287

Summerland Key, FL Homes for Sale

Section Image Section Image
  • 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 RE Co.

    (866) 531-8155

    17013 Coral Dr, Sugarloaf 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

    (833) 754-7970

    17015 Wahoo Ln W, Sugarloaf 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

    $1,699,000

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

    1607 Sunrise Dr, Big Pine Key, FL 33043

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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 600-4794

    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

    (645) 241-8287

    701 Spanish Main Dr Unit 182, Cudjoe 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

    $1,379,000

    $16K 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)

    (645) 228-9075

    16941 Driftwood Ln, Summerland Key, FL 33042
  • 683 Blackbeard Rd, Summerland Key, FL 33042
    683 Blackbeard Rd, Summerland Key, FL 33042
    683 Blackbeard Rd, Summerland Key, FL 33042
    /48

    $945,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    683 Blackbeard Rd, Summerland Key, FL 33042

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

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (645) 239-1385

    683 Blackbeard Rd, Summerland Key, FL 33042
  • 17151 Marlin Dr, Sugarloaf Key, FL 33042
    17151 Marlin Dr, Sugarloaf Key, FL 33042
    17151 Marlin Dr, Sugarloaf 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

    (855) 679-9394

    17151 Marlin Dr, Sugarloaf 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

    (645) 231-3870

    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

    New interior photos! 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 with brand new Maytag washer and dryer, 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.

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (877) 335-4434

    31011 Avenue C, Big Pine Key, FL 33043
  • 823 Indies Rd, Ramrod Key, FL 33042
    823 Indies Rd, Ramrod Key, FL 33042
    823 Indies Rd, Ramrod Key, FL 33042
    /47

    $1,399,000

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

    823 Indies Rd, Ramrod Key, FL 33042

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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 981-8996

    823 Indies Rd, Ramrod Key, FL 33042
  • 1657 Watson Blvd, Big Pine Key, FL 33043
    1657 Watson Blvd, Big Pine Key, FL 33043
    1657 Watson Blvd, Big Pine Key, FL 33043
    /34

    $1,275,000

    $124K PRICE DROP
    • 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

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (833) 532-1578

    1657 Watson Blvd, 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

    (645) 666-0297

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • 23941 Henry St, Summerland Key, FL 33042
    23941 Henry St, Summerland Key, FL 33042
    23941 Henry St, Summerland Key, FL 33042
    /73

    $2,775,000

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

    23941 Henry St, Summerland Key, FL 33042

    Beach House Oceanfront retreat with protected dockage & direct access to both 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

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    (645) 229-8331

    23941 Henry St, Summerland Key, FL 33042
  • 1672 Pandorea Ln, Big Pine Key, FL 33043
    1672 Pandorea Ln, Big Pine Key, FL 33043
    1672 Pandorea Ln, Big Pine Key, FL 33043
    /48

    $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, granite counters in the

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (855) 508-0388

    1672 Pandorea Ln, Big Pine Key, FL 33043
  • 30374 Oleander Blvd, Big Pine Key, FL 33043
    30374 Oleander Blvd, Big Pine Key, FL 33043
    30374 Oleander Blvd, 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

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (877) 357-0409

    30374 Oleander Blvd, Big Pine Key, FL 33043
  • 29562 Saratoga Ave, Big Pine Key, FL 33043
    29562 Saratoga Ave, Big Pine Key, FL 33043
    29562 Saratoga Ave, Big Pine Key, FL 33043
    /67

    $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)

    (833) 404-4618

    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.

    (645) 230-1445

    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

    (877) 939-4083

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

    $849,000

    $76K 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

    (844) 619-6402

    195 W Shore Dr, 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)

    (855) 799-5158

    21640 Overseas Hwy, Summerland 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

    $3,500,000

    • 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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-0155

    1083 Labat Ln, Cudjoe 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

    (888) 275-1086

    3962 No Name Rd, Big Pine Key, FL 33043
  • 21012 6th Ave, Summerland Key, FL 33042
    21012 6th Ave, Summerland Key, FL 33042
    21012 6th Ave, Summerland Key, FL 33042
    /61

    $1,449,000

    • 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

    (645) 666-1284

    21012 6th 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

    (866) 828-4958

    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.

    (786) 504-0768

    0 Niles Rd, Summerland 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

    (844) 697-1109

    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

    $2,499,000

    • 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

    (645) 238-7522

    27348 Dominica Ln, Ramrod 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
    /74

    $1,750,000

    $40K PRICE DROP
    • 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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (844) 795-0878

    30463 Hawk Ln, Big Pine Key, FL 33043
  • 715 Caribbean Dr E, Summerland Key, FL 33042
    715 Caribbean Dr E, Summerland Key, FL 33042
    715 Caribbean Dr E, Summerland Key, FL 33042
    /16

    $1,150,000

    $150K PRICE DROP
    • 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,

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (844) 920-0831

    715 Caribbean Dr E, Summerland 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
    /45

    $849,000

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

    30937 Baileys Ln, Big Pine Key, FL 33043

    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, single-family residence features a cut-in boat slip with a boat lift beneath the expansive great room, along

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (866) 810-8945

    30937 Baileys Ln, Big Pine Key, FL 33043
  • 1148 Big Pine Ave, Big Pine Key, FL 33043
    1148 Big Pine Ave, Big Pine Key, FL 33043
    1148 Big Pine Ave, Big Pine Key, FL 33043
    /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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 703-1366

    1148 Big Pine Ave, 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

    $215,000

    $35K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $4,300,000 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

    (645) 229-8475

    701 Spanish Main Dr Unit 610, Cudjoe 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

    $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

    (833) 691-0812

    29160 Primrose 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

    (833) 702-3934

    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

    $1,099,000

    • 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

    (645) 241-8464

    22953 John Silver Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
    /66

    $799,000

    $50K PRICE DROP
    • 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 230-0325

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
  • 28560 Doubloon Rd, Summerland Key, FL 33042
    28560 Doubloon Rd, Summerland Key, FL 33042
    28560 Doubloon Rd, Summerland Key, FL 33042
    /60

    $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.

    (645) 218-9799

    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

    (877) 375-6513

    75 Lobstertail Rd, Big Pine Key, FL 33043
  • 28573 Le Grand Rd, Little Torch Key, FL 33042
    28573 Le Grand Rd, Little Torch Key, FL 33042
    28573 Le Grand Rd, Little Torch Key, FL 33042
    /41

    $1,899,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,998 Sq Ft

    28573 Le Grand Rd, Little Torch Key, FL 33042

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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 560-6494

    28573 Le Grand Rd, Little Torch Key, FL 33042
  • 63 Sugarloaf Dr, Sugarloaf Key, FL 33042
    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
    /10

    $499,000

    • Land
    • 14,706 Sq Ft
    • $1,478,066 per Acre

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 917-4422

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

Showing Results 1 - 40, Page 1 of 8

Florida Monroe County Summerland Key

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 $1,670,904.
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 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 6.31%, your estimated principal and interest payment would be $6,370 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $273K a year to afford the median home price in Summerland Key. Learn how much home you can afford with our Home Affordability Calculator. 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 $1,100,000, down 2% year-over-year. Homes in Summerland Key sell in 114 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,150,000
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$899
Number of Homes for Sale
54
Last 12 months Home Sales
110
Months of Supply
5.90
Median List Price
$1,285,000
Median Change From 1st List Price
9%
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