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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
  • /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
  • /11

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft

    744 Trinidad Ln, Summerland Key, FL 33042

    Positioned to capture beautiful open water views of Pine Channel, this property sits in a quiet neighborhood that blends privacy with convenience. Spanning6,000 sq ft, this lot offers a rare opportunity to secure space, flexibility, and open water views in the Lower Keys. Enjoy being just minutes from shopping, restaurants, nightlife, the nature park, and the Big Pine Community Park while

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 503-8190

    744 Trinidad Ln, Summerland Key, FL 33042
  • /48

    $675,000

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft

    31011 Avenue C, Big Pine Key, FL 33043

    This 4-bedroom, 2-bath, 1566 sq. ft. home in the Keys is a rare find for price! Features include a split bedroom floor plan, laundry room, a big sundeck, covered parking, ground-level storage enclosure, and convenient access from both Avenue C and Sands Rd. Local shops and amenities are nearby, with easy commutes to Marathon or Key West. The Big Pine Community Park, less than half a mile away,

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 856-6295

    31011 Avenue C, Big Pine Key, FL 33043
  • /34

    $1,275,000

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    1657 Watson Blvd, Big Pine Key, FL 33043

    Experience the keys waterfront lifestyle! This charming 3 bedroom, 2 bath home has peekaboo views of Big Pine Bight and is minutes away from Bogie Channel with NO limiting bridges to slow you down. Only 2 minutes to the Atlantic, and direct access to the Gulf. Equipped with a 10,000 LB boat lift, the boat is also available as a separate purchase. The buyer will get first right of refusal on the

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (833) 532-1578

    1657 Watson Blvd, Big Pine Key, FL 33043
  • /16

    $999,000

    • Land

    21082 6th Ave, Summerland Key, FL 33042

    An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (645) 300-6302

    21082 6th Ave, Summerland Key, FL 33042
  • /68

    $2,985,000

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

    23941 Henry St, Summerland Key, FL 33042

    Oceanfront retreat with sandy beach, protected dockage & direct access to the Ocean & Gulf.Wake each morning to breathtaking Atlantic sunrises and unwind beneath glowing sunsets in this custom-built, two-story CBS oceanfront home. Tucked away on a private street shared by only four residences, this exceptional island inspired sanctuary offers panoramic ocean views, unmatched privacy, and the

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    Stacy Shahan

    Island Real Estate Company Florida Keys

    (786) 686-4688

    23941 Henry St, Summerland Key, FL 33042
  • /66

    $539,000

    • 2 Beds
    • 2 Baths
    • 836 Sq Ft

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

    Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

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    Ian Calderwood

    Bluescape Real Estate

    (786) 882-1915

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • /58

    $3,750,000

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

    755 & 744 Sawyer Dr, Cudjoe 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

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    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 465-7217

    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
  • /62

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    28151 Helen Ave, Summerland Key, FL 33042

    Like new extra spacious open floor plan with efficient layout, ultra low insurances, and free public boat ramp nearby! This home features three large bedrooms and two full bathrooms with tiled showers, a huge eat-in stainless steel kitchen with room for an island or kitchen table, vinyl plank flooring throughout, all impact rated windows, metal roof, indoor laundry room, and spacious covered

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    Lindsay Ryan

    EXP Realty LLC

    (786) 952-7185

    28151 Helen Ave, Summerland Key, FL 33042
  • /49

    $799,000

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft

    1672 Pandorea Ln, Big Pine Key, FL 33043

    Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, an exceptional upgraded

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (888) 410-2419

    1672 Pandorea Ln, Big Pine Key, FL 33043
  • /43

    $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

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (866) 827-7154

    30374 Oleander Blvd, Big Pine Key, FL 33043
  • /35

    $599,000

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

    27940 Lobster Tail Trail, Summerland Key, FL 33042

    Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $625,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

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    Sandra Tuttle

    Island Welcome Real Estate

    (645) 218-8749

    27940 Lobster Tail Trail, Summerland Key, FL 33042
  • /44

    $2,295,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    937 Gulf Dr, Summerland Key, FL 33042

    High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout,

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    Sandra Tuttle

    Island Welcome Real Estate

    (645) 230-1994

    937 Gulf Dr, Summerland Key, FL 33042
  • /34

    $1,575,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    22865 Redfish Ln, Summerland Key, FL 33042

    The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

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    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 241-6029

    22865 Redfish Ln, Summerland Key, FL 33042
  • /38

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,203 Sq Ft

    153 Peg Leg Ln, Summerland Key, FL 33042

    Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 853-7147

    153 Peg Leg Ln, Summerland Key, FL 33042
  • /43

    $924,000

    • 3 Beds
    • 2 Baths
    • 1,036 Sq Ft

    420 W Indies Dr, Summerland Key, FL 33042

    Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (645) 666-1028

    420 W Indies Dr, Summerland Key, FL 33042
  • /72

    $2,995,000

    • 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

    (786) 667-5744

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

    $925,000

    • 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 998-8438

    195 W Shore Dr, Summerland Key, FL 33042
  • /73

    $3,500,000

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

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 841-9203

    1083 Labat Ln, Cudjoe Key, FL 33042
  • /27

    $987,500

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft

    3962 No Name Rd, Big Pine Key, FL 33043

    Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

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    Stacy Shahan

    Island Real Estate Company Florida Keys

    (888) 275-1086

    3962 No Name Rd, Big Pine Key, FL 33043
  • /12

    $789,900

    • Land

    0 Dominica Ln Unit 615842, Ramrod Key, FL 33042

    Gorgeous Open Ocean location totaling 4 lots, boasting over a quarter acre of land with sheltered canal and private beach; an incredible investment opportunity! Build your dream home in paradise with a transferable building right, which are readily available on the market and provide an easy path to development. This unique opportunity is in the ideal location, on one of the last remaining Open

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 744-6884

    0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
  • /22

    $679,000

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    19591 Navajo St, Summerland Key, FL 33042

    INDIAN MOUNDS SPECIAL!!!! Two balconies with ocean views and a hot tub to enjoy them with!!! Just one block from the private community boat ramp, this elevated 2 bed, 2 bath home sits on a large oversized corner lot. There is plenty of room for parking your toys and a downstairs enclosure for additional storage. Hardibacker siding and a metal roof provide peace of mind.Upon entering, you'll find

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    Mike Kane

    Internet Realty of the Florida Keys

    (645) 230-1301

    19591 Navajo St, Summerland Key, FL 33042
  • /36

    $750,000

    • Land
    • 9.26 Acres
    • $80,995 per Acre

    0 Niles Rd, Summerland Key, FL 33042

    Discover the perfect opportunity to build your dream home in the Lower Keys on this desirable parcel located on Summerland Key, FL. Set within a peaceful residential neighborhood, this property offers an inviting blend of tranquility and convenience—just minutes from US-1, local marinas, boat ramps, dining, beaches, and world-class fishing. Enjoy the relaxed island lifestyle, tropical breezes,

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    Javier Santana

    Sunland Real Estate, LLC.

    (786) 504-0768

    0 Niles Rd, Summerland Key, FL 33042
  • /53

    $1,195,000

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

    29534 Geraldine St, Big Pine Key, FL 33043

    Discover the perfect blend of island lifestyle and income potential in this well-appointed waterfront home located in a desirable Big Pine Key boating community with Commercial Fishing District zoning--a rare advantage allowing marine-based business use, boat storage, and added flexibility.Situated on a 18,000 sq ft double lot with 150' of canal frontage, this solid concrete, single-level home

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    Sandra Tuttle

    Island Welcome Real Estate

    (844) 697-1109

    29534 Geraldine St, Big Pine Key, FL 33043
  • /67

    $1,449,900

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    17215 Bonita Ln E, Summerland Key, FL 33042

    Completely reimagined and absolutely stunning, this beautifully remodeled home in Sugarloaf Shores showcases a full renovation, including a brand new dock. The beautiful 3 Bedroom 2 Bathroom home features commercial grade luxury vinyl floors, beautiful new finishes, custom cabinetry, new appliances, and fresh paint inside and out. Every detail was thoughtfully selected, creating a clean, modern

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 798-4569

    17215 Bonita Ln E, Summerland Key, FL 33042
  • /64

    $1,790,000

    • 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

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    Sandra Tuttle

    Island Welcome Real Estate

    (844) 795-0878

    30463 Hawk Ln, Big Pine Key, FL 33043
  • /16

    $1,200,000

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft

    715 Caribbean Dr E, Summerland Key, FL 33042

    Experience the ultimate Florida Keys lifestyle at 715 Caribbean Drive East in Summerland Key. Located in a desirable boating and aviation community, this property offers rare access to a private neighborhood airstrip, ideal for pilots and aviation enthusiasts. Designed for boaters, the home features a 60-foot dock and a 15,000-lb boat lift, providing easy access to open water, nearby sandbars,

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (844) 920-0831

    715 Caribbean Dr E, Summerland Key, FL 33042
  • /19

    $215,000

    • Land

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

    Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

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    Ian Calderwood

    Bluescape Real Estate

    (786) 761-5180

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • /39

    $1,499,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    20838 5th Ave W, Summerland Key, FL 33042

    Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 952-7261

    20838 5th Ave W, Summerland Key, FL 33042
  • /37

    $750,000

    • 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 key

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    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    (877) 521-8118

    29160 Primrose Ln, Big Pine Key, FL 33043
  • /60

    $487,500

    • 2 Beds
    • 1 Bath
    • 667 Sq Ft

    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

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    Ian Calderwood

    Bluescape Real Estate

    (786) 981-9841

    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
  • /66

    $799,000

    • 2 Beds
    • 2 Baths
    • 842 Sq Ft

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

    Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

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    Ian Calderwood

    Bluescape Real Estate

    (786) 841-6970

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
  • /65

    $3,999,000

    • 3 Beds
    • 3 Baths
    • 2,096 Sq Ft

    17015 Wahoo Ln W, Summerland Key, FL 33042

    Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 854-0770

    17015 Wahoo Ln W, Summerland Key, FL 33042
  • /26

    $1,225,000

    • 2 Beds
    • 2 Baths
    • 1,364 Sq Ft

    466 W Shore Dr, Summerland Key, FL 33042

    Welcome to 466 W Shore Dr in prestigious Summerland Key. This 2 bedroom concrete home is situated on a 12,000 sg foot lot, located on a wide deep water boating canal. There is an RV hookup, as well as power at the dock. And with 120' of concrete seawall, there is plenty of room for a large boat, or boats. The home is a split-bedroom and bathroom floor plan with beautiful terrazzo floors, updated

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (786) 686-3066

    466 W Shore Dr, Summerland Key, FL 33042
  • /63

    $1,325,000

    • 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

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    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 772-6030

    28560 Doubloon Rd, Summerland Key, FL 33042
  • /17

    $599,900

    • Land

    17215 Keystone Rd, Sugarloaf Shores, FL 33042

    Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 957-7959

    17215 Keystone Rd, Sugarloaf Shores, FL 33042
  • /27

    $630,000

    • 3 Beds
    • 2 Baths
    • 1,367 Sq Ft

    30350 Oleander Blvd, Big Pine Key, FL 33043

    Charming 3 Bedroom 2 Bathroom home in Big Pine Key, ready to welcome its next owners! Tucked away on a quiet street and surrounded by lush natural beauty, this property offers a peaceful and private setting. Inside, you will find a bright and spacious layout with abundant natural light flowing throughout the living areas. The kitchen is designed for both function and style, featuring a peninsula

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    Ryan Gernaat

    Coldwell Banker Schmitt Lower Keys (KW)

    (877) 318-9145

    30350 Oleander Blvd, Big Pine Key, FL 33043
  • /47

    $559,000 Open Fri 10:30AM - 1:30PM

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida 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 35 ft seawall.* Community Boat Ramp and boat washdown station.*

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    Ian Calderwood

    Bluescape Real Estate

    (786) 686-7983

    701 Spanish Main Dr Unit 510, 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 $1,702,192.
Are home prices dropping in Summerland Key?
Yes, home prices in Summerland Key are down 9% in the last 12 months.
How many homes have sold over the last 12 months in Summerland Key, FL?
110 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 6.38%, your estimated principal and interest payment would be $6,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $278K 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
$1,133,000
Median Single Family Sale Price
$1,170,000
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$909
Number of Homes for Sale
70
Last 12 months Home Sales
110
Months of Supply
7.60
Median List Price
$1,300,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-4%
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