26

Summerland Key, FL Homes for Sale with Acreage

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  • /49

    $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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (866) 450-0019

    1233 Avenue A, Big Pine Key, FL 33043
  • /36

    $750,000

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

    0 Niles Rd, Summerland Key, FL 33042

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

    Agent Photo

    Javier Santana

    Sunland Real Estate, LLC.

    (786) 504-0768

    0 Niles Rd, Summerland Key, FL 33042
  • /30

    $430,000

    • 2 Beds
    • 1 Bath
    • 415 Sq Ft

    21857 Disturbed Pine Rd, Summerland Key, FL 33042

    Acre Property! I've heard it said privacy is the ultimate luxury. Your Keys bungalow in the woods with a separate screened porch enclosure 13 X 18 plus a storge room 9 X 12. Connected to the house by a wood deck walkway. Artist retreat, man cave or maybe just because you love privacy and want an escape. Lots of potential. Are you handy! Additionally, there are 2 carports, Multiple storage areas.

    Rose Dell Keller Williams Key West Compass Realty

    21857 Disturbed Pine Rd, Summerland Key, FL 33042
  • /11

    $495,000

    • 2 Beds
    • 2 Baths
    • 832 Sq Ft

    19264 Acosta Trail, Summerland Key, FL 33042

    Prime Sugarloaf Key Opportunity - Over 2 Acres of Privacy & PotentialNestled on highly desirable Sugarloaf Key, this elevated 2-bedroom, 2-bath home sits on over 2 acres of lush, private land--offering a rare opportunity to create your own piece of paradise in the Lower Florida Keys. There is a bonus room that can be used as a 3rd bedroomThe existing stilted structure provides a solid footprint

    Lanny Gardner Bluescape Real Estate

    19264 Acosta Trail, Summerland Key, FL 33042
  • /6

    $49,000

    • Land
    • 1 Acre
    • $49,000 per Acre

    10 5th Ave, Big Pine Key, FL 33043

    1 ACRE LOT IN Big Pine Key, LOCATED JUST SOUTH OF U.S. Route 1 – PEACEFUL, NATURAL SURROUNDINGS – RARE OPPORTUNITY.BEST PRICE ON THE MARKET! EXCELLENT LONG-TERM INVESTMENT! DON’T MISS THIS OPPORTUNITY!

    Mason Gascot Knowledge Base Real Estate

    10 5th Ave, Big Pine Key, FL 33043
  • /33

    $1,585,000

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft

    3167 Stewart Rd, Summerland Key, FL 33042

    SECLUDED SANCTUARY. This 3-bedroom, 2-bath home provides rare-to-find tranquility in a pristine natural setting. The two-story cottage embodies Old Florida-style with lovingly maintained stone accents and an expansive covered porch overlooking open water. The covered private deck extends your space to relax out to the water's edge. Inside, modern amenities enhance the home's charm and function.

    Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

    3167 Stewart Rd, Summerland Key, FL 33042
  • /7

    $190,000

    • Land
    • 1.02 Acres
    • $186,275 per Acre

    Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042

    Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. Great location near Sugarloaf school. Easy commute to Key West, only 25 minutes. Nearby boat ramps.

    Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

    Lot 15 bk2 Bad George Rd, Sugarloaf Key, FL 33042
  • /43

    $4,500,000

    • 2 Beds
    • 2 Baths
    • 1,467 Sq Ft

    4670 Dorn Rd, Summerland Key, FL 33042

    Discover a rare offering in the Florida Keys--an exceptional 2.84-acre waterfront estate on Big Torch Key, where serenity, seclusion, and world-class boating converge. Gracefully positioned on a coveted point lot, this remarkable property delivers sweeping open-water views, a private beach with boat launch, and protected dockage, offering an unparalleled coastal lifestyle.From sunrise to sunset,

    Sharon Davison Keller Williams Key West Compass Realty

    4670 Dorn Rd, Summerland 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
  • /4

    $100,000

    • Land
    • 1.01 Acres
    • $99,010 per Acre

    0 Acosta Rd, Summerland Key, FL 33042

    Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

    0 Acosta Rd, Summerland Key, FL 33042
  • /4

    $100,000

    • Land
    • 1.01 Acres
    • $99,010 per Acre

    0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042

    Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

    Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

    0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
  • /3

    $799,000

    • Land
    • 10 Acres
    • $79,900 per Acre

    LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

    Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

    Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

    LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
  • /4

    $400,000

    • Land
    • 1,400 Acres
    • $286 per Acre

    27378 Jamaica Ln, Summerland Key, FL 33042

    ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

    Patricia Borges Borges Realty Group LLC

    27378 Jamaica Ln, Summerland Key, FL 33042
  • /32

    $1,125,000

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft

    27821 Leeward South Rd, Little Torch Key, FL 33042

    ***OPEN HOUSE*** Saturday March 28th 10am-12pm. Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan

    Tracy Shields KeyIsle Realty

    27821 Leeward South Rd, Little Torch Key, FL 33042
  • /7

    $190,000

    • Land
    • 6,000 Acres
    • $32 per Acre

    1145 Hakluyt Ln, Cudjoe Key, FL 33042

    Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

    Daniel Pacheco United Realty Group Inc

    1145 Hakluyt Ln, Cudjoe Key, FL 33042
  • /15

    $1,395,000

    • Land
    • 2.29 Acres
    • $609,173 per Acre

    1261 Avenue A, Big Pine Key, FL 33043

    An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west

    Ally Kelley Ocean Sotheby's International Realty

    1261 Avenue A, Big Pine Key, FL 33043
  • /116

    $19,750,000

    • 6 Beds
    • 7 Baths
    • 4,402 Sq Ft

    15760 Old State Road 4a, Summerland Key, FL 33042

    Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

    Lisa Swanson The Agency Florida Keys

    15760 Old State Road 4a, Summerland Key, FL 33042
  • /100

    $8,995,000

    • 6 Beds
    • 5 Baths
    • 5,208 Sq Ft

    16750 Old State Road 4a, Summerland Key, FL 33042

    Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

    Lisa Swanson The Agency Florida Keys

    16750 Old State Road 4a, Summerland Key, FL 33042
  • /45

    $7,000,000

    • 3 Beds
    • 4 Baths
    • 2,851 Sq Ft

    0 Melody Key Unit 616249, Summerland Key, FL 33042

    An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

    Scott Forman Royal Palms Realty (KW)

    0 Melody Key Unit 616249, Summerland Key, FL 33042
  • /13

    $85,000

    • Land
    • 4 Acres
    • $21,250 per Acre

    LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

    Offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish, tarpon, permit and redfish nearby. Located on Southwest end of Little Knockemdown Key. Accessible by kayak, paddle board and shallow draft vessels. Privacy and nature abound here on Little Knockemdown Key - No roads or

    Banks Prevatt Coldwell Banker Schmitt RE Co.

    LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
  • /26

    $899,000

    • Land
    • 5 Acres
    • $179,800 per Acre

    2231 Middle Torch Rd, Summerland Key, FL 33042

    Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential. The property currently features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each

    Stephany Duvall Engel & Volkers Marathon

    2231 Middle Torch Rd, Summerland Key, FL 33042
  • /15

    $1,495,000

    • Land
    • 2.29 Acres
    • $652,838 per Acre

    1261 Avenue A, Big Pine Key, FL 33043

    NO WAIT TO BUILD!! ROGO Exempt 2.29 private and exclusive estate acreage with Bay Bottom on Bogie Channel with spectacular open water views. Property rests at the end of a quiet street and neighbors a park. USACE permitted a 412' dock before the pandemic that recently expired but is in discussion for renewal. Former home on property was damaged in Hurricane Irma and has since been demolished and

    Sasha Naimi Charles Rutenberg Realty FTL

    1261 Avenue A, Big Pine Key, FL 33043
  • /32

    $1,649,000

    • 3 Beds
    • 2 Baths
    • 2,144 Sq Ft

    1151 Sugarloaf Blvd, Summerland Key, FL 33042

    Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of canal front. Amazing view up the canal to the open water. The large floor plan featuring 3 bedrooms, 2 baths, den/office and fireplace. Kitchen has stainless appliances, quartz countertops and lots of

    Wendy Zintsmaster Truman & Co. (KW)

    1151 Sugarloaf Blvd, Summerland Key, FL 33042
  • /111

    $5,390,000

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

    3742 Seagrape St, Big Pine Key, FL 33043

    Breathe in serenity during your escape to the ''The Castle'', a luxurious gated Gulf-front estate gracefully spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a rare blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected

    Ally Kelley Ocean Sotheby's International Realty

    3742 Seagrape St, Big Pine Key, FL 33043
  • /4

    $2,499,000

    • 3 Beds
    • 1 Bath
    • 1,020 Sq Ft

    32029 Marginella Dr, Big Pine Key, FL 33043

    Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stone's throw away from Big Pine Key, this nearly 2-acre property presents

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

    32029 Marginella Dr, Big Pine Key, FL 33043
  • /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

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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