    $2,999,000

    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft

    17041 Marlin Dr, Summerland Key, FL 33042

    Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (305) 809-8894

    17041 Marlin Dr, Summerland Key, FL 33042
  • /50

    $1,600,000

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

    947 Gulf Dr, Summerland Key, FL 33042

    There's a certain feeling you get the moment you pull onto Summerland Cove Isle, quiet, breezy, and unmistakably upscale. The kind of street where every home has been cared for, every canal sparkles, and the water itself seems to move with purpose. This home sits on the most coveted stretch of the island, where the flow-through, crystal-clear, extra-deep canals are the heartbeat of the

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    Coby Taylor

    Taylor & Assoc. RE, Inc.

    (786) 983-9115

    947 Gulf Dr, Summerland Key, FL 33042
  • /4

    $285,000

    • Land

    Unlisted Address

    Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

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    Coby Taylor

    Taylor & Assoc. RE, Inc.

    (786) 876-6382

    Unlisted Address
  • /50

    $1,499,000

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    21250 Conch Dr, Summerland Key, FL 33042

    Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 614-3802

    21250 Conch Dr, Summerland Key, FL 33042
  • /81

    $999,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    22852 Buccaneer Ln, Summerland Key, FL 33042

    Experience true Keys living in this beautifully renovated waterfront home located in desirable Cudjoe Key -- just minutes from local favorites like Square Grouper, 420 Lounge, and The Morning Joint.Enjoy excellent boating access with a concrete dock and a 10,000 lb boat lift, making this property ideal for serious boaters.One of the standout features of this home is its privacy. The neighboring

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    Austin Kimbler

    Expert Realty LLC (HQ)

    (645) 220-0519

    22852 Buccaneer Ln, Summerland Key, FL 33042
  • /8

    $120,000

    • Land

    Lot 6 Vacant Land, Big Pine Key, FL 33043

    Positioned just off US-1 (Jimmy Buffett Memorial Highway), this parcel of land benefits from excellent visibility and accessibility, supporting a wide variety of potential commercial uses.Potential for securing valuable ROGO points for future permitting needs in Monroe County (buyer to verify the number of ROGO points with the County).

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    Austin Kimbler

    Expert Realty LLC (HQ)

    (833) 721-5033

    Lot 6 Vacant Land, Big Pine Key, FL 33043
  • /49

    $2,699,000

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

    1233 Avenue A, Big Pine Key, FL 33043

    Tucked away on 2 gated acres along the pristine waters of Bogie Channel, Dei Paradiso is a one-of-a-kind open water estate offering total privacy, resort-style amenities, and world-class boating access to both the ocean and backcountry. Just a mile off the Overseas Highway, peace and convenience converge in this tropical retreat. Awaken to dazzling sunrises and wind down beneath the glow of

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 450-0019

    1233 Avenue A, Big Pine Key, FL 33043
  • /61

    $615,000

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft

    29951 Pine Channel Rd, Big Pine Key, FL 33043

    *Back on Market & Ready for New Owners!* VA Assumable 2.625% interest rate for eligible Buyers! Total current payment $2864/mo! Inquire for more details.Welcome to your island escape! This beautifully updated 2 bedroom, 2 full bath stilted home offers the perfect blend of comfort, convenience, & coastal charm. Situated on a spacious lot in the heart of Big Pine Key, this property features a brand

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    Lindsay Ryan

    EXP Realty LLC

    (877) 412-3188

    29951 Pine Channel Rd, Big Pine Key, FL 33043
  • /28

    $300,000

    • Land

    21865 Spain Blvd, Summerland Key, FL 33042

    Own 2.3 acres in Cudjoe Acres! Enjoy your own quiet piece of paradise with native vegetation, natural pond with wading birds, sheds, covered structures, a couple of cisterns and even a chicken coop. Parcel V fronts on a road with two gates on east side; Parcel W is accessed from Spain Blvd. and the two are connected by a private drive through the property. This property does not have a home on

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 225-1801

    21865 Spain Blvd, Summerland Key, FL 33042
  • /29

    $1,325,000

    • 3 Beds
    • 2 Baths
    • 1,494 Sq Ft

    22974 Anne Bonny Ln, Summerland Key, FL 33042

    Welcome to 22974 Anne Bonny Lane in Cudjoe Key, a beautifully appointed, turn-key waterfront home designed for island living and ready for immediate enjoyment--whether as a full-time residence, second home, or income-producing vacation rental. Perfect 1031 opportunity! This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago,

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 869-3656

    22974 Anne Bonny Ln, Summerland Key, FL 33042
  • /43

    $1,699,000

    • 2 Beds
    • 2 Baths
    • 1,980 Sq Ft

    1607 Sunrise Dr, Big Pine Key, FL 33043

    Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 301-2387

    1607 Sunrise Dr, Big Pine Key, FL 33043
  • /39

    $485,000

    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

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    Ian Calderwood

    Bluescape Real Estate

    (786) 551-4336

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • /20

    $214,500

    • Land

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

    RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

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    Ian Calderwood

    Bluescape Real Estate

    (786) 418-4615

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
  • /71

    $1,395,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    16941 Driftwood Ln, Summerland Key, FL 33042

    There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

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    Coby Taylor

    Taylor & Assoc. RE, Inc.

    (855) 606-6133

    16941 Driftwood Ln, Summerland Key, FL 33042
  • /49

    $975,000 Open House 3/28

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    683 Blackbeard Rd, Summerland Key, FL 33042

    Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back-country within easy reach. The rooftop deck is a wonderful vantage point for panoramic neighborhood and water views. Nestled in mature vegetation, the one-owner, custom-built, board and batten cedar home has been well-maintained

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 982-0551

    683 Blackbeard Rd, Summerland Key, FL 33042
  • /71

    $1,349,000

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

    403 Indies Rd, Ramrod Key, FL 33042

    Private Ramrod Key Sanctuary with Sunset Views & Exceptional Boating Access.A rare find, spanning over a 15,000 sq ft, fully fenced lot, offering remarkable privacy, natural beauty, and spectacular sunrise and sunset views. The main home features expansive impact glass door systems in the front and rear, filling the living space with natural light and framing canal views, distant views of the

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 952-7871

    403 Indies Rd, Ramrod Key, FL 33042
  • /32

    $625,000

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    29961 Pine Channel Rd, Big Pine Key, FL 33043

    Welcome to your perfect Florida Keys getaway in the heart of Big Pine Key. This charming 2-bedroom, 1-bath home offers an inviting open-concept layout that flows seamlessly between the living, dining, and kitchen areas. Natural light pours in through large windows, creating a bright, airy feel that complements the relaxed island setting.The kitchen features stainless steel appliances and a

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    Terrance Sullivan

    Ocean Sotheby's International Realty

    (833) 583-1227

    29961 Pine Channel Rd, Big Pine Key, FL 33043
  • /48

    $1,399,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    823 Indies Rd, Ramrod Key, FL 33042

    Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (305) 614-6847

    823 Indies Rd, Ramrod Key, FL 33042
  • /62

    $5,200,000

    • 4 Beds
    • 4 Baths
    • 2,660 Sq Ft

    17013 Coral Dr, Summerland Key, FL 33042

    Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 882-3659

    17013 Coral Dr, Summerland Key, FL 33042
  • /58

    $3,750,000

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    755 Sawyer Dr, Summerland Key, FL 33042

    In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

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    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 204-2360

    755 Sawyer Dr, Summerland Key, FL 33042
  • /90

    $3,695,000

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    680 Elma Ave, Big Pine Key, FL 33043

    RARE west-facing private estate offering sunset views, owned bay bottom, and exceptional boating access. Welcome to Tarpon Cove, an exclusive retreat located in Big Pine Key, surrounded by the Florida Key Deer Preserve for unmatched privacy and natural beauty.The concrete residence has been meticulously reconstructed through a down-to-the-studs renovation, resulting in a 2023 effective age and is

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    Sandra Tuttle

    Island Welcome Real Estate

    (877) 359-5426

    680 Elma Ave, Big Pine Key, FL 33043
  • /29

    $839,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    22739 Buccaneer Ln, Summerland Key, FL 33042

    Welcome to Cudjoe Key - A prime location in the Lower Florida Keys. If you're looking for the ultimate ''Island Life'' this tropical canal-front home in sought-after Cutthroat Harbor Estates is exactly what you need. Perfectly positioned to embrace the laid-back Keys lifestyle, this property offers the ideal blend of waterfront living, privacy, and island charm. This 2 Bedroom 2 Bath home is

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    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 882-7259

    22739 Buccaneer Ln, Summerland Key, FL 33042
  • /71

    $525,000

    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall.* Community

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    Ian Calderwood

    Bluescape Real Estate

    (786) 977-2397

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

Showing Results 1 - 40, Page 1 of 8

Why Live in Summerland Key

Summerland Key delivers the quintessential Florida Keys lifestyle with a quieter, more laidback feel than nearby Key West, located about 25 miles away. This secluded Lower Keys community is known for its waterfront homes, deepwater canals and effortless access to boating, fishing and other nautical adventures. A private residential airport and Mote Marine Laboratory’s International Center for Coral Reef Research & Restoration add to its distinct character and local employment base. Homes are concentrated on the south side of the community, where many of the multi-level properties feature docks, boat lifts and pools. Tree-lined streets and lush tropical landscaping enhance curb appeal. Exclusive enclaves like Seven Palms Cove highlight the area’s appeal for high-end buyers and investors. With a median age of 58 and homeownership above 80%, Summerland Key attracts full-time residents as well as second-home owners. Outdoor recreation is central to life here, from boating and snorkeling to offshore and flats fishing. Nearby Bahia Honda State Park offers beaches and camping. Casual restaurants and a local seafood market complete the relaxed island lifestyle.

Frequently Asked Questions

What is the average home price in Summerland Key, FL?
Homes for sale in Summerland Key, FL have an average home price of $1,698,651.
Are home prices dropping in Summerland Key?
Yes, home prices in Summerland Key are down 10% in the last 12 months.
How many homes have sold over the last 12 months in Summerland Key, FL?
109 homes have sold in Summerland Key, FL over the last 12 months.
What are the most popular zip codes in Summerland Key, FL?
The most popular zip codes in Summerland Key, FL include 33042, 33043 and 33040.
How much do you need to make to afford a house in Summerland Key?
The median home price in Summerland Key is $1,300,000. If you put a 20% down payment of $260,000 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $6,380 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $273K a year to afford the median home price in Summerland Key. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Summerland Key, FL?
Summerland Key, FL has highly rated public and private schools. Some of the best schools in Summerland Key based on Niche Grades are Sugarloaf School and Key West High School. Browse all the schools in Summerland Key, FL to learn more.

Home Trends in Summerland Key, FL

Housing Trends

Median Sale Price
$1,116,000
Median Single Family Sale Price
$1,177,500
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$904
Number of Homes for Sale
67
Last 12 months Home Sales
109
Months of Supply
7.40
Median List Price
$1,300,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-6%
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