18

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

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  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /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
  • 701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    /19

    $215,000

    • Land
    • 2,178 Sq Ft
    • $4,300,000 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
  • 701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    /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
  • 701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
    /58

    $269,000

    $26K 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
  • Lot 7 Parcel 10, Cudjoe Key, FL 33042
    Lot 7 Parcel 10, Cudjoe 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
  • 701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 69, 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
  • 701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
    /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
  • 701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 533, Cudjoe 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
  • 701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
    /50

    $289,000

    • 1 Bed
    • 1 Bath
    • 340 Sq Ft

    701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

    Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
  • 0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042
    0 Disturbed Pine Rd Unit 620297, Cudjoe Key, FL 33042
    0 Disturbed Pine Rd Unit 620297, 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
  • 701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
    /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
  • 701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 28, 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
  • 701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    /46

    $399,900

    $19K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 833 Sq Ft

    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

    This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 2 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 399, Cudjoe Key, FL 33042
    /14

    $265,000

    $265K PRICE INCREASE
    • Land
    • 2,178 Sq Ft
    • $5,300,000 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
  • 1155 Thatch Ln, Cudjoe Key, FL 33042
    1155 Thatch Ln, Cudjoe Key, FL 33042
    1155 Thatch Ln, Cudjoe Key, FL 33042
    /3

    $275,000

    • Land
    • 6,969 Sq Ft
    • $1,718,750 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
  • 124 Cutthroat Dr, Cudjoe Key, FL 33042
    124 Cutthroat Dr, Cudjoe Key, FL 33042
    124 Cutthroat Dr, Cudjoe Key, FL 33042
    /6

    $225,000

    $25K PRICE DROP
    • Land
    • 6,098 Sq Ft
    • $1,607,143 per Acre

    124 Cutthroat Dr, Cudjoe Key, FL 33042

    Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

    Jimmy Lane Island Life Realty Experts

    124 Cutthroat Dr, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 557, Cudjoe 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
  • 701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    /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
Florida Monroe County

Real Estate & Homes in Cudjoe Key, FL under $400,000

Home Prices in Cudjoe Key, FL

The median home sale price in Cudjoe Key, FL is $1,055,000, down 9% year-over-year. Homes in Cudjoe Key sell in 125 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$1,055,000
Median Single Family Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$685,000
Average Price Per Sq Ft
$815
Number of Homes for Sale
12
Last 12 months Home Sales
20
Months of Supply
7.20
Median List Price
$1,469,500
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-9%
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