243

Summerland Key, FL Homes for Sale

Section Image Section Image
  • 21023 2nd Ave, Summerland Key, FL 33042
    21023 2nd Ave, Summerland Key, FL 33042
    21023 2nd Ave, 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
  • 17013 Coral Dr, Sugarloaf Key, FL 33042
    17013 Coral Dr, Sugarloaf Key, FL 33042
    17013 Coral Dr, Sugarloaf Key, FL 33042
    /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
  • 1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    /69

    $3,300,000

    $200K PRICE DROP
    • 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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    1083 Labat Ln, Cudjoe Key, FL 33042
  • 21012 6th Ave, Summerland Key, FL 33042
    21012 6th Ave, Summerland Key, FL 33042
    21012 6th Ave, Summerland 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
  • 17015 Wahoo Ln W, Sugarloaf Key, FL 33042
    17015 Wahoo Ln W, Sugarloaf Key, FL 33042
    17015 Wahoo Ln W, Sugarloaf Key, FL 33042
    /72

    $3,899,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,096 Sq Ft

    17015 Wahoo Ln W, Sugarloaf 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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17015 Wahoo Ln W, Sugarloaf Key, FL 33042
  • 30463 Hawk Ln, Big Pine Key, FL 33043
    30463 Hawk Ln, Big Pine Key, FL 33043
    30463 Hawk Ln, Big Pine Key, FL 33043
    /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
  • 360 W Shore Dr, Summerland Key, FL 33042
    360 W Shore Dr, Summerland Key, FL 33042
    360 W Shore Dr, Summerland Key, FL 33042
    /30

    $749,500

    $46K PRICE DROP
    • 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

    Agent Photo

    Brenda Thomas

    Island Welcome Real Estate

    360 W Shore Dr, Summerland Key, FL 33042
  • 0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
    /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

    Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
  • 1607 Sunrise Dr, Big Pine Key, FL 33043
    1607 Sunrise Dr, Big Pine Key, FL 33043
    1607 Sunrise Dr, Big Pine Key, FL 33043
    /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
  • 701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    /39

    $485,000

    $10K PRICE DROP
    • 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.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • 0 Howell Key Unit 620413, Summerland Key, FL 33042
    0 Howell Key Unit 620413, Summerland Key, FL 33042
    0 Howell Key Unit 620413, Summerland Key, FL 33042
    /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 with two building rights, allowing for one additional residence, surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    0 Howell Key Unit 620413, Summerland Key, FL 33042
  • 16941 Driftwood Ln, Summerland Key, FL 33042
    16941 Driftwood Ln, Summerland Key, FL 33042
    16941 Driftwood Ln, Summerland Key, FL 33042
    /71

    $1,369,000

    $26K PRICE DROP
    • 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

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    16941 Driftwood Ln, Summerland Key, FL 33042
  • 29160 Primrose Ln, Big Pine Key, FL 33043
    29160 Primrose Ln, Big Pine Key, FL 33043
    29160 Primrose Ln, Big Pine Key, FL 33043
    /37

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    29160 Primrose Ln, Big Pine Key, FL 33043

    Welcome to Eden Pines--now offered at an exceptional new price of $700,000! This charming 3-bedroom, 2-bath home sits on a spacious and private 10,000 sq. ft. lot in the heart of Big Pine Key. With a garage, abundant storage, a fully fenced yard, and room to add a pool, this property offers endless potential. Inside, you'll find an inviting open-concept floor plan, two beautifully updated

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    29160 Primrose Ln, Big Pine Key, FL 33043
  • 30354 Palm Dr, Big Pine Key, FL 33043
    30354 Palm Dr, Big Pine Key, FL 33043
    30354 Palm Dr, Big Pine Key, FL 33043
    /33

    $599,000

    Pre-Foreclosure
    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    30354 Palm Dr, Big Pine Key, FL 33043

    Private Lower Keys opportunity! Nestled behind a lush hedge of mature Areca palms, this 2BR/2BA CBS home offers privacy, solid construction, and endless potential. Recent improvements include a 2018 post-Irma roof and storm shutters. The fully fenced 6,250 sq. ft. lot provides ample space for a pool, outdoor living, or tropical gardens, with a storage shed already in place. Enjoy a peaceful

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    30354 Palm Dr, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    /19

    $199,000

    $16K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $3,980,000 per Acre

    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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 453, Cudjoe 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
  • 31011 Avenue C, Big Pine Key, FL 33043
    31011 Avenue C, Big Pine Key, FL 33043
    31011 Avenue C, Big Pine Key, FL 33043
    /54

    $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 has so much to offer for the price! A spacious living area separates the primary bedroom and ensuite bath from the remaining bedrooms and bath. Features include tile floors throughout, a separate laundry room, a big sundeck and a ground-level storage enclosure. Covered parking is conveniently accessed from either Avenue C or Sands Rd. The 5,000 sq. ft.

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    31011 Avenue C, Big Pine Key, FL 33043
  • 701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    /66

    $525,000

    $14K PRICE DROP
    • 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 deck—an ideal spot for your morning coffee or evening

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • 30374 Oleander Blvd, Big Pine Key, FL 33043
    30374 Oleander Blvd, Big Pine Key, FL 33043
    30374 Oleander Blvd, Big Pine Key, FL 33043
    /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
  • 27378 Jamaica Ln, Summerland Key, FL 33042
    27378 Jamaica Ln, Summerland Key, FL 33042
    27378 Jamaica Ln, Summerland Key, FL 33042
    /3

    $375,000

    • Land
    • 6,000 Sq Ft
    • $2,722,500 per Acre

    27378 Jamaica Ln, Summerland Key, FL 33042

    Vacant lot with active building permit. Permit and plans include a fully designed green home with full concrete construction and concrete roof for 3 bedroom 2.5 bathrooms, large porch, storage and guest space, downstairs storm rated impact windows and doors, solar panel, gray water reclaim system plus rainwater system for irrigation and boat washing fish at Dawn cook your cat by dusk near Loki

    Agent Photo

    Natallie Liz

    Expert Realty LLC

    27378 Jamaica Ln, Summerland Key, FL 33042
  • 937 Gulf Dr, Summerland Key, FL 33042
    937 Gulf Dr, Summerland Key, FL 33042
    937 Gulf Dr, Summerland Key, FL 33042
    /56

    $2,220,000

    $75K PRICE DROP
    • 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,

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    937 Gulf Dr, Summerland Key, FL 33042
  • 29562 Saratoga Ave, Big Pine Key, FL 33043
    29562 Saratoga Ave, Big Pine Key, FL 33043
    29562 Saratoga Ave, Big Pine Key, FL 33043
    /70

    $1,435,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,310 Sq Ft

    29562 Saratoga Ave, Big Pine Key, FL 33043

    Embrace island living in your own tropical paradise, where comfort, space, and waterfront access create a remarkable oasis for boating and relaxation. Welcome to Pine Channel Estates, the ultimate destination for anglers and water enthusiasts. Currently operating as a successful vacation rental, this gem is ideal for a second home that can offset some of the annual costs of ownership, and

    Agent Photo

    Ryan Gernaat

    Coldwell Banker Schmitt Lower Keys (KW)

    29562 Saratoga Ave, Big Pine Key, FL 33043
  • 22865 Redfish Ln, Summerland Key, FL 33042
    22865 Redfish Ln, Summerland Key, FL 33042
    22865 Redfish Ln, Summerland Key, FL 33042
    /34

    $1,575,000

    $20K PRICE DROP
    • 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

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt RE Co.

    22865 Redfish Ln, Summerland Key, FL 33042
  • 20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    /71

    $2,795,000

    $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

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    20920 5th Ave W, Summerland Key, FL 33042
  • 21640 Overseas Hwy, Summerland Key, FL 33042
    21640 Overseas Hwy, Summerland Key, FL 33042
    21640 Overseas Hwy, 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

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    21640 Overseas Hwy, Summerland Key, FL 33042
  • 3962 No Name Rd, Big Pine Key, FL 33043
    3962 No Name Rd, Big Pine Key, FL 33043
    3962 No Name Rd, Big Pine Key, FL 33043
    /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

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    3962 No Name Rd, Big Pine Key, FL 33043
  • 629 Powell Ave, Summerland Key, FL 33042
    629 Powell Ave, Summerland Key, FL 33042
    629 Powell Ave, Summerland Key, FL 33042
    /52

    $699,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    629 Powell Ave, Summerland Key, FL 33042

    Welcome to 629 Powell Drive in Little Torch Key, the lowest-priced fully stilted CBS home currently available in the Lower Florida Keys. This elevated 2-bedroom, 1-bath canal-front home offers the ideal combination of affordability, boating access, and island living. Built for peace of mind, the home features a 2018 metal roof, accordion shutters on the doors, and panel shutters for the windows.

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    629 Powell Ave, Summerland Key, FL 33042
  • 1631 Sunrise Dr, Big Pine Key, FL 33043
    1631 Sunrise Dr, Big Pine Key, FL 33043
    1631 Sunrise Dr, Big Pine Key, FL 33043
    /57

    $2,200,000

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft

    1631 Sunrise Dr, Big Pine Key, FL 33043

    Experience the pinnacle of Florida Keys waterfront living in this newly constructed (2023) open water home on Big Pine Key. Perfectly positioned to capture breathtaking sunrise views, this CBS-built residence offers a seamless blend of modern coastal design, durability, and effortless indoor-outdoor living. Spanning 1,834 square feet, the home features 3 Bedrooms and 2 Bathrooms, thoughtfully

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1631 Sunrise Dr, Big Pine Key, FL 33043
  • 0 Niles Rd, Summerland Key, FL 33042
    0 Niles Rd, Summerland Key, FL 33042
    0 Niles Rd, 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,

    Agent Photo

    Javier Santana

    Sunland Real Estate, LLC.

    0 Niles Rd, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042
    /16

    $549,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your back deck!Unit 424 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042
  • 29534 Geraldine St, Big Pine Key, FL 33043
    29534 Geraldine St, Big Pine Key, FL 33043
    29534 Geraldine St, Big Pine Key, FL 33043
    /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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    29534 Geraldine St, Big Pine Key, FL 33043
  • 27348 Dominica Ln, Ramrod Key, FL 33042
    27348 Dominica Ln, Ramrod Key, FL 33042
    27348 Dominica Ln, Ramrod Key, FL 33042
    /51

    $2,200,000

    $299K PRICE DROP
    • 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
  • 30937 Baileys Ln, Big Pine Key, FL 33043
    30937 Baileys Ln, Big Pine Key, FL 33043
    30937 Baileys Ln, Big Pine Key, FL 33043
    /46

    $799,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,980 Sq Ft

    30937 Baileys Ln, Big Pine Key, FL 33043

    It's your lucky day! The last buyers had to cancel their contract for personal reasons prior to inspections. Whether you enjoy fishing and diving or prefer kayaking and paddle boarding through the beautiful waters of the Lower Keys, this updated 'Old Keys' home offers the perfect base for quick access to Bogie Channel, the Atlantic, and the backcountry. Situated on a 50' x 100' lot, the 2-story,

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    30937 Baileys Ln, Big Pine Key, FL 33043
  • 17286 Jamaica Ln, Summerland Key, FL 33042
    17286 Jamaica Ln, Summerland Key, FL 33042
    17286 Jamaica Ln, Summerland Key, FL 33042
    /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
  • 22953 John Silver Ln, Summerland Key, FL 33042
    22953 John Silver Ln, Summerland Key, FL 33042
    22953 John Silver Ln, Summerland Key, FL 33042
    /54

    $949,000

    $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    22953 John Silver Ln, Summerland Key, FL 33042

    Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    22953 John Silver Ln, Summerland Key, FL 33042
  • 29424 Forrestal Ave, Big Pine Key, FL 33043
    29424 Forrestal Ave, Big Pine Key, FL 33043
    29424 Forrestal Ave, Big Pine Key, FL 33043
    /76

    $1,550,000

    • 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
  • 28560 Doubloon Rd, Summerland Key, FL 33042
    28560 Doubloon Rd, Summerland Key, FL 33042
    28560 Doubloon Rd, Summerland Key, FL 33042
    /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
  • 75 Lobstertail Rd, Big Pine Key, FL 33043
    75 Lobstertail Rd, Big Pine Key, FL 33043
    75 Lobstertail Rd, Big Pine Key, FL 33043
    /21

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,304 Sq Ft

    75 Lobstertail Rd, Big Pine Key, FL 33043

    Enjoy easy island living in this beautifully updated 2BD/2BA elevated home set along a peaceful plugged canal--perfect for paddleboarding and enjoying the waterfront ambiance (no boating access).Inside, the open living space features vaulted ceilings, luxury plank vinyl flooring throughout, and great natural light, flowing out to a screened porch overlooking the canal. The standout chef's

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    75 Lobstertail Rd, Big Pine Key, FL 33043
  • 17183 Green Turtle Ln W, Summerland Key, FL 33042
    17183 Green Turtle Ln W, Summerland Key, FL 33042
    17183 Green Turtle Ln W, Summerland Key, FL 33042
    /45

    $1,155,000

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft

    17183 Green Turtle Ln W, Summerland Key, FL 33042

    Live on the water on one of the largest lots in Sugarloaf Shores, fronting a 70 ft wide crystal clear swimming canal with easy ocean access. Recent upgrades make this home truly turnkey, including a new seawall, a new boat lift 15,000 lbs), and a newer roof. The big ticket items are already done for you.The grounds are the professionally landscaped with mature trees, fruit trees, a custom

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    17183 Green Turtle Ln W, Summerland Key, FL 33042
  • 27358 Jamaica Ln, Summerland Key, FL 33042
    27358 Jamaica Ln, Summerland Key, FL 33042
    27358 Jamaica Ln, Summerland Key, FL 33042
    /58

    $949,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    27358 Jamaica Ln, Summerland Key, FL 33042

    Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with water on 2 sides this property offers 150' of waterfront including a deep water basin, excellent dockage and easy access for boating, fishing, kayaking, or paddle boarding right from your backyard. Offering a flexible floor plan

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    27358 Jamaica Ln, Summerland Key, FL 33042

Showing Results 1 - 40, Page 1 of 7

Florida Monroe County

Real Estate & Homes for Sale in Summerland Key, FL

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.

Learn more about living in Summerland Key

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 $1,761,183.
How many homes have sold over the last 12 months in Summerland Key, FL?
112 homes have sold in Summerland Key, FL over the last 12 months.
What is the average household income in Summerland Key, FL?
The average household income in Summerland Key, FL is $131K.
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 $1,285,000. If you put a 20% down payment of $257,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $6,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $283K a year to afford the median home price in Summerland Key. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Summerland Key is $131K.
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 Prices in Summerland Key, FL

The median home sale price in Summerland Key, FL is $1,102,500, up 2% year-over-year. Homes in Summerland Key sell in 112 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$1,102,500
Median Single Family Sale Price
$1,185,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$955,000
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$920
Number of Homes for Sale
47
Last 12 months Home Sales
112
Months of Supply
5.00
Median List Price
$1,285,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group