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Summerland Key, FL Homes for Sale with Garage

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  • /68

    $2,985,000

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

    23941 Henry St, Summerland Key, FL 33042

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

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    Stacy Shahan

    Island Real Estate Company Florida Keys

    (786) 686-4688

    23941 Henry St, Summerland Key, FL 33042
  • /27

    $1,055,000

    • 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
  • /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
  • /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, and

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    Christopher Tanaka

    Coldwell Banker Schmitt RE Co.

    (855) 640-6438

    30830 Palm Dr, Big Pine Key, FL 33043
  • /64

    $1,790,000

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    30463 Hawk Ln, Big Pine Key, FL 33043

    Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living.Outdoors, the home transforms into a

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    Sandra Tuttle

    Island Welcome Real Estate

    (844) 795-0878

    30463 Hawk Ln, Big Pine Key, FL 33043
  • /34

    $1,275,000

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

    1657 Watson Blvd, Big Pine Key, FL 33043

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

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    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (833) 532-1578

    1657 Watson Blvd, Big Pine Key, FL 33043
  • /89

    $3,695,000

    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    680 Elma Ave, Big Pine Key, FL 33043

    RARE west-facing private estate offering sunset views, owned bay bottom, and exceptional boating access. Welcome to Tarpon Cove, an exclusive retreat located in Big Pine Key, surrounded by the Florida Key Deer Preserve for unmatched privacy and natural beauty.The concrete residence has been meticulously reconstructed through a down-to-the-studs renovation, resulting in a 2023 effective age and is

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    Sandra Tuttle

    Island Welcome Real Estate

    (877) 359-5426

    680 Elma Ave, Big Pine Key, FL 33043
  • /55

    $999,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    22978 Port Royal Ln, Summerland Key, FL 33042

    Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully

    Anne Press Lokation Real Estate

    22978 Port Royal Ln, Summerland Key, FL 33042
  • /54

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,095 Sq Ft

    667 Caribbean Dr E, Summerland Key, FL 33042

    PILOTS and BOATERS will love this! Tucked away in the heart of Summerland Key, this charming 2-bedroom, 2-bath home captures the essence of true Florida Keys living. Surrounded by swaying palms and coastal breezes, the property features inviting wraparound balconies--perfect for morning coffee or unwinding after a day on the water.Designed with boaters in mind, you'll appreciate the deep,

    Donna Pezzi Keller Williams Key West Compass Realty

    667 Caribbean Dr E, Summerland Key, FL 33042
  • /3

    $550,000

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft

    57 Pelican Ln, Big Pine Key, FL 33043

    Embrace true island living at 57 Pelican Lane in the heart of Big Pine Key, just 30 minutes from the energy and charm of Key West. Set in a peaceful, tropical setting, this unique property captures the laid-back lifestyle the Florida Keys are known for—where days are guided by ocean breezes, sunshine, and a slower pace of life.What truly sets this opportunity apart is the oversized footprint,

    Veronica Garoufalias Zorzi

    57 Pelican Ln, Big Pine Key, FL 33043
  • /4

    $1,050,000

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    27403 Antigua Ln, Summerland Key, FL 33042

    Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

    Sonia Petraitis Caffroni Capital Intl Realty LLC

    27403 Antigua Ln, Summerland Key, FL 33042
  • /36

    $779,000

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft

    1719 Narcissus Ave, Big Pine Key, FL 33043

    Located in the peaceful National Key Deer Refuge, this charming 2BD/2BA canal front home in Eden Pines offers the perfect blend of tranquility and classic Florida Keys living. Enjoy frequent visits from the beloved Key Deer while relaxing on one of the screened porches. The property features a fenced yard, outdoor shower, garage, storage area, and rainwater collection system for easy landscape

    Karen Haack Coldwell Banker Schmitt RE Co.

    1719 Narcissus Ave, Big Pine Key, FL 33043
  • /66

    $2,795,000

    • 4 Beds
    • 5.5 Baths
    • 3,224 Sq Ft

    333 Indies Rd, Ramrod Key, FL 33042

    Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 51/2 bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis.This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a

    Greg MacLaren Internet Realty of the Florida Keys

    333 Indies Rd, Ramrod Key, FL 33042
  • /43

    $1,145,000

    • 3 Beds
    • 2 Baths
    • 1,968 Sq Ft

    19267 Hansen Trail, Summerland Key, FL 33042

    Set on over an acre of land, 19267 Hansen Trail is a truly one-of-a-kind property where modern luxury meets refined homestead living.Offering nearly 2,000 square feet of beautifully remodeled living space, this 3-bedroom, 2-bathroom residence has been thoughtfully upgraded with high-end finishes, all new impact windows and doors, and smart-home conveniences throughout.The open-concept design

    Justyn Ewald Expert Realty LLC (HQ)

    19267 Hansen Trail, Summerland Key, FL 33042
  • /35

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    29662 Independence Ave, Big Pine Key, FL 33043

    Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

    Halley Haack Coldwell Banker Schmitt RE Co.

    29662 Independence Ave, Big Pine Key, FL 33043
  • /36

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    31107 Avenue I, Big Pine Key, FL 33043

    Discover the ultimate Florida Keys lifestyle in this meticulously maintained 3-bedroom, 2-bathroom home with 2-car garage and a fresh, bright interior with new paint, this residence is move-in ready and full of potential. Located just moments from the water, you'll enjoy a sense of space and privacy that is hard to find. Whether you’re looking for a peaceful primary residence or a high-potential

    Maria Downing LoKation

    31107 Avenue I, Big Pine Key, FL 33043
  • /44

    $1,149,000

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft

    27426 Martinique Ln, Summerland Key, FL 33042

    Oceanside canal-front opportunity in Ramrod Key. This 3-bedroom, 2-bath home with a pool is ideally located near Looe Key Reef and Picnic Island, and is just a 10-minute walk to the local watering hole, The Tiki.The property includes an additional buildable lot, creating a rare opportunity to construct a second residence, guest house, or future income-producing property--significantly enhancing

    Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    27426 Martinique Ln, Summerland Key, FL 33042
  • /19

    $1,200,000

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

    715 Caribbean Dr E, Summerland Key, FL 33042

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

    Yohane Carcases Coldwell Banker Schmitt Real E

    715 Caribbean Dr E, Summerland Key, FL 33042
  • /31

    $925,000

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

    31364 Avenue J, Big Pine Key, FL 33043

    Open Waterfront Double Lot with Protected Boating and Endless PossibilitiesDiscover the best of Florida Keys waterfront living on this spacious double lot located on a quiet street on the open water with 150 feet of protective canal frontage with seawall, this property offers direct boating access to both the backcountry and the Atlantic Ocean and is only one lot in from the mouth of the canal

    Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

    31364 Avenue J, Big Pine Key, FL 33043
  • /28

    $1,950,000

    • 3 Beds
    • 3 Baths
    • 1,797 Sq Ft

    860 Lagoon Dr, Summerland Key, FL 33042

    This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThis home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

    Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

    860 Lagoon Dr, Summerland Key, FL 33042
  • /51

    $910,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    813 Hawksbill Ln, Summerland Key, FL 33042

    Charming 2BR/2BA Keys home on Upper Sugarloaf. FULL HOUSE GENERATOR WITH TRANSFER SWITCH,Built on sturdy concrete pilings with Hardie board siding and a metal roof, Large workshop, storage space on first level with Laundry room, this three-story retreat of island living. Inside, you’ll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys

    Guadalupe Perez Douglas Elliman

    813 Hawksbill Ln, Summerland Key, FL 33042
  • /16

    $989,999

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

    Rayden Vega Casa Miami Real Estate

    22961 John Avery Ln, Summerland Key, FL 33042
  • /47

    $5,390,000

    • 3 Beds
    • 3 Baths
    • 4,687 Sq Ft

    3742 Seagrape St, Big Pine Key, FL 33043

    Escape to “The Castle”, a luxurious gated Gulf-front estate spanning 1.14 acres on Big Pine Key. Built in 2014 with poured concrete, impact windows/doors, elevator, and generator, this 4,600+ sq. ft. masterpiece offers 3 bedrooms, 3 baths, and breathtaking Gulf views. Boaters enjoy 235’ of dockage: 140’ protected canal dock with lift, ramp, and slip, plus 95’ open-water pier dock with lift and

    Jo Ann Cook Ocean Sotheby's International

    3742 Seagrape St, Big Pine Key, FL 33043
  • /47

    $1,200,000

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    43 Venetian Way, Summerland Key, FL 33042

    Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

    Lori Cameron Buy The Keys

    43 Venetian Way, Summerland Key, FL 33042
  • /64

    $1,900,000

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft

    3127 Stewart Rd, Summerland Key, FL 33042

    Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

    Pamela Stangler Expert Realty LLC

    3127 Stewart Rd, Summerland Key, FL 33042
  • /18

    $1,499,000 New Construction

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

    27374 Guadaloupe Ln, Summerland Key, FL 33042

    New Construction coming Fall 2026. Step into the laid-back charm of the Florida Keys with this spacious 1,500 sqft home, perfectly situated along a peaceful boating canal in the Lower Keys, a short boat ride out to Looe Key Reef. 12x22 Swimming Pool and luscious landscaping.Inside the home: An open, airy floor plan that allows you to spread out and personalize your living space. A seamless

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    27374 Guadaloupe Ln, Summerland Key, FL 33042
  • /40

    $790,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Unlock Instant Equity on this Waterfront Gem waiting for restoration! Rare opportunity to own a waterfront escape at an unbeatable price point. This diamond in the rough is priced strictly for its condition, allowing you to build custom equity from day one. With a solid foundation and a backyard leading straight to the water's edge, this is the ultimate project for a savvy investor or visionary

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042

Home Trends in Summerland Key, FL

Housing Trends

Median Sale Price
$1,150,000
Median Single Family Sale Price
$1,185,000
Median Townhouse Sale Price
$1,750,000
Average Price Per Sq Ft
$915
Number of Homes for Sale
69
Last 12 months Home Sales
111
Months of Supply
7.50
Median List Price
$1,312,500
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-2%
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