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Summerland Key, FL Homes for Sale with Garage

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  • /62

    $5,200,000

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

    17013 Coral Dr, Sugarloaf 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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17013 Coral Dr, Sugarloaf Key, FL 33042
  • /61

    $1,399,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,372 Sq Ft

    21012 6th Ave, Summerland Key, FL 33042

    Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21012 6th Ave, Summerland Key, FL 33042
  • /52

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    29534 Geraldine St, Big Pine Key, FL 33043

    Turnkey and move-in ready, this exceptional waterfront home is being offered fully furnished--including furniture, dishes, cookware, and linens--so you can start enjoying the Florida Keys lifestyle from day one. Situated on an oversized 18,000 sq. ft. double lot with 150' of canal frontage in a quiet, peaceful Big Pine Key boating community, this solid concrete 3BD/2BA home features a desirable

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    Sandra Tuttle

    Island Welcome Real Estate

    29534 Geraldine St, Big Pine Key, FL 33043
  • /51

    $2,499,000

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

    27348 Dominica Ln, Ramrod Key, FL 33042

    Welcome to your waterfront retreat on Ramrod Key, where beautiful open water views, quick ocean access, and exceptional outdoor living create the ultimate Florida Keys lifestyle. Built by renowned Tom Ryan in 2007, this well-maintained 3-bedroom, 2-bath home is designed for both relaxation and adventure. Step inside to a bright, open-concept living area featuring a spacious kitchen with ample

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    27348 Dominica Ln, Ramrod Key, FL 33042
  • /68

    $3,199,000

    • 3 Beds
    • 3 Baths
    • 1,586 Sq Ft

    1148 Big Pine Ave, Big Pine Key, FL 33043

    If you've been dreaming of the kind of place where the sunsets stop you in your tracks...this is it. Tucked away on a quiet road in Big Pine Key, this 2 Bedroom 2 Bath plus 1 Bedroom 1 Bath Guest Cottage one-of-a-kind point property delivers something incredibly rare in the Florida Keys, open water views and protected dockage, all wrapped into a private tropical setting on over an acre and a

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1148 Big Pine Ave, Big Pine Key, FL 33043
  • /37

    $725,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    29160 Primrose Ln, Big Pine Key, FL 33043

    Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key. Featuring a garage and tons of storage inside and out, fenced yard & room for a pool! Inside you will find 3BR, 2 updated baths and a smart layout with an open concept living. Step outside to a beautiful covered porch the perfect spot to enjoy your morning coffee watching the

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    29160 Primrose Ln, Big Pine Key, FL 33043
  • /44

    $1,200,000

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

    17286 Jamaica Ln, Summerland Key, FL 33042

    Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, fishing, and the easygoing Keys lifestyle right at their doorstep. Set on a quiet street just 15 minutes from Key West, this sturdy concrete 2 bedroom, 2 bath home offers southern exposure overlooking the canal, quick access to

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17286 Jamaica Ln, Summerland Key, FL 33042
  • /76

    $1,550,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    29424 Forrestal Ave, Big Pine Key, FL 33043

    If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    29424 Forrestal Ave, Big Pine Key, FL 33043
  • /62

    $1,299,999

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    28560 Doubloon Rd, Summerland Key, FL 33042

    Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    28560 Doubloon Rd, Summerland Key, FL 33042
  • /63

    $3,100,000

    • 2 Beds
    • 3 Baths
    • 1,819 Sq Ft

    361 Avenue D, Summerland Key, FL 33042

    Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect blend of luxury, privacy, and island living. A charming thatched-covered lanai and custom bamboo-etched glass doors welcome you into an open-concept floor plan where floor to ceiling windows frame breathtaking Atlantic Ocean views.

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    Stacy Shahan

    Island Real Estate Company Florida Keys

    361 Avenue D, Summerland Key, FL 33042
  • /43

    $1,175,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,368 Sq Ft

    27395 Saint Lucie Ln, Summerland Key, FL 33042

    Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek Silestone countertops, and warm

    Agent Photo

    Michelle Vanhoose

    Coldwell Banker Schmitt Real Estate Co.

    27395 Saint Lucie Ln, Summerland Key, FL 33042
  • /27

    $1,055,000

    $110K PRICE DROP
    • 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

    Agent Photo

    Yvette Toledo-Baste

    COMPASS FLORIDA LLC

    29051 Magnolia Ln, Big Pine Key, FL 33043
  • /43

    $1,799,000

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

    51 Sawyer Dr, Cudjoe 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,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    51 Sawyer Dr, Cudjoe Key, FL 33042
  • /70

    $1,695,000

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    30463 Hawk Ln, Big Pine Key, FL 33043

    Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living. Outdoors, the home transforms into a

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    30463 Hawk Ln, Big Pine Key, FL 33043
  • /43

    $4,500,000

    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    4670 Dorn Rd, Summerland Key, FL 33042

    A must see to appreciate Boater's Paradise in the Lower Florida Keys. Experience a truly rare offering on Big Torch Key--an extraordinary 2.84-acre waterfront estate designed for the serious boater and those seeking complete seclusion. With over 1,000 feet of waterfront access on a premier point lot, this property delivers unmatched access, panoramic open-water views, and the ultimate in privacy.

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    Sharon Davison

    Keller Williams Key West Compass Realty

    4670 Dorn Rd, Summerland Key, FL 33042
  • /65

    $2,499,000

    • 4 Beds
    • 2 Baths
    • 2,739 Sq Ft

    21023 2nd Ave, Summerland Key, FL 33042

    Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21023 2nd Ave, Summerland Key, FL 33042
  • /43

    $1,850,000

    $151K PRICE INCREASE
    • 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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1607 Sunrise Dr, Big Pine Key, FL 33043
  • /145

    $16,900,000

    • 5 Beds
    • 4 Baths
    • 3,352 Sq Ft

    0 Howell Key Unit 620413, Summerland Key, FL 33042

    Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled opportunity to own an off-grid luxury island surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and refined coastal living, the island features acres of groomed

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    0 Howell Key Unit 620413, Summerland Key, FL 33042
  • /97

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    17151 Marlin Dr, Sugarloaf Key, FL 33042

    This beautifully remodeled waterfront bungalow is nestled in the heart of Sugarloaf Shores ,one of the Lower Florida Keys' most desirable boating communities. Set on an expansive 12,500 sq ft lot surrounded by lush tropical landscaping, this elevated two-story home offers the perfect blend of privacy, comfort, and island charm. With 3 Bedrooms plus a Loft and 2 Bathrooms, the layout is

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17151 Marlin Dr, Sugarloaf Key, FL 33042
  • /88

    $2,900,000

    • 4 Beds
    • 2 Baths
    • 1,917 Sq Ft

    1044 Lagoon Dr, Summerland Key, FL 33042

    Welcome to an exceptional waterfront property on Summerland Key, where three contiguous canal-front lots create an expansive Florida Keys retreat. Situated on a combined property featuring 240' of concrete seawall, this unique offering is designed for boating enthusiasts and those seeking the ultimate island lifestyle. The 1,917 sq. ft. residence is built for peace of mind with impact windows and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1044 Lagoon Dr, Summerland Key, FL 33042
  • /42

    $763,000

    • 4 Beds
    • 2 Baths
    • 2,136 Sq Ft

    30374 Oleander Blvd, Big Pine Key, FL 33043

    If you want a spacious home with plenty of privacy, this property delivers. Set within a lushly landscaped 12,500 sq. ft. double lot, the 2,136 sq. ft. living area provides ample space for family and guests with 4-bedrooms, 2-baths, a family room, laundry room and additional room that could be a 5th bedroom. Refreshing colors complement the space, and the tasteful furnishings are included with

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    30374 Oleander Blvd, Big Pine Key, FL 33043
  • /71

    $2,795,000

    Open Sat 11AM - 1PM $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,913 Sq Ft

    20920 5th Ave W, Summerland Key, FL 33042

    Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

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    Miriam Novotny

    Compass Florida, LLC

    20920 5th Ave W, Summerland Key, FL 33042
  • /45

    $799,000

    $126K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    195 W Shore Dr, Summerland Key, FL 33042

    Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    195 W Shore Dr, Summerland Key, FL 33042
  • /70

    $2,800,000

    • 4 Beds
    • 3 Baths
    • 3,286 Sq Ft

    21640 Overseas Hwy, Summerland Key, FL 33042

    SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

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    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    21640 Overseas Hwy, Summerland Key, FL 33042
  • /4

    $1,050,000

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    27403 Antigua Ln, Summerland Key, FL 33042

    Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

    Sonia Petraitis Caffroni Capital Intl Realty LLC

    27403 Antigua Ln, Summerland Key, FL 33042
  • /20

    $550,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    27910 Porgie Path, Summerland Key, FL 33042

    Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

    Alexis Seldin Xcellence

    27910 Porgie Path, Summerland Key, FL 33042
  • /64

    $1,480,000

    New Construction $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    27433 Antigua Rd, Summerland Key, FL 33042

    NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and impact-rated windows &

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • /39

    $1,600,000

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    29667 Forrestal Ave, Big Pine Key, FL 33043

    LOOKING FOR A KEYS HOME WITH SOLID CONSTRUCTION? Check out this updated 3BD/2BA CBS home in desirable Pine Channel Estates, Big Pine Key -- just 30 miles from Key West and offering low-maintenance living at its finest. Step through the door into an open floor plan filled with natural light. Impact-resistant sliding glass doors blend indoor and outdoor living, while 32''x32'' porcelain tile runs

    Monika Rydzak eXp Realty LLC KW Branch

    29667 Forrestal Ave, Big Pine Key, FL 33043
  • /27

    $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 KeysThís 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
  • /60

    $2,699,999

    • 4 Beds
    • 2.5 Baths
    • 2,452 Sq Ft

    20833 4th Ave W, Cudjoe Key, FL 33042

    Welcome to one of Cudjoe Gardens' most desirable waterfront addressesBuilt in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and

    Diane Corliss Coldwell Banker Schmitt RE Co.

    20833 4th Ave W, Cudjoe Key, FL 33042
  • /66

    $2,795,000

    • 4 Beds
    • 5.5 Baths
    • 3,224 Sq Ft

    333 Indies Rd, Ramrod Key, FL 33042

    Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

    Greg MacLaren Internet Realty of the Florida Keys

    333 Indies Rd, Ramrod Key, FL 33042
  • /100

    $8,995,000

    $955K PRICE DROP
    • 6 Beds
    • 4.5 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 Berkshire Hathaway HomeServices Knight & Gardner Realty

    16750 Old State Road 4a, Summerland Key, FL 33042
  • /18

    $799,000

    • 3 Beds
    • 1 Bath
    • 1,043 Sq Ft

    550 Pine Ln, Big Pine Key, FL 33043

    This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof,

    Justyn Ewald Expert Realty LLC

    550 Pine Ln, Big Pine Key, FL 33043
  • /41

    $949,000

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    342 Spanish Main Dr, Summerland Key, FL 33042

    Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

    Monika Rydzak eXp Realty LLC KW Branch

    342 Spanish Main Dr, Summerland Key, FL 33042
  • /65

    $1,595,000

    • 3 Beds
    • 3 Baths
    • 2,022 Sq Ft

    887 Bay Dr, Summerland Key, FL 33042

    Priced at Current appraised value, this 3-bedroom, 3-bath concrete fortress on deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quick access to both the Gulf and Atlantic--just a 15-minute boat ride to open ocean--this home is a true boater's paradise. Additionally, enjoy Airstrip rights as part of the Summerland Airport community. Set on a generous 75' x

    Amy Hanson Realty Executives Florida Keys Summerland Branch

    887 Bay Dr, Summerland Key, FL 33042
  • /42

    $727,000

    $58K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,224 Sq Ft

    31033 Hibiscus Dr, Big Pine Key, FL 33043

    Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Or you may just want to demo the house and build your Keys Dream Home on two

    Karen Haack Coldwell Banker Schmitt RE Co.

    31033 Hibiscus Dr, Big Pine Key, FL 33043
  • /45

    $1,269,000

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

    116 Spanish Main Dr, Summerland Key, FL 33042

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

    Tina Fingerman Beaches MLS

    116 Spanish Main Dr, Summerland Key, FL 33042
  • /2

    $1,199,000

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    29662 Independence Ave, Big Pine Key, FL 33043

    Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining. Step outside to a seawall that leads

    29662 Independence Ave, Big Pine Key, FL 33043
  • /41

    $590,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042
  • /36

    $1,185,000

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    706 Caribbean Dr E, Summerland Key, FL 33042

    OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop,

    Donna Pezzi Keller Williams Key West Compass Realty

    706 Caribbean Dr E, Summerland Key, FL 33042

Showing Results 1 - 40, Page 1 of 2

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,150,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$910,000
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$911
Number of Homes for Sale
56
Last 12 months Home Sales
115
Months of Supply
5.80
Median List Price
$1,269,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
0%
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