231

Summerland Key, FL Homes for Sale

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  • 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
  • 27395 Saint Lucie Ln, Summerland Key, FL 33042
    27395 Saint Lucie Ln, Summerland Key, FL 33042
    27395 Saint Lucie Ln, Summerland Key, FL 33042
    /43

    $1,125,000

    $125K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,368 Sq Ft

    27395 Saint Lucie Ln, Summerland Key, FL 33042

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

    Agent Photo

    Michelle Vanhoose

    Coldwell Banker Schmitt Real Estate Co.

    27395 Saint Lucie Ln, Summerland Key, FL 33042
  • 4670 Dorn Rd, Summerland Key, FL 33042
    4670 Dorn Rd, Summerland Key, FL 33042
    4670 Dorn Rd, Summerland Key, FL 33042
    /64

    $4,300,000

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft

    4670 Dorn Rd, Summerland Key, FL 33042

    There are very few places left in the Florida Keys where you can experience true waterfront privacy, EXPANSIVE acreage, protected dockage, open-water views, and direct boating access all from a single property. Blue Fish Point is one of those rare places.Set on an extraordinary 2.84-acre point lot on Big Torch Key, Blue Fish Point represents a unique opportunity to own one of the Lower

    Agent Photo

    Sharon Davison

    Keller Williams Key West Compass Realty

    4670 Dorn Rd, Summerland Key, FL 33042
  • 1106 Thatch Ln, Cudjoe Key, FL 33042
    1106 Thatch Ln, Cudjoe Key, FL 33042
    1106 Thatch Ln, Cudjoe Key, FL 33042
    /66

    $2,099,000

    • 4 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    1106 Thatch Ln, Cudjoe Key, FL 33042

    Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1106 Thatch Ln, Cudjoe Key, FL 33042
  • 27383 Saint Martin Ln, Summerland Key, FL 33042
    27383 Saint Martin Ln, Summerland Key, FL 33042
    27383 Saint Martin Ln, Summerland Key, FL 33042
    /101

    $1,399,000

    • 4 Beds
    • 3 Baths
    • 2,242 Sq Ft

    27383 Saint Martin Ln, Summerland Key, FL 33042

    Offering twice the space and an exceptional waterfront lifestyle, this 4 bedroom, 3 bath Ramrod Key home offers 2,242 sq. ft. of living space on a 6,000 sq. ft. canal-front lot and includes the adjacent 6,000 sq. ft. lot, creating a combined 12,000 sq. ft. property with plenty of room to enjoy the Florida Keys lifestyle. Boaters will appreciate the 10,000 lb. boat lift, while brand-new Trex

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    27383 Saint Martin Ln, Summerland Key, FL 33042
  • 1160 Avenue A, Big Pine Key, FL 33043
    1160 Avenue A, Big Pine Key, FL 33043
    1160 Avenue A, Big Pine Key, FL 33043
    /82

    $799,000

    • 4 Beds
    • 4 Baths
    • 2,284 Sq Ft

    1160 Avenue A, Big Pine Key, FL 33043

    Set on a spacious 13,750 sq. ft. double lot, this 4 bedroom, 4 bath home offers 2,284 sq. ft. of living space surrounded by lush tropical landscaping and an exceptional collection of 16 varieties of fruit trees. Originally built in 1981 and extensively renovated following Hurricane Irma, the residence features a metal roof, Hardie Board siding and trim, impact windows, seamless gutters and a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1160 Avenue A, Big Pine Key, FL 33043
  • 24923 Park Dr, Summerland Key, FL 33042
    24923 Park Dr, Summerland Key, FL 33042
    24923 Park Dr, Summerland Key, FL 33042
    /22

    $899,000

    $51K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 902 Sq Ft

    24923 Park Dr, Summerland Key, FL 33042

    Tropical Waterfront Living in the Florida Keys!Welcome to 24923 Park Drive in beautiful Summerland Key, where laid back Florida Keys living meets ultimate waterfront lifestyle. This charming canal-front property offers an opportunity to create your own paradise in one of the Keys' most desirable boating communities.Positioned along a wide protected canal, the property features

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    24923 Park 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 withFlorida 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
  • 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

    $565,000

    $34K PRICE DROP 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
  • 3962-3964 No Name Rd, Big Pine Key, FL 33043
    3962-3964 No Name Rd, Big Pine Key, FL 33043
    3962-3964 No Name Rd, Big Pine Key, FL 33043
    /19

    $925,000

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

    3962-3964 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

    3962-3964 No Name Rd, Big Pine Key, FL 33043
  • 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

    $509,000

    $16K PRICE DROP
    • 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 homenestled 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 Lower Keys (KW)

    31011 Avenue C, Big Pine Key, FL 33043
  • 29038 Violet Dr, Big Pine Key, FL 33043
    29038 Violet Dr, Big Pine Key, FL 33043
    29038 Violet Dr, Big Pine Key, FL 33043
    /55

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    29038 Violet Dr, Big Pine Key, FL 33043

    Boat, swim, soak, repeat.A private Fl. Key boating, and resort style retreat designed for life outdoors. Enjoy your own boat slip, cool off in the pool, unwind in the hot tub and relax in a low-maintenance tropical setting. Elevated living, 3 bedroom, 2 bathrooms and a comfortable semi-updated interior make this an easy place to enjoy now and personalize over time.

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    29038 Violet Dr, 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

    Open Sat 9:30AM - 12PM $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
  • 27378 Jamaica Ln, Summerland Key, FL 33042
    27378 Jamaica Ln, Summerland Key, FL 33042
    27378 Jamaica Ln, Summerland Key, FL 33042
    /6

    $375,000

    • Land
    • 6,098 Sq Ft
    • $2,678,571 per Acre

    27378 Jamaica Ln, Summerland Key, FL 33042

    BUILD TODAY! Rare shovel-ready lot in the heart of Ramrod Key -- where Monroe County's permit moratorium has effectively stopped new residential development. This Breezeswept Beach Estates parcel comes with an ACTIVE allocated ROGO single-family PERMIT (SFDUP-2022-0059) already in hand. Foundation augers are in the ground. An Army Corps of Engineers-concrete seawall APPROVED DOCK PERMIT IS

    Agent Photo

    Natallie Liz

    Island Welcome Real Estate 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
  • 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
  • 2828 Central Ave, Big Pine Key, FL 33043
    2828 Central Ave, Big Pine Key, FL 33043
    2828 Central Ave, Big Pine Key, FL 33043
    /63

    $549,000

    • 3 Beds
    • 1 Bath
    • 1,389 Sq Ft

    2828 Central Ave, Big Pine Key, FL 33043

    Peaceful Big Pine Key retreat nestled within the beautiful National Key Deer Wildlife Refuge. This ground-level 3-bedroom, 1-bath concrete home offers the laid-back Keys lifestyle surrounded by lush, mature tropical landscaping and abundant natural beauty.The fully fenced yard provides privacy and space to enjoy the peaceful setting, while the durable metal roof and hurricane shutters add

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    2828 Central Ave, Big Pine Key, FL 33043
  • 31364 Avenue J, Big Pine Key, FL 33043
    31364 Avenue J, Big Pine Key, FL 33043
    31364 Avenue J, Big Pine Key, FL 33043
    /40

    $869,500

    • 2 Beds
    • 2 Baths
    • 1,291 Sq Ft

    31364 Avenue J, Big Pine Key, FL 33043

    Boating and open-water views await! This Big Pine Key property offers unobstructed water views along with 150 ft. of concrete seawall, protected dockage, and plenty of potential for the buyer who's ready to add some TLC. The spacious 1,291 sq. ft. living area features beautiful water views from the front porch, great room, and main bedroom. A screened porch and open deck overlook the canal that

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    31364 Avenue J, 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

    Prime residential lot opportunity in Key Colony Beach, Monroe County, located at 0 Niles Rd, Key Colony, FL 33042.This approximately 9.2-acre property is situated in the Florida Keys with convenient access to nearby points of interest including Murray's Market (0.45 miles), Big Pine Key Boat Rentals (0.6 miles), Merrill Homes Inc (0.6 miles), and WWUS-FM Big Pine Key (1.85 miles). The lot

    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 homenestled 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
  • 17286 Jamaica Ln, Sugarloaf Key, FL 33042
    17286 Jamaica Ln, Sugarloaf Key, FL 33042
    17286 Jamaica Ln, Sugarloaf Key, FL 33042
    /44

    $1,200,000

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

    17286 Jamaica Ln, Sugarloaf 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, Sugarloaf 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 Lower Keys (KW)

    29424 Forrestal Ave, Big Pine Key, FL 33043
  • 545 Ixora Dr, Big Pine Key, FL 33043
    545 Ixora Dr, Big Pine Key, FL 33043
    545 Ixora Dr, Big Pine Key, FL 33043
    /30

    $1,300,000

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    545 Ixora Dr, Big Pine Key, FL 33043

    A rare find on Big Pine Key! This home is ground level, but above flood. It sits on almost 1/2 an acre, with aprox 290 feet of concrete seawall, with access to the Gulf, and the Atlantic. Located in a private neighborhood close to Big Pine park, with 3 bedrooms, 2 bathrooms, an inground pool, and a beautiful screened in back porch, this home has a lot to offer!

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    545 Ixora Dr, 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 Lower Keys (KW)

    28560 Doubloon Rd, Summerland 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

    This spacious Big Pine Key home is situated on a lushly landscaped 12,500 sq. ft. double lot and offers 2,136 sq. ft. of living area with 4 bedrooms, 2 baths, fresh interior colors and decor, solid bamboo and tile flooring. The expansive layout has plenty of room for family and guests, including a breakfast room, a walk-through dressing room off the primary bedroom, and laundry/utility room. The

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt Lower Keys (KW)

    30374 Oleander Blvd, Big Pine Key, FL 33043
  • 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
  • 27358 Jamaica Ln, Ramrod Key, FL 33042
    27358 Jamaica Ln, Ramrod Key, FL 33042
    27358 Jamaica Ln, Ramrod Key, FL 33042
    /58

    $949,000

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

    27358 Jamaica Ln, Ramrod 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, Ramrod 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

    $474,000

    $25K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $1,394,118 per Acre

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit and DEP and Army Corp mitigation fees paid 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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • 27 Lake Dr N, Summerland Key, FL 33042
    27 Lake Dr N, Summerland Key, FL 33042
    27 Lake Dr N, Summerland Key, FL 33042
    /34

    $799,000

    $91K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,638 Sq Ft

    27 Lake Dr N, Summerland Key, FL 33042

    Welcome to the Mango Cottage on Summerland Key! Tucked away on a quiet dead-end street, this 3 bedroom, 1 bath canal front CBS home combines the laid back Florida Keys lifestyle with excellent boating access and a few features you simply don't find everywhere. Surrounded by multiple mature fruit trees, including several mango trees! This property has a distinctly tropical feel from the moment you

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    27 Lake Dr N, Summerland Key, FL 33042
  • 361 Avenue D, Summerland Key, FL 33042
    361 Avenue D, Summerland Key, FL 33042
    361 Avenue D, Summerland Key, FL 33042
    /63

    $3,100,000

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

    361 Avenue D, Summerland Key, FL 33042

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

    Agent Photo

    Stacy Shahan

    Island Real Estate Company Florida Keys

    361 Avenue D, Summerland Key, FL 33042
  • 16770 Cypress Rd, Sugarloaf Shores, FL 33042
    16770 Cypress Rd, Sugarloaf Shores, FL 33042
    16770 Cypress Rd, Sugarloaf Shores, FL 33042
    /20

    $999,000

    • Land
    • 21,780 Sq Ft
    • $1,998,000 per Acre

    16770 Cypress Rd, Sugarloaf Shores, FL 33042

    Active Permit! Start building today! Save years of planning and permitting with this exceptional 21,600 sq. ft. waterfront parcel in sought-after Sugarloaf Shores. Situated on a wide canal with ocean-side access, this property includes transferable approvals for a single family home with a 100' dock and a 15,000-lb boat lift, along with engineered plans for a custom pool offering the ultimate

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    16770 Cypress Rd, Sugarloaf Shores, FL 33042
  • 701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
    /23

    $459,000

    • Land
    • 1,742 Sq Ft
    • $11,475,000 per Acre

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your seawall!RV Lot 609 in Venture Out.Experience the epitome of waterfront Florida Keys living on this Canal Front RV Lot with 40' Seawallnestled within an exclusive gated community.This beautiful canal front property boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 40 ft seawall.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

Showing Results 1 - 40, Page 1 of 6

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

Summerland Key, FL Home Prices

Summerland Key, FL
Median Home Price
$1,269,000
Median Sale Price
$1,100,000
-1% YoY
Avg. Price per Square Foot
$922
Median Single Family Price
$1,170,000
Median Townhouse Price
$1,750,000
Median Condo Price
$535,000
Total Active Listings
231 listings
Market Conditions
4 Months of Supply
Balanced Market

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 $1,795,249.
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 $1,269,000. If you put a 20% down payment of $253,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $6,720 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $288K 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.
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