30

Summerland Key, FL Homes for Sale under $300,000

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  • /8

    $120,000

    • Land
    • 3,900 Sq Ft
    • $1,340,308 per Acre

    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).

    Agent Photo

    Austin Kimbler

    Expert Realty LLC (HQ)

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

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    Unlisted Address
  • /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

    0 Bk 15 Lt 5 Unit 619550, 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 5 Unit 619550, Cudjoe Key, FL 33042
  • /2

    $54,000

    $6K PRICE DROP
    • Land

    0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043

    ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

    Donna Pezzi Keller Williams Key West Compass Realty

    0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043
  • /17

    $255,000

    $10K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /58

    $267,000

    $28K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

    $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
  • /17

    $4,500

    • 3 Beds
    • 2 Baths
    • 1,565 Sq Ft

    24840 Park Dr, Summerland Key, FL 33042

    { WOW } Try and find a rental in the Lower Florida Keys! Then, yet again, one with 3 bedrooms, 2 Full baths and spacious Kitchen, Livingroom, Dinning open concept layout. Welcome to living in Summerland Key Cove. Live where others vacation — in Summerland Key Cove, just 25 miles from Key West. Whether you're a boater, pilot, fisherman, or someone who simply enjoys walking their dog by the water,

    Thomas Murphy LAER Realty

    24840 Park Dr, Summerland Key, FL 33042
  • /2

    $235,000

    $20K PRICE DROP
    • Land
    • 7.09 Acres
    • $33,145 per Acre

    Lot 7 Parcel 10, Cudjoe Key, FL 33042

    This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

    Pamela Stangler Expert Realty LLC

    Lot 7 Parcel 10, Cudjoe Key, FL 33042
  • /24

    $259,000

    $6K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,180,000 per Acre

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /6

    $165,000

    $60K PRICE DROP
    • Land
    • 0 Sq Ft

    29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

    Transferable ROGO Exempt Building Right + 2,250 Sq Ft Lot - Build Immediately! Rare opportunity to own a ROGO-exempt parcel in the Florida Keys, allowing you to build right away with no waiting period. This property allows flexibility--use the building right on-site, transfer it to another parcel, or sell it separately, as it is fully transferable. Bring your vision to life and build your dream

    Steven Koleno Beycome of Florida, LLC

    29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
  • /2

    $85,000

    • Land
    • 6,667 Sq Ft
    • $555,279 per Acre

    Vacant Central Ave, Big Pine Key, FL 33043

    Tier 2 parcel with potential eligibility for ROGO points toward future building permits in Monroe County. Buyer to verify ROGO point availability and requirements with Monroe County. Adjacent lot is for sale MLS#618997

    Deni Heintzelman KeyIsle Realty

    Vacant Central Ave, Big Pine Key, FL 33043
  • /4

    $189,000

    • Land
    • 0 Sq Ft

    29859 Overseas Hwy #20, Big Pine, FL 33043

    Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across

    Liza Dieppa Coldwell Banker Realty

    29859 Overseas Hwy #20, Big Pine, FL 33043
  • /4

    $189,000

    • Land
    • 0 Sq Ft

    29859 Overseas Hwy, Big Pine Key, FL 33043

    Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across the

    Liza Dieppa Coldwell Banker Realty

    29859 Overseas Hwy, Big Pine Key, FL 33043
  • /7

    $170,000

    • Land
    • 5,662 Sq Ft
    • $1,307,692 per Acre

    Lot 27 Dorn Rd, Torch Key, FL 33042

    If you love fishing, love the water, and hate the big crowds, this is the place for you! Upon arrival, the first thing you will notice is the peace and quiet. Easy access to the Gulf of America and Atlantic Ocean. This property is adjacent to my other listing which is owned by the same person. This would be an excellent opportunity to own a double lot on Big Torch Key! Adjacent property (blue

    Dylan Calhoun Luxe Properties

    Lot 27 Dorn Rd, Torch Key, FL 33042
  • /3

    $215,000

    • Land
    • 7,840 Sq Ft
    • $1,194,444 per Acre

    27334 Saint Lucie Ln, Big Pine, FL 33042

    Rare opportunity to own a piece of paradise in the heart of the Florida Keys. Located in the desirable Breezeswept Beach Estates community on Ramrod Key, this canal-front homesite offers the perfect blend of tranquility, natural beauty, and island living. The property benefits from a recorded Lot Line Adjustment that established the current buildable lot configuration, creating an excellent

    Gilberto Imery Gilvan Realty Corp

    27334 Saint Lucie Ln, Big Pine, FL 33042
  • /3

    $64,750

    • Land

    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

    ROGO Lot. Letter on hand from Monroe County granting 2 points

    Jenna Stauffer Ocean Sotheby's International Realty

    0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
  • /33

    $249,000

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

    Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room.The property is currently occupied by a long-term

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • /9

    $12,040

    $2K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,855 Sq Ft

    28502 Channel View Dr, Little Torch Key, FL 33042

    This is a 3 story furnished or unfurnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

    Joseph Danieli AKT Realty LLC

    28502 Channel View Dr, Little Torch Key, FL 33042
  • /3

    $275,000

    • Land
    • 0 Sq Ft

    0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042

    Take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

    Pamela Stangler Expert Realty LLC

    0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042
  • /4

    $189,000

    • Land
    • 0 Sq Ft

    29859 Overseas Hwy #21, Big Pine, FL 33043

    Enjoy the Florida Keys lifestyle with this RV lot offering access to a variety of community amenities, including a swimming pool, clubhouse, shuffleboard, picnic and grilling areas, laundry facilities, and bathhouse.A convenient bike path located directly in front of the park provides easy access to nearby shopping and restaurants. For boating enthusiasts, boat storage is available across

    Liza Dieppa Coldwell Banker Realty

    29859 Overseas Hwy #21, Big Pine, FL 33043
  • /20

    $150,000

    • Land
    • 5,662 Sq Ft
    • $1,153,846 per Acre

    30860 Malaga Ln, Big Pine Key, FL 33043

    Vacant waterfront lot in the desirable Doctor's Arm neighborhood of Big Pine Key. This cleared lot has 55 feet of canal frontage, plenty of room for a seawall and your boat. The canal opens into Bogie channel, one of the best channels in the Florida Keys, providing easy access to BOTH the gulf and the Atlantic. This lot was previously used for the owner's water access from their landlocked home a

    Steven Koleno Beycome of Florida, LLC

    30860 Malaga Ln, Big Pine Key, FL 33043
  • /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
  • /3

    $120,000

    $15K PRICE DROP
    • Land
    • 15,000 Sq Ft
    • $348,480 per Acre

    19617 Date Palm Dr, Sugarloaf Key, FL 33042

    Now only $120,000. Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 Tier III platted lot (infill lot located in a developed subdivision with adequate infrastructure). With its prime location and desirable features, this property is a rare find in today's market. Convenient to the community boat ramp

    Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

    19617 Date Palm Dr, Sugarloaf Key, FL 33042
  • /14

    $255,000

    $255K PRICE INCREASE
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042

    Welcome to island living at its best in the gated waterfront community of Venture Out on Cudjoe Key. Lot 399 is a desirable 35' x 69' corner RV lot offering ocean peeks, full hookups, and endless possibilities. Whether you're looking for a personal Florida Keys retreat, an income-producing investment, or the perfect spot to build your future island home, this ROGO-exempt property checks all the

    Monika Rydzak eXp Realty LLC KW Branch

    701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042
  • /5

    $249,000

    $26K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $1,556,250 per Acre

    1155 Thatch Ln, Cudjoe Key, FL 33042

    Build your Florida Keys dream in Cudjoe Key just 3 lots from open water. Dock has already been approved and house plans are ready to submit to the county to begin the ROGO process.

    Tommy Mack Coastal Collection Real Estate Inc.

    1155 Thatch Ln, Cudjoe Key, FL 33042
  • /15

    $209,900

    • Land
    • 871 Sq Ft
    • $10,495,000 per Acre

    29859 Overseas Hwy Unit 27, Big Pine Key, FL 33043

    Welcome to 'The Island Girl'! This RV lot is an excellent investment at a low price. It is being booked as a very successful short term vacation rental with high profits and little overhead. This property is a little slice of paradise, lined with fruit trees and other tropical plants providing privacy and that 'keys vibe'. Enjoy the space anytime you want and rent it out the rest of the time.

    Cheryl Billings Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    29859 Overseas Hwy Unit 27, Big Pine Key, FL 33043
  • /60

    $175,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,120 Sq Ft

    27433 Antigua Rd, Summerland Key, FL 33042

    NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

    Kelly Gardner Bluescape Real Estate

    27433 Antigua Rd, Summerland Key, FL 33042
  • /2

    $180,000

    319 W Shore Dr, Summerland Key, FL 33042

    Skip the lengthy ROGO allocation process!Market Rate Transferable ROGO Exemption (TRE) available. One (1) lot transferable development right to use for residential construction in Monroe County. Buyer to verify parcel receivership eligibility.

    Francesca Santiago Chavez Keller Williams Key West Compass Realty

    319 W Shore Dr, Summerland Key, FL 33042

Home Price Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,164,000
Median Townhouse Sale Price
$1,750,000
Median 2 Bedroom Sale Price
$1,000,000
Median 1 Bedroom Sale Price
$689,000
Average Price Per Sq Ft
$921
Number of Homes for Sale
52
Last 12 months Home Sales
111
Months of Supply
5.60
Median List Price
$1,269,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
1%
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