32

Summerland Key, FL Homes for Sale under $400,000

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  • /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
  • /6

    $375,000

    • Land
    • 6,098 Sq Ft
    • $2,678,571 per Acre

    27378 Jamaica Ln, Summerland Key, FL 33042

    BUILD TODAY! Rare shovel-ready lot in the heart of Ramrod Key -- where Monroe County's permit moratorium has effectively stopped new residential development. This Breezeswept Beach Estates parcel comes with an ACTIVE allocated ROGO single-family PERMIT (SFDUP-2022-0059) already in hand. Foundation augers are in the ground. An Army Corps of Engineers-concrete seawall DOCK PERMIT APPLICATION IS

    Agent Photo

    Natallie Liz

    Island Welcome Real Estate LLC

    27378 Jamaica Ln, Summerland 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
  • /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
  • /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
  • /14

    $395,000

    • Land
    • 6,098 Sq Ft
    • $2,821,429 per Acre

    24285 Caribbean Dr, Summerland Key, FL 33042

    Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has

    Donna Pezzi Keller Williams Key West Compass Realty

    24285 Caribbean 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
  • /27

    $320,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

    Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
  • /4

    $350,000

    • Land
    • 8,276 Sq Ft
    • $1,842,105 per Acre

    22776 Overseas, Cudjoe Key, FL 33042

    Prime Cudjoe Key Commercial Opportunity! Cleared Suburban Commercial parcel offering outstanding highway frontage and excellent visibility on the Overseas Highway. Zoning SC allows for a variety of uses flood zone AE 9 tier 3 lot. For investment or owner-use. Owner financing may be available to qualified buyers. Bring your vision and capitalize on one of the Lower Keys' high-exposure commercial

    Rose Dell Keller Williams Key West Compass Realty

    22776 Overseas, Cudjoe Key, FL 33042
  • /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
  • /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
  • /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
  • /55

    $329,000

    $98K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 748 Sq Ft

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

    Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
  • /32

    $339,000

    $210K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

    Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 28, Cudjoe 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
  • /8

    $365,000

    • Land
    • 2,178 Sq Ft
    • $7,300,000 per Acre

    701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

    Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living.Located within the

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
  • /12

    $400,000

    $20K PRICE DROP
    • Land
    • 6,098 Sq Ft
    • $2,857,143 per Acre

    29517 Big Pine St, Big Pine Key, FL 33043

    Commercial waterfront lot at 29517 Big Pine St, Big Pine Key. Deep-water canal with quick access to both the Gulf of Mexico and the Atlantic Ocean, icommercial fishing, marine operations, boating, or waterfront business use. Located on a quiet cul-de-sac with exceptional privacy--no neighbors in front or on either side. Nearly surrounded by county-owned land that is not expected to be developed.

    Steven Koleno Beycome of Florida, LLC

    29517 Big Pine St, Big Pine Key, FL 33043
  • /27

    $350,000

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 726 Sq Ft

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

    Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

    Monika Rydzak EXP Realty LLC

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
  • /16

    $320,000

    $5K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $3,200,000 per Acre

    27935 Tarpon Terrace, Summerland Key, FL 33042

    Heather Mason Coastal Collection Real Estate Inc.

    27935 Tarpon Terrace, 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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