15

Summerland Key, FL Homes for Sale with Garage

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  • /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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (844) 697-1109

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

    Agent Photo

    Yvette Toledo-Baste

    COMPASS FLORIDA LLC

    (855) 408-6871

    29051 Magnolia Ln, 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
  • /45

    $1,269,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    116 Spanish Main Dr, Summerland Key, FL 33042

    Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

    Margaret Crowley Florida Keys Realty Group

    116 Spanish Main Dr, Summerland Key, FL 33042
  • /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
  • /20

    $500,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    27910 Porgie Path, Summerland Key, FL 33042

    Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

    Alexis Seldin Xcellence

    27910 Porgie Path, Summerland Key, FL 33042
  • /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
  • /41

    $590,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, 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
  • /41

    $1,199,000

    • 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 Real E

    29662 Independence Ave, Big Pine Key, FL 33043
  • /59

    $3,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,409 Sq Ft

    17387 E Dolphin St, Sugarloaf Key, FL 33042

    Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or

    Jesus Parra Coldwell Banker Schmitt RE Co

    17387 E Dolphin St, Sugarloaf Key, FL 33042
  • /47

    $5,390,000

    $1M PRICE DROP
    • 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
  • /21

    $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,

    Yohane Carcases Coldwell Banker Schmitt Real E

    715 Caribbean Dr E, Summerland Key, FL 33042
  • /19

    $685,000

    • 3 Beds
    • 2 Baths
    • 986 Sq Ft

    29175 Violet Dr, Big Pine Key, FL 33043

    Eden Pines Gem: Fully updated, low assumable flood Modern Island Living: Updated Stilted Retreat in Golf-Cart Friendly Eden Pines!Welcome to 29175 Violet Drive, a fully updated 3-bedroom, 2-bathroom stilted sanctuary in the heart of Big Pine Key. This home is tucked into the vibrant, family-oriented community of Eden Pines Colony-a neighborhood where neighbors are friends and the island lifestyle

    Ralph Harvey LISTWITHFREEDOM.COM

    29175 Violet Dr, Big Pine Key, FL 33043
  • /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

Home Trends in Summerland Key, FL

Housing 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
$906
Number of Homes for Sale
57
Last 12 months Home Sales
114
Months of Supply
6.00
Median List Price
$1,295,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-2%
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