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Summerland Key, FL Homes for Sale

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  • /62

    $5,200,000

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

    17013 Coral Dr, Sugarloaf Key, FL 33042

    Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt RE Co.

    (866) 531-8155

    17013 Coral Dr, 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 754-7970

    17015 Wahoo Ln W, Sugarloaf Key, FL 33042
  • /36

    $750,000

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

    0 Niles Rd, Summerland Key, FL 33042

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

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    Javier Santana

    Sunland Real Estate, LLC.

    (786) 504-0768

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

    $1,195,000

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

    29534 Geraldine St, Big Pine Key, FL 33043

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

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    Sandra Tuttle

    Island Welcome Real Estate

    (844) 697-1109

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

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (844) 920-0831

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

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    Sandra Tuttle

    Island Welcome Real Estate

    (844) 795-0878

    30463 Hawk 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

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    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (866) 810-8945

    30937 Baileys Ln, 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 703-1366

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

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    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 229-8475

    701 Spanish Main Dr Unit 610, Cudjoe 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 702-3934

    17286 Jamaica Ln, Summerland Key, FL 33042
  • /51

    $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
  • /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

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    Ian Calderwood

    Bluescape Real Estate- Venture

    (645) 230-0325

    701 Spanish Main Dr Unit 172, Cudjoe 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

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    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (645) 218-9799

    28560 Doubloon Rd, Summerland Key, FL 33042
  • /23

    $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 kitchen

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    Sandra Tuttle

    Island Welcome Real Estate

    (877) 375-6513

    75 Lobstertail Rd, Big Pine Key, FL 33043
  • /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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 560-6494

    28573 Le Grand Rd, Little Torch Key, FL 33042
  • /47

    $698,800

    • 3 Beds
    • 2 Baths
    • 1,039 Sq Ft

    29048 Iris Dr, Big Pine Key, FL 33043

    50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water heater,

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    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (833) 968-8150

    29048 Iris Dr, Big Pine Key, FL 33043
  • /10

    $499,000

    • Land

    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.

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 917-4422

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • /28

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,184 Sq Ft

    290 46th St, Summerland Key, FL 33042

    Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport! This property is a fixer-upper, or teardown, located on Summerland Key, at the base of the airport runway. 2/1 on one side, and an additional 12 x32 en suite with a separate entrance on the other side. The home sits on a rare double lot totaling 11,000 SF. If you like privacy, this is it,

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (645) 219-1684

    290 46th St, Summerland Key, FL 33042
  • /36

    $665,000

    $53K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,497 Sq Ft

    30416 Coconut Hwy, Big Pine Key, FL 33043

    Looking for a lot of land in the Keys, and a well-maintained home? This rare 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV, boat trailers, so much more! Over 1⁄2 acre, the 4 lots are bordered by Coconut Hwy. to the north, Avenue B to the west, and Hibiscus Ln. to the south from which vehicles can access the large, fenced portion of the back yard. Step inside

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    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (888) 817-7679

    30416 Coconut Hwy, Big Pine Key, FL 33043
  • /41

    $550,000

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft

    30372 Palm Dr, Big Pine Key, FL 33043

    Well-priced Keys living starts here! This 12,500 sq. ft. double lot offers ample parking and room to add a pool, garage, tiki hut, or more. In 2022, the current owner added a metal roof, impact-resistant windows and doors, and Mitsubishi mini-split A/C units. Inside, the home features a spacious great room, three bedrooms, one updated bath, and tile floors throughout. Outside, you'll find a solar

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    Patti Nickless

    Coldwell Banker Schmitt RE Co.

    (888) 376-2422

    30372 Palm Dr, Big Pine Key, FL 33043
  • /43

    $1,230,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,368 Sq Ft

    27395 Saint Lucie Ln, Summerland Key, FL 33042

    Professional photos coming soon! 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

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    Michelle Vanhoose

    Coldwell Banker Schmitt Real Estate Co.

    (786) 882-1637

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

    $1,055,000

    $110K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,344 Sq Ft

    29051 Magnolia Ln, Big Pine Key, FL 33043

    Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers an exceptional opportunity to enjoy the relaxed Lower Florida Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with

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    Yvette Toledo-Baste

    COMPASS FLORIDA LLC

    (855) 408-6871

    29051 Magnolia Ln, Big Pine Key, FL 33043
  • /50

    $1,385,000

    • 3 Beds
    • 2 Baths
    • 2,556 Sq Ft

    30830 Palm Dr, Big Pine Key, FL 33043

    Discover the perfect Florida Keys waterfront retreat in Big Pine Key. Situated on an oversized 16,779 sq ft lot on a quiet street away from the highway, this solidly built concrete block home with a concrete subfloor and stucco finish offers durability, privacy, and the laid-back island lifestyle buyers dream about.Boaters will appreciate 112 feet of concrete seawall, a 10,000 lb boat lift,

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    Christopher Tanaka

    Coldwell Banker Schmitt RE Co.

    (855) 640-6438

    30830 Palm Dr, Big Pine Key, FL 33043
  • /22

    $685,000

    $29K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    4039 Egret Ln, Summerland Key, FL 33042

    Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

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    Sandra Tuttle

    Island Welcome Real Estate

    (645) 238-9391

    4039 Egret Ln, Summerland Key, FL 33042
  • /46

    $795,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    29034 Rose Dr, Big Pine Key, FL 33043

    Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is

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    Ryan Gernaat

    Coldwell Banker Schmitt Lower Keys (KW)

    (866) 610-4443

    29034 Rose Dr, Big Pine Key, FL 33043
  • /38

    $1,399,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    51 Drost Dr, Summerland Key, FL 33042

    Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 808-1276

    51 Drost Dr, Summerland Key, FL 33042
  • /85

    $1,695,000

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

    30363 Flamingo Ln, Big Pine Key, FL 33043

    Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete waterfront home offers quick access to both the Atlantic and Gulf, putting you in the heart of world-class fishing and diving. Located just a few miles from Bahia Honda State Park, you're ideally positioned for elite tarpon fishing, backcountry action, reef trips, and offshore runs. The dock is built for

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    Coby Taylor

    Expert Realty LLC (HQ)

    (855) 922-5281

    30363 Flamingo Ln, Big Pine Key, FL 33043
  • /43

    $1,799,000

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

    51 Sawyer Dr, Cudjoe Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 618-8489

    51 Sawyer Dr, Cudjoe Key, FL 33042
  • /73

    $2,999,000

    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft

    17041 Marlin Dr, Sugarloaf Key, FL 33042

    Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 684-0921

    17041 Marlin Dr, Sugarloaf Key, FL 33042
  • /18

    $599,900

    • Land
    • 27,878 Sq Ft
    • $937,344 per Acre

    17215 Keystone Rd, Sugarloaf Key, FL 33042

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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 747-8360

    17215 Keystone Rd, Sugarloaf Key, FL 33042
  • /5

    $285,000

    • Land
    • 1.01 Acres
    • $282,178 per Acre

    Unlisted Address

    Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

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    Coby Taylor

    Expert Realty LLC (HQ)

    (645) 219-1669

    Unlisted Address
  • /9

    $899,000

    • Land
    • 12,000 Sq Ft
    • $3,263,370 per Acre

    24764 Overseas Hwy, Summerland Key, FL 33042

    Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet of premium frontage - both on the highly visible Overseas Highway and on deep-water accessible oceanside canal - this property delivers exceptional visibility and flexible commercial potential. 120' concrete dockage with direct

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    Stacy Shahan

    Island Real Estate Company Florida Keys

    (786) 952-6715

    24764 Overseas Hwy, Summerland Key, FL 33042
  • /43

    $649,000

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    19464 Seminole St, Summerland Key, FL 33042

    Move-In Ready Sugarloaf Key Retreat! Ideally located on beautiful Sugarloaf Key, this charming elevated 2-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island living. Just moments from a wonderful elementary and middle school, this bright and airy home welcomes you with an open floor plan filled with beautiful natural light, creating a warm and inviting atmosphere

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    Miriam Novotny

    Compass Florida, LLC

    (645) 231-3946

    19464 Seminole St, Summerland Key, FL 33042
  • /49

    $1,399,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    21250 Conch Dr, Cudjoe Key, FL 33042

    Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (855) 959-3732

    21250 Conch Dr, Cudjoe Key, FL 33042
  • /2

    $45,000

    $5K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $281,250 per Acre

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042

    Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. worth 2 pts applying for Letter 2 additional lots available each for $50,000

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    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (844) 484-2446

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042
  • /8

    $120,000

    • Land

    Lot 6 Vacant Land, Big Pine Key, FL 33043

    Positioned just off US-1 (Jimmy Buffett Memorial Highway), this parcel of land benefits from excellent visibility and accessibility, supporting a wide variety of potential commercial uses.Potential for securing valuable ROGO points for future permitting needs in Monroe County (buyer to verify the number of ROGO points with the County).

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    Austin Kimbler

    Expert Realty LLC (HQ)

    (833) 721-5033

    Lot 6 Vacant Land, Big Pine Key, FL 33043
  • /65

    $2,499,000

    • 3 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 838-6010

    21023 2nd Ave, Summerland Key, FL 33042
  • /48

    $2,699,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    1233 Avenue A, Big Pine Key, FL 33043

    Tucked away on 2 gated acres along the pristine waters of Bogie Channel, Dei Paradiso is a one-of-a-kind open water estate offering total privacy, resort-style amenities, and world-class boating access to both the ocean and backcountry. Just a mile off the Overseas Highway, peace and convenience converge in this tropical retreat. Awaken to dazzling sunrises and wind down beneath the glow of

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 986-5271

    1233 Avenue A, Big Pine Key, FL 33043
  • /2

    $45,000

    $5K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $281,250 per Acre

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

    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 $50,000

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    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (844) 526-4158

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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 600-4794

    1607 Sunrise Dr, Big Pine Key, FL 33043

Showing Results 1 - 40, Page 1 of 8

Why Live in Summerland Key

Summerland Key delivers the quintessential Florida Keys lifestyle with a quieter, more laidback feel than nearby Key West, located about 25 miles away. This secluded Lower Keys community is known for its waterfront homes, deepwater canals and effortless access to boating, fishing and other nautical adventures. A private residential airport and Mote Marine Laboratory’s International Center for Coral Reef Research & Restoration add to its distinct character and local employment base. Homes are concentrated on the south side of the community, where many of the multi-level properties feature docks, boat lifts and pools. Tree-lined streets and lush tropical landscaping enhance curb appeal. Exclusive enclaves like Seven Palms Cove highlight the area’s appeal for high-end buyers and investors. With a median age of 58 and homeownership above 80%, Summerland Key attracts full-time residents as well as second-home owners. Outdoor recreation is central to life here, from boating and snorkeling to offshore and flats fishing. Nearby Bahia Honda State Park offers beaches and camping. Casual restaurants and a local seafood market complete the relaxed island lifestyle.

Frequently Asked Questions

What is the average home price in Summerland Key, FL?
Homes for sale in Summerland Key, FL have an average home price of $1,687,826.
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?
112 homes have sold in Summerland Key, FL over the last 12 months.
What are the most popular zip codes in Summerland Key, FL?
The most popular zip codes in Summerland Key, FL include 33042, 33043 and 33040.
How much do you need to make to afford a house in Summerland Key?
The median home price in Summerland Key is $1,299,000. If you put a 20% down payment of $259,800 and had a 30-year fixed mortgage with an interest rate of 6.53%, your estimated principal and interest payment would be $6,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $282K a year to afford the median home price in Summerland Key. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Summerland Key, FL?
Summerland Key, FL has highly rated public and private schools. Some of the best schools in Summerland Key based on Niche Grades are Sugarloaf School and Key West High School. Browse all the schools in Summerland Key, FL to learn more.

Home Trends in Summerland Key, FL

Housing Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,157,000
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$910
Number of Homes for Sale
58
Last 12 months Home Sales
112
Months of Supply
6.20
Median List Price
$1,299,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-2%
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