10

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

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  • 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

    $35K PRICE DROP
    • 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

    (645) 229-8475

    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

    $277,500

    $18K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

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

    INCOME PRODUCING POWERHOUSE! Welcome to 'Conch Hideaway' #423, a proven tropical retreat and turnkey business in the premier Venture Out community. This charming 1BD/1BA home is a high-performing vacation rental that grossed $30,705 in 2025! INVESTMENT HIGHLIGHTS: Already live with rentals for 2026, this property has 27 days currently booked with $2,085.05 in gross revenue transferring to the

    Kate Baldwin Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, 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
  • 0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
    /2

    $275,000

    • Land

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

    Builders and Developers 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 619097, 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

    $255,000

    $24K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

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

    Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area. The home is clean and well cared for, offering a functional layout appropriate for full-time

    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
  • 701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    /18

    $255,000

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

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

    Welcome to RV Lot 642, located in the gated, waterfront community of Venture Out on Cudjoe Key. This well-positioned lot offers the perfect setup for your Florida Keys getaway, seasonal stay, or investment opportunity.Enjoy all the perks of a golf-cart-friendly community with resort-style amenities, including a large saltwater pool, marina with boat ramp, pickleball and tennis courts, bocce,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 642, 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
  • 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

    Coby Taylor Expert Realty LLC (HQ)

    Unlisted Address
Florida Monroe County Cudjoe Key

Real Estate & Homes in Cudjoe Key, FL under $300,000

Home Trends in Cudjoe Key, FL

On average, homes in Cudjoe Key, FL sell after 74 days on the market compared to the national average of 58 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $1,225,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$1,325,000
Median 2 Bedroom Sale Price
$375,000
Average Price Per Sq Ft
$807
Number of Homes for Sale
10
Last 12 months Home Sales
15
Months of Supply
8.00
Median List Price
$1,463,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
13%
How to Buy a Home How to Finance a Home How to Sell a Home

Browse a range of homes for sale under $300,000 in Cudjoe Key, offering accessible options for prospective buyers. With 10 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Cudjoe Key, FL.

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